Antioxidant and anti-inflammatory activities of eugenol and its derivatives from clove (Eugenia caryophyllata Thunb.)

Journal of the Korean Society of Food Science and Nutrition

Volumn 40, Issue 10, 2011, Pages 1361-1370

  Leem, Hyun Hee ^a   Kim, Eun Ok ^a   Seo, Mi Jae ^b   Choi, Sang Won ^a  

^a Catholic University of Daegu   (South Korea)

^b Skylake Co   (South Korea)

Author keywords

Antioxidant and antiinflammatory activity; Clove (Eugenia caryophyllata Thunb.); Eugenol derivatives; Volatile components

Indexed keywords

EID: 84055213051     PISSN: 12263311     EISSN: None     Source Type: Journal    
DOI: 10.3746/jkfn.2011.40.10.1361     Document Type: Article

References (37)

1. Halliwell B, Gutteridge J. 1996. Free radicals, ageing, and disease. In Free Radicals in Biology and Medicine. Clarendon Press, London, UK. p 416-423.
2. Emerit J, Chaudiere J. 2008. Free radicals and lipid peroxidation in cell pathology. In Handbook of Free Radicals and Antioxidants in Biomedicine. Miquel J, Quintanilha A, Weber H, eds. CRC Press, Boca Raton, FL, USA. Vol, p 177-185.
3. Nakatani N. 1990. Recent advances in the study on natural antioxidants. Nippon Shokuhin Kogyo Gakkaishi 37: 569-576.
4. Giese J. 1996. Antioxidants: Tools for preventing lipid oxidation. Food Tech 11: 73-79.
5. Branen AL. 1975. Toxicology and biochemistry of butylated hydroxyanisole and butylated hydroxytoluene. J Am Oil Chem Soc 52: 59-64.
6. Ito N, Fukushima S, Fukushima H. 1985. Carcinogenicity and modification of the carcinogenicity response by BHA and BHT, and other antioxidants. CRC Crit Rev Food Technol 15: 109-111.
7. Liao JF, Chiou WF, Shen YC, Wang GJ, Chen CF. 2011. Anti-inflammatory and anti-infectious effects of Evodia rutaecarpa (Wuzhuyu) and its major bioactive components. Chinese Med 6: 1-8.
8. Hoshino T, Tabuchi K, Hara A. 2010. Effects of NSAIDs on the inner ear: possible involvement in cochlear protection. Pharmaceuticals 3: 1286-1295.
9. Rimon G, Sidhu R, Lauver D, Lee J, Sharma N, Yuan C, Frieler R, Trievel R, Lucchesi B, Smith W. 2010. Coxibs interfere with the action of aspirin by binding tightly to one monomer of cyclooxygenase-1. PNAS 107: 28-33.
10. Anderson GD, Keys KL, Ciechi PAD, Masferrer JL. 2009. Combination therapies that inhibit cyclooxygenase-2 and leukotriene synthesis prevent disease in murine collagen induced arthritis. Inflamm Res 58: 109-117.
11. Dogne JM, Hanson J, Supuran C, Pratico D. 2006. Coxibs and cardiovascular side-effects: from light to shadow. Curr Pharm Des 12: 917-975.
12. Makins R, Ballinger A. 2003. Gastrointestinal side effects of drugs. Expert Opin Drug Saf 2: 421-429.
13. Wuik, CS, Moon YH, Lee GJ. 1994. Hankookbonchohak. Hyungseoul Publishing Co., Seoul, Korea. p 304.
14. Dong S, Moon JS, Rhee SK, Son JY. 2004. Antioxidant activities of clove by extraction solvent. J Korean Soc Food Sci Nutr 33: 609-613.
15. Lee OH, Jung SH, Son JY. 2004. Antimicrobial activity of clove extract by extraction solvents. J Korean Soc Food Sci Nutr 33: 494-499.
16. Kang SY, Kim TG, Park MS, Han HM, Jung KK, Kang JH, Moon AR, Kim SH. 1999. Inhibitory effects of Eugenia caryophyllate, Ephedra sinica and Cinnamomum cassia on the replication of HBV in HepG2 cells. J Appl Pharmacol 7: 133-137.
