Lovastatin and its derivatives are well-known as a type of lipid-lowering drugs in medicinal chemistry of natural products, which typically feature a rigid decalin core structure with almost no other carbon rings. Herein, aculeatones A (1) and B (2), two highly modified lovastatin derivatives with an unreported 6/6/3-tricyclic carbon skeleton, in addition to four undescribed lovastatin derivatives aculeatones C–F (3–6), were isolated from the fungus Aspergillus aculeatus. Their structures with absolute configurations were characterized by comprehensive spectroscopic, quantum chemical calculations, electronic circular dichroism (ECD) analyses, the modified Mosherʼs method, and single-crystal X-ray diffraction. The plausible biosynthetic pathway of 1 and 2 was proposed, and the biomimetic transformation of 1 was achieved starting from 3. Biologically, compounds 3, 5, and 6 significantly inhibited the accumulation of lipid in an oleic acid-treated HepG2 cell model.

You have access to this article

Please wait while we load your content... Something went wrong. Try again?