A new stilbene glucoside from the roots of Polygonum multiflorum Thunb

Chungbuk National University, Chinsen, Chungcheongbuk-do, South Korea
Archives of Pharmacal Research (Impact Factor: 2.05). 12/2006; 29(11):946-51. DOI: 10.1007/BF02969276
Source: PubMed


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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Available from: Mingshan Zheng, Aug 04, 2014
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    • "Fourier-transform ion cyclotron resonance (FTICR) MS has been used to determine accurate mass (and elemental composition), of estrogenic compounds [25]. 1H-NMR and 13C- NMR, have been used to elucidate the structure of many polyphenolic components from the genus Fallopia[19,26,27]. However, if the polyphenols contain chiral centers, NMR analysis will only yield the relative stereochemistry of the compound, and it is then necessary to use either X-ray crystallography or optical rotation combined with circular dichroism to determine the absolute stereochemistry [28]. "
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    ABSTRACT: Background The plant genus Fallopia is well-known in Chinese traditional medicine and includes many species that contain bioactive compounds, namely phytoestrogens. Consumption of phytoestrogens may be linked to decreased incidence of breast and prostate cancers therefore discovery of novel phytoestrogens and novel sources of phytoestrogens is of interest. Although phytoestrogen content has been analyzed in the rhizomes of various Fallopia sp., seeds of a Fallopia sp. have never been examined for phytoestrogen presence. Methods Analytical chemistry techniques were used with guidance from an in vitro estrogen receptor bioassay (a stably transfected human ovarian carcinoma cell line) to isolate and identify estrogenic components from seeds of Fallopia convolvulus. A transiently transfected human breast carcinoma cell line was used to characterize the biological activity of the isolated compounds on estrogen receptors (ER) α and β. Results Two compounds, emodin and the novel flavan-3-ol, (−)-epiafzelechin-3-O-p-coumarate (rhodoeosein), were identified to be responsible for estrogenic activity of F. convolvulus seed extract. Absolute stereochemistry of rhodoeosein was determined by 1 and 2D NMR, optical rotation and circular dichroism. Emodin was identified by HPLC/DAD, LC/MS/MS, and FT/ICR-MS. When characterizing the ER specificity in biological activity of rhodoeosein and emodin, rhodoeosein was able to exhibit a four-fold greater relative estrogenic potency (REP) in breast cells transiently-transfected with ERβ as compared to those transfected with ERα, and emodin exhibited a six-fold greater REP in ERβ-transfected breast cells. Cell type-specific differences were observed with rhodoeosein but not emodin; rhodoeosein produced superinduction of reporter gene activity in the human ovarian cell line (> 400% of maximum estradiol [E2] induction) but not in the breast cell line. Conclusion This study is the first to characterize the novel flavan-3-ol compound, rhodoeosein, and its ability to induce estrogenic activity in human cell lines. Rhodoeosein and emodin may have potential therapeutic applications as natural products activating ERβ, and further characterization of rhodoeosein is necessary to evaluate its selectivity as a cell type-specific ER agonist.
    Full-text · Article · Jun 2013 · BMC Complementary and Alternative Medicine
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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.
    Full-text · Article · Sep 2012 · Archives of Pharmacal Research
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    • "FPR5 was also subjected to CC similarly to FPR4 and 93 sub-fractions were collected. Sub-fractions obtained in CH2Cl2-MeOH 10% afforded compound 8 [22]. The chemical structures of the isolated compounds are illustrated in Figure 1. "
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    ABSTRACT: Many plants of the family Moraceae are used in the treatment of infectious diseases. Ficus polita Vahl., an edible plant belonging to this family is used traditionally in case of dyspepsia, infectious diseases, abdominal pains and diarrhea. The present work was designed to assess the antimicrobial activity of the methanol extract from the roots of F. polita (FPR), as well as that of its fractions (FPR1-5) and two of the eight isolated compounds, namely euphol-3-O-cinnamate (1) and (E)-3,5,4'-trihydroxy-stilbene-3,5-O-β-D-diglucopyranoside (8). The liquid microdilution assay was used in the determination of the minimal inhibitory concentration (MIC) and the minimal microbicidal concentration (MMC), against seven bacterial and one fungal species. The results of the MIC determination showed that the crude extract, fractions FPR1, FPR2 and compound 8 were able to prevent the growth of the eight tested microorganisms. Other samples showed selective activity. The lowest MIC value of 64 μg/ml for the crude extract was recorded on 50% of the studied microbial species. The corresponding value for fractions of 32 μg/ml was obtained on Salmonella typhi, Escherichia coli and Candida albicans ATCC strains. The MIC values recorded with compound 8 on the resistant Pseudomonas aeruginosa PA01 strain was equal to that of chloramphenicol used as reference antibiotic. The obtained results highlighted the interesting antimicrobial potency of F. polita as well as that of compound 8, and provided scientific basis for the traditional use of this taxon in the treatment of microbial infections.
    Full-text · Article · Jan 2011 · BMC Complementary and Alternative Medicine
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