Penicillivinacine, antimigratory diketopiperazine alkaloid from the marine-derived fungus Penicillium vinaceum

Abstract

Abstract In the course of our ongoing search for biologically active compounds from marine-derived fungi, the organic extract of the marine-derived fungus Penicillium vinaceum species was investigated. Seven compounds including a new alkaloid with an unprecedented carbon skeleton, penicillivinacine (1) together with six previously reported ones were isolated. The known compounds were identified as indol-3-carbaldehyde (2), α-cyclopiazonic acid (3), terretrione A (4), brevianamide F (5), cyclo-d-Trp-l-pro (6) and citreoisocoumarin (7). Their structures were established by different spectroscopic data including 1D ( 1 H NMR and 13 C NMR) and 2D NMR (COSY, HSQC, HMBC and NOESY) studies as well as high-resolution mass spectral data. The isolated compounds were evaluated for their antimigratory activity against the human breast cancer cell line MDA-MB-231 as well as antimicrobial activities against different pathogens. Compounds 1 and 4 displayed potent antimigratory activities against the highly metastatic triple negative human breast cancer cells MDA-MB-231 with IC 50 of 18.4 and 17.7 μM, respectively. Furthermore, compounds 1-7 showed different antimicrobial activities.