A new guaianolide and other constituents from Achillea ligustica

Biochemical Systematics and Ecology
2008.0

Abstract

As part of research on the Asteraceae family, the chemical constituents of aerial parts of Achillea ligustica All. collected in Jijel, eastern Algeria in June 2004 were studied. Air-dried flowering aerial parts were extracted with ethanol using a Soxhlet apparatus, and the extract was fractionated by column chromatography (silica gel, Sephadex LH-20) with various eluents (hexane-EtOAc, CH₂Cl₂-Me₂CO, etc.). A new chlorinated guaianolide, named algerianolide, was isolated along with several known compounds: (E)-ethyl-3,7-dimethyl-3,6-octadienoate, borneol, 2-oxoisodauc-5-en-12-al, 1-tricontanol, β-sitosterol, filifolide A, and santin. The structure of algerianolide was identified as 2α-chloro-9α-acetoxy-1β,10α-dihydroxy-3β,4β-epoxy-5α,7α-H-guaia-11(13)-en-12,6α-olide through spectral analysis (HR-EI-MS, 2D NMR including COSY, ROESY, HSQC, HMBC) and confirmed by X-ray diffraction. Chemotaxonomic significance analysis revealed that this is the first report of a sesquiterpene lactone with a chlorine atom at C-2 in the Achillea genus, differing from previous findings where chlorine was at C-1, C-3, or C-4.

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