Isolation and Structure Elucidation of Hyperibine J [Revised Structure of Adhyperfirin (7-Deprenyl-13-methylhyperforin)]: Synthesis of Hyperibone J

Structure elucidation of hyperibine J, a new polycyclic polyprenylated acylphloroglucinol isolated from Hypericum sp., was investigated. Molecular weight and spectroscopic data comparison with adhyperfirin (7‐deprenyl‐13‐methylhyperforin) declared a structure revision of the latter. Moreover, chemical transformation to hyperibone J confirmed its proposed structure and absolute configuration. Hyperibine J was found to be very similar to hyperforin and possesses a methyl substituent instead of a prenyl group at C‐1. Structure elucidation of hyperibine J, a new polycyclic polyprenylated acylphloroglucinol isolated from Hypericum sp., is described. Molecular weight and spectroscopic data comparison with adhyperfirin (7‐deprenyl‐13‐methylhyperforin) declared a structure revision of the latter. Hyperibine J is very similar to hyperforin and possesses a methyl substituent instead of a prenyl group at C‐1; mCPBA = meta‐chloroperoxybenzoic acid.