The Simple Plant Isoquinolines

Definitions: Consid Consider er botany. botany. What What is a taxon taxon?? It is the the name name which which identi identifie fiess a pla plant nt.. A taxon taxon is made made of two two part parts. s. First First,, ther theree is the genu genus, s, which which is a genera generall name name given given to a group group of close closely ly related related plants plants.. Seco Second nd,, the there re is the the spec specie ies, s, whic which h is the dist distin ingu guish ishin ing g name name given given to a speci specific fic plant in that group. group. A taxo taxon n is always always writte written n in italics. italics. Thus, Thus, for example, example, Pachycereus pecten-aboriginum pecten-aboriginum is the name of a cactus. Conside Considerr chemi chemistry stry.. What What are isoqui isoquinol noline ines? s? These These are chemica chemicall structu structures res built built around around a two-rin two-ring g compou compound. nd. This This compou compound, nd, Isoquin Isoquinoli oline, ne, consist consistss of a benzen benzenee ring ring and pyridi pyridine ne ring ring fused fused togeth together er at at a spec specifi ificc bond. There There is a patter pattern n of subs substitu titution tion that that gives gives an isoq isoquin uinoli oline ne its absolu absolute te defini definitio tion. n. Thus, Thus, for exampl example, e, Salsoli Salsoline ne is an isoquin isoquinoli oline, ne, which which is a majo majorr compon component ent of the the Pachycereus pecten-aboriginum plant. One can identi identify fy a plant plant by what it looks looks like, like, or by what is in it. it. Onecan identi identify fy a natura naturall compou compound nd by its its structu structure, re, or by by what what plant it is in. Know one, find the other. This reference book has been designed to make this cross-identification easier to achieve.

Definitions: Consid Consider er botany. botany. What What is a taxon taxon?? It is the the name name which which identi identifie fiess a pla plant nt.. A taxon taxon is made made of two two part parts. s. First First,, ther theree is the genu genus, s, which which is a genera generall name name given given to a group group of close closely ly related related plants plants.. Seco Second nd,, the there re is the the spec specie ies, s, whic which h is the dist distin ingu guish ishin ing g name name given given to a speci specific fic plant in that group. group. A taxo taxon n is always always writte written n in italics. italics. Thus, Thus, for example, example, Pachycereus pecten-aboriginum pecten-aboriginum is the name of a cactus. Conside Considerr chemi chemistry stry.. What What are isoqui isoquinol noline ines? s? These These are chemica chemicall structu structures res built built around around a two-rin two-ring g compou compound. nd. This This compou compound, nd, Isoquin Isoquinoli oline, ne, consist consistss of a benzen benzenee ring ring and pyridi pyridine ne ring ring fused fused togeth together er at at a spec specifi ificc bond. There There is a patter pattern n of subs substitu titution tion that that gives gives an isoq isoquin uinoli oline ne its absolu absolute te defini definitio tion. n. Thus, Thus, for exampl example, e, Salsoli Salsoline ne is an isoquin isoquinoli oline, ne, which which is a majo majorr compon component ent of the the Pachycereus pecten-aboriginum plant. One can identi identify fy a plant plant by what it looks looks like, like, or by what is in it. it. Onecan identi identify fy a natura naturall compou compound nd by its its structu structure, re, or by by what what plant it is in. Know one, find the other. This reference book has been designed to make this cross-identification easier to achieve.

v

TABLE TABLE OF CONTENTS CONTENTS

vi

Foreword Foreword I

xi

Foreword II Introduction

Trivial Trivial Name Name Index Index Structural Index Unsubstituted Monosubstituted Disubstituted 5,6- 5,7- and 5,8-subs 5,8-substitut tituted ed 6,7 -HO,HO-substituted -HO,HO-substituted 6,7-HO,MeO-substituted 6,7-MeO,HO-substituted 6,7-MeO,MeO-substituted 6,7-MDO-substituted 6,8-substituted 7,8-substituted Trisubstituted 5,6,7-substituted 5,6,8-substituted 6,7,8-substituted Tetrasubstituted Taxon Index Plant Families Appendix Isobenzofuranone Isobenzofuranone Appendix Journal Names Appendix

xiii 1

39 41

46 47 52 88 161 245

3 47 3 49 372 425 426 455 458 602

61 0 616

vi

FOREWORDI

The passion of my life over the last forty years has been a compelling interest in psychedelic drugs. They have given me not only an exciting area of research and discovery, but also a personal understanding of just who I am and why I am. Certainly these guides and sacraments will eventually play an accepted role in our community and in our culture. Almost all of these drugs have either been isolated from psychoactive plants, or are the results of subtle variations of the molecular structures of these isolates. I have always looked at these plants and the compounds they contain in the same way that the Romans dreamt of their ultimate empire. It was Caesar who acknowledged that all of Gaul was divided into three parts and to understand it, to conquer it, each part had to be respected as a separate entity. It is exactly the same way with understanding the world of psychedelic drugs. There are three domains of inquiry that must be studied independently before one can begin to appreciate just how they might integrate into a single concept. These three are now, I believe, coming together. One part is the large collection of psychoactive compounds known as the phenethylamines. The first known plant psychedelic was mescaline, or 3,4,5-trimethoxyphenethylamine. This simple one-ring alkaloid was discovered in the North American dumpling cactus Peyote (Anhalonium toilliamsii) in the late nineteenth century, and is now known to be a com ponent of over fifty other cacti. Over a dozen other cactus phenethylamines have been isolated and identified, and there are perhaps a hundred synthetic analogues that are now also known to be psychedelic in action. This body of information has been published by my wife Ann and me as a book entitled "PIHKAL: A Chemical Love Story." PIHKAL stands for Phenethylamines I Have Known and Loved. An almost-as-large chemical group contains the tryptamines. N,NDimethyltryptamine (DMT), its 5-hydroxy analogue (bufotenine) and the O-methyl ether homologue 5-methoxy-N,N-dimethyltryptamine (5MeO-DMT) are widely distributed in the world of natural plants. There are also the well-established mushroom alkaloids 4-phosphoryloxy-N,N-

vii dimethyltryptamine (psilocybin, and the dephosphorylated indolol psilocin)and the mono- and didemethylated homologues baeocysteine and norbaeocysteine. These seven natural alkaloids have provided the tem platefor perhaps two dozen analogue structures that are now well-establishedpsychedelic agents. Ann and I have written a companion volume to PIHKAL called "TIHKAL: The Continuation" (TIHKAL stands for TryptaminesI have Known and Loved), which has brought together most ofthesenatural and synthetic tryptamines into a single reference site. The remaining third of the above Gallic synthesis deals with what I had originally called the "Q" compounds, as distinguished from the "P" compounds and the "T" compounds (the phenethylamines and the tryptamines). The actual parent structural element is the isoquinoline ring system,and my initial plan was to give this third book a name similar to the first two. IIHKAL wouldn't do it, but QIHKAL shows a good bit of class, at least in my opinion. Or maybe THIQIHKAL because most of them are really tetrahydroisoquinolines. Well, all these names are now on hold, as Ann is uncomfortable with them. No name has yet been decided upon, but ideas such as The Third Book, or Book Three, are under consideration. Names like these resound with a rather striking arrogance, if nothing else. Tounderstand the relationship of the isoquinolines to the phenethylamines and the tryptamines, the concept of ring closure must be used. Thisis a sort ofsynthetic scorpion sting at the molecular level. A tryptamine has an indole ring as its centerpiece and from it there extends a floppy two-carbon chain terminated by an amino nitrogen atom. A small but very important family of plant alkaloids is the product of this amine ex ploitinga carbon atom from somewhere, and making a new six-membered ringby that "sting" reaction back onto the parent indole ring. This family hasthe name,~-carbolines, and the formed compound is 1,2,3,4-tetrahydro[3-carboline.

QCNH N I

H tryptamine

1,2,3,4-tetrahydro-~-carboline

A phenethylamine has a benzene ring as its centerpiece and it, too, has a floppy two-carbon chain extending out from it and also terminating in an amino group. In a reaction that is exactly analogous to that of the tryptamines,this amine can pick up a carbon atom and bend back to react

viii with the parent benzene ring forming a six-member ring. This is the origin of the isoquinoline family of natural products, and the formed com pound is l,2,3,4-tetrahydroisoquinoline.

phenethylamine

1,2,3,4-tetrahydroisoquinoline

As mentioned above, this third part of the plant psychedelic alkaloid world involves tetrahydroisoquinolines and is the substance of our third book. A very reasonable appendix to be written for this book would be a search of the chemical literature for the known isoquinolines that might be of interest as pharmacological agents. There are certainly many plant products, as well as a monster inventory of synthetics, some of which are made based on plant examples, but many others are simply laboratory creations of the imaginative chemist. It was soon apparent that this compilation would become unmanageably large. The first major trimming was the elimination of the compounds that were synthetic, and the limitation of the listing to those compounds that have been reported as plant products. These isoquinolines could play the dual role of serving not only as potential contributors to the action of psychoactive plants but also as prototypes for the synthesis of new materials that might themselves be biologically active. But even this restriction to only plant compounds was not sufficiently severe. There seemed to be no end to existing isoquinoline treasures. As I wandered deeper into the literature, I kept finding an ever-increasing inventory of research papers that described fantastic stuff. As a totally make-believe example, pretend that there was a compound named Dogabinine that has only been found in the Dogabic tree in the Twathtu rainforest, which the natives say cures leprosy, and which has a complex chemical structure that just happens to carry an isoquinoline ring in its lower southwest corner. To include all such monsters would make the appendix many thousands or even tens of thousands of pages long. And if you were to add into this compilation all the known derivatives, extensions and chemical modifications of Dogabinine, then you would have a review entity that would be several volumes in length. If such a collection were to exist, Iwould have it in my library right now. But it does not exist and it may never exist.

IX

Somemiddle ground, some rational compromise, had to be found. I wanted this collection to present all isoquinolines that are known to be plantalkaloids, but respecting carefully defined restrictions that exclude horrormonsters such as Dogabinine. The final compromise was to establishseparate entries for all the known two-ring isoquinolines that are from natural sources, including those that carry a third ring as a substituent (suchas a benzyl group) at the I-position. And within each of these entries,there are included all natural alkaloids that can be seen as products ofa hypothetical attack of an ortho hydrogen of this substituent on some other position of the isoquinoline nucleus. This "ortho-X attack" is exactlydefined and illustra ted in the Foreword tha t follows. All plant sources arerecorded (or representative sources if there are too many) and literature citations are also included in each entry. But even with these restrictions, this "appendix" to a third book was becoming larger and larger, and it soon became apparent that it was totallyinappropriate. There would be far too many pages for a minor ap pendixin a book that is to be dedicated to cactus and isoquinolines. And by the time my stream-of-consciousness commentary was added in the textwhere I felt it should be added, the mass increased to the extent that it had to be a reference book in its own right. Voila.Let's try to get all that information together into a single modest package and make it available to the chemists and botanists who might want it. Should it be a review article in Chemical Reviews or the Journal of Natural Products? Several factors said "No." Most botanical review surveys are not searchable except by taxon name (that would assume that youwould know the plant from which it came) or by some complex and maddening Chemical Abstracts entry that dealt with some alphabetizationthat demanded the knowledge of the structure and the way the structure would be listed. And most review articles also insist on a tidy forma t that is without editorial comment and does not contain volunteered ideas and extrapolations. An obvious solution became apparent. Create a single reference book to contain all this information. Use the chemical substituents as an alphabet. Visually travel around the structural image of the molecule in a logicaldirection,address the substituent groups in some logical way which willbe called alphabetical, and progress until you find the target you are searchingfor, or until you find an empty hole where it would have been had it been known. So this book has come into existence simply to meet this need, and to relieve the potential "Third Book" readership of a killer ofan appendix. Thenature of the substituents and, especially, the connection between simplebenzylated isoquinolines and the nature of the cyclized products ofortho attacks, are the heart and substance of this review book.

x

One additional comment is essential in this introduction. The extensive literature searching, and commingling of the accumulated plant and chemical data, taxed my capability and exceeded my patience. This was indeed a compilation that was essential to my current cactus research for the third book, but the task of its organization created a disruptive interference to my exploration of new psychedelics in unanalyzed cacti. The early help given me by Ann's daughter Wendy quickly evolved into her playing an indispensable role as my co-author. The final organization and structuring of this book has been largely the result of her dedicated labor. It is an honor to share the authorship with her as, without her help, this book would not exist today.

Alexander T.Shulgin

Xl

FOREWORD II

When Sasha and I began this project it was meant to be an appendix forthe next book in the series of PIHKAL and TIHKAL. It became so big that we knew after some time it could not be an appendix; it was its own book. So here it is, a collection of all the information we've compiled over thelast two years. It's been a daunting project at times. If we had included allthe variations of isoquinolines that we had originally planned to, this book would have been a series of volumes. Along the way we had to makedecisions about what was important to keep in, what we could leave out,what our focus was, what our intentions were. We pared down constantly,finally settling on the criteria that Sasha has laid down in the introduction. It is my belief that what we have put together here will be of great use to anyone interested in this particular field of botany and chemistry. We havetried to make the information as easy to find and review as possible, taking into consideration what it was like for us to search through the literature. Hopefully this compilation will make others' work much easier. Wefound so many mistakes in the literature, and even in the Chemical Abstracts,that we had to make educated guesses as to the correct way somethingwas spelled, or what a certain substituent was on a given ring; sometimeswe simply made comments in the text about a particular discrepancy.We welcome corrections and comments that come to us, as we surelyhave made errors ourselves. What I observed while going through the literature was enlightening. What stood out for me was how much of the plant research done on isoquinolineshas been in countries other than the United States. As many peopleknow, the state of objective, independent scientific research in this countryis a sad one. Research is at the mercy of special interests, government funding, and of harsh regulations and restrictions. It's rare to have a situation where a scientist is free to explore and discover, much less encouragedto do so. We are left to rely on research done in countries where the scientists' findings are not bought and paid for in advance, as hap pens in this country too often. Sasha is a rare chemist indeed, working independently for so long, free of those controls, and following his passionto discover tools to understand the mind and the brain in the face of

xii

much misunderstanding and misguided assumptions about psychoactive materials. As it is now, the pharmaceutical industry is bridging the gap between what is socially and legally acceptable to do to one's brain chemistry in order to feel well, and what is currently considered unacceptable, which is using chemical or plant medicines to look at why one is not feeling well to begin with. There is great hypocrisy, fear, and thoughtlessness afoot in the United States regarding psychoactive drugs. Their benefits and potential uses are lost in the rhetoric of the "drug war," and in the fear that it generates. There are many examples of healthy and informed use of psychoactive medicines throughout the world, and throughout the ages. They have been used in the past, and are being used today, as healing tools. We need that kind of thinking in this country, we need that kind of healing. Hypocrisy exists in the laws regarding alcohol and tobacco, which are legal, and are the most damaging and widely abused drugs in our culture. Many pharmaceutical drugs are not without their dangers and abuses as well (it's a fact that far more Americans die from pharmaceutical drugs than illegal drugs). What are the fears of psychoactive drugs really based on? I encourage those who start with the arguments of brain damage caused by this or that drug to obtain the actual scientific papers that make those claims (not just the titles of the papers) and read them carefully. They will find much misinformation due to political pressure, economics, and fear. It's been a blessing to work with Sasha, who is not only a brilliant chemist but a fantastic teacher. I had no background in chemistry when I began working with him; he has taught me so much. His passion and enthusiasm for chemistry is infectious; he has made it a delight to learn, and has shown me how magical it all is. It is magical, and mysterious, this world we live in and the stuff that it and we are made up of. It should be cherished, protected, and explored, with honesty and courage.

Wendy E. Perry

Introduction

xiii

INTRODUCTION

Forthis book to serve as a completely satisfactory reference, it must bestructured so that a reader who comes to it with one specific word inmind that is related to the simple, natural isoquinolines, can immediatelylocate all other related entries. Total cross-referencing is needed. Asa way to simplify this type of search, the main part of this book is actuallya collection of three indices. Each index is arranged alphabetically,very much like a dictionary. The first index lists the common trivialnames, the second lists the structures of the compounds themselvesand the plants that contain them, and the third lists the taxonomicnames of these plants and the compounds that have been found in them. Part 1: Trivial names of the plant alkaloids: Allof the known simple plant isoquinolines have been entered into thisindex under their common, or trivial names. Originally, there was alinearstructure code attached to the trivial name entry which allowed thereader to immediately deduce the chemical structure and to access thecompound directly in the structural index. It became apparent that a singlepage reference would do as well. Each trivial name thus leads to the chemical structure, the plants that contain that compound, and appropriate literature references. Many compounds have a number of trivial names. These may be puresynonyms for a single compound, or they may distinguish differentstructural or optical isomers. The quaternary amine alkaloid salts present an unusual problem. There are three naming procedures that arefrequently encountered. The quaternary salt may have a distinct one-wordname. Here there is no problem. However, the other two examplesare two- or three-word names, with the anion involved beingincorporated into the second word. As the fourth alkyl group on thenitrogen is usually a methyl group, the anion name would take one oftwo forms. If the parent tertiary amine is, say, the alkaloid Canadine, then the methyl quaternary salt could be called either NMethylcanadinium iodide or Canadine methiodide. Both are faulted in that the presence of the iodide anion in the product is the work of

xiv

The Simple Plant Isoquinolines the analyst, and it is not what was originally present in the plant. And if five people were to independently isolate this plant product and characterize it as a salt using the anions chloride, iodide, picrate, perchlorate and oxalate (all commonly found in botanical papers) it would demand five different index entries for a single plant alkaloid. In this present compilation, N-Methylcanadine quat will be the name used. But some quaternary amines are internally tetra-substituted. With com pounds such as the berberines where the c-ring is aromatic, there is no external "methyl" group to call upon. Here, using Caseadinium iodide as an example, the anion will also be dropped and it will be listed as Caseadinium quat. Part 2: Structural formulae of the plant alkaloids: The second, and major, index is the collection of structures and their plant sources. This section is also organized in an alphabetical way, but clearly the use of the classical A to Z order does not apply to the various arrangements of atoms. Let's say you have the structure of a simple isoquinoline in mind, and you would like to know if it is a known plant alkaloid. The classic academic process is to head over to the University library and start going through the many collected indices of the Chemical Abstracts, and search it out by what you hope is the right chemical name. But sadly the rules of naming are continuously changing. Sometimes 5,6,7,8-tetramethoxy precedes l,2,3,4-tetrahydro, and sometimes it follows it. Sometimes 6,7-methylenedioxy-l,2,3,4tetrahydroisoquinoline is filed in just that way, but sometimes it is filed under benzodioxolol4,5-gJ5,6,7,8-tetrahydroisoquinoline. And just what are the Chemical Abstracts' structural naming rules and numbering systems for four-ring systems such as aporphines, isopavines or berberines? The "alphabet" used in this structural index is totally indifferent to the capricious and arbitrary rules laid down by the Chemical Abstracts. Quite simply, it is based on the location of the substituents and their identity in the nuclear isoquinoline skeleton before it is distorted by a hypothetical "ortho attack." The definition of this "atomic" alphabet is the substance of this introduction. The nature and variety of this "ortho attack" is addressed here as well. Part 3: Botanical names for the plants that contain these alkaloids: All plants have been entered into the third index alphabetically, according to genus and species. Under each of these taxa are listed the trivial (or chemical) names of the alkaloids reported to be in that plant.

xv

Introduction Part 4: Appendices: There are three appendices located at the end of this volume. The firstis a listing of the botanical families that are mentioned in this book, and the Genera that each contains. Second is an analysis of the nonintuitive process used by Chemical Abstracts to create the name of an isofuranone-substituted isoquinoline. The third is the list of actual journal names that are given only as initials in the references in the structural index.

THEATOMIC ALPHABETIZATION

OF COMPOUNDS

There are two "alphabets" used in the organization of this book. Boththe index of trivial names and the listing of the botanical binomials use the English A to Z, 26-letter convention, like a dictionary, and the words can be of any length. The listing of compounds in the structural index is also "alphabetical," but it employs a hierarchy of positionallocations and structural substituents as its alphabet. Each structure is a five-lettered "word" and the priority follows the rules of the dictionary. With the structure being sought in mind, one must go through the list of compounds with the first "letter" (substituent) in mind, and then the second "letter" is located, and on, and on. Below is a list of the priorities each substituent ("letter") follows. (l) POSITION ON THE AROMATIC RING Here is the primary assignment of numbered positions, and the assignment of letters to the individual bonds, of the isoquinoline ring:

600~ 5

4a 4

I

7 ~

8

3

~N2

8a 1

9

ed

C

f

OJ - : / '" ~ h

I

i j

~

b

~N a

The first "letter" of the chemical name of the structure being sought is created from the position of the substituents on the aromatic benzene ring. There are four positions available (5,6,7,8), and they are al phabetically arranged from small to large and from few to many.

The Simple Plant Isoquinolines

xvi This is the order:

5,6 5,7 5,8 6,7 6,8 7,8

5 6 7 8

none

5,6,7 5,6,8 5,7,8 6,7,8

5,6,7,8

Thus a compound with a 5,6-disubstitution pattern is to be found in this dictionary immediately following the 8-monosubstituted entries and immediately before the 5,7-disubstituted entries. All numbering has been taken exclusively from the assignments given to the isoquinoline ring. There are situations such as the methylenedioxyisoquinolines where the nature of the substituent constitutes a new ring. In this case, as in many others, Chemical Abstracts would assign totally different numbers to these four positions on the aromatic ring. Currently correct numbering systems are ignored here, and the primitive 5,6,7 and 8 positional identifiers are used exclusively. This first letter of the structural alphabet is used as a heading for the appropriate subsection of the second index, the structural formula group. (2) THE SUBSTITUENTSON THE AROMATIC RING The second "letter" of the chemical name is the actual substituent or substituents found at the positions designated by the numbers above. There are only three substituents to be considered in this chemical al phabetical sequence; they are, in order:

code used: HO MeO MOO

atomic connections: HOCH30-OCH20-

common name: (hydroxy) (methoxy) (methylenedioxy)

The HO- group is exactly what it appears to be. It is a hydrogen atom bonded to an oxygen atom which is, in turn, bonded (at least in the case of the second letter of this chemical alphabet) to one or more of the available positions on the aromatic ring of the isoquinoline, i.e., the 5,6,7 and/or the 8 positions. The MeO- group, as drawn, is an ab-

Introduction

XVll

breviationfor a slightly more complex structure, a methyl group (H3 Cor-CH3)bonded to an oxygen atom which is, as above, attached to one (or more) of the four positions of this aromatic ring. The MOO, or methylenedioxy group, is yet a bit more complex. It is unique in that it is a double-ended substituent. It is a short chain that involves an oxygenatom (0) connected to a methylene group (CH2) connected in turn to another oxygen atom. Drawn out as a collection of atoms it is -OCH20-and thus requires two adjacent substituent positions and must be associated with two numbers. Let's use the 5,6 substitution position as an illustration template, and we'll introduce some substitution second "letter" examples, in al phabeticalorder:

5,6 HO HO 5,6 HOMeO 5,6 MeOHO 5,6 MeOMeO 5,6 MOO

precedes precedes precedes precedes

A few things are obvious. Where a thing is located (shown by the numberor numbers) has priority over what a thing is (the substituent or substituents). This same locating and identifying code will be used for the benzyl group on the I-position, but with some extensions which will be explained below. There is, of course, a fourth allowable substituent. This is H (a hydrogen atom), but it is automatically assumed to be on every num beredposition not carrying one of the three given oxygenated examples. It is generally accepted, in the creation of a name to represent a chemicalstructure, that if there is no substituent specified on the aromatic ringthe substituent is hydrogen, and is not entered. The presentation ofthe entry

5,6

MeO HO -

without this exclusion, would have been

5,6,7,8 MeO HO H H

What about substituents that are groups other than HO, MeO or MDO(and of course the unsubstituted H)? Homologues of Mea such asethoxyand benzyloxy (Eta, BzO), alkyl groups such as methyl, phenyl,halides, carboxy or substituted carboxy groups, esters of phenols,

xviii


nitrogen-containing groups such as nitro or amino derivatives, thio compounds, all are regularly encountered as substituents of isoquinolines in the chemical literature. And since almost all of them are products of synthesis rather than plant products, they are ignored in this compilation. There is an occasional exception, like an O-acetyl derivative that appears to have been isolated from some natural source. There are plant alkaloids known that can, within the plants' environment, undergo extensive oxidation. In the aporphine group, a com pound such as N orcorydine can go to the quinone, all four rings com pletely aromatic and a carbonyl at the 7-position where the hydroxy group once was. This is the base Pancoridine. So a quinonic carbonyl can appear in the aromatic ring. But its origin was a hydroxy group. So, for all practical purposes, we are staying with the three substituents mentioned above (other than hydrogen). The substituents that are on the benzene ring are listed on the first line in the box at the upper left corner of each compound's entry, in the sequence that corresponds to the number or numbers at the top of the page.

6-MeO 7-HO 3,4-MeO,MeO-benzyl H IQ

(3) THE I-POSITION The third "letter" of this alphabet is the substituent that is found at the I-position of the isoquinoline ring. This is the first involvement of the pyridine ring position of the isoquinoline system, so a number of new factors must be considered. There are always two substituents at this position but, depending on the degree of aromaticity of this ring, one of them might be meaningless. And, as there are two substituents, there must be a rule that ranks them. If they are different, the heavier will precede the lighter. This lighter one will be a hydrogen or a methyl group (abbreviated Me). And occasionally there will be a substituent that embraces both substituents as a single thing. And again, as above, there will be occasions where the unnamed substituent is simply hydrogen, and is not mentioned. Here is the sequence that will be used, listed by what the substituents really are, and by how they will be entered.

xix

Introduction Lighter substituent at the [-position:

Heavier substituent at the I-position:

Appearance of this third chemical letter: H

H H

H

Me Me

Me Me,Me OH or (=0) OH,Me R R,Me R,HO

Me

OH OH

H

R R R

H

Me Me H O

In those cases where there are two different substituents, this car bon atom becomes chiral. Most natural products have optical activity, but in many plant analyses, the optical rotation is not reported and probably not measured. In the literature there is no way to distinguish between an unknown rotation and a racemate. In these cases, all plant sources for a given isoquinoline have been commingled without regard to the reported optical activity, unless it is known. The "R" that is mentioned above is one of five aromatic systems, and these are usually substituted themselves. These aromatic systems and their numbering are ranked as shown below:

6 c r .c.' 5

~

4

3

~

~

2

4

3

R= phenyl

R= benzyl

6

2

5

3

R= ~-phenethyl

5¢¢ I

6

~

7

5~ I

0

6

7

OH

R= isobenzofuranol,

~

3'-yl

0 0

R= isobenzofuranone,

3'-yl

The priorities for both the numbering and the substituents follow the same patterns established for the first and second chemical letters.


xx

Numbering priority: none

2 3 4

2, 3, 4 2, 3, 5 2, 3, 6 2, 4, 5 2, 4, 6 3, 4, 5

2,3 2,4 2,5 2,6 3,4 3,5

2, 3, 4, 5 2, 3, 4, 6 2, 3, 5, 6

2 , 3, 4, 5, 6

And once the numbers have been decided upon, then the substituent is chosen from the following sequence: H O MeO MOO

Again, there are many known compounds that have phenyl, benzyl or phenethyl rings at the 'l-position with substitutions other than these three (and the understood and unstated hydrogen atom of course). And, as with the 5,6,7,8 substitution story, most of these are synthetic products and are not part of this book. The few unusual substitutions that are known to be in compounds from natural sources, such as the formyl (CHO) and the carboxyl group (C02H), will be included. The rule of organization is: a group bonded with a carbon atom has priority over a group bonded with an oxygen atom. Occasionally there is a carbon or an oxygen substituent found on the alpha-carbon atom of the benzyl group. This is taken into account in the alphabetization. These substituents have the following priority: Mono-substituted Me (methyl) HO (hydroxy) AcO (acetoxy) MeO (methoxy) NH2 (amino)

Oi-substituted Me,Me (dimethyl) Me,HO (methyl, hydroxy) = CH2 (rnethenyl) = 0 (oxo) or (keto)

The presence of a carbonyl at the 'l-position introduces an ambiguity. In most cases, the structure of the I-keto product can be redrawn as a I-hydroxy tautomer with the inclusion of a double bond in the piperidine ring to balance the equation. When this situation occurs, the compound will be entered as the keto tautomer.

