4.8 Article

AsperflavipineA: A Cytochalasan Heterotetramer Uniquely Defined by a Highly Complex Tetradecacyclic Ring System from Aspergillus flavipes QCS12

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 19, 页码 5242-5246

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701125

关键词

biological activity; heterotetramers; heterotrimers; natural products; structure elucidation

资金

  1. National Natural Science Foundation of China [81573316, 21602068, 31370372, 21502057, 31570361, 31670354]
  2. Changjiang Scholars Program
  3. China Postdoctoral Science Foundation [2015M580647, 2016T90695]

向作者/读者索取更多资源

AsperflavipinesA (1) and B (2), two structurally complex merocytochalasans, were isolated from Aspergillus flavipes. AsperflavipineA (1), which contains two cytochalasan moieties and two epicoccine moieties, is the first cytochalasan heterotetramer to be discovered. It is uniquely defined by 5/6/11/5/6/5/6/5/6/5/5/11/6/5 fused tetradecacyclic rings with three continuous bridged ring systems. AsperflavipineB (2) is a cytochalasan heterotrimer containing a cytochalasan and two epicoccine moieties with a 5/6/11/5/5/6/5/6/5 nonacyclic ring system. The hypothetical biosynthesis of 1 and 2 is proposed to involve Diels-Alder and [3+2] cycloaddition reactions as key steps and reveals unparalleled plasticity in the biosynthesis of merocytochalasans. The existence of 1 adds a new dimension to the diversity of the cytochalasan family. Compound 1 showed moderate cytotoxicity and induced apoptosis in Jurkat, NB4, and HL60 cells through the activation of caspase-3 and degradation of poly(ADP-ribose) polymerase (PARP).

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