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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.

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