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学科主题: 药学
题名:
Substrate specificity for the 12 beta-hydroxylation of bufadienolides by Alternaria alternata
作者: Ye, M; Guo, D
关键词: Altemaria alternata ; biotransformation ; bufadienolide ; hydroxylation ; substrate specificity
刊名: JOURNAL OF BIOTECHNOLOGY
发表日期: 2005-05-25
DOI: 10.1016/j.jbiotec.2005.02.002
卷: 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
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/56900
Appears in Collections:北京大学药学院_期刊论文

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作者单位: Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China

Recommended Citation:
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.
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