Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp

  • Bioorg Med Chem Lett. 2010 Jun 1;20(11):3284-6. doi: 10.1016/j.bmcl.2010.04.043.
Chang-Lun Shao  1 ,  Chang-Yun Wang ,  Yu-Cheng Gu ,  Mei-Yan Wei ,  Jia-Hui Pan ,  Dong-Sheng Deng ,  Zhi-Gang She ,  Yong-Cheng Lin
Affiliations
  • 1. Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
PMID: 20452770 DOI: 10.1016/j.bmcl.2010.04.043
Abstract

A new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system, named penicinoline (1) was isolated from a mangrove endophytic fungus. The structure of 1 was elucidated by spectroscopic methods and comparison with its derivative, penicinotam (1a), an unexpected lactam that was obtained from 1 by intramolecular dehydration. The structure of 1a was unambiguously confirmed by single-crystal X-ray analysis. Penicinoline (1) showed potent in vitro cytotoxicity toward 95-D and HepG2 cell lines with IC(50) values of 0.57 and 6.5 microg/mL, respectively.

Products