Antioxidative Activity of Urushiol Derivatives from the Sap of Lacquer Tree (Rhus vernicifera Stokes)

  • ///
  • Published : 1997.09.01

Abstract

The authors isolated four olefinic catechols, commonly referred to as urushiol, from the sap of Korean lacquer tree(Rhus vernicifera STOKES) with stronger antioxidative activities than $\alpha-tocopherol$. The hexane extract with a free radical scavenging activity was purified by silica and ODS gel column chromatography. The active compounds were identified by MS and $^1H-NMR$ as 3-[8'(Z),11'(Z),14'-pentadecatrienyl]catechol, 3-[8'(Z),11'(Z)-pentadecadienyl]catechol, 3-[8'(Z)-pentadecenyl] catechol, and 3-pentadecylcatechol. All of these compounds showed strong free radical scavenging activities on 1,1-diphenyl-2-picrylhydrazyl(DPPH) radical, in which 3-pentadecylacatechol exhibited the highest activity ($IC_{50}$: $1.2{\mu}g/ml$). They also showed a significant inhibitory activity on lipid peroxidation ($IC_{50}$: 2.1 - 3.5 ${\mu}g/ml$). The antioxidative activity of 3-pentadecylcatechol on DPPH radical and lipid peroxidation is approximately two times greater than that of $\alpha$-tocopherol. The results suggest that the urushiol derivatices may contribute to the preservative characteristics effective against oxidative stress and could be a good source for industrial applications including a coating material.

Keywords

References

  1. In Urushi: Elegant Asia Onishi, N.
  2. Chem. Soc. Rev. v.8 Non-isoprenoid long chain phenols Tyman, J. H. P.
  3. Chem. Ber. v.55B ber den Hauptbestandteil des Japan lacks. VIII. Mitteilung: Stellung der Doppelbindungen in der Seitenkette des Urushiols und Bewcish hrung, da das Urushiol eine Mischung ist. Majima, R.
  4. J. Org. Chem. v.30 On the isolation of the allergenically active components of the toxic principle of poison ivy Markiewitz, K. H.;C.R. Dawson
  5. Am. Chem. Soc. v.56 The toxic principle of the poison ivy Hill, G. A.;V. Mattacotti;W. D. Graham
  6. Phytochemistry v.22 An urushiol derivative from poison sumac Adawadkar, P.D.;M. A. Elsohly
  7. Biol. Pharm. Bull. v.19 Antioxidative effects of phenylethanoids from Cistanche deserticola Xiong, Q.;S. Kadota;T. Tadata;T. Namba
  8. J. Antibiotics v.49 Benzastatins A, B, C, and D: New free radical scavengers from Streptomyces nitrosporeus 30643. I. Taxonomy, fermentation, isolation, physicochemical properties and biological activities Kim, W. G.;J. P. Kim;C. J. Kim;K. H. Lee;I. D. Yoo
  9. Anal. Biochem. v.95 Assay for lipid peroxides in animal tissues by thiobarbituric acid reastion Ohkawa, H.;N. Ohishi;K. Yagi
  10. Rhusvernicifera. J. Chromatog. v.284 Reversed-phase liquid chromatographic separation and identification of constituents of urushiol in the sap of the lac tree Du, Y.;R. Oshima;J. Kumanotani
  11. J. Chromatog. v.243 Configuration of the olefinic bonds in the heteroolefinic side-chains of Japanese lacquer urushiol Yamauchi, Y.;R. Oshima;J. Kumanotani
  12. J. Nat. Prod. v.45 Separation and characterization of poison ivy and poison oak urushiol components ElSohly, M. A.;Adawadkar, P. D.;C. Y. Ma;C. E. Turner
  13. Res. Rept. RDA v.33 The characteristics of allegic materials from Korean lacquer tree sap:Treperative analysis of lacquer tree sap Jung, D. K.;H. K. Song;H. Kim
  14. Oxygen Radicals in Biological Systems: Oxygen Radicals and Antioxidants Packer, L;A. N. Glazer