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Mar Drugs. 2012 Jun;10(6):1266-87. doi: 10.3390/md10061266. Epub 2012 Jun 4.

Purpurogemutantin and purpurogemutantidin, new drimenyl cyclohexenone derivatives produced by a mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59.

Author information

1
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. fang_shiming@163.com

Abstract

Two new drimenyl cyclohexenone derivatives, named purpurogemutantin (1) and purpurogemutantidin (2), and the known macrophorin A (3) were isolated from a bioactive mutant BD-1-6 obtained by random diethyl sulfate (DES) mutagenesis of a marine-derived Penicillium purpurogenum G59. Structures and absolute configurations of 1 and 2 were determined by extensive spectroscopic methods, especially 2D NMR and electronic circular dichroism (ECD) analysis. Possible biosynthetic pathways for 1-3 were also proposed and discussed. Compounds 1 and 2 significantly inhibited human cancer K562, HL-60, HeLa, BGC-823 and MCF-7 cells, and compound 3 also inhibited the K562 and HL-60 cells. Both bioassay and chemical analysis (HPLC, LC-ESIMS) demonstrated that the parent strain G59 did not produce 1-3, and that DES-induced mutation(s) in the mutant BD-1-6 activated some silent biosynthetic pathways in the parent strain G59, including one set for 1-3 production.

KEYWORDS:

DES mutagenesis; Penicillium purpurogenum; antitumor activity; marine-derived fungus; meroterpenoid; purpurogemutantidin; purpurogemutantin; sesquiterpene; structure determination

PMID:
22822371
PMCID:
PMC3397438
DOI:
10.3390/md10061266
[Indexed for MEDLINE]
Free PMC Article
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