BAB I. Pendahuluan
Flav Flavon onoi oid d adal adalah ah golo golong ngan an feno fenoll alam alam yang yang ters terseb ebar ar luas luas dala dalam m tumb tumbuh uhan an.. Menu Menuru rutt perk perkir iraa aan n , kiraira-ki kira ra 2% dari dari selu seluru ruh h karb karbon on yang yang difotosintesis oleh tumbuhan atau sekitar 1.000.000.000 ton per tahun diubah menjadi flavonoid atau senyawa yang berkaitan dengannya. Diduga flavonoid sudah ada di alam ini telah cukup lama, yang terdapat pada ganggang hijau lebih 1 milyar tahun silam. Tidak ada senyawa yang begitu menyolok seperti flavonoid yang memberi keindahan dan kesemarakan pada bunga dan buah-buahan di alam, alam, misal misalnya nya flavin flavin membe memberi ri warn warna a kunin kuning g atau atau jingga jingga,, anto antosia sianin nin warna warna merah, merah, ungu ungu atau biru biru dan secara secara biolo biologis gis dia memain memainkan kan peran peranan an penting penting dalam proses penyerbukan penyerbukan pada tanaman oleh serangga. Pada mulanya para ahli ahli terta tertarik rik pada pada anto antosia sian, n, yang yang merup merupak akan an pigmen pigmen tumbu tumbuha han n flavo flavono noid. id. Kemudian Kemudian diketah diketahui ui pula pula bahwa bahwa dalam dalam buah-bu buah-buaha ahan, n, sayur-s sayur-sayu ayuran ran dan bijibijibijia bijian n menga mengand ndun ung g berba berbaga gaii jenis jenis senya senyawa wa flavo flavono noid. id. Disa Disampi mping ng seba sebaga gaii pigmen pigmen tumbu tumbuha han, n, flavo flavono noid id diketa diketahui hui pula pula berpe berpera ran n dalam dalam pertu pertumbu mbuha han, n, pertahanan diri dari serangan hama dan penyakit, tabir surya, dan sinyal kimia untuk berkomunikasi dengan lingkungannya. Bagi manusia golongan senyawa ini memberi memberi manfaat manfaat yang yang cukup cukup banyak banyak seperti seperti,, antioks antioksidan idan,, antiinfl antiinflamas amasi, i, immunosti immunostimula mulan, n, antikan antikanker ker,, antiviru antivirus s dan antimikro antimikroba. ba... Tanin Tanin yang yang termasuk termasuk golon golonga gan n seny senyawa awa ini tela telah h lama lama diguna digunaka kan n seba sebaga gaii peny penyama amak k kulit kulit dan dan pewarna kain. Berbagai komoditi penting seperti teh, coklat dan anggur, mutunya sangat ditentukan oleh warna maupun rasa yang berasal dari flavonoid yang terdapat didalamnya.
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Istilah flavonid yang diberikan untuk senyawa-senyawa fenol ini berasal dari kata flavon, yakni yakni nama nama dari dari sala salah h satu satu jenis jenis flavo flavono noid id yang yang terb terbes esar ar jumlahnya dan dan juga lazim ditemukan ditemukan . Flavono Flavonoid id terdapa terdapatt dalam dalam semua semua tumbuha tumbuhan n hijau hijau sehingg sehingga a pastila pastilah h ditemukan pada setiaap telaah ekstrak tumbuhan. Oleh karena itu, para ilmuwan perl perlu u
kir kiranya
untu ntuk
men mengetahu tahuii
cara
mengena genal, l,
men mengiso isolas lasi,
dan
mengidentifikasi bahan alam tersebut dalam berbagai bentuk. I.1 Kerangka dasar
Flavonoid Flavonoid merupakan merupakan senyawa senyawa dengan kerangka dasar mempunya m empunyaii 15 atom C, dua cincin benzen yang terikat pada suatu rantai propana sehingga susunannya adalah C 6 – C3 – C6. Susunan ini akan menghasilkan tiga jenis struktur, yaitu : 1,3 – diaril propane atau flavonoid, 1,2 – diaril propane atau isoflavonoid dan 1,1 – diaril propane atau neoflavonoid C3 C3 C3
