Abstract
The saltwater culture of a Penicillium chrysogenum strain isolated from the Mediterranean sponge Ircinia fasciculata yielded three new sorbicillin-derived compounds ( 1– 3 ), whose structures were elucidated mainly by 2D NMR and mass spectrometry. Among them, sorbicillactones A ( 1 ) and B ( 2 ) are the first sorbicillinoid natural products that contain nitrogen. Compound 1 is anti-HIV active and it exhibits a strong cytotoxic activity against L5178y leukemic cells, combined with a relatively low toxicity to cervical carcinoma HeLa S3 cells and pheochromocytoma PC 12 cells. The absolute configurations of 1 and 2 were elucidated by quantum chemical calculation of circular dichroism (CD) spectra. Another compound isolated, sorbivinetone ( 3 ), might be an artifact derived from sorbicillinol ( 4 ) by Diels–Alder reaction with ethyl vinyl ether. Furthermore, the known sorbicillinoid fungal metabolites oxosorbicillinol ( 5 ), sorbicillin ( 6 ), and bisvertinolone ( 7 ) were identified, as well as the alkaloids meleagrine and roquefortine C. The biosynthetic origin of sorbicillactone A ( 1 ) from acetate, alanine, and methionine was investigated by feeding experiments with 13C-labeled precursors.
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