Farmakognosi

flavonoid
Dosen : Yasmiwar Susilawati
FLAVONOID
Pendahuluan :

Flavonoid merupakan golongan fenol alam yang
terbesar, hampir semua tumbuhan hijau
mengandung flavonoid.


Menurut perkiraan 2% dari seluruh karbon yang
difotosintesis oleh tumbuhan atau + 1x 10 9
ton/tahun karbon diubah menjadi flavonoid
atau senyawa yang berkaitan erat dengannya
(Smith, 1972).
Flavonoid pada tumbuhan
Merupakan kandungan khas tumbuhan
hijau dan terdapat pada hampir semua
bagian tumbuhan (daun, akar, kayu,
kulit kayu, nektar, tepung sari, bunga,
buah, dan biji).
Merupakan pigmen tumbuhan yang
paling umum, walaupun ada beberapa
flavonoid yang tidak berwarna.
Flavonoid pada hewan ???
Flavonoid pada hewan jarang. Yang
pernah dilaporkan terdapat pada :
kelenjar bau berang-berang
propolis (sekresi lebah)
dalam sayap kupu-kupu
Tetapi ini pun diperkirakan bukan hasil
biosintesis hewan
Penyebaran flavonoid
pada tumbuhan yang terbesar terdapat
pada Angiospermae
terdapat kecendrungan : tumbuhan yang
secara taksonomi berkaitan akan
menghasilkan flavonoid yang jenisnya
serupa Dasar Chemotaxonomi
Divisi Nama Umum Flavonoid yang ditemukan
Prokariot :
Sizofita
Sianofita

Bakteri
Alga hijau - biru

-
-
Eukariot :
Klorofita
Feofita
Rodofita
Fungus
Briofita
Trakeofita

Angiospermae

Alga hijau
Alga coklat
Alga merah
Fungus
Lumut kerak
Lumut hati
Psilofita
Lycopodium
Gimnospermae

-
-
-
Dihidrokalkon
-
glikosida flavon, glik. flavonol (jarang)
biflavon, O dan C -glikosida flavon
biflavon, O dan C -glikosida flavon
Flavon, biflavonoid, flavanon,glikosida flavon,
isoflavon,proantosianidin, antosianin,flavonol, dihidroflavonol

Terdapat semua jenis flavonoid
Peran Flavonoid dalam tumbuhan :

Pengaturan tumbuh
Pengaturan fotosintesis
Kerja antimikroba dan antivirus
Kerja terhadap serangga
Fitoaleksin
Penggunaan Flavonoid

Antioksidan
(cth : silimarin dari Silibum
marianum sebagai
protektor hati dengan
menghambat sintesis
prostaglandin)
Menghambat reaksi oksidatif
seperti fosfodiesterase,
aldoreduktase,
monoamina oksidase,
reverse transkriptase,
DNA polimerase
- Menghambat lipooksigenase
- Menurunkan agregrasi
platelet (mengurangi
pembekuan darah)





- Menghambat pendarahan
- Melindungi asam askorbat
dari oksidasi (pengobatan
skorbut) : turunan katekin
pada buah jeruk
- Antihipertensi (menghambat
enzim pengubah angiotensin)
- Merangsang pembentukkan
estrogen pada mamalia
(isoflavon)


Struktur Umum Flavonoid :

15 atom C yang tersusun dalam konfigurasi
C6C3 C6

O
O
A
C
B
Struktur phenilbenzopiren
Flavonoid O-glikosida
Flavonoid dalam tumbuhan umumnya terdapat
dalam bentuk O-glikosida (jarang yang C-
glikosida) :
O-glikosida : satu gugus hidroksil flavonoid
(atau lebih) terikat pada satu gula (atau lebih)
dengan ikatan hemiasetal.
Gula yang umum : glukosa
Gula lain : galaktosa, ramnosa, xilosa, arabinosa
Gula yang jarang : alosa, manosa, fruktosa,
apiosa, asam glukoronat, galakturonat.
Contoh Flavonoid O-glikosida :
Apigenin 7-O--D-glukopiranosida (R = H)
Flavonoid C-glikosida

Gula terikat pada atom karbon Flavonoid (terikat
langsung pada inti benzen dengan satu ikatan
C-C)
Contoh flavonoid c-glikosida
Apigenin 8-C--D-glukopiranosida (Viteksin


)

