Antiproliferative and molecular mechanism of eugenol-induced apoptosis in cancer cells

Molecules

Volumn 17, Issue 6, 2012, Pages 6290-6304

  Jaganathan, Saravana Kumar ^a   Supriyanto, Eko ^b  

^a PSNA COLLEGE OF ENGINEERING AND TECHNOLOGY   (India)

^b UNIVERSITI TEKNOLOGI MALAYSIA   (Malaysia)

Author keywords

Antiproliferative; Cancer; Chemoprevention; Eugenol

Indexed keywords

ANTINEOPLASTIC AGENT; EUGENOL;

ANIMAL; APOPTOSIS; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECT; HUMAN; METABOLISM; NEOPLASM; REVIEW;

ANIMALS; ANTICARCINOGENIC AGENTS; APOPTOSIS; CELL PROLIFERATION; EUGENOL; HUMANS; NEOPLASMS;

EID: 84863009824     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17066305     Document Type: Review

References (40)

1. Sporn, M. B.; Newton, D. L. Chemoprevention of cancer with retinoids. Fed. Proc. 1979, 38, 2528-2534. (Pubitemid 10249287)
2. Kelloff, G. J. Perspectives on cancer chemoprevention research and drug development. Adv. Cancer Res. 1999, 78, 320-334.
3. Kelloff, G. J.; Boone, C. W. Cancer chemopreventive agents: Drug development status and future prospects. J. Cell. Biochem. 1994, 20, 1-303.
4. Kelloff, G. J.; Hawk E. T.; Sigman, C. C. Cancer Chemoprevention: Promising Cancer Chemopreventive Agents; Humana Press: Totowa, NJ, USA, 2004.
5. Ferguson, L. R. Antimutagens as cancer chemopreventive agents in the diet. Mutat. Res. 1994, 307, 395-410. (Pubitemid 24155070)
6. Ferguson, L. R.; Philpott, M.; Karunasinghe, N. Dietary cancer and prevention using antimutagens. Toxicology 2004, 198, 147-159. (Pubitemid 38609024)
7. Surh, Y. J. Cancer chemoprevention with dietary phytochemicals. Nat. Rev. Cancer 2003, 3, 768-780.
8. Pisano, M.; Pagnan, G.; Loi, M.; Mura, M. E.; Tilocca, M. G.; Palmieri, G.; Fabbri, D.; Dettori, M. A.; Delogu, G.; Ponzoni, M.; et al. Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells. Mol. Cancer 2007, 6, 8-20.
9. Ogata, M.; Hoshi, M.; Urano, S.; Endo, T. Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem. Pharm. Bull. 2000, 48, 1467-1469.
10. Benencia, F.; Courreges, M. C. In vitro and in vivo activity of eugenol on human herpesvirus. Phytother. Res. 2000, 14, 495-500.
11. Chogo, J. B.; Crank, G. Chemical composition and biological activity of the tanzanian plant Ocimum suave. J. Nat. Prod. 1981, 42, 308-311. (Pubitemid 11063240)
12. Asha, M. K.; Prashanth, D.; Murali, B.; Padmaja, R.; Amit, A. Anthelmintic activity of essential oil of Ocimum sanctum and eugenol. Fitoterapia 2001, 72, 669-670. (Pubitemid 32799269)
13. Miyazawa, M.; Hisama, M. Suppression of chemical mutagen-induced SOS response by alkylphenols from clove (Syzygium aromaticum) in the Salmonella typhimurium TA1535/pSK1002. J. Agric. Food Chem. 2001, 49, 4019-4025. (Pubitemid 32822731)
14. Han, E. H.; Hwang, Y. P.; Jeong, T. C.; Lee, S. S.; Shin, J. G.; Jeong, H. G. Eugenol inhibit 7, 12-dimethylbenz[a]anthracene-induced genotoxicity in MCF-7 cells: Bifunctional effects on CYP1 and NAD (P) H: quinone oxidoreductase. FEBS Lett. 2007, 581, 749-756. (Pubitemid 46223567)
15. Abraham, S. K. Anti-genotoxicity of trans-anethole and eugenol in mice. Food Chem. Toxicol. 2001, 39, 493-498. (Pubitemid 32323983)
16. World Health Organization (WHO). Evaluation of Certain Food Additives and Contaminants; Twenty-sixth report of the Joint FAO/WHO Expert Committee on Food Additives, WHO Technical Report Series, No. 683; Geneva, Switzerland, 1982.
17. Lee, K. G.; Shibamoto, T. Antioxidant property of aroma extract isolated from clove buds Syzygium aromaticum (L.) Merr. et Perry. Food Chem. 2001, 74, 443-448. (Pubitemid 32761781)
18. Usta, J.; Copti, R. Effect of cinnamon, clove and some of their constituents on the Na+-K+-ATPase activity and alanine absorption in the rat jejunum. Food Chem. Toxicol. 2000, 38, 755-762. (Pubitemid 30628870)
19. Gursale, A. A.; Sane, R. T.; Menon, S.; Patel, P. H. Quantitative determination of eugenol from Cinnamomum tamala nees and eberm. Leaf powder and polyherbal formulation using reverse phase liquid chromatography. Chromatographia 2005, 61, 443-446. (Pubitemid 40767844)
20. Stamford, I. F.; Tavares, I. A.; Jacobs, S.; Capasso, F.; Mascolo, N.; Autore, G.; Romano, V. The biological activity of eugenol, a major constituent of nutmeg (Myristica fragrans): Studies on prostaglandins, the intestine and other tissues. Phytother. Res. 1988, 2, 124-130. (Pubitemid 19039457)
