Anti-Oxidative and Nitric Oxide Production Inhibitory Activities of Phenolic Compounds from the Fruits of Actinidia arguta

  • Published : 2006.12.30

Abstract

Phytochemical examination of the fruits of Actinidia arguta has led to the isolation three organic acids, one coumarin, and three flavonoids. Structures of these compounds were elucidated as protocatechuic acid (1), caffeic acid (2), $caffeoyl-\beta-D-glucopyranoside$ (3), esculetin (4), quercetin (5), quercetin $3-O-\beta-D-galactopyranoside$ (6), and quercetin $3-O-\alpha-L-rhamnopyranosyl$ $(1\rightarrow6)-O-\beta-D-glucopyranoside$ (7) by comparisons with previously reported spectral data. To investigate the anti-inflammatory and anti-oxidative effects of these compounds, nitric oxide production inhibitory activity in LPS-stimulated RAW 264.7 cells and DPPH radical scavenging activities were examined. Nitric oxide productions were reduced significantly by the addition of compounds $[1(IC_{50}=59.27{\mu}g/ml),\;2(IC_{50}=27.95{\mu}g/ml),\;3(IC_{50}=73.09{\mu}g/ml),\;4(IC_{50}=67.44{\mu}g/ml),\;5(IC_{50}=17.40{\mu}g/ml),\;6(IC_{50}=41.99{\mu}g/ml),\;7(IC_{50}=54.46{\mu}g/ml)]$, and extracts $(IC_{50}=56.21{\mu}g/ml)$ compared with positive control, L-NMMA $(IC_{50}=14.48{\mu}g/ml)$. The phenolic compounds also showed anti-oxidative activities. Especially, Compounds $1(IC_{50}=8.87{\mu}g/ml),\;4(IC_{50}=3.41{\mu}g/ml),\;and\;5(IC_{50}=6.06{\mu}g/ml),\;$, showed potent anti-oxidative activities similar to L-ascorbic acid $(IC_{50}=5.89{\mu}g/ml)$.

