Pericoannosin A, a Polyketide Synthase–Nonribosomal Peptide Synthetase Hybrid Metabolite with New Carbon Skeleton from the Endophytic Fungus Periconia sp.

Four new polyketide synthase–nonribosomal peptide synthetase (PKS–NRPS) hybrid metabolites, pericoannosin A (1), with an unusual hexahydro-1H-isochromen-5-isobutylpyrrolidin-2-one skeleton, and three cytochalasans, periconiasins D–F (2–4), were isolated from the endophytic fungus Periconia sp. F-31. Their structures and absolute configurations were elucidated through extensive spectroscopic analyses, calculated ECD, and single-crystal X-ray diffraction (Cu Kα). A possible biogenetic pathway is proposed. Compounds 1 and 4 showed anti-HIV activity with IC50s of 69.6 and 29.2 μM, respectively.