KEGG   PATHWAY: rn00943
Entry
rn00943                     Pathway                                
Name
Isoflavonoid biosynthesis
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
rn00943  Isoflavonoid biosynthesis
rn00943

Module
M00941  Isoflavone biosynthesis, liquiritigenin/naringenin => daidzein/genistein [PATH:rn00943]
M00942  Pterocarpan biosynthesis, daidzein => medicarpin [PATH:rn00943]
Other DBs
GO: 0009717
Reaction
R02445  flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R02931  S-adenosyl-L-methionine: genistein 4'-O-methyltransferase
R02932  UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
R02954  dihydrobiochanin-A:NADP+ delta2-oxidoreductase
R03006  formononetin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R03452  (6aR,11aR)-3,9-dihydroxypterocarpan,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (6a-hydroxylating)
R03962  2'-hydroxy-2,3-dihydrodaidzein:NADP+ 2-oxidoreductase
R06560  formononetin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
R06561  biochanin A,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
R06562  vestitone:NADP+ oxidoreductase
R06564  S-adenosyl-L-methionine:daidzein 4'-O-methyltransferase
R06606  daidzein,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
R06607  genistein,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
R06793  2-hydroxy-2,3-dihydrogenistein hydro-lyase (genistein-forming)
R06794  S-adenosyl-L-methionine:hydroxyisoflavone 7-O-methyltransferase
R06795  UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
R06796  malonyl-CoA:isoflavone-7-O-beta-D-glucoside 6''-O-malonyltransferase
R07195  2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
R07196  2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
R07197  4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
R07271  dimethylallyl-diphosphate:(6aS,11aS)-3,6a,9-trihydroxypterocarpan dimethylallyltransferase
R07272  dimethylallyl-diphosphate:(6aS,11aS)-3,6a,9-trihydroxypterocarpan dimethylallyltransferase
R07317  2,7,4'-trihydroxyisoflavanone hydro-lyase (daidzein-forming)
R07711  
R07712  flavanone,2-oxoglutarate:oxygen oxidoreductase (dehydrating)
R07715  6,7,4'-trihydroxyflavanone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
R07716  
R07717  
R07718  UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
R07719  malonyl-CoA:isoflavone-7-O-beta-D-glucoside 6''-O-malonyltransferase
R07720  UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
R07721  malonyl-CoA:isoflavone-7-O-beta-D-glucoside 6''-O-malonyltransferase
R07722  S-adenosyl-L-methionine:isoflavone 4'-O-methyltransferase
R07723  2,7-dihydroxy-4'-methoxyisoflavanone hydro-lyase (formononetin-forming)
R07724  S-adenosyl-L-methionine:hydroxyisoflavone 7-O-methyltransferase
R07725  
R07726  
R07728  (6aR,11aR)-3,9-dihydroxypterocarpan:NADP+ 2'-oxidoreductase
R07729  UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
R07731  malonyl-CoA:isoflavone-7-O-beta-D-glucoside 6''-O-malonyltransferase
R07732  
R07733  
R07735  
R07736  
R07737  (3R,4R)-4'-methoxyisoflavan-2',4,7-triol:NADP+ 4-oxidoreductase
R07738  4'-methoxyisoflavan-2',4,7-triol hydro-lyase [(-)-medicarpin-forming]
R07739  
R07740  UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
R07741  malonyl-CoA:pterocarpan-7-O-beta-D-glucoside 6''-O-malonyltransferase
R07742  
R07743  
R07744  
R07745  calycosin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)
R07746  pseudobaptigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2'-hydroxylating)
R07747  (+)-sophorol:NADP+ oxidoreductase
R07748  (+)-maackiain:NADP+ 2'-oxidoreductase
R07749  
R07750  S-adenosyl-L-methionine:(+)-6a-hydroxymaackiain 3-O-methyltransferase
R07751  (-)-sophorol:NADP+ oxidoreductase
R07752  (-)-maackiain:NADP+ 2'-oxidoreductase
R07753  UDP-glucose:isoflavone 7-O-beta-D-glucosyltransferase
R07754  malonyl-CoA:pterocarpan-7-O-beta-D-glucoside 6''-O-malonyltransferase
R07755  
R07756  
R07757  malonyl-CoA:isoflavone-7-O-beta-D-glucoside 6''-O-malonyltransferase
R07776  biochanin A,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
R07777  liquiritigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
R07778  naringenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
R09602  pratensein,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (methylenedioxy-bridge-forming)
R12277  liquiritigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (7,4'-dihydroxyflavone-forming)
R12278  naringenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (apigenin-forming)
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
Related
pathway
rn00941  Flavonoid biosynthesis
KO pathway
ko00943   

DBGET integrated database retrieval system