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Prenylated Acylphloroglucinols from Hypericum jovis with Anti-inflammatory Potential#.

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Title: Prenylated Acylphloroglucinols from Hypericum jovis with Anti-inflammatory Potential#.
Authors: Grafakou, Maria-Eleni, Barda, Christina, Pintać, Diandra, Lesjak, Marija, Heilmann, Jörg, Skaltsa, Helen
Source: Planta Medica; 2021, Vol. 87 Issue 14, p1184-1191, 8p
Subject Terms: IN vitro studies, PHENOLS, ANTI-inflammatory agents, NUCLEAR magnetic resonance spectroscopy, HYPERICUM perforatum, QUERCETIN, TUMOR necrosis factors, CELL adhesion molecules, TOXICITY testing, CELL lines, INFLAMMATORY mediators, BIOLOGICAL assay
Abstract: Thirteen 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). [ABSTRACT FROM AUTHOR]
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Database: Complementary Index
Description
Abstract:Thirteen 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 IC<subscript>50</subscript> 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). [ABSTRACT FROM AUTHOR]
ISSN:00320943
DOI:10.1055/a-1556-9721