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Chloropestolide A, an Antitumor Metabolite with an Unprecedented Spiroketal Skeleton from <i>Pestalotiopsis fici</i>

Ling LiuKey Laboratory of Systematic Mycology & Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, People’s Republic of China, New Drug Research and Development Center, North China Pharmaceutical Group Corporation, Shijiazhuang 050015, People’s Republic of China, and State Key Laboratory of Virology, Wuhan Institute of Virology, Chinese Academy of Sciences, Wuhan, 430071, People’s Republic of ChinaYan LiWuhan Institute of VirologyShuchun LiuKey Laboratory of Systematic Mycology & Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, People’s Republic of China, New Drug Research and Development Center, North China Pharmaceutical Group Corporation, Shijiazhuang 050015, People’s Republic of China, and State Key Laboratory of Virology, Wuhan Institute of Virology, Chinese Academy of Sciences, Wuhan, 430071, People’s Republic of ChinaZhihui ZhengKey Laboratory of Systematic Mycology & Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, People’s Republic of China, New Drug Research and Development Center, North China Pharmaceutical Group Corporation, Shijiazhuang 050015, People’s Republic of China, and State Key Laboratory of Virology, Wuhan Institute of Virology, Chinese Academy of Sciences, Wuhan, 430071, People’s Republic of ChinaXulin ChenKey Laboratory of Systematic Mycology & Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, People’s Republic of China, New Drug Research and Development Center, North China Pharmaceutical Group Corporation, Shijiazhuang 050015, People’s Republic of China, and State Key Laboratory of Virology, Wuhan Institute of Virology, Chinese Academy of Sciences, Wuhan, 430071, People’s Republic of ChinaHua ZhangWuhan Institute of VirologyLiang‐Dong GuoKey Laboratory of Systematic Mycology & Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, People’s Republic of China, New Drug Research and Development Center, North China Pharmaceutical Group Corporation, Shijiazhuang 050015, People’s Republic of China, and State Key Laboratory of Virology, Wuhan Institute of Virology, Chinese Academy of Sciences, Wuhan, 430071, People’s Republic of ChinaYongsheng CheWuhan Institute of Virology

2009en

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Annotatsiya

Chloropestolide A (1), a highly functionalized spiroketal with an unprecedented skeleton derived from a chlorinated bicyclo-[2.2.2]-oct-2-en-5-one ring and a 2,6-dihydroxy-4-methylbenzoic acid unit, has been isolated from the scale-up fermentation extract of Pestalotiopsis fici. The structure of 1 was elucidated by NMR spectroscopy and X-ray crystallography. 1 could be derived from the same Diels-Alder precursors as 2 and showed significant inhibitory effects on growth of two human cancer cell lines, HeLa and HT29, with GI(50) values of 0.7 and 4.2 microM, respectively.

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DOI: 10.1021/ol901039m

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