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.
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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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