ENTRY       gmx00943                    Pathway
NAME        Isoflavonoid biosynthesis - Glycine max (soybean)
DESCRIPTION Isoflavonoids are biologically active compounds, such as phytoestrogens, produced by pea family plants. While flavonoids (in the narrow sense) have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3-phenylchromen-4-one backbone with no hydroxyl group substitution at position 2. Isoflavonoids are derived from the flavonoid biosynthesis pathway via liquiritigenin or naringenin.
CLASS       Metabolism; Biosynthesis of other secondary metabolites
PATHWAY_MAP gmx00943  Isoflavonoid biosynthesis
MODULE      gmx_M00941  Isoflavone biosynthesis, liquiritigenin/naringenin => daidzein/genistein [PATH:gmx00943]
            gmx_M00942  Pterocarpan biosynthesis, daidzein => medicarpin [PATH:gmx00943]
DBLINKS     GO: 0009717
ORGANISM    Glycine max (soybean) [GN:gmx]
GENE        606705  IFS2; 2-hydroxyisoflavanone synthase precursor [KO:K13257] [EC:1.14.14.87]
            100037450  IFS1; isoflavone synthase 1 precursor [KO:K13257] [EC:1.14.14.87]
            547489  HIDH; 2-hydroxyisoflavanone dehydratase [KO:K13258] [EC:4.2.1.105]
            100785409  2-hydroxyisoflavanone dehydratase [KO:K13258] [EC:4.2.1.105]
            100807589  IOMT1; isoflavone 4'-O-methyltransferase [KO:K13259] [EC:2.1.1.212 2.1.1.46]
            106795493  IOMT2; isoflavone 4'-O-methyltransferase [KO:K13259] [EC:2.1.1.212 2.1.1.46]
            100784120  isoflavone 3'-hydroxylase [KO:K22932] [EC:1.14.14.88]
            100784650  isoflavone 2'-hydroxylase [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100811727  cytochrome P450 81E8 [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100790507  isoflavone 2'-hydroxylase [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100804509  cytochrome P450 81E8 [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100798269  isoflavone 2'-hydroxylase [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100797371  isoflavone 2'-hydroxylase [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100812102  I2'H; isoflavone 2'-hydroxylase [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100807819  isoflavone 2'-hydroxylase [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100801092  CYP81E11; isoflavone 2'-hydroxylase-like [KO:K13260] [EC:1.14.14.90 1.14.14.89]
            100776878  CYP93A1; 3,9-dihydroxypterocarpan 6A-monooxygenase [KO:K13261] [EC:1.14.14.93]
            100808223  3,9-dihydroxypterocarpan 6A-monooxygenase [KO:K13261] [EC:1.14.14.93]
            100813225  isoflavone 7-O-methyltransferase-like [KO:K13262] [EC:2.1.1.150]
            100800021  isoflavone-7-O-methyltransferase 6 [KO:K13262] [EC:2.1.1.150]
            100818724  isoflavone-7-O-methyltransferase 9 [KO:K13262] [EC:2.1.1.150]
            100819257  isoflavone 7-O-methyltransferase [KO:K13262] [EC:2.1.1.150]
            100811609  isoflavone 7-O-methyltransferase [KO:K13262] [EC:2.1.1.150]
            100779638  isoflavone 7-O-methyltransferase [KO:K13262] [EC:2.1.1.150]
            100776336  isoflavone 7-O-methyltransferase [KO:K13262] [EC:2.1.1.150]
            100819853  isoflavone-7-O-methyltransferase 6-like [KO:K13262] [EC:2.1.1.150]
            100812688  uncharacterized protein LOC100812688 [KO:K13262] [EC:2.1.1.150]
            100819796  isoflavone 7-O-methyltransferase [KO:K13262] [EC:2.1.1.150]
