Five New Monoterpene Glycosides and Other Compounds form Foeniculi Fructus (Fruit of Foeniculum vulgare MILLER)

Abstract

Five new monoterpene glycosides, foeniculosides V, VI, VII, VIII and IX, were isolated form Foeniculi Fructus (fruit of Foeniculum vulgare MILLER) along with seven known compounds, zizybeoside I, icaviside A₄, syringin, sinapyl alcohol 1, , 3'-di-O-β-D-glucopyranoside, adenosine, threo-anethole glycol and erythro-anethole glycol. The structures of foeniculosides V, VI, VII, VIII and IX were characterized as β-D-glucopyranosides of (1S, 2R, 4S)-2, 4-dihydroxy-1, 8-cineole-2-O-, (1R, 4R, 6R)-4, 6-dihydroxy-1, 8-cineole-6-O-, (1R, 4R, 6R)-4, 6-dihydroxy-1, 8-cineole-4-O-, (1S, 2R, 4R, 6S)-2, 6-dihydroxy-1, 8-cineole-2-O- and (1S, 2R, 4S, 5R)-2, 5-dihydroxy-1, 8-cineole-2-O-, respectively, on the basis of chemical and spectroscopic data.