Timokinon, Timol ve Karvakrolün Antioksidan Aktiviteleri ve Lipit Oksidasyonunu Önleme Kapasiteleri

Yıl 2021, Cilt: 52 Sayı: 1, 108 - 118, 26.01.2021

Şeyma Yıldız Semra Turan

https://doi.org/10.17097/ataunizfd.773499

Cited By: 2

Öz

Fenolik bileşikler bitkisel kaynaklı olup, aromatik halkasında bir veya daha fazla hidroksil grubu içeren bileşiklerdir. Bitki uçucu yağlarında bulunan bu bioaktif komponentler, doğal antioksidan kaynakları olmaları, serbest radikalleri inaktive etmeleri, oksidatif stresi azaltmaları sebepleri ile terapötik ajan olarak kullanılmış, farmasötik, kozmetik ve gıda araştırma alanlarında yer almışlardır. Bu derlemede, gıda endüstrisinde sentetik antioksidanlar yerine kullanılabilecek timokinon, timol ve karvakrol fenolik bileşikleri incelenmiştir. Timokinon, dünya tarihinde çeşitli hayvan ve insan rahatsızlıklarının tedavisinde yüzyıllardır kullanılan Nigella sativa L.’nin ana aktif bileşenidir. Timol ve karvakrol farmokolojide yaygın olarak kullanılan kekik ve türevlerinin ana bileşenleri olarak bilinmektedir. Çeşitli araştırmalarda timokinon, timol ve karvakrolün sahip oldukları antioksidan aktiviteleri ile lipit oksidasyonunu önleme ve oksidasyonun olası etkilerini azaltma potansiyelleri incelendiğinden, bu çalışmada bu konuda yapılan çalışmalar özetlenmiştir.

Anahtar Kelimeler

Timokinon, Timol, Karvakrol, Antioksidan aktivite, Lipit oksidasyonu

Destekleyen Kurum

Bolu Abant İzzet Baysal Üniversitesi Bilimsel Araştırma Projeleri Kordinasyon Birimi

Proje Numarası

2018.09.04.1288 numaralı AİBÜ BAP projesi

Antioxidant Activities and Lipid Peroxidation Inhibition Capacities of Thymoquinone, Thmol and Carvacrol

Öz

Phenolic compounds possess an aromatic ring bearing one or more hydroxyl substituent and most are of plant origin. These bioactive components found in plant essential oils have been used as therapeutic agents because they are natural sources of antioxidants, inactivate free radicals, reduce oxidative stress, and have taken place in pharmaceutical, cosmetic and food research fields. In this review, phenolic compounds thymoquinone, thymol and carvacrol that can be used instead of synthetic antioxidants in the food industry were examined. Thymoquinone is the main active ingredient of Nigella sativa L., which has been used for centuries in the treatment of various animal and human ailments in world history. Thymol and carvacrol are known as the main components of thyme and its derivatives, which are widely used in pharmacology. Since various studies have investigated the antioxidant activities of thymoquinone, thymol and carvacrol and their potential to prevent lipid oxidation and to reduce the possible effects of oxidation, the studies conducted on this subject are summarized in this study.

