Toxicological Studies on the Essential Oil of Eugenia caryophyllata Buds

  • 발행 : 2006.06.01

초록

The essential oil (EC-oil) obtained from the buds of Eugenia caryophyllata (Myrtaceae) was examined for its free radical-scavenging activity, cytotoxicity, and in vivo toxicity. To find the xenobiotic properties of EC-oil, serum thiobarbituric acid reactive substances (TBARS) level and hepatic drug-metabolizing enzyme activities were measured. It was found that EC-oil displayed xenobiotic properties like bromobenzene. The cytotoxicities of eugenol and of the EC-oil were greatly attenuated by the sulfhydryl-containing N-acetyl-L-cysteine (NAC), suggesting that eugenol was susceptible to nucleophilic sulfhydryl. In addition, eugenol also showed potent free radical-scavenging activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Moreover, methyleugenol considerably exhibited less cytotoxicity and less potent free radical-scavenging activity than eugenol, and the cell viability of the methyleugenol was more increased with NAC treatment than the eugenol. These results indicate that the phenolic OH in eugenol may play a crucial role in both cytotoxicity and free radical-scavenging activity. The fashion on oxidative stress and hepatic drug-metabolizing enzyme activities of eugenol resembled those of bromobenznene.

키워드

참고문헌

  1. Asha, M.K., Prashanth, D., Murali, B., Padmaja, R. and Amit, A., Anthelmintic activity of essential oil of Ocimum sanctum and eugenol. Fitoterapia, 669-670 (2001)
  2. Atsumi, T., Iwakura, I., Fujisawa, S., and Ueha, T., Reactive oxygen species generation and photo-cytotoxicity of eugenol in solutions of various pH. Biomaterials, 22, 1459-1466 (2001) https://doi.org/10.1016/S0142-9612(00)00267-2
  3. Bidlack, W.R. and Lowry, G.L.Multiple drug metabolism: P-nitroanisole reversal of acetone enhanced aniline hydroxylation. Biochem. Pharmacol., 31, 311-317 (1982) https://doi.org/10.1016/0006-2952(82)90176-9
  4. Chogo, J.B. and Crank, G, Chemical composition and biological activity of the Tanzanian Plant Ocimum suave. J. Nat. Prod, 42, 308-311 (1981)
  5. Choi, J, Lee, K.T., Ka, H., lung, H.J., and Park, H.J., Constituents of the essential oil of the Cinnamomum cassia stem bark and the biological properties. Arch. Pharm. Res., 25, 418-423 (2001)
  6. Choi, J., Lee, K.T., lung, W,T., lung, H.J., Lee, S.H., and Park, H.J., Inhibitory effect of the essential oils on acetaminophen-induced lipid peroxidation in the rat. Nat. Prod Sci., 8, 18-22 (2002)
  7. Deneke, S.M. and Fanburg, B.L., Normobaric oxygen toxicity of the lung. New Engl. J. Med, 303, 76-86 (1980) https://doi.org/10.1056/NEJM198007103030204
  8. Denizot, F. and Lang, R.J., Rapid colorimetric assay for cell growth and survival: modification to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 89, 271-277 (1996) https://doi.org/10.1016/0022-1759(86)90368-6
  9. Habig, W.H., Pabist, M.J., and Jakoby, W.B., The first enzymatic step in mercapturic acid formation. J. Biol. Chem., 249, 7130-7139 (1974)
  10. Halliwell, B., Biochemeical mechanism accounting for the toxic action of oxygen on living organism. Cell. Biol. Int. Rep., 2, 112-128 (1978)
  11. Han, D.S., 'Saengyakhak', Dongmyung-Sa, Seoul, 2001, pp. 265-267
  12. Harborne, J.B. and Baxter, H., 'Phytochemical Dictionary', Taylor and Francis, Washington DC, 1993, pp. 1765
  13. Kwon, H.C. and Lee, K.R., Phytochemical constituents of Artemisia japonica ssp.littoricola. Arch. Pharm. Res., 24, 194-197 (2001) https://doi.org/10.1007/BF02978255
  14. Lee, K.T., Park, H.J., Jung, H.J., and Choi, J., In vivo and in vitro antioxidant peroxidative effect of the extract complex of Koran antithirst drugs. Yakhak Hoeji, 46, 358-363 (2002)
  15. Mihara, S. and Shibamoto, T., Photochemical reactions of eugenol and related compounds: Synthesis of new flavor chemicals, J. Agric. Food Chern., 30, 1215-1218 (1982) https://doi.org/10.1021/jf00114a053
  16. Miyazawa, M. and Hisama, M., Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in Salmonella typhymurium TA1535/pSK1002 umu test. J. Agric. Food Chem., 49, 4019-4025 (2001) https://doi.org/10.1021/jf0103469
  17. Nash, T., The colorimetric estimation of formaldehyde by means of the hantzsch reaction. J. Biol. Chem., 55, 416-422 (1953)
  18. Ogata, M., Hoshi, M., Urano, S., and Endo, T., Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem. Pharm. Bull., 48, 1467-1469 (2000) https://doi.org/10.1248/cpb.48.1467
  19. Ohkawa, H., Ohishi, N., and Yagi, K., Assay for lipid peroxides in animal tissue by thiobarbituric acid reaction. Anal. Biochem., 95, 351-358 (1979) https://doi.org/10.1016/0003-2697(79)90738-3
  20. Omura, T. and Sato, R., The carbon monoxide binding pigments of liver microsomes In: Evidence for its hemoprotein nature. J. Biol. Chem., 239, 2370-2385 (1964)
  21. Park, I.K., Lee, H.S., Lee, S.G, and Park, J.D., Ahn Y.J., Insecticidal and fumigant activities of Cinnamomum cassia bark-derived materials against Mechoris ursulus (Coleoptera: Attelabidae). J. Agric. Food Chem., 48, 2528-2531 (2000) https://doi.org/10.1021/jf9904160
  22. Rajagopalan, K.V., Fridovich, I., Handler, P., Palmer, G, and Beinert, H., Studies of aldehyde oxidase by electron paramagnetic resonance spectroscopy. J. Biol. Chem., 243, 3783-3796 (1968)
  23. Schaffuer, F., Vet. Pathol., Hepatic drug metabolism and adverse hepatic drug reactions. 12, 145-156 (1975) https://doi.org/10.1177/030098587501200206
  24. Singh, A. and Rae, A.R, Effects of arecoline on phase I and phase II drug metabolizing system enzymes, sylfhydryl content and lipid peroxidation in mouse liver. Biochem Mol. Biol. Int., 30, 763-772 (1993)
  25. Stripe, F., and Della, C.E., The regulation of rat liver xanthine oxidase: Conversion in vitro of the enzyme activity from dehydrogenase (Type D) to oxidase (Type O). J. Biol. Chem., 244, 3855-3863 (1969)
  26. Xiong, Q., Kadota, S., Tani, T., and Namba, T., Antioxidative effects of phenylethanoids from Cistanche deserticola. Biol. Pharm. Bull., 19, 1580-1585 (1996) https://doi.org/10.1248/bpb.19.1580
  27. Zheng, G.-Q., Kenney, P.M., and Lam, L.K.T., Sesquiterpenes from clove (Eugenia caryophyllata). J. Nat. Prod. 55, 999-1003 (1992) https://doi.org/10.1021/np50085a029