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: 1.54). 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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    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) alpha and beta. 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 ERbeta as compared to those transfected with ERalpha, and emodin exhibited a six-fold greater REP in ERbeta-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 ERbeta, and further characterization of rhodoeosein is necessary to evaluate its selectivity as a cell type-specific ER agonist.
    BMC Complementary and Alternative Medicine 06/2013; 13(1):133. · 2.08 Impact Factor
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    ABSTRACT: A novel, rapid and specific ultra performance liquid chromatography-photo diode array detection method was developed for the simultaneous determination of 2,3,5,4′-tetrahydroxystilbene-2-O-β-d-glucoside (TSG), emodin-8-O-β-d-glucoside (EMG), emodin (EM) and physcion (PS). The chromatographic separation was performed on an Acquity BEH C18 column (100×2.1mm i.d., 1.7μm). The mobile phase was a mixture of 0.3% acetic acid–water and 0.3% acetic acid–acetonitrile employing gradient elution at the flow rate of 0.4mLmin−1. The four compounds behaved linearly in the concentration range between 60.80–3040.00μgmL−1 (TSG), 0.50–25.00μgmL−1 (EMG), 2.16–108.00μgmL−1 (EM) and 1.56–78.00μgmL−1 (PS), respectively with correlation coefficients >0.999. The precision of the method were below 5% RSD. Recoveries of the four compounds ranged from 95.71 to 102.97%, with RSD values less than 2%.
    Chromatographia 01/2009; 70(3):657-659. · 1.44 Impact Factor
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    ABSTRACT: Five new stilbene glycosides (1-5), together with six known ones, were isolated from the roots of Polygonum multiflorum. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence.
    Journal of Asian natural products research 11/2013; · 0.61 Impact Factor


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