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MetaCyc Pathway: glyceollin biosynthesis I
Inferred from experiment

Enzyme View:

Pathway diagram: glyceollin biosynthesis I

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisPhenylpropanoid Derivatives BiosynthesisFlavonoids BiosynthesisIsoflavonoids Biosynthesis
BiosynthesisSecondary Metabolites BiosynthesisPhytoalexins BiosynthesisIsoflavonoid Phytoalexins Biosynthesis

Some taxa known to possess this pathway include : Cicer arietinum, Glycine max, Glycyrrhiza echinata, Glycyrrhiza glabra, Medicago sativa, Phaseolus vulgaris

Expected Taxonomic Range: Fabaceae

Glyceollins are the main phytoalexins found in soybean (Glycine max). Consistent with most of the isoflavonoid derived phytoalexins, glyceollins are induced in response to plant pathogens [Boue00] [Hagmann84] and related stress [Landini03].

The initial enzymatic steps of the glyceollin biosynthesis parallel the biosynthesis of medicarpin and maackiain. In contrast to those simple pterocarpans the complex prenylated pterocarpans (phaseollin, glyceollin) also derive from the 5-deoxyisoflavone daidzein but do not involve a methoxylation step during their biosynthesis.

Glycinol, the final compound in this part of the glyceollin pathway, is stereospecifically hydroxylated at the 6a position resulting in the (-) or (6aS,11aS)-3,6a,9-configuration of this compound [Hagmann84]. The remaining enzymatic reactions maintain the given configuration as demonstrated for other pathways that involve a pterocarpan-6a-hydroxylase in their biosynthesis (e.g. pisatin) [Kochs89].

Superpathways: superpathway of pterocarpan biosynthesis (via daidzein)

Created 04-Feb-2005 by Foerster H, TAIR


Boue00: Boue SM, Carter CH, Ehrlich KC, Cleveland TE (2000). "Induction of the soybean phytoalexins coumestrol and glyceollin by Aspergillus." J Agric Food Chem 48(6);2167-72. PMID: 10888516

Hagmann84: Hagmann ML, Heller W, Grisebach H (1984). "Induction of phytoalexin synthesis in soybean. Stereospecific 3,9-dihydroxypterocarpan 6a-hydroxylase from elicitor-induced soybean cell cultures." Eur J Biochem 142(1);127-31. PMID: 6540173

Kochs89: Kochs G, Grisebach H (1989). "Phytoalexin synthesis in soybean: purification and reconstitution of cytochrome P450 3,9-dihydroxypterocarpan 6a-hydroxylase and separation from cytochrome P450 cinnamate 4-hydroxylase." Arch Biochem Biophys 273(2);543-53. PMID: 2505672

Landini03: Landini S, Graham MY, Graham TL (2003). "Lactofen induces isoflavone accumulation and glyceollin elicitation competency in soybean." Phytochemistry 62(6);865-74. PMID: 12590114

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Akashi98: Akashi T, Aoki T, Ayabe S (1998). "CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2'-hydroxylase." Biochem Biophys Res Commun 251(1);67-70. PMID: 9790908

Bless88: Bless W, Barz W, (1988) "Isolation of pterocarpan synthase, the terminal enzyme of pterocarpan phytoalexin biosynthesis in cell suspension cultures of Cicer arietinum." FEBS Letters (1988), 235(1), 47-50.

Clemens: Clemens S, Hinderer W, Wittkampg U, Barz W, (1993) "Characterization of cytochrome P450-dependent isoflavone hydroxylase from chickpea." Phytochemistry, 32(3), 653-657.

Dewick94: Dewick PM (1994). "Isoflavonoids." In: Harborne JB (editor) The flavonoids: Advances in research since 1986; Chapman and Hall, London , 117-238.

Ebel86: Ebel J, Grisebach H, Bonhoff A, Grab D, Hoffmann C, Kochs G, Mieth H, Schmidt W, Staeb M, (1986) "Phytoalexin synthesis in soybean following infection of roots with Phytophtora megasperma or treatment of cell cultures with fungal elicitors." In: Lugtenberg, B. (editor) Regocnition in microbe-plant symbiotic and pathogenic interactions (1986), NATO ASI series, series H: cell biology, Vol. 4, 345-361, Springer-Verlag Berlin Heidelberg New York London Paris Tokyo.

