WATER-SOLUBLE CONSTITUENTS OF FENNEL - II - 4 ERYTHRO-ANETHOLE GLYCOLGLYCOSIDES AND 2 P-HYDROXYPHENYLPROPYLENE GLYCOL GLYCOSIDES

Four erythro-anethole glycol monoglucosides were isolated from the met hanolic extract of fennel, the fruit of Foeniculum vulgare MILLER (Umb elliferae). From chemical and spectroscopic evidence, they were charac terized as (1'S,2'R)-erythro-anethole glycol 1'-O-beta-D-glucopyranosi de, (1'R,2'S)-erythro-anethole glycol 1'-O-beta-D-glucopyranoside, (1' S,2'R)-erythro-anethole glycol 2'-O-beta-D-glucopyranoside, (1'R,2'S)- erythro-anethole glycol 2'-O-beta-D-glucopyranoside, respectively Alon g with these glycosides, two new glycosides of p-hydroxyphenylpropylen e glycol were obtained and characterized as threo-1'-(4-hydroxyphenyl) propane-1',2'-diol 4-O-beta-D-glucopyranoside (a mixture of two stereo isomeric forms) and 1'-(4-hydroxyphenyl)propane-2',3'-diol 4-O-beta-D- glucopyranoside (an epimeric mixture at C-2') from spectral evidence. This is the first report of the isolation of all four O-beta-D-glucopy ranosides which have the glucosyl unit attached to the hydroxy group o f the erythro-glycol function of individual stereoisomeric aglycones.