XXI

Introduction

OQ

O )H a

OH

This third letter of the atomic alphabet, the 'l-position, is entered on thesecond line in the box found at the upper left corner of each entry.

-~.-


(4) THE 2-POSITION The fourth "letter" in this chemical alphabet is the substituent at the 2-position, the nitrogen atom, of the isoquinoline ring. The primary substituents found here are the hydrogen and methyl groups, and they are arranged by increasing number: H Me Me (+) Me,Me(+) CHO C02H Ac (COCH3) CONH2 C02Me C02Et

(formyl) (carboxy) (acetyl) (carbamoyl,

or urea)

(carbomethoxy)

(carboethoxy)

An "H" as the fourth letter does not necessarily mean that there is a hydrogenat this position. It is an indicator of the absence of any substitution on the nitrogen. This, as with the absence or presence of a (+) charge at that position in the methylated examples, reflects the aromaticity of the pyridine ring. This is discussed below in section (5). There are also found, occasionally,amide functions on this nitrogen atom. Oxidation at this position is frequently found. Hydroxylamines and N-oxides are entered either as footnotes to their non-oxygenated


XXll

counterparts or as entries in their own right. There are about a dozen plant isoquinolines that have benzyl substituents on the nitrogen atom. They are included in this collection. This fourth letter of the atomic alphabet is found at the left side of the third line in the box at the upper left corner of each entry.


t (5) HYDROGENATION The fifth letter of the chemical alphabet is the simple statement of the degree of hydrogenation of the pyridine ring, and the three codes are ranked in the order of increased aromaticity,

THIQ DHIQ IQ

tetrah ydroisoq uinoline dihydroisoquinoline isoquinoline

THIQ is l,2,3,4-tetrahydroisoquinoline. Both double bonds in the pyridine ring are hydrogenated. If the fourth letter is an "H," there is indeed a hydrogen on the nitrogen. If there are methyl groups there, a single methyl will be without a charge, but two methyls will require a (+) charge. DHIQ is specifically 3,4-dihydroisoquinoline. If the fourth letter is an "H," there is no substitution on the nitrogen, even though there will be an H written on the third line on the left side. If there is a methyl group indicated, there must be a (+) associated with it. There is an occasional natural dihydroisoquinoline in which the hydrogenation is at the l,2-positions and the unsaturation is at the 3,4-positions. These have been entered as a footnote under the THIQ compound as 3,4-ene.

Introduction

XX111

IQis the completely aromatic compound. Again, in this case, if the 4thletter is indicated as an H, there is no substituent on that nitrogen positionand if there is a methyl there, it must have a (+) on it. This last letter is noted as a THIQ, DHIQ or IQ on the right-hand side of the third line in the box at the upper-left corner of the compound's entry.


t THE oRTHo ATTACK

Oneof the little appreciated but totally fascinating properties shared by perhaps a dozen of the classes of four-ring isoquinolines is that most ofthemcan be visualized as resulting from an ortho attack," from the 2 - or6-hydrogen atom of the I-substituent (usually a benzyl group) to somespecifically identified position of the isoquinoline ring. These conversionsmay certainly have biosynthetic reality. But they have a greatdeal more importance for this book in that they allow a simple andfoolproof way of organizing the compounds in text. To locate the targetcompound under which the four-ring material will be found, simply mentally note the I-benzylisoquinoline that constitutes its chemicalskeleton. The bond forming the fourth ring can be identified asgoingfrom an ortho-position of the benzyl to some numbered atom onthe isoquinoline. Below they are illustrated and identified as to the alkaloidalclass name. One must keep in mind that the benzyl ring has twoortho hydrogens. If it is not symmetrically substituted, the normalnumbering priority sequence is used, and that will dictate whether theorthohydrogen employed in the attack is a 2- or a 6-hydrogen. The examplesbelow show ortho (2,X) attacks. It should be understood that thesubstitution pattern on the benzyl ring could require that they be calledortho (6,X) attacks. The ortho attacks will be indicated in each sectionin a separate box from the first. Thus, the first box in each sectionis the parent compound, and any additional boxes will be modifications,such as an ortho attack, an N-oxide, or other changes. 11

xxiv


Spirobenzylisoquinolines

The ortho (2, 1-Me) attack

This family is classified in this collection as an ortho-attack on a l,l-disubstituted tetrahydroisoquinoline where there is a methyl, or some other group (an ortho (2,1-XX)attack).

Dibenzopyrrocolines

The ortho (2,N) attack

Here the hypothetical2,N (or 2,2)attack produces a five-membered ring. The tetracyclic product is treated here as an isoquinoline, but it can also be seen as a disubstituted dihydroindole. The usual chemical classification is that of a substituted pyrrocoline, the name for the heterocycle that is the middle two rings of this system.

Introduction

xxv

Protoberberines (Berberines) and Protopines

The ortho (2,N-Me) attack

with ring C aromatic

The N-methyl oxo and oxy forms

Thisis one of the more common ortho attacks, and gives rise to the protoberberinesand, with a minor substitution change, the protopines. I have always assumed that the protoberberines were the saturated precursoralkaloids (proto- meaning early or source) which upon aromatizationgave the berberines with an aromatic ring "c." It now looks asifthe entire group is often simply called the protoberberines. In the four-ringprotoberberine with the ring "C" aromatized, the hydroxylationof the carbon atom that was the original N-methyl group leads to

XXVI

The Simple Plant Isoquinolines a group of compounds called 8-oxy (or 8-oxo) berberines. This tautomeric interconversion is shown above. If there is a hydroxy group as well as a benzyl group on the I-position and there are two N-methyls in the THIQ ring (the quaternary salt), another family can be explored through this 2,N-Me attack. These alkaloids are of the protopine class, but to understand their structures little tautomeric manipulation is needed.

an ortho (2,N-Me) attack

Tautomeric

equilibrium

A tautorner is a bit of structural sophistication. One can move the electrons around, without moving any of the atoms, and some end up with quite a different looking thing. Which is it? It's a bit like the problem with the duality of the photon. It is a particle and it is a wave, both. It pretty much depends on how you look at it. The middle structure, with an 0- and an N+, should be rather soluble in water. It is an ionic doubly charged molecule, after all. But the structure on the right is a ketone and an amine, and would probably be lipophilic, and wouldn't dissolve in water. Is it water soluble? Hard to use that as a way of telling the structure because just the act of putting it in water might shift the electrons towards the ionic configuration. As they say in quantum mechanics, you can't observe anything without changing it in some way. These compounds will be portrayed in the 4-ring structure with the 0- shown as a hydroxy group in the structural index.

Introduction

xxvii

Pavines

The ortho (2,3) attack

The pavine family, created by the ortho-3 attack, has an unusual property not shared by any other isoquinoline group. The pavine can be viewed in either of two ways, left to right, or right to left. This is best seen in the above structural diagram on the right. View the lefthandbenzene ring as the aromatic ring of the THIQ, and then go to the first carbon atom at the 4 0'clock position. The nitrogen bond in the centerdemarks the second ring of the isoquinoline, with the I-position beingthe point between these two locations, at the bottom. The car bon bond out to the right of this point shows the benzyl group. Now view the right-hand benzene ring as the aromatic ring of the isoquinoline,and then go to the carbon atom at the 100'clock position. The nitrogen bond in the center demarks the second ring of the isoquinoline; the point above is the I-position, and the carbon bond out to the left is the benzyl group. Thus any pavine with different substituents on the two benzene rings could result from an ortho (2,3) attack of either of two different isoquinolines. These items are entered both ways in this book. And in thecaseof pavines here, and the isopavines below, if there is a methyl group on the nitrogen, it will be represented by the abbreviation Me instead of CH3.

XXV111


Isopavines 4 4

1

~

I

2

~ ~

The ortho (2,4) attack

Unlike the pavines, the unusual internal N-bridged heterocycle of the isopavines admits to an isoquinoline classification in just one direction.

Morphanans

The ortho (2,4a) attack

This ortho-4a attack, forming the carbon skeleton of the morphine molecule, is one that is not easily visualized by non-chemists. It requires an out-of-plane manipulation to bring the benzyl group into con junction with the ring-juncture 4a carbon atom. The I-benz ylisoquinoline is shown in its conventional form on the left. To picture the attack, mentally take hold of the benzyl group and bring it back,

Introduction

out of the plane of the paper, to where the 2-position is pointing directlyat the 4a-position. This is the only one of the ortho attacks that is superficially not an oxidation. The consequence is that the aromatic resonancestatus of the benzenoid ring of the THIQ is permanently lost. Thelocation of the residual double bonds and other electrons depends totally on the substitution pattern of the isoquinoline aromatic ring. Oncethe attack has been achieved, the plant world makes many further chemical steps, leading to a host of alkaloids related to thebaine and morphine, both of which contain an additional heterocyclic furan ring. They lie beyond the scope of this compila tion. An unna tural, but fascinating compound is the (+) isomer of the product of this attack with a 4-methoxybenzyl on the I-position, a methyl on the nitrogen, and hydrogenation of the resid ual benzene ring of the pa ren t isoquinoline. This product is the broadly abused antitussive, dextromethorphan, or DXM. Another family of alkaloids, the Hasubanans, are often lumped togetherwith the Morphinans beca use of a superficially similar morphology. As an illustration:

CHsO

HO

CHsO

o Sinoacutine (a Morphinan)

OCHs Cepharamine

They are actually indoles, not isoquinolines, included in this listing.

(a Hasubanan)

and so they are not

XXIX


xxx

Aza£luoranthenes

The ortho (2,8) attack (with a 1-phenyl)

Although most ring-substituents on the 'l-position of the natural tetrahydroisoquinolines are substituted benzyl groups or isobenzofuranones, occasionally a phenyl grou p is observed, bound directly to the isoquinoline ring. An ortho (2,8) attack leads directly to the indino[l,2,3-ij]isoquinolines, known commonly as the azafluoranthenes.

Aporphines

The ortho (2,8) attack (with a 1-benzyl)

This family is viewed as an ortho-attack on the S-position of the isoquinoline ring. This produces a four-ring system known as an aporphine. Well over a hundred years ago it was discovered that morphine, when treated with a strong acid, gave rise to the compound apomor phine, an aporphine. It is now known that the lower of the two aromatic rings of apomorphine is the result of the rearomatization of the benzyl group, which was compromised by the ortho-4a attack men-

Introduction

XXXI

tionedabove. But at the time it was thought to be a simple conversion, and for a long while the structure of apomorphine was thought to representthe skeleton of morphine itself.

Cularines

The ortho (2,8-0H) attack

Hereis the generation of a 7-membered oxygen-containing

heterocycle.

Proaporphines

The (1,8) attack This is a Ll-spirobenzyl intermediate to what is quite likely the entirefamily of the aporphines. The "pro" part of the name suggests that this is a biosynthetic precursor to these alkaloids. Very often there isa keto function at the 4-position of the benzyl group (equivalent to a hydroxylgroup on the original benzyl), to facilitate the spiro loss of aromaticityneeded to achieve this type of coupling. This is directly analogousto the (2,4a)attacks needed to get into the morphinans, where


XXXll

a ketonic presentation of an aromatic hydroxyl group permits the bonding to occur.

5-p hen y lfurano [2,3,4- i j I isoq uino 1ines

/OH/ 8-HO

a-H

The a,B-HO attack

There are several reports of tetrahydroisoquinolines with a fused furan ring that could be argued (for the sake of the classification used in this collection) as an oxidative attack by the a-hydrogen of the 1 benzyl onto the 8-HO substituent, in a manner similar to the formation of a seven-membered ether ring seen in the cularines. It can also be seen as a similar oxidative attack from an a-hydroxy group (a commonly encountered benzyl substituent) on the 8-hydrogen position. The first of these two mechanisms (illustrated above) is used in this collection.

THE SECOISOQUINOLINES The prefix "seco" is an unusual term occasionally encountered in the literature of natural products. Just as the term "ortho-attack" indicates the generation of a new ring, the term "seco" indicates the destruction of a ring. A secoisoquinoline is formed from a 1-substituted tetrahydroisoquinoline by the loss of the 1,2-bond. Transferring a hydrogen atom from the a-carbon to the nitrogen, and reshuffling the electrons, results in the formation of a new double bond.

Introduction

XXX111

Phenethylamines

a

a 1,2 seeo bond loss

In an appendix to the book "TIHKAL: The Continuation" there were listeda number of the phenethylamines known to be in the cactus family. These were all of classical simplicity with the phenyl ring substituted with one or more hydroxys and methoxys, and an occasional methylenedioxy group. There was also an occasional hydroxy group onthe beta position of the chain, and on the nitrogen atom there were zero, one, or two methyl groups. There was no mention made of a subclassof phenethylamines which are intimately associated with the isoquinolines. The chemical term "seco" is a clever device for maintaining a structural relationship between two chemicals after having, magically,removed a structural bond. Illustrated here is an aporphine withthe electrons from that l,2-bond having been rearranged into the middle ring. It would probably be chemically classified as an aminoethyl-substituted phenanthrene, rather than a phenethylamine which had been fused (2,3a) with a naphthalene, but in this book it will be listed in the section describing the parent I-benzyltetrahydroisoquinoline, modified with an ortho attack if appropriate, followedby a l,2-seco bond removal.

XXXIV


With the simpler l-benzyl derivatives (those which have not undergone any ortho-attack), the removal of the 1,2-bond usually produces a 2-styryl substituted phenethylamine. Again, this would be located in the entry that described the parent isoquinoline. The second illustration above is a phthalide THIQ, and these phenethylamines are sometimes referred to as secophthalideisoquinolines. Here, the oxygen atom of the original isofuranone ring is substituted on the newly formed double bond. This structure can easily open up to the corresponding ketonic carboxylic acid. These secomodifications of the attacked isoquinoline (first example, illustrated with an aporphine) and the simpler I-substituted isoquinolines (second example, as illustrated by the isobenzofuranone) are the only ones included in this book. The standard phenethylamines that are commonly found in cacti, compounds which are not from these seco-mechanisms, have been tabulated in TIHKAL and will not be repeated here. There have been many compounds excluded from this compilation, but to give examples would increase the mass of this collection without any useful information. They are, in a general hand-waving sense, those compounds not explicitly allowed in the above inclusion criteria. Toall rules, there are always exceptions. These have been made to allow unexpected natural isoquinolines that just happen to present unexpected substituents that nature for some reason chose to contribute to this collection. Mention has been made of an occasional carbonyl group disrupting the aromaticity of the benzene ring (this is the basis of the quinonic isoquinolines). The nitrogen atom (position 2) occasionally displays an amide group (these have been entered at the fourth letter of the structural alphabet). Several natural compounds demand a hydroxyl or methoxyl function at the isoquinoline 3- or 4 positions. When this occurs, the compound is listed as a footnote under the parent structure. More difficult to generalize, are the isoquinolines with new rings resulting from biosynthetic attacks from here to there that are excluded from this study. In a broad, inclusive statement the line has again been drawn to exclude everything that has not been included above. Originally it was intended to list every plant in which these natural isoquinolines are found, documented with a literature reference. The project became unmanageable in that some of the more common alkaloids have been found in literally hundreds of plants. So, in some cases, if there are many species from one Genus, the plant listing will be condensed to mention the particular Genus, the family, plus a literature reference; e.g., Corydalis spp. (Papaveraceae) jnp 51, 262 '88. This way the broadness of distribution is established. Also, there are

Introduction

xxxv

sectionsin the structural index where there is a compound that has oneor more synonyms. In some instances, synonyms of what are sup posed to be the "same" compound have been given different lists of plants. So, it could be that different names are given to represent differentoptical isomers, we don't know. But in most cases the differentiation was respected, the lists of plants to a given name were kept separate within a given section. For much of the plant information we are most grateful for being allowedaccess to the NAPRALERT (sm) database at the University of Illinoisat Chicago, and would highly recommend the use of their servicesif more detailed information is wanted. In particular, we appreciatethe help of Douglas Trainor there. Also, we'd like to give great thanksto Jim Bauml, the Senior Biologist at the Arboretum of Los AngelesCounty, for helping to resolve many plant name and family issues,Amy Rasmussen for her supurb proofreading skills, and Frani Halperin for her artwork on the cover of this book.

Trivial Name Index

I

TRIVIAL NAME INDEX

Acetonyl-reframidine N-A cet yl an olo bi ne N-A cet yl an ona in e N -A cet yl an halam in e N -A cet yl an haloni ne N -A cet yl as im ilo bi ne D-Acetylfumaricine N -A cet yl laure lli ptin e N -A cet yl lauro litsin e N -A cet yl -3 -m et hox yno rn an teni ne N -A cet yl -3 -m et hox yno rn uc ifer in e N -A cet yl no m an te ni ne N -A cet yl no m uc ifer in e N -A cetyl -s ec o- N -m et hyl la uro te tanin e N -A cetyl step har in e D-Acetylsukhodianine N -A cetyl xy lo pi ne Actinodaphnine Acutifolidine Adlumiceine Adlumiceine enol lactone Adlumidiceine Adlumidiceine enol lactone Adlumidine Adlumine Aducaine Aequaline Alborine Alkaloid Fk-5 Alkaloid PO-3 Allocryptopine a-Allocryptopine Alpinone

312 263 252 431

44 5 57 165 133 68

40 7 396 22 9 172 196 181

282 269 284

85 243 243 344 344

340 241 139 70 450 108

96 327 327 223

2

The Simple Plant Isoquinolines Amurensine Amurensinine Amurine Amurinol I Analobine Anaxagoreine Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Anibacanine Anicanine Anisocycline Annocherine A Annocherine B Annolatine Annonelliptine Anolobine Anomoline Anomuricine Anomurine Anonaine Aobamine Aobamidine Apocavidine Apocrotonosine Apocrotsparine Apoglaziovine Aporeine Aporheine Aporpheine Argemonine Argemonine me tho hydroxide Argemonine N-oxide Argentinine Argentinine N-oxide Arizonine Armepavine Arosine Arosinine

292 301

154 155 262

59 429 431 439 432 443 432

93 175

403 104 105 107 388

262 388 37 6

399 24 6

324 344 157

60 100 103 24 8 24 8 248

21 3 218

214 56 56 354 178

15 2 133

3

Trivial Name Index

Artabonatine A Artabonatine B Artavenustine Aryapavine Asimilobine Asimilobine- 2-0-~-D-glucoside Atheroline Atherospermidine Atherosperminine Atherosperminine N-oxide Aurotensine Ayuthianine Backebergine Baicaline Belemine 2-Benzazine l-Benzylisoquinoline Berberastine Berbericine Berbericinine Berberilycine Berberine Berberrubine Berbervirine Berbine Berbin-8-one Berbithine Berbitine Berlambine Bernumicine Bemumidine Bemumine Beroline Bharatamine Bicuculline Bicucullinidine Bicucullinine Biflorine Bisnorargemonine Boldine Boldine methiodide Bracteoline

25 5 41 0

63

449 54 55

19 9 41 1 17 2 17 2 11 4 26 1 16 1 42 4 26 4

39 39 29 9 29 7 21 0

300 29 7 28 5 324

40 28 5 321 321 29 9 53 16 5 53 28 5 91

342 24 3 345 329 71, 122 67 68

13 8

4


Breoganine Bromcholitin Bulbocapnine Bulbocapnine methiodide Bulbocapnine N-oxide Bulbodoine Buxifoline Caaverine Califomine Califomidine Calycinine Calycotomine Canadaline Canadine a-Canadine ~-Canadine Canadinic acid Canelilline Capaurimine Capaurine Capaurine N-oxide Capnoidine Capnosine Capnosinine N-Carbamoylanonaine N-Carbamoylasimilobine N-Carboxamidostepharine Carlumine Camegine Carpoxidine Caryachine Caryachine methiodide Caseadine Caseadine N-oxide Caseadinium quat Caseamine Case amine N-oxide Caseanadine Caseanidine Caseanine Cassamedine Cassameridine

349 214 286 288 286 326 41 2 91 311

314 318 166 296 296 296 296 324 93 43 6 43 7 43 7 340 90

162 251 57 182 242 164 305

82, 287 83, 288 365 365 365 362 362 364 364 207

41 9 317

5

Trivial Name Index

Cassyfiline Cassyformine Cassythicin e Cassythidine Cassythine Cataline Catalpifoline Cavidine Celtine Celtisine Cephakicin e Cephamonine Cephamuline Cephasugine Cerasodine Cerasonine Chakranine Cheilanthifoline Cherianoine Cinnamolaurine Cissaglaberrimin e Cissamine Oarkeanidine Claviculine Coclanoline B Coclaurine Cocsarmine Codamine Codamine N-oxide Colchiethanamine Colchiethine Colletine Columbamine Constrictosin e Coptisine Corarnine Coreximine Corftaline Corgoine Corledine Corlumidine Corlumine

415 415 287 418 415 217 205 230

363 349 426 428 428 426 137 147 197 81

427 275 382 128 359 349 191 97 204

141 141

85 85 106

143

42 309 121 121 335

89 86 86

242

6


Corphthaline Corunnine Corybrachylobine Corybulbine Corycavidine Corycavamine Corycavine Corycularicine Corydaldine Corydalidzine Corydaline Corydalisol Corydalispirone Corydalmine Corydalmine methochloride Corydalmine N-oxide Corydecumbine Corydine Corydine methine Corydine N-oxide Corydinine Corygovanine Coryrnotine Corynoxidine Corypalline Corypalmine Coryphenanthrine Coryrutine Corysamine Corysolidine Corystewartine Corytenchine Corytenchirine Corytensine Corytuberine Coryximine Cotarnine Cotarnoline Coulteroberbinone Coulteropine Crabbine Crassifoline

335 152 221 79

328 331 331 353 239 72

220 321 332 202 221 203 335 143 152 145 329 154 221 209 88

74 217 338 315

157 326 196 196 340 120 32 5 447 445

448 448 194 35 9

7

Trivial Name Index

Crassifoline methine Crebanine Crebanine N-oxide Cristadine Crotoflorine Crotonosine Crotsparine Crotsparinine Crychine Crykonisine Cryprochine Cryptaustoline Cryptocavine Cryptodorine Cryptopine Cryptopleurospermine Cryptostyline I Cryptostyline II Cryptostyline III Cryptowolidine Cryptowoline Cryptowolinol Cucoline Culacorine Cularicine Cularidine Cularidine N-oxide Cularirnine • Cularine • Cularine N-oxide Cyclanoline a-Cyclanoline t p.cyclanoline Danguyelline I D asymachaline Dauricoside · Decumbenine · Decumbenine-C Decumbensine · epi~-Decurnbensine ~lucopterocereine · Deglucopterocerelne

361 281 281 134 99 60 99 99 311 178 179

l

~ l C

N-oxide

146 233 307 233 334 167 167 168 82 154 158 65 349 353 350 351 363 366 366 128 128 128 377 305 63 335 334 340 340 372 372

8


Dehassiline 1,2-Dehydroanhalarnine 1,2-Dehydroanhalidinium quat 1,2-Dehydroanhalonidine Dehvdroanonaine Dehydroboldine Dehydrocapaurimine Dehydrocavidine Dehydrocheilanthifoline Dehydrocorybulbine Dehydrocorydaline Dehydrocorydalmine Dehydrocorydine Dehydrocorypalline Dehydrocorytenchine Dehydrocrebanine Dehydrodicentrine Dehydrodiscretamine Dehydrodiscretine Dehydroformouregine Dehydroglaucentrine Dehydroglaucine Dehydroguattescine 1,2-Dehydroheliarnine 1,2,3,4-Dehydroheliamine Dehydroisoboldine 3,4-Dehydroisocorydione Dehydroisocorypalmine Dehydroisolaureline Dehydroisothebaine 1,2-Dehydrolemaireocereine Dehydrolirinidine Dehydronantenine Dehydroneolitsine 6,6a-Dehydronorglaucine 6,6a-Dehydronorlaureline Dehydronomuciferine 1,2-Dehydronortehuanine 1,2-Dehydronorweberine Dehydronuciferine Dehydroocopodine Dehydroocoteine

108 430 432 433 247 67 437 230 81 79

221 203 146

88 196 281 302 70

76 396 146 216 271 161 161 127 238 143 268

95 370

92 227 312 206 277 169 391

455 171 323 417

9

Trivial Name Index

1,2-Dehydropach ycereine 1,2,3,4-D ehy dropach ycereine 1,2-Dehydropellotinium quat Dehydrophanostenine Dehydrophoebine Dehydropredicentrine Dehydropseud och eilanthifo line Dehydroremerine a-Dehydroreticuline Dehydroroemerine 1,2-Dehydrosalso lidine Dehydrostephalagine Dehydrostephanine Dehydrostesakine Dehydrothalicmine Dehydrothalicsimidine Dehydroxylopine Dehydroxyushinsunine Delporphine 6-O-Demeth yladlumi dine 6-O-Demethyladlumine N -D em et hy l am ur in e 8-Dem ethy largemonine Demethylcoclaurine N -D em eth yl c ol le tine 1Q-O-Demethylcoryd ine 3'-0-Demeth ylcularine 1Q-O-Demethyldiscretine n-0-Demeth y ldiscretine Demethyleneberberine N -D em eth y lf um ar itin e 0-7' -Dem ethy 1-l3-hydrastine 9-O-Dem ethy limeluteine N -D em et hy li so c or yt ub er in e N -D em et hyl lino fe rine 04-Demethy lmurarnine 3'-Demethylpa paverine 7-Demethylpapaverine N -D em eth y lste ph ala gi ne 3-0-Demethy lthalicthuberine 2-Demethylthalimonine 9-Demethylthalimonine

456 457 435 293 40 6 78

154 250 114

250 164

409 260 280 417 40 2 267

248 378 160 86

153 147, 203

47 10 5 137 360 71 66

50 157 335 393 134 20 1 200

190 140 40 9 84

237, 423 84, 423

10

The Simple Plant Isoquinolines 10-Demethylxylopinine 203 Densiberine 217 Deoxythalidastine 267 7-0-Desmethylisosalsolidine 90 Desmethylnarcotine 446 O-Desmethylweberine 455 N,O-Diacetyl-3-hydroxynornuciferine 375 N,O-Diacetylisopiline 386 N,O-Diacetylnoroliveroline 257 Dicentrine 301 Dicentrinone 306 Didehydroaporheine 250 Didehydroocoteine 417 Didehydroglaucine 216 Didehydroroemerine 250 5,6-Dihydroconstrictosine 42 Dihydrocoptisine 309 5,6-Dihydro-3,5-di-O-methylconstrictosine 43 Dihydroguattescine 271 Dihydroimenine 397 8,9-Dihydroisoroemerialinone 202 Dihydro1inaresine 322 Dihydromelosmine 387 1,2-Dihydro-6,7-methylenedioxy-l-oxoisoquinoline 333 3,4-Dihydro-l-methyl-5,6,7-trimethoxyisoquinoline 392 3,4-Dihydronigellimine 164 8,14-Dihydronorsa1utaridine 110 Dihydronudaurine 155 Dihydroorientalinone 135 11,12-Dihydroorientalinone 135 ~-Dihydropallidine 124 Dihydropalmatine 209 Dihydroparfumi dine 165 Dihydrorugosinone 322 8,14-Dihydrosa1utaridine 119 Dihydrosecoquettamine 357 4,6-Dihydroxy-3-methoxymorphinandien-7-one 49 4,6-Dihydroxy-2-methyltetrahydroisoquinoline 41 3,9-Dihydroxynornuciferine 376 5,6-Dimethoxy-2,2-dimethyl-l-(4-hydroxybenzy1)-I,2,3,4THIQquat 46 6,8-Dimethoxy-l,3-dimethylisoquinoline 348 6,7-Dimethoxy-N,N-dimethyl-l-(2-methoxy-4-hydroxybenzy1)-THIQ 188

