Two novel cyclohexanone-monocyclic polycyclic polyprenylated acylphloroglucinols from Garcinia multiflora fruits

Two novel cyclohexanone-monocyclic polyprenylated acylphloroglucinol (C-MPAP) derivatives, named norgarmultinones A (1) and B (2), were isolated from the fruits of Garcinia multiflora. Their structures were clarified by NMR, HRESIMS and calculated electronic circular dichroism (ECD) spectra. Compound 2 is the first example of naturally occurring C-MPAPs containing tetrahydropyran moiety by the cyclization of an enolic hydroxyl with an isogeranyl side chain. The reasonable biosynthetic routes of 1 and 2 were also put forward.