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EC Tree
IUBMB Comments A cytochrome P-450 (heme-thiolate) protein purified from soybean.
The expected taxonomic range for this enzyme is: Glycine max
Synonyms
dimethylallyl-3,6a,9-trihydroxypterocarpan cyclase,
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dimethylallyl-3,6a,9-trihydroxypterocarpan cyclase
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2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2 = glyceollin II + [oxidized NADPH-hemoprotein reductase] + 2 H2O
2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2 = glyceollin III + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(2)
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4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2 = glyceollin I + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(3)
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2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2 = glyceollin II + [oxidized NADPH-hemoprotein reductase] + 2 H2O
a heme-thiolate protein, P-450, glyceollins II and III are formed from 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan whereas glyceollin I is formed from the 4-isomer
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2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2 = glyceollin II + [oxidized NADPH-hemoprotein reductase] + 2 H2O
(1)
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2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
A cytochrome P-450 (heme-thiolate) protein purified from soybean.
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2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + [reduced NADPH-hemoprotein reductase] + O2
glyceollin + [oxidized NADPH-hemoprotein reductase] + H2O
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enzyme catalyzes an NADPH-dependent and oxygen-dependent cyclization of a mixture of 2- and 4-dimethylallylglycinols to the glyceollin isomers I-III
glyceollin isomers I-III, glyceollin isomer I is formed from 4-dimethylallylglycinol and glyceollin isomers II and III from 2-dimethylallylglycinol
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glyceollin II + NADPH + H+ + H2O
2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan + NADP+ + O2
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r
additional information
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additional information
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last committed step in the glyceollin biosynthesis
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additional information
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not: NADH, enzyme does not catalyze the conversion of rot-2-enoic acid to deguelin in the presence or absence of NADPH
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additional information
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last committed step in the glyceollin biosynthesis
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cytochrome b
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average content of b-type cytochromes: 0.26 nmol/mg protein
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cytochrome P-450
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cytochrome P-450-dependent monooxygenase, average content of cytochrome P-450: 0.16 nmol/mg protein
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Ancymidol
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0.01 mM: 15% inhibition, 0.1 mM: 85% inhibition
BAS 110
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0.1 mM, 15% inhibition
BAS 111
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0.1 mM, 39% inhibition
CO
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inhibits in a white light-reversible manner in the presence of oxygen
cytochrome c
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0.01 mM: 25% inhibition, 0.025 mM: 64% inhibition, 0.05 mM: 85% inhibition
glyceollin
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product inhibition, 0.058 mM, 50% inhibition
ketoconazol
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0.01 mM: 34% inhibition, 0.1 mM: 100% inhibition
LAB 978
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0.01 mM: 17% inhibition, 0.1 mM: 49% inhibition
Metyrapone
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0.01 mM: 15% inhibition, 0.1 mM: 37% inhibition
NADP+
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strong inhibition by NADP+ at low NADPH concentrations
potassium isothiocyanate
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0.01 mM: 19% inhibition, 0.1 mM: 73% inhibition, 1 mM: 100% inhibition
SKF 525
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0.1 mM: 11% inhibition, 1 mM: 100% inhibition
tetcyclasis
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0.01 mM: 9% inhibition, 0.1 mM: 67% inhibition
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NADH
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a synergistic effect of NADH, 94% increase in cyclase activity, is observed at low NADPH concentrations of about 0.01 mM
additional information
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challenge with either a glucan elicitor from Phytophthora megasperma f.sp. glycinea or with yeast extract causes strong stimulation of cyclase activity with a maximum at about 24 h after elicitor addition
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0.002
2-(or 4-)dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan
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pH 7.5, 20°C, mixture of the two glyceollidin isomers
0.03
perrhenate
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pH 7.5, 20°C
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additional information
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7.5 - 9.5
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very broad pH-optimum
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7 - 9.5
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pH 7: 50% of maximum activity, no activity measurable above pH 9.5, probably because of the instability of the substrate
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cv. Harosoy 63
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brenda
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elicitor-challenged, unstimulated cell culture does not contain detectable cyclase activity
brenda
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the cyclase is associated with
brenda
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brenda
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Welle, R.; Grisebach, H.
Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers
Arch. Biochem. Biophys.
263
191-198
1988
Glycine max
brenda
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1.14.14.135 glyceollin synthase
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