A STUDY ON THE CHEMICAL PROPERTIES OF EUGENOL AND EUGENOL ACETATE, CLOVE ESSENTIAL OILS

Year 2016, Volume: 34 Issue: 3, 406 - 414, 01.09.2016

Faik Gökalp

Abstract

Eugenol and eugenol acetate are a clove essential oil getting from hydrodistilltion of Syzygium aromaticum’s buds and leaves. It has antimicrobial, antioxidant, analgesic, anticancer activities and used for protecting foods from microorganisms , used as tradational medicine. Eugenol is eager to dissolve in blood and give reaction to radicalic forms of other moleculues. Because of that; It slows cancer cells formation by preventing the radicalic damage.

Keywords

Clove, eugenol, eugenol acetate, DFT and HF

References

• [1] Barceloux, D.G., Foods, Fungi, Medicinal Herbs, Plants and Venemous Animals, Medical Toxicology of Natural Substances, (2008), Hoboken,NJ, USA.
• [2] Harborne, J.B.,Baxter, H., Taylor and Francis, Phytochemical Chemistry, (1963), London, UK.
• [3] Zheng,G.Q., Kenney, P.M.,Lam, L.K.T., Sesquiterpenes from clove, J.Nat.Prod., (1992), 55,999-1003.
• [4] Miyazawa, M., H, İsama,M., Suppression of chemical mutagen-induced SOS response by alkylphenols from clove in Salmonella typhimurium, J.Agric. Food Chem., 2001, 49, 4019-4025.
• [5] Ogendo, J.O., Kostyukovsky, M., Ravid,U.,Matasyoh,J.C., Deng,A.L.,Omolo,E.O., Kariuki,S.T.,Shaya, E., Bioactivity of Ocimum Gratissimum L.. Oil and Two Of Its Constituents Against Five İnsect Pests Attacking Stored Food Products, J.Stored Prod.Res., (2008), 44, 328-334.
• [6] Lean, L.P.,Suhaila, M., Antioxidative and Antimycotic effect of turmeric, lemon-grass, Betelleaves, Clove, Black Papper Leaves and Garcinia Atriviridis on butter cakes, Journal of the Science of Food and Agriculture,(1999), 79, 1817–1822.
• [7] Lee, K.G. and Shibamoto, T., Antioxidant property of aroma extract isolated from clove buds [Syzygium aromaticum (L.) Merr. et Perry] Food Chemistry, (2001)74, 443–448.
• [8] Yanishlieva, N.V., Marinova, E.M., Stabilisation of edible oils with natural antioxidants. Eur.Jurnal Lipid Science Technol, (2001), 103, 752-767.
• [9] Shahidi, F., Pegg,R.B. and Saleemi Z.O., Stabilization of meat lipids with ground spices. J Food Lipids, (1995), 2, 145–153.
• [10] Yogalakshmi, B., Viswanathan, P., Anuradha, C.V., Investigation Of Antioxidant, Antiinflammatory and DNA Protective Proporties of Eugenol in Thioacetamide induced liver injury in rats, Toxicology, (2010), 268,204-212.
• [11] Hussain, A.,Brahmbhatt, K., Priyani,A., Ahmet, 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 Biotherapy Radiopharm, (2011), 26(5), 519-527.
• [12] Jaganathan,S.K., Mazumdar, A.,Mondhe, D.,Mandal, M., Apoptotic Effect Of Eugenol In Human Colon Cancer Cell Lines, Cell Biol. Int., (2011), 35(6),607-615.
• [13] 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(1), 41-52.
• [14] 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), 18, 5812-5829.
• [15] Ghosh,R.,Ganapathy,M.,Alworth,W.L.,Chan,D.C., Kumar, A.P., Combination Of 2-methoxyestradiol and Eugenol For Apoptosis Induction Synergistically In Androgen Independent Prostate Cancer Cells, J.Steroid Biochem.Mol.Biol., (2009), 113, 25-35.
• [16] Guy, P.,Kmatou,I.,Vermaak,Alvaro,M.V., Eugenol From The Remote Maluku Islands To The International Market Place: A Review Of A Remarkable And Versatile Molecule, Molecules, (2012), 17, 6953-6981.
• [17] Seema-Farhath, M.S., Vijaya,P.P., Mumtaj,P., Vimal,M., A Comparative Study On Antioxidant Activity Of Essential Oils And Curcumin Using Thiobarbuturic Acid, Reactive Substances, (2013), 5(9):219-221.
• [18] Misharina, T. A. Alinkina, E. S. and Medvedeva, I. B, Antiradical Properties of Essential Oils and Extracts from Clove Bud and Pimento, Applied Biochemistry and Microbiology, (2015), 51(1):119–124.
• [19] K. Fukui, Role of Frontier Orbitals in Chemical Reactions, Science, (1982), 218:747-754.
• [20] R. Pearson, Absolute electronegativity and hardness: applications to organic chemistry, J. Org.Chem., (1989), 54:1423-1430.
• [21] Uysal,Ü.D., A DFT Study of Biogenic Amines,AKU J.Sci., (2012), 12(011202):11-24.
• [22] Günay,N., Pir,H., Atalay,Y., L-Asparaginyum Pikrat Molekülünün Spektroskopik Özelliklerinin Teorik Olarak İncelenmesi, SAÜ J.Sci, (2011), (1).
• [23] Pearson, R.,Absolute electronegativity and hardness: applications to organic chemistry, J. Org.Chem., (1989), 54:1423-1430.
• [24] Pearson, R. G. Proceeding of the National Academiy of Sciences, (1986), 83:8440-8441.
• [25] Gomez, B., Likhanova, N.V., Dominguez-Aguilar, M.A., et al., Theoretical Study of a New Group of Corrosion Inhibitors, Journal of Physical Chemistry A, (2005), 109, 8950-8957.
• [26] Chattaraj, P.K., Chemical Reactivity Theory: A Density Functional View, (2009), 610, CRC Press, New York.
• [27] Eşme A., Sağdınç S. G., The linear, nonlinear optical properties and quantum chemical parameters of some sudan dyes, BAÜ J.Sci, (2014), 16(1) 47-75.
• [28] Gökalp, F., A theoritical study of Curcuma longa’s anticancer agents, curcumin I and curcumin II, ın blood and gas by using density functional theory (DFT) and hartree–fock (HF), International Journal of Medicine and Medical Sciences, (2014), 6, 146-150.
• [29] Ha,T.K.,Q., Dao,T.T., Nguyen,N.H., Kim,J., Kim,E., Antiviral phenolics from the leaves of Cleistocalyx operculatus, Fitoterapia 110 (2016) 135–141.