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ABSTRACT
Flavonoids are natural products widely distributed in plant kingdom and currently
consumed in large amounts in the daily diet. These are categorised according to
INTRODUCTION
Phytochemicals are defined as the substances found in
1.
Flavonoids
FLAVONOIDS
[1].
polyphenols[9]
[3, 4].Polyphenols
[2]
are characterised as :
play
vital
bioactive
role
in
flavan nucleus
with
[8]
chromane-type
skelton
having
[12, 13].
phenyl
[14].
feature
2-phenyl-benzo--pyrane
of
flavonoid
is
which
[7, 8]
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Vol 1 Issue 1
8
7
1'
4'
2'
[14].
5'
6'
Biosynthesis of Flavonoids:
sulphated.
O
S-CoA
H2C CH3
CH2
3CH3COOH
3'
2'
4'
O
O
HO
OH
OH
6'
5'
1'
FLAVAN NUCLEUS
According to
O
O
O
H
H
O
OH
(1) Flavone
(2) Flavonones
(3)Flavonol
(4) Isoflavone
Distribution of flavonoids:
Flavonoids are widely distributed among the plant
3
2
3'
O+
4'
OH
H
H
OH
2'
5'
6'
OH
4
B
The dietary
[8].The
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26
Flavonoid
subclass
Food source
Representative
flavonoids
1.
Flavonol
Kaempherol,
myricetin, quercetin,
rutin
2.
Flavones
Parsley, Thyme
3.
Flavonones
Citrus
4.
Catechins
Apple, tea
5.
Anthocyanidins
6.
Isoflavones
Cherries, Grapes
Soya beans,
Legumes
Apigenin, chrysin,
luteolin
Hesperitin, erodictyol,
naringen
Catechin,
galocatechin
---------------Daidzen, genistein,
glyciten, formanantine
Flavonoids
control,
morphogenesis,
sex-
[10].
Plant
Family
1.
Aloe vera
Asphodelaceae
2.
Flavonoid present
Reference
Luteolin
20
Kaempferol glycosides: mauritianin, clitorin, nicrotiflorin, biorobin in its leaves and flowers
21
3.
Azadirachta
indica
Meliaceae,
Zingiberaceae
4.
Andrographis
paniculata
Acanthaceae
5.
Bacopa
moneirra
Scrophulariaceae
21
6.
Betula pendula
Betulaceae
26
7.
Butea
monospermea
Bauhinia
monandra
Fabaceae
27
Fabaceae
Quercetin-3-O-rutinoside, Quercetin
28
9.
Brysonima
crassa
Malphigaceae
29
10.
Calendula
officinalis
Cannabis
sativa
Compositae
Quercetin, isorhamnetin
26
Cannabaceae
21
12.
Citrus medica
Rutaceae
13.
Clerodendrum
phlomidis
Clitoria
ternatea
Glyccheriza
glabra
Verbenaceae
30
Fabaceae
Kaempferol-3-O- -glucoside, Quercetin-3-O- -glucoside, myricetin-3-O- -glucoside, isorhamnetin-3-O- glucoside, 3,5,7,4-tetrahydroxy-flavone-3-rhamoglycoside, kaempferol-3-neohesperidoside
Leguminosae
16.
Mimosa pudica
Mimosoideae
18.
Limnophila
indica
Scrophulariaceae
19.
Mentha
longifolia
Momordica
charantia
Oroxylum
indicum
Passiflora
incarnate
Lamiaceae
8.
11.
14.
15.
20.
21.
22.
22,23
24, 25
25, 31
26
30
30
32, 33
Curcurbitaceae
34
Bignoniaceaea
30
Passifloraceae
26
23.
Pongamia
pinnata
Fabaceae
24.
Tephrosia
purpurea
Fabaceae
30
25.
Tilia cordata
Tiliaceae
26
27
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35, 36, 37
Vol 1 Issue 1
PHARMACOLOGY OF FLAVONOIDS:
Reported
Pharmacological
activities
of
e-
O2
.O
2
H+
HO2.
flavonoids:
HO2. O2
activities.
These
includes:
15],
11,
cytotoxic
neurodegenerative
[4,11,13,39].
antitumour,
diseases,
treatment
vasodilatory
[10,
of
action
lipid-peroxidation,
platelet
permeability
fragility,
and
aggregation,
anti-
capillary
cyclo-oxygenase
and
.O 2
lipase,
-glucosidase,
kinase [41].
1.
S.
No.
Flavonoids as antioxidants:
[42].
