5.451 F2005
Shikimate Pathway Favonoids. Dewick 149-157
HO2C
O3P O DAHP
CO2
synthase
O3PO
O3PO O
H
HO
HO
O
OH
OH
OH
dehydroquinate shikimate
dehydroquinate
shikimate
dehydratase
dehydrogenase
synthase
kinase
CO2H
CO2H
HO CO2H
O
OH
OH
O
OH
HO
OH
OH
CO2H
O3PO
OH
OH
OH
CO2H
CO2
CoA-S
O3PO O
O
O3PO
O
CO2
OH
HO
NH2
chorismate
synthase
OH
CO2H
O
CO2H
OH
OH
HO
chorismate
mutase
NH2
CO2
O2C
H2N
CO2
O
COOH
OH
HO
CO2H
Tyr, Phe
5.451 F2005
Shikimate Pathway
Synthesis of Coumaroyl starting material
OH
OH
CO2
O2C
O
CO2H
OH
Ammonia Lyase
NH2
CO2H
CO2H
OH
CO2H
NH2
O
SCoA
5.451 F2005
Shikimate Pathway
Reactions of Coumaroyl starting material with 3 units of malonyl CoA
Flavonoids, flavonols, isoflavones
Stilbenes
Chalcone synthase/stilbene synthase superfamily
OH
OH
O
HO
O
S CoA
CHS
CHS
O
O
O
OH
HS
HS
O
SCoA
O
O
S-CoA
SCoA
OH
O
O
O
O
SCoA
5.451 F2005
Shikimate Pathway
Synthesis of Coumaroyl starting material
Reactions of Coumaroyl starting material
Condense coumaryl CoA with 3 units malonyl CoA
polyketide cyclizes and aromatizes
can occur with or without reduction
this yields a CHALCONE
5.451 F2005
Shikimate Pathway
flavonoid
Figure by MIT OCW.
3x malonyl CoA
L-phenylalanine
4 coumaroyl CoA
[CHR]
OH
HO
OH
4'
CHI HO 7
O 2
tt5
CHS
R
OH
3
O
R
R = OH Naringenin chalcone
R = H Isoliquiritigenin
HO
O
HO 7
OH
O
IFS
R
O
O
R = OH Naringenin
R = H Liquiritigenin
OH
R
O
4'
OH
R = OH Genistein
R = H Daidzein
F3H tt6
DFR
Condensed tannins
tt3
Anthocyanins
R
OH
HO
O
OH
R
O
R = H Kaempferol
R = OH Quercetin
Figure by MIT OCW.
PNAS2002 99 14578
Index of figures removed due to copyright reasons
Austin, Michael B., and Joseph P. Noel. Figures 8, 7, and 10 in “The chalcone synthase superfamily of type III polyketide
synthases.” Natural Product Reports 20 (2003): 79-110.
Turnbull, Jonathan J. et al. Figures 1 and 3 in “Mechanistic Studies on Three 2-Oxoglutarate-dependent Oxygenases of
Flavonoid Biosynthesis: Anthocyanidin Synthase, Flavonol Synthase, and Flavanone 3{Beta}-Hydroxylase.” J Biol Chem
279 (2004): 1206-1216.
http://www.jbc.org/cgi/reprint/279/2/1206
Hashim, Muhammed Faisal et al. Figure 2 in “Reaction mechamism of oxidative rearrangement of flavanone in isoflavone
biosynthesis.” FEBS Lett 271 (1990): 219-222.
Winkel-Shirley, Brenda. Figure 1 in “Flavonoid Biosynthesis. A Colorful Model for Genetics, Biochemistry, Cell Biology,
and Biotechnology.” Plant Physiol 126 (2001): 485-493.
http://www.plantphysiol.org/cgi/content/full/126/2/485
Austin, Michael B. et al. Figures 4 and 1 in “An Aldol Switch Discovered in Stilbene Synthases Mediates Cyclization
Specificity of Type III Polyketide Synthases.” Chem Bio 11 (2004): 1179-1194.
Fukusaki, Ei-ichiro et al. Figures 1 and 3 in “Flower color modulations of Torenia hybrida by downregulation of chalcone
synthase genes with RNA interference.” J Biotech 111 (2004): 229-240.
Xie, De-Yu et al. Figures 3 and 2 in “Role of Anthocyanidin Reductase, Encoded by BANYULS in Plant Flavonoid
Biosynthesis.” Science 299 (2003): 396-399.