Optimisation of microwave-assisted extraction of triterpenoic acids from olive mill waste using response surface methodology
Main Article Content
Keywords
extraction, oleanolic acid, olive pomace, maslinic acid
Abstract
Maslinic acid (MA) and oleanolic acid (OA) are pentacyclic triterpenic phytochemicals found in the olive fruit and leaves as well as wastes. Dried olive pomace is a good source of both triterpenic acids. This study aimed to investigate the potential of microwave-assisted extraction (MAE) to obtain MA and OA from olive pomace and to optimise the MAE process temperature and time by response surface methodology (RSM). The model produced for each compound showed high adequacy to predict the experimental results, hence, the conditions for each triterpenic acid were optimised. The optimal condition for MA extraction was 40 °C for 10 min, whilst OA had optimal extraction at 40 °C for 2.93 min. Compared to conventional Soxhlet extraction, MAE is a promising method to produce MA and OA rich extracts from olive pomace. Also, RSM is a relevant and accurate tool to optimise the MAE parameters.
References
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Allouche, Y., Warleta, F., Campos, M., Sánchez-Quesada, C., Uceda, M., Beltrán, G. and Gaforio, J.J., 2011. Antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage. Journal of Agricultural and Food Chemistry 59: 121-130.
Azbar, N., Bayram, A., Filibeli, A., Muezzinoglu, A., Sengul, F. and Ozer, A., 2004. A review of waste management options in olive oil production. Critical Reviews in Environmental Science and Technology 34: 209-247.
Bianchi, G., Pozzi, N. and Vlahov, G., 1994. Pentacyclic triterpene acids in olives. Phytochemistry 37: 205-207.
Braga, F., Ayres-Saraiva, D., Gattass, C.R. and Capella, M.A.M., 2007. Oleanolic acid inhibits the activity of the multidrug resistance protein ABCC1 (MRP1) but not of the ABCB1 (P-glycoprotein): possible use in cancer chemotherapy. Cancer Letters 248: 147-152.
Cacace, J.E. and Mazza, G., 2002. Extraction of anthocyanins and other phenolics from black currants with sulfured water. Journal of Agricultural and Food Chemistry 50: 5939-5946.
Cacace, J.E. and Mazza, G., 2003a. Mass transfer process during extraction of phenolic compounds from milled berries. Journal of Food Engineering 59: 379-389.
Cacace, J.E. and Mazza, G., 2003b. Optimization of extraction of anthocyanins from black currants with aqueous ethanol. Journal of Food Science 68: 240-248.
Camel, V., 2000. Microwave-assisted solvent extraction of environmental samples. Trends in Analytical Chemistry 19: 229-248.
De Pablos, L., Dos Santos, M., Montero, E., Garcia-Granados, A., Parra, A. and Osuna, A., 2010. Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens. Parasitology Research 107: 601-604.
Fu, Q., Zhang, L., Cheng, N., Jia, M. and Zhang, Y., 2014. Extraction optimization of oleanolic and ursolic acids from pomegranate (Punica granatum L.) flowers. Food and Bioproducts Processing 92: 321-327.
Goulas, V. and Manganaris, G.A., 2012. Towards an efficient protocol for the determination of triterpenic acids in olive fruit: a comparative study of drying and extraction methods. Phytochemical Analysis 23: 444-449.
Guan, T., Qian, Y., Tang, X., Huang, M., Huang, L., Li, Y. and Sun, H., 2011. Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation. Journal of Neuroscience Research 89: 1829-1839.
Horiuchi, K., Shiota, S., Hatano, T., Yoshida, T., Kuroda, T. and Tsuchiya, T., 2007. Antimicrobial activity of oleanolic acid from Salvia officinalis and related compounds on Vancomycin-Resistant Enterococci (VRE). Biological and Pharmaceutical Bulletin 30: 1147-1149.
Instituto Espanol de Normalizacion, 1973. UNE 55020.
Juan, M.E., Planas, J.M., Ruiz-Gutierrez, V., Daniel, H. and Wenzel, U., 2008. Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells. British Journal of Nutrition 100: 36-43.