Reactive
species
Mechanism
1.
O2 (Superoxide
anion)
2.
HO2
3.
H2O2
(Hydrogen
peroxide)
4.
OH (Hydroxy
radical)
+ .O2-
radical
scavenging
capacity
is
primarily
.
F-O. + RH
2H+
H2O2 + O2
SOD
Fig (VI): Mechanism catalysed by SOD
H2O2.
5.
6.
(Alkoxy
RO
.
radical), ROO
(Peroxyl
radical)
1
O2
formation
and
decomposition
reactions,
the
to aroxyl
Jan-Mar 2011
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28
groups (Fig.VII(c)).
(a)
OH
(b)
OH
OH
OH
b
OH
OH
OH
[8]
and
HO
HO
OH
OH
OH
HO
OH
(c)
inhibit
possess
strong
antioxidant
protein
FLAVONOID
of
[47].
regulation
(-) cAMP
(-) protein kinase C
(-) protein
phosphorylation
(-) COX
activity [48].
Gulati et al., reported that quercetin at a dose of 15
mg/ 100g p.o. produced significant hepatoprotection
[49].
29
Jan-Mar 2011
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[16].
receptor
administered
enzymes
intraperitoneally
(25-100
mg/kg)
(FcR).
i.e.
Fc
receptor
is
non-covalently
phosphatidylinositol
lipase
which
from
the
plasma
membrane.
Several
inositol
cell, with the result that the latter emits IL-1. This
cellular
hormones,
contraction [16].
immunity,
cytokines,
tissue
The toxin-antibody
[50].
LIPOOXYGENASE
COX-2
5-LOX
5-HPETE
PGG2
PGD2
PGE2
12-HETE
LTA4
PGH2
PGI2
12-LOX
PGF2
TXA2
LTE4
LTB4
[42, 45].
Flavonoids prevent
cytokines
which
are
controlled
by
flavonoids.
[40].
Flavonoids also
[40, 53]
and also
site.
inflammation.
Flavonoids
[16].Various
also
promote
IFN
synthesis
Jan-Mar 2011
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30
FLAVONOID
(-) COX
(-) iNOS
(-) cytosolic kinase
(-) tyrosine kinase
(-) neutrophil
degranulation
(-) protein kinase C
(+) Promote IFN
synthesis
Flavonoids
in
treatment
of
Rheumatic
may
be
to
activate
cytotoxic
T-
inflammatory
Apigenin,
and
analgesic
effects.
[16]
as
FLAVONOIDS
Inhibit PGs
Kang
et
al.,
reported
that
apigenin
inhibits
joints.
[40].
Flavonoids
in
treatment
of
thrombosis:
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Cancer
antiaggregatory
of
effect
is
antiaggregatory properties
by
the
43].
[40,
inhibition
cells
manifest
to
varying
degree
of
FLAVONOIDS
with
the
initiation,
development
and
Flavonoids
Normal cell
emerged
as
potential
[52].
Initiated cell
have
Preneoplasts
Metastasis
Tumour
Prevent further DNA damage, Inhibit angiogenesis, Inhibit invasion
Fig XIII: Multistage of carcinogenesis and potential effects of polyphenols on cancer progression [55]
Flavonoids have been shown to be highly effective
scavengers of most types of oxidizing molecules,
OH
OH
OH
OH
HO
HO
O
HO
O
OH
OH
OH
OH
OH
O
OH
beneficial
effect
through
their
impact
on
the
bioactivation of carcinogens.
OH
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Vol 1 Issue 1
[16].
[55].
activity
proliferation
of
several
detoxifying
and
antioxidant
enhance
quinone reductase
[16,
55].
In estrogen-dependent
existing
neuronal
function,
stimulate
to
flavones
exert
neuroprotective
reported
[14].
to
actions
act
as
even
novel
at
low
brain-stem
stimulants
56].
OH
OH
HO
OH
HO
OH
O
OH
influence
mechanism.
memory
and
cognition
via
similar
components
such
as
quercetin
had
FLAVONOIDS
Angiogenesis
Neurogenesis
Old neurons
Neuronal Maturation
Synaptic Activit
Functional integration
Synaptic plasticity
Immature neurons
New Synapses
Memory
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Vol 1 Issue 1
mg/kg
p.o.
impairs
cognitive
function
(-) cAMP
(-)PDEase
(-) Ca++ dependent ATPase
FLAVONOID
by
PREVENT
ALLERGY
[59]
and
dependent
ATPase
which
are
responsible
for
STRESS
CRF
release
GLUTAMATE
Hypothalamus
NMDA
receptor
ACTH
hormone
NA
5- HT
BDNF
2 receptor
5HT1A
TrkB
receptors
Pituitary
Detrimental gene
Cortisol
release
Beneficial gene
transcription response
+
transcription response
_
Neural apoptosis
+
Neurogenesis
DEPRESSIVE SYMPTOMS
Fig XXII: Pathophysiology of depression [51]
Jan-Mar 2011
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34
Cladosporium
sphaerospermum,
Pencillium
5,7,4-trihydroxy-8-methyl-6-(3-methyl-[2-butenyl])-
2S-flavonone
[7].