            100818947  isoflavone-7-O-methyltransferase 6 [KO:K13262] [EC:2.1.1.150]
            100791825  isoflavone-7-O-methyltransferase 6 [KO:K13262] [EC:2.1.1.150]
            100800912  isoflavone-7-O-methyltransferase 6 [KO:K13262] [EC:2.1.1.150]
            100819957  LOW QUALITY PROTEIN: isoflavone 7-O-methyltransferase [KO:K13262] [EC:2.1.1.150]
            100101902  IF7GT; isoflavone 7-O-glucosyltransferase 1 [KO:K13263] [EC:2.4.1.170]
            100777343  UGT7; isoflavone 7-O-glucosyltransferase UGT7 [KO:K13263] [EC:2.4.1.170]
            100776806  UGT8; isoflavone 7-O-glucosyltransferase UGT8 [KO:K13263] [EC:2.4.1.170]
            100127426  IF7MaT; malonyl-CoA:isoflavone 7-O-glucoside-6''-O-malonyltransferase [KO:K13264] [EC:2.3.1.115]
            100127365  AT133; malonyl-CoA:isoflavone 7-O-glucoside-6''-O-malonyltransferase [KO:K13264] [EC:2.3.1.115]
            100781863  NmrA-like family domain-containing protein [KO:K05281] [EC:1.3.1.45]
            100778149  isoflavone reductase-like [KO:K05281] [EC:1.3.1.45]
            547659  NADPH:isoflavone reductase [KO:K05281] [EC:1.3.1.45]
            100781316  IFR; isoflavone reductase [KO:K05281] [EC:1.3.1.45]
            100194416  vestitone reductase [KO:K13265] [EC:1.1.1.348]
            100794209  uncharacterized protein LOC100794209 [KO:K13265] [EC:1.1.1.348]
            100793687  uncharacterized protein LOC100793687 [KO:K13265] [EC:1.1.1.348]
            547660  2'-hydroxydihydrodaidzein reductase [KO:K13265] [EC:1.1.1.348]
            100500621  PTS1; pterocarpan synthase 1 precursor [KO:K25075] [EC:4.2.1.139]
            100817155  PTS3; pterocarpan synthase precursor [KO:K25075] [EC:4.2.1.139]
            100817686  PTS4; pterocarpan synthase precursor [KO:K25075] [EC:4.2.1.139]
            100814284  F6H1; flavonoid 6-hydroxylase [KO:K13267] [EC:1.14.13.-]
            100813216  F6H2; cytochrome P450 71D9-like [KO:K13267] [EC:1.14.13.-]
            100808331  F6H3; LOW QUALITY PROTEIN: cytochrome P450 71D9-like [KO:K13267] [EC:1.14.13.-]
            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]
COMPOUND    C00509  Naringenin
            C00786  (-)-Vestitone
            C00814  Biochanin A
            C00858  Formononetin
            C01263  3,6,9-Trihydroxypterocarpan
            C01477  Apigenin
            C01562  Calycosin
            C01701  (-)-Glyceollin I
            C02495  2'-Hydroxydaidzein
            C02675  Dihydrobiochanin A
            C02920  2'-Hydroxyformononetin
            C03567  2'-Hydroxydihydrodaidzein
            C04271  3,9-Dihydroxypterocarpan
            C05376  Biochanin A-beta-D-glucoside
            C06563  Genistein
            C07593  Rotenone
            C09126  Genistin
            C09762  Liquiritigenin
            C10200  Anhydroglycinol
            C10205  Coumestrol
            C10208  Daidzein
            C10216  Daidzin
            C10422  (-)-Glyceollin II
            C10502  (-)-Maackiain
            C10503  Medicarpin
            C10509  Ononin
            C10516  Pisatin
            C10520  Pratensein
            C10521  Prunetin
            C10522  Pseudobaptigenin
            C10538  Trifolirhizin
            C12123  7,4'-Dihydroxyflavone
            C12125  Isoformononetin
            C12134  2'-Hydroxygenistein
            C12135  2'-Hydroxybiochanin A
