Water-Soluble Constituents of Fennel. III. Fenchane-Type monoterpenoid Glycosides

Abstract

From the water-soluble portion of the methanolic extract of fennel, the fruit of Foeniculum vulgare MILLER (Umbelliferae), nine fenchane-type monoterpenoid glycosides were isolated.Based on the spectral evidence, they were characterized as (1R, 4R, 5S)-5-hydroxyfenchone β-D-glucopyranoside, (1R, 4S, 6R)-6-hydroxyfenchone β-D-glucopyranoside, (1R, 3S, 4S, 6R)-6, 9-dihydroxyfenchone 6-O-β-D-glucopyranoside, (1S, 4R)-10-hydroxyfenchone β-D-glucopyranoside, (1S, 3S, 4R)-9, 10-dihydroxyfenchone 10-O-β-D-glucopyranoside, (1S, 3R, 4R)-8, 10-dihydroxyfenchone 10-O-β-D-glucopyranoside, (1R, 2R, 4S, 6R)-2, 6-dihydroxyfenchane 2-O-β-D-glucopyranoside, (1R, 2S, 4R, 5S)-2, 5-dihydroxyfenchane 2-O-β-D-glucopyranoside and (1S, 2S, 4S, 6R, 7S)-2, 6, 7-trihydroxyfenchane 2-O-β-D-glucopyranoside. The latter seven glycosides were new, and this is the first report of the isolation of fenchane-type glucosides from plant sources.