Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona
Biotransformation of 2-Benzoxazolinone and 2-Hydroxy-1,4-Benzoxazin-3-one by Endophytic Fungi Isolated from Aphelandra tetragona
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DOI：
10.1128/aem.68.10.4863-4870.2002
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发表时间：
2002-10
影响因子：
4.4
通讯作者：
M. Zikmundová;K. Drandarov;Laurent Bigler;Manfred Hesse;C. Werner
中科院分区：
文献类型：
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作者：
M. Zikmundová;K. Drandarov;Laurent Bigler;Manfred Hesse;C. Werner
摘要研究了四种植物内生真菌对2-苯并恶唑啉酮（BOA）和2-羟基-1,4-苯并恶唑啉酮（HBOA）的生物转化。利用高效液相色谱-质谱联用技术，鉴定了几种新的酰化、氧化、还原、水解和硝化产物。镰刀菌将BOA和HBOA解毒为N-（2-羟基苯基）丙二胺酸。烟草Plectosporium tabacinum、Gliocladium cibotii和Chaetosphaeria sp将HBOA转化为2-羟基-N-（2-羟基苯基）乙酰胺、N-（2-羟基-5-硝基苯基）乙酰胺、N-（2-羟基-3-硝基苯基）乙酰胺、2-氨基- 3h -phenoxazin-3-one、2-（N-羟基）乙酰氨基- 3h -phenoxazin-3-one和2-（N-羟基）乙酰氨基- 3h -phenoxazin-3-one。3株真菌对BOA均无降解作用。利用2-羟基- n -（2-羟基苯基）[13C2]乙酰胺，研究表明，HBOA和BOA降解的代谢途径以邻氨基酚为关键中间体。
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-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.