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Biosintesis Flavonoid 25 April 2016
Biosintesis Flavonoid 25 April 2016
FLAVONOID
OCCURRENCE
• flavonoids are widely distributed in the flora
• they can be found in petals, crops, seeds, leaves, stems,
roots and barks
• it is the reddish – braunish - yellowish colour of
heartwood
• flavonoids of ferns are C-methyl derivatives
• glycoflavonoids can be isolated from see-weeds
• inferior plants and mushrooms have them only very
rarely
• microorganisms and algae species do not synthetize
STRUCTURE OF FLAVONOIDS
Polyphenols, namely favonoids are low molecular weight substances
The skeleton can be represented as the C6 - C3 - C6 system
Three main groups can be distinguished on the places of phenyl ring.
Along this pathway, many products can be formed, including the flavonols, flavan-
3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.
ENZIMATIC CONVERSION OF NARINGENIN
TO APIGENIN
http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/phenol/flavonoid.html
FLAVONOIDS ARE DIVIDED INTO GROUPS
According to the IUPAC nomenclature, they can be classified into:
flavone: 2-phenylchromen-4-one
flavonol: (3-hydroxyflavone) 3-hydroxy-2-phenylchromen-4-one
flavanone: 2,3-dihydro-2-phenylchromen-4-one
flavanonol: (3-hydroxyflavanone) 3-hydroxy-2,3-dihydro-2-phenylchromen-4-one
isoflavone
anthocyanidin
proantocianidin
other flavonoids catechin
chalcone
dihydrochalcone
aurone
Both the oxidation state of the heterocyclic ring and the position of ring B are
important in the classification.
ANTHOXANTHINES ARE THE REAL
FLAVONOIDS
Natural derivatives from benzo-γ-pyron stucture are
considered as flavonoids by certain researchers.
These molecules are anthoxantines.
benzo-γ-pyron γ-pyron
chromon
BIOCHEMICAL PATHWAY
SPECIAL FLAVON OF THE FORMATION OF
DERIVATIVES ROTENONE
• cumaroflavones
• isocumaroflavon
• furanoflavonoids
• biflavones
• coumestan derivatives
• rotenoids
• OH – groups
• number and position of
O-methyl, O-alkil, O-glycosyl-groups
• variance of glycosyl groups, acylation grade
• with or without conjugated double bonds
The most often occuring substituents can bond to C3 -, C5 –, C7 -, C3’ -, C4’ atoms.
Sugars can bond:
• through oxygen atom (O-glycosides)
• directly to C-atom (C-glycosides)
Antocyanides are always in their glycoside forms in vacuoles (in cell fluids)
catechines and procyanidines can be stored in their aglycone forms
(tannic acid holders, dissolved in essential volatile oils)
THE ROLE OF FLAVONOIDS IN PLANTS
Flavonoids are the secondary metabolites of plants, and they are providing
the colour and flavour materials.
• protect against
• UV-radiation
• fungus- , insect- and snail pests
• they are signal for N-bound bacteria
• they modify enzyme reactions
75% of Angiospermae contain kaempferol and quercetin and 10% of them
myricetin.
High concentration of
isoflavone quercetin in in vitro
3-phenyl-benzo-γ-pyron experiments causes
DNA mutations in spite
of that epidemiological
studies declare that
this flavonoid
consuming prevents
atherosclerosis, infarct
and others [Dunnick
catechin anthocyanidin 1998, Williams 2004].
Recent in vitro
examinations strenghten the
antiproliferative effects of
prenylated naringenin
(Humulus lupulus L., hops)
on prostate tumour cell line
culture.
(Phytomedicine. 13 (9-10), 732-4.
2006.)
• Oxygen of pyrane ring is quaterner.
• Oxoniumbases with acids form salines.
20 dkg soylent contains ca. 300
mg izoflavones.
CONDITIONS OF ANTIOXIDANT
PROPERTY
CATERGEN
(mg/ttg) (ug/ml)
• in PG-biosynthesis
• in leukotriene biosynthesis
• in NF-B translocation to the
nucleus
• in PKC activity and
• in PI3-kinase activity in signal
Kempferol inhibits
COX2-enzyme
BIOSYNTHESIS OF LEUKOTRIENES
The polyphenol like compounds inhibit signal transduction pathways, the TNFα–mediated
activation of NF-κB pathway, partly through the inhibition of IκB kinase and IL-1 β
activated NF-κB pathway, which is a partly distinct route. NF-κB activation by IL-1
requires an IL-1 receptor-associated protein kinase activity [Croson 1995].
LOCATION OF FLAVONOIDS IN THE ACTIVE
CENTRE OF PI3-KINASE
In the formation of
extracellular the matrix,
collagenes take part in the
delimitation of individual
cell populations.
Zn-containned matrix
metalloproteinases do the
continous renewal of the
extracellular matrix.