Structure-Activity Relationship and Prediction of the Electron-Transfer Potential of the Xanthones Series

The structure-activity relationships of 31 xanthones were analyzed by using the ferric reducing antioxidant power (FRAP) assay to determine their electron-transfer (ET) potential. It was proven that the ET potential of xanthones was dominated by four moieties (i.e. hydroquinone moiety, 5,6-catechol moiety, 6,7-catechol moiety, and 7,8-catechol moiety) and was only slightly affected by other structural features, including a single phenolic OH group, the resorcinol moiety, the transannular dihydroxy moiety, a methoxy group, a sugar residue, an isoprenyl group, a cyclized isoprenyl group, and an isopentanol group. The results could be used to predict the ET potentials of other antioxidant xanthones.