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Chemical constituents from the root of Polygonum multiflorum and their soluble epoxide hydrolase inhibitory activity

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Abstract

Fourteen compounds were isolated from a methanol extract of Polygonum multiflorum roots, and their structures were elucidated by comparing spectroscopic data to published spectra. The inhibitory effects of the isolated compounds on soluble epoxide hydrolase (sEH) were then evaluated. Compounds 1–7 inhibited sEH activity potently, with IC50 values ranging from 6.2 ± 0.5 to 48.6 ± 3.1 μM. Moreover, a kinetic analysis of compounds 1–7 revealed that the inhibitory actions of compounds 1, 3 and 4 were non-competitive, whereas those of compounds 2 and 5–7 were mixed-type.

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References

  • Amano, Y., T. Yamaguchi, and E. Tanabe. 2014. Structural insights into binding of inhibitors to soluble epoxide hydrolase gained by fragment screening and X-ray crystallography. Bioorganic & Medicinal Chemistry 22: 2427–2434.

    Article  CAS  Google Scholar 

  • Chen, L.L., X.J. Huang, M.M. Li, G.M. Ou, B.X. Zhao, M.F. Chen, Q.W. Zhang, Y. Wang, and W.C. Ye. 2012. Polygonflavanol A, a novel flavonostilbene glycoside from the roots of Polygonum multiflorum. Phytochemistry Letters 5: 756–760.

    Article  CAS  Google Scholar 

  • Chen, Y., M.F. Wang, R.T. Rosen, and C.T. Ho. 1999. 2,2-Diphenyl-1-picrylhydrazyl radical-scavenging active components from Polygonum multiflorum Thunb. Journal of Agriculture and Food Chemistry 47: 2226–2228.

    Article  CAS  Google Scholar 

  • Cho, J.K., M.J. Curtis-Long, K.H. Lee, D.W. Kim, H.W. Ryu, H.J. Yuk, and K.H. Park. 2013. Geranylated flavonoids displaying SARS-CoV papain-like protease inhibition from the fruits of Paulownia tomentosa. Bioorganic & Medicinal Chemistry 21: 3051–3057.

    Article  CAS  Google Scholar 

  • Imig, J.D., and B.D. Hammock. 2009. Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases. Nature Reviews Drug Discovery 8: 794–805.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Jones, P.D., N.M. Wolf, C. Morisseau, P. Whetstone, B. Hock, and B.D. Hammock. 2005. Fluorescent substrates for soluble epoxide hydrolase and application to inhibition studies. Analytical Biochemistry 343: 66–75.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Kashiwada, Y., G.I. Nonaka, and I. Nishoka. 1986. Tannins and related compounds. XLV. Rhubarb. Isolation and characterization of flavan-3-ol and procyanidin glucosides. Chemical & Pharmaceutical Bulletin 34: 3208–3222.

    Article  CAS  Google Scholar 

  • Kim, H.K., Y.H. Choi, J.S. Choi, S.U. Choi, Y.S. Kim, K.R. Lee, Y.K. Kim, and S.Y. Ryu. 2008. A new stilbene glucoside gallate from the roots of Polygonum multiflorum. Archives of Pharmacal Research 31: 1225–1229.

    Article  CAS  PubMed  Google Scholar 

  • Kim, Y.M., C.H. Lee, H.G. Kim, and H.S. Lee. 2004. Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi. Journal of Agriculture and Food Chemistry 52: 6096–6100.

    Article  CAS  Google Scholar 

  • Kwon, B.M., S.H. Kim, N.I. Baek, S.I. Lee, E.J. Kim, J.H. Yang, B.S. Chae, J.H. Lee, H.W. Park, J.S. Park, and D.K. Kim. 2009. Farnesyl protein transferase inhibitory components of Polygonum multiflorum. Archives of Pharmacal Research 32: 495–499.

    Article  CAS  PubMed  Google Scholar 

  • Lee, G.H., S.J. Oh, S.Y. Lee, J.Y. Lee, J.Y. Ma, Y.H. Kim, and S.K. Kim. 2014. Discovery of soluble epoxide hydrolase inhibitors from natural products. Food and Chemical Toxicology 64: 225–230.

    Article  CAS  PubMed  Google Scholar 

  • Lin, H.W., M.X. Sun, Y.H. Wang, L.M. Yang, Y.R. Yang, N. Huang, L.J. Xuan, Y.M. Xu, D.L. Bai, Y.T. Zheng, and K. Xiao. 2010. Anti-HIV activities of the compounds isolated from Polygonum cuspidatum and P. multiflorum. Planta Medica 76: 889–892.

    Article  CAS  PubMed  Google Scholar 

  • Liu, J.Y., S.H. Park, C. Morisseau, S.H. Hwang, B.D. Hammock, and R.H. Weiss. 2009. Sorafenib has soluble epoxide hydrolase inhibitory activity, which contributes to its effect profile in vivo. Molecular Cancer Therapeutics 8: 2193–2203.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Luyen, B.T.T., B.H. Tai, N.P. Thao, J.E. Kim, J.Y. Cha, M.J. Xin, Y.M. Lee, and Y.H. Kim. 2014. Anti-inflammatory components of Euphorbia humifusa Willd. Bioorganic & Medicinal Chemistry Letters 24: 1895–1900.

    Article  CAS  Google Scholar 

  • Lv, L.S., X.H. Gu, J. Tang, and C.T. Ho. 2007. Antioxidant activity of stilbene glycoside from Polygonum multiflorum Thunb in vivo. Food Chemistry 104: 1678–1681.