17. Singh AK, Dhamanigi SS, Asad M. 2009. Anti-stress activity of hydroalcoholic extract of Eugenia caryophyllus buds (clove). Indian J Pharmacol 41: 28-31.
18. Ito M, Murakami K, Yoshino M. 2005. Antioxidant action of eugenol compounds: role of metal ion in the inhibition of lipid peroxidation. Food Chem Toxicol 43: 461-466.
19. Öztüurk A, Özbek H. 2005. The anti-inflammatory activity of eugenia caryophyllata essential oil: an animal model of anti-inflammatory activity. Eur J Gen Med 2: 159-163.
20. Kaur G, Athar M, Alam M. 2010. Eugenol precludes cutaneous chemical carcinogenesis in mouse by preventing oxidative stress and inflammation and by inducing apoptosis. Mol Carcinog 49: 290-301.
21. Wang C, Zhang J, Chen J, Fan Y, Shi Z. 2010. Antifungal activity of eugenol against Botrytis cinerea. Trop Plant Pathol 35: 137-143.
22. Kim SH, Shin TY, Kim HY, Lee YM, Lee EH, Shin BK, Kim YC, An NH, Kim HM. 1996. Inhibition of immediate allergic reaction by eugenol. Yakhak Hoeji 40: 679-683.
23. Schultz TH, Flath RA, Mon TR, Eggling SB, Teranishi R. 1977. Isolation of volatile components from a model system. J Agric Food Chem 25: 446-449.
24. Sehagen ES, Abbrahansom F, McLafferty W. 1974. The Wiley/NBS registry of mass spectral data. John Wiley and Sons, Ithaca, NY, USA. p 135
25. Tagashira M, Ohtake Y. 1988. A new antioxidative 1,3-benzo-dioxole from Melisa offocinalis. Planta Med 64: 555-558.
26. Lee KG, Takayuki S. 2001. Antioxidant property of aroma extract isolated from clove buds [Syzygium aomaticum (L.) Merr. et Perry]. Food Chem 74: 443-448.
27. Park MK, Park JH, Shin YG, Shin YK, Kim HH. 1997. Chemical constituents of Eugenia caryophyllata. Yakhak Hoeji 41: 149-152.
28. Brand-Williams W, Cuvelier ME, Berset C. 1995. Use of a radical method to evaluate antioxidant activity. Lebensm Wiss Technol 28: 25-30.
29. Masahiro O, Midori H, Shiro U, Toyoshige E. 2000. Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem Pharm Bull 48: 1467-1469.
30. Baskaran Y, Periyasamy V, Venkatraman AC. 2010. Investigation of antioxidant, anti-inflammatory and DNA-protective properties iof eugenol in thioacetamide-induced liver injury in rats. Toxicology 268: 204-212.
31. Fujisawa S, Atsumi T, Kadoma Y, Sakagami H. 2002. Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology 177: 39-54.
32. Park HJ. 2006. Toxicological studies on the essential oil of Eugenia caryophyllata Buds. Natural Product Sci 12: 94-100.
33. Murakami Y, Shoji M, Hanazawa S, Tanaka S, Fujisawa S. 2003. Preventive effect of bis-eugenol, a eugenol ortho dimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages. Biochem Pharmacol 66: 1061-1066.
34. Murakami Y, Shoji M, Hirata A, Tanaka S, Yokoe I, Fujisawa S. 2005. Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages. Arch Biochem Biophys 434: 326-332.
35. Magalhaes CB, Riva DR, Depaula LJ, Brando-Lima A, Koatz VLG, Leal-Cardoso JH, Zin WA, Faffe DS. 2010. In vivo anti-inflammatory action of eugenol on lipopolysaccharide-induced lung injury. J Appl Physiol 108: 845-851.
36. An SM, Lee SI, Choi SW, Moon SW, Boo YC. 2008. ρ-Coumaric acid, a constituent of Sasa quelpaertensis Nakai, inhibits cellular melanogenesis stimulated by α-melanocyte stimulating hormone. Brit J Dermatol 159: 292-299.
37. Dong S, Jung SH, Moon JS, Rhee SK, Son JY. 2004. Antioxidant activities of clove by extraction solvent. J Korean Soc Food Sci Nutr 33: 609-613.