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Purpurogemutantin and purpurogemutantidin, new drimenyl cyclohexenone derivatives produced by a mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59
Authors:Fang Shi-Ming  Cui Cheng-Bin  Li Chang-Wei  Wu Chang-Jing  Zhang Zhi-Jun  Li Li  Huang Xiao-Jun  Ye Wen-Cai
Institution: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:purpurogemutantin  purpurogemutantidin  sesquiterpene  meroterpenoid  structure determination  antitumor activity  Penicillium purpurogenum  marine-derived fungus  DES mutagenesis
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