An easy and stereoselective rearrangement of an abietane diterpenoid into a bioactive microstegiol derivative

Simões, Maria de Fátima; Rijo, Patrícia; Duarte, Aida; Matias, Diogo; Rodríguez, Benjamín

http://hdl.handle.net/10451/3935

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Authors

Simões, Maria de Fátima

Abstract(s)

Parvifloron D was isolated from Plectranthus ecklonii together with sugiol and mixtures of β-sitosterol and stigmasterol and ursolic and oleanolic acids. Treatment of parvifloron D [2α-(4-hydroxy)benzoyloxy-11-hydroxy-5,7,9(11),13-abietatetraen-12-one] with acid-washed molecular sieves gave the microstegiol derivative 2β-(4-hydroxy)benzoyloxy-11β-hydroxy-4(5 → 11),20(10 → 5)diabeo-5(10),6,8,13-abietatetraen-12-one in a moderate yield (26%). The new microstegiol derivative inhibited the growth of some Staphylococcus and Enterococcus species with significant MIC values ranging from 3.91 to 7.81 μg/ml.