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Anti-inflammatory phloroglucinol derivatives from Hypericum empetrifolium
Sara L Crockett1, Eva-Maria Wenzig, Olaf Kunert
1Institute for Pharmaceutical Sciences, Department of Pharmacognosy, Karl-Franzens-University-Graz, 8010 Graz, Austria.
None:
Phytochemical investigation of Hypericum empetrifolium Willd. (Clusiaceae), a species native to Greece and Turkey has led to the bioassay-guided identification of two acylphloroglucinol derivatives with potent in vitro anti-inflammatory activity. Using NMR spectroscopy and mass spectrometry, the acylphloroglucinol derivatives were characterized as 3-geranyl-1-(2'-methylpropanoyl)phloroglucinol (1) and 3-geranyl-1-(2'-methylbutanoyl)phloroglucinol (2). Hypotheses are proposed regarding the biosynthetic origin of these and similar acylphloroglucinols from related Hypericum species. Compounds 1 and 2 were evaluated for in vitro inhibitory activity against COX-1, COX-2 and 5-LOX catalyzed LTB(4) formation. Compound 1 displayed good activity (IC(50) values: 6.0, 29.9, and 2.2 microM, respectively) in all three assays. Compound 2 showed good activity (IC(50) value: 5.8 microM) against LTB(4) formation and moderate activity (IC(50) value: 26.2 microM) against COX-1.
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