Evaluation of chemical composition, anti-inflammatory and anti-nociceptive effects of Eugenia caryophyllata buds essential oil

Journal of Medicinal Herbs, "J. Med Herb" (Formerly known as Journal of Herbal Drugs or J. Herb Drug)

مقاله 3، دوره 5، شماره 2، مهر 2014، صفحه 68-78   

نوع مقاله: Original article

نویسندگان

Emad Khalilzadeh^* ؛ Reza Hazrati؛ Gholamreza Vafaei Saiah

Division of Physiology, Department of Basic Science, Faculty of Veterinary Medicine, University of Tabriz, Tabriz, Iran

چکیده

Background & Aim: Eugenia caryophyllata well known as Clove is a tree from Myrtaceae family that several parts of this plant traditionally used in dental care as an analgesic. This study aimed to assess the chemical composition, anti-inflammatory and anti-nociceptive activities of the essential oil extracted from Clove buds. Experimental: The essential oil of Clove buds (EOC) was extracted by Clevenger type apparatus and its chemical composition determined by gas chromatography-mass spectrometry (GC-MS). Analgesic activities of EOC were measured by formalin-induced orofacial pain and tail immersion test in rat. Also anti-inflammatory effect of the EOC was evaluated by using xylene induced ear edema test in mice. Results: EOC (100, 200 mg/kg, SC) and ketoprofen (80 and 160 mg/kg, IP) inhibit only the second phase of orofacial pain. Morphine (5 mg/kg) as a positive control significantly (p <0.05) reduced pain response in the both phases of pain. Pre-treatment of animals with naloxone did not prevent the EOC (200 mg/kg) analgesic activity. Co-administration of sub-analgesic doses of EOC (50 mg/kg) and ketoprofen (40 mg/kg) significantly (p <0.05) reduced nociceptive behavior in second phase. Also EOC (100 and 200 mg/kg) failed to increase nociceptive response latency in the tail immersion test. Meanwhile, EOC (100 and 200 mg/kg) and ketoprofen (80 mg/kg) significantly (p <0.001) attenuated xylene-induced ear edema in mice. Also according to GC-MS results the major components of the EOC were eugenol (54.86%), β-Caryophyllene (20.19%), α-Humulene (7.11%), eugenol acetat (4.85%) and Chavibetol (2.23%). Recommended applications/industries: These data showed that EOC possessed potent anti-inflammatory activity and produced non-opioid mediated analgesia in the second phase of orofacial pain without any effect on tail immersion response.

کلیدواژه‌ها

Clove essential oil؛ Ketoprofen؛ Morphine؛ Naloxone؛ Orofacial pain؛ Tail immersion

مراجع

Anand, P., Whiteside, G., Fowler, C.J., and Hohmann, A.G. 2009. Targeting CB2 receptors and the endocannabinoid system for the treatment of pain. Brain Res Rev, 60: 255-266.

Arung, E.T., Matsubara, E., Kusuma, I.W., Sukaton, E., Shimizu, K., and Kondo, R. 2011. Inhibitory components from the buds of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells. Fitoterapia, 82: 198-202.

Belmonte, C., Acosta, M.C., and Gallar, J. 2004. Neural basis of sensation in intact and injured corneas. Exp Eye Res, 78: 513-525.

Chaieb, K., Hajlaoui, H., Zmantar, T., Kahla-Nakbi, A.B., Mahmoud, R., Mahdouani, K., and Bakhrouf, A. 2007. The chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): a short review. Phytother Res, 21: 501-506.

Chen, Y.F., Tsai, H.Y., and Wu, T.S. 1995. Anti-inflammatory and analgesic activities from root of Angelica pubescens. Planta Med, 61: 2-8.

Cho, J.S., Kim, T.H., Lim, J.M., Song, J.H. 2008. Effects of eugenol on Na⁺ currents in rat dorsal root ganglion neurons. Brain Res, 1243: 53-62.

Daniel, A.N., Sartoretto, S.M., Schmidt, G., Caparroz-Assef, S.M., Bersani-Amado, C.A., and Cuman, R.K.N. 2009. Anti- inflammatory and antinociceptive activities A of eugenol essential oil in experimental animal models. Rev Bras Farmacogn, 19: 212-217.