11

Trivial Name Index

1,2-Dirnethoxy-ll-hydroxyaporphine 1,2-Dirnethoxy-3-hydroxynora porp hine 1,2-Dirnethoxy-3-hydroxy-5-oxonora porphine 2,9-Dimethoxy-3- hydroxypa vinane 6,7-Dirnethoxy-l-(6',7 -methy 1enedioxyisobenzofurano1, 3'-y 1)2,2-dimethy1-1,2,3,4- THIQ 6,7-Dimethoxy-l-(3,4-meth y 1enedioxypheny 1)-2-methy 1-DHIQ 6,7-Dimethoxy-l-(3,4-methy 1enedioxypheny 1)-2-methy 1-IQ 6,7-Dirnethoxy-l-( 4-methoxybenzy l)-IQ 6,8-Dirnethoxy-l-methyl-3- hydroxymethy lisoquinoline 6,7-Dimethoxy- 2-met hy lisocarbostyril 6,7-Dirnethoxy- N -meth ylisoquinoline 6,7-Dirnethoxy-2-methylisoquinolium quat N, o- Dimeth y1act ino da p hn ine N, o-D im eth y1arm epa vin e 0,o-Dimethy1bo1dine N, o- Dimeth ylc ass yfilin e 0,0- Dimethylcissamine 3,5-Di-O-methylconstrictosine O,o-Dimeth ylcorytuberine N, o- Dimeth y lcroto nosin e N, o-D im eth y lcrots parin e O,o-Dimeth ylcyclanoline N, o-D im eth y1hemo vin e 0,0- Dimethy1isobo1dine N, o-D im eth y 1is ocory din e N, N-Dime thy llind carpin e O,N-Dimethy lliriodendronine 0,0- Dim ethyllongifo1onine 0,0' -Dimethy1magnoflorine 0,o-Dimethy1munitagine N, o-D im eth y1nandige rin e N, o-D im eth y1ore oli ne N, o-D im eth y1ori din e N, N-Dime thy 1p avi niu m quat N, o- Di me thy 1th aicanine Dinorargemonine Disco1orine Discretamine Discretine Discoguattine Domesticine

175 373 373 44,106 244 168 16 8 184 348 240 240 162 301 185 214 323 218 43

212 17 9 17 9 218 76

21 4 21 8 68 93

186 218 212,371 300 18 0 18 0 218 403 71,122 48 70 76

320 155

12


Domestine Doryafranine Doryanine Doryfornine Doryphornine Doryphornine methyl ether Duguespixine Duguetine Duguevanine Duguexine Duguexine N-oxide Dysoxyline Egenine Elmerrillicine Enneaphylline Epiberberine Epiglaufidine 10-Epilitsericine 6-Epioreobeiline 14-Episinomenine Episteporphine Escholamidine Escholamine Escholidine Escholine Escholinine (also see under Romneine) Eschscholtzidine Eschscholtzidine methiodide Eschscholtzine Eschscholtzine N-oxide Eschscholtzinone Eximine Evoeuropine a-Fagarine Filiformine Fissiceine Fissicesine Fissicesine N-oxide Fissilandione Fissisaine Fissistigine A Fissistigine B

226 279 334

160 160 240

58 305 419 264 264 239 340 411 360 225 145 274

124 66 249 293 312 293 129 303 225,301 228,304 311 311 317

301 178 327

416 28 9

183 183 326 37 8 318 34 8

13

Trivial Name Index

Fissistigine C Fissoldine FK -3000

Flavinantine Flavinine Floripavidine Floripavine Formouregine N-F or m ylanh alam in e N-F or m ylanh al in in e N-F or m ylanh al on id in e N-F or m ylanh al on in e N-F orm yl an on aine N -F or m yl bu xi fo line 7-Formyldeh ydro hernanergine N -F or m yl de hyd ro no rn ucifer in e 7-Formyldeh ydrothalicsimidine N -F or m yl du gu ev an in e N -F or m yl her na ng er in e N-F or m yl-0-m eth ylan halon id in e N-F orm yl nom an teni ne N-F orm yl nor nu cifer in e N -F or m yl ov iger in e N -F or m yl pu rp ur eine N -F or m yl pu te rine N -F or m yl step har in e N -F or m yl xy lo pin e Fugapavine Fumaflorine Fumaflorine methyl ester Fumaramidine Fumaramine Fumaricine Fumaridine Fumariline Fumarine ~ Fumaritine ~ Fumaritine N-oxide [" Fumariz'me Fumarophycinol Fumschleicherine Fuzitine

J

I i

147 318 42 5 138 134 56

118 395 43 0 44 0 43 6 44 5 251 41 3 290 173 40 5 42 0 294 44 2 229 173 314 40 4 269 181 269 275 236 236 243 346 165 339 283 329 108 108 324 108 346 189

14


Gandhararnine Gentryamine A Gentryamine B Gigantine Gindarine Glaucentrine Glaucine Glaucine methine Glaucine methiodide Glaucinone Glaufidine Glaufine Glaufinine Glaunidine Glaunine Glauvent Glauvine Glaziovine Gnoscapine Gorchacoine Gortschakoine Goudotianine Gouregine Govadine Govanine Groenlandicine Guacolidine Guacoline Guadiscidine Guadiscine Guadiscoline Guatterine Guatterine N-oxide Guattescidine Guattescine Guattouregidine Guattouregine GusanlungA GusanlungB GusanlungC GusanlungD n-Hainanine

182 348 347 373 207 143 214 219 219 222 145 63

201 152 199 214 152 102 45 2 358 358 376 45 5 137 146 81

318 320 265 273 320 41 0 41 0 265 271 387 388 285 297 44

248 79

Trivial Name Index Heliamine Hemiargyrine Henderine Hernagine Hernandia base Hernandia base II Hernandia base IV Hernandia base VIII Hernandonine Hernangerine Hernovine (also see under Hexahydrofugapavine Hexahydromecambrine Hexahydrothalicminine Higenamine ~-Homochelidonine Homolaudanosine Homolinearisine Homomoschatoline Humosine-A Hunnemanine Hydrastidine Hydrastine a-Hydrastine I}-Hydrastine

161 122

446 201 290 290 306 292 316 290 Ovigerine)

Hydrastinimide Hydrastinine Hydrocotarnine Hydrohydrastinine 4-Hydroxyanonaine 4-Hydroxybulbocapnine 4-Hydroxycrebanine 7-Hydroxydehydroglaucine 3-Hydroxy-6a,7 -deh y dronuciferine 8-Hydroxydehydroroemerine 4-Hydro xy dicentrine 4-Hydroxyeschschol tzi dine 3-Hydroxyglaucine N-Hydroxyhernangerine 4 1 } - Hydroxyisocory dine 2'-Hydroxylaudanosine lO-Hydroxyliriodenine

15

69 276 276

41 5 47 327 239

61 396

340 289 335 336 337 336 339 333

44 7 245 247 287 281 222 374 259 302 235,382 380 294 194

234 277

16


1o-Hydroxymagnocurarine 13~-Hydroxy-N-rnethylstylopine quat Hydroxynantenine 3-Hydroxynantenine 4-Hydroxynantenine 3-Hydroxynornantenine 4-Hydroxynornantenine 3-Hydroxynornuciferine N-Hydroxynorthalicthuberine 3-Hydroxynuciferine N-Hydroxyovigerine 8-Hydroxypseudocoptisine 4-Hydroxysarcocapnidine 4-Hydroxysarcocapnine 8-Hydroxystephenanthrine 8-Hydroxystephenanthrine N-oxide 13~-Hydroxystylopine 3-Hydroxy-2,9,10-trirnethoxytetrahydroprotoberberine 4-Hydroxywilsonirine Hyndarin Hypecournine Irneluteine Irnenine Intebrirnine Intebrine Isoanhalarnine Isoanhalidine Isoanhalonidine Isoapocavidine Isoauturnnaline Isobackebergine Isoboldine Isocalycinine Isocanadine Isococlaurine Isocoptisine Isocorexirnine Isocorybulbine Isocorydine Isocorydine N-oxide Isocorydione Isocoryne

105 318 230 381 224 380 224 373 227 374 314 311 360 365 259 259 316

74 140 207 334 393 397 163 334 427 427 427 84

86 370 124 318 300

59 311

66 150 192 194 238 336

Trivial Name Index Isocorypalline Isocorypalmine Isocorypalmine N-oxide Isocorytuberine Isocularine Isodomesticine Isofugapavine Isoguattouregidine Isohydrastidine Isolaureline Isolaureline N-oxide Isomoschatoline Isonorargemonine Isonorteh uanine Isonorweberine Isooconovine Isoorien talinone Isopachycereine Isopacodine Isopellotine Isopiline Isopycnarrhine Isoquinoline Isoremerine Isoroemerialinone Isosalsolidine Isosalsolidine N-oxide Isosalsoline Isosalutaridine Isoscoulerine Isosendaverine Isosevanine Isosinoacutine Isotembetarine Isothebaidine Isothebaine Isouvariopsine Isovelucryptine Izmirine laculadine [acularine Jatrorrhizine

17 52 141 142 137 364

83 276 384 335

268 268 375 77, 194

391 456

389 135 457

73 428 385

52 39 248

201 164 164

90 123

65 52 284 137 361 94

95 279

62 87

60 99 75

18

The Simple Plant Isoquinolines [uziphine [uziphine N-oxide Juzirine Karnaline Kikernanine Kuafurnine Kukoline Laetanine Laetine Larnbertine Lanuginosine Lastourvilline Latericine Laudane Laudanidine Laudanine Laudanosine Laudanosoline Lauforrnine Launobine Laureline Laurelliptine Laurepukine Laurifoline Lauroli tsine Lauroscholtzine Laurotetanine Lauterine Ledeborine Ledecorine Lernaireocereine Leonticine Leucoline Leucoxine Leucoxylonine Leucoxylonine N-oxide Lirnousarnine Linaresine Lincangenine Lindcarpine Linearisine Liridinine

355 356 10 0 57 20 2 414

65 69

80 30 3 273

50 10 2 191 191 191 20 7 49 274 284 279 111 263 132 64 195 190 279 157 323 370 35 7 39 321 421 421 35 1 322 379 64 61 38 3

19

Trivial Name Index

Liridine Lirinidine Lirinine Lirinine N-oxide Liriodendronine Liriodenine Lirioferine Liriotulipiferine Litsedine Litseferine Litsericine Litsoeine Longifolidine Longifolonine

Longimammamine Longimammatine Longimammidine Longimammosine Lophocereine Lophocerine Lophophorine Lophotine salt Lotusine Luteanine Luteidine Luxandrine Lysicamine Machigline Machiline Madeyine Macrantaldehyde Macrantaline Macrantoridine Magnococline Magnocurarine Magnoflorine Magnoporphine Majarine Manibacanine Marshaline Mecambridine Mecambrine

396 92

374 374

47 25 7 20 4 72

295 29 0 27 4 19 0 370 100 45 42

45 41

91 91 444 444

62 192 15 9 49

17 0 289 97

329 45 1 449 449 358

10 4 12 9 218 297 175 32 4 45 0 275

20


Mecambroline Melosmidine Melosmine Menisperine Mescalotam a-N -Methopapaverberbine Methoxyatherosperminine Methoxyatherosperminine N -oxide I-Methoxyberberine 10-Methoxycaaverine 3-Methoxyglaucine 3-Methoxyguattescidine Methoxyhydrastine 10-Methoxyliriodenine Il-Methoxyliriodenine 3-Methoxynordomesticine 3-Methoxynuciferine 3-Methoxyoxoputerine 13-Methoxy-8-oxyberberine 4-Methoxypalmatine Methoxypolysignine 3-Methoxyputerine 8-Methoxyuvariopsine N-Methylactinodaphnine N-Methyladlumine 3-Methylallocryptopine O-Methylanhalidine N-Methylanhalidine quat O-Methylanhalonidine N- Methylanhalonidine a-8-Methylanibacanine N-Methylanolobine O-Methylanolobine N-Methylanonaine N -Methylapocrotsparine N -Methylarmepavine o-Methylarmepavine O-Methylarmepavine N-oxide N-Methylasimilobine N -Methylasimilobine-2-0-~-D-glucopyranoside N-Methylasimilobine-2-o-a-L-rhamnopyranoside O-Methylatheroline

276

399

387 197 442 448 395 395

447 105 402 412 452 279 27 3 390 395 414 305 403 217

412 282

287 242 328 440 432 441 434

94 263 266 248 103 181 185 185 55 55 561 220

Trivial N arne Index N- Me thy lbo ldine Q-Methylbracteoline N- Me thy lbulb ocapnine Q-Methylbulbocapnine a-Q-Methylbulbocapnine N-oxide ~O-Methylbulbocapnine N-oxide N- Me thylb ux ifo lin e N- Me thylc ali fom ine N- Me thylc aly cin ine Q-Methy1calycinine N- Me thylc anadine Q-Methy1capaurine Q-Methylcaryachine N- Me thylcar yachinium qu at N- Me thylcas syfil ine Q-Methylcassyfiline N- Me thylcas sythine Q-Methylcassythine N- Me thy lch eil anthifo lin e qu at Q-Methylcinnamolaurine N- Me thy lco cla uri ne Q-7-Methy1coclaurine 13-Methylcolumbarnine 3-Q-Methy1constrictosine N- Me thylc ore ximi ne Q-Methy1corledine N- Me thylc ory daldine N- Me thy1 coryd ali ne qu at N- Me thylc ory dalrn ine qu at N- Me thylc ory dine Q-Methy1corydine Q-Methy1corydine Nsoxide N- Me thylc ory palli ne Q-Methylcorypalline l-Methylcorypalline 2-Methylcorypallinium N- Meth ylcoryp alrnine ll-Methylcorytuberine N- Meth ylcro ton osine N- Meth ylcro tsp ari ne N- Meth ylcro tsp ari nine N- Meth ylcry chine

21

68 149

28 8 30 0 30 0 30 0 41 3 31 4 319

32 0 30 3 44 2 225,301 83,288 41 5 41 6 415 41 6 83 279

10 0 176

15 1 43

13 2 24 1

23 9 22 1 20 4 15 1 21 2 21 2

89 16 2

90

89 79

14 3 61

10 2 10 3 31 4

22

The Simple Plant Isoquinolines O-Methylcularicine N-Methylcularine N-Methyldanguyelline O-Methyldehydroisopiline N-Methyldihydroberberine quat 0-Methyl-8,9-dihydroisoorientalinone O-Methyldihydrosecoquettamine O-Methyldomesticine N-Methyldomesticinium N-Methylduguevanine N-Methylelmerrillicine O-Methylelmerrillicine 6,7-Methylendioxy-1-<4-methoxybenzyD-IQ 6,7-Methylendioxy-1-<4-methoxybenzyD- THIQ 6,7-Methylendioxy-l-t 4-methoxy-a-hydroxybenzyD-3,4-DHIQ 2,3-Methylenedioxy-4,8,9-trimethoxy-N-methylpavinane N-Methyl-10-epilitsericine N-Methylescholtzine 0- Methylflavinantine N-Methylfissoldine 7-Methyl-N-formyldehydroanonaine O-Methylfumarophycine O-Methylfumarophycinol N-Methylglaucine N-Methylheliamine N-Methylhernangerine N-Methylhernangerine /3-N-oxide N-Methylhernovine 10-0-Methylhernovine N-Methylhigenamine N-Methylhigenamine, 7-O-~-D-glucopyranoside N-Methylhigenamine N-oxide N-Methylhydrasteine N-Methylhydrasteine imide N-Methylhydrastine N-Methyl-~-hydrastine quat O-Methylisoboldine N -Methylisococlaurine N-Methylisocorydine N-Methylisocorypalmine quat O-Methylisomoschatoline O-Methylisoorientalinone

368 361 377 394 304 202 358 155 156 420 411 412 278 277 278 235,416 276 314 147 319 252 165 165 219 162 292 292 71

73 48 48 48

338 339 338 337 149

60 197 151 396 201

23

Trivial Name Index 394 385

0-Methylisopiline N-Methylisopiline N-Methylisosalsoline 1-0-Methylisothebaidine N-Methylisothebaine N-Methylisothebainium cation 0-Methylisovelucryptine N-Methyllaudanidinium iodide N-Methyllauformine N-Methyllaunobine N-Methyllaurelliptine 9-0-Methylla urolitsine N-Methyllaurotetanine N-Methyllaurotetanine N-oxide O-Methylledecorine N-Methyllindcarpine 0-Methyllirinine N-Methyllitsericine N-Methyllophophorine quat N-Methylmecambridine 2-Methyl-1-(4-methoxybenzyD6,7-methylenedioxyisoquinolinium N-Methyl-10-G-methylhernovine O-Methylmoschatoline N-Methylnandigerine N-Methylnandigerine ~-N-oxide N-Methylnantenine N-Methyl-a-narcotine O-Methylnarcotoline N-Methylneocaryachine quat D-Methylnorarmepa vine 9-0-Methylnorboldine 8-O-Methyloblongine N-Methyloreophiline salt D-Methylorientalinone N-Methylovigerine N-Methyloxoh ydrasteine D-Methyloxopukateine N-Methylpachycereine N-Methylpachypodanthine N-Methylpachypodanthine N-oxide N-Methylpalaudium quat

90 175

96 96 189 197 276 286 124

73 195 196 324

66 395 276 444 450 quat

278 76 396 292 292 228 454 452 288,369 184

73 371 450 201 310 339 273 457 256 256 197

24


O-Methylpallidine O-Methylpallidine N-oxide O-Methylpallidinine 13-Methylpalmatine N-Methylpapaveraldine N-Methylpapaverine quat N-Methylpavine O-Methylpellotine N-Methylpellotine quat 0-Methylpeyomvic acid 0-Methylpeyoxylic acid 0- Methylplatycerine N-Methylplatycerinium quat 0-Methylprechilenine 0-Methylpreocoteine 0-Methyl przewalskiinone 8a- Methylpseudoanibacanine 8~-Methylpseudoanibacanine N -Methylpseudolaudanine 0-Methylpukateine N-Methylputerine N-Methylsecoglaucine 0-Methylseverzine N-Methylsinactine N-Methylsparsiflorine N-Methylstenantherine N-Methylstepharine 0-Methylstepharinosine N-Methylstylopinium quat a-N-Methylstylopinium quat ~-N-Methylstylopinium quat N-Methyltetrahydrocolumbamine 1-Methyl-1,2,3,4-tetrahydroisoquinoline N-Methyltetrahydropalmatine N- Methyltetrahydropapaverine N-Methylthaicanine 0-Methylthaicanine N- Methylthalbaicaline 0-Methylthalicmidine N-Methylthalidaldine 0-Methylthalisopavine N-Methyl-2,3,6-trimethoxymorphinandien-7

147 149 149 221 220 217 213 442 435

441 441 212,371 197,367 332 402 220 94 94 78

267 267 219 241 228 103 398 179 187 313 313 313 151

39

-one N-oxide

218 207 380 402 380 214 408 214 149

25

Trivial Name Index

N-Methylushinsunine G-Methylvelucryptine N-Methylviguine N-Methylxylopine N-Methylxylopine N-oxide N-Methylzenkerine Michelalbine Michelanugine Micheline A Micheline B Michepressine Miltanthaline Milthanthine Mocrispatine Mollinedine Moschatoline Munitagine Muramine Nandazurine Nandigerine Nandinine Nantenine Narceimine Narceine Narceine imide Narceinone Narcosine Narcotine a-Narcotine p-Narcotine Narcotinediol Narcotine hemiacetal Narcotoline Narcotolinol Narlumicine Narlurnidine Neocaryachine Neolitsine Nigellimine Nigellimine N-oxide Nokoensine Noramurine

255 18 6 245 268 26 8 106

253 270

254 257 276 43 6 179 50

307

383 117, 362 22 2 156 290 285 226 345 45 4 45 4 45 4 45 2 45 2 45 2 45 3 45 1 45 2 44 6 44 6 345 345 286, 368 312 164 164 43 7 15 3


26 Noranicanine Norannuradhapurine Norargemonine Norarmepavine N-Norarmepavine Noratherosperminine Norboldine Norbracteoline Norbulbocapnine N orcanelilline Norcarnegine Norcinnamolaurine Norcoclaurine Norcorydine Norcorypalline Norcularicine Norcularidine Nordelporphine Nordicentrine N ordomesticine Norfissilandione Norfumaritine Norglaucine N orgorchacoine Norguattevaline Norimeluteine Norisoboldine Norisocorydine N orisocorydione N orisocorytuberine Norisocularine Norisodomesticine Norjusiphine Norjuziphine N-Norlaudanosine Norlaureline Norleucoxylonine Norliridinine Norlirioferine Nornantenine N ornarceine Norneolitsine

174 280 147, 203 176 176 171 64

134 284 93 163 274 47 139 88 352 350 377 295 153 325 157 206 358 376 393 11 1

189 237 134 363 80 354 354 205 277 42 1 383 201 223 45 3 307

27

Trivial Name Index

Nomuciferidine Nomuciferine Nomuciferine I O-Nomuciferine Noroconovine N oroliveridine Noroliverine Noroliveroline N ororientaline Nororientinine Noroxyhydrastinine Norpachyconfine Norpachystaudine Norpallidine Norphoebine Norpredicentrine Norpreocoteine Norprotosinomenine Norpurpureine Norreframidine Norreticuline Norrufescine Norsalutaridine Norsarcocapnine Norsarcocapnidine Norsecocularidine Norsecocularine Norsecosarcocapnidine Norsecosarcocapnine Norsinoacutine Norsonodione Norstephalagine Norstephanine Nortehuanine Northalicmine Northalicthuberine Northalifoline Norushinsunine Noruvariopsarnine Norweberine Noryuziphine Noscapalin

173 169 92

55

40 0 270 272 253 133 95

332 58

256 111 40 5 73 389 63 40 1 307 109

392 11 0 363 359

351 366 360 364 110 237 409

260 391

41 6 227 159

253 186

45 5 354 45 2

28


Noscapine u-Noscapine Noscopine hemiacetal Nuciferidine Nuciferin Nuciferine Nuciferoline Nudaurine Nummularine Oblongine Obovanine Ochotensidine Ochotensimine Ochotensine Ocobotrine Ocokryptine Ocominarine Ocominarone Oconovine Ocopodine Ocoteine Ocotominarine Ocoxylonine Oduocine Oliveridine • Oliveridine N-oxide Oliverine Oliverine N-oxide Oliveroline Oliveroline P-N-oxide Ophiocarpine Ophiocarpinone Opian Opianine Oreobeiline Oreoline Oreophiline Oridine Orientaline Orientalinone Orientidine Orientine

45 2 45 2 45 2 174 170 170 181 155 53 356

262 327 238 87

120 42 3 325 42 2 40 1 323 41 7 42 2 42 0 41 8 270 270 272 272 254 254 305 306 45 2 45 2 124 99 45 0 99 135 135 183 184

29

Trivial Name Index

Orientinine Oureguattidine Ovigerine Oxoanolobine Oxoasimilobine 7-oxobaicaline 8-oxoberberrubine Oxobuxifoline 8-0xocanadine Oxocompostelline 8-0xocoptisine Oxocrebanine 13-0xocryptopine Oxocularidine Oxocularicine Oxocularine 7-0xodehydroasimilobine Oxodicentrine Oxoduocine Oxoglaucine Oxohydrastinine Oxoisocalycinine 8-0xoisocorypalmine Oxolaureline Oxolaurenine ' Oxo-N -methylhydrasteine 13-0xomuramine Oxonantenine Oxonuciferine Oxophoebine 8-0xopolyalthiaine 13-0xoprotopine Oxopukateine Oxopurpureine Oxoputerine Oxosarcocapnidine Oxosarcocapnine Oxosarcophylline Oxostephanine Oxostephanosine 8-0xotetrahydropalmatine 8-0xotetrahydrothalifendine

96

386 306 266 58

42 5 285 414 297 369 310 283 233 352 353 368 58 306 419 220 333 319 142 279 279 339 223 231 170

407 158 331 266

404 273 362 367 352 261 259 209 291

30


8-0xothaicanine Oxoushinsunine Oxoxylopine Oxyberberine N-Oxycodamine 8-0xycoptisine Oxydehydrocorybulbine N-Oxyduguexine N-Oxyguatterine Oxyhydrastinine N-Oxyoliveridine Oxynarcotine N-Oxypachyconfine Oxypalmatine 13-0xyprotopine N-Oxyspixianine 8-0xythalifendine Pachycereine Pachyconfine Pachyconfine N-oxide Pachypodanthine Pachystaudine Pacodine Palaudine Pallidine Pallidinine' Palma tine Palmatrubine Pancoridine Pancorinine Papaveraldine Papaveraldinium quat Papaverine Papaveroxidine Papaveroxine Papaveroxinoline Papracine Papracinine Paprafumine Papraine Papraline Parfumidine

379 257 273 299 141 310

80 264

410

333 270 453 59 211 331 319 292 456

59 59

256 257 140 190 123 124 210 192 140 140 219 220

206 452 451 451 339 107

346 51 245

166

31

Trivial Name Index

Parfumine Pavine Pectenine Pellotine Peruvianine Peshawarine Pessoine Petaline Petaline methine Peyoglutam Peyophorine Peyorovic acid Peyotine quat Peyotline Peyoxylic acid Phanostenine Phellodendrine Phoebe base Phoebe base II Phoebine Phyllocryptine Phyllocryptonine Pilocereine Platycerine Polyalthine Polyberbine Polycarpine Polygospermine Polysignine Polysuavine Prechilenine Predicentrine Preocoteine Preocoteine N-oxide Prepseudopalmanine Proaporphine Promucosine Pronuciferine Protopine Protosinomenine Protothalipine Pseudoanibacanine

107

205 164 43 4 176

345 109 358 357

43 8 44 5 43 4 43 5 43 4 43 4 293 132 66 62

40 6 288 289 240 192, 365 41 3 321 235 40 5 186 265 329 77

389 389 223 40

182 179

329 65 200 94

32

The Simple Plant Isoquinolin Isoquinolines es

Pseudoberberine Pseudocheilanthifoline Pseudocolumbamine Pseudocoptisine Pseudojatrorrhizine Pseudolaudanine Pseudomanibacanine Pseudopalmatine Pseudoprotopine Pseudorine Pseudoronine Psilopine Pterocereine Pukateine Pulchine Purpureine Puterine Pycnarrhine Quettamine Raddeanamine Raddeanidine Raddeanine Raddeanone Refractamide Reframidine Reframine Reframine Reframine methiodide methiodide Reframoline Rehybrine Remerin Remerine Remerine Remerine N-oxide N-oxide Remeroline Remrefidine Remrefine Reticuline Reticuline Reticuline N-oxide N-oxide Rhopalotine Roefractine Roehybrine Roemecarine Roemecarine Roemecarine N-oxide N-oxide

300 15 4 14 6 3 11 76

73 175

21 3 3 31 78 78

41 1 372

2 63 10 6 402

2 66

88 357

23 2 23 2 23 1 23 2 3 07 3 11 22 6 22 8 83 13 5 2 48 2 48 249

2 63 250 22 8 11 1 1 14 1 45 62

1 35 74 74

33

Trivia Triviall Name Name Index Index

n-Roemehybrine Roemeramine Roemerialinone Roemerine Roemer Roemerine ine N -oxide -oxide Roemerolidine Roemeroline Roemrefidine Roemrefine Rogersine Romnei Romneine ne (also (also see see under under Escholi Escholinin nine) e) Romucosine Romuco Romucosine sine G Romuco Romucosine sine H Rotundine Rufescine Rugosinone Rurrebanidine Rurrebanine Sal Salsolidine Salsoline Salsolinol Salutaridine Salutaridine Salutaridine N-oxide N-oxide Salutarine Sanjoinine Sanjoinine Ia Sanjoinine Sanjoinine Ib Sanjoinine Sanjoinine E Sanjoinine K Sarcocapnidine Sarcocapnid Sarcocapnidine ine N-oxide N-oxide Sarcocapnine cis-Sarcoca cis-Sarcocapinine pinine N-oxide N-oxide Sarcophylline Sauvagnine Saxoguattine Schefferine Scoulerine Sebiferine Secocularidine Secocularine

136 2 75 201 2 48 2 49 2 64 2 63 250 228 195 295 252 40 4 199 71, 122, 207 393 322 3 75 396

