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Substrate specificity for the 12 beta-hydroxylation of bufadienolides by Alternaria alternata
Ye, M; Guo, D
关键词Altemaria Alternata Biotransformation Bufadienolide Hydroxylation Substrate Specificity
刊名JOURNAL OF BIOTECHNOLOGY
2005-05-25
DOI10.1016/j.jbiotec.2005.02.002
117期:3页:253-262
收录类别SCI
文章类型Article
WOS标题词Science & Technology
类目[WOS]Biotechnology & Applied Microbiology
研究领域[WOS]Biotechnology & Applied Microbiology
关键词[WOS]LEUKEMIA-CELLS ; PSEUDOMONAS-AERUGINOSA ; CATHARANTHUS-ROSEUS ; CINOBUFAGIN ; BUFALIN ; BIOTRANSFORMATIONS ; RESIBUFOGENIN ; BIOCATALYSIS
英文摘要

Hydroxylation is an important route to synthesize more hydrophilic compounds of pharmaceutical significance. Microbial hydroxylation offers advantages over chemical means for its high specificity. In this study, a fungal strain Alternaria alternata AS 3.4578 was found to be able to catalyze the specific 12 beta-hydroxylation of a variety of cytotoxic bufadienolides. Cinobufagin and resibufogenin could be completely metabolized by A. alternata to generate their 12 beta-hydroxylated products in high yields (> 90%) within 8h of incubation. A. alternata could also convert 3-epi-desacetylcinobufagin into 3-epi-12 beta-hydroxyl desacetylcinobufagin as the major product (70% yield). C-3 dehydrogenated products were detected in these reactions in fair yields, while their accumulation was relatively slow. The 12p-hydroxylation of bufadienolides could be significantly inhibited by the substitution of 1 beta-, 5-, or 16 alpha-hydroxyl groups, and the 14 beta,15 beta-epoxy ring appeared to be a necessary structural requirement for the specificity. For the biotransformation of bufalin, a 14 beta-OH bufadienolide, this reaction was not specific, and accompanied by 7 beta-hydroxylation as a parallel and competing metabolic route. The biotransformation products were identified by comparison with authentic samples or tentatively characterized by high-performance liquid chromatography-diode array detection-atmospheric pressure chemical ionization-mass spectrometry analyses. (c) 2005 Elsevier B.V. All rights reserved.

语种英语
WOS记录号WOS:000229342100005
引用统计
被引频次:20[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/56900
专题北京大学药学院
作者单位Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
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Ye, M,Guo, D. Substrate specificity for the 12 beta-hydroxylation of bufadienolides by Alternaria alternata[J]. JOURNAL OF BIOTECHNOLOGY,2005,117(3):253-262.
APA Ye, M,&Guo, D.(2005).Substrate specificity for the 12 beta-hydroxylation of bufadienolides by Alternaria alternata.JOURNAL OF BIOTECHNOLOGY,117(3),253-262.
MLA Ye, M,et al."Substrate specificity for the 12 beta-hydroxylation of bufadienolides by Alternaria alternata".JOURNAL OF BIOTECHNOLOGY 117.3(2005):253-262.
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