Jenis Jenis Aglikon flavonoid :



Flavon
Flavonol
Antosianidin
Isoflavon
Flavanon
Kalkon
Auron
Biflavonoid
BIOSINTESIS flavonoid
Prazat dari alur sikimat dan alur asetat-
malonat membentuk flavonoid Khalkon
yang dianggap sebagai flavonoid
pertama yang terbentuk, semua jenis
flavonoid lain diturunkan darinya
melalui berbagai alur
Important flavonoids
1. Quercetin
Quercetin is a flavonoid that forms the "backbone" for many other
flavonoids, including the citrus flavonoids rutin, hesperidin, naringin
and tangeritin. In studies, quercetin is found to be the most active of
the flavonoids, and many medicinal plants owe much of their activity
to their high quercetin content. Quercetin has demonstrated
significant anti-inflammatory activity because of direct inhibition of
several initial processes of inflammation. For example, it inhibits both
the manufacture and release of histamine and other
allergic/inflammatory mediators. In addition, it exerts potent
antioxidant activity and vitamin C-sparing action.



2. Oligomeric proanthocyanidins
(OPC)





Proanthocyanidins extracts demonstrate
a wide range of pharmacological
activity. Their effects include
increasing intracellular vitamin C
levels, decreasing capillary
permeability and fragility, scavenging
oxidants and free radicals, and
inhibiting destruction of collagen, the
most abundant protein in the body.
3. Epicatechin

Epicatechin improves blood flow and thus
seems good for cardiac health. Cocoa, the
major ingredient of dark chocolate, is loaded
with epicatechin and has been found to have
nearly twice the antioxidant content of red
wine and up to three times that of green tea.
Important dietary sources

Good sources of flavonoids include all
citrus fruits, berries, onions, parsley,
legumes, green tea, red wine,
seabuckthorn, and dark chocolate (that
with a cocoa content of seventy
percent or greater).

Citrus

The citrus bioflavonoids include hesperidin, quercetin, rutin (a sugar of quercetin),
and tangeritin. In addition to possessing antioxidant activity and an ability to
increase intracellular levels of vitamin C, rutin and hesperidin exert beneficial
effects on capillary permeability and blood flow. They also exhibit some of the
anti-allergy and anti-inflammatory benefits of quercetin. Quercetin can also
inhibit reverse transcriptase, part of the replication process of retroviruses
(Spedding et al. 1989). The therapeutical relevance of this inhibition has not
been established. Hydroxyethylrutosides (HER) have been used in the
treatment of capillary permeability, easy bruising, hemorrhoids, and varicose
veins.

Green Tea

Green tea polyphenols are potent antioxidant compounds that
have demonstrated greater antioxidant protection than
vitamins C and E. Green tea may also increase the activity of
antioxidant enzymes. Green tea polyphenols may inhibit
cancer by blocking the formation of cancer-causing
compounds and suppressing the activation of carcinogens.
The major polyphenols in green tea are flavonoids (catechin,
epicatechin, epicatechin gallate, epigallocatechin
gallate(EGCG), and proanthocyanidins).
Though both green tea and black tea are derived from the same
plant (Camellia sinensis), they possess different antioxidants.
In producing black tea the leaves are allowed to oxidize,
during which enzymes present in the tea convert many
polyphenols to larger molecules with different biological
effects. However, green tea is produced by lightly steaming
the fresh-cut leaf, which inactivates these enzymes, and
oxidation does not occur


Subgroups :
Over 5000 naturally occurring flavonoids have been characterized
from various plants. They have been classified according to their
chemical structure, and are usually subdivided into 6 subgroups :




Flavonols: Quercetin, Kaempferol, Myricetin, Isorhamnetin
Flavones: Luteolin, Apigenin
Flavanones: Hesperetin, Naringenin, Eriodictyol
Flavan-3-ols: (+)-Catechin, (+)-Gallocatechin, (-)-Epicatechin, (-)-
*Epigallocatechin, (-)-Epicatechin 3-gallate, (-)-
Epigallocatechin 3-gallate, Theaflavin, Theaflavin 3-gallate,
Theaflavin 3'-gallate, Theaflavin 3,3' digallate, Thearubigins
Isoflavones: Genistein, Daidzein, Glycitein
Anthocyanidins: Cyanidin, Delphinidin, Malvidin, Pelargonidin,
Peonidin, Petunidin