Affiliation:
1. Organisch-chemisches Institut der Universität Zürich, CH-8057 Zürich, Switzerland
Abstract
ABSTRACT
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-3
H
-phenoxazin-3-one, 2-acetylamino-3
H
-phenoxazin-3-one, and 2-(
N
-hydroxy)acetylamino-3
H
-phenoxazin-3-one. BOA was not degraded by these three fungal isolates. Using 2-hydroxy-
N
-(2-hydroxyphenyl)[
13
C
2
]acetamide, it was shown that the metabolic pathway for HBOA and BOA degradation leads to
o
-aminophenol as a key intermediate.
Publisher
American Society for Microbiology
Subject
Ecology,Applied Microbiology and Biotechnology,Food Science,Biotechnology
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