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Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity
He, Wenni1; Liu, Miaomiao1; Li, Xiaolin2; Zhang, Xiaoping3; Abdel-Mageed, Wael M.4,5; Li, Li6,7; Wang, Wenzhao8; Zhang, Jingyu1; Han, Jianying1,12; Dai, Huanqin1
刊名Applied microbiology and biotechnology
2016-10-01
卷号100期号:19页码:8349-8357
关键词Biotransformation [4+2] cycloaddition reaction Tanshinone iia Hypocrea sp
ISSN号0175-7598
DOI10.1007/s00253-016-7488-6
通讯作者Zhang, lixin(zhanglixin@im.ac.cn) ; Liu, xueting(liuxt2010@gmail.com)
英文摘要The biotransformation of tanshinone iia to a new antibacterial agent tanshisorbicin (1) by the fungus hypocrea sp. (as 3.17108) is described. the structure of tanshisorbicin is a hybrid of tanshinone iia (2) and sorbicillinol (3). the latter is a metabolite produced by hypocrea sp. the structure of tanshisorbicin was determined using mass spectrometry, nmr spectroscopy, and ecd calculations. the anti-mrsa activity of 1 was found to be significantly higher than that of the parent substrate tan iia. preliminary experiments indicate that tanshisorbicin is formed via a [4+2] cycloaddition reaction that is likely catalyzed by microbial enzyme.
WOS关键词DIELS-ALDER REACTION ; NATURAL-PRODUCTS ; VERTICILLIUM-INTERTEXTUM ; BIOSYNTHESIS ; BISORBICILLINOLIDE ; BISORBIBUTENOLIDE ; BIOAVAILABILITY ; IDENTIFICATION ; TRANSFORMATION ; INTERMEDIATE
WOS研究方向Biotechnology & Applied Microbiology
WOS类目Biotechnology & Applied Microbiology
语种英语
出版者SPRINGER
WOS记录号WOS:000383242500008
内容类型期刊论文
URI标识http://www.corc.org.cn/handle/1471x/2376177
专题中国科学院大学
通讯作者Zhang, Lixin; Liu, Xueting
作者单位1.Chinese Acad Sci, Inst Microbiol, Key Lab Pathogen Microbiol & Immunol, Beijing 100101, Peoples R China
2.Sichuan Acad Agr Sci, Soil & Fertilizer Res Inst, Chengdu 610066, Peoples R China
3.Sichuan Agr Univ, Dept Microbiol, Coll Resource & Environm, Chengdu 611130, Peoples R China
4.King Saud Univ, Dept Pharmacognosy, Coll Pharm, Riyadh 11451, Saudi Arabia
5.Assiut Univ, Dept Pharmacognosy, Fac Pharm, Assiut 71526, Egypt
6.Chinese Acad Med Sci, Inst Mat Med, Dept Med Chem, Beijing 100050, Peoples R China
7.Peking Union Med Coll, Beijing 100050, Peoples R China
8.Chinese Acad Sci, Inst Microbiol, State Key Lab Mycol, Beijing, Peoples R China
9.Univ Texas Austin, Coll Pharm, Div Med Chem, Austin, TX 78712 USA
10.Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
推荐引用方式
GB/T 7714
He, Wenni,Liu, Miaomiao,Li, Xiaolin,et al. Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity[J]. Applied microbiology and biotechnology,2016,100(19):8349-8357.
APA He, Wenni.,Liu, Miaomiao.,Li, Xiaolin.,Zhang, Xiaoping.,Abdel-Mageed, Wael M..,...&Liu, Xueting.(2016).Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity.Applied microbiology and biotechnology,100(19),8349-8357.
MLA He, Wenni,et al."Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity".Applied microbiology and biotechnology 100.19(2016):8349-8357.
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