Erfanparast, A., Tamaddonfard, E., Farshid, A.A., and Khalilzadeh, E. 2010. Effect of microinjection of histamine into the dorsal hippocampus on the orofacial formalin-induced pain in rats. Eur j Pharmacol, 627:119-123.

Gertsch, J., Leonti, M., Raduner, S., Racz, I., Chen, J.Z., Xie, X.Q., Altmann, K.H., Karsak, M., and Zimmer, A. 2008. Beta-caryophyllene is a dietary cannabinoid. Proc Natl Acad Sci USA, 26: 9099-9104.

Gülçin, I., Elmastas, M., and Aboul-Enein, H.Y. 2012. Antioxidant activity of clove oil – A powerful antioxidant source. Arabian J Chem, 5: 489-499.

Halder, S., Bharal, N., Mediratta, P.K., Kaur, I., and Sharma, K.K. 2009. Antiinflammatory, immunomodulatory and antinociceptive activity of Terminalia arjuna Roxb bark powder in mice and rats. Indian J Exp Biol, 47: 577-583.

Hashimoto, S., Uchiyama, K., Maeda, M., Ishitsuka, K., Furumoto, K., and Nakamura, Y. 1988. In vivo and in vitro effects of zinc oxide-eugenol (ZOE) on biosynthesis of cyclooxygenase products in rat dental pulp. J Dent Res, 67: 1092-1096.

Kildea, M.A., Allanb, G.L., and Kearney, R.E. 2004. Accumulation and clearance of the anaesthetics clove oil and AQUI-S from the edible tissue of silver perch (Bidyanus bidyanus). Aquaculture, 232: 265-277.

Kim, H.M., Lee, E.H., Hong, S.H., Song, H.J., Shin, M.K., Kim, S.H., and Shin, T.Y. 1998. Effect of Syzygium aromaticum extract on immediate hypersensitivity in rats. J Ethnopharmacol, 60: 125-131.

Kim, H.D., Cho, H.R., Moon, S.B., Shin, H.D., Yang, K.J., Park, B.R., Jang, H.J., Kim, L.S., Lee, H.S., and Ku, S.K. 2007. Effects of beta-glucan from Aureobasidium pullulans on acute inflammation in mice. Arch Pharmacal Res, 30: 323-328.

Kouidhi, B., Zmantar, T., and Bakhrouf, A. 2010. Anticariogenic and cytotoxic activity of clove essential oil (Eugenia caryophyllata) against a large number of oral pathogens. Ann Microbiol, 60: 599-604.

Kurian, R., Arulmozhi, D.K., Veeranjaneyulu, A., and Bodhankar, S.L. 2006. Effect of eugenol on animal models of nociception. Indian J Pharmacol, 38: 341-345.

Le Bars, D., Gozariu, M., and Cadden, S.W. 2001. Animal models of nociception. Pharmacol Rev, 53: 597-652.

Lee, M.H., Yeon, K.Y., Park, C.K., Li, H.Y., Fang, Z., Kim, M.S., Choi, S.Y., Lee, S.J., Lee, S., Park, K., Lee, J.H., Kim, J.S, and Oh, S.B. 2005. Eugenol inhibits calcium currents in dental afferent neurons. J Dent Res, 84: 848-51.

Lionnet, L., Beaudry, F., and Vachon, P. 2010. Intrathecal eugenol administration alleviates neuropathic pain in male Sprague-Dawley rats. Phytother Res, 24: 1645-1653.

Markowitz, K., Moynihan, M., Liu, M., and Kim, S. 1992. Biologic properties of eugenol and zinc oxide-eugenol. A clinically oriented review. Oral Surg Oral Med Oral Pathol, 73: 729-737.

Miranda, H.F., Sierralta, F., and Prieto, J.C. 2009. Synergism between NSAIDs in the orofacial formalin test in mice. Pharmacol Biochem Be, 92: 314–318.

Okhubo, T., Kitamura, K. 1997. Eugenol activates Ca2⁺-permeable currents in rat dorsal root ganglion cells. J Dent Res, 76: 1737-1744.

