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Applied and Environmental Microbiology, October 2002, p. 4863-4870, Vol. 68, No. 10
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.10.4863-4870.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.

Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona

M. Zikmundová, K. Drandarov, L. Bigler, M. Hesse, and C. Werner*

Organisch-chemisches Institut der Universität Zürich, CH-8057 Zürich, Switzerland

Received 8 May 2002/ Accepted 22 July 2002

The biotransformation of the phytoanticipins 2-benzoxazolinone (BOA) and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) by four endophytic fungi isolated from Aphelandra tetragona was studied. Using high-performance liquid chromatography-mass spectrometry, several new products of acylation, oxidation, reduction, hydrolysis, and nitration were identified. Fusarium sambucinum detoxified BOA and HBOA to N-(2-hydroxyphenyl)malonamic acid. Plectosporium tabacinum, Gliocladium cibotii, and Chaetosphaeria sp. transformed HBOA to 2-hydroxy-N-(2-hydroxyphenyl)acetamide, N-(2-hydroxyphenyl)acetamide, N-(2-hydroxy-5-nitrophenyl)acetamide, N-(2-hydroxy-3-nitrophenyl)acetamide, 2-amino-3H-phenoxazin-3-one, 2-acetylamino-3H-phenoxazin-3-one, and 2-(N-hydroxy)acetylamino-3H-phenoxazin-3-one. BOA was not degraded by these three fungal isolates. Using 2-hydroxy-N-(2-hydroxyphenyl)[13C2]acetamide, it was shown that the metabolic pathway for HBOA and BOA degradation leads to o-aminophenol as a key intermediate.

* Corresponding author. Mailing address: Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland. Phone: 41-1-6354292. Fax: 41-1-6356812. E-mail: cwerner{at}oci.unizh.ch.

Applied and Environmental Microbiology, October 2002, p. 4863-4870, Vol. 68, No. 10
0099-2240/02/$04.00+0     DOI: 10.1128/AEM.68.10.4863-4870.2002
Copyright © 2002, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Glenn, A. E., Meredith, F. I., Morrison III, W. H., Bacon, C. W. (2003). Identification of Intermediate and Branch Metabolites Resulting from Biotransformation of 2-Benzoxazolinone by Fusarium verticillioides. Appl. Environ. Microbiol. 69: 3165-3169 [Abstract] [Full Text]  


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