C2
C2 C1
C1
C2 C1
FLAVONOID
ISOFLAVONOID
NEOFLAVONOID
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Contoh : 1. Flavonoid OH HO
O
O OH
O
O
OCH3
O
O
O
OH
FLAVON
KUERSETIN
KRANJIN
2. Isoflavonoid Isoflavonoid HO
O
O OH HO
OCH3
FEREIRIN O
O O
H3CO
O O O
OH
OCH3
CH2
O
OCH3
O
PTEROKARPIN
ROTENON
3. Neoflavonoid
H3CO
O
O
O
O O OH
HO
H3CO
O
O
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Kedua Kedua cinci cincin n aroma aromatik tik (benze (benzen) n) yang yang dihub dihubun ungka gkan n oleh oleh satu satuan an tiga tiga karbon dapat atau tidak dapat membentuk cincin ketiga. Untuk memudahkan maka cincin pertama benzen diberi indeks A, cincin benzen kedua indeks B dan cincin yang dapat terbentuk cincin C 3' 2' 8 9
B
2
O
3' 2'
5'
HO
1'
A
3
6 10 5
1
B
4
OH 4'
6'
C
OH
2
4'
1
7
3
5
6
A
5'
4
6'
O
O
Senyaw Senyawa a flavono flavonoid id terdiri terdiri atas atas beberapa beberapa jenis, jenis, bergan bergantung tung dari dari tingkat tingkat oksidasi dari rantai propane dari sitem 1,3 diaril propane. Dalam hal ini flavan mempunya mempunyaii tingkat tingkat oksidas oksidasii yang terenda terendah h sehingga sehingga senyawa senyawa ini diangga dianggap p sebagai senyawa induk dalam tatanama senyawa-senyawa turunan flavon .
O
FLAVAN
I.2 Asal usul Biogenetik
Spekulasi awal mengenai biosintesis flavonoid dijelaskan oleh Robinson (1936) mengatakan bahwa kerangka C 6 – C3 – C6.
dari flavonoid flavonoid berkaitan berkaitan
dengan dengan kerang kerangka ka C 6 – C3 dari dari fenilpro fenilpropan pana a yang yang mempunya mempunyaii gugus gugus fungsi fungsi
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alanin alanin dan tirosin, tirosin, bukann bukannya ya dianggap dianggap sebaga sebagaii senyaw senyawa a yang menurun menurunkan kan flavonoid melainkan hanya sebagai senyawa yang bertalian belaka. Pola Pola bios biosint intes esis is flavo flavono noid id perta pertama ma kali kali dius diusulk ulkan an oleh oleh Birch, yang yang menjela menjelaskan skan bahwa bahwa tahap tahap pertama pertama biosint biosintesi esis s flavonoi flavonoid d suatu suatu unit C 6 – C3 berko berkombi mbina nasi si denga dengan n 3 unit unit C 2 menghas menghasilka ilkan n unit C 6 – C3 – (C2+C2+C2). Berdasarkan atas usul tersebut maka biosintesis dari flavonoid melalui 2 jalur bisosint bisosintesis esis yaitu yaitu poliket poliketida ida (asam (asam asetat asetat atau atau mevalona mevalonat) t) dalam dalam membentu membentuk k cincin A berkondensasi 3 molekul unit asetat, sedang cincin B dan tiga atom karbon dari rantai propana berasal dari jalur fenilpropana (shikimat). Selanju Selanjutny tnya, a, sebaga sebagaii akibat akibat dari dari berbaga berbagaii perubah perubahan an yang yang disebabk disebabkan an oleh enzim, ketiga atom karbon dari rantai propana dapat menghasilkan berbagai gugus gugus fungs fungsi, i, sepe seperti rti ikata ikatan n rangk rangkap ap,, gugu gugus s hidro hidroks ksil, il, gugu gugus s karbo karbonil nil dan dan sebagainya. Pokok-pokok biosintesis flavonoid
HO
O HO
OH
O OH
O OH
FLAVANON
Pembe mbentuka ukan fenilpropanoid fenilpropanoid (C
KHALKON
flav lavonoid noid
