ENTRY       ath00941                    Pathway
NAME        Flavonoid biosynthesis - Arabidopsis thaliana (thale cress)
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 ath00941  Flavonoid biosynthesis
MODULE      ath_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:ath00941]
            ath_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:ath00941]
DBLINKS     GO: 0009813
ORGANISM    Arabidopsis thaliana (thale cress) [GN:ath]
GENE        AT5G13930  TT4; Chalcone and stilbene synthase family protein [KO:K00660] [EC:2.3.1.74]
            AT5G66220  Chalcone-flavanone isomerase family protein [KO:K01859] [EC:5.5.1.6]
            AT3G55120  TT5; Chalcone-flavanone isomerase family protein [KO:K01859] [EC:5.5.1.6]
            AT5G05270  CHIL; Chalcone-flavanone isomerase family protein [KO:K01859] [EC:5.5.1.6]
            AT3G51240  F3H; flavanone 3-hydroxylase [KO:K00475] [EC:1.14.11.9]
            AT5G08640  FLS1; flavonol synthase 1 [KO:K05278] [EC:1.14.20.6]
            AT5G63590  FLS3; flavonol synthase 3 [KO:K05278] [EC:1.14.20.6]
            AT5G43935  FLS6; flavonol synthase 6 [KO:K05278] [EC:1.14.20.6]
            AT5G63600  FLS5; flavonol synthase 5 [KO:K05278] [EC:1.14.20.6]
            AT5G63595  FLS4; flavonol synthase 4 [KO:K05278] [EC:1.14.20.6]
            AT5G63580  FLS2; flavonol synthase 2 [KO:K05278] [EC:1.14.20.6]
            AT2G30490  C4H; cinnamate-4-hydroxylase [KO:K00487] [EC:1.14.14.91]
            AT5G07990  TT7; Cytochrome P450 superfamily protein [KO:K05280] [EC:1.14.14.82]
            AT5G42800  DFR; dihydroflavonol 4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
            AT4G22870  2-oxoglutarate (2OG) and Fe(II)-dependent oxygenase superfamily protein [KO:K05277] [EC:1.14.20.4]
            AT4G22880  LDOX; leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
            AT1G61720  BAN; NAD(P)-binding Rossmann-fold superfamily protein [KO:K08695] [EC:1.3.1.77]
            AT5G48930  HCT; hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            AT2G19070  SHT; spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            AT5G57840  HXXXD-type acyl-transferase family protein [KO:K13065] [EC:2.3.1.133]
            AT2G40890  CYP98A3; cytochrome P450, family 98, subfamily A, polypeptide 3 [KO:K09754] [EC:1.14.14.96]
            AT4G34050  CCoAOMT1; S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K00588] [EC:2.1.1.104]
            AT1G24735  S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K00588] [EC:2.1.1.104]
            AT1G67980  CCOAMT; caffeoyl-CoA 3-O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            AT4G26220  S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [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 ath00940  Phenylpropanoid biosynthesis
            ath00942  Anthocyanin biosynthesis
            ath00944  Flavone and flavonol biosynthesis
KO_PATHWAY  ko00941
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