47 1 63

52 47 118 119 118 1 69 1 89 1 70 97

359 3 60 3 64 3 64 350 323 200 202 114 1 47 351 3 67

34


Secoglaucine Secophoebine Secoquettamine Secosarcocapnine Secosarcocapnidine Secoxanthoplanine Sendaverine Sendaverine Sendaverine N-oxide N-oxide Setigeridine Setigerine Sevanine Severzine Sewerzine Siamine SiaminineA Siamin Siaminine ine B Sibiricine Sinactine Sinacutine Sinoacutine Sinococuline Sinomendine Sinomenine Sonodione Sparsiflorine Spermatheridine Spiduxine Spinosine Spixianine Spixianine Spixianine N-oxide N-oxide Splendaboline Splendidine Srilankine Stenantherine Stephabinamine Stephabine Stephadiolamine 1 3 - N-oxide N-oxide Stephalagine Stephanine Stepharanine Stepharine Stepharinosine

217 40 6 3 57 3 67 36 1 198 89 89 231 222 153 1 60 1 60 3 47 3 47 3 47 317 2 24 118 118 42 6 41

65 238 100 257 236 1 88 319 319 398 17 4 78

3 98 43 6 43 8 25 5 40 9 2 60 136 1 77 1 87

35

Trivial Name Index

Stephenanthrine Stephenanthrine N-oxide Stephodeline Stepholidine Steporphine Stesakine Stesakine-9-0-l3- D-glucopyranoside Stipitatine Stylophylline Stylopine Suavedol Suaveoline Subsessiline Sukhodianine Sukhodianine-~-N-oxide Takatonine Tannagine Taxilamine Tehuanine Tehuanine N-oxide Telazoline Teliglazine Telikovine Telitoxine Tembetarine Tepenine Tetradehydrocapaurine Tetradehydrocheilanthifoline Tetradehydroscoulerine Tetrahydroberberine Tetrahydroberberrubine Tetrahydrocolumbarnine Tetrahydrocoptisine Tetrahydrocorysarnine Tetrahydrojatrorrhizine Tetrahydropalmatine Tetrahydropalmatrubine Tetrahydropapaverine Tetrahydroprotoberberine Tetrahydropseudoberberine Tetrahydrosinacutine Tetrahydrostephabine

251 251 429

136 249 280 280 372 337 307 102 188 398 282 282 400 429 234 391 392 92

38 6 174

167 127 371 437 81 117

296 285 141 307 315

74 207 191 205

40 300 120 438

36


Thaicanine Thailandine Thaipetaline Thalactamine Thalbaicalidine Thalbaicaline Thalflavine Thalicmidine Thalicmidine methine Thalicmidine N-oxide Thalicmine Thalicminine Thalicsimidine Thalicpureine Thalicthuberine Thalicthuberine N-oxide Thalictricavine Thalictricine Thalictrimine Thalictrine Thalictrisine Thalictuberine Thalidastine Thalidicine Thalidine Thalifaurine Thalifendine Thalifendlerine Thalifoline Thalihazine Thalimicrinone Thalimonine Thalimonine N-oxide Thaliporphine Thaliporphine methine Thalisopavine Thalisopynine Thaliphendine Thalphenine Thalprzewalskiinone Trichoguattine Triclisine

379 261 378 40 8 380 379 42 5 149 152 150 41 7 41 8 40 2 40 3 228 229 304 294 327 129 294 228 291 138 123 82

291 399 160 40 7 40 0 237, 424 237, 424 149 152 194 40 1 291 159 200 252 166

Trivial Name Index Tridictyophylline 3,10,11-Trihydroxy-l,2-methylenedioxynoraporphine Trilobinine 2,3,7-Trimethoxy-8,9-methylenedioxy-N 5,6,7-Trimethoxy-N-methylisoquinolinium 1,2,11-Trimethoxy-6a-noraporphine 2,3,6-Trimethoxy-N -normorphinandien-7 1,2,3-Trimethoxy-5-oxonoraporphine N,O,O- Trimethyllaurelliptine N,O,O- Trimethylsparsiflorine Tritopine Tuduranine Tuliferoline Turcamine Turcomanidine Turcomanine Uberine Umbellatin Ushinsunine Ushinsunine l3-N-oxide Uthongine Uvariopsamine Uvariopsamine N-oxide Uvariopsine Vaillantine Velucryptine Veronamine Viguine Weberidine Weberine Wilsonirine Worenine Xanthaline Xanthopetaline Xanthoplanine Xanthopuccine Xyloguyelline Xylopine Xylopinine Xylopinine N-oxide Yenhusomidine Yenhusomine

-methyl pavinane quat -one

37

438 382 158 235,416 392 183 139 394 214 185 191 178 396 354 188

10 9 46 297 254 254 283 187 187 268 51

10 6 399 245

44 456 139 316 219 292 198 296 384 266 212 213 234 234

38


Yuanhunine Yuzirine Yuziphine Zanoxyline Zanthoxyphylline Zenkerine Zijinlongine Zippelianine Zizyphusine

205 100 355 185 184 105 449 428 51

Structural Index - Unsubstituted

UNSUBSTITUTED ISOQUINOLINES

Isoquinoline Leucoline 2-Benzazine

Cistanche salsa (Orobanchaceae) yh 8, 522 '88 Nico tian a tab acu m cv (Solanaceae) abc 41, 377 '77 Papaver somniferum (Papaveraceae) abf 21, 201 '84 Spigelia anthelmia (Loganiaceae) pm 52, 378 '86

OQH I-Methy l-l,2,3,4-tetrah y droisoq uinoline

Pachycereus weberi (Cactaceae) ac 57, 109 '85

\ benzyl

H

IQ

I I-Benzylisoquinoline

Thalictrum spp. (Ranunculaceae)

yfz 10,72 '90

39

40


benzyl Me THIQ

8,8a-Secoberbine Not a natural product. syn 9, 887 '92

I with a (2,N-Me) attack: I Tetrahydroprotoberberine Berbine

Be rbe ris beaniana (Berberidaceae) tl25, 951 '84 Fumaria officina lis (Papaveraceae) abs 4

4-HO-benzyl Me THIQ

Compound unknown

I with a (1,8) attack: I Proaporphine Phoebe formosan a (Lauraceae) pptp 27, 65 '93

41

Structural Index - Monosubstituted

5-SUBSTITUTED

lSOQUINOLINES

Compound

5-MeO 2,3-MeO ,MeO-u,u- M e,HO-benzyl

H

I with

unknown

IQ

a (6,8) attack:

I Sinomendine

Sinomenium acutum (Menispermaceae) jnp 57, 1033 '94

6-SUBSTITUTED

6-HO H Me

ISOQUINOLINES

H 0 Y i( l THIQ

~NCH3 Longimammosine

Dolichothele longimamm a

I with a 4-hydroxy

group:

(Cactaceae)

joe 41,319 '76

OH

I HO~

4,6-Dihydroxy-2methyltetrahydroisoquinoline

Theobroma cacao (Sterculiaceae)

llyd 41, 130 '78

~~CH3

42


6-HO 4-HO-benzyl, HO Me THIQ

Compound unknown

HO

with a (2,N-Me) attack and loss of hydrogen:

5,6-Dihydroconstrictosine Ar ist ol oc hia co nstri cta (Aristoloehiaeeae) aa 13, 737 '83

I with a 3,4-ene: I

OH

HO

Constrictosine

Ar ist ol oc hia co ns tri cta (Aristolochiaceae) aa 13, 737 '83

Longimammatine

6-MeO H

H

THIQ

D olicho thele lo ng im am ma (Cactaceae) joe 41, 319 '76 D olich ot he le ub erifor mi s (Cactaceae) joe 41, 319 '76

OH


6-MeO 4-HO-benzyl, HO Me THIQ

43

Not a natural product. tet 37, 3175 '81

with a (2,N-Me) attack, loss of hydrogen, and a 3,4-ene:

3-0-Methylconstrictosine

OH Ar istolo chia con stricta (Aristolochiaceae)

6-MeO 4-MeO-benzyl, HO Me THIQ

aa 13, 737 '83

Not a natural product. joc 44, 3730 '79

with a (2,N-Me) attack and loss of hydrogen:

5,6-Dihydro-3,5-di-O-meth ylconstrictosine Aristolo chia const ric ta (Aristolochiaceae)

aa 13, 737 '83

I and a 3,4-ene: I 3,5-Di-O-methylconstrictosine

Ar istolo chia const ric ta (Aristolochiaceae)

aa 13, 737 '83


44

7-SUBSTITUTED ISOQUINOLINES

7-HO 4-HO-benzyl H THIQ

Compound unknown

with a 1,2 seco, with an N-carbomethoxy:

HO

Gusanlung

C

Arc ang elisia gusanlu ng (Menispermaceae) phy 39, 439 '95

Weberidine

7-MeO H

H

THIQ

Pachycereus weberi (Cactaceae) ac 57, 109 '85

7-MeO 3,4-MeO,HO-benzyl Me THIQ

Compound unknown

I with a (6,3) attack: I 2,9-Dimethoxy-3-hydroxypavinane

CH30 Arg emone mun ita (Papaveraceae)

joe 38, 3701 '73

also under: 6,7 MeO HO R Me THIQ R= 4-MeO-benzyl (2,3) attack

45


8-SUBSTITUTED ISOQUINOLINES

8-HO H Me

Longimammidine ~NCH3

THIQ

OH

D olicho the le lon gim am ma (Cactaeeae) joe 41, 319 '76 D olicho thele ube rif orm is (Cactaeeae) llyd 40, 173 '77 Theobroma cacao (Sterculiaceae) llyd 41, 130 '78 OH

I with a 4-hydroxy group: I

q)

NCH3

Longimammamine

D olicho thele longim am ma (Cactaeeae) joe 41, 319 '76 D olicho the le ube riform is (Cactaeeae) llyd 40, 173 '77

OH

46


5,6-DISUBSTI 5,6-DISUBSTITUTED TUTED

ISOQUINOLINE ISOQUINOLINES S

5-Me 5-MeO O 6-Me 6-MeO O 4-HO-benzyl Me,M Me,Me+ e+ THIQ THIQ

5,6-D 5,6-Dime imetho thoxyxy-2,2 2,2-di -dimet methyl hyl-l-( -l-(4-h 4-hydr ydroxy oxyben benzy1 zy1)-l )-l,2, ,2,3,4 3,4- De smos smo s yunna yu nna nensis ne nsis

(Annon (Annonace aceae) ae)

tcyyk tcyyk 12, 1 '00


5-Me 5-MeO O


Uberine

7-HO 7-HO

H

Me

THIQ

Do lich othe le ube rifo rmis

(Cacta (Cactacea ceae) e) jnp 40, 173 173 '77


None found in plants

ISOQUINOLIN ISOQUINOLINES ES

THIQ quat quat

47

Structural Structural Index - 6,7-HO,HO 6,7-HO,HO-Subst -Substituted ituted

6,7-DIHYDRO 6,7-DIHYDROXYSUB XYSUBSTITUTE STITUTED D

Salsolinol Sal

6-HO 6-HO 7-HO 7-HO Me H THIQ


H 0 :G Q ~

HO

I

S NH

CH3 Aco nitum nitu m car mic hae li (Ranun (Ranuncul culace aceae) ae) yx 17, 17, 792 '82 (Musaceae eae)) jafc jafc 24, 24, 189 189 '76 M usa paradis par adis iaca iac a (Musac (Sterculiaceae) ceae) jafc 24, 900 '76 Theobroma cacao (Sterculia

6-HO 6-HO 7-HO 7-HO a-keto-benzyl H IQ

Compou Compound nd unknow unknown n

HO

I with with a (2,8) (2,8) attack attack:: I

Liriodendronine HO

Liriod Li riod endron end ron tulipife tuli pife ra (Magnoliaceae) phy 16, 2015 '77

6-HO 6-HO 7-HO 7-HO 4-HQ-benzyl H THIQ

Higenamine N orcoc1aurine Demethylcoc1aurine

HO HO

HO

Aconit Ac onit um Aconit Ac onitum um Aco nitum nitu m Aco nitu m

(Ranuncul culace aceae) ae) kjp 29, 129 '98 car mic hae lii (Ranun (Ranun (Ra nuncul culace aceae) ae) jnp 44, 44, 53 '81 japoni jap onicum cum (Ranuncul culace aceae) ae) kjp 29, 129 '98 korea ko rea num (Ranun (Ranuncul culace aceae) ae) kjp 29, 129 '98 kusne ku sne zof fii (Ranun


48

Ac onitu m nap iforme ifor me (Ranunc (Ranuncula ulacea ceae) e) kjp 29,129 29,129 '98 Annon An non a reticu ret iculata lata (Annona (Annonacea ceae) e) tl28, tl28, 1251 1251 '87 Annon An non a squamo squ amo sa (Annon (Annonace aceae) ae) jnp 44, 44, 53 '81 Asiasar Asi asar um heter he terotro otropoi poides des (Aristo (Aristoloc lochia hiacea ceae) e) cpb 26, 26, 2284 2284 '78 (Aristolochiaceae) ceae) cpj 44, 211 '92 Asiasar Asi asar um sieb oldii oldi i (Aristolochia (Rutacea ceae) e) book book 1 Euodia rutaecarpa rutaecarpa (Ruta (Gnetacea ceae) e) jnp 62, 1025 1025 '99 Gnetum parvifoliu parvifolium m (Gneta (Nymphae haeace aceae) ae) cpb 18,256 18,2564 4 '70 Ne lumbo lum bo nucife nu cife ra (Nymp

HO

6-HO 7-HO 4-HO-benzyl Me THIQ

(d1)-N-Methylhigenamine

Gnetum parvifoliu parvifolium m

(Gneta (Gnetacea ceae) e) jnp 62, 1025 1025 '99

HO

HO

I the N-oxide: I (-)-N-Me (-)-N-Methy thylhi lhigen genami amine ne Gnetum parvifoli parvifolium um

N-Oxid N-Oxidee

(Gneta (Gnetacea ceae) e) jnp 62, 1025 1025 '99

with a (1,8) attack, attack, and and redu reduct ctio ion n of a dou doubl blee bond bond and and of the carbo carbonyl nyl group group in the the benzyl benzyl ring: ring:

HO

Discolorine

HO Croton discolor discolor (Euphor (Euphorbia biacea ceae) e)

(Euphorbi rbiace aceae) ae) Croton plumieri plumieri (Eupho

rlq 1, 140 '70 rlq 1, 140 '70

glucoside de at the the 7-0H positio position: n: I I the glucosi N- Methylhigenamine, 7-0-[3- D-glucopyranoside (Rutaceae) e) phy 35,209 35,209 '94 Phellodendron Phellodendron amurense (Rutacea

49

Structural Index - 6,7-HO,HO-Substituted

HO

6-HO 7-HO 4-MeO-benzyl Me,Me+ THIQ

Luxandrine

HO

Pseudoxandra sclerocarpa (Annonaceae)

HO

6-HO 7-HO 3,4-HO,HO-benzyl Me THIQ

Papaver somniferum

phy 25,2693 '86

Laudanosoline

HO

(Papaveraceae)

book 4

HO OH

6-HO 7-HO 3,4-HO,MeD-benzyl H THIQ

Compound unknown

I with a (2,4a)attack: I 4,6-Dihydroxy-3-methoxymorphinandien-7-one

Croton bonplandianus (Euphorbiaceae) phy 20, 683 '81

o


50

Compound unknown

6-HO 7-HO 3,4-HO,MeO-benzyl Me THIQ

I with a (2,4a) attack: I

Mocrispatine

Mo nod ora crispata (Annonaceae)

aua 17, 105 '81

o 6-HO 7-HO 3,4-MeO,MeO-benzyl Me THIQ

Tetrahydroprotopapaverine Not a natural product. jcspt 2, 1696 '80

with a (2,N-Me) attack and aromatization of the c-ring:

HO HO

Demethyleneberberine Stephania venosa (Menispermaceae) zh 30, 250 '99 Thalictrum javanicum (Ranunculaceae) jnp 46, 454 '83

I with a (6,8) attack: I Lastourvilline Artabotrys lastourv illensis (Annonaceae) jnp 48, 460 '85 Fumaria indica (Papaveraceae)

phy 31, 2869 '92 Glaucium leiocarpum (Papaveraceae) pm 65, 492 '99

OC H 3

OCH3

Structural Index - 6,7-HO,HO-Substituted

6-HO 7-HO 3,4-MeO,MeO-benzyl Me,Me+ THIQ

Compound unknown

I with a (2,8) attack I Zizyphusine Na ndina dom estica (Berberidaceae) nmt 50, 427 '96 Ziz iphu s fru ctus (Rhamnaceae) apr10,208'87 Ziz iphu s juj uba (Rhamnaceae) apr 12,263'89 Ziz iphu s spinosa (Rhamnaceae) kjp 16,44 '85

HO

6-HO 7-HO 6',7'-MOO-isobenzofuranone, 3'-yl Me THIQ

HO

Papraine Fumaria indica (Papaveraceae)

het 29,1091 '89

6-HO 7-HO 3,4-MeO,MeO-benzyl, HO Me,Me+ THIQ

I with a (2,N-Me) attack I Vaillantine Fumaria vaillantii

(Papaveraceae)

Compound unknown

HO

HO

kps 476 '74

Theassigned structure of this compound has been challenged:jnp 45,241 '82

51


52

6,7-HO-MeO-ISOQUINOLINES

6-HO

Isocorypalline

7-MeO

H

Me

THIQ

(Berberidaceae) e) cnc 11,563 '75 B erbe er be ris ri s ob lo ng a (Berberidacea (Papaveraceae) kps 19, 19,461 461'83 '83 Corydalis stricta stricta (Papaveraceae) (Menisperrnac errnaceae) eae) nrn 52, 541'98 541'98 Stephania Stephania cepharantha cepharantha (Menisp

6-HO

HOm

Isopycnarrhine

7-MeO

H

Me+

I. :::: :::::: ::.. .... ...

DHIQ

/: +NCH a

CHaO

(Annonaceae) eae) jnp 49,102 49,1028 8 '86 Popowia pisocarpa pisocarpa (Annonac

6-HO

HOm

7-MeO

H

4-M 4-MeO-b eO-ben enzy zyll

CHaO CHaO

THIQ THIQ

I. :::: :::::: ::.. .... ...

N

Isosendaverine (Papav avera eracea ceae) e) phy 36, 36, 241'94 Corydalis sp. (Pap (Papaveraceae)) phy 36, 36, 241'94 241'94 Ceratocapnos Ceratocapnos heterocarpa heterocarpa (Papaveraceae

6-HO Me H

7-MeO THIQ

Salsoline

OCHa

H 0 x :Q

CHaO::::::"'"

(Alangia giacea ceae) e) prns prns 5 '80 Al an gi um la ma rck rc k ii (Alan (Chenopodiace diaceae) ae) app 34, 421'77 421'77 Corispermum Corispermum leptopyrum leptopyrum (Chenopo (Fabaceae eae)) phy 12,19 12, 193'73 3'73 D es mo dium di um til ia ef ol iu m (Fabac

I

S NH

CHa

Structural Structural Index - 6,7-HO,M 6,7-HO,MeO-Sub eO-Substitute stituted d

(Cactacea ceae) e) jps 58, 1413 1413 '69 Echinocereus merkerii (Cacta (Fabaceae) ae) nr Genista purgens (Fabace Pachycereus pecten-aboriginum pecten-aboriginum (Cacta (Cactacea ceae) e) aps 15, 127 '78 (Chenopod podiac iaceae eae)) ber 67, 878 '34 Salsola arbuscula (Cheno (Chenopod podiac iaceae eae)) book book 6 Salsola kali (Cheno (Chenopodia diacea ceae) e) iant iant 2, 86 '85 Salsola pestifera (Chenopo (Chenopodia diacea ceae) e) rr 16, 86 '80 Salsola richteri (Chenopo

6-HO 7-MeO Me 3,43,4-HO HO,Me ,MeOO-be benz nzyl yl

THIQ THIQ

Numm Nummular ularine ine Be rbe ris numm nu mm ula ria

(Berbe (Berberid ridace aceae) ae)

6-HO 7-Me -MeO Me 3,4-Me 3,4-MeO,M O,MeOeO-ben benzyl zyl

cnc 33,70 33,70 '97

THIQ

Bemumicine Be rbe ris num mu laria lar ia

6-HO 7-MeO Me 3,43,4-MD MDOO-be benz nzyl yl


kps 3, 397 '93

THIQ THIQ

Bemumine Be rbe ris nu mm ula ria


kps 3, 394 '93

53


54

6-HO benzyl H

7-MeO

Not a natural product. joc 49,581 '84

THIQ

I with a (2,8) attack: attack: I

HO

(-)-Asimilobine

CH30 spp. (Annona (Annonacea ceae) e) pm 41, 48 '81 (Annonace aceae) ae) jccs jccs 44, 44, 313 '97 An no na ch erim er im ol ia (Annon (Annonace aceae) ae) cpj 46, 439 '94 An no na sq ua mo sa (Annon spp. (Annonace (Annonaceae) ae) fit 65,87 65,87 '94 An no na spp. (Annonaceae eae)) bs&e bs&e 26, 139 '98 An om ia nt hu s spp. (Annonac spp. (Annon (Annonace aceae) ae) jbas jbas 15,59 15,59 '91 Ar ta bo try s spp. spp. (Annon (Annonace aceae) ae) yz 85, 85, 77'65 77'65 As im ina in a spp. (Annonace aceae) ae) jccs jccs 46, 46, 607 '99 '99 Cananga odorata odorata (Annon spp. (Annon (Annonace aceae) ae) pm 57, 581 '91 Cardiopetalum spp. spp. (Annona (Annonacea ceae) e) pm 50,5 50,517' 17'84 84 Cymbopetalum spp. spp. (Annon (Annonace aceae) ae) jnp 45, 45, 617'82 617'82 D esm es m os spp. spp. (Annon (Annonace aceae) ae) phy 29, 3845 3845 '90 D ise pa lu m spp. spp. (Anno (Annona nace ceae ae)) abs abs 3 Fissistigma spp. (Monimiac iaceae eae)) jnp 48, 833 '85 Glossocalyx spp. (Monim spp. (Ann (Annon onac acea eae) e) abs abs 3 Goniothalamus spp. spp. (Annon (Annonace aceae) ae) jnp 46, 46, 335 '83 Guatteria spp. spp. (Annon (Annonace aceae) ae) lac 1982,1 1982,1623 623'82 '82 He x al ob us spp. (Monimiac iaceae eae)) phy 21, 773 '82 Lau L au relia re lia ph ili pp ia na (Monim (Magnoliac iaceae eae)) cnc 13, 602 '77 Liri L iri od en dr on spp. (Magnol (Magnoliacea ceae) e) phy 23, 188 '84 M ag no lia spp. (Magnolia (Annonaceae eae)) phy 26, 537 '87 M eiog ei og yn e spp. (Annonac spp. (Annon (Annonace aceae) ae) ajc 24, 2187 2187 '71 M elod el od or um spp. spp. (Annonace (Annonaceae) ae) jnp 54, 1331'9 1331'91 1 M on oc yc la nt hu s spp. (Nymphaeace aceae) ae) jnp 50, 50, 773 '87 N elum el um bo spp. (Nymphae (Lauracea ceae) e) fes 30, 30, 479 '75 Ocotea spp. (Laura spp. (Annon (Annonace aceae) ae) pmp 20, 251'86 251'86 Oncodostigma spp. (Annonace aceae) ae) bs&e bs&e 27, 111'99 111'99 Orophea spp. (Annon (Lauracea ceae) e) jccs jccs 40, 40, 209 '93 Phoebe spp. (Laura (Annonace aceae) ae) jbas jbas 16, 99 '92 Polyalthi Polyalthiaa suberosa suberosa (Annon (Annonace aceae) ae) jnp 49, 1028 1028 '86 Popowia spp. (Annon (Annonaceae) ae) jnp 49,102 49,1028 8 '86 Ro lli nia ni a spp. (Annonace

An ax ag or ea

Structural Structural Index - 6,7-HO,Me 6,7-HO,MeO-Subst O-Substituted ituted

spp. (Moni (Monimia miacea ceae) e) pm 59,10 59,100 0 '93 Siparuna spp. spp. (Meni (Menispe sperma rmacea ceae) e) yhhp yhhp 21, 223 '86 Stephania spp. spp. (Mag (Magnol noliac iaceae eae)) apf 43, 189 189 '85 Talauma spp. spp. (Anno (Annonac naceae eae)) nm 51, 272 '97 Uvaria spp. spp. (Ann (Annona onacea ceae) e) pmp 16,25 16,253 3 '82 Xy lopia spp. Ziziphus spp. spp. (Rhamna (Rhamnacea ceae) e) pjsr pjsr 3D, 81 '78

I glucoside at the 6-HO position: I (-)-Asimilo (-)-Asimilobinebine- 2-0-/3-D-gI ucoside ucoside (Menisperm ermace aceae) ae) Stephania Stephania pierrei pierrei (Menisp

6-HO -HO

7-MeO MeO

benzyl

Me

jnp 56, 1468 '93

Not a natural product. jhc 4, 417 417 '67

THlQ

(2,8)attack: I I with a (2,8)attack:

HO

N-Methylasimilobine O-Nomuciferine (Annonace aceae) ae) jccs jccs 44, 313 '97 Ann ona cherimo che rimolia lia (Annon spp. (Ann (Annona onacea ceae) e) phy 49, 2015 2015 '98 Ann ona spp. spp. (Rha (Rhamna mnacea ceae) e) pm 27, 304 '75 Colubrina spp. spp. (Anno (Annonac naceae eae)) jnp 50, 664 '87 Dugu D uguetia etia spp. (Annonace aceae) ae) jnp 54, 54, 1331 1331 '91 Mono M onocycla cycla nthu s spp. (Annon spp. (Nymph (Nymphaea aeacea ceae) e) jps 66, 66, 1627 1627 '77 Ne lumbo lumb o spp. (Annonace aceae) ae) phy 3D, 1265 1265 '91 Oxymitra spp. (Annon (Papavera eracea ceae) e) dsa 7, 93 '83 Papaver spp. (Papav (Menisp isperm ermace aceae) ae) jnp 63, 477 'DO Stephania cepharantha (Men spp. (Anno (Annonac naceae eae)) jnp 44, 551 '81 Xy lopia spp. Ziziphus spp. spp. (Rha (Rhamna mnacea ceae) e) apr 12, 263 '89

I glucosideat the 6-HO position: I (·)·N-Methylasimilobine-2-0-~-D-glucopyranoside (Menispe isperma rmacea ceae) e) Stephania cepharantha (Men

jnp 63, 477 'DO

55


56

I rhamnoside at the 6-HO position: I N-Methylasimilobine-2-0-a-

Floripavidine L-rhamnopyranoside

Papaver armeniacum (Papaveraceae) dsa 7, 93 '83 Papaver fugax (Papaveraceae) dsa 7, 93 '83 Papaver tauricolum (Papaveraceae) dsa 7, 93 '83

6-HO 7-MeO benzyl Me,Me+ THIQ

Compound unknown

HO

with a (2,8) attack and a 1,2 seco:

Argentinine Annon a mon tana (Annonaceae) pnsc 3, 63 '79 Aristolochia arg entina (Aristolochiaceae) aaqa 60, 309 '72 Enantia chlorantha (Annonaceae) pm 9, 296 '75 Guatteria discolor (Annonaceae) jnp 47, 353 '84 Guatteria foliosa (Annonaceae) jnp 57, 890 '94 Guatteria goudotiana (Annonaceae) phy 30, 2781 '91 Monocyclan thus vignei (Annonaceae) jnp 57, 1033 '94 Phaeanthus vietnam ens is (Annonaceae) fit 62, 315 '91 Popowia pisocarpa (Annonaceae) jnp 49,1028 '86

I the N-oxide: I Argentinine Mo noc yclanthus

N-Oxide

vignei (Annonaceae)

jnp 57, 1033 '94

Structural Index - 6,7-HO,MeO-Substituted

6-HO ben zyl Ac

7-MeO

Compound unknown

THIQ

I with a (2/8) attack I

(-)-N- Acetylasimilobine Lir iodendron tulip ifer a (Magnoliaceae) phy 15/ 547 '76 Zanthoxylum simulan s (Rutaceae) phy 36/ 237 /94

6-HO 7-MeO ben zyl CONH2 THIQ

Compound unknown

HO

I with a (2/8)attack I N-Carbamoylasimilobine

CH30

Hexalobus cris piflorus (Annonaceae) jnp 46/ 761/83

6-HO ben zyl C02 Et

7-MeO

Compound unknown

THIQ

witha (2/8)attack, glucosideat the 6-HO position: Kamaline Stephania venosa (Menispermaceae) phy 36/1053/94

Glu-O

CH30

57

58


6-HO 7-MeO a-keto-benzyl H IQ

I with

Compound unknown

a (2,8) attack: I

HO

Oxoasimilobine 7-0xodehydroasimilobine Annon a cherimolia (Annonaceae) jccs 46, 77 '99 Da symaschalon rostra tum (Annonaceae) zzz 26, 39 '01 Monocyclan thus vig nei (Annonaceae) jnp 57, 1033 '94

6-HO 7-MeO a-Me-benzyl CHO THIQ

Compound unknown

HO

with a (2,8) attack and an a,l-ene:

Duguespixine Du guetia spix iana (Annonaceae) jnp 51, 389 '88 Guatteria sagotiana (Annonaceae) jnp 51, 389 '88

6-HO 7-MeO a-HO-benzyl H THIQ

I with

Compound unknown

a (2,8) attack: I

Norpachyconfine Du guetia spix iana (Annonaceae) jnp 50, 664 '87


HO (-)-Anaxagoreine Ana xagor ea sp. (Annonaceae)

pm 41,48 '81

Cananga odorata (Annonaceae)

6-HO 7-MeO a-HO-benzyl Me THIQ

CH30

jccs 46, 607 '99

Compound unknown

HO I with a (2,8) attack: I

Pachyconfine D uguetia spixia na (Annonaceae) jnp 50, 664 '87 Guatteria sagotiana (Annonaceae) jnp 49, 1078 '86 Pachypodanthium confine (Annonaceae) apf 35, 65 '77

I the N-oxide: I N-Oxypachyconfine Pachyconfine N-oxide D uguetia spix iana

6-HO 7-MeO 4-HO-benzyl H THIQ

D esm os yun nanens is

(Annonaceae)

jnp 50, 664 '87

(+)-Isocodaurine

(Annonaceae)

tcyyk 12, 1 '00

59


60

HO

I with a (1,8) attack: I Crotonosine

CH30 Croton Croton Croton Croton

cumingii (Euphorbiaceae) llyd 32, 1 '69 discolor (Euphorbiaceae) llyd 32, 1 '69 linearis (Euphorbiaceae) llyd 32, 1 '69 plumieri (Euphorbiaceae) phy 8, 777 '69

and reduction of the 2,3 double bond and of the carbonyl group in the benzyl ring:

0

HO CH30

jaculadine

Croton discolor (Euphorbiaceae) Croton plumieri (Euphorbiaceae)

rlq 1, 140 '70

HO

rlq 1, 140 '70

HO

I with a (2,8) attack: I Apocrotonosine

Croton sp. (Euphorbiaceae)

CH30

jnp 38, 275 '75

HO

6-HO 7-MeO 4-HO-benzyl Me THIQ

N-Methylisococlaurine

(+ )-isomer:

De smoe yunna nensis

(Annonaceae)

tcyyk 12,1 '00


(-)-isomer: Phoebe minutiflora

(Lauraceae) cpj 49, 217 '97

isomernot specified: Ne lumbo nucifera (Nymphaeaceae)

phy 12, 699 '73

HO

I with a (l,8) attack: I N-Methylcrotonosine

(-)-isomer: Croton discolor (Euphorbiaceae)

rlq 1, 140 '70

Croton plumieri (Euphorbiaceae)

phy 8,777 '69 Mecon opsis camb rica (Papaveraceae) jnp 44,67 '81 Papaver triniaefolium (Papaveraceae) pm 63, 575 '97

o

isomernot specified: Ano mian thus dulcis (Annonaceae) bs&e 26, 139 '98 Croton cumingii (Euphorbiaceae) llyd 32, 1 '69 Croton linearis (Euphorbiaceae) llyd 32, 1 '69 Orophea hexandra (Annonaceae) bs&e 27, 111'99 Papaver fugax (Papaveraceae) pm 41, 105 '81

Theearliest isolation of this base from the Croton species (pes 261 '64) wasa mixture of alkaloids that was given the name Homolinearisine. Subsequentpurification showed it to be N-Methylcrotonosine (jcs 1676 '66).