dimul imula ai
dengan gan
memp mempe erpa rpanjang jang
unit nit
C ) yang yang bera berasa sall dari dari turuna turunan n sinam sinamat at sepe seperti rti asam asam p-
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juga berperan berperan sebagai sebagai senyawa senyawa antara dalam biosintesis biosintesis berbagai berbagai jenis flavanoid lainnya OH
OH
OH H
HO
HO
O
OH
HO
O
[O]
OH
OH
O
Flavanon
O
O
OH
O
Khalkon
OH HO
Ha
O b
a
HO
O
+OH+
OH
OH
H
OH
O
OH
O [O]
a
+
-H
-H+
Flavanonol
b
H
OH HO
O
OH HO
O
OH OH
OH HO
O
OH
O
OH
Flavon
OH
O
OH
O
Auron
Flavonol
H HO
O
HO
O
O
OH
O
H
OH
O OH
Isoflavon
Katekin
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Biosintesis Antosianidin dan Katekin (Haslam )
I.3 Fungsi flavonoid pada tumbuhan 1. Fungsi penyerbukan. Flavonoid termasuk pigmen yang penting pada
tumbuhan. Warna jingga, merah, biru dan ungu pada bunga dan buah pada umumnya umumnya disebabk disebabkan an oleh oleh flavono flavonoid. id. Warna Warna pada pada bunga bunga adalah adalah salah salah satu fakto faktorr yang yang menar menarik ik leba lebah, h, kupu kupu-ku -kupu pu,, buru burung ng dan dan hewa hewan n lainn lainnya ya untuk untuk melakukan penyerbukan. Burung akan lebih menyukai warna merah, sedang lebah lebih menyukai warna biru dan juga dapat melihat di daerah ultraviolet. 2. Fungsi Fungsi pengatur pengatur tumbuh. tumbuh. Flavonoid secara tidak langsung berperan
sebagai sebagai zat pengatu pengaturr tumbuh tumbuh melalui melalui sistem sistem IAA (Indole Acetic Acid) – IAA Oxidase. Secara in vitro, senyawa flavonoid kuersetin dapat menghambat enzim
IAA – Oxidae, yang berarti kuersetin secara tidak langsung dapat meningkatkan pertumbuhan. Sen
flav
id dapat dapat pula berfung berfungsi si seb
i ”feeding deterrent ” ”
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lingkungannya, tumbuhan tumbuhan 3. Zat alelopati. Dalam berinteraksi dengan lingkungannya, menggunakan sinyal berupa senyawa kimia.Pada tahun 1986, secara hampir bersamaan, para ahli dari berbagai laboratorium di dunia melaporkan bahwa simbiosis antara antara tumbuhan tumbuhan polong-polongan polong-polongan dengan bakteri bakteri marga Rhizobium dipicu oleh sinyal kimia berupa senyawa flavonoid yang dikeluarkan oleh akar tumbuhan. tumbuhan. Sejak tahun 1982, ahli ekologi sudah mengetahui mengetahui tumbuhan “ Spotted knapweeds” (Centaurea maculosa Lam.) mengeluarkan senyawa alelopati yang
dapat menghambat pertumbuhan tumbuhan lain di sekitarnya, baru tahun 2001 diketahui bahwa senyawa tersebut adalah (-) – katekin, suatu senyawa flavonoid golongan flavan yang sekarang diteliti untuk dikembangkan menjadi herbisida alam. 4. Tabir surya. Rusaknya ozon di lapisan stratosfir, terutama di daerah
deka dekatt Kutub Kutub Selat Selatan an,, menye menyeba babk bkan an tumbu tumbuha han n menga mengalam lamii ceka cekaman man sinar sinar ultr ultrav avio iole lett B (UVB (UVB). ). Pene Peneli liti tian an pada pada seje sejeni nis s sema semang nggi gi di Sela Seland ndia ia Baru Baru memperliha memperlihatkan tkan bahwa bahwa tumbuha tumbuhan n tersebu tersebutt mempunya mempunyaii toleran toleransi si yang yang tinggi tinggi terha terhadap dap sinar sinar UVB, UVB, adap adaptas tasii ini diseb disebab abka kan n denga dengan n penin peningk gkata atan n kada kadar r flavonoid dari tumbuhan.
