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Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti-Aging Derivatives
Feng, Lin-min; Ji, Shuai; Qiao, Xue; Li, Zi-wei; Lin, Xiong-hao; Ye, Min
关键词Alternaria alternate anti-aging biological activities biotransformations cycloastragenol Syncephalastrum racemosum
刊名ADVANCED SYNTHESIS & CATALYSIS
2015-05-26
DOI10.1002/adsc.201401158
357期:8页:1928-1940
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Applied ; Chemistry, Organic
资助者National Natural Science Foundation of China ; Chinese Ministry of Education ; National Natural Science Foundation of China ; Chinese Ministry of Education
研究领域[WOS]Chemistry
关键词[WOS]ASTRAGALUS-MEMBRANACEUS BUNGE ; BLAKESLEEANA NRRL 1369 ; MICROBIAL TRANSFORMATION ; CAENORHABDITIS-ELEGANS ; TRITERPENE GLYCOSIDES ; SUBSTRATE-SPECIFICITY ; CHEMICAL-CONSTITUENTS ; FILAMENTOUS FUNGI ; DFT CALCULATIONS ; LONGEVITY
英文摘要

Cycloastragenol is a cycloartane-type triterpenoid with significant telomerase-activating activities. In this paper, the biocatalysis of cycloastragenol by two strains of filamentous fungi, namely Syncephalastrum racemosum AS 3.264 and Alternaria alternata AS 3.4578, was investigated. Scaled-up biotransformation reactions yielded 27 metabolites. Their structures were established on the basis of extensive NMR and HR-ESI-MS data analyses, and 18 of them are new compounds. The two fungal strains exhibited distinct biocatalytic features. S. racemosum could catalyze ring expansion and epoxidation reactions to form 3 beta,10 beta-epoxy- or 6 alpha,19 alpha-epoxy-9,10-seco-cycloartane structures, whereas A. alternata preferred to catalyze acetylation reactions, especially at 3-OH, 6-OH and 19-OH. These regio- and stereoselective reactions are difficult to achieve by chemical means, but could be realized under mild conditions by biocatalysis. Furthermore, we found that some acetylated derivatives at 50 mu M could significantly extend the lifespan of Caenorhabditis elegans from 16.93 +/- 0.70 d of the control group to 20.01 +/- 0.75 d (P<0.01), versus 18.54 +/- 0.67 d for cycloastragenol. These biotransformed derivatives of cycloastragenol could be potential anti-aging agents.

语种英语
所属项目编号81222054 ; NCET-11-0019
资助者National Natural Science Foundation of China ; Chinese Ministry of Education ; National Natural Science Foundation of China ; Chinese Ministry of Education
WOS记录号WOS:000355235700032
引用统计
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/62282
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 100191, Peoples R China
推荐引用方式
GB/T 7714
Feng, Lin-min,Ji, Shuai,Qiao, Xue,et al. Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti-Aging Derivatives[J]. ADVANCED SYNTHESIS &amp; CATALYSIS,2015,357(8):1928-1940.
APA Feng, Lin-min,Ji, Shuai,Qiao, Xue,Li, Zi-wei,Lin, Xiong-hao,&Ye, Min.(2015).Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti-Aging Derivatives.ADVANCED SYNTHESIS & CATALYSIS,357(8),1928-1940.
MLA Feng, Lin-min,et al."Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti-Aging Derivatives".ADVANCED SYNTHESIS & CATALYSIS 357.8(2015):1928-1940.
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