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Cytochrome P450s in flavonoid metabolism

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Abstract

In this review, cytochrome P450s characterized at the molecular level catalyzing aromatic hydroxylations, aliphatic hydroxylations and skeleton formation in the flavonoid metabolism are surveyed. They are involved in the biosynthesis of anthocyanin pigments and condensed tannin (CYP75, flavonoid 3′,5′-hydroxylase and 3′-hydroxylase), flavones [CYP93B, (2S)-flavanone 2-hydroxylase and flavone synthase II], and leguminous isoflavonoid phytoalexins [CYP71D9, flavonoid 6-hydroxylase; CYP81E, isoflavone 2′-hydroxylase and 3′-hydroxylase; CYP93A, 3,9-dihydroxypterocarpan 6a-hydroxylase; CYP93C, 2-hydroxyisoflavanone synthase (IFS)]. Other P450s of the flavonoid metabolism include methylenedioxy bridge forming enzyme, cyclases producing glyceollins, flavonol 6-hydroxylase and 8-dimethylallylnaringenin 2′-hydroxylase. Mechanistic studies on the unusual aryl migration by CYP93C, regulation of IFS expression in plant organs and its biotechnological applications are introduced, and flavonoid metabolisms by non-plant P450s are also briefly discussed.

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Abbreviations

2-ODD:

2-oxoacid-dependent oxidase

C4H:

cinnamate 4-hydroxylase

CHI:

chalcone isomerase

CHS:

chalcone synthase

D6aH:

3,9-dihydroxypterocarpan 6a-hydroxylase

F2H:

(2S)-flavanone 2-hydroxylase

F3′H:

flavonoid 3′-hydroxylase

F3′5′H:

flavonoid 3′,5′-hydroxylase

FNS:

flavone synthase

I2′H:

isoflavone 2′-hydroxylase

I3′H:

isoflavone 3′-hydroxylase

IFS:

2-hydroxyisoflavanone synthase

PKR:

chalcone polyketide reductase

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Acknowledgments

We thank useful discussions by Drs. Toshio Aoki and Norimoto Shimada of Nihon University and Dr. Yuji Sawada of RIKEN Plant Science Center.

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  1. Department of Applied Biological Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa, 252-8510, Japan

    Shin-ichi Ayabe & Tomoyoshi Akashi

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Correspondence to Shin-ichi Ayabe.

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Ayabe, Si., Akashi, T. Cytochrome P450s in flavonoid metabolism. Phytochem Rev 5, 271–282 (2006). https://doi.org/10.1007/s11101-006-9007-3

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