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BAB II. Ekstraksi dan Isolasi II.1 Ekstraksi
Aglikon flavonoid flavonoid adalah polifenol polifenol dan karena itu mempunyai mempunyai sifat kimia senyawa fenol, yaitu bersifat agak asam sehingga dapat larut dalam basa. Harus diingat, bila dibiarkan dalam larutan basa dengan oksigen banyak yang akan terurai karena mengandung banyak oksigen yang tidak tersulih atau suatu gula. Senya Senyawa wa flavo flavonoi noid d merup merupak akan an senya senyawa wa polar polar,, kepo kepolar laran an ini ini akan akan berbeda-beda berbeda-beda terhadap berbagai berbagai pelarut sehingga harus diperhatikan diperhatikan dengan menggunakan pelarut yang sesuai kepolaran flavonoid yang akan diekstraksi. Umumnya Umumnya flavono flavonoid id larut larut dalam dalam pelarut pelarut-pel -pelarut arut polar polar sepert sepertii etanol, etanol, metanol metanol,, butanol, butanol, aseton, aseton, dimetil dimetil sulfoks sulfoksida, ida, dimetilfo dimetilformami rmamida, da, air dan lain-lai lain-lain. n. Dalam Dalam bentuk glikosida karena adanya gula yang terikat pada flavonoid menyebabkan
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Baha Bahan n sega segarr merup merupak akan an baha bahan n awal awal yang yang ideal ideal untuk untuk menga mengana nalis lisis is flavono flavonoid, id, walaupun walaupun bahan bahan yang yang kering kering
dan tersimpa tersimpan n lama mungkin mungkin masih
tetap memberikan hasil yang baik. Bila menggunakan bahan tumbuhan segar, setelah cuplikan dipilih untuk dianalisis maka sisanya dianjurkan agar segara secepatnya dikeringkan untuk mencegah kerja dari enzim. Setel Setelah ah menimb menimban ang g seba sebagia gian n baha bahan n tumbuh tumbuhan an yang yang telah telah digil digiling ing,, ekstr ekstrak aksi si palin paling g baik baik dilak dilakuka ukan n dalam dalam dua dua taha tahap; p; pert pertama ama denga dengan n pela pelarut rut metanol-air (9 : 1) dan kedua dengan metanol-air (1 : 1). Ekstrak kemudian dicampur dan diuapkan hingga volumenya menjadi sepertiga volume awal, atau hampir semua metanol menguap. menguap. Ekstrak yang diperoleh dapat dibabaskan dari senyawa senyawa yang yang kepola kepolarann rannya ya rendah rendah sepert sepertii lemak, lemak, terpena terpena,, klorofi klorofil, l, xantofil xantofil denga dengan n ekst ekstrak raksi si (dala (dalam m coro corong ng pisah pisah)) meng menggun gunak akan an pela pelarut rut heksa heksan n atau atau kloroform. Ekstraksi harus dilakukan beberapa kali dan lapisan air mengandung seba sebagia gian n besa besarr flavo flavonoi noid, d, sela selanju njutn tnya ya diker dikering ingka kan n pada pada teka tekana nan n rend rendah ah (rotapavor). Pemilihan pelarut tidak hanya tergantung pada kandungan zat aktif yang diselidiki, tetapi tergantung juga pada bagian mana substansi tersebut berada.
