Anti-inflammatory Activities of Chopi (Zanthoxylum piperitum A.P. DC) Essential Oil: Suppression of the Inducible Nitric Oxide Synthase and Cellular Adhesion

  • Lee, Je-Hyuk (Plant Resource Research Institute, Duksung Women's University) ;
  • Chang, Kyung-Mi (Plant Resource Research Institute, Duksung Women's University) ;
  • Kim, Gun-Hee (Plant Resource Research Institute, Duksung Women's University)
  • Published : 2009.12.31

Abstract

The aim of this study is to elucidate the anti-inflammatory activities of chopi (Zanthoxylum piperitum A.P. DC.) essential oil. Essential oil (EO) of chopi was extracted by steam distillation method, and its major constituents were limonene and geranyl acetate. Chopi-EO decreased approximately 38% of nitrite production, as compared to the lipopolysaccharde (LPS)-induced nitrite production. However, chopi-EO and its components did not quench nitric oxide (NO) chemically in cellfree system, and markedly inhibited approximately 40.4% of inducible nitric oxide synthase (iNOS) mRNA transcription. In addition, the inhibition of E-selectin gene transcription by chopi-EO caused the suppression of cellular adhesion. These results suggest that chopi-EO may exert potential anti-immunological inflammatory activity.

References

  1. Marletta MA. Nitric oxide synthase structure and mechanism. J. Biol. Chem. 268: 12231-12234 (1993)
  2. Palmer RM, Ashton DS, Moncada S. Vascular endothelial cells synthesize nitric oxide from L-arginine. Nature 333: 664-666 (1988) https://doi.org/10.1038/333664a0
  3. Xie Q-W, Cho HJ, Calaycay J, Mumford RA, Swiderek KM, Lee TD, Ding A, Troso T, Nathan CF. Cloning and characterization of inducible nitric oxide synthase from mouse macrophages. Science 256: 225-228 (1992) https://doi.org/10.1126/science.1373522
  4. Hibbs JB, Taintor RR, Vavrin Z. Macrophage cytotoxicity: Role for L-arginine deiminase and imino nitrogen oxidation in nitrite. Science 235: 473-476 (1987) https://doi.org/10.1126/science.2432665
  5. Chung MS. Volatile compounds of Zanthoxylum piperitum A.P. DC. Food Sci. Biotechnol. 14: 529-532 (2005)
  6. Caldefie-Chezet F, Guerry M, Chalchat JC, Fusillier C, Vasson MP, Guillot J. Anti-inflammatory effects of Melaleuca alternifolia essential oil on human polymorphonuclear neutrophils and monocytes. Free Radical Res. 38: 805-811 (2004) https://doi.org/10.1080/1071576042000220247
  7. Hart PH, Brand C, Carson CF, Riley TV, Prager RH, Finlay-Jones JJ. Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses inflammatory mediator production by activated human monocytes. Inflamm. Res. 49: 619-626 (2000) https://doi.org/10.1007/s000110050639
  8. Fiebich BL, Mueksch B, Boehringer M, Hull M. Interleukin-1$\beta$ induces cyclooxygenase-2 and prostaglandin E2 synthesis in human neuroblastoma cells: Involvement of p38 mitogen-activated protein kinase and nuclear factor-$\kappa$B. J. Neurochem. 75: 2020-2028 (2000) https://doi.org/10.1046/j.1471-4159.2000.0752020.x
  9. Silverman MD, Zamora DO, Pan Y, Texeira PV, Planck SR, Rosenbaum JT. Cell adhesion molecule expression in cultured human iris endothelial cells. Invest. Ophth. Vis. Sci. 42: 2861-2866 (2001)
  10. Gomez NE, Witte L. A simple method to extract essential oils from tissue samples by using microwave radiation. J. Chem. Ecol. 27: 2351-2359 (2001) https://doi.org/10.1023/A:1012295307740
  11. Van den Dool H, Kratz PD. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatogram. J. Chromatogr. 11: 463-471 (1963) https://doi.org/10.1016/S0021-9673(01)80947-X
  12. Kondjoyan N, Berdague JL. A Compilation of Relative Retention for the Analysis of Aromatic Compounds. Laboratorie flaveur, de Recherches sur la Viande. Clemont-Ferrand, France. pp. 15-138 (1996)
  13. Chattopadhyay S, Bhaumik S, Purkayastha M, Basu S, Chaudhuri AN, Gupta SD. Apoptosis and necrosis in developing brain cells due to arsenic toxicity and protection with antioxidants. Toxicol. Lett. 136: 65-76 (2002) https://doi.org/10.1016/S0378-4274(02)00282-5
  14. Babu BH, Shylesh BS, Padikkala J. Antioxidant and hepatoprotective effect of Acanthus ilicifolius. Fitoterapia 72: 272-277 (2001) https://doi.org/10.1016/S0367-326X(00)00300-2
