Spirocitrinols A and B, citrinin derivatives with a spiro[chromane-2,3′-isochromane] skeleton from Penicillium citrinum

Abstract

Spirocitrinols A (1) and B (2), two new citrinin-derived metabolites possessing a spiro[chromane-2,3′-isochromane] skeleton, were isolated from cultures of Penicillium citrinum. Their structures were elucidated primarily by NMR experiments. The absolute configurations of 1 and 2 were assigned by electronic circular dichroism calculations. Compound 2 is the first naturally occurring trimeric citrinin derivative with a spiro[chromane-2,3′-isochromane] core. Compound 1 showed modest cytotoxicity against A549 human tumor cells.