            C12625  Biochanin A 7-O-(6-O-malonyl-beta-D-glucoside)
            C12631  2-Hydroxy-2,3-dihydrogenistein
            C14314  4',6,7-Trihydroxyisoflavone
            C14536  Glycitein
            C15509  Glyceocarpin
            C15510  4-Glyceollidin
            C15511  Glyceollin III
            C15567  2,7,4'-Trihydroxyisoflavanone
            C16187  7,2'-Dihydroxy-4'-methoxy-isoflavanol
            C16188  7-Hydroxy-2',4',5'-trimethoxyisoflavone
            C16189  9-Demethylmunduserone
            C16190  2,7-Dihydroxy-4'-methoxyisoflavanone
            C16191  Malonyldaidzin
            C16192  Malonylgenistin
            C16195  Glycitin
            C16197  Malonylglycitin
            C16222  Formononetin 7-O-(6-O-malonyl-beta-D-glucoside)
            C16223  (-)-Medicocarpin
            C16224  Medicarpin 3-O-glucoside-6'-malonate
            C16225  (-)-Vestitol
            C16226  2',7-Dihydroxy-4',5'-methylenedioxyisoflavone
            C16227  (+)-Sophorol
            C16228  (-)-Sophorol
            C16229  (+)-Maackiain
            C16230  (+)-6a-Hydroxymaackiain
            C16231  (-)-Maackiain-3-O-glucosyl-6''-O-malonate
            C16232  6,7,4'-Trihydroxyflavanone
            C16233  2,6,7,4'-Tetrahydroxyisoflavanone
            C19727  5-Hydroxypseudobaptigenin
REFERENCE   PMID:11027686
  AUTHORS   Latunde-Dada AO, Cabello-Hurtado F, Czittrich N, Didierjean L, Schopfer C, Hertkorn N, Werck-Reichhart D, Ebel J.
  TITLE     Flavonoid 6-hydroxylase from soybean (Glycine max L.), a novel plant P-450 monooxygenase.
  JOURNAL   J Biol Chem 276:1688-95 (2001)
            DOI:10.1074/jbc.M006277200
REFERENCE   PMID:12179983
  AUTHORS   Baggett BR, Cooper JD, Hogan ET, Carper J, Paiva NL, Smith JT.
  TITLE     Profiling isoflavonoids found in legume root extracts using capillary electrophoresis.
  JOURNAL   Electrophoresis 23:1642-51 (2002)
            DOI:10.1002/1522-2683(200206)23:11<1642::AID-ELPS1642>3.0.CO;2-Y
REFERENCE   PMID:16996502
  AUTHORS   Akashi T, Koshimizu S, Aoki T, Ayabe S.
  TITLE     Identification of cDNAs encoding pterocarpan reductase involved in isoflavan phytoalexin biosynthesis in Lotus japonicus by EST mining.
  JOURNAL   FEBS Lett 580:5666-70 (2006)
            DOI:10.1016/j.febslet.2006.09.016
REFERENCE   PMID:14617078
  AUTHORS   Liu CJ, Huhman D, Sumner LW, Dixon RA.
  TITLE     Regiospecific hydroxylation of isoflavones by cytochrome p450 81E enzymes from Medicago truncatula.
  JOURNAL   Plant J 36:471-84 (2003)
            DOI:10.1046/j.1365-313X.2003.01893.x
REFERENCE   PMID:15082922
  AUTHORS   Dhaubhadel S, McGarvey BD, Williams R, Gijzen M.
  TITLE     Isoflavonoid biosynthesis and accumulation in developing soybean seeds.
  JOURNAL   Plant Mol Biol 53:733-43 (2003)
            DOI:10.1023/B:PLAN.0000023666.30358.ae
REFERENCE   PMID:11164575
  AUTHORS   Shimada N, Akashi T, Aoki T, Ayabe S.
  TITLE     Induction of isoflavonoid pathway in the model legume Lotus japonicus: molecular characterization of enzymes involved in phytoalexin biosynthesis.
  JOURNAL   Plant Sci 160:37-47 (2000)
            DOI:10.1016/S0168-9452(00)00355-1
REFERENCE   PMID:16667851
  AUTHORS   Preisig CL, Bell JN, Sun Y, Hrazdina G, Matthews DE, Vanetten HD
  TITLE     Biosynthesis of the Phytoalexin Pisatin : Isoflavone Reduction and Further Metabolism of the Product Sophorol by Extracts of Pisum sativum.
