Water-Soluble Constituents of Fennel. II. Four erythro-Anethole Glycol Glycosides and Two p-Hydroxyphenylpropylene Glycol Glycosides

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Four erythro-anethole glycol monoglucosides were isolated from the methanolic extract of fennel, the fruit of Foeniculum vulgare MILLER (Umbelliferae). From chemical and spectroscopic evidence, they were characterized as (1'S, 2'R)-erythro-anethole glycol 1'-O-β-D-glucopyranoside, (1'R, 2'S)-erythro-anethole glycol 1'-O-β-D-glucopyranoside, (1'S, 2'R)-erythro-anethole glycol 2'-O-β-D-glucopyranoside, (1'R, 2'S)-erythro-anethole glycol 2'-O-β-D-glucopyranoside, respectively. Along with these glycosides, two new glycosides of p-hydroxyphenylpropylene glycol were obtained and characterized as threo-1'-(4-hydroxyphenyl)propane-1', 2'-diol 4-O-β-D-glucopyranoside (a mixture of two stereoisomeric forms) and 1'-(4-hydroxyphenyl)propane-2', 3'-diol 4-O-β-D-glucopyranoside (an epimeric mixture at C-2') from spectral evidence.This is the first report of the isolation of all four O-β-D-glucopyranosides which have the glucosyl unit attached to the hydroxy group of the erythro-glycol function of individual stereoisomeric aglycones.
公益社団法人日本薬学会の論文
1998-10-15