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atau atau bung bunga a janga jangan n diker dikering ingka kan n teta tetapi pi sege segera ra diger digerus us deng dengan an NeOH NeOH yang yang mengand mengandung ung 1% HCl pekat. pekat. Ekstra Ekstraksi ksi segera segera terjadi terjadi yang yang ditanda ditandaii dengan dengan adan adanya ya perub perubah ahan an warn warna a laruta larutan, n, kromat kromatog ograf rafii atau atau anali analisis sis spek spektro trosko skopi pi ekstr ekstrak ak dapa dapatt sege segera ra dilak dilakuk ukan an untu untu mence mencega gah h hidro hidrolsi lsisi si gliko glikosid sida. a. Untuk Untuk simplisia yang mengandung flavonoid dengan kepolaran yang lebih rendah lagi dapat langsung diisolasi dengan merendam heksana atau eter selama beberapa menit, perlu diingat bahwa ekstrak yang diperoleh juga mengandung lemak dan lilin. II.2 Isolasi
Metode terbaik untuk mengisolasi atau memisahkan campuran flavonoid antara lain dengan kromatografi kertas (KKt) dan kromatografi lapis tipis (KLT). Jika menggunakan metode KKt, kertas yang disarankan adalah kertas Whatman 3MM (46 x 57 cm) atau yang setara. Kertas dibuat seperti gambar di bawah. Ekstrak ditotolkan kira-kira 8 cm dari tepi lipatan pertama dan 3 cm dari lipatan kedua dengan garis tengah 3 cm yang berpusat pada satu titik. Pengeringan berca bercak k diban dibantu tu deng dengan an penge pengerin ring g rambu rambut. t. Ekst Ekstrak rak yang yang ditot ditotol olkan kan dapa dapatt digunakan secara umum yaitu dari sejumlah ekstrak yang diperoleh dari 50 –
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asetat 15%. Untuk antosianin disarankan pengembang setara , biasanya BAA atau Bu/HCl dan kedua HCl 1%. Flavono Flavonoid id tidak tidak nampak nampak pada pada kertas kertas kromato kromatogra gram, m, kecual kecualii antosia antosian n (berca (bercak k jingga sampai lembayung lembayung yang menjadi biru dengan uap ammonia), khalkon, auron dan 6-hidroksi flavanol kuning). Karena alasan tersebut, untuk mendeteksi bercak, bercak, kromatogram kromatogram diperiksa diperiksa dengan sinar UV (366 (366 nm dan 254 nm) dan dapat diperjelas dengan uap ammonia.
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8 cm
3 cm
arah aliran pengembang pertama
arah aliran pengembang pertama
(a)
(b)
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silika, silika, atau atau poliamid poliamida), a), dilanjut dilanjutkan kan dengan dengan elusi elusi beruntun beruntun setiap setiap kompone komponen n memakai pelarut yang sesuai. Kolom hanya berupa tabung kaca yang dilengkapi dengan keran pada salah satu ujungnya dengan ukuran garis tengah berbanding panjang kolom 1:10 atau 1:30. Mengemas kolom dilakukan dengan hati-hati agar dihasilkan kolom yang homogen. Jika kolom tidak memiliki kaca masir, maka dapat diganakan kaca wol atau kapas, sumbat ini direndam dengan pengelusi yang tingginya kira-kira 10 cm. Kemas Kemasan an kolo kolom m dibua dibuatt bubur bubur deng dengan an pela pelarut rut yang yang sama, sama, lalu lalu ditua dituang ng dengan dengan hati-ha hati-hati ti ke dalam dalam kolom kolom tanpa tanpa terputu terputus-pu s-putus tus agar agar tidak tidak terbent terbentuk uk lapisan. Kemasan dibiarkan turun dan kelebihan pelarut dibiarkan turun. Jika fase diam poliamida yang digunakan maka dianjurkan untuk mengembangkan dulu satu jam.
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Baik untu untuk k aglik aglikon on yang yang kura kurang ng pola polar, r, misaln misalnya ya isofla isoflavo von, n, 2. Silika. Baik flavanon, metil flavon dan falavonol. Sebaiknya dicuci lebih dahulu dengan asam klorida pekat untuk menghilangkan sesepora besi yang dapat membuat flavonoid terikat kuat pada kemasan. Kiselgel 60, 70 – 230 mesh (merck).
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yang larut (dapat mengotori). mengotori). Polyclar AT General General Aniline and Film Corporation), Corporation), Polyponco 66D Polymer Corporation) dan Polyamida (Woelm). Digunakan untuk memisahkan memisahkan campuran, campuran, 4. Gel sephadex (deret G). Digunakan terutama berdasarkan atas ukuran molekul (mengunakan pelarut air), molekul besa besarr
akan kan
tere terelu lusi si lebi lebih h
dahu dahulu lu..
