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Entry
dosa00941                   Pathway                                

Name
Flavonoid biosynthesis - Oryza sativa japonica (Japanese rice) (RAPDB)
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
BRITE hierarchy
Pathway map
Flavonoid biosynthesis
dosa00941

All organismsOrtholog table
Module
Flavanone biosynthesis, phenylalanine => naringenin [PATH:dosa00941]
Flavonoid biosynthesis, naringenin => pelargonidin [PATH:dosa00941]
Other DBs
BSID: 
GO: 
Organism
Oryza sativa japonica (Japanese rice) (RAPDB) [GN:dosa]
Gene
Os11g0530600; Similar to Chalcone synthase C2 (EC 2.3.1.74) (Naringenin-chalcone synthase C2). [KO:K00660] [EC:2.3.1.74]
Os07g0214900; Similar to Chalcone synthase C2 (EC 2.3.1.74) (Naringenin-chalcone synthase C2). [KO:K00660] [EC:2.3.1.74]
Os03g0819600; Chalcone isomerase (EC 5.5.1.6). [KO:K01859] [EC:5.5.1.6]
Os04g0662600; Similar to Naringenin,2-oxoglutarate 3-dioxygenase. [KO:K00475] [EC:1.14.11.9]
Os02g0767300; Similar to Flavonol synthase/flavanone 3-hydroxylase (EC 1.14.11.23) (EC 1.14.11.9) (FLS) (CitFLS). [KO:K05278] [EC:1.14.11.23]
Os05g0320700; Similar to Cytochrome P450. [KO:K00487] [EC:1.14.13.11]
Os02g0467600; Similar to Cinnamate 4-hydroxylase CYP73. [KO:K00487] [EC:1.14.13.11]
Os02g0467000; Similar to trans-cinnamate 4-monooxygenase. [KO:K00487] [EC:1.14.13.11]
Os10g0320100; Similar to Flavonoid 3'-monooxygenase (EC 1.14.13.21) (Flavonoid 3'-hydroxylase) (Cytochrome P450 75B2). [KO:K05280] [EC:1.14.13.21]
Os10g0317900; Similar to Flavonoid 3'-monooxygenase (EC 1.14.13.21) (Flavonoid 3'-hydroxylase) (Cytochrome P450 75B2). [KO:K05280] [EC:1.14.13.21]
Os01g0372500; Similar to Leucoanthocyanidin dioxygenase (EC 1.14.11.19) (LDOX) (Leucocyanidin oxygenase) (Leucoanthocyanidin hydroxylase). [KO:K05277] [EC:1.14.11.19]
Os06g0626700; Isopenicillin N synthase family protein. [KO:K05277] [EC:1.14.11.19]
Os04g0630800; Similar to Anthocyanidin reductase. [KO:K08695] [EC:1.3.1.77]
Os04g0631000; Similar to H0105C05.4 protein. [KO:K08695] [EC:1.3.1.77]
Os04g0630300; NAD(P)-binding domain containing protein. [KO:K08695] [EC:1.3.1.77]
Os04g0630400; NAD(P)-binding domain containing protein. [KO:K08695] [EC:1.3.1.77]
Os04g0630600; Similar to H0323C08.16 protein. [KO:K08695] [EC:1.3.1.77]
Os03g0259400; Similar to Leucoanthocyanidin reductase (EC 1.17.1.3) (Leucocyanidin reductase). [KO:K13081] [EC:1.17.1.3]
Os02g0611800; Similar to Hydroxyanthranilate hydroxycinnamoyltransferase 3. [KO:K13065] [EC:2.3.1.133]
Os04g0500700; Similar to Hydroxyanthranilate hydroxycinnamoyltransferase 3. [KO:K13065] [EC:2.3.1.133]
Os06g0184900; Transferase family protein. [KO:K13065] [EC:2.3.1.133]
Os08g0205000; Transferase domain containing protein. [KO:K13065] [EC:2.3.1.133]
Os05g0494000; Similar to Cytochrome P450 98A1 (EC 1.14.-.-). [KO:K09754] [EC:1.14.13.36]
Os10g0196100; Similar to Cytochrome P450 98A1. [KO:K09754] [EC:1.14.13.36]
Os01g0633500; Similar to Dihydroflavonol reductase. [KO:K13082] [EC:1.1.1.234 1.1.1.219]
Os08g0498100; Similar to Caffeoyl-CoA O-methyltransferase 2 (EC 2.1.1.104) (Trans-caffeoyl-CoA 3-O-methyltransferase 2) (CCoAMT-2) (CCoAOMT-2). [KO:K00588] [EC:2.1.1.104]
Os09g0481400; Similar to Caffeoyl-CoA O-methyltransferase (EC 2.1.1.104) (Trans-caffeoyl-CoA 3- O-methyltransferase) (CCoAMT) (CCoAOMT). [KO:K00588] [EC:2.1.1.104]
Os06g0165800; Similar to Caffeoyl-CoA 3-O-methyltransferase (Fragment). [KO:K00588] [EC:2.1.1.104]
Os03g0367101; Similar to cytochrome P450 flavonoid 3',5'-hydroxylase. [KO:K13083] [EC:1.14.13.88]
Compound
C00223  
p-Coumaroyl-CoA
C00323  
Caffeoyl-CoA
C00389  
Quercetin
C00406  
Feruloyl-CoA
C00509  
Naringenin
C00540  
Cinnamoyl-CoA
C00852  
Chlorogenate
C00974  
Dihydrokaempferol
C01378  
Fustin
C01460  
Vitexin
C01477  
Apigenin
C01514  
Luteolin
C01617  
Taxifolin
C01709  
Hesperetin
C02906  
Dihydromyricetin
C02947  
4-Coumaroylshikimate
C03648  
cis-3,4-Leucopelargonidin
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
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
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)
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)
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)
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)
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 Science 170(3): 587-595 (2006)
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)
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 Biotechnology 21(5):367-375 (2004)
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)
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)
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 Science 164(4):489-495 (2003)
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
Biochemical Engineering Journal 14(3):227-235 (2003)
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)
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)
KO pathway
 

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