Abstract
Three new andrastin-type meroterpenoids penimeroterpenoids A–C (1–3) together with two known analogs (4 and 5) were isolated from the cultures of the marine-derived Penicillium species (sp.). The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of 1–3 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed moderate cytotoxicity against A549, HCT116, and SW480 cell lines.
Highlights
Meroterpenoids are hybrid natural products with partial structure fragments derived from terpenoids [1,2]
The andrastin-type meroterpenoids derived from 5-dimethylorsellinic acid (DMOA) and farnesyl diphosphate (FPP)
In our ongoing search for new bioactive secondary metabolites from marine-derived fungi, the fungus Penicillium sp. (A18), isolated from a deep-water sediment sample that was collected at a depth of 5115 m in the East Pacific, was selelected for chemical investigations
Summary
Meroterpenoids are hybrid natural products with partial structure fragments derived from terpenoids [1,2]. Three new andrastin-type meroterpenoids, which have been named penimeroterpenoids A–C (1–3), together with two known compounds, andrastone E (4) [22] and citreohybridonol (5) [11] (Figure 1), were isolated and identified from the culture extract of the fungus. Their structures were established by a detailed interpretation of 1D/2D NMR spectroscopic and mass spectrometric data, and the absolute configurations of 1–3 were determined by electronic circular dichroism (ECD) calculations.
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