1,1-Diphenyl-2-picrylhydrazyl Radical Scavenging Compounds of Fraxini Cortex

  • Published : 2005.09.01

Abstract

The radical scavenging effect of the MeOH extract of Fraxini Cortex on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical was examined. The $CH_2Cl_2$-and n-BuOH-soluble fractions of MeOH extract showed the promising DPPH radical scavenging effects, and further purified by silica gel, Sephadex LH-20 column chromatography, and reversed-phase C-18 MPLC to yield five coumarins, esculetin (1), fraxidin (2), fraxetin (3), fraxidin $8-O-{\beta}-D-glucopyranoside$ (fraxin methyl ether) (5), esculin (6), and a secoiridoid oleuropein (4), and a coumarin-secoiridoid escuside (7). Compounds 1, 3, and 4 showed potent DPPH radical scavenging effects, exhibiting $IC_{50}$ values of 14.68, 9.64, and $22.03\;{\mu}M$, respectively. Compounds 6 and 7 also showed moderate effects with $IC_{50}$ values of 147.79 and $72.73\;{\mu}M$, respectively. L-Ascorbic acid was used as a positive control and exhibited the $IC_{50}$ value of $50.31\;{\mu}M$.

Keywords

References

  1. Chang, W.S., Lin, C.C., Chuang, S.C., and Chiang, H.C., Superoxide anion scavenging effect of coumarins. Am. J. Chin. Med. 24, 11-17 (1996) https://doi.org/10.1142/S0192415X96000037
  2. Damtoft, S., Franzyk, H., and Jensen, R., Excelsioside, a secoiridoid glucoside from Fraxinus excelsior. Phytochemistry 31, 4197-4201 (1992) https://doi.org/10.1016/0031-9422(92)80442-H
  3. Hahn, D.R., Kim, C.J., Kim, J.H., and Hong, S.K., Coumarin glycoside of Fraxinus chiisanensis. Kor. J. Pharmacogn. 7, 195-198 (1976)
  4. Hahn, D.R. and Lee, M.W., Coumarin glycoside from the stem bark of Fraxinus sieboldiana var. angustata. Kor. J. Pharmacogn. 14, 1-3 (1983)
  5. Halliwell, B., Free radicals, antioxidants and human disease: curiosity, cause or consequence? Lancet 344, 721-724 (1994) https://doi.org/10.1016/S0140-6736(94)92211-X
  6. Inoue, K., Nishioka, T., Tanahashi, T., and Inouye, H., Three secoiridoid glucosides from Ligustrum japonicum. Phytochemistry 21, 2305-2311 (1982) https://doi.org/10.1016/0031-9422(82)85196-0
  7. lossifova, T., Vogler, B., and Kostova, I., Escuside, a new coumarin-secoiridoid from Fraxinus ornus bark. Fitoterapia 73, 386-389 (2002) https://doi.org/10.1016/S0367-326X(02)00132-6
  8. Kappus, H., Lipid peroxidation: mechanisms, enzymology and biological relevance, in Sies II (ed.), Oxidation Stress, Academic Press, London, 1985, pp. 273-310
  9. Kim, N.Y., Pae, H.O., Ko, Y.S., Yoo, J.C., Choi, B.M., Jun, C.D., Chung, H.T., Inagaki, M., Higuchi, R., and Kim, Y.C., In vitro inducible nitric oxide synthesis inhibitory active constituents from Fraxinus rhynchophylla. Planta Med 65, 656-658 (1999) https://doi.org/10.1055/s-2006-960840
  10. Kodaira, H., Ishikawa, M., Komoda, Y., and Nakajima, T., Isolation and identification of anti-platelet aggregation principles from the bark of Fraxinus japonica Blume. Chem. Pharm. Bull. 31, 2262-2268 (1983) https://doi.org/10.1248/cpb.31.2262
  11. Kostova, L.N., Nikolov, N.M., and Chipilska, L.N., Antimicrobial properties of some hydroxycoumarins and Fraxinus ornus bark extracts. J. Ethnopharmacol. 39, 205-208 (1993) https://doi.org/10.1016/0378-8741(93)90037-6
  12. Kumar, V.P., Shashidhara, S., Kumar, M.M., and Sridhara, B.Y., Effect of Luffa echinata on lipid peroxidation and free radical scavenging activity. J. Pharm. Pharmacol. 52, 891-894 (2000) https://doi.org/10.1211/0022357001774589
  13. Kwon, Y.S. and Kim, C.M., A study on the chemical constituents from leaves of Fraxinus rhynchophylla. Kor. J. Pharmacogn. 27, 347-349 (1996)
  14. Matsubara, N., Fuchimoto, S., Iwagaki, H., Nonaka, K., Kimura, T., Kashino, H., Edamatsu, R., Hirarnatsu, M., and Orita, K., The possible involvement of free radical scavenging properties in the actions of cytokines. Res. Commun. Chem. Pathol. Pharmacol. 71, 239-242 (1991)
  15. Razdan, T.K., Qadri, B., Harkar, S., and Waight, E.S., Chromones and coumarins from Skimmia laureola. Phytochemistry 26, 2063-2069 (1987) https://doi.org/10.1016/S0031-9422(00)81759-8
  16. Rekka, E. and Kourounakis, P.N., Effect of hydroxyethyl rutenosides and related compounds on lipid peroxidation and free radical scavenging activity. Some structural aspects. J. Pharm. Pharmacol. 43, 486-491 (1991) https://doi.org/10.1111/j.2042-7158.1991.tb03519.x
  17. Shen, Y.C. and Chen, C.Y., Additional secoiridoid glucosides from Fraxinus uhdei. Planta Med 61, 281-283 (1995) https://doi.org/10.1055/s-2006-958076
  18. Stefanova, Z., Neychev, H., Ivanovska, N., and Kostova, I., Effect of a total extract from Fraxinus ornus stem bark and esculin on zymosan- and carrageenan-induced paw oedema in mice. J. Ethnopharmacol. 46, 101-106 (1995) https://doi.org/10.1016/0378-8741(95)01233-4
  19. Takenaka, Y., Tanahashi, T., Shintaku, M., Sakai, T., Nagakura, N., and Parida, N., Secoiridoid glucosides from Fraxinus americana. Phytochemistry 55, 275-284 (2000) https://doi.org/10.1016/S0031-9422(00)00319-8
  20. Tang, W. and Eisenbrand, G.., Chinese Drugs of Plant Origin, Springer-Verlag, Berlin, pp. 521-523 (1992)
  21. Tsukamoto, H., Hisada, S., and Nishibe, S., Lignans from bark of Fraxinus mandshurica var. japonica and F. japonica. Chem. Pharm. Bull. 32, 4482-4489 (1984) https://doi.org/10.1248/cpb.32.4482
  22. Tsukamoto, H., Hisada, S., and Nishibe, S., Coumarins from bark of Fraxinus japonica and F mandshurica var. japonica. Chem. Pharm. Bull. 33, 4069-4073 (1985) https://doi.org/10.1248/cpb.33.4069
  23. Yook, C.S., Kim, D.S., and Kim, S.M., Coumarin glycosides of Fraxinus japonica Blume forma intermedia Hara. Yakhak Hoeji 28, 283-286 (1984)
  24. Yook, C.S. and Moon, C.K., Coumarin glycosides from the root bark of Fraxinus sieboldiana Blume (II). Kor. J. Pharmacogn. 12, 143-145 (1981)