Fischer90: Fischer D, Ebenau-Jehle C, Grisebach H, (1990) "Purification and characterization of pterocarpan synthase from elicitor-challenged soybean cell cultures." Phytochemistry (1990), 29(9), 2879-2882.

Fischer90a: Fischer D, Ebenau-Jehle C, Grisebach H (1990). "Phytoalexin synthesis in soybean: purification and characterization of NADPH:2'-hydroxydaidzein oxidoreductase from elicitor-challenged soybean cell cultures." Arch Biochem Biophys 276(2);390-5. PMID: 2306102

Gunia: Gunia W, Hinderer W, Wittkampf U, Barz W, (1991) "Elicitor induction of cytochrome P-450 monooxygenases in cell suspension cultures of chickpea (Cicer arietinum L.) and their involvement in pterocarpan phytoalexin biosynthesis." Z. Naturforsch. 46c, 58-66.

Guo94: Guo L, Dixon RA, Paiva NL (1994). "The 'pterocarpan synthase' of alfalfa: association and co-induction of vestitone reductase and 7,2'-dihydroxy-4'-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis." FEBS Lett 356(2-3);221-5. PMID: 7805842

Guo94a: Guo L, Dixon RA, Paiva NL (1994). "Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2'-dihydroxy-4'-methoxyisoflavanol dehydratase." J Biol Chem 269(35);22372-8. PMID: 8071365

Hinderer: Hinderer W, Flentje U, Barz W, (1987) "Microsomal isoflavone 2'- and 3'-hydroxylases from chickpea (Cicer arietinum L.) cell suspensions induced for pterocarpan phytoalexin formation." FEBS Letters, 214(1), 101-106.

Kochs86: Kochs G, Grisebach H (1986). "Enzymic synthesis of isoflavones." Eur J Biochem 155(2);311-8. PMID: 3956488

Kochs92: Kochs G, Werck-Reichhart D, Grisebach H (1992). "Further characterization of cytochrome P450 involved in phytoalexin synthesis in soybean: cytochrome P450 cinnamate 4-hydroxylase and 3,9-dihydroxypterocarpan 6a-hydroxylase." Arch Biochem Biophys 293(1);187-94. PMID: 1731635

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Liu03a: Liu CJ, Huhman D, Sumner LW, Dixon RA (2003). "Regiospecific hydroxylation of isoflavones by cytochrome p450 81E enzymes from Medicago truncatula." Plant J 36(4);471-84. PMID: 14617078

Matthews87: Matthews DE, Weiner EJ, Matthews PS, VanEtten HD, (1987) "Role of oxygenases in pisatin biosynthesis and in the fungal degradation of maackiain." Plant Physiology (1987), 83, 365-370.

Paiva91: Paiva NL, Edwards R, Sun YJ, Hrazdina G, Dixon RA (1991). "Stress responses in alfalfa (Medicago sativa L.) 11. Molecular cloning and expression of alfalfa isoflavone reductase, a key enzyme of isoflavonoid phytoalexin biosynthesis." Plant Mol Biol 17(4);653-67. PMID: 1912490

Paiva94: Paiva NL, Sun Y, Dixon RA, VanEtten HD, Hrazdina G (1994). "Molecular cloning of isoflavone reductase from pea (Pisum sativum L.): evidence for a 3R-isoflavanone intermediate in (+)-pisatin biosynthesis." Arch Biochem Biophys 312(2);501-10. PMID: 8037464

Schopfer98: Schopfer CR, Kochs G, Lottspeich F, Ebel J (1998). "Molecular characterization and functional expression of dihydroxypterocarpan 6a-hydroxylase, an enzyme specific for pterocarpanoid phytoalexin biosynthesis in soybean (Glycine max L.)." FEBS Lett 432(3);182-6. PMID: 9720921

Tiemann91: Tiemann K, Inze D, Van Montagu M, Barz W (1991). "Pterocarpan phytoalexin biosynthesis in elicitor-challenged chickpea (Cicer arietinum L.) cell cultures. Purification, characterization and cDNA cloning of NADPH:isoflavone oxidoreductase." Eur J Biochem 200(3);751-7. PMID: 1915347

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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