HO

and reduction of a double bond in the benzyl ring: Linearisine Croton discolor (Euphorbiaceae)

rlq 1, 140 '70 Croton linearis (Euphorbiaceae) llyd 32,1 '69 Croton plumieri (Euphorbiaceae) phy 8,777 '69

0

61


62

6-HO 7-MeO 4-HO-benzyl Me,Me+ THIQ

HO

Lotusine

CHsO

N elum bo nu cife ra (Nymphaeaceae) zzz 16, 673 '91 Tiliacora racemosa (Menispermaceae) jics 57, 773 '80

6-HO 7-MeO 4-MeO-benzyl Me THIQ

HO

HO

(+)-Roefractine

CHsO

Ro em er ia re frac ta (Papaveraceae) jnp 53, 666 '90

CHsO HO

I with a (2,8) attack: I Phoebe base II

CHsO

Phoebe sp. (Lauraceae) jnp 38, 275 '75

CHsO

6-HO 7-MeO 4-MeO-a-keto-benzyl H DHIQ

Isovelucryptine

Cryptocarya velutinosa (Lauraceae) jnp 52, 516 '89

63


6-HO

7-MeO

Compound

unknown

3,4-HO,HO-benzyl Me THIQ HO

I with a (2,8) attack: I

Glaufine CHsO HO

Glaucium fimbrilligerum (Papaveraceae) kps 4, 493 '83

HO

I with a (6,N-Me)

attack:

HO

I

(-)-Artavenustine

CHsO

Artab otrys ve nus tus (Annonaceae) jn p 49, 602 '86 OH

and a glucoside on the 3-HO of the original benzyl group:

Dauricoside M enisperm um dau ric um

(Menispermaceae)

cpb 41, 1866 '93

HO

6-HO 7-MeO 3,4-HO,MeQ-benzyl

H

THIQ

CHsO HO

(+)- Norprotosinomenine

Erythrina lithosperma

(Fabaceae)

ajc 24, 2733 '71

64


I with a (2,8) attack I

HO

Lindcarpine

He rn an di a vo yr on ii (Hernandiaceae) pm64,58'98 Ill ig er a pe nt ap hy lla (Hernandiaceae) jnp 48, 835 '85 Lin de ra pi pe ric ar pa (Lauraceae) het 9, 903 '78 Lin de ra reflex a (Lauraceae) cty 25, 565 '94 Lits ea ac um in at a (Lauraceae) cpj 46, 299 '94 Phoebe grandis (Lauraceae) phy 45, 1543 '97 Stephania sp. (Menispermaceae) jnp 38, 275 '75

I with a (6,8) attack I

HO

Laurolitsine Norboldine Cryptocarya longifolia (Lauraceae) ajc 34, 195 '81 D eh aa sia kur zi i (Lauraceae) fit 62,261 '91 Ill ig era pe nt ap hy lla (Hernandiaceae) jnp 48, 835 '85 Lin de ra re flex a (Lauraceae) cty 25,565 '94 Lits ea ro tu nd ifol ia (Lauraceae) ryz 8,324 '00 L its ea spp. (Lauraceae) pm 48, 52 '83 M ac hi lu s du th ei (Lauraceae) jcp 2, 157 '80 M on im ia ro iu nd iio lia (Monimiaceae) apf 38,537 '80 N ec ta nd ra saliciiolia (Lauraceae) jnp 59, 576 '96 N eo lit sea au ra ta (Lauraceae) jccs 22, 349 '75 N eo lit sea bu isan en sis (Lauraceae) jccs 22, 349 '75 Peumus boldus (Monimiaceae) phy 32, 897 '93 Phoebe clemensii (Lauraceae) jnp 46,913 '83 Phoebe formosana (Lauraceae) jnp 46,913 '83 Phoebe grandis (Lauraceae) phy 45,1543 '97 Phoebe minutiflora (Lauraceae) cpj 49, 217 '97 Re ta ni lla ep he dr a (Rhamnaceae) rlq 5, 158 '74

OH

65


HO

6-HO 7-MeO 3,4-HO,MeQ-benzyl Me THIQ

CHsO

Protosinomenine Erythrina lithosperma (Fabaceae) CHsO ajc24, 2733 '71 Li tse a glu tino sa (Lauraceae) jcspt I, 1477 '88 Polyalthia nitidissima (Annonaceae) pm 49, 20 '83 Stephania cepharantha (Menispermaceae) cpb 45, 470 '97

I with a (2,N-Me) attack: I

OH

HO

Isoscoulerine

CHsO (-)-isomer: Corydalis ambigua (Papaveraceae) daib 45, 2160 '85

OH

OCHs isomer not specified: Stephania hainanensis (Menispermaceae)


the l,8a trans isomer: Sinomenine Cucoline Kukoline Stephania cepharantha (Menispermaceae) cpb 45, 470 '97 Stephania epigaea (Menispermaceae) nyx 5, 203 '85 Stephania micrantha (Menispermaceae) nyx 7,13 '87

cty 18, 146 '87

CHsO HO

o OC H s

66


the 1,8a cis isomer:

CHsO

14-Episinomenine

HO

Ocotea brachybotra (Lauraceae) fes 32, 767 '77 Stephania cepharantha (Menispermaceae) cpb 45, 470 '97

o OC H s


HO

N-Methyllindcarpine Phoebe base

CHsO HO

De haa sia triandr a (Lauraceae) CHsO tet 52, 6561 '96 Glaucium paucilobum (Papaveraceae) jsiri 10, 229 '99 Glaucium spp. (Papaveraceae) jnp 61, 1564 '98 Illig era pentap hylla (Hernandiaceae) jnp 48, 835 '85 Litsea cubeb a (Lauraceae) jccs 39, 453 '92 Magn olia acu min ata (Magnoliaceae) daib 32, 2312 '71 Menispe rmu m can ade nse (Menispermaceae) llyd 34, 292 '71 Phoebe clemensii (Lauraceae) jnp 46,913 '83 Strychnopsis thouarsii (Menispermaceae) pm 58, 540'92

I with

a (6,N-Me) attack:

I

HO CHsO

(S)(-)-Isocoreximine ll-O-Demethyldiscretine

OC H s Toddalia asiatica (Rutaceae) phy 48, 1377 '98 Xylopia vie illardi (Annonaceae) jnp 54,466 '91

OH



HO

Boldine

CHsO

Actinodaphne spp. (Lauraceae) ajc22, 2257 '69 CHsO Artabotrys lastouroillensis (Annonaceae) jnp 48, 460 '85 OH Cocculus spp. (Menispermaceae) jics 56, 1020 '79 Dehaasia kur zii (Lauraceae) fit 58, 430 '87 D esm os tieo aghiensis (Annonaceae) jnp 45, 617 '82 Hed ycarya angustif olia (Monimiaceae) het 26, 447 '87 Illigera pent aphy lla (Hernandiaceae) jnp 48, 835 '85 (Monimiaceae) hca 50, 1583 '67 Laurelia novae-zelandiae Laurus nobilis (Lauraceae) jnp 45, 560 '82 Lin dera spp. (Lauraceae) jnp 48, 160 '85 Litsea spp. (Lauraceae) cpj 46, 299 '94 M achi lus duihei (Lauraceae) jcp 2, 157 '80 M onim ia rotu ndifolia (Monimiaceae) apf 38, 537 '80 Ne ctandra gran diflora (Lauraceae) ijp 31, 189 '93 Ne olits ea spp. (Lauraceae) jccs 45, 103 '98 Peumus spp. (Monimiaceae) jc 612, 315 '93 Phoebegrand is (Lauraceae) phy 45,1543 '97 Polyalthia cauliflora var. beccarii (Annonaceae) jnp 47, 504 '84 Reta nilla ephedra (Rhamnaceae) rlq 5, 158 '74 Sassafras albidum (Lauraceae) llyd 39, 473a '76 Trivalvaria macrophylla (Annonaceae) jnp 53, 862 '90

HO

landan a,l-ene:1 Dehydroboldine

Peumus boldus (Monimiaceae) jnp 51,389 '88

CHsO

CHsO OH

67


68

Compound unknown

6-HO 7-MeO 3,4-HO,MeO-benzyl Me,Me+ THIQ

HO

I with a (2,8) attack: I N,N-Dimethyllindcarpine

Ar ist oloc hi a tri an gu la ris (Aristolochiaceae) jcps 6, 8 '97 Caltha leptosepala (Ranunculaceae) CHsO phy 16, 500 '77 Coscinium fenestratum (Menispermaceae) pm 38, 24 '80 M ag no lia spp. (Magnoliaceae) jnp 38, 275 '75

HO

I with a (6,8) attack: I N-Methylboldine Boldine methiodide

CHsO

Cocculus sp. (Menispermaceae) jnp 46, 761 '83

CHsO OH

Compound unknown

6-HO 7-MeO 3,4-HO,MeO-benzyl Ac THIQ

I with

a (6,8) attack:

HO

I

N-Acetyllaurolitsine Lits ea ro tu nd ifol ia (Lauraceae) ryz 8, 324 '00 Lits ea sp. (Lauraceae) ajc 22, 2259 '69

CHsO

CHsO OH

69


Not a natural product. jcspt I, 1531 '75

6-HO 7-MeO 3,4-MeO,HO-benzyl H THIQ

I with a (2,8) attack: I (+)-Hemovine

HO

Croton linearis (Euphorbiaceae) llyd 32, 1 '69 Croton wilsonii (Euphorbiaceae) rlq 1, 140 '70 HO He rna ndi a gui ane nsis (Hemandiaceae) pm 50, 20 '84 He rna ndi a nym pha eif olia (Hemandiaceae) pm 63,154 '97 He rna ndi a ovige ra (Hemandiaceae) apf 42,317 '84 Illi ger a luz one nsi s (Hemandiaceae) jnp 60, 645 '97 Illigera par vif lor a (Hemandiaceae) cty 22, 393 '91 Linde ra my rrh a (Lauraceae) phy 35, 1363 '94 Neolitsea va riabill ima (Lauraceae) het 9, 903 '78 Ocotea teleiandra (Lauraceae) rlq 23,18 '92

(Thename Hemovine is used as a synonym for Ovigerine. See pg. 306)

lwith a (6,8)attack: I

Laetanine

He rna ndia vo yro nii (Hernandiaceae) pm 64, 58 '98 Litse a lea ta (Lauraceae) phy 18, 910 '79 Ocotea teleiandra (Lauraceae) r lq 23, 18 '92

HO

HO OCHs

6-HO 7-MeO 3,4-MeO,HO-benzyl Me THIQ

Not a natural product. dmd 14,703 '86

70


I with a (2,N-Me) attack: I (S)(-)Discretamine Aequaline

HO

CHsO

An no na ch er im ol ia (Annonaceae) pmp 23, 159 '89 An no na re tic ul at a (Annonaceae) zzz 17,295 '92 An om ia nthu s du lcis (Annonaceae) bs&e 26,139 '98 Ar tabo trys ma in ga yi (Annonaceae) jnp 53, 503 '90 Ar tabo trys ve nu stu s (Annonaceae) jnp 49, 602 '86 D esmo s lo ng if loru s (Annonaceae) fit 66, 463 '95 D esmo s tie ba gh iens is (Annonaceae) jnp 45, 617 '82 D ug ue tia ca lycina (Annonaceae) pmp 12, 259 '78 Fissistigma glaucescens (Annonaceae) phy 24, 1829 '85 Fissistigma oldhamii (Annonaceae) abs 3 Goniothalamus amuyon (Annonaceae) abs 3 Guatteria discolor (Annonaceae) jnp 47, 353 '84 M eiog yn e vi rg at a (Annonaceae) phy 26, 537 '87 N an di na do me stica (Berberidaceae) phy 27, 2143 '88 Oncodostigma monosperma (Annonaceae) jnp 52, 273 '89 Polyalthia stenopetala (Annonaceae) phy 29, 3845 '90 Ro lli ni a lept op etal a (Annonaceae) pb138, 318 '00 Saccopetalum prolificum (Annonaceae) ccl Tl, 129 '00 Schefferomitra subaequalis (Annonaceae) joe 42, 3588 '77 Stephania intermedia (Menispermaceae) yhtp 16, 1 '85 Stephania succifera (Menispermaceae) zx 31, 544 '89 Uvaria lucida (Annonaceae) nm 51, 272 '97 X ylop ia bu xifol ia (Annonaceae) jnp 44, 551 '81 X ylop ia di sc re ta (Annonaceae) bull I

OH

HO

I and aromatization of the c-ring: I Dehydrodiscretamine

OCHs

CHsO OCHs

Fissistigma balansae (Annonaceae) phy 48, 367 '98 N an dina do me sti ca (Berberidaceae) phy 27, 2143 '88 Stephania intermedia (Menispermaceae) yhtp 16, 1'85 Thalictrum foliolosum (Ranunculaceae) daib 45, 520 '84 Tinospora capillipes (Menispermaceae) pm 50, 88 '84

OH



N-Methylhemovine

71

HO

Croton linearis (Euphorbiaceae) llyd 32,1 '69 Croton wilsonii (Euphorbiaceae) llyd 32,1 '69 OH Her nand ia guianens is (Hernandiaceae) pm 50, 20 '84 Her nand ia nym phae ifolia (Hernandiaceae) pm 63,154 '97 Hernan dia peltata (Hernandiaceae) pm 46, 119 '82 Lin dera meg aphy lla (Lauraceae) jn p 57, 689 '94 Lin dera oldhamii (Lauraceae) het 9, 903 '78 Ne olits ea var iabillima (Lauraceae) het 9, 903 '78 HO

I with a (6,N-Me) attack: I lO-O-Demethyldiscretine

Artabotrys venustus (Annonaceae) jnp 49, 602 '86 Caryomene olivascens (Menispermaceae) afb 6, 163 '87 Guatteria discolor (Annonaceae) jnp 47, 353 '84 Xylop ia vie illar di (Annonaceae) jnp 54, 466 '91

I with a (6,3)attack: I Bisnorargemonine Dinorargemonine Rotundine

HO

CHsO

Arg emo ne spp. (Papaveraceae) jnp 46,293 '83 Chasmanthera dependens (Menispermaceae) pm 49,17 '83 Cocculus laurifolius (Menispermaceae) tet 40, 1591 '84 Corydalis decumbens (Papaveraceae) jca 6691/2,225 '94 Cryptocarya longifolia (Lauraceae) jnp 46, 293 '83 Eschscholzia spp. (Papaveraceae) jn p 46,293 '83

OH

OC H s

OH

OCHs


72

Fumaria bastardii (Papaveraceae) nps 4, 257 '98 Thalictrum dasycarpum (Ranunculaceae) jnp 46, 293 '83

also under: 6,7 MeO HO R Me THIQ R= 3,4-HO,MeO-benzyl (6,3) attack

(The name Rotundine has been used for two unrelated alkaloids; the one in this section, and one which is a synonym for Tetrahydropalmatine. The literature shows that (-)-Rotundine (Tetrahydropalmatine) comes from Stephania sp., whereas this Rotundine comes from Argemone sp.)


HO

Liriotulipiferine Artabo trys lastourv illen sis (Annonaceae) jnp 48, 460 '85 Liriodend ron tulip ifer a (Magnoliaceae) HO jnp 42, 325 '79 Litsea cubeba (Lauraceae) jca 667, 322 '94 Strychnopsis thouarsii (Menispermaceae) pm 58, 540 '92

6-HO 7-MeO 3,4-MeO,HO-a- Me-benzyl Me THIQ


Compound unknown

HO

Corydalidzine

Corydalis caucasica (Papaveraceae) ijcd 27, 161 '89 Corydalis koidzumiana (Papaveraceae) cpb 23, 313 '75 Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89 Corydalis solida ssp. brachyloba (Papaveraceae) jcsp 13, 63 '91

OH


6-HO 7-MeO 3,4-MeO,MeO-benzyl H THIQ

Not a natural product. sh 17,49 '86

I with a (2,8) attack: I lO-O-Methylhernovine Croton wilsonii (Euphorbiaceae)

rlq 1, 140 '70

I with a (6,8) attack: I N orpredicentrine 9-0- Methyllaurolitsine 9-0-Methylnorboldine Guatteria scandens (Annonaceae) jnp46, 335 '83 He rna ndi a vo yro nii (Hemandiaceae) pm 64, 58'98

6-HO 7-MeO 3,4-MeO,MeO-benzyl H IQ

Papaver somniferum var. noordster (Papaveraceae) jcspt I, 1531 '75

6-HO 7-MeO 3,4-MeO,MeO-benzyl Me THIQ

HO

Isopacodine

(+)-Pseudolaudanine

Arcto me con me rriam i (Papaveraceae) bse 18,45 '90 Roem eria refra cta (Papaveraceae) jnp 53, 666 '90

CH30

HO

73


74

I and a

(+)-trans 4-hydroxy group:

I

Roemecarine Ro em eria ca ric a (Papaveraceae) het 24, 1227 '86 Ro em er ia re frac ta (Papaveraceae) jnp 53, 666 '90

I the N-oxide: I Roemecarine N-Oxide Ro em eria ca rica (Papaveraceae)

het 24, 1227 '86

I with a (2,N-Me) attack: I (-)-Corypaimine (+Tetrahydrojatrorrhizine 3-Hydroxy-2,9,lO-trimethoxytetrahydroprotoberberine An no na ch er im ol ia (Annonaceae) pmp 23,159 '89 Ar ge mo ne gr an di flor a (Papaveraceae) phy 11,461 '72 Ber be ris ju lia na e (Berberidaceae) cz 29, 265 '75 Coptis teeta (Ranunculaceae) ijcs 28, 97 '51 Corydalis lutea (Papaveraceae) phy 33, 943 '93 Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89 D ug ue tia ste lic ha nt ha (Annonaceae) rlq 16,107 '85 Enantia chlorantha (Annonaceae) pmp 9, 296 '75 Fibraurea chloroleuca (Menispermaceae) pw 113, 1153 '78 Glaucium grandiflorum (Papaveraceae) jnp 49,1166 '86 Guatteria discolor (Annonaceae) jnp 47, 353 '84 Hy dr as tis ca na de ns is (Ranunculaceae) gci 110, 539 '80 Pachypodanthium confine (Annonaceae) apf 35,65 '77 Pachypodanthium staudtii (Annonaceae) pw 113, 1153 '78 Ro lli ni a le pt op etal a (Annonaceae) pbI 38, 318 '00 Stephania mashanica (Menispermaceae) cty 14, 249 '83 Stephania micrantha (Menispermaceae) yhhp 16,557 '81

OH


Stephania succifera (Menispermaceae)

zx 31, 544 '89 Xylopia vieillardii (Annonaceae) jnp 54, 466 '91

land aromatization of the c-ring:

I

HO

J atrorrhizine

Arca ngelisia flava (Menispermaceae) jnp 45, 582 '82 Berberis erataegina (Berberidaceae) kps 106, '96 Ber beris spp. (Berberidaceae) jnp 58, 1100 '95 Burasaia australis (Menispermaceae) bse 19, 433 '91 Burasaia cong esta (Menispermaceae) bse 19, 433 '91 Burasaia grac ilis (Menispermaceae) bse 19, 433 '91 Chasmanthera dependens (Menispermaceae) pm 46, 228 '82 Coptis spp. (Ranunculaceae) phy 21,1419 '82 Corydalis spp. (Papaveraceae) jca 669 1/2, 225 '94 (Menispermaceae) pm 38, 24 '80 Coscinium fenestratum (Menispermaceae) phy 22, 1671 '83 Diosco reop hyllu m cumminsii Enantia chlorantha (Annonaceae) pmp 9, 296 '75 Fagara chalybea (Rutaceae) kdr 23, 153 '90 Fibraurea chloroleuca (Menispermaceae) pw 113, 1153 '78 Fibraurea recisa (Menispermaceae) ncyh 2, 77 '82 Glaucium arabicum (Papaveraceae) duj 17, 185 '90 Hydrastis cana densis (Ranunculaceae) sz 46, 42 '92 Ja trorrhiza palm ata (Menispermaceae) llyd 28, 73 '65 Je ffersonia dubia (Berberidaceae) pm 51,52 '85 Mahonia aquifoliu m (Berberidaceae) pm 61, 372 '95 Mahonia spp. (Berberidaceae) pm 57, 505 '91 Na ndina domestica (Berberidaceae) phy 27, 2143 '88 Penianthus zenkeri (Menispermaceae) phy 30,1957 '91 Phellodendron spp. (Rutaceae) pm 59,557 '93 Sphenocentrum jollyanum (Menispermaceae) phy 15, 2027 '76 Stephania glabra (Menispermaceae) jnp 45, 407 '82 Stephania intermedia (Menispermaceae) yhtp 16, 1'85 Stephania miyiensis (Menispermaceae) zh 30, 250 '99 Stephania viridiflavens (Menispermaceae) cty 12, 1 '81 Thalictrum spp. (Ranunculaceae) jnp 43, 372 '80 Tinospora spp. (Menispermaceae) pm 48, 275 '83 (Ranunculaceae) llyd 26, 254 '63 Xanthorhiza simplicissima Zantho xylum chalybeu m (Rutaceae) jnp 59, 316 '96

75

76



HO

N,O-Dimethylhernovine N-Methyl-lO-O-methylhernovine Croton linearis (Euphorbiaceae) llyd 32,1 '69 Croton wilsonii (Euphorbiaceae) rlq 1,140 '70

HO

I with a (6,N-Me) attack: I Discretine

Caryomene olivascens (Menispermaceae) afb 6,163 '87 Du guetia obovata (Annonaceae) jnp 46, 862 '83 Guatteria discolor (Annonaceae) jnp 46, 862 '83 Guatteria scandens (Annonaceae) jnp 46, 335 '83 Pachypodanthium staudtii (Annonaceae) pmp 11, 315 '77 Stephania suberosa (Menispermaceae) phy 26, 547 '87 Xylopia disc reta (Annonaceae) bull 1 Xylopia vieillar di (Annonaceae) jnp 54, 466 '91

I and aromatization

of the c-ring:

I

HO

Dehydrodiscretine Pseudojatrorrhizine

Fibraurea chloroleuca (Menispermaceae) pw 113, 1153'78 He ptacyclum zen keri (Menispermaceae) phy 22, 321 '83 Penianthus zenkeri (Menispermaceae) phy 22, 321 '83 Sinomenium acutum (Menispermaceae) nm 48, 287 '94 Thalictrum [auriei (Ranunculaceae) jps 69, 1061 '80 Xy lopia vieillardii (Annonaceae) jnp 54, 466 '91

77


I with a

(6,3) attack:

I

Isonorargemonine

Argemone gracilenta (Papaveraceae) jnp 46, 293 '83 Argemone munita (Papaveraceae) jnp 46, 293 '83 Eschscholzia californica (Papaveraceae) ecce 51, 1743 '86 Eschscholzia douglasii (Papaveraceae) ecce 51,1743 '86 Eschscholzia glauca (Papaveraceae) ecce 51, 1743 '86 Thalictrum minus (Ranunculaceae) pm 63, 533 '97 Thalictrum revolutum (Ranunculaceae) jnp 46, 293 '83

alsounder: 6,7 MeO MeO R Me THIQ (6,3) attack R = 3,4-HO,MeO-benzyl HO

I witha (6,8) attack: I (+)- Predicentrine

Anno na purpurea (Annonaceae)

jnp 61,1457 '98 Aromadendron

elegans (Magnoliaceae)

phy 31, 2495 '92

CH30

OCH

Beilschmiedia poda grica (Lauraceae) het 9,903 '78 Cassytha [iliformis (Lauraceae) prs 12, 39 '98 Corydalis cava (Papaveraceae) zpn 69, 99 '85 Corydalis spp. (Papaveraceae) pm 50,136 '84 Dicentra peregrina (Papaveraceae) cnc 20, 74 '84 Glaucium leiocarpum (Papaveraceae) pm 65, 492 '99 Glaucium spp. (Papaveraceae) cnc 19, 714 '83 Liriodendron tulipifera (Magnoliaceae) cnc 13, 602 '77 Litse a trif/ ora (Lauraceae) aqsc 76, 171 '80 Dc otea spp. (Lauraceae) fes 32, 767 '77 Platycapnos spicata (Papaveraceae) phy 32, 1055 '93 PolyaIthia caulif/ora var. beccarii (Annonaceae) jnp 47, 504 '84 Strychnopsis thouarsii (Menispermaceae) pm 58, 540 '92

