Prenylated Acylphloroglucinols from Hypericum jovis with Anti-inflammatory Potential

Abstract

AbstractThirteen prenylated acylphloroglucinols (1–13), including 2 previously undescribed compounds (1) and (2), were isolated from Hypericum jovis. Their structures were elucidated by high-field NMR spectroscopy. The isolated prenylated acylphloroglucinols were evaluated for their anti-inflammatory effects in vitro through the reduction of the intercellular adhesion molecule 1 expression induced by TNF-α in the human microvascular endothelial cells 1 cell line. Compounds 3, 5, 6, 8, and 12 significantly reduced intercellular adhesion molecule 1 expression in a concentration-dependent manner with IC50 values of 16.9, 34.4, 4.0, 3.2, and 7.7 µM, respectively. In addition, compound 12 showed notable inhibitory activity on the formation of cyclooxygenase-1- and 12-lipoxygenase-derived inflammatory mediators in an ex vivo cyclooxygenase-lipoxygenase assay. Eleven further constituents were isolated (14–24), including the rare quercetin 3-O-(2-O-acetyl)-arabinofuranoside (18).