Sang Sangat at berg bergun una a
untuk ntuk memi memisa sahk hkan an
poliglikosida yang berbeda bobot molekulnya. Bila pengelusinya adalah pelarut organik, gel sephadex deret G berprilaku seperti selulosa, tetapi kapasitasnya lebih besar. Gel harus dikembang terlebih dahulu selama 12 jam dengan eluen. Jenis niaga G-10 (untuk bobot molekul 0 – 700) dan G-25 (untuk bobot molekul 100 – 1500) 5. Gel sephadex (LH-20). Dirancang untuk menggunakan pelarut organik,
dan dapat digunakan dua cara. Bahan ini menghasilkan eluen tanpa sisa, sangat
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warna orange atau coklat. Warna merah dan lembayung yang terjadi mendadak dalam suasana asam disebabkan adanya khalkon atau auron. Flavono Flavonoid id menjadi menjadi kuning kuning terang terang atau atau jingga jingga dalam dalam larutan larutan basa dan dapat dideteksi jika bagian tumbuhan tanwarna diuapi amonia.Timbulnya warna ini karena adanya pembentukan garam dan terbentuknya struktur kuinoid pada cincin B seperti berikut : OH
-
O
O
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Kompleks flavonoid dengan asam borat dan natrium asetat
Selai Selain n pada pada kedu keduduk dukan an orto orto,, gugus gugus hidro hidroks ksii deng dengan an kedud keduduka ukan n lain lain diduga juga dapat membentuk ikatan dengan campuran asam sitrat dan asam borat, pada pemanasan dan dikenal dengan pereaksi sitroborat, Sampai saat ini mekanisme mekanisme reaksi reaksi yang yang terjadi terjadi antara antara flavonoi flavonoid d dengan dengan pereak pereaksi si sitrobo sitroborat rat belum dapat diketahui secara pasti. Warna fluoresensi yang terbentuk adalah
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Pembentukan kompleks antara flavonoid dengan aluminium klorida lewat dua macam gugus yang berbeda yaitu gugus hidroksil yang berkedudukan orto dan gugus hidroksil yang berkedudukan dekat dengan gugus karbonil, dapat digunakan sebagai dasar penetapan adanya gugus hidroksil pada kedudukan tertentu dalam molekul flavonoid. Lazimn imnya
ident dentif ifik ika asi
fla flavonoid noid
diaw iawali
dengan
reaksi ksi
warna
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coklat Leukoantosianin
Kuning
Merah / violet
Violet
Biru / violet
Kuning / jingga
Merah memucat
Isoflavon
Kuning
Kuning
Kuning
Merah violet
Isoflavanon
Kuning
Kuning
Tak berwarna
Merah
Antosianin Antosianin Antosianidin Antosianidin
II.4 Hidrolisis
/
Violet
lalu
Kuning / jingga
muda
/
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R
R +
C
+
H
O
OR'
R'
R
Alkohol
OH
OH
H
OH OH
H2O
OR'
Asetal
CH2OH O
O C
+
H
CH2OH OH
OR' C
+
H
Hemiasetal
CH2OH
Glukosa
R
C H
Aldehida
R'-OH
OH
O
R'OH
OH
OH
+
H
OH OH
Glukosa
OR'
OH OH
Glukosida
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Selain kecepatan hidrolisis dengan asam dari glikosida, juga dipengaruhi oleh posisi ikatan gula pada inti flavonoid. Gula yang berikatan pada posisi 3 dari flavonoid akan lebih mudah dihidrolisis dibanding pada posisi 7, sedang paling
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-
β-galaktosidase, menghidrolsisi β-D-galaktosida
-
β-glikuronidase, menghidrolsisi β-D-glukuronidase
- Pektinase, menghidrolsis α-D-poligalakturonida dan α-L-rhamnosida
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menunj menunjuk ukka kan n abso absorbs rbsii yang yang sesu sesuai ai untuk untuk cincin cincin B sinamo sinamoil, il, seda sedang ng pita pita II berhubungan absobsi cincin benzoil.
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serapan tergantung pada panjangnya sistem konyugasi serta adanya subtitusi terutama pada kedudukan atom C 3 dan C5. Sebagai contoh senyawa flavon yang mempu mempunya nyaii siste sistem m sinam sinamoil oil menga mengand ndung ung siste sistem m kony konyuga ugasi si lebih lebih panja panjang ng
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