Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

The Radical Scavenging Effects of Stilbene Glucosides from Polygonum multiflorum

  • Ryu, Geon-Seek (Regional Research Center and Department of Chemical Technology, Hanbat National University) ;
  • Ju, Jeung-Hoon (Regional Research Center and Department of Chemical Technology, Hanbat National University) ;
  • Park, Yong-Ju (Livechem, INC., Hanbat National University) ;
  • Ryu, Shi-Yong (Korea Research Institute of Chemical Technology) ;
  • Choi, Byoung-Wook (Korea Research Institute of Chemical Technology) ;
  • Lee, Bong-Ho (Regional Research Center and Department of Chemical Technology, Hanbat National University)
  • Published : 2002.10.01
Download PDF
⟨ Previous Next ⟩

Abstract

The extract of the root of Polygonum multiflorum exhibited a significant antioxidant activity assessed by the DPPH radical scavenging activity in vitro. The bioassay-guided fractionation of the extract yielded a stilbene glucoside, (E)-2,3,5,4'-tetrahydroxystilbene-2-Ο-$\beta$-d-glucopyranoside (1) as an active constituent responsible for the antioxidant property. Compound 1 demonstrated a moderate DPPH radical scavenging activity ($IC_{50}$, 40 $\mu$M), while the corresponding deglucosylated stilbene 2 exhibited a much higher activity ($IC_{50}$, 0.38 $\mu$M).

