Asperchalasine A, a Cytochalasan Dimer with an Unprecedented Decacyclic Ring System, from Aspergillus flavipes

Angewandte Chemie
Hucheng ZhuYonghui Zhang

Abstract

Asperchalasine A (1), the first cytochalasan dimer featuring a unique decacyclic 5/6/11/5/5/6/5/11/6/5 ring system consisting of 20 chiral centers, was isolated from the culture broth of Aspergillus flavipes. Three biogenetically related intermediates, asperchalasines B-D (2-4), were also isolated. Their structures, including their absolute configurations, were elucidated using a combination of HRESIMS, NMR, ECD, molecular modeling, and single-crystal X-ray diffraction techniques. Compound 1, which possesses an unprecedented 13-oxatetracyclo[7.2.1.1(2,5).0(1,6)]tridec-8,12-dione core structure, is the first example of a dimeric cytochalasan alkaloid. The biogenetic pathways of 1-4 were described starting from the co-isolated compounds 5 and 6. More importantly, 1 induced significant G1-phase cell cycle arrest by selectively inhibiting cyclin A, CDK2 and CDK6 in cancerous, but not normal, cells, highlighting it as a potentially selective cell cycle regulator against cancer cells.

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Citations

May 20, 2016·Scientific Reports·Weiguang SunYonghui Zhang
Aug 30, 2017·Natural Product Reports·Elizabeth Skellam
Jul 20, 2018·Chemistry, an Asian Journal·Abdul SadeerPak-Hing Leung
Aug 16, 2018·Angewandte Chemie·Xianwen LongJun Deng
Sep 8, 2018·Angewandte Chemie·Ruiyang BaoYefeng Tang
Sep 22, 2018·Angewandte Chemie·Julius R ReyesDirk Trauner
Sep 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Qing-Feng GuoLin Chen
May 16, 2020·Organic & Biomolecular Chemistry·Xiaogang PengHanli Ruan
Apr 29, 2016·Angewandte Chemie·Chong TianYefeng Tang
Feb 17, 2017·Scientific Reports·Guangzheng WeiYonghui Zhang
Aug 15, 2019·Biomolecules·Jun Yeon ParkKi Sung Kang
Jul 27, 2018·Journal of Asian Natural Products Research·Zhen LiuYun-Bao Liu
Jan 26, 2021·Natural Product Research·Li ChengYong-Hui Zhang
Jul 4, 2018·Journal of Natural Products·Wenjing WangYonghui Zhang
May 18, 2019·Organic Letters·Chongqing WangElizabeth Skellam
Jul 7, 2020·Journal of Natural Products·Huaqiang LiYonghui Zhang
Sep 23, 2021·Accounts of Chemical Research·Ruiyang BaoYefeng Tang
Nov 17, 2021·Journal of Biochemical and Molecular Toxicology·Jhansi Nathan, Arunkumar Ramachandran

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