Isolation and Structure Elucidation of Hyperibine J [Revised Structure of Adhyperfirin (7‐Deprenyl‐13‐methylhyperforin)]: Synthesis of Hyperibone J. Issue 2 (5th December 2014)

• Record Type: Journal Article
• Authors: Mitsopoulou, Kornilia P.; Vidali, Veroniki P.; Maranti, Anna; Couladouros, Elias A.
• Is Part Of: European journal of organic chemistry. Issue 2(2015)
• Page Start: 287
• Page End: 290
• Publication Date: 2014-12-05
• Subjects: Natural products -- Structure elucidation -- Polycycles -- Phloroglucinols -- Prenyl groups; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403264
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 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; m CPBA = meta ‐chloroperoxybenzoic acid.