Anahtar Kelimeler

Thymoquinone, Thymol, Carvacrol, Antioxidant activity, Lipid peroxidation

Proje Numarası

2018.09.04.1288 numaralı AİBÜ BAP projesi

Kaynakça

• Aeschbach, R., Löliger, J., Scott, B.C., Murcia, A., Butler, J., Halliwell, B., Aruoma, O.I. (1994). Antioxidant actions of thymol, carvacrol, 6-gingerol, zingerone and hydroxytyrosol. Food and Chemical Toxicology, 32 (1): 31-36.
• Ahmad, S., Beg, Z.H. (2013) Hypolipidemic and antioxidant activities of thymoquinone and limonene in atherogenic suspension fed rats. Food Chemistry, 138 (2-3):1116-1124.
• Ahmad, S., Beg, Z.H. (2016) Evaluation of therapeutic effect of omega-6 linoleic acid and thymoquinone enriched extracts from Nigella Sativa oil in the mitigation of lipidemic oxidative stress in rats. Nutrition, 32 (6):649-655.
• Al-Malki, A.L. (2010) Antioxidant properties of thymol and butylated hydroxytoluene in carbon tetrachloride-induced mice liver injury. Journal of King Abdulaziz University, 22 (1):239.
• Altan, A., Aytac, Z., Uyar, T. (2018) Carvacrol loaded electrospun fibrous films from zein and poly (lactic acid) for active food packaging. Food Hydrocolloids, 81:48-59.
• Aristatile, B., Al‐Numair, K.S., Al‐Assaf, A.H., Veeramani, C., Pugalendi, K.V. (2015) Protective effect of carvacrol on oxidative stress and cellular dna damage induced by uvb irradiation in human peripheral lymphocytes. Journal of Biochemical and Molecular Toxicology, 29 (11):497-507.
• Badary, O.A., Taha, R.A., Gamal El-Din, A.M., Abdel-Wahab, M.H. (2003) Thymoquinone is a potent superoxide anion scavenger. Drug and Chemical Toxicology, 26 (2):87-98.
• Bayaz, M. (2014) Esansiyel yağlar: antimikrobiyal, antioksidan ve antimutajenik aktiviteleri. Akademik Gıda, 12:45-53. Bellés, M., Alonso, V., Roncalés, P., Beltrán, J.A. (2019) Sulfite‐free lamb burger meat: antimicrobial and antioxidant properties of green tea and carvacrol. Journal of the Science of Food and Agriculture, 99 (1):464-472.
• Beydilli, H., Yilmaz, N., Cetin, E.S., Topal, Y., Topal, H., Sozen, H., Cigerci, I.H. (2015) The effects of thymoquinone on nitric oxide and superoxide dismutase levels in a rat model of diazinon-induced brain damage. Studies on Ethno-Medicine, 9 (2):191-195.
• Bourgou, S., Pichette, A., Marzouk, B., Legault J. (2010) Bioactivities of black cumin essential oil and its main terpenes from Tunisia. South African of Botany, 76:210-216.
• Burits, M., Bucar, F. (2000) Antioxidant activity of Nigella Sativa essential oil. Phytotherapy Research, 14 (5):323-328. Çetinkaya, A. (2011) Timol, karvakrol, eugenol ve alfa terpineolun soğukta depolanan vakum paketlenmiş hamsi filetoları üzerine etkilerinin incelenmesi. Doktora Tezi, Çukurova Üniversitesi, Adana, 114 s.
• Çoban, Ö.E., Patır, B. (2010) Antioksidan etkili bazı bitki ve baharatların gıdalarda kullanımı. Gıda Teknolojileri Elektronik Dergisi, 5:7-19. Dairi, N., Ferfera-Harrar, H., Ramos, M., Garrigós, M.C. (2019) Cellulose acetate/agnps-organoclay and/or thymol nano-biocomposite films with combined antimicrobial/antioxidant properties for active food packaging use. International Journal of Biological Macromolecules, 121:508-523.
• Deighton, N., Glidewell, S.M., Deans, S.G., Goodman, B.A. (1993) Identification by EPR spectroscopy of carvacrol and thymol as the major sources of free radicals in the oxidation of plant essential oils. Journal of the Science of Food and Agriculture, 63 (2):221-225.