Kombargi, W.S., Michelakis, S.E. and Petrakis, C.A., 1998. Effect of olive surface waxes on oviposition by Bactrocera oleae (Diptera: Tephritidae). Journal of Economic Entomology 91: 993-998.
Kurtulu?, E. and Günerhan, H., 2003. Prinan?n bir yak?t olarak kullan?m? ve eldesi. yeni ve yenilenebilirenerji kaynaklar? sempozyumu ve sergisi bildiriler kitab?, makine mühendisleri odas?. Yay?n No E/2003/330, Kayseri, Turkey, pp. 105-114.
Li, C., Yang, Z., Zhai, C., Qiu, W., Li, D., Yi, Z., Wang, L., Tang, J., Qian, M. and Luo, J., 2010. Maslinic acid potentiates the anti-tumor activity of tumor necrosis factor a by inhibiting NF-kB signaling pathway. Molecular Cancer 9: 1-13.
Liu, J., Sun, H., Duan, W., Mu, D. and Zhang, L., 2007. Maslinic acid reduces blood glucose in KK-Ay mice. Biological and Pharmaceutical Bulletin 30: 2075-2078.
Liyana-Pathirana, C. and Shahidi, F., 2005. Optimization of extraction of phenolic compounds from wheat using response surface methodology. Food Chemistry 93: 47-56.
Mandal, V. and Mandal, S.C., 2010. Design and performance evaluation of a microwave based low carbon yielding extraction technique for naturally occurring bioactive triterpenoid: oleanolic acid. Biochemical Engineering Journal 50: 63-70.
Myers, R.H., Montgomery, D.C. and Anderson-Cook, C.M., 2009. Response surface methodology: process and product optimization using designed experiments. Wiley, Hoboken, NJ, USA.
Nasopoulou, C. and Zabetakis, I., 2013. Agricultural and aquacultural potential of olive pomace: a review. Journal of Agricultural Science 5: 116-127.
Öcal, A., 2005. Zeytinya?? at?k suyu ve pirinan?n bitki yeti?tirilmesinde kullan?m olanaklar?n?n anla??lmas?. Çukuroava Üniversitesi fen Bilimleri Enstitüsü, Yüksek Lisans Tezi, Adana, Turkey.
Parra, A., Lopez, P.E. and Garcia-Granados, A., 2010. Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry. Chemistry and Biodiversity 7: 421-439.
Petronelli, A., Pannitteri, G. and Testa, U., 2009. Triterpenoids as new promising anticancer drugs. Anti-Cancer Drugs 20: 880-892.
Roig, A., Cayuela, M.L. and Sánchez-Monedero, M.A., 2006. An overview on olive mill wastes and their valorisation methods. Waste Management 26: 960-969.
Tang, X.-Z., Guan, T., Qian, Y.-S., Li, Y.-M., Sun, H.-B., Huang, J.-H. and Zhang, Y., 2008. Effects of maslinic acid as a novel glycogen phosphorylase inhibitor on blood glucose and hepatic glycogen in mice. Chinese Journal of Natural Medicines 6: 53-56.
Allouche, Y., Jiménez, A., Uceda, M., Paz Aguilera, M., Gaforio, J.J. and Beltrán, G., 2010. Influence of olive paste preparation conditions on virgin olive oil triterpenic compounds at laboratory-scale. Food Chemistry 119: 765-769.
Allouche, Y., Warleta, F., Campos, M., Sánchez-Quesada, C., Uceda, M., Beltrán, G. and Gaforio, J.J., 2011. Antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage. Journal of Agricultural and Food Chemistry 59: 121-130.
Azbar, N., Bayram, A., Filibeli, A., Muezzinoglu, A., Sengul, F. and Ozer, A., 2004. A review of waste management options in olive oil production. Critical Reviews in Environmental Science and Technology 34: 209-247.
Bianchi, G., Pozzi, N. and Vlahov, G., 1994. Pentacyclic triterpene acids in olives. Phytochemistry 37: 205-207.
Braga, F., Ayres-Saraiva, D., Gattass, C.R. and Capella, M.A.M., 2007. Oleanolic acid inhibits the activity of the multidrug resistance protein ABCC1 (MRP1) but not of the ABCB1 (P-glycoprotein): possible use in cancer chemotherapy. Cancer Letters 248: 147-152.
