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

Research output: Contribution to journalArticlepeer-review

15 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 languageEnglish
Pages (from-to)373-376
Number of pages4
JournalPhytochemistry
Volume57
Issue number3
DOIs
StatePublished - Jun 2001

Keywords

  • BX4
  • Biosynthesis
  • HBOA
  • Mono-oxygenase
  • P450
  • Ring expansion
  • Zea mays

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