A new ionone glucoside and terpenoid constituents from Achillea Biebersteinii and their antifungal activity

Abstract

A new ionone glucoside, (-)(4R*, 5R*)-5-(β-D- glucopyranosyloxymethyl)-4-hydroxy-3, 5-dimethyl-4-((E)-3-oxobut-1-enyl) cyclohex-2-enone (biebersteiniside) (1), in addition to four known compounds, 6-epiroseoside (2), ascaridole (3), strictic acid (4) and centipedic acid (5) have been isolated from the aerial parts of Achillea biebersteinii Afan. The structures were determined from extensive 500 MHz NMR 1D (1H and 13C NMR) and 2D (1H-1H COSY, HMQC, HMBC and NOESY) spectroscopic data. Compounds 2-5 are reported for the first time from this plant. In addition, compounds 1a and 3-5 showed antifungal activity.