ENTRY       gmx00941                    Pathway
NAME        Flavonoid biosynthesis - Glycine max (soybean)
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 gmx00941  Flavonoid biosynthesis
MODULE      gmx_M00137  Flavanone biosynthesis, phenylalanine => naringenin [PATH:gmx00941]
            gmx_M00138  Flavonoid biosynthesis, naringenin => pelargonidin [PATH:gmx00941]
            gmx_M00940  Flavanone biosynthesis, p-coumaroyl-CoA => liquiritigenin [PATH:gmx00941]
DBLINKS     GO: 0009813
ORGANISM    Glycine max (soybean) [GN:gmx]
GENE        106799718  CHS5; chalcone synthase 5 [KO:K00660] [EC:2.3.1.74]
            100779649  CHS4A; chalcone synthase 4a [KO:K00660] [EC:2.3.1.74]
            100785554  CHS11; chalcone synthase 11 [KO:K00660] [EC:2.3.1.74]
            100788048  CHS10; chalcone synthase 10 [KO:K00660] [EC:2.3.1.74]
            732575  CHS1; chalcone synthase 1 [KO:K00660] [EC:2.3.1.74]
            100782897  CHS7; chalcone synthase 7 [KO:K00660] [EC:2.3.1.74]
            100789075  CHS3C; chalcone synthase 3 [KO:K00660] [EC:2.3.1.74]
            100790997  CHS9; chalcone synthase 9 [KO:K00660] [EC:2.3.1.74]
            100792581  CHS4B; chalcone synthase 4b [KO:K00660] [EC:2.3.1.74]
            100809433  CHS6; chalcone synthase 6 [KO:K00660] [EC:2.3.1.74]
            100791524  CHS3; chalcone synthase 3 [KO:K00660] [EC:2.3.1.74]
            100170701  CHS8; chalcone synthase [KO:K00660] [EC:2.3.1.74]
            100775264  CHS13; chalcone synthase 13 [KO:K00660] [EC:2.3.1.74]
            106794283  CHS3B; chalcone synthase 3-like [KO:K00660] [EC:2.3.1.74]
            102663074  LOW QUALITY PROTEIN: chalcone synthase 3 [KO:K00660] [EC:2.3.1.74]
            121175284  chalcone synthase 1 [KO:K00660] [EC:2.3.1.74]
            114827817  CHS2; chalcone synthase 2 [KO:K00660] [EC:2.3.1.74]
            121175285  chalcone synthase 3 [KO:K00660] [EC:2.3.1.74]
            547602  CHI1A; chalcone--flavonone isomerase 1A [KO:K01859] [EC:5.5.1.6]
            732546  CHI2-A; chalcone--flavonone isomerase 2-A [KO:K01859] [EC:5.5.1.6]
            732545  CHI1B1; chalcone--flavonone isomerase 1B-1 [KO:K01859] [EC:5.5.1.6]
            100037455  CHI1B2; chalcone--flavonone isomerase 1B-2 [KO:K01859] [EC:5.5.1.6]
            732547  CHI4A; chalcone isomerase 4A [KO:K01859] [EC:5.5.1.6]
            778027  CHI4B; chalcone isomerase 4B [KO:K01859] [EC:5.5.1.6]
            100780057  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            100818312  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            732548  F3H; flavanone 3-hydroxylase [KO:K00475] [EC:1.14.11.9]
            100799462  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            100815441  naringenin,2-oxoglutarate 3-dioxygenase [KO:K00475] [EC:1.14.11.9]
            100816829  flavonol synthase/flavanone 3-hydroxylase [KO:K05278] [EC:1.14.20.6]
            778157  FLS1; flavonol synthase [KO:K05278] [EC:1.14.20.6]
            100810937  uncharacterized protein LOC100810937 [KO:K05278] [EC:1.14.20.6]
            100499623  C4H; trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            100818985  trans-cinnamate 4-monooxygenase [KO:K00487] [EC:1.14.14.91]
            100812188  C4H1; cinnamate 4-hydroxylase [KO:K00487] [EC:1.14.14.91]
            547911  CHR1; chalcone reductase CHR1 [KO:K08243]
            100800931  CHR6; chalcone reductase CHR6 [KO:K08243]
            100820161  CHR5; chalcone reductase CHR5 [KO:K08243]
            100790074  CHR4; chalcone reductase CHR4 [KO:K08243]
            100788544  NAD(P)H-dependent 6'-deoxychalcone synthase [KO:K08243]
            100783503  FNSII-1; cytochrome P450 93B16 [KO:K23179] [EC:1.14.19.76]
            100784036  FNSII-2; flavone synthase II [KO:K23179] [EC:1.14.19.76]
            547475  SF3'H1; flavonoid 3'-hydroxylase [KO:K05280] [EC:1.14.14.82]
            100777999  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            100778531  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            100779588  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            100807293  flavonoid 3'-monooxygenase [KO:K05280] [EC:1.14.14.82]
            548087  DFR1; dihydroflavonol-4-reductase DFR1 [KO:K13082] [EC:1.1.1.219 1.1.1.234]
            732626  DFR2; dihydroflavonol-4-reductase [KO:K13082] [EC:1.1.1.219 1.1.1.234]
            100778253  bifunctional dihydroflavonol 4-reductase/flavanone 4-reductase-like [KO:K13082] [EC:1.1.1.219 1.1.1.234]
