Chem. Pharm. Bull. 53(1) 110—113 (2005)

Zhejiang provinces of China. The roots of this plant are used as a remedy for icterus and arthritis in Chinese folk medicine. Hitherto, no chemical constituents or bioactivities of this plant have been reported. In the course of our search for active components from this plant, three new phenolics, (1S,2R)-1-(4 -O-b -D-glucopyranosyl-3 -methoxyphenyl)-2(4 -hydroxy-3 -methoxyphenyl)-1,3-propanediol (1), a lignan named symplolignanoside A (2), and 3,4-dimethoxyphenol b-D-apiofuranosyl(1→6)-b-D-glucopyranoside (3), along with eight known compounds, dihydrodehydrodiconiferyl alcohol 4 -O-b-D-glucoside (4), 7,9,9 -trihydroxy-3,3 dimethoxy-8-O-4 -neolignan-4-O-b-D-glucopyranoside (5), kelampayoside A (6), 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-1,3-propanediol 1-O-glucoside (7), b-daucosterol (8), glucose (9), sucrose (10), and inositol (11), were isolated from the roots of this plant. Their structures were elucidated by spectroscopic and chemical methods. Compound 1 was obtained as a white powder, [a]D 24.6°. The IR spectrum of 1 showed the presence of hydroxyl groups (3392, 3361 cm ) and aromatic rings (1616, 1581 cm ). The UV spectrum also showed the presence of aromatic rings (206, 279 nm). High resolution (HR)-FABMS (positive) gave a quasimolecular ion [M Na] at m/z 505.1664 (Calcd 505.1686), indicating a molecular formula of C23H30O11. In the H-NMR spectrum of 1 (Table 1), two sets of ABX-type signals at dH 7.54 (1H, d, J 8.0 Hz), 7.25 (1H, d, J 1.0 Hz), and 7.17 (1H, dd, J 8.0, 1.0 Hz) and at dH 7.26 (1H, d, J 1.0 Hz), 7.16 (1H, d, J 8.0 Hz), and 7.13 (1H, dd, J 8.0, 1.0 Hz) were observed, which suggested the existence of two 1,3,4-trisubstituted benzene rings. Additionally, two aromatic methoxy signals at dH 3.64 (3H, s) and 3.59 (3H, s), and an anomeric proton signal at dH 5.62 (1H, d, J 7.0 Hz) were demonstrated. The C-NMR spectrum (Table 1) showed 23 carbon signals. Except for 12 aromatic carbons, six saccharide moiety carbons, and two methoxy signals, the C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra showed one oxygenated methine signal at dC 74.7 (C-1), one methine signal at dC 57.4 (C-2), and one oxygenated methylene signal at dC 65.0 (C-3). These signals were suggestive of the presence of the 1,3-propanediol moiety. This was further supported by the heteronuclear multiple bond connectivity (HMBC) experiment (Fig. 1). In the HMBC spectrum, the correlation peaks of H-2/C-1 , C-2 , C-6 ; H-1/C-2 , C-6 , C-1 ; and CH3O–/C-3 , C-3 indicated that two benzene rings were linked to the C-1 and C-2 of the 1,3-propanediol fragment and two methoxyl groups were located at the C-3 and C-3 in two benzene rings, respectively. The correlation of H-1 with the C-4 at dC 147.2 in the HMBC spectrum and an enhancement of the proton signal at the H-5 on irradiation of the H-1 in the nuclear Overhauser effect (NOE) experiment revealed that the saccharide moiety was attached to the C-4 . The anomeric proton signal at dH 5.62 (1H, d, J 7.0 Hz, H1 ) in the H-NMR spectrum and six sugar carbon signals at dC 102.9 (C-1 ), 75.4 (C-2 ), 79.0 (C-3 ), 71.6 (C-4 ), 79.2 (C-5 ) and 62.8 (C-6 ) demonstrated that the sugar was b-Dglucose. Furthermore, enzymatic hydrolysis of 1 gave 1a and glucose. Glucose was identified by TLC comparing with an authentic sample. The erythro relative configuration at the C1 and C-2 in 1 was suggested by comparing the NMR spectra with those of erythro and threo isomers. The absolute con110 Notes Chem. Pharm. Bull. 53(1) 110—113 (2005) Vol. 53, No. 1