These were
texana
isolated
and
from
shrub
flavonoids
Eysenhardtia
7-hydroxy-3,4-
anticonvulsant.
the
Considering
the
sedative,
results:
2S-hesperidin>linarin>rutin>diosmin\cong2S-
neohesperidin> gossypin2S-naringin.
tracheiphila
hesperidin
morin-3-O-arabinoside,
quercetin-3-O-arabinoside
while
[43].
leaves
and
reported
from
that
quercetin,
Psidium
these
four
guajava
possess
bacteria
stearothermophilus,
including
Bacillus
Brochothrix
thermosphacta,
Listeria
monocytogenes,
Escherichia
coli,
Pseudomonas
fluorescens,
Salmonella
enteric,
[63].
showed
inhibitory
activity
on
microorganisms.
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Vol 1 Issue 1
Activity
Organism
Flavonoid
Staphylococcus aureus
1.
Antibacterial activity
2.
Antiviral activity
3.
Antifungal activity
Staphylococcus albus
Streptococcus pyogenes
Streptococcus viridians
Streptococcus jaccalis
Streptococcus baris
Streptococcus pneumonia
Pseudomonas aeruginosa
Escherichia coli
Baccilus subtilis
Bacillus anthracis
Proteus vulgaris
Clostrium perfingens
Rabies virus
Herpes virus
Para influenza virus
Herpes simplex virus
Respiratory synctial virus
Immuno-deficiency virus infection
Auzesky virus
Polio virus
Mengo virus
Pseudorabies virus
Candida albicans
Candida tropicalis
Fusarium solani
Botrytis cinerea
Verticillum dahlia
Azotabacter vinelandii
Alternacia tennisima
Cladosporium herbarum
diseases:
[16].
species.
Etiology
of
Cardiovascular
adherence [16].
Endothelial
dysfunction
with
increased
platelet
cellular
free
redox
active
iron,
and
the
Jan-Mar 2011
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36
Cardiovascular diseases
Influence of flavonoids
1.
Atherosclerosis
Decrease in LDL oxidation by LOX inhibition and attenuation of oxidative stress, inhibition of
leucocyte leucocyte adhesion, myeloperoxidase, decreased expression of iNOS and COX-2
2.
3.
Heart Failure
4.
Arrhythmia
5.
Hypertension
Quercetin
protects
LDL
against
oxidative
cardioprotective
[43].
mg/kg [68].
hepatotoxicity:
Role
[65].
[11].
Silymarin,
flavonoids
apigenin,
in
treatment
quercetin,
naringenin
of
are
[66].
of diabetes mellitus
[16].
of
FLAVONOID
hirustrin,
hepatoprotective action
37
avicularin,
quercetin
possess
Jan-Mar 2011
Vol 1 Issue 1
[70].
[10].
Flavonoids
hepatoprotective
activity
against
tacrine-induced
beverages
and
have
been
previously
used
in
[10, 15].
CONCLUSION
enzymes
to
toxicity
appears
is
to
required
vary
to
from
be
compound
done
on
these
Disease
1.
Ulcer
2.
Rheumatoid arithritis
3.
Inflammation
4.
Cancer
5.
Memory dysfunction
6.
Depression
7.
Cardiovascular
diseases
8.
Diabetes mellitus
9.
Antiallergic
10.
Hepatoprotective
11.
