WATER-SOLUBLE CONSTITUENTS OF FENNEL - III - FENCHANE-TYPE MONOTERPENOID GLYCOSIDES

From the water-soluble portion of the methanolic extract of fennel, th e fruit of Foeniculum vulgare MILLER (Umbelliferae), nine fenchane-typ e monoterpenoid glycosides were isolated. Based on the spectral eviden ce, they were characterized as (1R,4R,5S)-5-hydroxyfenchone beta-D-glu copyranoside, (1R,4S,6R)-6-hydroxyfenchone beta-D-glucopyranoside, (1R ,3S,4S,6R)-6,9-dihydroxyfenchone 6-O-beta- D-glucopyranoside, (1S,4R)- 10-hydroxyfenchone beta-D-glucopyranoside, (1S,3S,4R)-9,10-dihydroxyfe nchone 10-O-beta-D-glucopyranoside, (1S,3R,4R)-8,10-dihydroxyfenchone 10-O-beta-D-glucopyranoside, (1R,2R,4S,6R)-2,6-dihydroxyfenchane 2-O-b eta-D-glucopyranoside, (1R,2S,4R,5S)-2,5-dihydroxyfenchane 2-O-beta-D- glucopyranoside and (1S,2S,4S,6R,7S)-2,6,7-trihydroxyfenchane 2-O-beta -D-glucopyranoside. The latter seven glycosides were new, and this is the first report of the isolation of fenchane-type glucosides from pla nt sources.