Definisi Flavonoid
Merupakan senyawa fenol terbanyak
ditemukan di alam.
Merupakan zat warna merah, ungu, biru, dan
sebagian zat warna kuning.
Kerangka dasar terdiri atas 15 atom karbon
yang membentuk susunan C6-C3-C6. 3
3 A
2
B A 2 1
3
A 1 B
2 B
1
OH
O
OH O
leukoantosianidin calkon
dihidrocalkon
(flavan-3,4-diol)
O O O
O
OH OH
O O O
O
flavanon flavanonol flavon flavonol
+ +
O O O
C
H
OH
O
garam flavilium antosianidin auron
Isoflavonoid dan neoflavonoid hanya ditemukan
dalam beberapa jenis tumbuhan.
Ragam isoflavonoid:
isoflavon pterokarpan
HO O MeO O
R O O
OH
R = H daidzein O
R = OH genistein pterokarpin
rotenoid
kumestan
R
R2 O O O O
O
R3
R1 O R O
OH OMe
OMe
R1=R3=H R2=OH kumestrol R = H rotenon
R1=R3=OH R2=OMe medelolakton R = OH amorfigenin
Ragam neoflavonoid:
4-arilkumarin dalbergion
MeO O O
MeO O
HO
O
R1
R1
4-metoksidalbergion
R1=R2=H dalbergin
R1=OH R2=OMe melanein
Ciri struktur flavonoid
Gugus hidroksil hampir selalu ditemukan pada
posisi 5 dan & 7 dari cincin A.
OH OH
OH
HO O HO O
HO OH
OH
OH O OH O OH O
apigenin kaemferol
floretin
OH
OH
+
HO O HO
HO O O
OH C OH
H
OH
OH
OH O OH
OH
pelargonidin sulfuretin
epikatecin
Ciri struktur flavonoid
Cincin B flavonoid seringkali mempunyai gugus
gugus hidroksil atau alkoksil pada posisi 4’, atau
3’ & 4’.
Adanya tiga gugus hidroksil atau alkoksil, atau
tidak teroksigenasi sama sekali, atau
teroksigenasi pada posisi 2’, sangat jarang
ditemukan.
Hal tersebut disebabkan biogenesis dari
flavonoid.
Glikosida senyawa flavonoid berikatan dengan
gula pada gugus hidroksil yang ada.
Benefit bagi kesehatan tubuh
The Most Important Classes of Phenolic Compounds in Plants
Number of C-atoms Basic skeleton Class
6 C6 Simple
phenols,benzoquinones
7 C6- C1 Phenolic acids
8 C6- C2 Acetophenone,phenylacetic
acids
9 C6- C3 Hydroycinnamic
acid,polypropene,coumarin,
isocoumarin
10 C6- C4 Naphtoquinone
13 C6- C1 - C6 Xanthone
14 C6- C2- C6 Stilbene,anthrachinone
15 C6- C3- C6 xanthone
18 (C6- C3)2 Flavonoids,isoflavonoids
30 (C6- C3- C6)2 biflavonoids
n (C6- C3)n Lignins
(C6)n Catecholmelanine
(C6- C3- C6)n (Condensed tannins)
The Most Important Classes of Flavonoids and their Biological Significance
Class Number of known Biological significance
members
Biflavonoids 65 Gingko
Isoflavonoids 15 Estrogen effect, toxic for
fungi
The Ecological Meaning of Some Phenolic Compounds for Plants
Function Group Example(s) and plant species
where the effect was studied
Flower pigments Anthocyanes Cyanidins-3, 5-diglucoside in
Chalcones Rosa
Aurones Coreopsin in Coreopsis tinstoria
Yellow flavonoids Aureusin in Anthirrhinum majus
Flavones Gossypetine-7-glucoside in
Gossypium
Apegenin-7-glucoside in Bellis
Perennis
Fruit pigments Antocyanines Petunidin glucoside in Atropa
Isoflavones belladonna
Chalcones Osajin in Maclura pomifera
Ocanin in Kyllingi breviofolia
Allelopathic Quinones Juglon in Juglans regia
substances Phenols Hyroquinone in Arctostaphylos
Phenolcarboxylic Sialic acid in Quercus falcate
acids Ferulic acid in Adenostoma
Hydrocinnamic acids
The Ecological Meaning of Some Phenolic Compounds for Plants
Function Group Example(s) and plant species
where the effect was studied
Protection against Quinones Juglone in Carya ovata
pests Tannines Gallotannine in Quercus robur
Flavonols Quercitine-glycosids in
Gossypium
Fungicides Isoflavones Luteon in Lupinus
Phenolcarboxylic Protocatechunic acid in Allium
acids Phloridcine in Malus pumila
Dihydrochalcones
Phytoalexines Stilbens Reservatrol in Arachis hypogaea
Phenylanthrenes Orchinol in Orchis militaris
Isoflavanes Vestitol in Lotus corniculatus
Pterocarpens Pisatin in Pisum sativum
Phenylpropanoids Coniferyl alcohol in Linum
Fucocoumarins usitiltissimum
Psoralen in Petroselinum crispum
Cara isolasi dan identifikasi senyawa flavonoids
Pembuatan ekstrak
Dengan metode
Ekstraksi
berkesinambungan
Fraksinasi untuk
Isolasi senyawa
flavonoid
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