3

78


land an a,1-ene:

I Dehydropredicentrine

Polyalthia cauliflora (Annonaceae) jnp 51, 389 '88

OH

I with

a 4-hydroxy group:

I Srilankine

Al seod ap hn e semi ca rp ifo lia (Lauraceae) jnp 42, 325 '79

HO

6-HO 7-MeO 3,4-MeO,MeO-benzyl Me,Me+ THIQ Pseudorine N-Methylpseudolaudanine

CH30 OCH3 Fagara mayu (Rutaceae) pm 48, 77 '83 Papaver pseudo-orientale (Papaveraceae) ecce 51, 1752 '86 Popowia pisocarpa (Annonaceae) jnp 49,1028 '86

the seco-compound was also isolated from this plant, the substitution positions were not determined: Pseudoronine Papaver pseudo-orientale (Papaveraceae)

ecce 51, 1752 '86


HO


N-Methylcorypalmine n-Hainanine Berberis ilien sis (Berberidaceae) cnc 29,69 '93 Cyclea hainanensis (Menispermaceae) cwhp 23, 216 '81

6-HO 7-MeO 3,4-MeO,MeO-a-Me-benzyl Me THIQ

I witha

(2,N-Me) attack:

Compound unknown

HO

I

Corybulbine GJrydalis ambigua (Papaveraceae)

42,214 '88 Corydalis cava (Papaveraceae) sz 40, 61 '86 (Papaveraceae) yz 94, 844 '74 Corydalis koidzumiana GJrydalis platycarpa (Papaveraceae) jnp 51, 262 '88 GJrydalis nobilis (Papaveraceae) ecce 54, 2009 '89 GJrydalis nokoensis (Papaveraceae) yz 96, 527 '76 GJrydalis remota (Papaveraceae) jnp 51, 262 '88 GJrydalis tuberosa (Papaveraceae) book 2 (Papaveraceae) yx 21, 447 '86 GJrydalis turtschaninovii 5Z

landaromatization of the c-ring:

I

HO,

Dehydrocorybulbine

CH30 Berberis baluchistanica (Berberidaceae)

daib 38, 686 '77 GJrydalis ambigua (Papaveraceae) daib 45, 2160 '85 GJrydalis nokoensis (Papaveraceae)

H 3C

yz 96, 527 '76

79


80

I and a carbonyl on the original N-Me group: I HO

Oxydehydrocorybulbine

Corydalis ambigua (Papaveraceae) daib 45, 2160 '85

6-HO 7-MeO 3,4-MOO-benzyl H THIQ

Not a natural product. cpb 16, 953 '68

I with a (2,8) attack: I Laetine He rnandia peltata (Hernandiaceae) cjc 64, 123 '86 Litsea laeta (Lauraceae) phy 19, 998 '80 Ocotea teleiandra (Lauraceae) rlq 23, 18 '92


HO

N orisodomesticine Glossoealyx brevipes (Monimiaceae) jnp 48, 833 '85 Guatteria goudotiana (Annonaceae) phy 30, 2781 '91 Lauru s nob ilis (Lauraceae) jnp 45, 560 '82 Xy lopia dan guy ella (Annonaceae) jnp 44, 551 '81

6-HO 7-MeO 3A-MOO-benzyl Me THIQ

Not a natural product. het 1, 223 '73



81

HO

Cheilanthifoline (5)(-)-isomer: Argem one gra ndi flora (Papaveraceae) phy 11, 461 '72 Argem one me xic ana (Papaveraceae) ecce 40, 1576 '75 Argem one och roleuc a (Papaveraceae) ecce 38, 2307 '73 Corydalis koidzumiana (Papaveraceae) yz 94, 844 '74 Corydalis spp. (Papaveraceae) phy 13,2620 '74 Fumaria bella (Papaveraceae) jnp 49,178 '86 Fumaria capreolata (Papaveraceae) jnp 49, 178 '86 Fumaria parviflora (Papaveraceae) jnp 44, 475 '81 Fumaria uaillantii (Papaveraceae) phy 22, 2073 '83 Papaver commutatum (Papaveraceae) pm 62, 483 '96

o

)

o

(d1):

D act ylicap nos torulo sa (Papaveraceae) phy 36,519 '94 Eschscholzia californica (Papaveraceae) pm 62, 188 '96

isomernot specified: Argemone hybrida (Papaveraceae) cnc 22, 189 '86 Corydalis ochotensis (Papaveraceae) jccs 34, 157 '87 D ice ntra epeciabilis (Papaveraceae) cnc 20,74 '84 Fumaria densiflora (Papaveraceae) jnp 49, 370 '86 M eni spe rm um dau ric um (Menispermaceae) yz 91, 684 '71 Papaver arenarium (Papaveraceae) cnc 20,71 '84 Papaver cylindricum (Papaveraceae) pm 46, 175 '82 Papaverfugax (Papaveraceae) cnc 24, 475 '89 Papaver triniaefolium (Papaveraceae) pm 49, 43 '83

land aromatization of the c-ring:

I

Dehydrocheilanthifoline* Groenlandicine Tetradehydrocheilanthifoline

HO

CH30

Coptischinensis (Ranunculaceae) sz 37, 195 '83 Coptisdeltoides (Ranunculaceae) sz 37, 195 '83 Coptisgroenlandica (Ranunculaceae) pm 21, 313 '72

o

)

o


82

Copt is japonica (Ranunculaceae) jnp 47, 189 '84 Coptis quinquefolia (Ranunculaceae) sz 46, 42 '92 Coptis trifolia (Ranunculaceae) phy 31,717 '92 Corydalis humosa (Papaveraceae) jcpu 20, 261 '89 Corydalis ochotensis (Papaveraceae) jcspt I, 63 '76 Corydalis ophiocarpa (Papaveraceae) yz 98, 1658 '78 Fumaria capreolata (Papaveraceae) per 4, 96 '85 Fumaria indica (Papaveraceae) phy 15, 545 '76 M en isp er mu m ca na de ns e (Menispermaceae) llyd 34, 292 '71 N an di na do me stica (Berberidaceae) phy 27, 2143 '88 (Ranunculaceae) pm 53, 498 '87 Thalictrum glandulosissimum

"This name has also been given to the 6-MeO 7-HO isomer. HO

with a (6,N-Me) attack, and aromatization of the c-ring: Thalifaurine

Copt is quinquefolia (Ranunculaceae) sz 43, 81 '89 Thalictrum fauriei (Ranunculaceae) jps 69, 1061 '80 HO

I with a (6,N) attack: I Cryptowolidine

CH30

Cryptocarya phyllostemon (Lauraceae) cjc 67, 947 '89 OH

I with a (6,3) attack: I (-)-Caryachine Cryptocarya Eschscholzia Eschscholzia Eschscholzia

CH30

chinensis (Lauraceae) jnp 53, 1267 '90 californica (Papaveraceae) ecce 51, 1743 '86 douglasii (Papaveraceae) ecce 51, 1743 '86 glauca (Papaveraceae) ecce 51, 1743 '86

also under: 6,7 MDO R Me THIQ R= 3,4-HO,MeO-benzyl (6,3) attack

o o>


83

I with a (6,4) attack: I Reframoline

zh 27, 459 '96 Mecon opsis speciosa (Papaveraceae) jnp 46, 293 '83 Roemeria refracta (Papaveraceae)

I with a (6,8) attack:

HO

I

CH30

Isodomesticine

phy 30, 2781 '91 Guatteria goudotiana (Annonaceae) La urus nobilis (Laraceae) jnp 45, 560 '82 Litsea spp. (Laraceae) jccs 39, 453 '92 jnp 38, 275 '75 Na ndina domestica (Berberidaceae) Neolitse a villo sa (Laraceae) cpj 47, 69 '95 phy 32, 1055 '93 Platycapnos spicata (Papaveraceae)

6-HO 7-MeO

Compound

unknown

3,4-MDQ-benzyl

Me,Me+ THIQ

HO

I with a (2,N-Me)

attack:

I CH30

N-Methylcheilanthifoline

D icentra spectabilis

(Papaveraceae)

I with a (6,3) attack: I Caryachine methiodide N-Methylcaryachinium quat

quat

o

sz 46, 109 '92

OH

CH30

jnp 42, 163 '79 Cryptocarya chinensis (Lauraceae) ecce 51, 1743 '86 Eschscholzia californica (Papaveraceae)

o> o

) o

84


Eschscholzia douglasii (Papaveraceae) ecce 51, 1743 '86 Eschscholzia glauca (Papaveraceae) ecce 51, 1743 '86

also under: 6,7 MOO R Me,Me+ THIQ R= 3,4-HO,MeO-benzyl (6,3) attack HO

with a (6,8) attack and a 1,2 seco:

CH30

3-0-Demethylthalicthuberine Ocotea insularis (Lauraceae) jnp 57, 1033 '94

6-HO 7-MeO 3,4-MOO-a-Me-benzyl Me THIQ

Compound unknown

I with a (2,N-Me) attack: I Isoapocavidine

o

D ac tylic ap no s to ru lo sa (Papaveraceae) phy 36,519 '94

6-HO 7-MeO 2,3,4-MDO,MeO-benzyl Me THIQ

o>

Compound unknown

HO I with a (6,3) attack: I

(-)-9-Demethylthalimonine Thalictrum simplex (Ranunculaceae)

pm 59, 262 '93

also under: 5,6,7 MOO MeO R Me THIQ R= 3,4-HO,MeQ-benzyl (6,3) attack

OC H 3


6-HO 7-MeO 3,4,5-MeO,MeO,MeO-benzyl Me THIQ

85

Compound unknown

HO

I witha (2,8)attack: I

Acutifolidine CH30

CH30 Thalicrum acutifolium (Ranunculaceae)

jn p 57,1033'94

CH 0 3

OCH3

HO

6-HO 7-MeO ~-(4-Ho-phenyl)ethyl Me THIQ

CH30

(S)-Colchiethanamine

Colchicum szavitsii

(Liliaceae) jnp 53,634 '90

OH HO

6-HO 7-MeO 1 3 - ( 4-MeO-phenyl)ethyl Me THIQ

CH30 (S)-Colchiethine

Colchicum szavitsii (Liliaceae) jnp 53,634 '90 OCH3

86


HO

6-HO 7-MeO ~-(3,4,5-HO ,MeO,MeO-phenyl)ethyl Me THIQ

CH30

(-)-Isoautumnaline

Colchicum ritchii (Liliaceae) jnp 50,684 '87

OH OCH3

HO

6-HO 7-MeO 6',7'-MDG-isobenzofuranone,3'-yl Me THIQ

CH30

Corle dine 6-0-Demethy ladlumine Corydalis ledebouriana (Papaveraceae) jnp 45, 105 '82 Fumaria parviflora (Papaveraceae) ojc 14, 217 '98 Fumaria oaillaniii (Papaveraceae) tet 39, 577 '83 HO

Corlumidine

CH30 (+)-isomer: Corydalis decumbens (Papaveraceae) jcps 4, 57 '95 Corydalis linarioides (Papaveraceae) yhhp 16, 798 '81 Corydalis scouleri (Papaveraceae) jnp 45, 105 '82 Fumaria parviflora (Papaveraceae) ojc 14,217 '98

6-HO 7-MeO 3,4-MDO-a-(=CHz )-benzyl, Me THIQ

Compound unknown Me


[witha (2,I-Me) attack:

HO

I

(+)-Ochotensine Corydalis Corydalis Corydalis Corydalis

6-HO

87

CH30

ochotensis (Papaveraceae) jccs 34, 157 '87 solida (Papaveraceae) cjc 56, 383 '78 stewartii (Papaveraceae) jnp 51, 1136 '88 thyrsiflora (Papaveraceae) yx 26, 303 '91

Compound unknown

7-MeO

3,4-MDO-benzyl, HO Me,Me+ THIQ HO

I with a (2,N-Me) attack: I Izmirine

CH30

o Fumaria parviflora

(Papaveraceae)

jnp 46,934 '83

o>

88


6,7-MeO,HO-ISOQUINOLINES

6-MeO

7-HO

Norcorypalline

CH 30m

H

H

~

THIQ

Ziz ip hu s ru go sa (Rhamnaeeae)

6-MeO

7-HO

I

NH

HO

phy 27, 1915 '88

Corypalline

CH 30~

H

Me

H O ~ N C H 3

THIQ

Ber be ris nu mm ul ar ia (Berberidaeeae) cne 33, 70 '97 Ber be ris tu reom an ni ea (Berberidaeeae) cne 29, 63 '93 Ber be ris va ld iv ia na (Berberidaeeae) fit 64, 378 '93 Corydalis ophioearpa (Papaveraceae) yz 98, 1658 '78 Corydalis speeiosa (Papaveraeeae) yz 95, 838 '75 Corydalis strieta (Papaveraeeae) kps 19,461 '83 D or yp ho ra sa ssaf ra s (Monimiaeeae) llyd 37,493 '74 Isl ay a mi no r (Cactaeeae) je 189, 79 '80 M en ispe rm um da ur ieum (Menispermaeeae) tcyyk 5,30 '93 Papaver braeteatum (Papaveraeeae) phy 22, 247 '83 Stephania eepharantha (Menispermaeeae) nm 52, 541 '98 Thalietrum dasyearpum (Ranunculaeeae) joe 34, 1062 '69 Thalietrum rugosum (Ranunculaeeae) jnp 43,143 '80 Thalietrum uehiyamai (Ranunculaeeae) kjp 13, 132 '82 X ylop ia vi eilla rd ii (Annonaeeae) jnp 54, 466 '91

6-MeO

7-HO

Dehydrocorypalline

H

Me

(+J-Pycnarrhine

DHIQ

Ar ea ng elisia flav a (Menispermaeeae) Corydalis ophioearpa (Papaveraeeae)

CH 30ro

HO

jnp 45, 582 '82 yz 98, 1658 '78

~

I

+ ~ N C H3

89

Structural Index - 6,7-MeO,HO-Substituted

Corydalis stricta (Papaveraceae) kps 4, 490 '83 Pycnarrhena longifolia (Menispermaceae) phy 20, 323 '81

6-MeO 7-HO H

Me,Me+ THIQ 2-Methylcorypallinium N-Methylcorypalline Corydalis stricta

6-MeO

(Papaveraceae)

kps 4, 490 '83

Corgoine

7-HO

C H 3 0 m

H

I

4-HO-benzyl THIQ

HO

N

~

Ceratocapnos sp. (Papaveraceae) kps 7, 211 '70 Corydalis sp. (Papaveraceae) kps 6, 638 '70

6-MeO 7-HO H 4-MeQ-benzyl THIQ

OH

C H 3 0 m

I HO

~

N

Sendaverine Corydalis gortschakovii (Papaveraceae) kps 6, 438 '70 (Papaveraceae) phy 36, 241 '94 Ceratocapnos heterocarpa Cory dalis im patiens (Papaveraceae) patent 3 Corydalis tashiroi (Papaveraceae) pm 41, 403 '81

I the N-oxide: I Sendaverine Corydalis gortschakovii

N-oxide

(Papaveraceae)

kps 6, 834 '77

O C H 3

90


6-MeO

CH 30m

7-HO

H

3,4-HO,MeO-benzyl

THIQ

HO

I

N

~

Capnosine Ceratocapnos heterocarpa (Papaveraceae) phy 36, 241 '94 Corydalis sp. (Papaveraceae) phy 36, 241 '94

6-MeO Me

7-HO

H

THIQ

HO

OCH3

C H 3 0 :c y

Isosalsoline

I

HO

NH

~

CH3

Ha mma da articulata (Chenopodiaceae) apf 48,219 '90 Pachycereus pecten-aboriginum (Cactaceae) aps 15, 127 '78

6-MeO Me H

C H 3 0 :c Q " " ::::::

7-HO IQ

HO::::::"'"

7-0-Desmethylisosalsolidine He rna ndia nym phaeif olia (Hernandiaceae)

6-MeO Me Me

7-HO

~

phy 42,1479 '96

0Y(J

3

CH

HO~NCH,

THIQ

CH3

phy 12, 3008 '73

(S)(-)-isomer: Arthro cnemu m glau cum(C henop odia ceae) isomer not specified: Haloxylon articulatum (Chenopodiaceae)

N

C H3

I-Methylcorypalline N-Methylisosalsoline

(R)(+)-isomer: Corydalis ambigua (Papaveraceae)

I

phy 31,1023 '92

book 6


Lophocereine Lophocerine

7-HO

6-MeO i-Bu Me

THIQ

iopnocereus schottii (Cactaceae) phy 8,1481 '69 (Cactaceae) book 6 Pachycereus marginatus

H

Not a natural product. joc 41,443 '76

7-HO

6-MeO be nz yl

THIQ

IWitha (2,8) attack:

CH30

I Caaverine

HO Isolona pilosa (Annonaceae) pm 50, 23 '84 Liriodendron tulipifera (Magnoliaceae) cnc 23, 521 '88 Liriodendron sp. (Magnoliaceae) jnp 38, 275 '75 (Annonaceae) jnp 51, 973 '88 Neostenanthera gabo nensis Ocoteaglaziovii (Lauraceae) fes 30, 479 '75 Ocotea sp. (Lauraceae) jnp 38, 275 '75 (Papaveraceae) paz 13, 50 '77 Papaver pseudo-orientale Polyalthia acuminata (Annonaceae) jnp 45, 471 '82 Symplocos celastrinea (Symplocaceae) llyd 33s, 1 '70 Symplocos sp. (Symplocaceae) jnp 38, 275 '75 Ziz iphus jujuba (Rhamnaceae) apr 12, 263 '89 Ziz iphus spinosus (Rhamnaceae) sh 16, 233 '86

6-MeO be nz yl Me

7-HO

Not a natural product. jhc 4, 417 '67

THIQ

lwitha (2,N-Me) attack: I Bharatamine

Alangium lamarckii

(Alangiaceae) tl24, 291 '83

HO

91

92



CH30 Lirinidine Nomuciferine I

HO

Lirinidine: An no na pu rp ur ea (Annonaceae) phy 49, 2015 '98 Ar ta bo try s ve nu stus (Annonaceae) jnp 49,602 '86 Guatteria sagotiana (Annonaceae) jnp 49,1078 '86 Isolona zenkeri (Annonaceae) pm 50, 23 '84 Liri od en dr on tu lip ifer a (Magnoliaceae) cnc 23, 521 '88 N elum bo nu cife ra (Nymphaeaceae) jnp 50, 773 '87 N eo sten an ther a ga bo ne ns is (Annonaceae) jnp 51,973 '88 Ocotea macrophylla (Lauraceae) pptp 27, 65 '93 Papaver spp. (Papaveraceae) pm 41,105 '81 Nornuciferine I: Croton bonplandianus (Euphorbiaceae) abs 10 Croton sparsiflorus (Euphorbiaceae) tet 35, 2323 '79

I and an a.,1-ene: I Dehydrolirinidine An no na pu rp ur ea (Annonaceae)

6-MeO 7-HO a.-NH2-benzyl H IQ

jnp 61,1457 '98

Compound unknown

with a (2,8)attack aromatization and oxidation: Telazoline Telitoxicum peruvianum (Menispermaceae) jnp 44, 320 '81

HO

93


Compound unknown

6-MeO 7-HO a-keto-benzyl Me+

IQ

I with a (2,8) attack: I O,N-Dimethylliriodendronine

HO

Guatteria chrysopetala (Annonaceae) pmp 18, 165 '84 Stephania dinklagei (Menispermaceae) pm 66,478 '00

6-MeO 7-HO 3-HO-benzyl H THIQ

(-)-N orcanelilline Aniba cane lilla (Lauraceae)

cjc 71, 1128'93 OH

6-MeO 7-HO 3-HO-benzyl Me THIQ

Canelilline

Anib a canelilla (Lauraceae)

cjc 71, 1128 '93

OH

I with a (2,N-Me)

attack:

I Anibacanine

Aniba canelilla (Lauraceae)

cjc 71,1128'93

OH

94


land a methyl group on the original N-Me group:

I

(-)-a-8-Methylanibacanine An ib a ca ne lil la (Lauraceae) cjc 71, 1128 '93

I with a (2,8) attack: I Isothebaidine Papaver orientale (Papaveraceae) cnc 14, 402 '78

HO HO

I with a (6,N-Me) attack: I (-)-Pseudoanibacanine An ib a ca ne lil la (Lauraceae) cjc 71, 1128 '93

land a methyl group on the original N-Me group:

I

OH

the cis isomer: (-)-8a-Methylpseudoanibacanine An ib a ca ne lil la (Lauraceae) cjc 71,1128 '93

the trans isomer: (-)-8~-Methylpseudoanibacanine An ib a ca ne lil la (Lauraceae) cjc 71, 1128 '93

OH

95


Compound unknown

6-MeO 7-HO 3-MeO-benzyl THIQ H

CH30

I with a (6,8) attack: I Nororientinine HO Ocotea caesia (Lauraceae) jnp 57, 1033 '94

OCH3

6-MeO 7-HO 3-MeO-benzyl Me THIQ

Not a natural product. cpb 29, 1083 '81

I witha (2,8)attack: I

Isothebaine

Discaria serratifolia (Rhamnaceae)

CH30 HO

CH30 jnp 47, 1040 '84 Papaver atlanticum (Papaveraceae) ecce 51,2232 '86 Papaver bracteatum (Papaveraceae) pm 32, 60 '77 Papaver nudicaule (Papaveraceae) zpf 114, 361'84 Papaver orientale (Papaveraceae) jps 66, 1050 '77 (Papaveraceae) paz 13, 50 '77 Papaver pseudo-orientale Papaver setigerum (Papaveraceae) zpf 114,361 '84 Papaver somniferum (Papaveraceae) zpf 114, 361 '84

I andan CJ.,1-ene:I Dehydroisothebaine Papaver orientale (Papaveraceae)

jnp51, 389 '88

HO CH30

96


I with a (6,8) attack: I Orientinine

Papaver orientale (Papaveraceae)

jnp 51, 389 '88 OCH3

6-MeO 7-HO 3-MeO-benzyl Me,Me+ THIQ

Compound unknown


CH30

N-Methylisothebainium cation N-Methylisothebaine

HO CH30

Papaver bracteatum (Papaveraceae) jnp 51, 389 '88 Papaver pseudo-orientale (Papaveraceae) ecce 51, 1752 '86

6-MeO 7-HO 3-MeO-a-keto-benzyl Me IQ

Compound unknown

I with a (2,8) attack: I Alkaloid PO-3

HO

CH30 Papaver orientale (Papaveraceae) jnp 38, 275 '75


6-MeO 7-HO 4-HQ-benzyl THIQ H

Coclaurine Machiline Sanjoinine K

CH30 HO

(S)(-)-isomerof Coclaurine HO Machiline: Alseodaph ne archbo ldiana (Lauraceae) het 9,903 '78 Aniba canelilla (Lauraceae) cjc 71,1128 '93 Ann ona mon tana (Annonaceae) pmp 16, 169 '82 Ann ona retic ulata (Annonaceae) jcspt I, 1515, '79 Cocculus hirsutus (Menispermaceae) npl 2, 105 '93 Cocculus pendulus (Menispermaceae) jpic 32, 250 '60 Corydalis gortschakovii (Papaveraceae) kps 6, 638 '70 Corydalis paniculigera (Papaveraceae) cnc 18, 689 '82 (Papaveraceae) cnc 21, 807 '86 Corydalis pseudoadunca Cryptocarya longifolia (Lauraceae) ajc 34, 195 '81 Fumaria parviflora (Papaveraceae) cnc 18, 608 '82 Fumaria vaillantii (Papaveraceae) cnc 17, 437 '81 Litseaglutinosa (Lauraceae) abs 10 Litsea leca rdii (Lauraceae) pm 52, 74 '86 (Lauraceae) het 9,903 '78 Mach ilus acuminatissima M achilus ku sanoi (Lauraceae) het 9,903 '78 M agn olia salic ifolia (Magnoliaceae) pm 48, 43 '83 M ezilaurus synand ra (Lauraceae) phy 22, 772 '83 Ny mphaea stellata (Nymphaeaceae) jics 63, 530 '86 Pachygone ovata (Menispermaceae) daib 45, 567 '84 Peumus boldus (Monimiaceae) fit 64, 455 '93 Phoebe minutiflora (Lauraceae) cpj 49,217 '97 Polyalthia macropoda (Annonaceae) phy 29, 3845 '90 Retanilla ephedra (Rhamnaceae) rlq 5, 158 '74 Stephania pierrei (Menispermaceae) jnp 52,846 '89 Xylop ia pap uan a (Annonaceae) npl6, 57 '95 Ziz iphu s jujuba (Rhamnaceae) apr 12, 263 '89 Ziz iphu s spin osu s (Rhamnaceae) kjp 16, 44 '85 Ziziphus vulgaris (Rhamnaceae) apr 10, 203 '87 (R)(+}-isomer of Coclaurine SanjoinineK: Abu ta pah ni (Menispermaceae)

phy 26, 2136 '87

97

98


Al se od ap hn e ar ch bo ld ia na (Lauraceae) het 9, 903 '78 An no na mu ric at a (Annonaceae) pm 42, 37 '81 Bon ga rd ia ch ry so go nu m (Berberidaceae) jnp 52,818 '89 Caryomene olivascens (Menispermaceae) afb 6, 163 '87 Cassytha racemosa (Lauraceae) het 9, 903 '78 Cocculus laurifolius (Menispermaceae) tet 36, 3107 '80 Colubrina faralaotra ssp. sinuata (Rhamnaceael pm 30, 201 '76 Corydalis severtzovii (Papaveraceae) cnc 11, 826 '75 Cyclea barbata (Menispermaceae) jnp 56, 1989 '93 Cyclea peltata (Menispermaceae) jnp 56,1989 '93 D isc ar ia pu be scen s (Rhamnaceae) pm 50, 454 '84 L its ea triflo ra (Lauraceae) aqsc 76,171 '80 M ag no lia fa rg es ii (Magnoliaceae) pm 48, 43 '83 M ag no lia lil iflo ra (Magnoliaceae) yhtp 20, 522 '85 M ag no lia sa lic ifol ia (Magnoliaceae) pm 48, 43 '83 N ec ta nd ra sa lic ifol ia (Lauraceae) jnp 59, 576 '96 N eo lit se a vi llo sa (Lauraceae) cpj 47, 69 '95 Peumus boldus (Monimiaceae) fit 64, 455 '93 Polyalthia acuminata (Annonaceae) jnp 45,471 '82 Popowia pisocarpa (Annonaceae) jnp 49, 1028 '86 Ro em er ia re frac ta (Papaveraceae) hca 75, 260'92 Sciadotenia eichleriana (Menispermaceae) jnp 48, 69 '85 Sparattanthelium uncigerum (Hernandiaceae) jnp 48,333 '85 Stephania cepharantha (Menispermaceae) cpb 45, 470 '97 Stephania excentrica (Menispermaceae) jnp 60, 294 '97 Ziz ip hu s ju ju ba (Rhamnaceae) apr 12, 263 '89 Ziz ip hu s vu lgar is (Rhamnaceae) apr 12, 263 '89

(d1)-Codaurine: Cocculus hirsutus (Menispermaceae) ijc 14b, 62 '76 Cryptocarya konishii (Lauraceae) het 9, 903 '78 M ac hi lu s ac um in at iss im a (Lauraceae) het 9, 903 '78 M ac hi lu s ma cran th a (Lauraceae) het 9,903 '78 Peumus boldus (Monimiaceae) fit 64, 455 '93 Polyalthia acuminata (Annonaceae) jnp 45,471 '82 Re ta ni lla ep he dr a (Rhamnaceae) rlq 5, 158 '74 Talguenea quinquenervis (Rhamnaceae) aaqa 62, 361 '74 X ylop ia pa pu an a (Annonaceae) llyd 33s, 1 '70 Ziz ip hu s ju ju ba (Rhamnaceae) kps 13,239 '77


