Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays

Peter Spiteller; Erich Glawischnig; Alfons Gierl; Wolfgang Steglich

doi:10.1016/S0031-9422(01)00037-1

Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays

Peter Spiteller, Erich Glawischnig, Alfons Gierl, Wolfgang Steglich

Life Sciences

University of Munich

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

The ring expansion of 3-hydroxyindolin-2-one to 2-hydroxy-1,4-benzoxazin-3-one (HBOA) was investigated by labelling experiments. Action of the cytochrome P450 enzyme BX4 from maize on 3-hydroxyindolin-2-one under an ¹⁸O₂ atmosphere induced production of 2-hydroxy-1,4-benzoxazin-3-one in which the ring oxygen - but not the 2-hydroxy group of HBOA - is labelled. A mechanism for this transformation is proposed.

Original language	English
Pages (from-to)	373-376
Number of pages	4
Journal	Phytochemistry
Volume	57
Issue number	3
DOIs	https://doi.org/10.1016/S0031-9422(01)00037-1
State	Published - Jun 2001

Keywords

BX4
Biosynthesis
HBOA
Mono-oxygenase
P450
Ring expansion
Zea mays

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10.1016/S0031-9422(01)00037-1

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title = "Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays",

abstract = "The ring expansion of 3-hydroxyindolin-2-one to 2-hydroxy-1,4-benzoxazin-3-one (HBOA) was investigated by labelling experiments. Action of the cytochrome P450 enzyme BX4 from maize on 3-hydroxyindolin-2-one under an 18O2 atmosphere induced production of 2-hydroxy-1,4-benzoxazin-3-one in which the ring oxygen - but not the 2-hydroxy group of HBOA - is labelled. A mechanism for this transformation is proposed.",

keywords = "BX4, Biosynthesis, HBOA, Mono-oxygenase, P450, Ring expansion, Zea mays",

author = "Peter Spiteller and Erich Glawischnig and Alfons Gierl and Wolfgang Steglich",

note = "Funding Information: We thank Dr. Monika Frey, Garching, for suggestions and helpful discussions and Sebastian Gr{\"u}n for preparation of the induced yeast cell culture. This work was supported by SFB 369 of the Deutsche Forschungsgemein-schaft.",

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doi = "10.1016/S0031-9422(01)00037-1",

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AU - Spiteller, Peter

AU - Glawischnig, Erich

AU - Gierl, Alfons

AU - Steglich, Wolfgang

N1 - Funding Information: We thank Dr. Monika Frey, Garching, for suggestions and helpful discussions and Sebastian Grün for preparation of the induced yeast cell culture. This work was supported by SFB 369 of the Deutsche Forschungsgemein-schaft.

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N2 - The ring expansion of 3-hydroxyindolin-2-one to 2-hydroxy-1,4-benzoxazin-3-one (HBOA) was investigated by labelling experiments. Action of the cytochrome P450 enzyme BX4 from maize on 3-hydroxyindolin-2-one under an 18O2 atmosphere induced production of 2-hydroxy-1,4-benzoxazin-3-one in which the ring oxygen - but not the 2-hydroxy group of HBOA - is labelled. A mechanism for this transformation is proposed.

AB - The ring expansion of 3-hydroxyindolin-2-one to 2-hydroxy-1,4-benzoxazin-3-one (HBOA) was investigated by labelling experiments. Action of the cytochrome P450 enzyme BX4 from maize on 3-hydroxyindolin-2-one under an 18O2 atmosphere induced production of 2-hydroxy-1,4-benzoxazin-3-one in which the ring oxygen - but not the 2-hydroxy group of HBOA - is labelled. A mechanism for this transformation is proposed.

KW - BX4

KW - Biosynthesis

KW - HBOA

KW - Mono-oxygenase

KW - P450

KW - Ring expansion

KW - Zea mays

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SN - 0031-9422

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JO - Phytochemistry

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Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays

Abstract

Keywords

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