A new lignan glycoside, aviculin [1], was isolated from the whole plant of Polygonum avtculare along with the known compounds juglanin [2], avicularin [3], astragalin [4], and betmidin [5]. The structure of the new compound was elucidated on the basis of spectroscopic and chemical evidence.Polygonum avtculare L. (Polygonaceae) is a medicinal plant frequently employed in Korean traditional medicine. The whole plant has been used as an antipyretic, antiparasitic, and diuretic agent (1,2). This paper deals with the structural elucidation of a new lignan glycoside, aviculin [1], and the isolation from this plant of four flavonoid glycosides (3-5), juglanin [2], avicularin [3], astragalin [4], and betmidin [5]. RESULTS AND DISCUSSIONThe EtOAc-soluble fraction of the aqueous MeOH extract afforded 1, C26H34O10, amorphous powder, mp 155-157°, [a]25D +20.27°( ¿=0.074, MeOH). On acetylation with Ac20 and pyridine, compound 1 afforded a hexaacetate [la], as an oily compound (6).Acidic hydrolysis of compound 1 yielded L-rhamnose and an aglycone having identical specific rotation and eims data with those of (+)-isolariciresinol [lb] (7). The cd of the aglycone was a mirror image to that of ( -)-isolariciresinol (8), with known absolute configuration (9), and also in agreement with published cd data of (+)isolariciresinol dimethyl ether (10). The eims spectrum of compound 1 showed a molecular ion peak at miz 506, besides significant fragment peaks at mlz 359 [M-rhamnose]+, 341 [M-rhamnose-H20]+, 311 [M-rhamnose-H20-OCHJ+,

Bioassay-directed chromatographic fractionation of an ethyl acetate extract of the leaves of Acer okamotoanum using HIV-1 integrase afforded a new acylated flavonol glycoside, quercetin 3-O-(2",6"-O-digalloyl)-beta-D-galactopyranoside (1), together with six known flavonol glycosides and three known phenolic compounds. The structure of the new compound was determined by spectroscopic methods. The most active compounds were quercetin 3-O-(2"-galloyl)-alpha-L-arabinopyranoside (6) and 1, which exhibited IC50 values of 18.1 +/- 1.3 and 24.2 +/- 6.6 micrograms/mL, respectively, against HIV-1 integrase.

A new prenylated flavonol, sophoflavescenol (1), together with five known flavonoids, kurarinol, kushenol K, kushenol H, trifolirhizin, and kuraidin, were isolated from the roots of Sophora flavescens. The structure of 1 was determined by spectroscopic analysis. Among the five known flavonoids, kurarinol, kushenol K, and kushenol H showed weak antiviral activity against Herpes simplex virus types I and II.

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