    Article  CAS  Google Scholar 

  • Ma, J., H. Yang, M.J. Basile, and E.J. Kennelly. 2004. Analysis of polyphenolic antioxidants from the fruits of three Pouteria species by selected ion monitoring liquid chromatography-mass spectrometry. Journal of Agriculture and Food Chemistry 52: 5873–5878.

    Article  CAS  Google Scholar 

  • Moser, D., J. Achenbach, F.M. Klingler, B. Estella, S. Hahn, and E. Proschak. 2012. Evaluation of structure-derived pharmacophore of soluble epoxide hydrolase inhibitors by virtual screening. Bioorganic & Medicinal Chemistry Letters 22: 6762–6765.

    Article  CAS  Google Scholar 

  • Newman, J.W., C. Morisseau, and B.D. Hammock. 2005. Epoxide hydrolases: their roles and interactions with lipid metabolism. Progress in Lipid Research 44: 1–51.

    Article  CAS  PubMed  Google Scholar 

  • Pacifici, G.M., A. Temellini, L. Giuliani, A. Rane, H. Thomas, and F. Oesch. 1988. Cytosolic epoxide hydrolase in humans: development and tissue distribution. Archives of Toxicology 62: 254–257.

    Article  CAS  PubMed  Google Scholar 

  • Pillarisetti, S., and I. Khanna. 2012. Targeting soluble epoxide hydrolase for inflammation and pain—an overview of pharmacology and the inhibitors. Inflammation & Allergy 11: 143–158.

    Article  CAS  Google Scholar 

  • Qi, H.Y., C.F. Zhang, and M. Zhang. 2005. Three new anthraquinones from Polygonum cillinerve. Chinese Chemical Letters 16: 1050–1052.

    CAS  Google Scholar 

  • Shen, H.C., and B.D.J. Hammock. 2012. Discovery of inhibitors of soluble epoxide hydrolase: a target with multiple potential therapeutic indications. Medicinal Chemistry 55: 1789–1808.

    Article  CAS  Google Scholar 

  • Spector, A.A., X. Fang, G.D. Snyder, and N.L. Weintraub. 2004. Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function. Progress in Lipid Research 43: 55–90.

    Article  CAS  PubMed  Google Scholar 

  • Sun, Y.N., L. Cui, W. Li, X.T. Yan, S.Y. Yang, J.I. Kang, H.K. Kang, and Y.H. Kim. 2013. Promotion effect of constituents from the root of Polygonum multiflorum on hair growth. Bioorganic & Medicinal Chemistry Letters 23: 4801–4805.

    Article  CAS  Google Scholar 

  • Thiruvengadam, M., N. Praveen, E.H. Kim, S.H. Kim, and I.M. Chung. 2014. Production of anthraquinones, phenolic compounds and biological activities from hairy root cultures of Polygonum multiflorum Thunb. Protoplasma 251: 555–566.

    Article  CAS  PubMed  Google Scholar 

  • Wang, M.J., R.H. Zhao, W.G. Wang, X.J. Mao, and J. Yu. 2012. Lipid regulation effects of Polygoni multiflori radix, its processed products and its major substances on steatosis human liver cell line L02. Journal of Ethnopharmacology 139: 287–293.

    Article  CAS  PubMed  Google Scholar 

  • Wang, Y., M.J. Curtis-Long, H.J. Yuk, D.W. Kim, X.F. Tan, and K.H. Park. 2013. Bacterial neuraminidase inhibitory effects of prenylated isoflavones from roots of Flemingia philippinensis. Bioorganic & Medicinal Chemistry 21: 6398–6404.

    Article  CAS  Google Scholar 

  • Zhang, H., Z.J. Guo, N. Wu, W.M. Xu, L. Han, N. Li, and Y.X. Han. 2012. Two novel naphthalene glucosides and an anthraquinone isolated from Rumex dentatus and their antiproliferation activities in four cell lines. Molecules 17: 843–850.

    Article  CAS  PubMed  Google Scholar 

  • Zhang, Y.Z., J.F. Shen, J.Y. Xu, J.H. Xiao, and J.L. Wang. 2007. Inhibitory effects of 2,3,5,4′-tetrahydroxystilbene-2-O-β-d-glucoside on experimental inflammation and cyclooxygenase 2 activity. Journal of Asian Natural Products Research 9: 355–363.

    Article  PubMed  Google Scholar 

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Acknowledgments

This study was supported by the Priority Research Center Program (2009–0093815) through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology, Republic of Korea.

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Authors and Affiliations

  1. College of Pharmacy, Chungnam National University, Daejeon, 305-764, Korea

    Ya Nan Sun, Jang Hoon Kim, Xi Tao Yan, Ji Eun Kim, Seo Young Yang & Young Ho Kim

  2. School of Biotechnology, Yeungnam University, Gyeongsan, 712-749, Gyeongbuk, Korea

    Wei Li

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  1. Ya Nan Sun
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  2. Wei Li
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  3. Jang Hoon Kim
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  4. Xi Tao Yan
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  5. Ji Eun Kim
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  7. Young Ho Kim
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Correspondence to Young Ho Kim.

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Ya Nan Sun and Wei Li have contributed equally to this work.

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Sun, Y.N., Li, W., Kim, J.H. et al. Chemical constituents from the root of Polygonum multiflorum and their soluble epoxide hydrolase inhibitory activity. Arch. Pharm. Res. 38, 998–1004 (2015). https://doi.org/10.1007/s12272-014-0520-4

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  • DOI: https://doi.org/10.1007/s12272-014-0520-4

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