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A new stilbene glucoside from the roots of Polygonum multiflorum Thunb.

College of Pharmacy, Yeungnam University, Gyongsan, 712-749, Korea.
Archives of Pharmacal Research (Impact Factor: 1.75). 12/2006; 29(11):946-51. DOI: 10.1007/BF02969276
Source: PubMed

ABSTRACT One new stilbene glucoside (6), along with five known compounds (1-5), were isolated from the roots of Polygonum multiflorum Thumb., and their chemical structures established based on physicochemical and spectroscopic data. Of the compounds, compound 3 showed DNA topoisomerase I and II inhibitory activities.

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    • "Compounds 3, 4, 5, 6 and 7 showed more potent inhibitory activities toward DNA topoisomerase II (IC 50 : 0.54 µM, 14 µM, 15 µM, 0.77 µM and 3 µM, respectively) than that of the positive control, etoposide (IC 50 : 44 µM) (Fig. 3, Table II). Inhibitory activities against topoisomerases I and/or II of compounds 1, 6 and 7 have been reported previously (Jang et al., 1997; Xu et al., 2006; Yamada et al., 2006). However, the inhibitory activities against topoisomerases I and II of compounds 3, 4 and 5 are novel findings. "
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    ABSTRACT: Three anthraquinones (1, 2 and 4), three stilbenes (5, 6 and 7) and 3,5-dihydroxybenzyl alcohol (3) were isolated from Reynoutria japonica. Their structures were identified as emodin (1), emodin-8-O-β-D-glucoside (2), 3,5-dihydroxybenzyl alcohol (3), citreorosein (4), cis-resveratrol (5), trans-resveratrol (6) and trans-resveratrol-5-O-β-D-glucopyranoside (7) by comparing their physicochemical and spectral data with published data. Compound 3 was isolated for the first time from the Polygonaceae family. Among the purified compounds, 3 showed more potent inhibitory activity against topoisomerase I (IC(50): 4 μM) than camptothecin, as the positive control (IC(50): 18 μM). Compounds 3, 4, 5, 6 and 7 showed stronger inhibitory activities toward DNA topoisomerase II (IC(50): 0.54, 14, 15, 0.77 and 3 μM, respectively) than the positive control, etoposide (IC(50): 44 μM). Compounds 1 and 4 displayed weak cytotoxicities against human lung cancer (A549), ovarian cancer (SK-OV-3), human liver hepatoblastoma (HepG2) and colon adenocarcinoma (HT-29) cell lines.
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    • "However, this is the first report on the isolation of compound 1 from this species or from any other plant species. Other isolated components (2~9) from the extract were identified as (E)-2,3,4',5-tetrahydroxystilbene-2-β-D-(2''- galloyl)-glucoside (2) (Nonaka et al., 1982), (E)-2,3,4',5- tetrahydroxystilbene-2-β-D-glucoside (3) (Chen et al., 1999, Yao et al., 2006), (Z)-2,3,4',5-tetrahydroxystilbene-2- β-D-glucoside (4) (Xu et al., 2006), physcion (5) (Kalidhar, 1989), emodin (6) (Francis et al., 1998), torachrysone-8- O-β-D-glucoside (7) (Masahiko et al., 1977, Yi et al., 2005), emodin-8-O-β-D-glucoside (8) (Takeshi and Yutaka, 1987), and physcion-8-O-β-D-glucoside (9) (Takeshi and Yutaka, 1987) by comparison of spectral data with the literature. Both 1 and 2 dose-dependently inhibited purified acetylcholinesterase (AChE) from electric eel in vitro, whereas 3 showed weaker inhibition. "
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    ABSTRACT: A new stilbenoid (1) was isolated from the root extract of Polygonum multiflorum together with eight known constituents (2-9). The chemical structure of 1 was established as the 6''-O-monogalloyl ester of (E)-2,3,4',5-beta-tetrahydroxystilbene-2-beta-D-glucopyranoside based on physicochemical and spectroscopic analyses, particularly by NMR spectroscopic data, i.e., COSY, HMQC and HMBC. Compound 1 weakly inhibited acetylcholinesterase in vitro.
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    ABSTRACT: As part of efforts to discover phytochemicals that inhibit melanin biosynthesis, we screened (E)-2,3,5,4′-tetrahydroxystilbene-2-O-β-D-glucoside (THSG) isolated from Polygonum multiflorum. THSG dose-dependently inhibited tyrosinase activity, with an ID50 value of 100 μg/mL. THSG also potently inhibited melanin production in B16 melanoma cells induced by forskolin, an inducer of melanogenesis, with ID50 of 1–10 μg/mL. THSG may therefore reduce melanogenesis.
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