ENTRY       osa00941                    Pathway
NAME        Flavonoid biosynthesis - Oryza sativa japonica (Japanese rice) (RefSeq)
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 osa00941  Flavonoid biosynthesis
MODULE      osa_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:osa00941]
DBLINKS     GO: 0009813
ORGANISM    Oryza sativa japonica (Japanese rice) (RefSeq) [GN:osa]
GENE        4350636  chalcone synthase 1 [KO:K00660] [EC:2.3.1.74]
            4342725  chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            4334588  chalcone--flavonone isomerase [KO:K01859] [EC:5.5.1.6]
            4349607  probable chalcone--flavonone isomerase 3 [KO:K01859] [EC:5.5.1.6]
            4351321  probable chalcone--flavonone isomerase 3 isoform X1 [KO:K01859] [EC:5.5.1.6]
            9270463  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            4330843  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
            4338409  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            4329324  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
            4329329  cytochrome P450 CYP73A100 [KO:K00487] [EC:1.14.14.91]
            9270590  LOW QUALITY PROTEIN: trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            4348304  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            4348299  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            4334886  cytochrome P450 93A2 [KO:K23180] [EC:1.14.19.76]
            4332919  flavonoid 3',5'-hydroxylase 1 [KO:K13083] [EC:1.14.14.81]
            4325716  leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
            4341576  leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
            4337100  anthocyanidin reductase [KO:K08695] [EC:1.3.1.77]
            4337102  anthocyanidin reductase isoform X1 [KO:K08695] [EC:1.3.1.77]
            4337101  anthocyanidin reductase [KO:K08695] [EC:1.3.1.77]
            4332311  leucoanthocyanidin reductase [KO:K13081] [EC:1.17.1.3]
            4351866  naringenin 7-O-methyltransferase [KO:K22440] [EC:2.1.1.232]
            4346205  shikimate O-hydroxycinnamoyltransferase isoform X1 [KO:K13065] [EC:2.3.1.133]
            4340333  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            4347092  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            4339188  cytochrome P450 98A1 [KO:K09754] [EC:1.14.14.96]
            4340240  caffeoyl-CoA O-methyltransferase 1 [KO:K00588] [EC:2.1.1.104]
            4347397  probable caffeoyl-CoA O-methyltransferase At4g26220 [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   PMID:16945088
  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   PMID:16367960
  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   PMID:16774647
  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   PMID:16832053
  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   PMID:15231405
  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   PMID:12828368
  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   PMID:12644647
  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   PMID:11073455
  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   PMID:16667183
  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
REL_PATHWAY osa00940  Phenylpropanoid biosynthesis
            osa00942  Anthocyanin biosynthesis
            osa00944  Flavone and flavonol biosynthesis
KO_PATHWAY  ko00941
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