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Flavonoid Biosynthesis
Nila HudaChemistry ITS Surabaya
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Page 2Nila Huda Kimia ITS
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Page 3Nila Huda Kimia ITS
Flavonoid
Biosynthesis
Shikimic Pathway Malonic Pathway
Phenylpropanoid Pathway
p-Kumaril KoA
Malonil KoA
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Page 4Nila Huda Kimia ITS
Shikimic Pathway
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Shikimic Acid Formation
OHP
O
O
OH
OOHH
O
H
O
H
OH
HO OH
H
POH
O
OH
O
OOH
OHOH
HO OH
H
P
OH O
OH
HO
OOH
OH
HOH
H
OH
H
O OH
OH
OH
O
OH
H
O OH
H2
O
OH
O
OH
O OH
OH
OHO
OH OH
OH
OHO+
H+
(1)
(2)
H3PO
4
B:
H+
H3PO
4
H+
NADPHNADP+
(3)
H2O
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Chorismic Acid Formation
OH OH
OH
OHO
OH P ADP
OH
O
O OH
OH
OHO
P
OH
OH
O
O
O
OH
O O
OH
OHO
P
OH
OH
O
OH
OHO
H
O O
OH
OHO
P
OH
OH
O
OH2
OHO
O O
OH
OHO
P
OH
OH
O OH
OH
O
OH
OHO
OH
O
(3)
ADP
ATP Asam Piruvat
H+
+
:
H2O
:BH
3PO
4
(4)
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Prefenic Acid Formation
Claisen EtherRearrangement
OH
H
OH
O
OHO
O
OH
H
OH
O
OHO
O
O
OH
OHO
OH
O
O
OH
O OH
O
OH
H -
(4)
(4)
(5)
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Phenylpiruvate Formation
O
O
O OHO
OH
H
O
OH
O
O
OO
OH
O
OH
HH
O
O
O OH
O
OH
H
O
OH
O
OH
-
(6)
H2O
CO2
(5)
:B
-
CO2
NAD+
H+
NADH
(7)Nila Huda
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Page 9
Phenylalanine Formation
NH2
OH
O
R
O
OH
O
R
HNH2
COO
R' HCOO
R'
H
OH
O
ROH
HNH2
COO
R'
NH2
OH
O
ROH
OH
O
RNH
2
R = H (6)R = OH (7)
+
-
-
H
+
-
H+
+
NADH
NAD+
H2O
R = H (8)R = OH (9)
H+
L-Glutamat 2-oksoglutarat
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Phenylpropanoid
Pathway
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Phenylpropanoid pathway
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Kimia ITS
NH2
OH
OH
OH
O
OH
O
OH
SCoA
O
OH
NH3
H-SCoA
H2OOH
-
(8) (10)
(11)
(12)
Enzim yang terlibat:
I. Phenylalanine Ammonia Lyase (PAL)II. Cinnamate-4-Hidroxylase
(C4H)III. 4-Cumaroyl CoA Ligase (4CL)
I
II
III
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Malonic pathway
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Malonyl CoA Formation
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Kimia ITS
Enzim yang terlibat: Acetyl-CoA carboxylase
OH
O
H SCoA
SCoA
O
H
SCoA
O
SCoA
O
O
OB H
SCoA
O
OH
O
H2O
:B
:
-
H2CO3
(13)
H2O
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Chalcon Formation
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Page 15Nila Huda Kimia ITS Enzim yang terlibat: Chalcon Synthase
(CHS)
O
OH
CoAS
OH SCoA
O O
SCoAO
O O
OH
O
CoAS
O O
OH
SCoAO
O O
OH
OH SCoA
O O
OH SCoA
O O
O
O O
OH
OOH
OH O
OH
OH
-HSCoA-CO2
-HSCoA-CO2
-HSCoA-CO2
Basa
**Basa : berfungsi untuk mengambil H asam (H di posisi C-) pada
malonil KoA
sehingga C- dapat bertindak sebagai nukleofil
NADH
-NAD+
-HSCoA
Basa
Basa
Basa
(12)
(14)
ikli i
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siklisasi
HidroksilasiOksidasi/
dehidrogenasi
Reduksi
Reduksi/dehidroksilasi
Hidroksilasi
Oksidasi &isomerasi
Chalcon isomerase
Isoflavon synthaseflavon synthase Flavon 3-hidroxylase
Dihydroflavonol 4-reductase
Leucoanthocyanidinreductase
OHOH
OH O
OH
OOH
OH O
OH
OOH
OH O
OH
OOH
OH O
OH
OH
OOH
OH OOH
OOH
OH O
OH
OH
OH
OOH
OH
OH
OH
OH
OH
OOH
OH
OH
OH
OHORO
OR
OH
OH
OMe
OMe
Kalkon Flavanon
Flavon Isoflavon Dihidroflavonol
FlavonolFlavan-3,4-diol
Flavan-3-ol Anthocyanin
+
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Page 18Nila Huda - Kimia ITS
No Senyawa No Senyawa
1 Fosfoenolpiruvat 8 Fenilalanin
2 Eritrosa-4-Fosfat 9 Tirosin
3 Asam Shikimat 10 Asam Sinamat
4 Asam Chorismat 11 Asam p-Koumarat
5 Asam Prefenat 12 p-Koumaril KoA
6 Fenilpiruvat 13 Malonil KoA
7 4-Hidroksifenilpiruvat 14 Kalkon
DAFTAR PENOMORAN SENYAWA
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Claisen Rearrangement
A pericyclic reaction in which allyl vinylether is converted to
a rearrangementb,g-enone (sometimes called an oxa-
Cope rearrangement)
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