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Biocatalysis of Cycloastragenol by Filamentous Fungi to Produce Unexpected Triterpenes
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
2012-02-01
DOI10.1002/adsc.201100511
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
WOS记录号WOS:000300448400035
引用统计
被引频次:16[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/400002259/62325
专题北京大学药学院
北京大学药学院_天然药物学系
作者单位Peking Univ, State Key Lab Nat & Biomimet Drugs, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
推荐引用方式
GB/T 7714
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.
APA Yang, Wen-zhi,Ye, Min,Huang, Fei-xia,He, Wen-ni,&Guo, De-an.(2012).Biocatalysis of Cycloastragenol by Filamentous Fungi to Produce Unexpected Triterpenes.ADVANCED SYNTHESIS & CATALYSIS,354(2-3),527-539.
MLA Yang, Wen-zhi,et al."Biocatalysis of Cycloastragenol by Filamentous Fungi to Produce Unexpected Triterpenes".ADVANCED SYNTHESIS & CATALYSIS 354.2-3(2012):527-539.
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