Photochemical Degradation of Hyperforin

Maurizio      D'Auria; Lucia      Emanuele; Rocco      Racioppi

Abstract

Irradiation of hyperforin in acetonitrile gave a single degradation product with a first order kinetics (k = 3.23 M h-1). The degradation product was a 1:1 tautomeric mixture of 2-methyl-3-hydroxy-4-(1-oxo-2-methyl-1-propyl)-1,5- dioxo-6-(3methyl-1-but-2-enyl)-2-cyclohexene and 2-methyl-1,3,5-trioxo-4-(1-hydroxy-2-methyl-1-propylene)-6-(3-methyl- 1-but-2-enyl)-cyclohexane. The product can also be obtained through three Norrish II reactions, followed by a fragmentation reaction.

Keywords: Photochemical Degradation, Hyperforin, Irradiation, acetonitrile, first order kinetics, tautomeric mixture, three Norrish II reactions, fragmentation reaction