Okhubo, T., Shibata, M. 1997. The selective capsaicin antagonist capsazepine abolishes the antinociceptive action of eugenol and guaiacol. J Dent Res, 76: 848-851.

Park, C.K., Li, H.Y., Yeon, K.Y., Jung, S.J., Choi, S.Y., Lee, S.J., Lee, S., Park, K., Kim, J.S., and Oh, S.B. 2006. Eugenol inhibits sodium currents in dental afferent neurons. J Dent Res, 85: 900-904

Park, C.K., Kim, K., Jung, S.J., Kim, M.J., Ahn, D.K., Hong, S.D., Kim, J.S., and Oh, S.B. 2009. Molecular mechanism for local anesthetic action of eugenol in the rat trigeminal system. Pain, 144: 84-94.

Park, I.K., Lee, H.S., Lee, S.G., Park, J.D., and Ahn, Y.J. 2000. Insecticidal and fumigant activities of Cinnamomum cassia bark-derived material against Mechoris ursulus (Coleoptera Attelabidae). J Agric Food Chem, 48: 2528-2531.

Park, S.H., Sim, Y.B., Lee, J.K., Kim, S.M., Kang, Y.J., Jung, J.S., and Suh, H.W. 2011. The analgesic effects and mechanisms of orally administered eugenol. Arch Pharm Res, 34(3): 501-507.

Peana. A.T., Chessa, G., Carta, G., Delogu, G., and Fabbri, D. 2004. Eugenol, bis-eugenol and synthesized related-dimer compounds produce antinociception in the acetic acid-induced-writhing responses. Curr Top Phytochem, 6: 137-143.

Petrović, S., Dobrić, S., Mimica-Dukić, N., and Simin, N. 2008. The antiinflammatory, gastroprotective and antioxidant activities of Hieracium gymnocephalum extract. Phytother Res, 22: 1548–1551.

Pinto, E., Vale-Silva, L., Cavaleiro, C., and Salgueiro. L. 2009. Antifungal activity of the clove essential oil from Syzygium aromaticum on Candida, Aspergillus and dermatophyte species. J Med Microbiol, 58: 1454-1462.

Raboisson, P., Dallel, R. 2004. The orofacial formalin test. Neurosci Biobehav Rev, 28: 219-226.

Schiller, C., Schiller, D. 2008. The Aromatherapy Encyclopedia: A concise guide to 385 Essential Plant Oils. Basic Health Publications, Inc.

Sensch, O., Vierling, W., Brandt, W., and Reiter, W. 2000. Effects of inhibition of calcium and potassium currents in guinea-pig cardiac contraction: comparison of beta-caryophyllene oxide, eugenol, and nifedipine. Br J Pharmacol, 131: 1089-1096.

Shelef, L.A. 1983. Antimicrobial effects of spices. J Food Saf, 6: 29-44.

Soto, C.G., Burhanuddin, C.G. 1995. Clove oil as a fish anaesthetic for measuring length and weight of rabbit fish (Siganus lineatus). Aquaculture, 136: 149-152.

Zaninir, J.C., Medeiros, Y.S., Cruz, A.B., Yunes, R.R.A., and Calixto, J.B. 1992. Action of compounds from Mandevilla velutina on croton oil induced ear oedema in mice: a comparative study with steroidal and non-steroidal anti-inflammatory drugs. Phytother Res, 6: 1-5.

Zdunić, G., Godevac, D., Milenković, M., Vucićević, D., Savikin, K., Menković, N., and Petrović, S. 2009. Evaluation of Hypericum perforatum oil extracts for an antiinflammatory and gastroprotective activity in rats. Phytother Res, 23: 1554-1564.

Zhang, G.Q., Huang, X.D., Wang, H., Leung, A.K., Chan, C.L., Fong, D.W., and Yu. Z.L. 2008. Anti-inflammatory and analgesic effects of the ethanol extract of Rosa multiflora Thunb. hips. J Ethnopharmacol, 118:290-294.

Zimmermann, M. 1983. Ethical guidelines for investigations of experimental pain in conscious animals. Pain, 16: 109-110.