21. Kim, G. C.; Choi, D. S.; Lim, J. S.; Jeong, H. C.; Kim, I. R.; Lee, M. H.; Park, B. S. Caspases-dependent apoptosis in human melanoma cell by eugenol. Korean J. Anat. 2006, 39, 245-253.
22. Ghosh, R.; Nadiminty, N.; Fitzpatrick, J. E.; Alworth, W. L.; Slaga, T. J.; Kumar, A. P. Eugenol causes melanoma growth suppression through inhibition of E2F1 transcriptional activity. J. Biol. Chem. 2005, 280, 5812-5819. (Pubitemid 40280062)
23. Pal, D.; Banerjee, S.; Mukherjee, S.; Roy, A.; Panda, C. K.; Das, S. Eugenol restricts DMBA croton oil induced skin carcinogenesis in mice: Downregulation of c-Myc and H-ras, and activation of p53 dependent apoptotic pathway. J. Dermatol. Sci. 2010, 59, 31-39.
24. Kaur, G.; Athar, M.; Alam, M. S. Eugenol precludes cutaneous chemical carcinogenesis in mouse by preventing oxidative stress and inflammation and by inducing apoptosis. Mol. Carcinog. 2010, 49, 290-301.
25. Shin, S. H.; Park, J. H.; Kim, G. C. The mechanism of apoptosis induced by eugenol in human osteosarcoma cells. J. Korean Oral Maxillofac. Surg. 2007, 33, 20-27.
26. Yoo, C. B.; Han, K. T.; Cho, K. S.; Ha, J.; Park, H. J.; Nam, J. H.; Kil, U. H.; Lee, K. T. Eugenol isolated from the essential oil of Eugenia caryophyllata induces a reactive oxygen species-mediated apoptosis in HL-60 human promyelocytic leukemia cells. Cancer Lett. 2005, 225, 41-52. (Pubitemid 40732767)
27. Okada, N.; Hirata, A.; Murakami, Y.; Shoji, M.; Sakagami, H.; Fujisawa, S. Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression by eugenol-related compounds. Anticancer Res. 2005, 25, 3263-3269. (Pubitemid 41105199)
28. Manikandan, P.; Vinothini, G.; Priyadarsini, R. V.; Prathiba, D.; Nagini, S. Eugenol inhibits cell proliferation via NF-. B suppression in a rat model of gastric carcinogenesis induced by MNNG. Invest. New Drugs 2011, 29, 110-117.
29. Manikandan, P.; Murugan, R. S.; Priyadarsini, R. V.; Vinothini, G.; Nagini, S. Eugenol induces apoptosis and inhibits invasion and angiogenesis in a rat model of gastric carcinogenesis induced by MNNG. Life Sci. 2010, 86, 936-941.
30. Park, B. S.; Song, Y. S.; Yee, S. B.; Lee, B. G.; Seo, S. Y.; Park, Y. C.; Kim, J. M.; Kim, H. M.; Yoo, Y. H. Phospho-ser 15-p53 translocates into mitochondria and interacts with Bcl-2 and Bcl-xL in eugenol-induced apoptosis. Apoptosis 2005, 10, 193-200. (Pubitemid 40558127)
31. Rothschild, A. M. Mechanisms of histamine release by compound 48/80. Br. J. Pharmacol. 1970, 38, 253-262.
32. Ghosh, R.; Ganapathy, M.; Alworth, W. L.; Chan, D. C.; Kumar, A. P. Combination of 2-methoxyestradiol (2-ME2) and eugenol for apoptosis induction synergistically in androgen independent prostate cancer cells. J. Steroid Biochem. Mol. Biol. 2009, 113, 25-35.
33. Atsumi, T.; Fujisawa, S.; Satoh, K.; Sakagami, H.; Iwakura, I.; Ueha, T.; Sugita, Y.; Yokoe, I. Cytotoxicity and radical intensity of eugenol, isoeugenol or related dimers. Anticancer Res. 2000, 20, 2519-2524. (Pubitemid 30614462)
34. Carrasco, A.; Espinoza, C.; Cardile, V.; Gallardo, C.; Cardona, W.; Lombardo, L.; Catalán, M.; Cuellar, F.; Russo, A. Eugenol and its synthetic analogues inhibit cell growth of human cancer cells. J. Braz. Chem. Soc. 2008, 19, 543-548.
35. Jaganathan, S. K.; Mondhe, D.; Wani, Z. A.; Pal, H. C.; Mandal, M. Effect of honey and eugenol on ehrlich ascites and solid carcinoma. J. Biomed. Biotechnol. 2010, 2010, 989163:1-989163:5.
36. Jaganathan, S. K.; Mazumdar, A.; Mondhe, D.; Mandal, M. Apoptotic effect of eugenol in human colon cancer cell lines. Cell Biol. Int. 2011, 35, 607-615.
37. Sukumaran, K.; Unnikrishnan, M. C.; Kuttan, R. Inhibition of tumour promotion in mice by eugenol. Indian J. Physiol. Pharmacol. 1994, 38, 306-308. (Pubitemid 24370388)
38. Hussain, A.; Priyani, A.; Sadrieh, L.; Brahmbhatt, K.; Ahmed, M.; Sharma, C. Concurrent sulforaphane and eugenol induces differential effects on human cervical cancer cells. Integr. Cancer Ther. 2011, doi:10.1177/1534735411400313.
39. Hussain, A.; Brahmbhatt, K.; Priyani, A.; Ahmed, M.; Rizvi, T. A.; Sharma, C. Eugenol enhances the chemotherapeutic potential of gemcitabine and induces anticarcinogenic and anti-inflammatory activity in human cervical cancer cells. Cancer Biother. Radiopharm. 2011, 26, 519-527.
40. Vidhya, N.; Devaraj, S. N. Induction of apoptosis by eugenol in human breast cancer cells. Indian J. Exp. Biol. 2011, 49, 871-878.