Eremophilane-Type Sesquiterpenoids from an Acremonium sp. Fungus Isolated from Deep-Sea Sediments

  • J Nat Prod. 2016 Apr 22;79(4):1035-47. doi: 10.1021/acs.jnatprod.5b01103.
Zhongbin Cheng  1 Jingjun Zhao  2 Dong Liu  1 Peter Proksch  3 Zhimin Zhao  2 Wenhan Lin  1
Affiliations
  • 1. State Key Laboratory of Natural and Biomimetic Drugs, Institute of Ocean Research, Peking University , Beijing, 100191, People's Republic of China.
  • 2. School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou, Guangdong 510006, People's Republic of China.
  • 3. Institute für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf , 40225 Düsseldorf, Germany.
Abstract

Chemical examination of an EtOAc extract of a cultured Acremonium sp. fungus from deep-sea sediments resulted in the isolation of 15 new eremophilane-type sesquiterpenoids, namely, acremeremophilanes A-O (1-15), together with seven known analogues. The structures of new compounds were determined through extensive spectroscopic analyses, in association with chemical conversions and ECD calculations for configurational assignments. The PKS-derived 4-hexenoic acid unit in 2-6 is rarely found in nature. All compounds were evaluated for inhibitory effects toward nitric oxide production induced by lipopolysaccharide in RAW 264.7 macrophage cells. Compounds 2-6 and 14 exhibited inhibitory effects with IC50 values ranging from 8 to 45 μM.