Keywords

References

  1. Aue, W P., Bartholdi, E., Ernst, R R, Two dimensional spectroscopy. Application to nuclear magnetic resonance, J. Chem. Phys., 64, 2229-2246 (1976) https://doi.org/10.1063/1.432450
  2. Bax, A; Subramanian, S., Sensitivity-enhanced four-dimensional hetero nuclear shift correlation NMR spectroscopy, J. Magn. Res., 67, 565-569 (1986)
  3. Bax, A, Summer, M. F, Proton and carbon-13 assignments from multiple-bond connectivity by 2D multiple quantum NMR, J. Am. Chem. Soc., 108, 2093-2094 (1986) https://doi.org/10.1021/ja00268a061
  4. Bouchet, N., Barrier, L., Fauconneau, B., Radical scavenging activity and antioxidant properties of tannins from Guiera senegalensis (Combretaceae), Phytother. Res., 12, 159-162 (1998) https://doi.org/10.1002/(SICI)1099-1573(199805)12:3<159::AID-PTR209>3.0.CO;2-C
  5. Chen, C.-C., Wu, L.-G., Ko, F.-N., Teng, C.-M., Antiplatelet aggregation principles of Dendrobium loddigesii, J. Nat. Prod., 57, 1271-1274 (1994) https://doi.org/10.1021/np50111a014
  6. Chen, J. H., Ho, C.-T., Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds, J. Agric. Food Chem., 45, 2374-2378 (1997) https://doi.org/10.1021/jf970055t
  7. Frankel, E. N., Waterhouse, A L., Kinsella, J. E., Inhibition of human LDL oxidation by resveratrol, Lancet, 341, 1103-1104 (1993)
  8. Geahlen, R. L., Piceatannol(3,4,3',5'-tetahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor, Biochem. Biophys. Res. Commmun., 165, 241-245 (1989) https://doi.org/10.1016/0006-291X(89)91060-7
  9. Goldberg, D. M., Does wine work, Clini. Chem., 41, 14-16 (1995)
  10. Hata, K., Kozawa, M., Baba, K., New stilbene glucose Chinese crude drug Heshouwu root of Poloygonum multiflorm, Yakugaku Zasshi, 95, 211-213 (1975) https://doi.org/10.1248/yakushi1947.95.2_211
  11. Inamori, Y, Kubo, M., Tsujibo, H., Ogawa, M., Saito, Y, Miki, Y, Takemura, S., The ichthyotoxicity and cornary vasodilator action of 3,3'-diethylstilbene, Chem. Pharm. Bull., 35, 887-890 (1989)
  12. Jang, M., Cai, L., Udeani, G. O., Slowing, K. V., Thomas, C. F, Beecher,C.W. W, Fong, H. S., Farnsworth, N. R, Kinghorn, A D., Mehta, R G., Moon, R C., Pezzuto, J. M., Cancer chemopreventive activity of resveratrol, a natural product derived from grapes, Science, 275, 218-220 (1997) https://doi.org/10.1126/science.275.5297.218
  13. Jayatilake, G. S., Jayasuriya, H., Lee, E.-S., Koonchanok, N. M., Geahlen, R L., Ashendel, C. L., McLaughlin, J. L., Chang., C. J., Kinase inhibitors from Polygonum cuspidatum, J. Nat. Prod., 56, 1805-1810 (1993) https://doi.org/10.1021/np50100a021
  14. Langcake, P, Corngird, C. A, Pryce, R. J., Identification of pterostilbene as pyhtoalexin from Vitis vinifera leaves, Phytochem., 18, 1025-1027 (1979) https://doi.org/10.1016/S0031-9422(00)91470-5
  15. Mannila, E., Talvitie, A., Kolehmainen, E., Antileukemic compounds derived from stilbene in Picea abies bark, Phytochem., 33, 813-816 (1993) https://doi.org/10.1016/0031-9422(93)85280-5
  16. Mattivi, F, Reniero, F, Korhammer, S., Isolation, characterization, and evolution in red wine vinification of resveratrol monomers, J. Agric. Food Chem., 43, 1820-1823 (1995) https://doi.org/10.1021/jf00055a013
  17. Murakami, S., Arai, I., Muramatsu, M., Otomo, S., Baba, K., Kido, T., Kozawa, M., Effect of stilbene derivatives on gastric $H^{+}$, $K^{(+)}$-ATPase., Biochem. Pharmacol., 44, 1947-1951 (1992) https://doi.org/10.1016/0006-2952(92)90096-2
  18. Nyemba, AM., Mpondo, N. T, Kimbu, S. F., Connolly, J. D., Stilbene glycosides from Guibourtia tessmannii, Phytochem., 39, 895-898 (1995) https://doi.org/10.1016/0031-9422(94)00915-G
  19. Oliver, J. M., Burg, D. L., Wilson, B. S., McLaughlin, J. I., Inhibition of mast cell Fc- $\epsilon$-R1-mediated signaling and effector function by the SYK-selective inhibitor, piceatannol, J. Biol. Chem., 269, 29697-29703 (1994)
  20. Orsini, F., Pelizzoni, F., Verotta, L., Aburjai, T, Rogers, C. B., Isolation, synthesis, and antiplatelet aggregation activity of resveratrol 3-O-$\beta$-D-glucopyranoside and related compounds, J. Nat. Prod., 60, 1082-1087 (1997) https://doi.org/10.1021/np970069t
  21. Pietta, P, Simonetti, P, Mauri, P, Antioxidant activity of selected medicinal plants, J. Agric. Food Chem., 46, 4487-4490 (1998) https://doi.org/10.1021/jf980310p
  22. Rice-Evans, C. A, Miller, N. J., Bolwell, P G., Brmaley, PM., Prdharn, J. B., The relative antioxidant activity of plant-derived poiyphenolic flavonids, Free Rad. Res., 22, 375-383 (1995) https://doi.org/10.3109/10715769509145649
  23. Ryu,G,, Park, E. K., Joo, J. H., Lee, B. H., Choi, B. W, Jung, D. S. I_ee, N. H., A New antioxidant monoterpene glycoside, $\acute{a}$-benzoyloxypaeoniflorin from Paeonia suffruticosa, , Arch. Pharm. Res., 24, 105-108 (2001) https://doi.org/10.1007/BF02976476
  24. Ryu, S. Y, Han, Y N., Han B. H., Monoamine oxidase-A inhibitors from medicinal plants, Arch. Pharm. Res., 11, 230-239 (1988) https://doi.org/10.1007/BF02861314
  25. Teguo, P. W, Decendit, A, Vercauteren, J., Deffieux, G., Merillon, J. M., Trans- resreratrol-3-O-$\beta$-glucose (piceid) in cell suspension cultures of Vitis vinifera, Phytochem., 42, 1591-1593 (1996) https://doi.org/10.1016/0031-9422(96)00203-8
  26. Teguo, P. W, Decendit, A, Krisa, S., Vercauteren, J., Deffieux, G., Merillon, J. M., The accumulation of stilbene glycosides in Vitis vinifera cell suspension cultures of Vitis vinifera, J. Nat. Prod., 59, 1189-1191 (1996) https://doi.org/10.1021/np9605450
  27. Teguo, P. W, Deffieux, G., Vercauteren, J., Merillon, J. M., Isolation, identificaion, and antioxidant activity of three stilbene glucosides newly extracted from Vitis vinifera cell cultures, J. Nat. Prod., 61, 655-657 (1998) https://doi.org/10.1021/np9704819
  28. Thakkar, K., Geahlen, R. L., Cushman, M., Synthesis and protein-tyrosine kinase inhibitory activity of polyhyroxylated stilbene analogs of piceatannol, J. Med. Chem., 36, 2950-2955 (1993) https://doi.org/10.1021/jm00072a015
  29. Verotta, L., Rogers, B. C., Aburjai, T, Cignarella, A, Colli, S., Puglisi, L., Giornate di Chimica delle Sostanze Naturali, Ⅲ convegno Nazionale, Amalfi (SA) 29 maggio-1 giugno, 3 (1994)