• Esmaeili, A., Khodadadi, A. (2012) Antioxidant activity of a solution of thymol in ethanol. Zahedan Journal of Research in Medical Sciences, 14 (7):14-18. Gavaric, N., Mozina, S.S., Kladar, N., Bozin, B. (2015) Chemical profile, antioxidant and antibacterial activity of thyme and oregano essential oils, thymol and carvacrol and their possible synergism. Journal of Essential Oil Bearing Plants, 18 (4):1013-1021.
• Guimarães, A.G., Oliveira, G.F., Melo, M.S., Cavalcanti, S.C., Antoniolli, A.R., Bonjardim, L.R., Araújo, A.A. (2010) Bioassay‐guided evaluation of antioxidant and antinociceptive activities of carvacrol. Basic & Clinical Pharmacology & Toxicology, 107 (6):949-957.
• Gursul, S., Karabulut, I., Durmaz, G. (2019) Antioxidant efficacy of thymol and carvacrol in microencapsulated walnut oil triacylglycerols. Food Chemistry, 278:805-810.
• Güllü, E.B., Avcı G. (2013) Timokinon: Nigella Sativa’nın biyoaktif komponenti. Kocatepe Veteriner Dergisi, 6 (1):51-61.
• Güzelsoy, P., Aydın, S., Başaran, N. (2018) Çörekotunun (Nigella Sativa L.) aktif bileşeni timokinonun insan sağlığı üzerine olası etkileri. Journal of Literature Pharmacy Sciences, 7 (2):118-135.
• Hashemipour, H., Kermanshahi, H., Golian, A., Veldkamp, T. (2013) Effect of thymol and carvacrol feed supplementation on performance, antioxidant enzyme activities, fatty acid composition, digestive enzyme activities, and immune response in broiler chickens. Poultry Science, 92 (8):2059-2069.
• Homayouni, H., Kavoosi, G., Nassiri, S.M. (2017) Physicochemical, antioxidant and antibacterial properties of dispersion made from tapioca and gelatinized tapioca starch incorporated with carvacrol. LWT-Food Science and Technology, 77:503-509.
• Horuz, T.İ., Maskan, M. (2015) Effect of the phytochemicals curcumin, cinnamaldehyde, thymol and carvacrol on the oxidative stability of corn and palm oils at frying temperatures. Journal of Food Science and Technology, 52 (12):8041-8049.
• Hosseinzadeh, H., Parvardeh, S., Asl, M.N., Sadeghnia, H.R., Ziaee, T. (2007) Effect of thymoquinone and Nigella Sativa seeds oil on lipid peroxidation level during global cerebral ischemia-reperfusion injury in rat hippocampus. Phytomedicine, 14 (9):621-627.
• Inanc, T., Maskan, M. (2014) Effect of carvacrol on the oxidative stability of palm oil during frying. Grasas y Aceites, 65 (4):042.
• Jiang, Z.S., Pu, Z.C., Hao, Z.H. (2015) Carvacrol protects against spinal cord injury in rats via suppressing oxidative stress and the endothelial nitric oxide synthase pathway. Molecular Medicine Reports, 12 (4):5349-5354.
• Karakaya, S., El, S.N. (1997) Flavonoidler ve sağlık. Beslenme ve Diyet Dergisi, 26(2):54-60.
• Kavoosi, G., Dadfar, S.M.M., Purfard, A.M. (2013a) Mechanical, physical, antioxidant, and antimicrobial properties of gelatin films incorporated with thymol for potential use as nano wound dressing. Journal of Food Science, 78 (2): E244-E250.
• Kavoosi, G., Dadfar, S.M.M., Mohammadi Purfard, A., Mehrabi, R. (2013b) Antioxidant and antibacterial properties of gelatin films incorporated with carvacrol. Journal of Food Safety, 33 (4):423-432.
• Kaya, Ü. (2009) İznik’te yetiştirilen Gemlik zeytininin ve yağının bazı fiziksel, kimyasal ve antioksidan özelliklerinin belirlenmesi. Çukurova Üniversitesi, Fen Bilimleri Enstitüsü, Yüksek Lisans Tezi, Adana.
• Kiralan, M., Bayrak, A. (2005) Bitkisel yağların stabilizasyonunda doğal antioksidanların rolü. Gıda/The Journal of Food, 30: 247-254.
