PATHWAY: rn00941 Help
Entry Name Flavonoid biosynthesis
Description Flavonoids are a major class of plant secondary metabolites that serves a multitude of functions including pigments and antioxidant activity. Flavonoids are synthesized from phenylpropanoid derivatives by condensation with malonyl-CoA. For example, condensation of p-coumaroyl-CoA (C6-C3) with three malonyl-CoA (C3) molecules results in naringenin chalcone with a diphenylpropane (C6-C3-C6) unit, which is converted to naringenin with the flavone (2-phenylchromen-4-one) backbone by conjugate ring closure. These and further modifications yield a variety of structural forms including chalcones, flavanones, dihyroflavonols, and flavans, anthocyanins, flavones and flavonols, and isoflavonoids.
Class Metabolism; Biosynthesis of other secondary metabolites
Pathway map Module M00137 Flavanone biosynthesis, phenylalanine => naringenin [PATH:rn00941 ]
M00138 Flavonoid biosynthesis, naringenin => pelargonidin [PATH:rn00941 ]
M00940 Flavanone biosynthesis, p-coumaroyl-CoA => liquiritigenin [PATH:rn00941 ]
Other DBs Reaction R01613 malonyl-CoA:4-coumaroyl-CoA malonyltransferase(cyclizing)
R01942 S-adenosyl-L-methionine:caffeoyl-CoA 3-O-methyltransferase
R01945 caffeoyl-CoA:quinate O-(3,4-dihydroxycinnamoyl)transferase
R02160 dihydroflavonol,2-oxoglutarate:oxygen oxidoreductase
R02416 4-coumaroyl-CoA:shikimate O-(hydroxycinnamoyl)transferase
R02442 naringenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R02444 flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
R02445 flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R02446 flavanone lyase (decyclizing)
R02897 UDPglucose:flavanone 7-O-beta-D-glucosyltransferase
R03123 cis-3,4-leucopelargonidin:NADP+ 4-oxidoreductase
R03124 dihydrokaempferol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R03126 dihydroflavonol,2-oxoglutarate:oxygen oxidoreductase
R03590 flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R03636 leucocyanidin:NADP+ 4-oxidoreductase
R03639 taxifolin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R03640 flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
R04276 leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R04342 trans-5-O-(4-coumaroyl)-D-quinate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R04901 (2S)-flavan-4-ol:NADP+ 4-oxidoreductase; cis-3,4-leucopelargonidin:NADP+ 4-oxidoreductase
R04902 eriodictyol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R05036 leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R05037 leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R05038 leucodelphinidin:NADP+ 4-oxidoreductase
R05039 flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
R05723 leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R06532 (2R,3S)-catechin:NADP+ 4-oxidoreductase
R06533 (2R,3S)-gallocatechin:NADP+ 4-oxidoreductase
R06537 apigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R06538 kaempferol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R06539 dihydroflavonol,2-oxoglutarate:oxygen oxidoreductase
R06540 leucocyanidin,2-oxoglutarate:oxygen oxidoreductase
R06541 flavan-3-ol:NADP+ oxidoreductase
R06542 flavan-3-ol:NADP+ oxidoreductase
R06543 flavan-3-ol:NADP+ oxidoreductase
R06551 flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R06556 flavanone lyase (decyclizing)
R06568 malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing, reducing)
R06582 trans-5-O-(4-coumaroyl)-D-shikimate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R06610 (2S)-flavan-4-ol:NADP+ 4-oxidoreductase; cis-3,4-leucopelargonidin:NADP+ 4-oxidoreductase
R06615 (2R,3S)-afzelechin:NADP+ 4-oxidoreductase
R06820 UDP-L-rhamnose:flavanone-7-O-glucoside 2''-O-alpha-L-rhamnosyltransferase
R07432 p-coumaroyl-CoA:quinate hydroxycinnamoyltransferase
R07433 5-O-caffeoylshikimic acid:shikimate hydroxycinnamoyltransferase
R07436 p-coumaroyl-CoA:caffeoyl-CoA 3-hydroxylase
R07712 flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R07987 malonyl-CoA:cinnamoyl-CoA malonyltransferase (cyclizing)
R07988 malonyl-CoA:caffeoyl-CoA malonyltransferase (cyclizing)
R07989 malonyl-CoA:feruloyl-CoA malonyltransferase (cyclizing)
R07990 flavanone lyase (decyclizing)
R07993 flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
R07995 flavanone lyase (decyclizing)
R07996 flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
R07997 flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
R07998 5-deoxyleucopelargonidin:NADP+ 4-oxidoreductase
R07999 5-deoxyleucocyanidin:NADP+ 4-oxidoreductase
R08002 liquiritigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R08004 S-adenosyl-L-methionine:desmethylxanthohumol 6'-O-methyltransferase
R08006 UDP-alpha-D-glucose:2',4,4',6'-tetrahydroxychalcone 4'-O-beta-D-glucosyltransferase