I with a (l,8) attack: I

CHsO Crotsparine Crotoflorine

HO

Alphons ea scle roca rpa (Annonaceae) jnp 50, 518 '87 (Euphorbiaceae) jcspt 1659 '75 Croton bonplandianus Croton flavens (Euphorbiaceae) llyd 32, 1 '69 Croton ruizianus (Euphorbiaceae) bse 24, 463 '96 Croton sparsiilorus (Euphorbiaceae) llyd 32, 1'69 M onod ora brevipes (Annonaceae) phy 28,2489 '89 Ocotea glaziovii (Lauraceae) het 9, 903 '78

CHsO

with reduction of the benzyl 2,3 double-bond:

HO (lS-cis) (+)-Crotsparinine Croton bonplandianus

(Euphorbiaceae)

jcspt 1659 '75

(lR-trans) (-)-Jacularine Croton discolor (Euphorbiaceae) rlq I, 140 '70 Croton echinocarpus (Euphorbiaceae) llyd 32, 1'69 Croton linearis (Euphorbiaceae) llyd 32, 1 '69 Croton plumieri (Euphorbiaceae) rlq I, 140 '70 Croton ruizianus (Euphorbiaceae) bse 24, 463 '96 Croton sparsiflorus (Euphorbiaceae) exp 25, 354 '69

R,S is Crotsparinine R,R is Jacularine

withreduction of both double bonds andof the carbonyl group in the benzyl ring:

Oridine Oreoline (-)-isomer:

CHsO HO

Papaver lisae (Papaveraceae) cnc 14, 228 '78 Papaveroreophilum (Papaveraceae) frm 29, 23 '80

HO

99


100

I with

a (2,8) attack:

I

Sparsiflorine Apocrotsparine

(-I-Isomer: M on od or a te nu ifol ia (Annonaceae)

pm 50, 455 '84

isomer not specified: Al ph on se a scle ro ca rp a (Annonaceae) jnp 50,518 '87 Croton bonplandianus (Euphorbiaceae) jcspt 1,1659 '75 Croton flavens (Euphorbiaceae) llyd 32, 1 '69 Thalicirum foliolosum (Ranunculaceae) jnp 45,252 '82

6-MeO 7-HO 4-HO-benzyl H IQ

Juzirine Yuzirine

HO

Ziz ip hu s ju ju ba (Rhamnaceae) iant 4,48 '87 M ag no lia fa rg es ii (Magnoliaceae) pm 48, 43 '83 M ag no lia sa lic ifol ia (Magnoliaceae) ws 14, 101'81

6-MeO 7-HO 4-HO-a-keto-benzyl H DHIQ

HO

Longifolonine

Cryptocarya velutinosa (Lauraceae) ajc 34, 195 '81

6-MeO 7-HO 4-HO-benzyl Me THIQ

N-Methylcoclaurine

HO

(S)(+)-isomer: HO An ib a ca ne lil la (Lauraceae) cjc 71, 1128 '93 D es mo s tie ba gh ie ns is (Annonaceae) jnp 45,617 '82 Stephania cepharantha (Menispermaceae) cpb 45, 470 '97


Stephania p ierrei (Menisperrnaceae) jnp 52, 846 '89 (Ranunculaceae) llyd 40, 593 '77 T h a l ic t ru m r e v o lu t u m

(R)(-)-isomer: A nib a burc hellii (Lauraceae) bse 8, 51 '80 (Lauraceae) bse 8, 51 '80 A nib a cylindri fl ora A n ib a si m ula ns (Lauraceae) bse 8, 51 '80 B erb eri s ly ciu m (Berberidaceae) daib 44, 1458 '83 (Papaveraceae) jnp 53, 1006 '90 Ceratocapnos palaestinus Cryptocarya longifolia (Lauraceae) ajc 34,195 '81 Cyclea peltata (Menispermaceae) jnp 56, 1989 '93 D isc ari a se rr ati fo li a var. discolor (Rhamnaceae) jnp 42, 430 '79 D isc ari a to um ato u (Rhamnaceae) jnp 45,777 '82 (Papaveraceae) cnc 16, 177 '80 G laucium fim brilligerum G laucium leiocarpum (Papaveraceae) pm 65, 492 '99 Cuaiteria sagotiana (Annonaceae) jnp 49, 1078 '86 L it se a tr iflo ra (Lauraceae) aqsc 76,171 '80 M ag noli a fa rg esi i (Magnoliaceae) pm 48, 43 '83 M ag noli a sa licif olia (Magnoliaceae) pm 48, 43 '83 Thalictrum dioicum (Ranunculaceae) llyd 41, 169 '78 X ylo p ia pancheri (Annonaceae) pm 30, 48 '76 X ylo pia vie illa rd ii (Annonaceae) jnp 54, 466 '91 Z iz ip hus m uc ro nata (Rhamnaceae) phy 13, 2328 '74 (dl):

B erb eri s a ctinaca nth a (Berberidaceae) daib 45,2160 '85 B erb eri s b oli via na (Berberidaceae) jnp 52, 81 '89 (Berberidaceae) jnp 52, 818 '89 B onga rd ia ch ry so gon um Polyalthia acum inata (Annonaceae) jnp 45, 471 '82 R oem eria re fr a ct a (Papaveraceae) hca 75, 260 '92 Tiliacora racem osa (Menispermaceae) cc 226 '78

isomer not specified: A nib a m uc a (Lauraceae) rbq 13, 19 '96 A nno na sq uam osa (Annonaceae) cpj 46, 439 '94 (Annonaceae) fit 65, 92 '94 A rt abotr ys od ora tiss im us B erb eri s ilie nsi s (Berberidaceae) cnc 29, 69 '93 B erb eri s nu m m ula ri a (Berberidaceae) cnc 29, 335 '93 B erb eri s vald iv ia na (Berberidaceae) fit 64, 378 '93 Co cculus laurifolius (Menispermaceae) ijc 26b, 24 '87 Corydalis gortschakovii (Papaveraceae) cnc 20, 245 '84 D isc ari a crenata (Rhamnaceae) phy 12, 954 '73

101


102

Fumaria capreolata (Papaveraceae) per 4, 96 '85 Glaucium oxylobum (Papaveraceae) cnc 20, 244 '84 Gyrocarpus american us (Hernandiaceae) jnp 49,101 '86 Lits ea ac um in at a (Lauraceae) cpj 46, 299 '94 N ec ta nd ra sa lic ifol ia (Lauraceae) jnp 59, 576 '96 Re ta ni lla ep he dr a (Rhamnaceae) rlq 5, 158 '74 Stephania excentrica (Menispermaceae) zh 27, 586 '96 Thalictrum longistylum (Ranunculaceae) jnp 62, 1410 '99

!xyloside at the 7-HO position:

I Latericine

Papaver californicum (Papaveraceae)

svs 55, 23 '93

CH30

I with a (1,8) attack: I N-Methylcrotsparine Glaziovine Suavedol (R)(+)-isomer: N-Methylcrotsparine Glaziovine: An no na ch er im ol ia (Annonaceae)

HO

0 pmp 23,159 '89

(5)(-)-isomer: N-Methylcrotsparine Glaziovine Suavedol: An ib a ca ne lil la (Lauraceae) cjc 71, 1128 '93 An no na pu rp ur ea (Annonaceae) jnp 61, 1457 '98 Ar isto loch ia ch ile ns is (Aristolochiaceae) fit 61, 190 '90 B erbe ris lycium (Berberidaceae) daib 44, 1458 '83 Corydalis claviculata (Papaveraceae) jnp 53, 1280 '90 Croton bonplandianus (Euphorbiaceae) tet 37,3175 '81 D esmos tie ba gh ie ns is (Annonaceae) jnp 45, 617 '82 Guatteria sagotiana (Annonaceae) jnp 49, 1078 '86 Iso lo na ze nk er i (Annonaceae) pm 50, 23 '84 Liri od en dr on tu lip ifera (Magnoliaceae) cnc 11, 829 '75 Lits ea cu be ba (Lauraceae) jca 667, 322 '94


Litsea laur ifolia (Lauraceae) pmp 13, 262 '79 M eeanop sis cam bric a (Papaveraceae) jpps 27, 84p '75 Neeta ndra mem branac ea (Lauraceae) pptp 27, 65 '93 Ne etan dra salicifo lia (Lauraceae) jnp 59, 576 '96 Ne oste nan ther a gab one nsis (Annonaceae) jnp 51, 973 '88 Ocotea brachybotra (Lauraceae) pptp 27, 65 '93 D eote a glaziovii (Lauraceae) het 9,903 '78 D eote a variabilis (Lauraceae) pptp 27, 65 '93 Paehygone ovata (Menispermaceae) jnp 42, 399 '79 Papaver caucasicum (Papaveraceae) phzi 23, 267 '68 Stephania eepharantha (Menispermaceae) cpb 45, 470 '97 Uvaria ehamae (Annonaceae) pmp 14, 143 '80

isomernot specified: Ne olits ea konish ii (Lauraceae) phzi 45, 442 '90

I with the reduction of a double bond: I N-Methylcrotsparinine

CH30 HO

Croton bonplandianus (Euphorbiaceae)

jcspt I, 1659 '75

I witha (2,8)attack: I Apoglaziovine N-Methylsparsiflorine N- Methylapocrotsparine

CH30 HO

(5)(+ l-isorner: HO Aniba canelilla (Lauraceae) cjc 71, 1128 '93 Berberis brandis iana (Berberidaceae) jnp 49, 538 '86 Croton bonplandianus (Euphorbiaceae) jnp 38, 275 '75 Croton sparsiflorus (Euphorbiaceae) tet 37, 3175 '81 Lir iode ndron tulip ifera (Magnoliaceae) cnc 27,516 '92 D eote a sp_(Lauraceae) jnp 38, 275 '75 (R)(-)-isomer(Apoglaziovine only): Neeta ndra mem bra nacea (Lauraceae) fit 60, 474 '89 Stephania venosa (Menispermaceae) jnp 50, 1113 '87

103


104

6-MeO 7-HO 4-HO-benzyl Me,Me+ THIQ

CH30

Magnocurarine

HO

(5)(+)-isomer: Euodia trichotoma (Rutaeeae) pm 59, 290 '93 Lin dera oldh amii (Lauraeeae) jnp 49, 726 '86 Litsea cubeba (Lauraeeae) het 9, 903 '78

HO

(R)(-)-isomer: Colletia hystix (Rhamnaeeae) aaqa 59, 343 '71 Colletia spinosissima (Rhamnaeeae) llyd 335, 1 '70 Dicentra spe ctab ilis (Papaveraeeae) sz 46, 109 '92 Le ontice leontop etalum (Berberidaeeae) jnp 49, 726 '86 Lits ea cub eba (Lauraeeae) jnp 56, 1971 '93 Ma gno lia acu minata (Magnoliaeeae) llyd 335, 1 '70 Magn olia obovata (Magnoliaeeae) pm 58, 137 '92 Ma gnolia officinalis var. biloba (Magnoliaeeae) nm 50, 413 '96 Ma gnolia rostrata (Magnoliaeeae) ety 12, 10 '81 Tiliacora racemosa (Menispermaeeae) jic 57, 773 '80 isomer not specified: Ma gno lia ang lietia (Magnoliaeeae) yhhp 23, 383 '88 Magnolia spr eng eri (Magnoliaeeae) yhhp 23, 383 '88 Magnolia sze chu anic a (Magnoliaeeae) yhhp 23, 383 '88 Magn olia wilsonii (Magnoliaeeae) yfz 2, 95 '82 Ma nglietia chingii (Magnoliaeeae) yhhp 24, 295 '89 Ma nglietia duc loux ii (Magnoliaeeae) yhhp 24, 295 '89 Ma nglietia insignis (Magnoliaeeae) yhhp 24, 295 '89 Ma nglietia sze chuan ica (Magnoliaeeae) yhhp 24, 295 '89 Mang lietia yuyuane nsis (Magnoliaceae) yhhp 24, 295 '89

6-MeO 7-HO 4-HO-a-HD-benzyl H IQ

Annocherine

Annon a cherimolia (Annonaeeae)

A

CH30 HO

phy 56,753 '01 HO


6-MeO 7-HO 4-HO-a-MeO-benzyl H IQ

Anno na cherimolia

Annocherine

B

CH30 HO

(Annonaceae)

phy 56, 753 '01 HO

6-MeO 7-HO 4-HO-a-HO-benzyl Me,Me+ THIQ (+)-la-Hydroxymagnocurarine Cryptocarya konishii (Lauraceae)

jnp 56,1971 '93

6-MeO 7-HO 4-MeO-benzyl H THIQ

I with a (2,8)attack: I

Not a natural product. Is 30, 1747 '82

Zenkerine lO-Methoxycaaverine

CH30 HO

(-)-isomer: Dc otea caesia (Lauraceae) jnp 42, 325 '79

isomernot specified: Iso/ana pi/osa (Annonaceae) era 285, 447 '77 Iso/a na zenkeri (Annonaceae) pm 50, 23 '84

6-MeO 7-HO 4-MeO-benzyl Me THIQ

N-DemethyIcoIIetine

CH30

CH30 HO

(R)-isomer: Acon itum /eucostomum (Ranunculaceae)

kps6,805'80

CH30

105


106

Disca ria ser ratifolia (Rhamnaceae) jnp 42, 430 '79 Xy lopia pan ch eri (Annonaceae) pm 30, 48 '76

CH30

I with a (2,3) attack: I 2,9-Dimethoxy-3-hydroxypavinane Argemone munita (Papaveraceae)

HO

joe 38, 3701 '73

also under: 7 MeO R Me THIQ R= 3,4-MeO,HO-benzyl (6,3) attack CH30

I with a (2,8) attack: I N-MethyIzenkerine Pulchine

HO

Ocotea caesia (Lauraceae) jnp 42, 325 '79

CH30

6-MeO 7-HO 4-MeO-benzyl Me,Me+ THIQ

Colletine HO

Colchicum luteum (Liliaceae) kpr 12, 359 '76 Colletia spinosissima (Rhamnaceae) CH30 llyd 335, 1 '70 Cymbopetalum brasiliense (Annonaceae) pm 50,517 '84 Zan thoxy lum sar asin ii (Rutaceae) pm 54, 189 '88

6-MeO 7-HO 4-MeO-a-keto-benzyl H DHIQ

VeIucryptine

CH30

HO

Cryptocarya velutinosa (Lauraceae) jnp 52, 516 '89 CH30


6-MeO 7-HO 2,3-MeO,MeO-a-keto-benzyl H IQ

Compound

unknown

CH30


Annolatine

HO

A nnona m onta na

(Annonaceae)

6-MeO 7-HO 2,3-MOO-benzyl,Me Me THIQ

phy 33, 497 '93

Compound

unknown

witha (6,1-Me) attack, theN-oxide:

HO (+)-Papracinine

Fumaria indica (Papaveraceae)

6-MeO 7-HO 2,3-MOO-a-keto-benzyl,Me Me THIQ

lwitha (6,1-Me)attack:

phy 31,2869 '92

Compound unknown

I (+)-Parfumine HO

Corydalis rutifolia (Papaveraceae) ijcdr 26, 155 '88 Corydalis solida (Papaveraceae) guefd 5, 9 '88 Fumaria densiflora (Papaveraceae) cccc 61, 1064 '96 Fumaria indica (Papaveraceae) phy 31, 2869 '92 Fumaria mural is (Papaveraceae) jpps 33, 16 '81

107


108

Fumaria officina lis (Papaveraceae) jnp 46, 433 '83 Fumaria parviflora (Papaveraceae) pm 45,120 '82 Fumaria rostellata (Papaveraceae) dban 25, 345 '72

6-MeO 7-HO 2,3-MDO-a-HO-benzyl, Me THIQ

I with a (6,I-Me) attack: I

Compound unknown Me

Fumaritine Fumarophycinol

CH30 HO

(+)-isomer:

Corydalis caucasica (Papaveraceae) ijcdr 27, 161 '89 Corydalis solida (Papaveraceae) jcsp 13, 63 '91

(-)-isomer: Corydalis rutifolia (Papaveraceae) ijcdr 26, 155 '88 Fumaria bastardii (Papaveraceae) nps 4, 257 '98 Fumaria densiflora (Papaveraceae) ecce 61, 1064 '96 Fumaria macrosepala (Papaveraceae) aqse 83, 119 '87 Fumaria muralis (Papaveraceae) jpps 33, 16 '81 Fumaria officina lis (Papaveraceae) jnp 46, 433 '83 Fumaria spp. (Papaveraceae) nps 4, 257 '98

I the N-oxide: I Fumaritine N-oxide Alkaloid Fk-5 Fumaria indica (Papaveraceae) phy 31, 2869 '92 Fumaria kralikii (Papaveraceae) cjc 57, 53 '79

CH30

6-MeO 7-HO 2,5-MeO ,HO-benzyl Me THIQ Dehassiline

HO HO

D eh assia ku rz ii (Lauraceae) fit 62, 261 '91

109


CH30

6-MeO 7-HO 3,4-HO,HO-benzyl H IQ

HO

Turcomanine

(Berberidaceae) cnc 32, 59 '96

Be rberis turc oma nica

6-MeO 7-HO 3,4-HO,HO-benzyl Me THIQ

OH

Compound unknown

Iwitha (6,N-Me) attack:

I (-)-Pessoine

Annona spinesc ens

HO

HO

(Annonaceae) jnp 59, 438 '96

OH OH

6-MeO 7-HO 3,4-HO,MeO-benzyl THIQ H

(R)(+ )- isomer: Ficus pachyrrachis

Norreticuline

(Moraceae) pm 59, 286 '93

(S)(-)-isomer: OH Annona reti culata (Annonaceae) phy 26, 3235 '87 Argemone platy ceras (Papaveraceae) phy 26, 3235 '87 Be rberis aggr egata (Berberidaceae) phy 26,3235 '87 Be rber is aris tata (Berberidaceae) phy 26, 3235 '87 Berberis bean iana (Berberidaceae) phy 26, 3235 '87 Berberis koe tineana (Berberidaceae) phy 29,3491'90 Be rberis stolonifera (Berberidaceae) phy 26,3235 '87 Be rberis wilsoniae var. subcaulialata (Berberidaceae) phy 26, 3235 '87


110

Chelidonium majus (Papaveraceae) phy 26, 3235 '87 Cissampelos pareira (Menispermaceae) phy 26, 3235 '87 Corydalis cava (Papaveraceae) phy 26, 3235 '87 Corydalis meifolia (Papaveraceae) tet 42,675 '86 Eschscholzia californica (Papaveraceae) phy 26,3235 '87 Eschscholzia lobbii (Papaveraceae) phy 26, 3235 '87 Fumaria parviflora (Papaveraceae) phy 26,3235 '87 Papaver somniferum (Papaveraceae) phy 26,3235 '87 Thalictrum dipterocarpum (Ranunculaceae) phy 26, 3235 '87 Thalictrum flavum (Ranunculaceae) phy 26, 3235 '87 Thalictrum foetidum (Ranunculaceae) phy 26, 3235 '87 Thalictrum rugosum (Ranunculaceae) phy 26, 3235 '87

I with a (2,4a) attack: I Norsinoacutine HO

Croton Croton Croton Croton Croton

balsamifera (Euphorbiaceae) llyd 32, 1 '69 bonplandianus (Euphorbiaceae) phy 20,683 '81 flavens (Euphorbiaceae) rlq 1, 140 '70 CH 30 linearis (Euphorbiaceae) llyd 32, 1 '69 plumieri (Euphorbiaceae) phy 8, 777 '69

0

CH30

Norsalutaridine (+)-isomer:

Papaver pseudo-orientale (Papaveraceae) jnp 51, 802 '88

HO

isomer not specified: Croton hemiargyreus (Euphorbiaceae) phy 47, 1445 '98

and a hydrogenated double bond at the 8,8a-position :

CH30 0

8/14-Dihydronorsalutaridine Croton echinocarpus (Euphorbiaceae) llyd 32, 1 '69 Croton linearis (Euphorbiaceae) llyd 32, 1 '69 Croton plumieri (Euphorbiaceae) phy 8, 777 ' 69

CH30 HO

CH30 0

111

Structural Index - 6,7-MeO,HO-Substituted OH

I witha (6,4a) attack I

CH30 H-Norpallidine

Fum aria vaillantii

(Papaveraceae)

phy 15, 1802 '76

CH30

o

I witha (6,8)attackl Norisoboldine Laurelli ptine

CH30 HO

A nn on a sa lz m an ii (Annonaceae) je 36,39 '92 A rt ab otr ys m on te ir o ae (Annonaceae) pa 4, 72 '93 B eil sc hm ied ia spp. (Lauraceae) het 9,903 '78 Cassytha pubescens (Lauraceae) het 9,903 '78 CH30 Cassytha racem osa (Lauraceae) het 9, 903 '78 Cocculus laurifolius (Menispermaceae) cnc 27, 73 '91 Il li g er a p en ta phyll a (Hemandiaceae) jnp 48,835 '85 L it se a a cu m in ata (Lauraceae) cpj 46, 299 '94 Lit se a t ri fl o ra (Lauraceae) aqsc 76, 171 '80 Lit se a spp. (Lauraceae) ajc 22, 2259 '69 M on od ora te n uif oli a (Annonaceae) daib 45, 520 '84 N ec ta nd ra ri gid a (Lauraceae) jnp 43,353 '80 N eo li ts ea ze yl anic a (Lauraceae) het 9,903 '78 O cotea caes ia (Lauraceae) phy 28, 3577 '89 Ziz ip h us ju ju ba (Rhamnaceae) kps 13,239 '77

CH30

6-M eO 7-HO 3,4-HO,MeD-benzyl Me

OH

THIQ

HO

Reticuline

W~

CH~

A rg em o negra cil enta (Papaveraceae) joe 34, 555 '69 M ac hi/ us du th ei (Lauraceae) jcp 2, 157 '80 O coteavelloziana (Lauraceae) phy 39,815 '95 Papaverbradeatum (Papaveraceae) phy 16, 1939 '77

OH

112


(+)(S)-isomer: Alse odaphn e arc hboldiana (Lauraceae) het 9, 903 '78 Aniba can elilla (Lauraceae) cjc 71, 1128 '93 Annon a cherim olia (Annonaceae) jnp 48, 151 '85 Annon a spp. (Annonaceae) jnp 48, 151 '85 Arg emo ne spp. (Papaveraceae) joe 34, 555 '69 Artabotrys mon teiroae (Annonaceae) pa 4, 72 '93 Artabotrys ven ustu s (Annonaceae) jnp 49, 602 '86 Be rbe ris spp. (Berberidaceae) phy 29, 3505 '90 Bon gar dia chrysogo num (Berberidaceae) jnp 52,818 '89 Cananga odorata (Annonaceae) jccs 46, 607 '99 Ceratocapnos palaestinus (Papaveraceae) jnp 53, 1006 '90 Cinnamomum spp. (Lauraceae) het 9, 903 '78 Corydalis spp. (Papaveraceae) ijcdr 26, 155 '88 Cryptocarya spp. (Lauraceae) het 9, 903 '78 Cymbopetalum brasiliense (Annonaceae) pm 50, 517 '84 De smos tieb agh ien sis (Annonaceae) jnp 45,617 '82 Eschscholzia californica (Papaveraceae) lac 6, 555 '90 Fumaria capreolata (Papaveraceae) per 4, 96 '85 Glaucium grandiflorum (Papaveraceae) apt 43, 89 '01 Glaucium fimbrilligerum (Papaveraceae) cnc 16, 177 '80 Glossocalyx brevipes (Monimiaceae) jnp 48, 833 '85 Guatteria goudotiana (Annonaceae) phy 30,2781 '91 He rna ndia spp. (Hernandiaceae) bmnh 2, 387 '80 Illig era par viflora (Hernandiaceae) cty 22, 393 '91 Lau rus nob ilis (Lauraceae) jnp 45, 560 '82 Leontice leon tope talum (Berberidaceae) jnp 49, 726 '86 Lin dera spp. (Lauraceae) jnp 47, 1066 '84 Litsea spp. (Lauraceae) ajc 43, 1949 '90 Magn olia spp. (Magnoliaceae) pm 48, 43 '83 Mo noc yclanthus vig nei (Annonaceae) jnp 54,1331 '91 Ne ctan dra salic ifolia (Lauraceae) jnp 59, 576 '96 Ne olitse a spp. (Lauraceae) jnp 47, 1062 '84 Papaver somniferum (Papaveraceae) kps 12, 750 '76 Papaver spp. (Papaveraceae) phy 25, 2639 '86 Peumus boldus (Monimiaceae) jps 57,1023 '68 Phoebe minutiflora (Lauraceae) cpj 49, 217 '97 Polyalthia acuminata (Annonaceae) jnp 45, 471 '82 Rollinia emarginata (Annonaceae) jnp 49,717 '86 Siparuna tonduziana (Monimiaceae) pm 56, 492 '90 Sparattanthelium uncigerum (Hernandiaceae) jnp 48, 333 '85 Stephania spp. (Menispermaceae) cpb 45, 470 '97


Thalictrum minus chemovar b (Ranunculaceae) llyd 41, 257 '78 Thalictrum spp. (Ranuneulaeeae) jnp 45, 252 '82 Uvaria spp. (Annonaeeae) nm 51, 272 '97 Xy lopia spp. (Annonaeeae) pm 30, 48 '76

(-)(R)-isomer: Aniba spp. (Lauraceae) bse 8, 51 '80 Anom ianthu s dulcis (Annonaeeae) bse 26, 139 '98 Croton celtidifolius (Euphorbiaeeae) pm 63, 485 '97 Ficus pachyrrachis (Moraceae) pm 59, 286 '93 Papaver spp. (Papaveraceae) phy 25, 2639 '86 isomernot specified: (Ranuneulaeeae) ene 20, 760 '84 Aconitum zera vschanicum Aniba muca (Lauraeeae) rbq 13, 19 '96 Anno na squamosa (Annonaceae) epj 46, 439 '94 Anomianthus dulcis (Annonaceae) bse 26, 139 '98 Arcto mecon humile (Papaveraceae) bse 18, 45 '90 Chelidonium majus (Papaveraceae) jcspt I, 1140 '75 Cinnamomum camphora (Lauraeeae) het 9, 903 '78 Cocculus laurifolius (Menispermaeeae) tet 36, 3107 '80 Corydalis spp. (Papaveraceae) ene 20, 245 '84 (Euphorbiaceae) pa 10, 254 '99 Croton hemiargyreus var. gymnodiscus Cryptocarya longifolia (Lauraeeae) abs 11 Dicentra peregrina (Papaveraceae) ene 20, 74 '84 Doryph ora sassafras (Monimiaeeae) llyd 37, 493 '74 Erythrina arborescens (Fabaeeae) yz 93,1617 '73 Fumaria vaillantii (Papaveraceae) ene 17, 437 '81 Glaucium spp. (Papaveraceae) cne 19, 714 '83 Guatteria spp. (Annonaeeae) pmp 18, 165 '84 Gyrocarpus american us (Hernandiaceae) jnp 49, 101 '86 Hernandia guian ensis (Hemandiaeeae) pm 50, 20 '84 Hydrastis canadensis (Ranuneulaeeae) llyd 33s, 1 '70 LAurelia philippiana (Monimiaeeae) phy 21,773 '82 LAuroba sidium lauri (Exobasidiaeeae) jpp 40, 801 '88 Litsea spp. (Lauraeeae) epj 46, 299 '94 Machilu s thunb ergii (Lauraeeae) het 9, 903 '78 Magnolia salicif olia (Magnoliaceae) pm 51, 291 '85 Ocotea spp. (Lauraeeae) rlq 11, 110 '80 Oropheahexandra (Annonaeeae) bse 27, 111'99 Oxandra major (Annonaeeae) phy 26, 2093 '87 Pachygone ovata (Menispermaeeae) jnp 42, 399 '79

113


114

Papaver spp. (Papaveraceae) cnc 24, 475 '89 Phoebe spp. (Lauraceae) jca 667, 322 '94 Phylica rogersii (Rhamnaceae) llyd 33s, 1 '70 Polyalthia nitidissima (Annonaceae) pm 49,20 '83 Sassafras albidum (Lauraceae) llyd 39, 473a '76 Thalictrum pedunculatum (Ranunculaceae) izk 21, 246 '88 X ylop ia fr utes ce ns (Annonaceae) pmp 16, 253 '82 X ylop ia pa pu an a (Annonaceae) npl 6, 57 '95

(Beware of the spelling without the final "e." Reticulin is a connective tissue protein.)