            547705  W1; flavonoid 3', 5'-hydroxylase [KO:K13083] [EC:1.14.14.81]
            547615  ANS2; anthocyanidin synthase [KO:K05277] [EC:1.14.20.4]
            100801148  ANS3; leucoanthocyanidin dioxygenase [KO:K05277] [EC:1.14.20.4]
            100805127  ANR1; anthocyanidin reductase 1 [KO:K08695] [EC:1.3.1.77]
            100817081  ANR2; anthocyanidin reductase 2 [KO:K08695] [EC:1.3.1.77]
            100786879  LAR1; leucoanthocyanidin reductase [KO:K13081] [EC:1.17.1.3]
            100795100  leucoanthocyanidin reductase [KO:K13081] [EC:1.17.1.3]
            100776621  SOMT-2; flavonoid 4'-O-methyltransferase-like [KO:K23053] [EC:2.1.1.231]
            100787088  IF7GT6; isoflavone 7-O-glucosyltransferase UGT6 [KO:K22845] [EC:2.4.1.357]
            100806561  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            100820075  shikimate O-hydroxycinnamoyltransferase isoform X3 [KO:K13065] [EC:2.3.1.133]
            100499712  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
            100777157  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100777680  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100779280  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100779814  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100792323  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
            100814459  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100804886  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100805962  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100801695  stemmadenine O-acetyltransferase [KO:K13065] [EC:2.3.1.133]
            100801923  shikimate O-hydroxycinnamoyltransferase [KO:K13065] [EC:2.3.1.133]
            100787038  spermidine hydroxycinnamoyl transferase isoform X2 [KO:K13065] [EC:2.3.1.133]
            100802888  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100803418  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100778626  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100780971  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
            100819383  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100775549  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100805510  fatty alcohol:caffeoyl-CoA acyltransferase [KO:K13065] [EC:2.3.1.133]
            100777007  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100777532  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100779652  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100305576  omega-hydroxypalmitate O-feruloyl transferase [KO:K13065] [EC:2.3.1.133]
            100788434  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100789491  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            102668997  vinorine synthase [KO:K13065] [EC:2.3.1.133]
            100802808  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            100778266  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            102663900  spermidine hydroxycinnamoyl transferase [KO:K13065] [EC:2.3.1.133]
            102670206  stemmadenine O-acetyltransferase isoform X1 [KO:K13065] [EC:2.3.1.133]
            100811080  cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
            606506  CYP98A2; cytochrome P450 98A2 [KO:K09754] [EC:1.14.14.96]
            100500657  putative caffeoyl-CoA 3-O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100779260  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100811247  caffeoyl-CoA O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100780516  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            100792717  OMT5; anthocyanin 3'-O-methyltransferase [KO:K00588] [EC:2.1.1.104]
            100800911  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            100795229  probable caffeoyl-CoA O-methyltransferase At4g26220 [KO:K00588] [EC:2.1.1.104]
            100813350  flavonoid 3',5'-methyltransferase isoform X2 [KO:K00588] [EC:2.1.1.104]
            100305498  SOMT-9; O-methyltransferase SOMT-9 isoform 1 [KO:K00588] [EC:2.1.1.104]
            100799303  S-adenosyl-L-methionine-dependent methyltransferases superfamily protein [KO:K00588] [EC:2.1.1.104]
            100795858  caffeoyl-CoA O-methyltransferase 5 [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 gmx00940  Phenylpropanoid biosynthesis
            gmx00942  Anthocyanin biosynthesis
            gmx00943  Isoflavonoid biosynthesis
            gmx00944  Flavone and flavonol biosynthesis
KO_PATHWAY  ko00941
///