  15. Wei T, Chen C, Hau J, Zhao B, Xin W, Mori A. The antioxidant EPC-K1 attenuates NO-induced mitochondrial dysfunction, lipid peroxidation, and apoptosis in cerebellar granuele cells. Toxicology 134: 117-126 (1999) https://doi.org/10.1016/S0300-483X(99)00030-X
  16. Lee JH, Choi SI, Lee YS, Kim GH. Antioxidant and antiinflammatory activities of Allium victorialis subsp. platyphyllum extracts. Food Sci. Biotechnol. 16: 796-801 (2007)
  17. Ahn KS, Noh EJ, Zhao HL, Jung SH, Kang SS, Kim YS. Inhibition of inducible nitric oxide synthase and cylooxygenase II by Platycodon grandiflorum saponins via suppression of nuclear factor-$\kappa$B activation in RAW 264.7 cells. Life Sci. 76: 231-2328 (2005)
  18. Sasaki M, Ohara-Nemoto Y, Tajika S, Kobayashi M, Yamaura C, Kimura S. Antigenic characterization of a novel Streptococcus anginosus antigen that induces nitric oxide synthesis by murine peritoneal exudates cells. J. Med. Microbiol. 50: 952-958 (2001)
  19. Choi JS, Choi YJ, Park SH, Kang JS, Kang YH. Flavones migrate tumor necrosis factor-$\alpha$-induced adhesion molecule upregulation in cultured human endothelial cells: Role of nuclear factor-$\kappa$B. J. Nutr. 134: 1013-1019 (2004)
  20. Rasmussen LM, Hansen PT, Nabipour MT, Olesen P, Kristiansen MT, Ledet T. Diverse effects of inhibition of 3-hydroxy-3-methylglutaryl-CoA reductase on the expression of VCAM-1 and E-selectin in endothelial cells. Biochem. J. 360: 363-370 (2001) https://doi.org/10.1042/0264-6021:3600363
  21. Kim JH, Lee KS, Oh WT, Kim KR. Flavor components of the fruit peel and leaf oil from Zanthoxylum piperitum DC. Korean J. Food Sci. Technol. 21: 562-568 (1989)
  22. Chung MS. Compositional changes in essential oil of Zanthoxylum piperitum A.P. DC during storage. Korean J. Food Culture 21: 433-438 (2006)
  23. Babior BM. The respiratory burst oxidase. Adv. Enzymol. RAMB 65: 49-95 (1992)
  24. Lu XG, Feng BA, Zhan LB, Yu ZH. D-Limonene induces apoptosis of gastric cancer cells. Zhongguo Shi Yan Xue Ye Xue Za Zhi 25: 325-327 (2003)
  25. Whysner J, Williams GM. D-Limonene mechanistic data and risk assessment: Absolute species-specific cytotoxicity, enhanced cell proliferation, and tumor promotion. Pharmacol. Therapeut. 71: 127-136 (1996) https://doi.org/10.1016/0163-7258(96)00065-4
  26. Belmont HM, Levartovsky D, Goel A, Amin A, Giorno R, Rediske J, Skovron ML, Abramson SB. Increased nitric oxide production accompanied by the up-regulation of inducible nitric oxide synthase in vascular endothelium from patients with systemic lupus erythematosus. Arthritis Rheum. 40: 1810-1816 (1997)
  27. Amin AR, Attur M, Abramson SB. Nitric oxide synthase and cyclooxygenases: Distribution, regulation, and intervention in arthritis. Curr. Opin. Rheumatol. 11: 202-209 (1999) https://doi.org/10.1097/00002281-199905000-00009
  28. Leikert JF, Rathel TR, Wohlfart P, Cheynier V, Vollmar AM, Dirsch VM. Red wine polyphenols enhance endothelial nitric oxide synthase expression and subsequent nitric oxide release from endothelial cells. Circulation 106: 1614-1617 (2002) https://doi.org/10.1161/01.CIR.0000034445.31543.43
  29. Cauin-Glaser T, Garcia-Cardena G, Sarrel P, Sessa WC, Bender JR. 17$\beta$-Estradiol regulation of human endothelial cell basal nitric oxide release, independent of cytosolic $Ca^{2+}$ mobilization. Circ. Res. 81: 885-892 (1997) https://doi.org/10.1161/01.RES.81.5.885
  30. Mordan LJ, Burnett TS, Zhang LX. Inhibitors of endogenous nitric oxide formation block the promotion of neoplastic transformation in C3H10T1/2 fibroblasts. Carcinogenesis 14: 1555-1559 (1993)
  31. Chan MM, Huang HI, Fenton MR, Fong D. In vivo inhibition of nitric oxide synthase gene expression by curcumin, a cancer preventive natural product with anti-inflammatory properties. Biochem. Pharmacol. 55: 1955-1962 (1998) https://doi.org/10.1016/S0006-2952(98)00114-2
  32. Lee CW, Lin WN, Lin CC, Luo SF, Wang JS, Pouyssegur J, Yang CM. Transcriptional regulation of VCAM-1 expression by tumor necrosis factor-α in human tracheal smooth muscle cells: Involvement of MAPKs, NF-κB, p300, and histone acetylation. J. Cell. Physiol. 207: 174-186 (2006) https://doi.org/10.1002/jcp.20549