  JOURNAL   Plant Physiol 94:1444-8 (1990)
            DOI:10.1104/pp.94.3.1444
REFERENCE   PMID:17452423
  AUTHORS   Shimada N, Sato S, Akashi T, Nakamura Y, Tabata S, Ayabe S, Aoki T
  TITLE     Genome-wide analyses of the structural gene families involved in the legume-specific 5-deoxyisoflavonoid biosynthesis of Lotus japonicus.
  JOURNAL   DNA Res 14:25-36 (2007)
            DOI:10.1093/dnares/dsm004
REFERENCE   PMID:16924535
  AUTHORS   Lozovaya VV, Lygin AV, Zernova OV, Ulanov AV, Li S, Hartman GL, Widholm JM.
  TITLE     Modification of phenolic metabolism in soybean hairy roots through down regulation of chalcone synthase or isoflavone synthase.
  JOURNAL   Planta 225:665-79 (2007)
            DOI:10.1007/s00425-006-0368-z
REFERENCE   PMID:12207646
  AUTHORS   Sawada Y, Kinoshita K, Akashi T, Aoki T, Ayabe S.
  TITLE     Key amino acid residues required for aryl migration catalysed by the cytochrome P450 2-hydroxyisoflavanone synthase.
  JOURNAL   Plant J 31:555-64 (2002)
            DOI:10.1046/j.1365-313X.2002.01378.x
REFERENCE   PMID:16006598
  AUTHORS   Deavours BE, Dixon RA
  TITLE     Metabolic engineering of isoflavonoid biosynthesis in alfalfa.
  JOURNAL   Plant Physiol 138:2245-59 (2005)
            DOI:10.1104/pp.105.062539
REFERENCE   
  AUTHORS   Hinderer W, Flentje U, Barz W.
  TITLE     Microsomal isoflavone 2'- and 3'-hydroxylases from chickpea (Cicer arietinum L.) cell suspensions induced for pterocarpan phytoalexin formation.
  JOURNAL   FEBS Lett 214:101-106 (1987)
            DOI:10.1016/0014-5793(87)80021-2
REFERENCE   
  AUTHORS   Aoki T, Akashi T, Ayabe S.
  TITLE     Flavonoids of leguminous plants: structure, biological activity, and biosynthesis.
  JOURNAL   J Plant Res 113:475-488 (2000)
            DOI:10.1007/PL00013958
REFERENCE   
  AUTHORS   Barz W, Mackenbrock U.
  TITLE     Constitutive and elicitation induced metabolism of isoflavones and pterocarpans in chickpea (Cicer arietinum) cell suspension cultures.
  JOURNAL   Plant Cell Tissue Organ Cult 38:199-211 (1994)
            DOI:10.1007/BF00033878
REFERENCE   
  AUTHORS   Fischer D, Ebenau-Jehle C, Grisebach H.
  TITLE     Purification and characterization of pterocarpan synthase from elicitor-challenged soybean cell cultures.
  JOURNAL   Phytochemistry 29:2879-2882 (1990)
            DOI:10.1016/0031-9422(90)87096-D
REFERENCE   
  AUTHORS   Ayabe S, Akashi T.
  TITLE     Cytochrome P450s in flavonoid metabolism.
  JOURNAL   Phytochem Rev 5:271-282 (2006)
            DOI:10.1007/s11101-006-9007-3
REFERENCE   PMID:24197106
  AUTHORS   Daniel S, Tiemann K, Wittkampf U, Bless W, Hinderer W, Barz W
  TITLE     Elicitor-induced metabolic changes in cell cultures of chickpea (Cicer arietinum L.) cultivars resistant and susceptible to Ascochyta rabiei : I. Investigations of enzyme activities involved in isoflavone and pterocarpan phytoalexin biosynthesis.
  JOURNAL   Planta 182:270-8 (1990)
            DOI:10.1007/BF00197121
REL_PATHWAY gmx00941  Flavonoid biosynthesis
KO_PATHWAY  ko00943
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