FLAVONOID

Uswatun Khasanah,M.Farm.,Apt.
Farmasi Bahan Alam
Program Studi Farmasi FKUB

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Contents

Definisi, struktur dan penamaan

Biosintesis

Klasifikasi , contoh, dan bioaktivitas

Identifikasi
 Definisi , struktur, dan penamaan

Flavonoids are polyphenolic A

compounds comprising fifteen
carbons, with two aromatic rings Add Your
connected by a three-carbon
bridge
Text here
B
widely distributed in plant
flora.

C
4,000 flavonoids are known

D
some of them are pigments in
higher plants
Jalur biosintesis
Fungsi flavonoid pada tanaman

Flavonoid

Function : attracting
They are polinating insect,
present in high processes as UV
concentrations in protection,
pigmentation,
the epidermis of
stimulation of
leaves and the nitrogen-fixing
skin of fruits nodules and
disease resistance
UV protection and Attracting
polinating insect

Bunga seruni
Flavonoid as UV protection
Stimulating of nitrogen fixing
nodule
Flavonoid nitrogen nodule
inducers
Antioxidant
 Klasifikasi flavonoid

Hydroxyl group C-4;

C-5; C-7
Mostly glicosydes
Hydroxyl group and
glicosides hydrophilic
Methyl or prenyl
lipophilic
Minor flavonoid
Flavonol

1 2 3
most commonly
dispersed myricetin, found
throughout quercetin, as O-glycosides.
the plant kingdom, isorhamnetin and Conjugation occurs
except : fungi and most frequently at the
kaempferol
algae. 3 position of the C-
found in commonly ring
consumed fruits, substitutions can
vegetables also occur at the 5, 7,
4, 3 and 5.
 Kaempferol and quercetin

Pharmacological activity ?
 Silybin

Silymarin is flavonol-lignan mixture (silybin,

isosilybin, silychristin, silydianin)
Plant :seed of Silybum marianum
Pharmacological activity : hepatoprotective
Flavon

Not distributed
Close Subsitution : Apigenin,
widely
structural hydroxylation, luteolin.
Significant
relationship methylation, Polymethoxyl
O- and C- accurences
to flavonol ated flavon :
alkylation Apium
lack OH at nobiletin and
Most accurs graveolens,
C3 tangeretin
as 7-O- parsley
glycosides (Petroselinum
cripsum),some
citrus species
Apigenin
 Artocarpin A

PRENILATED FLAVON
Isolated from bark of Artocarpus chempeden
Flavanon

1 2 3
Present high conc in
the absence of a highly reactive Rutaceae (citrus)
2,3 double bond hydroxylation, Ex: hesperidin or
Presence glycosylation herperitin-7-O-
of a chiral centre at rutinoside (in citrus
and O-methylation
C2 peel) tasteless
C-ring is attached reactions
Neohesperidin and
to the B-ring at C2 in naringin bitter
the -configuration taste of cutrus peel.
Anthocyanidin

1 2
Widely distributed Involve in
in plant kingdom protection of
In fruit, flower, plants against UV-
leaves, stem, seed,
B
root tissue
And attracting
polinating insect
3
In plants found as
sugar conjugates
anthocyanin
Ex : pelargonidin,
cyanidin, delphinidin,
malvidin, petunidin
Isoflavon

B-ring Ex : Have In human :

attached at genistein, estrogenic dietary high
C3 daidzein from activity genistein and
Found Glycine max; PHYTO- daidzein
exclusively in coumestan ESTROGEN reduce
leguminous and In grazing incidence of
plants coumestrol animal : block ca prostate
Ex : Glycine from clovers ovulation and breast ca
max
Flavan-3-ol

the most Two chiral Ex: (+)-cathecin Plant :

complex centre C2 and and (-)-cathecin; Camellia
subclass of C3 4 (-)-epicathecin sinensis,
flavonoid isomers and (+)- chocholate;
Have epicathecin; (+)- seeds of black
saturated C3 gallocathecin grapes
element in C- and (-)-
ring Non- epigallocathecin
planar
Chalcone and dihidrochalcone

Minor Dihydrochalc Biological Plant :

flavonoid one activity : moraceae
a matter of Prenylated antioxidant, family
debate chalcone scavenging
Best known Glycosilated agent,
as yellow to chalcone antimalarial
orange
colored
pigment
FLAVONOID SCREENING
FLAVONOID SCREENING

TLC screening of flavonoid

Stationary phase : silica
Mobile phase : CHCl- aseton-
formic acid : 6,5:3:0,5
Reagent : HSO 10%
FLAVONOID SCREENING
Solvent for TLC of flavonoid on
silica

Mobile phase for flavonoid mostly are combine with HOAc

or HCOOH
 TLC profile of flavonoid

Mobile phase : ethyl acetate-methanol = 95:5

Mobile phase : chloroform-methanol = 8,5:1,5

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Mobile phase : chloroform-acetone = 5:5 Mobile phase : chloroform-acetone-
formic acid = 6:3,5:0,5
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 Flavonoid screening using
spectrophotometer UV
42 nmSubstitusi
15 nmOrto- 5-OH
11nmNonsubstitu dihidroksi pada
si 7-OH group (ring ring B 56 nmSubstitusi
A)
OH pada C-3 dan
C-4, gugus keton
pada C4

Pada spektra UV ,flavonoid memiliki 2-3 puncak panjang gelombang

maksimum
 Proton NMR flavonoid

Proton
Proton
pada
pada
ring C
ring A
 Proton NMR flavonoid

Proton
Proton ring A
ring C

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 Carbon NMR OF FLAVONOID

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 TUGAS

Cari jurnal tentang isolasi yang dipandu oleh

bioaktivitas untuk target senyawa flavonoid
dan fenol/aromatik.

Keyword:
isolation guided bioassay of..flavonoid..phenolic
compound...
Isolation of flavonoid/phenol using TLC
preparative
Isolation of flavonoid/phenol using HPLC
preparative
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