DAHPsynthasedehydroquinatesynthasedehydroquinatedehydrataseshikimatedehydrogenaseshikimatekinasechorismatesynthasechorismatemutaseCO2HHOOHOHCO2HOOHOHOOHOHHO CO2HOHOOHOHCO2O3POO3POHO OHOHO3POHO2COHOOHNH2CO2O3POCO2HO3POOHOHCO2HO3POOHO CO2CO2HOHO CO2OHO2CCO2OTyr, PheCoA-S OCO2HNH2HOHOCO2HCOOHH2NOH5.451 F2005Shikimate Pathway Favonoids. Dewick 149-1575.451 F2005Shikimate PathwaySynthesis of Coumaroyl starting materialOHO2CCO2ONH2CO2HCO2HCO2HOHNH2CO2HOHOHSCoAOAmmonia Lyase5.451 F2005Shikimate PathwayReactions of Coumaroyl starting material with 3 units of malonyl CoAFlavonoids, flavonols, isoflavonesStilbenesChalcone synthase/stilbene synthase superfamilyCHSHO SO OCoAHSOHSCoAOOHO SCoAOCHSHSOHOOS-CoAOOHOO OSCoAO5.451 F2005Shikimate PathwaySynthesis of Coumaroyl starting materialReactions of Coumaroyl starting materialCondense coumaryl CoA with 3 units malonyl CoApolyketide cyclizes and aromatizescan occur with or without reductionthis yields a CHALCONE5.451 F2005Shikimate PathwayflavonoidPNAS2002 99 14578L-phenylalanine4 coumaroyl CoA3x malonyl CoACHS[CHR]OHOHHOR OOOHHOR OOHOR OOHOHOHOR OOHR = OH Naringenin chalconeR = H IsoliquiritigeninR = OH NaringeninR = H LiquiritigeninR = OH GenisteinR = H DaidzeinCHItt5Condensed tanninsAnthocyaninsOOHHOR OR = H KaempferolR = OH QuercetinOHRF3Htt6DFRtt37234'74'IFSFigure by MIT OCW.Figure by MIT OCW.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):