Dfpenicimeroterpenoid A, Meroterpenoids with 6/6/6/4/5 Polycyclic Skeletons from the Marine-Derived Fungus Penicillium sp. DF71.

A novel andrastin-type meroterpenoid, dfpenicimeroterpenoid A (1), featuring an unprecedented fused 6/6/6/4/5 pentacyclic skeleton is described, along with four new analogues from marine-derived fungus Penicillium sp. DF71. The structures were established by analysis of their spectroscopic data, single-crystal X-ray diffraction, and quantum chemical calculations of electronic circular dichroism spectra. Compound 2 showed significant pro-angiogenic activity at a concentration of 20 μM, based on a zebrafish model. Furthermore, a plausible biosynthetic pathway for 1 is proposed.