Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp.
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.
Shao
Chang-Lun
CL
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.
Wang
Chang-Yun
CY
Gu
Yu-Cheng
YC
Wei
Mei-Yan
MY
Pan
Jia-Hui
JH
Deng
Dong-Sheng
DS
She
Zhi-Gang
ZG
Lin
Yong-Cheng
YC
D000470:Alkaloids / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D018360:Crystallography, X-Ray; D006801:Humans; D008958:Models, Molecular; D010407:Penicillium / Q000737:chemistry*; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry / Q000494:pharmacology*; D015363:Quinolones / Q000737:chemistry / Q000494:pharmacology*
D000470:Alkaloids; D011763:Pyrrolizidine Alkaloids; D015363:Quinolones; C551309:penicinoline