Cumin [Cuminum cyminum L.; Umbelliferae] is known to have been cultivated since antiquity, and is now mainly cultivated in North Africa, Iran, India, Indonesia and China. Its fruit has been used as a popular aromatic herb and spice, such as a main constituent of curry powder. The fruit has also been used for medicinal purposes as a remedy for diarrhea, flatulence and indigestion.1) It contains an essential oil (3-4%) rich in cuminaldehyde (main; 35-60%), and aand b-pinene, d-3-carene, 1,8-cineole, a-and b-phellandrene, p-cymene, limonene, a-and g-terpinene, a-terpineol, terpinene-4-ol cuminyl alcohol, trans-dihydrocarvone (menthane type monoterpenoids), myrcene, linalool (acyclic monoterpenoids), b-caryophyllene, b-farnesene, b-elemene (sesquiterpenoids) et al. were reported as other constituents.2,3) However, only two flavonoid glycosides (7-O-b-D-glucopyranosides of apigenin and luteolin) have been published as constituents of the water-soluble portion of this fruit. 4) In continuation of our studies on the water-soluble constituents of spices, 5) and to show the relationship between the essential oil and the water-soluble constituents, we undertook a detailed investigation of this fruit. In this paper, we discuss the isolation and structural elucidation of monoterpenoid glucosides.Commercial cumin was extracted with 70% methanol, and the methanolic extract was suspended in water and successively extracted with ether and ethyl acetate. The aqueous layer was chromatographed on Amberlite XAD-II to give water and methanol eluate fractions. The methanol eluate fraction (glycoside fraction) was chromatographed on Sephadex LH-20, then subjected to a combination of silica gel, Lobar RP-8 column chromatography and HPLC to isolate sixteen monoterpenoid glucosides (1-16). Among them, twelve glucosides (1-3, 5, 6, 9, 11-16) are new compounds. All new glucosides described in this paper were b-D-glucopyranosides as shown by their 1 H-and 13 C-NMR data (Tables 1 and 2). This was confirmed by hydrolysis to yield D-glucose C-NMR spectral data of 1 (Tables 1, 2) revealed the presence of one 1,4-disubstituted benzene ring, two hydroxymethyls, one sec-methyl and one methine, in addition to the b-glucopyranosyl moiety. From analysis of the heteronuclear multiplet-bond correlation (HMBC) spectral data (correlations: H-2/C-4, C-6, C-7; H-3/C-1, C-2, C-4, C-5, C-8; H-5/C-1, C-3, C-6, C-8; H-6/C-2, C-4, C-7; H 2 -7/C-1, C-2, C-6, Glc C-1; H-8/C-3, C-4, C-5, C-9, C-10; H 2 -9/C-4, C-8, C-10; H 3 -10/C-4, C-8, C-9; Glc H-1/C-7), the aglycone was clarified to be 9-hydroxycuminyl alcohol (p-mentha-1,3,5-triene-7,9-diol), and the location of the glucosyl group was indicated to be C-7. Enzymatic hydrolysis of 1 gave an aglycone (1a; C-NMR spectral data and glycosilaton shift values with those of 1. The result of the HMBC experiment (see experimental) also supported this conclusion. As the optical rotation of (8S)-8,9-dihydroxycuminyl alcohol was reported be plus, 9) the configuration at C-8 of 2 should be S. Therefore, 2 was characterize...