I the N-oxide:1 Reticuline N-oxide (+)-isomer: Corydalis pseudoadunca (Papaveraceae) cnc 21, 807 '86 M ag no lia sa lic iio lia (Magnoliaceae) pm 48, 43 '83 isomer not specified: Pachygone ovata (Menispermaceae)

jnp 42, 399 '79

CH30

I with a 3,4-ene: I a-Dehydroreticuline

HO

Croton hemiargyreus (Euphorbiaceae) pa 10, 254 '99 Licar ia ar me ni ac a (Lauraceae) bps 8, 28 '85

CH30 OH I with

a (2,N-Me) attack:

I

Scoulerine Aurotensine

CH30 HO

OH (d1)-Scoulerine Aurotensine: Giaucium oxylobum (Papaveraceae)

llyd 33s, 1 '70

OCHs


(R)(+ )-Scoulerine: Corydalis Corydalis Corydalis Corydalis Corydalis Corydalis

bulleyana (Papaveraceae) pm 52, 193 '83 caucasica (Papaveraceae) ijcd 27, 161 '89 incisa (Papaveraceae) cpb 24, 2859 '76 rutifolia (Papaveraceae) ijcdr 26, 155 '88 scouleri (Papaveraceae) bull 1 solida ssp. brachyloba (Papaveraceae) jcsp 13, 63 '91

(5)(-)-Scoulerine: Argemone albiflora (Papaveraceae) ecce 38, 3312 '73 (Papaveraceae) ecce 39, 2491 '74 Argemone polyanthem os Corydalis claviculata (Papaveraceae) phy 24, 585 '85 Corydalis decumbens (Papaveraceae) jcps 4, 57 '95 Corydalis gigantea (Papaveraceae) kps 12, 754 '76 (Papaveraceae) pm 57, 156 '91 Corydalis hsuchowensis Corydalis incisa (Papaveraceae) phy 13, 2620 '74 Corydalis intermedia (Papaveraceae) ecce 54,2009 '89 (Papaveraceae) yz 94, 844 '74 Corydalis koidzumiana Corydalis majori (Papaveraceae) pmp 22, 219 '88 Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89 Corydalis ochroleuca (Papaveraceae) cjc 47, 1103 '69 Corydalis omeiensis (Papaveraceae) tcyyk 4, 7 '92 Corydalis saxicola (Papaveraceae) zx 24, 289 '82 Corydalis severtzovii (Papaveraceae) cnc 11, 826 '75 Corydalis stewartii (Papaveraceae) pm 58, 108 '92 Corydalis vaginans (Papaveraceae) cnc 12, 118 '76 Disepalum pulch rum (Annonaceae) phy 29, 3845 '90 Eschscholzia californica strain bb (Papaveraceae) tet 47, 5945 '91 Eschscholzia lobbii (Papaveraceae) ecce 41,2429 '76 Eschscholzia oregana (Papaveraceae) ecce 40, 1095 '75 Fumaria asepala (Papaveraceae) ijcdr 24, 105 '86 Fumaria bella (Papaveraceae) jnp 49, 178 '86 Fumaria capreolata (Papaveraceae) jnp 48, 670 '85 Fumaria judaica (Papaveraceae) guefd 1, 15 '84 Fumaria kralikii (Papaveraceae) ijcdr 26, 61 '88 Fumaria petteri ssp. thuretii (Papaveraceae) ijcdr 26, 61 '88 Fumaria vaillantii (Papaveraceae) phy 22, 2073 '83 (Papaveraceae) cnc 16, 177 '80 Glaucium fimbrilligerum (Papaveraceae) ecce 45, 914 '79 Hunnemannia fuma riaefo lia Hypecoum procu mbens (Papaveraceae) jnp 46, 414 '83 Sarcocapnos crassifolia speciosa (Papaveraceae) phy 28,251 '88 Sarcocapnos enneaphylla (Papaveraceae) phy 30, 1005 '91

115

116


Sarcocapnos saetabensis (Papaveraceae) phy 30,2071 '91 Stephania cepharantha (Menispermaceae) cpb 45, 470 '97

isomer not specified: An no na pa ludo sa (Annonaceae) pmp 22, 159 '88 Ar ge mo ne alba (Papaveraceae) cnc 22, 189 '86 Ar ge mo ne al biflora (Papaveraceae) cnc 22,742 '87 Ar ge mo ne hy br ida (Papaveraceae) cnc 22, 189 '86 Ar ge mo ne me xi ca na (Papaveraceae) cnc 22, 189 '86 Ar ge mo ne or ch ro leu ca (Papaveraceae) kps 6, 798 '86 B erbe ris va ldiv iana (Berberidaceae) fit 64, 378 '93 Chelidonium majus (Papaveraceae) pm 60,380 '94 Cop tis japonica (Ranunculaceae) phy 32, 659 '93 Corydalis bungeana (Papaveraceae) pm 53,418 '87 Corydalis gortschakovii (Papaveraceae) cnc 20, 245 '84 Corydalis impatiens (Papaveraceae) patent 3 Corydalis ochotensis (Papaveraceae) jcspt I, 390 '77 Corydalis pseudoadunca (Papaveraceae) cnc 21, 807 '86 Corydalis repens (Papaveraceae) yhtp 17, 3 '82 Corydalis soiida (Papaveraceae) guefd 5, 9 '88 Corydalis stricia (Papaveraceae) kps 19, 461 '83 Corydalis tashiroi (Papaveraceae) pm 67, 423 '01 Cryptocarya longifolia (Lauraceae) abs 11 D icen tra pe regr ina (Papaveraceae) cnc 20,74 '84 D icen tra spec iabi lis (Papaveraceae) cnc 20,74 '84 Fumaria capreolata (Papaveraceae) ijcd 23, 161 '85 Fumaria densiflora (Papaveraceae) ecce 61, 1064 '96 Fumaria [udaica (Papaveraceae) ijcd 22, 181 '84 Fumaria officinalis (Papaveraceae) cjc 47, 1103 '69 Fumaria parviflora (Papaveraceae) cnc 18, 608 '82 Fumaria oaillantii (Papaveraceae) cnc 17,437 '81 jnp 48, 670 '85 Fumaria spp. (Papaveraceae) Glaucium fimbrilligerum (Papaveraceae) cnc 19,464 '83 Glaucium oxylobum (Papaveraceae) ecce 50, 854 '84 Glaucium squamigerum (Papaveraceae) ecce 49, 1318 '84 Glaucium spp. (Papaveraceae) ecce 50,854 '84 M ah on ia aquiiolium (Berberidaceae) cp 39,537 '85 N an di na do me sti ca (Berberidaceae) patent 1 Papaver argemone (Papaveraceae) ecce 53,1845 '88 Papaver atlanticum Ball (Papaveraceae) ecce 51, 2232 '86 Papaver bracteatum (Papaveraceae) IT 24, 400 '88 Papaver confine (Papaveraceae) ecce 54, 1118 '89


117

Papaver cylindricum (Papaveraceae) pm 46,175 '82 Papaver fugax (Papaveraceae) kps 4, 559 '88 Papaver lecoquii (Papaveraceae) ecce 46, 2587 '81 Papaver litwinowii (Papaveraceae) ecce 46, 1534 '81 Papaver orientale (Papaveraceae) ecce 56, 1534 '91 (Papaveraceae) ecce 59, 1879 '94 Papaver pinnatifidum Papaver rhoeas var. chelidonioides (Papaveraceae) ecce 54,1118 '89 Papaver setigerum (Papaveraceae) ecce 61, 1047 '96 (Papaveraceae) ecce 55, 1812 '90 Papaver stevenianum Papaver tauricolum (Papaveraceae) phy 19, 2189 '80 Papaver triniaejolium (Papaveraceae) pm 49, 43 '83 Stylophorum lasiocarpum (Papaveraceae) ecce 56, 1116 '91 Stylophorum diphyllum (Papaveraceae) ecce 49, 704 '84 Thalictrum tuberosum (Ranunculaceae) phy 33,1431 '93

landaromatization of the c-ring: I

CHsO

Tetradehydroscoulerine

HO

OH

Pseuduvaria indochinensis (Annonaceae) phy 27, 4004 '88 Thalictrum tuberosum (Ranunculaceae) phy 33,1431 '93

OCHs

OH

!with a (2,3) attack: I

CHsO Munitagine

HO Argemone hybrida (Papaveraceae) cnc 22, 189 '86 Argemone gracilenta (Papaveraceae) jnp 46, 293 '83 Argemone mun ita (Papaveraceae) jnp 46, 293 '83 Argemone platyce ras (Papaveraceae) kfz 22, 580 '88 Argemone pleiacantha (Papaveraceae) phy 8, 611 '69

alsounder: 7,8 MeO HO R Me THIQ R = 3,4-MeO,Ho-benzyl (6,3) attack

OC H s

118



Salutaridine Floripavine Salutarine Sinoacutine Sinacutine CHsO

(+ )-Salutaridine

Floripavine: HO Croton balsamifera (Euphorbiaceae) rlq 1,140 '70 Croton plumieri (Euphorbiaceae) rlq 1,140 '70 Croton spp. (Euphorbiaceae) llyd 32, 1 '69 Glaucium fimbrilligerum (Papaveraceae) CHsO jnp 61, 1564 '98 Glaueium flavum (Papaveraceae) phy 27, 1021 '88 Glaucium spp. (Papaveraceae) jnp 61, 1564 '98 Papaver bracteatum (Papaveraceae) ecce 50, 1215 '85 Papaver fugax (Papaveraceae) jsiri 7, 263 '96 Papaver orientale (Papaveraceae) book 4 Papaver pseudo-orientale (Papaveraceae) ecce 51, 1752 '86 Papaver somniferum (Papaveraceae) book 4 Papaver triniifolium (Papaveraceae) pm 49, 43 '83 Papaver spp. (Papaveraceae) dsa 7, 93 '83 Sarcocapnos crassifolia (Papaveraceae) phy 30, 1175 '91 Sarcocapnos saetabensis (Papaveraceae) phy 30,1175 '91

o

(-)-Salutaridine CHsO (-)-Sinoacutine Sinacutine: Ar ta bo try s un cina tu s (Annonaceae) jnp 64, 1157'01 HO B erbe ris bu xifol ia (Berberidaceae) daib 44,1458 '83 B erbe ris ili eifo lia (Berberidaceae) het 43,949 '96 Cassytha pubescens (Lauraceae) het 9, 903 '78 CHsO Ceraiocapnos palaestinus (Papaveraceae) o jnp 53, 1006 '90 Cocculus carolinus (Menispermaceae) jps 61, 1825 '72 Corydalis koidzumiana (Papaveraceae) yz 94,844 '74 Corydalis majori (Papaveraceae) pmp 22, 219 '88 Corydalis ochotensis var. raddeana (Papaveraceae) jcspt I, 390 '77 Corydalis stewartii (Papaveraceae) pm 58, 108 '92 Croton flavens (Euphorbiaceae) llyd 32, 1 '69 Croton lechleri (Euphorbiaceae) pm 62, 90 '96

119


(Papaveraceae) jps 65, 755 '76 Glaucium contortuplicatum (Berberidaceae) yz 94, 1149 '74 Nandin a dom estica Ocotea brachybotra (Lauraceae) tl1631 '76 Peumus boldus (Monimiaceae) fit 54, 175 '83 Platycapnos saxicola (Papaveraceae) phy 30,3315 '91 Stephania brachyandra (Menispermaceae) tcyyk 4, 11 '92 Stephania cepharaniha (Menispermaceae) bpb 22, 268 '99 Stephania dicentzinifeza (Menispermaceae) zh 15, 8 '84 Stephania dielsiana (Menispermaceae) zh 14, 57 '83 Stephania elegans (Menispermaceae) ijnp 42, 147 '80 Stephania epigaea (Menispermaceae) nyx 5,203 '85 Stephania graciienia (Menispermaceae) ijnp 3,8 '87 Stephania micrantha (Menispermaceae) yx 16, 557 '81 Stephania officinarum (Menispermaceae) zx 32, 368 '90 Stephania pierrei (Menispermaceae) jnp 56, 1468 '93 (Menispermaceae) zx 31, 296 '89 Stephania yunnanensis Strychnopsis thouarsii (Menispermaceae) bse 23, 679 '95 (dll-Salutaridine

(structure the same as (+)-Salutaridine) (dll-Salutarine: Croton salutaris (Euphorbiaceae) phy 20, 543 '81 isomernot specified: Antizom a angu stifolia (Menispermaceae) jnp 51, 584 '88 Croton linearis (Euphorbiaceae) rlq 1, 140 '70 Sinomenium acutum (Menispermaceae) llyd 33s, 1 '70 Thalictrum foetidum (Ranunculaceae) pm 56,337 '90

(theN-oxide: I

(+)-Salutaridine

Papaverbracteatum

(Papaveraceae)

N-oxide pm 58, 368 '92

anda hydrogenated double bond atthe8,8a-position :

CHsO

HO (-)-8,14-Dihydrosal utaridine

CHsO Crotondiscolor (Euphorbiaceae) llyd 32, 1 '69 Crotonechinocarpus (Euphorbiaceae) llyd 32, 1 '69 Crotonlinearis (Euphorbiaceae) llyd 32, 1 '69

0


120

phy 8, 777 '69 Croton plumieri (Euphorbiaceae) ref 16, 45 '82 Croton stenophyllus (Euphorbiaceae) bydx 23, 235 '91 Sinomenium acutum (Menispermaceae) cty 13, 1 '82 Stephania brachyandra (Menispermaceae)

CH30

(-)-Ocobotrine pm 64, 58 '98 He rnan di a vo yron ii (Hernandiaceae) Ocotea brachybotra (Lauraceae) tl 1631 '76 Thalictrum [auriei (Ranunculaceae) jnp 62, 803 '99

HO

CH30

o I and

hydrogenated

double bonds:

I

Tetrahydrosinacutine Ocotea brachybotra (Lauraceae)

CH30 HO

fes 32, 767 '77

o I with

a (2,8) attack:

I

CH30

Corytuberine

HO Ac on itu m spp. (Ranunculaceae)

HO

ecce 60, 1034 '95 Ac taea spicaia (Ranunculaceae) CH30 ecce 60, 1034 '95 ecce 52, 804 '87 Ad on is spp. (Ranunculaceae) An no na ch erim ol ia (Annonaceae) jnp 48, 151 '85 ecce 52, 804 '87 Aq uilegia spp. (Ranunculaceae) ecce 52, 804 '87 Ar ist oloc hia cle ma tit is (Aristolochiaceae) ecce 52, 804 '87 Caltha palustris (Ranunculaceae) pm 60, 380 '94 Chelidonium majus (Papaveraceae) fit 63, 282 '92 Cissampelos pareira (Menispermaceae) ecce 52, 804 '87 Clematis recta (Ranunculaceae) ecce 52, 804 '87 Consolida regalis (Ranunculaceae) tcyyk 9, 37 '97 Corydalis dasyptera (Papaveraceae) cnc 13, 702 '77 Corydalis gortschakovii (Papaveraceae) ecce 54, 2009 '89 Corydalis nobilis (Papaveraceae)

616


Journal Names Appendix

CODE

JOURNAL NAME

aa aabc aajps aaqa abb abc abf abs ac acc accc acr acre acs acssb acv adq afb aim ajb ajc ajps akz al

Acta Amazonica Anales Acad. Brasil Cienc. Al-Azhar Journal of Pharm. Sci. An. Asoc. Quimica Argentina Arch. Biochem. Biophys. Agr. Biol, Chern. Ann. Bot. Fenn. (see ABSTRACTS below) Anal. Chern. Acta Crystallog., Commun. Acta Crystallog., Sec. C Commun. Anticancer Research Acgc Chern. Res. Commun. Acta Chimica Scandinav. Acta Chimica Scandinav., Ser. B Acta Gent. Venze. Anales De Quimica Acta Farm. Bonaerense Annals of Internal Medicine American Journal of Botany Australian Journal of Chemistry Alexandria Journal of Pharm. Sci. Arm. Khim. Zh. Acta Leidensia Arch. Pharm. (Germany) Ann. Pharm. France Acta Pharm. Jugosl. Acta Pharm. Nord. Acta Pol. Pharm. (Poland) Archives of Pharm. Res. Acta Pharm. Suecica Acta Pharm. Turc. Arch Pharm. (Weinheim) An.Quim. An. Quim. Ser. C

ap apf apj apn app apr aps apt apw aq aqsc


arch aua aup babf bbb be bemm besj ber bfs bgac bio bkcs bmel bmnh book bp bpb bps br bs bscq bs&e bscf bscq bsp bsrs bull bydx

CA cb cc

cccc cel cct cf chern chim chr chy ci

cjc cjr

Arch. Androl. Ann. Univ. Abidjan Ser. C Acta Univ. Palacki. Olomuc., Fac. Rerum Nat., Chern. Bol. Assoc. Brasil Farm. Biosci. Biotech. Biosci. Biomed. Chromatography Bull. Chinese Materia Medica Bull. Chern. Soc. Japan Chemische Berichte Bull. Fac. Sci., Assiut University Bulletin Georgian Acad. Sci. Biokhimiya Bulletin Korean Chern. Soc. Bioorg. Med. Chern. Letters Bull. Mus. Natl. Hist. Nat. Sect. B (see BOOKS below) Biochem. Pharmacology BioI. Pharm. Bulletin Bull. Pharm. Sci. Assiut Univ. Brain Res. Biosciences Biol, Soc. Chil. Quim. Biochem. Systematics & Ecol. Bull. Soc. Chim. Fr. Bull. de la Soc. Chilena de Quimica Bull. Sci. Pharmacology Bull. Soc. R. Sci. Leige (see BULLETINS below) Beijing Yike Daxue Xuebao Chemical Abstracts Chern. Ber. Chern. Communications Coll, Czee. Chern. Comm. Chinese Chern. Letters Contrib. Gent. Teenol. (Univ, Tee. Estado, Santiago) Cesk. Farm. Chemica Chimia Chromatographia Chung-Hua Yao Hsueh Tsa Chili Chern. Ind. (London) Canadian Journal of Chemistry Canadian Journal of Research

617

618

The Simple Plant Isoquinolines cl cnc

cp cpb cpj cra crab crhs crt ct cty cwf cwhp cytp cz

daib dant dban diss dmd dsa duj eb ejcp ejps exp fes ffbd fit fm

frm fzs gci go

gp guefd hca het hh

hhhp hkkuc hue

hx

Chern. Letters Chern. Nat. Compo Chern. Pap. Chern. Pharm. Bulletin Chinese Pharmaceut. Journal c. R. Acad. Sei., Ser. C C. R. Acad. Bulg. Sci. C. R. Hebd. Seances Acad. Sci., Ser. C Chern. Res. Toxicol. Clinical Toxicology Chung Ts'ao Yao Chih Wu Fen Lei Hsueh Pao Chih Wu Hsueh Pao Chung Yao Tung Pao Chern. Zvesti Dissertation Abstracts Int. b 001<1.Akad. Nauk Tadzh. SSR 001<1.Boig. Akad. Nauk (see DISSERTATIONS below) Drug Metab. Dispos. DogaSeriA Dirasat-Univ; Jordan Ser. b Economic Botany Eur. J. Clin. Pharmacology Egypt Journal of Pharm. Sci. Experientia Farmaco Ed. Sci. Fabad. Farm. Bilimler Derg. Fitoterapia Folia Med. Farmatsiya (Moscow) Faming Zhuanli Shenqing Gongkai Shoumingshu Gazetta Chimica Italiana Garcia Orta General Pharmacology Gazi. Univ. Eczacilik Fak. Derg. Helvetica Chimica Acta Heterocycles HerbaHung Hua Hsueh Hsueh Pao Hwahak Kwa Kongop Ui Chinbo Hacettepe Univ. Eczacilik Fak. Derg. Huaxue Xuebao


hyz iang ians iant id ijc ijcdr ijcs ijeb ijhc ijnp ijp ijps ik izk jacs jafc

jap jbas

jc jca jcc jccs jcp jcps jcpu jcr jcrs jcsc jcscc jcsp jcspt jcsr je jfp jhc jic jics jnp jnr jnsc joe

Huaxi Yaoxue Zazhi Izv. Akad. Nauk Gruz., Ser. Khim. Izv. Akad. Nauk SSSRSer. Khim. Izv. Akad. Nauk Tadzh. SSR Otd. Fiz. Mat. Khirn. Geol. Nauk Indian Drugs Indian Journal of Chern. Sec. B Int. Journal of Crude Drug Res. Indian Journal of Chern. Soc. Indian Journal of Exp. Biol. Indian Journal of Heterocycl. Chern. Indian Journal of Natural Products Int. Journal of Pharmacognosy Indian Journal Pharm. Sci. Iyakuhin Kenkyu Izv. Khim. Journal of American Chemical Society Journal of Agric. & Food Chern. Journal of Amer. Pharm. Ass. Sci. Ed. Journal of Bangladesh Acad. Sci. Journal of Chromatography Journal of Chromatography A Journal of Chern. Crystal. Journal of Chin. Chern. Soc. (Taipei) Journal of the Chern. Soc. of Pakistan Journal of Chinese Pharm. Science Journal of Chinese Pharm. University Journal of Chemical Research Journal of Chemical Research Synop. Journal of the Chemical Society-C Journal of the Chemical Society-Chern. Communications Journal of Chern. Soc. Pakistan Journal of the Chemical Society-Perkins Transactions Journal of Crystallographic & Spectroscopic Res. Journal of Ethnopharmacology Journal of Fac, Pharm. Istanbul Univ. Journal of Heterocyclic Chern. Journal of Inst. Chern. (Calcutta) Journal of the Indian Chern. Soc. Journal of Natural Products Journal of Neuroscience Research Journal of Natl. Sci. Council Sri Lanka Journal of Organic Chemistry

619

620 joe jp jpic jpp jpps ips jpsj jrim jscs jsiri kdr kfz kjp kps lac llyd lr Is mjps mjs nasb nat ncyh nei nl nm nmt npl nps nr

nyx oiz ojc

ornr pa patent paz pb pbl pebr

pc i pel

The Simple Plant Isoquinolines Journal of Ethnopharmacology Journal of Pharm. Journal of Proc. Inst. Chern. (India) Journal of Pharm. Pharmacol. Journal of Pharm. Pharmacol. Suppl. Journal of Pharmaceutical Science Journal of Pharm. Society Japan Journal of Res. Indian Med, Yoga Homeopathy Journal of Serb. Chern. Soc. Journal of Sci. Islamic Repub. Iran Kagoshima Daigaku Rigakubu Kiyo Sugaku Butsurigaku Kagaku Khim. Farm. Zh. Korean Journal of Pharmacognosy Khimiya Prirodnykh Soedinenii Liebigs Ann. Chern. Lloydia Lekarstv. Rasteniya Life Science Mansoura Journal of Pharm Sci. Malaysian Journal of Science National Applied Science Bulletin Nature Nan-Ching Yao Hsueh Yuan Hsueh Pao Neirokhimiya Neuroscience Letters Natural Medicine Natural Medicine, Tokyo Natural Products Letters Natural Products of Science no reference Nanjing Yixueyuan Xuebao Okayama Igakkai Zasshi Orient. Journal of Chemistry Org. Magn. Reson. Phytochemical Analysis (see PATENTS below) Pazhoohandeh(Tehran) Pharm. Bull. Pharm. Biol, (Netherlands) Prog. CIin. BioI. Res. Pharm. Chern. Journal Pharmacologist


pcr pes pet&oc pert phy phymed phzi pjps pjsr pm pmj pmp pms pnsc pp

pptp pr prs psj ptn pw

qn rbf rbp rbq

ref rcq rlq IT

ryz san sci sh

sp svs sy syn syx sz taxon tcdh tcyyk tet

Plant Cell Rep. Proceedings of the Chemical Society Plant Cell Tissue & Organ Culture Pertanika Phytochemistry Phytomedicine Pharmazie Pakistan Journal of Pharm. Sci. Pakistan Journal of Sci. Res. Planta Medica Pahlavi Med. Journal Planta Medica Phytother. Planta Medica Supp. Proceedeings of the National Sci. Council, Rep. China Plant Physiology Phytochem. Potential Trop. Plants Phytotherapy Research Phytotherapy Research Supp. Pharm. Soc. Japan Phyton (Horn, Austria) Pharm Weekbl. (Sci. Ed.) Quim.Nova Rev. Brasil Farm Rev. Brasil Plant Med. Rev. Boliv. Quimica Rev. Cubana Farm. Rev. Colomb. Quimica Rev. Latinoam. Quimica Rastit. Resur. Redai Yaredai Zhiwu Xuebao Soobshch. Akad. Nauk Gruz. SSR Science Saengyak Hakhoechi Sci. Pharm. Sb. Vys. Sk. Zemed. Praze, Fak. Agron., Rada A Synth. Commun. Synthesis Shenyang Yaoxueyuan Xuebao Shoyakugaku Zasshi Taxon Tap Chi Duoc Hoc Tianran Chanwu Yanjiu Yu Kaifa Tetrahedron

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tl tox tyhtc ws yfz yg yh yhc yhhp yhtp

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Tetrahedron-Asymmetry Turkish Journal of Chemistry Tetrahedron letters Toxicon Taiwan Yao Hsueh Tsa Chih Wakanyaku Shinpojumu Yaowu Fenxi Zazhi Yiyao Gongye Youji Huaxue Yakhak Hoe Chi Yao Hsueh Hsueh Pao Yao Hsueh Tung Pao Yaoxue Tongbao Yaoxue Xuebao Yakugaku Zasshi Zhongcaoyao Zhongyaocao Keji Z Pflanzenphysiol Zb. Prir. Nauke Zhiwu Xuebao Zhonggou Yaoke Daxue Xuebao Zhonggou Yaowu Huaxue Zazhi Zhonghua Yaoxue Zazhi Zhongguo Zhongyao Zazhi

ABSTRACTS abs 1

Abstr 23rd Annual Meeting American Society of Pharmacognosy, Aug. 1-5 (1982) Pittsburgh, PA: Abstr-26

abs2

Abstr Joint Meeting American Society of Pharmacognosy and Society for Economic Botany, July 13-17 (1981) Boston, MA :31-

abs3

Abstr Intemat Res Cong Nat Prod ColI Pharm UNC Chapel Hill, NC, July 7-12 (1985): Abstr-19

abs4

Proc 1st Int Coni Chern Biotechnol Biol Act Nat Prod (1981) B Atanasova(Ed) Bulgarian Acad Sci Sofia, 31:74-

abs 5

Proceedings of the 38th Asms Conference 'on Mass Spectrometry and Allied Topics: (1990)


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abs 6

Int Conf Chern Biotechnol Biol Act Nat Prod (Proc) 1st 31:95-97 (1981)

abs 7

Plant Tissue Cult Proc Int Congr Plant Tissue Cell Cult 5th (1982) :315-316

abs8

Tezisy Dokl Molodezhnaya (1976):59-60

abs9

Abstr Internat Res Cong Nat Prod Coll Pharm, UNC Chapel Hill, NC, July 7-12 (1985):Abstr-61

abs 10

Proc Fifth Asian Symposium on Medicinal Plants and Spices, Seoul, Korea, Aug. 20-24 (1984) Bh Han Os Han Yn Han and Ws Woo(Eds) 5:509-518

abs 11

Abstr 4th Asian Symp Med Plants Spices, Bangkok, Thailand, Sept. 15-19 (1980):170-

abs 12

Proc Int Symp Recent Adv Nat Prod Res, Seoul, Korea, Dec. 14-16 (1979):18-23

abs 13

Proc 25th Symp on the Chern of Nat Prod, Tokyo (1982) 25:353-360

abs 14

Biochem. Physiol. Alkaloide, Int. Symposium, 4th, (1972) Meeting Date 1969, 275-8. Publisher: Akad.-Verlag, Berlin, E. Germany.

abs 15

Revista de la Facultad de Ciencias Quimicas Universidad Nacional de la Plata 6, 75 (1930)

abs 16

Abstr 27th Annual Meeting American Society of Pharmacognosy, July 27-30 (1986), Ann Arbor, MI: Abstr-49

Konf Org Sint Bioorg Khim

BOOKS book 1

Scientific Basis of Traditional Chinese Medicine, Y. Lau & J.P.Fowler (Eds) p. 45 (1982)

The Simple Plant Isoquinolines

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