Thrombosis
Flavonoid
Kaempferol,
(+)-Cyandidanol-3, meciadanol, catechins
Sofalcone, Quercetin
Apigenin, rutin
Quercetin, apigenin, catechin
Hesperidin,rutin, luteolin
Kaempferol, quercetin, myricetin, fisetin
Quercetin, Kaempferol, Galangin, Apigenin
Quercetin, naringin
Genistein, Quercetin
Apigenin, luteolin, quercetin
Catechins
Genistein
Quercetin
Fisetin
Naringenin,
2S-hesperidin, Linarin
Quercetin
7-monohydroxyethylrutoside,
7,3,4-trihydroxyrutoside
Fisetin
Quercetin
Quercetin
Rutin, citrin
Disodium cromoglycate
Quercetin
Avicularin, hirustrin
Onitin, luteolin
Tangeratin, hesperidin, quercetin, rutin
Trihydroxyethylrutoside, O-( hydroxyethyl)rutoside, (+)-catechol
Nobelitin, sinesetin
Jan-Mar 2011
Target
PAF
Gastric H+/K+ ATPase
PG synthesis
Suppress inflammation by acting on COX
COX and iNOS
PG synthesis
+
Vol 1 Issue 1
Reference
41, 43
41
41, 43
54, 53
50, 52
43, 54
43
16
16
16,55, 51
46, 52
16, 55
49
49
58
61
7
43
68,
41
58, 59
41
41
69, 71
71
71
41
38
REFERENCES
1.
12.
Dietary
Giammanco,
structure,
M.
Citrus
biological
flavonoids:
activity
and
Molecular
nutritional
13.
3.
D,
Ferreira,
D,
Marais,
JPJ.
Circular
14.
Journal
following
oxidation.
Biochimica
et
16.
Flavonoids
and
isoflavonones
17.
Sahu,
SC,
Gray,
GC.
Pro-oxidant
activity
of
and
36: 838-849.
Absorption,
Metabolism
18.
antioxidant
activities.
Food
Chemistry
19.
3135-3170.
Traditional
flavonoid
nervous
system
glycosides.
depressant
European
action
Journal
of
21.
Complementary
and
Alternative
of
22.
488.
23.
Of Antimicrobial
24.
Babu,
VS,
Narasimhan,
communication
S,
Nair,
Enhanced
GM.
Short
accumulation
of
39
of
Central
11.
flavonoids.
2005;89: 191-198.
10.
for
their
9.
methods
Skerget,
8.
(Phytoestrogens):
7.
membrane
review:
6.
Structure-dependent
activity.
reactions
5.
H.
biochemical
4.
Tsuchiya,
and
466-479.
Slade,
occurrence
Jan-Mar 2011
Vol 1 Issue 1
of
Flavonoids
of
Andrographis
paniculata.
mangrove
plant,
Pongamia
pinnata.
edition. Elseveir.
39.
37.
Phytopharmacology ; 1: 124-132.
41.
42.
Upadhay, A. In-vitro
Dhamotharan,
R,
Dananjeyan,
B,
Bama,
SS.
32.
33.
43.
2010; 4: 1089-1101.
44. Ghasemzadeh,
A,
Jaafar,
HZE,
Rahmat,
A.
164: 886-894.
4324-4333.
45.
flavonoids
extracted
Ghoulami,
S,
Phytochemical
from
Mentha
longifolia.
589.
46. Sharififar, F, Dehghn-Nudeh, G, Mirtajaldini, M.
Idrissi,
study
of
AI,
Fkih-Tetouani,
Mentha
longifolia
S.
of
36.
of
2009; 4: 93-99.
35.
antioxidative activity
136-140.
888.
47.
277-279.
79: 379-381.
Jan-Mar 2011
Vol 1 Issue 1
40
61.
Involvement
Jung, WY, Park, SJ, Park, DH, Kim, JM, Kim, DH,
phosphorylated
binding
cyclic
protein
AMP
response
element-
expression.Toxicological
62.
letters
50. Miller,
AL.
flavonoids:
Structure,
63.
from
Marchand,
LL.
flavonoids-
Cancer
preventive
review.
effects
Rattanachaikunsopon,
P,
Phumkhachorn,
P.
Biomedicine
of
&
Arithrits
Guardia,
T,
Rotelli,
AE,
Osvaldo,
A.
Anti-
567.
to
cancer
67.
chemoprevention.
442.
Traditional,
Complementary
and
Alternative
196-208.
ameliorates
and
cognition:
The
molecular
mechanisms
hyperglycaemia
in
streptozotocin-
RK,
Agarwal,
S,
Agarwal,
SS.
70.
103: 16568-16573.
stress
60. http://www.umm.edu/altmed/articles/quercetin000322.htm
induced
by
tert-Butyl
hyperoxide.
337-353.
41
two
59.
isolated
of
steroids
activity
and
Antimicrobial
pathways
56.
DCRD.
55.
in
54.
system
monoaminergic
52.
Oleveira,
flavonoids
Antioxidant
of
51.
Jan-Mar 2011
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