Journal
MARINE DRUGS
Volume 10, Issue 6, Pages 1266-1287Publisher
MDPI
DOI: 10.3390/md10061266
Keywords
purpurogemutantin; purpurogemutantidin; sesquiterpene; meroterpenoid; structure determination; antitumor activity; Penicillium purpurogenum; marine-derived fungus; DES mutagenesis
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Funding
- National Natural Science Foundation [30973631, 30572279, 30472079, 30171102, 81172976]
- National Science and Technology Major Project [2009ZX09103-019, 2009ZX09301-002]
- National High Technology Research & Development Program [2007AA09Z411]
- Chinese Academy of Sciences [KSCX2-EW-G-6]
- COMRA [DYXM-115-02-2-09]
- AMMS, China
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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.
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