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学科主题: 药学
题名:
Biocatalysis of Cycloastragenol by Filamentous Fungi to Produce Unexpected Triterpenes
作者: Yang, Wen-zhi; Ye, Min; Huang, Fei-xia; He, Wen-ni; Guo, De-an
关键词: biocatalysis ; cycloastragenol ; filamentous fungi ; ring expansion ; tetracyclic triterpenoids
刊名: ADVANCED SYNTHESIS & CATALYSIS
发表日期: 2012-02-01
DOI: 10.1002/adsc.201100511
卷: 354, 期:2-3, 页:527-539
收录类别: SCI ; IC
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Applied ; Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: ASTRAGALOSIDE-IV ; SAPONINS ; RADIX
英文摘要:

The biocatalysis of cycloastragenol, a natural tetracyclic triterpenoid with anti-aging activity, by cultured whole cells of three strains of filamentous fungi, namely Cunninghamella elegans AS 3.1207, Syncephalastrum racemosum AS 3.264 and Doratomyces stemonitis AS 3.1411 produced 15 metabolites. Thirteen of them are new compounds. The structures of these metabolites were fully characterized on the basis of HR-ESI-MS analyses together with 1D and 2D NMR spectroscopy. The three fungal strains exhibited significant biocatalytic preferences: C. elegans enabled hydroxylation reactions, particularly on the 28- and 29-CH3 groups; S. racemosum efficiently catalyzed a complicated rearrangement reaction to form the unusual ranunculane skeleton, which was further substituted with diverse side chains at C-19; D. stemonitis mainly led to carbonylation reactions, especially on 3-OH. It is particularly noteworthy that S. racemosum also catalyzed an unexpected ring expansion reaction to generate the rare 9(10)a-homo-19-nor-cycloartane skeleton. Biocatalysis was proved powerful in the structural diversification of cycloastragenol for future structure-activity relationship studies.

语种: 英语
所属项目编号: 985-2-119-121 ; 7102103 ; 2009B02
项目资助者: Peking University Health Science Center ; Beijing Natural Science Foundation ; Beijing NOVA Program
WOS记录号: WOS:000300448400035
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/62325
Appears in Collections:北京大学药学院_期刊论文

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作者单位: Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China

Recommended Citation:
Yang, Wen-zhi,Ye, Min,Huang, Fei-xia,et al. Biocatalysis of Cycloastragenol by Filamentous Fungi to Produce Unexpected Triterpenes[J]. ADVANCED SYNTHESIS & CATALYSIS,2012,354(2-3):527-539.
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