R08007 UDP-alpha-D-glucose:2',3,4,4',6'-pentahydroxychalcone 4'-O-beta-D-glucosyltransferase
R08008 2',4,4',6'-tetrahydroxychalcone 4'-O-glucoside:oxygen oxidoreductase
R08009 2',3,4,4',6'-peptahydroxychalcone 4'-O-glucoside:oxygen oxidoreductase
R08010 2',3,4,4',6'-peptahydroxychalcone 4'-O-glucoside:oxygen oxidoreductase
R08021 UDP-glucose:flavanone 7-O-beta-D-glucosyltransferase
R08022 UDP-L-rhamnose:hesperetin-7-O-glucoside 2''-O-alpha-L-rhamnosyltransferase
R08032 garbanzol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R08081 flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R08082 dihydroflavonol,2-oxoglutarate:oxygen oxidoreductase
R08815 cinnamoyl-CoA,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (4-hydroxylating)
R09791 S-adenosyl-L-methionine:(2S)-5,7,4'-trihydroxyflavanone 7-O-methyltransferase
R10258 quercetin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R10260 luteolin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
R12088 UDP-alpha-D-glucose:phloretin 2'-O-D-glucosyltransferase
R12112 dihydro-4-coumaroyl-CoA:NADP+ 2,3-oxidoreductase
R12117 malonyl-CoA:dihydro-4-coumaroyl-CoA malonyltransferase(cyclizing)
R12213 S-adenosyl-L-methionine:naringenin 4'-O-methyltransferase
R12264 S-adenosyl-L-methionine:xanthohumol 4-O-methyltransferase
R12277 liquiritigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7,4'-dihydroxyflavone-forming)
R12278 naringenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (apigenin-forming)
R12279 eriodictyol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (luteolin-forming)
Compound C03648 cis-3,4-Leucopelargonidin
C09099 Naringenin 7-O-beta-D-glucoside
C10434 5-O-Caffeoylshikimic acid
C12208 p-Coumaroyl quinic acid
C16405 Homoeriodictyol chalcone
C16407 2',4,4',6'-Tetrahydroxychalcone 4'-O-glucoside
C16408 2',3,4,4',6'-Peptahydroxychalcone 4'-O-glucoside
C16409 Aureusidin 6-O-glucoside
C16410 Bracteatin 6-O-glucoside
C16415 5-Deoxyleucopelargonidin
C16418 Pinobanksin 3-O-acetate
C16422 Hesperetin 7-O-glucoside
C21913 Dihydro-4-coumaroyl-CoA
Reference Authors Tsai CJ, Harding SA, Tschaplinski TJ, Lindroth RL, Yuan Y.
Title Genome-wide analysis of the structural genes regulating defense phenylpropanoid metabolism in Populus.
Journal Reference Authors Ono E, Hatayama M, Isono Y, Sato T, Watanabe R, Yonekura-Sakakibara K, Fukuchi-Mizutani M, Tanaka Y, Kusumi T, Nishino T, Nakayama T.
Title Localization of a flavonoid biosynthetic polyphenol oxidase in vacuoles.
Journal Reference Authors Morreel K, Goeminne G, Storme V, Sterck L, Ralph J, Coppieters W, Breyne P, Steenackers M, Georges M, Messens E, Boerjan W.
Title Genetical metabolomics of flavonoid biosynthesis in Populus: a case study.
Journal Reference Authors Ono E, Fukuchi-Mizutani M, Nakamura N, Fukui Y, Yonekura-Sakakibara K, Yamaguchi M, Nakayama T, Tanaka T, Kusumi T, Tanaka Y.
Title Yellow flowers generated by expression of the aurone biosynthetic pathway.
Journal Reference Authors Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K.
Title Synthesis of (14C)-labeled 5-deoxyflavonoids and their application in the study of dihydroflavonol/leucoanthocyanidin interconversion by dihydroflavonol 4-reductase.
Journal Reference Authors Stevens JF, Page JE.
Title Xanthohumol and related prenylflavonoids from hops and beer: to your good health!
Journal Reference Authors Ogata J, Itoh Y, Ishida M, Yoshida H, Ozeki Y
Title Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus.
Journal Reference Authors Springob K, Nakajima J, Yamazaki M, Saito K.
Title Recent advances in the biosynthesis and accumulation of anthocyanins.
Journal Reference Authors Shimada N, Aoki T, Sato S, Nakamura Y, Tabata S, Ayabe S.
Title A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legume-specific 5-deoxy(iso)flavonoids in Lotus japonicus.
Journal Reference Authors Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K.
Title Biochemical formation of anthocyanins in silk tissue of Zea mays.
Journal Reference Authors Martens S, Knott J, Seitz CA, Janvari L, Yu SN, Forkmann G.
Title Impact of biochemical pre-studies on specific metabolic engineering strategies of flavonoid biosynthesis in plant tissues.
Journal Reference Authors Nakayama T, Yonekura-Sakakibara K, Sato T, Kikuchi S, Fukui Y, Fukuchi-Mizutani M, Ueda T, Nakao M, Tanaka Y, Kusumi T, Nishino T.
Title Aureusidin synthase: a polyphenol oxidase homolog responsible for flower coloration.
Journal Reference Authors Lewinsohn E, Britsch L, Mazur Y, Gressel J
Title Flavanone Glycoside Biosynthesis in Citrus: Chalcone Synthase, UDP-Glucose:Flavanone-7-O-Glucosyl-Transferase and -Rhamnosyl-Transferase Activities in Cell-Free Extracts.
Journal Related rn00940 Phenylpropanoid biosynthesis
rn00944 Flavone and flavonol biosynthesis
KO pathway