Keywords

References

  1. Agrawal, P.K., Carbon-13 NMR of flavonoids, Elsevier, 94-364 (1989)
  2. Berregi, I., Santos, J., Campo, G., Miranda, J., and Aizpurua, J., Quantitation determination of chlorogenic acid in cider apple juices by $^{1}H$-NMR spectrometry. Anal. Chim. Acta, 486, 269-274 (2003) https://doi.org/10.1016/S0003-2670(03)00496-3
  3. Epe, B., Ballmaier, D., Roussyn, I., Brivida, K., and Sied, H., DNA damage by peroxynitrite characterized with DNA repair enzyme. Nucleic Acids Res., 24, 4105-10 (1996) https://doi.org/10.1093/nar/24.21.4105
  4. Feelisch, M. and Stamler, J., Methods in nitric oxide reserch. John Wiley & Sons, 492-497 (1996)
  5. Fumihide, T., Tomoaki, T., Jiro, A., Nobuo, Y., and Shinji, F., Protective eflect of (+)-catechin against 5-fluorouracil-induced myelosupperession in mice. Toxicology., 201, 133-142 (2004) https://doi.org/10.1016/j.tox.2004.04.009
  6. Ganster, R.W., Taylor, B.S., Shao, L., and Geller, D.A., Complex regulation of human inducible nitric oxide synthase gene transcription by Stat 1 and NF-kappaB. Proc. Natl. Acad. Sci. USA, 98, 8638-8643 (1980)
  7. Harborne, J.B. and Mabry, T.J., The Flavonoids. Chapman and Hall, 285-289 (1982)
  8. Hatano, T., Edamatsu, R., Hiramatsu, M., Mori, A., Fujita, Y., Yasuhara, T., Yoshida, T. and Okuda, T., Effects of the interaction of tannins with co-existing substances. Effects of tannins and ralated polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull., 37, 2016 (1989) https://doi.org/10.1248/cpb.37.2016
  9. Hobbs, A., Higgs, A., and Moncada, S., Inhibition of nitric oxide synthase as a potential therapeutic target. Annu. Rev. Pharmacol. Toxicol., 39, 191-220 (1999) https://doi.org/10.1146/annurev.pharmtox.39.1.191
  10. Hou, F., Chen, F., Lu, Y., and sun, J., Anti-infective and anti-tumor effects of Actinidia arguta stem polysaccharide. Baiqiuen Yike Daxue Xuebao., 21, 472-475 (1995)
  11. Hou, L.F., Zhou, B., Yang, L., and Liu, Z.L., Inhibition of human low density lipoprotein oxidation by flavonols and their glycosides. Chem. Phys. Lipids, 129, 209-219 (2004) https://doi.org/10.1016/j.chemphyslip.2004.02.001
  12. Jacob, R.A., Nutrition, health and antioxidants. Inform., 5, 1271-1275 (1994)
  13. Kehrer, J.P., Free radical as mediators injury and disease. Crit. Rev. Toxicol., 23, 21-48 (1993) https://doi.org/10.3109/10408449309104073
  14. Kharitonov, S., Yates, D., Robbins, R.A., Logan-Sinclair, R., Shinebourne, E.A., and Barnes, P.J., Increased nitric oxide in exgaled air of asthmatic patients. Lancet, 343, 133-5 (1994) https://doi.org/10.1016/S0140-6736(94)90931-8
  15. Kim, H.J., Yeom, S.H., Kim, M.G., Shim, J.G., Lim, H.W., and Lee, M.W., Nitric oxide and prostaglandin $E_{2}$ synthesis inhibitory activities of flavonoids from the barks of Ulmus macroearpa. Nat. Prod. Sci., 10, 344-346 (2004)
  16. Kim, H.J., Yeom, S.H., Kim, M.G., Shim, J.G., Baek, I.N., and Lee, M.W., Nitric oxide and prostaglandin $E_{2}$ synthesis inhibitory activities of diarylheptanoids from the barks of Alnus japonica Steudel. Arch. Pharm. Res., 28, 177-179 (2005) https://doi.org/10.1007/BF02977711
  17. Kim, J.-G. and Xiao, P.-G., Traditional Drugs of The East Color Edition, Young-Rim Publishing Co., 207 (1995)
  18. Kim, M.Y., Iwai, K., and Matsue, H., Phenolic compositions of Viburnum dilatatum Thunb. fruits and their antiradocal properties. J. Food Compost. Anal., 18, 789-802 (2005) https://doi.org/10.1016/j.jfca.2004.09.009
  19. Lee, J.H., Ku, C.H., Baek, N.I., Kim, S.H., Park, H.W., and Kim, D.K., Phytochemical constituents from Diodia teres. Arch. Pharm. Res., 27, 40-43 (2004) https://doi.org/10.1007/BF02980043
  20. Lim, H.W., Shim, J.G., Choi, H.K., and Lee, M.W., Phenolic compounds from barks of Actinidia arguta Planchon growing in Korea and its anti-oxidative and nitric oxide production inhibitory activities. Kor. J. Pharmacogn., 36, 245-251 (2005)
  21. Lin, M.Y. and Yen, C.L., Antioxidative ability of lactic acid bacteria. J. Agric. Food Chem., 47, 1460-1466 (1999) https://doi.org/10.1021/jf981149l
  22. Liu, R., Sun, Q., Sun, A., and Cui, J., Isolation and purification of coumarin compounds from Cortex fraxinus by high-speed counter-current chromatography. J. Chromatogr. A, 1072, 195-199 (2005) https://doi.org/10.1016/j.chroma.2005.03.023
  23. Mosmann, T., Rapid colorimetric assay for the cellular growth and survival. J. Immun. Methods, 65, 55 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  24. Park, E., Kim, B., Jong, H., Son, M., Kim, S., and Jin, M.J., Control of IgE and allergy-related Th1 and Th2 cytokines by PG102, a watersoluble extract from Actinidia species. J. Allergy Clin. Immunol., 113, S323 (2004)
  25. Park, S.Y., Hong, S.S., Han, X.H., Ro, J.S. and Hwang, B.Y., Inhibitory constituents of LPS-induced nitric oxide production from Arctium lappa. Nat. Prod. Sci., 11, 85-88 (2005)
  26. Sautebin, L., Prostaglandins and nitric oxide as molecular targets tor anti-inflammatory therapy. Fitoterapia, 71, S48-57 (2000) https://doi.org/10.1016/S0367-326X(00)00181-7
  27. Sroka, Z. and Cisowski, W., Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food Chem. Toxicol., 41, 753-758 (2003) https://doi.org/10.1016/S0278-6915(02)00329-0
  28. Webby, R.F., A flavonol triglycoside from Actinidia arguta var. giraldii. Phytochemistry, 30, 2443-2444 (1991) https://doi.org/10.1016/0031-9422(91)83680-J
  29. Webby, R.F. and Markham, K.R., Flavonol-3-O-triglycosides from Actinidia species. Phytochemistry, 29, 289-292 (1990) https://doi.org/10.1016/0031-9422(90)89052-B