• Kiralan, M. (2014) Changes in volatile compounds of black cumin (Nigella Sativa L.) seed oil during thermal oxidation. International Journal of Food Properties, 17:1482-1489.
• Kiralan, M., Özdemir, N., Özkan, G., Bayrak, A., Ramadan, M.F. (2017) Blends of cold pressed black cumin oil and sunflower oil with improved stability: a study based on changes in the levels of volatiles, tocopherols and thymoquinone during accelerated oxidation conditions. Journal of Food Biochemistry, 41: e12272, 1-10.
• Koca, N., Karadeniz, F. (2005) Gıdalardaki doğal antioksidan bileşikler. Gıda, 30(4):229-236.
• Kolaç, T., Gürbüz, P., Yetiş, G. (2017) Doğal ürünlerin fenolik içeriği ve antioksidan özellikleri. İnönü Üniversitesi Sağlık Hizmetleri Meslek Yüksek Okulu Dergisi, 5 (1):26-42.
• Lucera, A., Mastromatteo, M., Sinigaglia, M., Corbo, M.R. (2009) Combined effects of thymol, carvacrol and grapefruit seed extract on lipid oxidation and colour stability of poultry meat preparations. International Journal of Food Science & Technology, 44 (11):2256-2267.
• López-Mata, M.A., Ruiz-Cruz, S., Silva-Beltrán, N.P., Ornelas-Paz, J.D.J., Zamudio-Flores, P.B., Burruel-Ibarra, S.E. (2013) Physicochemical, antimicrobial and antioxidant properties of chitosan films incorporated with carvacrol. Molecules, 18 (11):13735-13753.
• Luna, A., Labaque, M.C., Zygadlo, J.A., Marin, R.H. (2010) Effects of thymol and carvacrol feed supplementation on lipid oxidation in broiler meat. Poultry Science, 89 (2):366-370.
• Luna, A., Lábaque, M.C., Fernandez, M.E., Zygadlo, J.A., Marin, R.H. (2018) Effects of feeding thymol and isoeugenol on plasma triglycerides and cholesterol levels in japanese quail. JAPS: Journal of Animal & Plant Sciences, 28 (1):56-62.
• Mansour, M.A., Nagi, M.N., El‐Khatib, A.S., Al‐Bekairi, A.M. (2002) Effects of thymoquinone on antioxidant enzyme activities, lipid peroxidation and dt‐diaphorase in different tissues of mice: a possible mechanism of action. Cell Biochemistry and Function, 20 (2):143-151.
• Marin, M., Novakovic, M., Vuckovic, I., Teševic, V., Kolarevic, S., Vukovic-Gacic, B. (2018) Wild thymus capitatus hoff. et link. chemical composition, antioxidant and antimicrobial activities of the essential oil. Journal of Essential Oil Bearing Plants, 21 (2):388-399.
• Mastelıć, J., Jerkovıć, I., Blaževıć, I., Poljak-Blažı, M., Borovı´, S., Ivancˇıc´-Bac´e, SmrecˇKı, V. (2008) Comparative study on the antioxidant and biological activities of carvacrol, thymol, and eugenol derivatives. Journal of Agricultural and Food Chemistry, 56 (11):3989-3996.
• Meral, R., Doğan, İ.S., Kanberoğlu, G.S. (2012) Fonksiyonel gıda bileşeni olarak antioksidanlar. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 2 (2):45-50.
• Milovanovic, S., Stamenic, M., Markovic, D., Radetic, M., Zizovic, I. (2013) Solubility of thymol in supercritical carbon dioxide and its impregnation on cotton gauze. The Journal of Supercritical Fluids, 84:173-181.
• Nagi, M.N., Mansour, M.A. (2000) Protective effect of thymoquinone against doxorubicin–induced cardiotoxicity in rats: a possible mechanism of protection. Pharmacological Research, 41 (3):283-289.
• Nagoor Meeran, M.F., Stanely Mainzen Prince, P. (2012) Protective effects of thymol on altered plasma lipid peroxidation and nonenzymic antioxidants in isoproterenol‐induced myocardial infarcted rats. Journal of Biochemical and Molecular Toxicology, 26 (9):368-373.
