Asperflavipine A: A Cytochalasan Heterotetramer Uniquely Defined by a Highly Complex Tetradecacyclic Ring System from Aspergillus flavipes QCS12. Issue 19 (5th April 2017)

• Record Type: Journal Article
• Authors: Zhu, Hucheng; Chen, Chunmei; Tong, Qingyi; Yang, Jing; Wei, Guangzheng; Xue, Yongbo; Wang, Jianping; Luo, Zengwei; Zhang, Yonghui
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 19(2017)
• Page Start: 5242
• Page End: 5246
• Publication Date: 2017-04-05
• Subjects: biological activity -- heterotetramers -- heterotrimers -- natural products -- structure elucidation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201701125
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Asperflavipines A (1 ) and B (2 ), two structurally complex merocytochalasans, were isolated from Aspergillus flavipes . Asperflavipine A (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. Asperflavipine B (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 of1 and2 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 of1 adds a new dimension to the diversity of the cytochalasan family. Compound1 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). Abstract : The height of sophistication : Asperflavipine A (1 ), an unprecedented cytochalasan heterotetramer uniquely defined by 5/6/11/5/6/5/6/5/6/5/5/11/6/5 fused tetradecacyclic rings, was isolated from Aspergillus flavipes QCS12 along with a cytochalasan heterotrimer, asperflavipine B. Compound1 showed moderate cytotoxicity and induced apoptosis in Jurkat, NB4, and HL60 cells through the activation of caspase‐3 and degradation of PARP.