KEGG   PATHWAY: vun00941
Entry
vun00941                    Pathway                                
Name
Flavonoid biosynthesis - Vigna unguiculata (cowpea)
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
vun00941  Flavonoid biosynthesis
vun00941

Module
vun_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:vun00941]
vun_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:vun00941]
vun_M00940  Flavanone biosynthesis, p-coumaroyl-CoA => liquiritigenin [PATH:vun00941]
Other DBs
GO: 0009813
Organism
Vigna unguiculata (cowpea) [GN:vun]
Gene
114195889  chalcone synthase 2-like [KO:K00660] [EC:2.3.1.74]
114190241  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
114173395  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114173396  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114173397  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114173398  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114173399  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114173400  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114187259  chalcone synthase [KO:K00660] [EC:2.3.1.74]
114170449  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114187056  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
114169233  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114175142  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114164804  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
114168795  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114168796  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
114173536  chalcone synthase 17 [KO:K00660] [EC:2.3.1.74]
114192130  chalcone--flavonone isomerase [KO:K01859] [EC:5.5.1.6]
114189846  chalcone--flavonone isomerase 1B-2-like [KO:K01859] [EC:5.5.1.6]
114190515  chalcone--flavonone isomerase-like [KO:K01859] [EC:5.5.1.6]
114162209  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
114179503  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
114193841  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
114180972  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
114193905  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
114187493  trans-cinnamate 4-monooxygenase-like [KO:K00487] [EC:1.14.14.91]
114189889  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
114164472  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
114193329  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
114193203  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
114185986  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
114189600  NAD(P)H-dependent 6'-deoxychalcone synthase-like isoform X1 [KO:K08243]
114163850  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
114162156  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
114169631  licodione synthase-like [KO:K23179] [EC:1.14.19.76]
114164840  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
114191920  dihydroflavonol 4-reductase-like isoform X1 [KO:K13082] [EC:1.1.1.219 1.1.1.234]
114193233  dihydroflavonol 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
114193234  dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
114193708  dihydroflavonol 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
114187675  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
114186854  flavonoid 3',5'-hydroxylase 1-like [KO:K13083] [EC:1.14.14.81]
114173327  leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
114179528  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
114176923  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
114190745  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
114186935  UDP-glycosyltransferase 88F5-like isoform X1 [KO:K22845] [EC:2.4.1.357]
114186948  UDP-glycosyltransferase 88F5-like [KO:K22845] [EC:2.4.1.357]
114186917  UDP-glycosyltransferase 88F5-like isoform X1 [KO:K22845] [EC:2.4.1.357]
114165189  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
114188972  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114188979  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114177503  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114178886  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114178887  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114185954  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
114186815  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114186979  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114167094  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
114187412  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114187506  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114187552  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114187600  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114187617  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114187628  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114187632  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114184832  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
114179972  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114176021  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114181075  omega-hydroxypalmitate O-feruloyl transferase-like [KO:K13065] [EC:2.3.1.133]
114181608  fatty alcohol:caffeoyl-CoA acyltransferase [KO:K13065] [EC:2.3.1.133]
114165158  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
114163969  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114165191  vinorine synthase-like [KO:K13065] [EC:2.3.1.133]
114185566  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
114187064  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
114186352  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
114175063  caffeoyl-CoA O-methyltransferase 3-like [KO:K00588] [EC:2.1.1.104]
114176655  flavonoid 3',5'-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
114174890  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
114179485  caffeoyl-CoA O-methyltransferase 5-like [KO:K00588] [EC:2.1.1.104]
114176528  caffeoyl-CoA O-methyltransferase 5-like [KO:K00588] [EC:2.1.1.104]
114177780  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
114176743  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
114173033  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
114179722  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
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
vun00940  Phenylpropanoid biosynthesis
vun00942  Anthocyanin biosynthesis
vun00943  Isoflavonoid biosynthesis
vun00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   
LinkDB

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