Information on EC 1.14.14.88 - isoflavone 3'-hydroxylase

-

689509, 693416

isoflavone 3'-hydroxylase

-

Biosynthesis of secondary metabolites, Isoflavonoid biosynthesis

isoflavone 3'-monooxygenase

-

MtCYP81E9

-

Mtl3'H

-

formononetin + [reduced NADPH-hemoprotein reductase] + O2 = calycosin + [oxidized NADPH-hemoprotein reductase] + H2O

-

hydroxylation

-

oxidation

-

redox reaction

-

reduction

-

KEGG

MetaCyc

(-)-maackiain biosynthesis, isoflavonoid biosynthesis II, rot-2'-enonate biosynthesis

formononetin,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)

A cytochrome P-450 (heme-thiolate) protein. Also acts on biochanin A and other isoflavones with a 4'-methoxy group. Involved in the biosynthesis of the pterocarpin phytoalexins medicarpin and maackiain.

110183-50-1

-

2'-hydroxyformononetin + [reduced NADPH-hemoprotein reductase] + O2

2',3'-dihydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O

-

Substrates: 39% of activity with biochanin A
Products: -

?

biochanin A + [reduced NADPH-hemoprotein reductase] + O2

?

-

Substrates: -
Products: -

?

biochanin A + [reduced NADPH-hemoprotein reductase] + O2

pratensein + [oxidized NADPH-hemoprotein reductase] + H2O

-

285318, 285319, 285320

Substrates: -
Products: -

ir

formononetin + [reduced NADPH-hemoprotein reductase] + O2

3'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O

formononetin + [reduced NADPH-hemoprotein reductase] + O2

calycosin + [oxidized NADPH-hemoprotein reductase] + H2O

4 entries

genistein + NADPH + O2

?

-

Substrates: 19% of activity with biochanin A
Products: -

?

additional information

?

-

formononetin + [reduced NADPH-hemoprotein reductase] + O2

3'-hydroxyformononetin + [oxidized NADPH-hemoprotein reductase] + H2O

-

285318, 285320

Substrates: involved in the biosynthesis of the pterocarpin phytoalexin maackiain, cytochrome P450-dependent monooxygenase
Products: -

ir

formononetin + [reduced NADPH-hemoprotein reductase] + O2

calycosin + [oxidized NADPH-hemoprotein reductase] + H2O

additional information

-

no cofactors are FAD and FMN

-

BAS110

-

285320

CO

-

ratio CO:O2 of 9:1 leads to 88-96% inhibition

285320

cytochrome c

-

0.01 mM reduces activity to 4%, 0.1 mM reduces activity to 1%

juglone

-

0.001 mM juglone reduces activity to 50%

ketoconazol

-

tetcyclasis

-

Triadimefone

-

additional information

-

no inhibition by 5 mM KCN and 1 mM EDTA

-

NADH

-

synergistic effect with NADPH, 150% of NADPH activity

additional information

-

cells susceptible to Ascochyta rabiei can be elicitor-induced to 500% activity

-

0.11 - 12.5

Biochanin A

0.05 - 11

formononetin

0.1

Biochanin A

-

pH 8.0, 2 mM NADPH

0.028

formononetin

-

pH 8.0, 2 mM NADPH

additional information

calycosin concentration in different tissues, overview

7.5

-

assay conditions

8

-

8

-

25

-

assay conditions

285319

30

-

285320

var. mongholicus

UniProt

-

-

cell suspension culture

-

-

stem

-

additional information

calycosin concentration in different tissues, quantitative enzyme expression analysis, overview

endoplasmic reticulum membrane

-

-

Highest Expressing Human Cell Lines

Filter by:

Cell Line Links

Gene Links

physiological function

calycosin-7-O-beta-D-glucoside pathway, calycosin and calycosin-7-O-beta-D-glucoside accumulate in whole plants, mainly leaves, in response to low temperature

-20°C, 100 mM potassium phosphate, pH 7.5 containing 400 mM sucrose and 3.5 mM 2-mercaptoethanol, 24 h

-

DNA and amino acid sequence determination and analysis, quantitative tissue-dependent expression analysis, overview

PCR-amplification

gradual increase (1.8fold) of enzyme expression after low-temperature treatment (4 h 2°C) of plants adapted to 16°C, dramatic increase of expression in warm-treatment plants (16°C to 25°C or from 2°C to 25°C), maximum at h 4 during treatment, higher levels than at low-temperature induction, cold-induced mRNA accumulation is light dependent

medicine

Astragalus membranaceus var. mongholicus is a medicinal plant in traditional Chinese medicine, the enzyme products calycosin and calycosin-7-O-beta-D-glucoside are two major isoflavones related to the bioactivity of the herb