KEGG   PATHWAY: rn00941
Entry
rn00941                     Pathway                                

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
rn00941  Flavonoid biosynthesis
rn00941

Module
M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:rn00941]
M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:rn00941]
Other DBs
GO: 0009813
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
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
R06615  (2R,3S)-afzelechin:NADP+ 4-oxidoreductase
R06820  UDP-L-rhamnose:flavanone-7-O-glucoside 2''-O-alpha-L-rhamnosyltransferase
R06822   
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)
R07991   
R07992   
R07993  flavanone,2-oxoglutarate:oxygen oxidoreductase (3-hydroxylating)
R07994   
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
R08000   
R08001   
R08002  liquiritigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R08003   
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
R08012   
R08013   
R08021  UDP-glucose:flavanone 7-O-beta-D-glucosyltransferase
R08022  UDP-L-rhamnose:hesperetin-7-O-glucoside 2''-O-alpha-L-rhamnosyltransferase
R08026   
R08028   
R08029   
R08031   
R08032  garbanzol,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R08081  flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R08082  dihydroflavonol,2-oxoglutarate:oxygen oxidoreductase
R08129   
R08130   
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
C00223  p-Coumaroyl-CoA
C00323  Caffeoyl-CoA
C00389  Quercetin
C00406  Feruloyl-CoA
C00509  Naringenin
C00540  Cinnamoyl-CoA
C00774  Phloretin
C00852  Chlorogenate
C00974  Dihydrokaempferol
C01378  Fustin
C01460  Vitexin
C01477  Apigenin
C01514  Luteolin
C01604  Phlorizin
C01617  Taxifolin
C01709  Hesperetin
C02906  Dihydromyricetin
C02947  4-Coumaroylshikimate
C03648  cis-3,4-Leucopelargonidin
C05334  Isosakuranetin
C05631  Eriodictyol
C05903  Kaempferol
C05904  Pelargonidin
C05905  Cyanidin
C05906  Leucocyanidin
C05907  Luteoforol
C05908  Delphinidin
C05909  Leucodelphinidin
C05911  Pentahydroxyflavanone
C06561  Naringenin chalcone
C06562  (+)-Catechin
C08578  Butein
C08650  Isoliquiritigenin
C09099  Naringenin 7-O-beta-D-glucoside
C09320  Afzelechin
C09614  Butin
C09727  (-)-Epicatechin
C09736  Fisetinidol-4beta-ol
C09751  Garbanzol
C09756  Homoeriodictyol
C09762  Liquiritigenin
C09789  Naringin
C09806  Neohesperidin
C09826  Pinobanksin
C09827  Pinocembrin
C09833  Sakuranetin
C10028  Chrysin
C10044  Galangin
C10107  Myricetin
C10192  Tricetin
C10434  5-O-Caffeoylshikimic acid
C12123  7,4'-Dihydroxyflavone
C12124  Apiforol
C12127  (+)-Gallocatechin
C12128  (-)-Epiafzelechin
C12136  (-)-Epigallocatechin
C12208  p-Coumaroyl quinic acid
C15525  Eriodictyol chalcone
C16404  Pinocembrin chalcone
C16405  Homoeriodictyol chalcone
C16406  Phlorizin 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
C16416  Desmethylxanthohumol
C16417  Xanthohumol
C16418  Pinobanksin 3-O-acetate
C16419  Pinostrobin
C16422  Hesperetin 7-O-glucoside
C16492  8-C-Glucosylnaringenin
C21913  Dihydro-4-coumaroyl-CoA
C22048  4-O-Methylxanthohumol
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
New Phytol 172:47-62 (2006)
DOI:10.1111/j.1469-8137.2006.01798.x
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
Plant J 45:133-43 (2006)
DOI:10.1111/j.1365-313X.2005.02625.x
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
Plant J 47:224-37 (2006)
DOI:10.1111/j.1365-313X.2006.02786.x
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
Proc Natl Acad Sci U S A 103:11075-80 (2006)
DOI:10.1073/pnas.0604246103
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
Plant Sci 170:587-595 (2006)
DOI:10.1016/j.plantsci.2005.10.013
Reference
  Authors
Stevens JF, Page JE.
  Title
Xanthohumol and related prenylflavonoids from hops and beer: to your good health!
  Journal
Phytochemistry 65:1317-30 (2004)
DOI:10.1016/j.phytochem.2004.04.025
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
Plant Biotechnol 21:367-375 (2004)
DOI:10.5511/plantbiotechnology.21.367
Reference
  Authors
Springob K, Nakajima J, Yamazaki M, Saito K.
  Title
Recent advances in the biosynthesis and accumulation of anthocyanins.
  Journal
Nat Prod Rep 20:288-303 (2003)
DOI:10.1039/b109542k
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
Plant Physiol 131:941-51 (2003)
DOI:10.1104/pp.004820
Reference
  Authors
Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K.
  Title
Biochemical formation of anthocyanins in silk tissue of Zea mays.
  Journal
Plant Sci 164:489-495 (2003)
DOI:10.1016/S0168-9452(02)00433-8
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
Biochem Eng J 14:227-235 (2003)
DOI:10.1016/S1369-703X(02)00224-3
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
Science 290:1163-6 (2000)
DOI:10.1126/science.290.5494.1163
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
Plant Physiol 91:1323-8 (1989)
DOI:10.1104/pp.91.4.1323
Related
pathway
rn00940  Phenylpropanoid biosynthesis
rn00942  Anthocyanin biosynthesis
rn00943  Isoflavonoid biosynthesis
rn00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   

DBGET integrated database retrieval system