• Quiroga, P.R., Asensio, C.M., Nepote, V. (2015) Antioxidant effects of the monoterpenes carvacrol, thymol and sabinene hydrate on chemical and sensory stability of roasted sunflower seeds. Journal of the Science of Food and Agriculture, 95 (3):471-479.
• Ramos, M., Jiménez, A., Peltzer, M., Garrigós, M.C. (2014a) Development of novel nano-biocomposite antioxidant films based on poly (lactic acid) and thymol for active packaging. Food chemistry, 162:149-155.
• Ramos, M., Beltrán, A., Peltzer, M., Valente, A.J., del Carmen Garrigós, M. (2014b) Release and antioxidant activity of carvacrol and thymol from polypropylene active packaging films. LWT-Food Science and Technology, 58 (2):470-477.
• Safaei-Ghomi, J., Ebrahimabadi, A.H., Djafari-Bidgoli, Z., Batooli, H. (2009) GC/MS analysis and in vitro antioxidant activity of essential oil and methanol extracts of thymus caramanicus jalas and its main constituent carvacrol. Food Chemistry, 115 (4):1524-1528.
• Sharifi‐Rad, M., Varoni, E.M., Iriti, M., Martorell, M., Setzer, W.N., del Mar Contreras, M., Sharifi‐Rad, J. (2018) Carvacrol and human health: a comprehensive review. Phytotherapy Research, 32 (9), 1675-1687.
• Söylemezoğlu, G. (2003) Üzümde fenolik bileşikler. Gıda, 28(3):277-285.
• Stanojević, L.P., Stanojević, J.S., Cvetković, D.J., Ilić, D.P. (2018) Antioxidant activity of oregano essential oil (Origanum vulgare L.). Biologica Nyssana, 7 (2):131-139.
• Su, G., Zhou, X., Wang, Y., Chen, D., Chen, G., Li, Y., He, J. (2018) Effects of plant essential oil supplementation on growth performance, immune function and antioxidant activities in weaned pigs. Lipids in Health and Disease, 17 (1):139.
• Taborsky, J., Kunt, M., Kloucek, P., Lachman, J., Zeleny, V., Kokoska L. (2012) Identification of potential sources of thymoquinone and related compounds in Asteraceae, Cupressaceae, Lamiaceae, and Ranunculaceae families. Central European Journal of Chemistry, 10:1899-1906.
• Tchuenchieu, A., Essia Ngang, J.J., Servais, M., Dermience, M., Sado Kamdem, S., Etoa, F.X., Sindic, M. (2018) Effect of low thermal pasteurization in combination with carvacrol on color, antioxidant capacity, phenolic and vitamin c contents of fruit juices. Food science & nutrition, 6 (4):736-746.
• Tepe, B., Sokmen, M., Akpulat, H.A., Daferera, D., Polissiou, M., Sokmen, A. (2005) Antioxidative activity of the essential oils of Thymus sipyleus subsp. sipyleus var. sipyleus and Thymus sipyleus subsp. sipyleus var rosulans. Journal of Food Engineering, 66:447-454.
• Turhan, S., Üstün, N.Ş. (2006) Doğal antioksidanlar ve gıdalarda kullanımı. Türkiye 9. Gıda Kongresi, Mayıs 24-26, 2006, Bolu, 273-276.
• Yanishlieva, N.V., Marinova, E.M., Gordon, M.H., Raneva, V.G. (1999) Antioxidant activity and mechanism of action of thymol and carvacrol in two lipid systems. Food Chemistry, 64 (1):59-66.
• Yılmaz, D.Ç. (2010) Flavonoidlerin ve metal komplekslerinin yüksek basınçlı sıvı kromatografisi yöntemiyle yan yana belirlenmesi. Marmara Üniversitesi, Sağlık Bilimleri Enstitüsü, Analitik Kimya Anabilim Dalı, Doktora Tezi, İstanbul.
• Yuan, G., Lv, H., Yang, B., Chen, X., Sun, H. (2015) Physical properties, antioxidant and antimicrobial activity of chitosan films containing carvacrol and pomegranate peel extract. Molecules, 20 (6):11034-11045.
• Zhu, P., Chen, Y., Fang, J., Wang, Z., Xie, C., Hou, B., Xu, F. (2016) Solubility and solution thermodynamics of thymol in six pure organic solvents. The Journal of Chemical Thermodynamics, 92:198-206.