Abstract

ARELLANO-MARTINEZ, Raquel  and  DELGADO, Guillermo. Hypargyrin A, a Hemiacetalic Germacrolide from Viguiera hypargyrea (Asteraceae): Biogenetic Implications and Biological Evaluation. J. Mex. Chem. Soc [online]. 2010, vol.54, n.2, pp.117-121. ISSN 1870-249X.

A new hemiacetalic germacrolide 6, named hypargyrin A, was isolated from the aerial parts of Viguiera hypargyrea, along with the known compounds (8R,9R)-β-caryophyllene epoxide, entkaur-16-en-19-oic acid (1), hispidulin (2), 8β-epoxyangeloyloxy-14-acetoxy-tithifolin (3), 8β-epoxyangeloyloxy-14-hydroxy-tithifolin (4) and budlein B (5). Spectroscopic analysis of 6 allowed the structural correction of a compound isolated from Blainvillea gayana. Budlein B (5) can be considered the biogenetic precursor of 6, and two pathways for its formation are proposed. Hypargyrin A (6) did not display significant anti-inflammatory activity against ear edema in mice induced by TPA, but showed cytotoxic activity against HeLa (IC₅₀ 35.1 µM) and Hep-2 (39.2 µM) human cells.

Keywords : Asteraceae; Viguiera hypargyrea; sesquiterpene lactones; germacrolides; hypargyrin A; budlein B; biogenesis; anti-inflammatory activity; cytotoxic activity.

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