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

Authors
Spiteller, P Glawischnig, E Gierl, A Steglich, W
Citation
P. Spiteller et al., Studies on the biosynthesis of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) from 3-hydroxyindolin-2-one in Zea mays, PHYTOCHEM, 57(3), 2001, pp. 373-376
Citations number
11
Categorie Soggetti
Agricultural Chemistry","Animal & Plant Sciences
Journal title
PHYTOCHEMISTRY
ISSN journal
00319422 → ACNP
Volume
57
Issue
3
Year of publication
2001
Pages
373 - 376
Database
ISI
SICI code
0031-9422(200106)57:3<373:SOTBO2>2.0.ZU;2-C
Abstract
The ring expansion of 3-hydroxyindolin-2-one to 2-hydroxy-l,4-benzoxazin-3- one (HBOA) was investigated by labelling experiments. Action of the cytochr ome P450 enzyme BX4 from maize on 3-hydroxyindolin-2-onc under an O-18(2) a tmosphere 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 mechani sm fur this transformation is proposed, (C) 2001 Elsevier Science Ltd. All rights reserved.