KEGG   PATHWAY: vum00941
Entry
vum00941                    Pathway                                
Name
Flavonoid biosynthesis - Vigna umbellata (ricebean)
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
vum00941  Flavonoid biosynthesis
vum00941

Module
vum_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:vum00941]
vum_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:vum00941]
vum_M00940  Flavanone biosynthesis, p-coumaroyl-CoA => liquiritigenin [PATH:vum00941]
Other DBs
GO: 0009813
Organism
Vigna umbellata (ricebean) [GN:vum]
Gene
124844025  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
124844026  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
124844028  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
124820777  chalcone synthase 17 [KO:K00660] [EC:2.3.1.74]
124845001  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
124823398  chalcone synthase [KO:K00660] [EC:2.3.1.74]
124823446  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
124836030  chalcone synthase 17-like [KO:K00660] [EC:2.3.1.74]
124827397  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
124841157  chalcone synthase-like [KO:K00660] [EC:2.3.1.74]
124821786  chalcone isomerase-like protein 2 [KO:K01859] [EC:5.5.1.6]
124846774  chalcone--flavanone isomerase-like [KO:K01859] [EC:5.5.1.6]
124822906  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
124821209  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
124819703  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
124819704  flavonol synthase/flavanone 3-hydroxylase-like [KO:K05278] [EC:1.14.20.6]
124828697  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
124830235  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
124843217  cytochrome P450 CYP73A100-like [KO:K00487] [EC:1.14.14.91]
124847694  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
124838841  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
124842404  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
124819729  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
124819885  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
124831673  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
124831674  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
124831675  NAD(P)H-dependent 6'-deoxychalcone synthase-like [KO:K08243]
124828505  flavonoid 3'-monooxygenase-like [KO:K05280] [EC:1.14.14.82]
124830858  flavonoid 3'-monooxygenase-like [KO:K05280] [EC:1.14.14.82]
124830859  flavonoid 3'-monooxygenase-like [KO:K05280] [EC:1.14.14.82]
124830594  dihydroflavonol 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
124830645  dihydroflavonol 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
124830655  dihydroflavonol 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
124819993  flavonoid 3',5'-hydroxylase 2-like [KO:K13083] [EC:1.14.14.81]
124836972  leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
124822721  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
124841586  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
124841588  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
124830583  anthocyanidin reductase ((2S)-flavan-3-ol-forming)-like [KO:K08695] [EC:1.3.1.77]
124829599  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
124829602  leucoanthocyanidin reductase-like [KO:K13081] [EC:1.17.1.3]
124825999  UDP-glycosyltransferase 88F5-like [KO:K22845] [EC:2.4.1.357]
124834861  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
124834862  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
124835901  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
124835922  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
124848202  LOW QUALITY PROTEIN: acetyl-CoA-benzylalcohol acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
124825394  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
124825722  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
124825738  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
124839131  fatty alcohol:caffeoyl-CoA acyltransferase [KO:K13065] [EC:2.3.1.133]
124841123  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
124841124  stemmadenine O-acetyltransferase-like [KO:K13065] [EC:2.3.1.133]
124843270  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
124843288  shikimate O-hydroxycinnamoyltransferase-like [KO:K13065] [EC:2.3.1.133]
124820009  spermidine hydroxycinnamoyl transferase-like [KO:K13065] [EC:2.3.1.133]
124831523  omega-hydroxypalmitate O-feruloyl transferase-like [KO:K13065] [EC:2.3.1.133]
124835773  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
124823922  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
124848337  caffeoyl-CoA O-methyltransferase 1-like [KO:K00588] [EC:2.1.1.104]
124848430  uncharacterized protein LOC124848430 [KO:K00588] [EC:2.1.1.104]
124848493  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
124831121  caffeoyl-CoA O-methyltransferase-like [KO:K00588] [EC:2.1.1.104]
124843510  flavonoid 3',5'-methyltransferase-like [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
vum00940  Phenylpropanoid biosynthesis
vum00942  Anthocyanin biosynthesis
vum00943  Isoflavonoid biosynthesis
vum00944  Flavone and flavonol biosynthesis
KO pathway
ko00941   
LinkDB

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