OXIDATION-PRODUCTS OF HYPERFORIN FROM HYPERICUM-PERFORATUM

The isolation of two oxidation products of hyperforin from the aerial parts of Hypericum perforatum and their structure determination by mea ns of 2D NMR methods is reported. The products had the same 1-(2-methy l-1-oxopropyl)-2,12-dioxo-3,10 beta-bis(3-methyl-2-butenyl)-11 beta-me thyl-11 3-pentenyl)-5-oxatricyclo[6.3.1.0(4.8)]-3-dodecene skeleton. I n addition, one of them, with the same number of carbons as hyperforin (C35H52O5), contained a 1-methyl-1-hydroxyethyl group in the 6 beta-p osition, whereas the other compound (a hemiacetal, C32H46O5), presumab ly a degradation product of hyperforin, exhibited a 6-hydroxy function . The latter was an inseparable mixture of 6 alpha- and 6 beta-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual :inter conversion. (C) 1998 Elsevier Science Ltd. All rights reserved.