Cacace, J.E. and Mazza, G., 2002. Extraction of anthocyanins and other phenolics from black currants with sulfured water. Journal of Agricultural and Food Chemistry 50: 5939-5946.
Cacace, J.E. and Mazza, G., 2003a. Mass transfer process during extraction of phenolic compounds from milled berries. Journal of Food Engineering 59: 379-389.
Cacace, J.E. and Mazza, G., 2003b. Optimization of extraction of anthocyanins from black currants with aqueous ethanol. Journal of Food Science 68: 240-248.
Camel, V., 2000. Microwave-assisted solvent extraction of environmental samples. Trends in Analytical Chemistry 19: 229-248.
De Pablos, L., Dos Santos, M., Montero, E., Garcia-Granados, A., Parra, A. and Osuna, A., 2010. Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens. Parasitology Research 107: 601-604.
Fu, Q., Zhang, L., Cheng, N., Jia, M. and Zhang, Y., 2014. Extraction optimization of oleanolic and ursolic acids from pomegranate (Punica granatum L.) flowers. Food and Bioproducts Processing 92: 321-327.
Goulas, V. and Manganaris, G.A., 2012. Towards an efficient protocol for the determination of triterpenic acids in olive fruit: a comparative study of drying and extraction methods. Phytochemical Analysis 23: 444-449.
Guan, T., Qian, Y., Tang, X., Huang, M., Huang, L., Li, Y. and Sun, H., 2011. Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation. Journal of Neuroscience Research 89: 1829-1839.
Horiuchi, K., Shiota, S., Hatano, T., Yoshida, T., Kuroda, T. and Tsuchiya, T., 2007. Antimicrobial activity of oleanolic acid from Salvia officinalis and related compounds on Vancomycin-Resistant Enterococci (VRE). Biological and Pharmaceutical Bulletin 30: 1147-1149.
Instituto Espanol de Normalizacion, 1973. UNE 55020.
Juan, M.E., Planas, J.M., Ruiz-Gutierrez, V., Daniel, H. and Wenzel, U., 2008. Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells. British Journal of Nutrition 100: 36-43.
Kombargi, W.S., Michelakis, S.E. and Petrakis, C.A., 1998. Effect of olive surface waxes on oviposition by Bactrocera oleae (Diptera: Tephritidae). Journal of Economic Entomology 91: 993-998.
Kurtulu?, E. and Günerhan, H., 2003. Prinan?n bir yak?t olarak kullan?m? ve eldesi. yeni ve yenilenebilirenerji kaynaklar? sempozyumu ve sergisi bildiriler kitab?, makine mühendisleri odas?. Yay?n No E/2003/330, Kayseri, Turkey, pp. 105-114.
Li, C., Yang, Z., Zhai, C., Qiu, W., Li, D., Yi, Z., Wang, L., Tang, J., Qian, M. and Luo, J., 2010. Maslinic acid potentiates the anti-tumor activity of tumor necrosis factor a by inhibiting NF-kB signaling pathway. Molecular Cancer 9: 1-13.
Liu, J., Sun, H., Duan, W., Mu, D. and Zhang, L., 2007. Maslinic acid reduces blood glucose in KK-Ay mice. Biological and Pharmaceutical Bulletin 30: 2075-2078.
Liyana-Pathirana, C. and Shahidi, F., 2005. Optimization of extraction of phenolic compounds from wheat using response surface methodology. Food Chemistry 93: 47-56.
Mandal, V. and Mandal, S.C., 2010. Design and performance evaluation of a microwave based low carbon yielding extraction technique for naturally occurring bioactive triterpenoid: oleanolic acid. Biochemical Engineering Journal 50: 63-70.
Myers, R.H., Montgomery, D.C. and Anderson-Cook, C.M., 2009. Response surface methodology: process and product optimization using designed experiments. Wiley, Hoboken, NJ, USA.
Nasopoulou, C. and Zabetakis, I., 2013. Agricultural and aquacultural potential of olive pomace: a review. Journal of Agricultural Science 5: 116-127.
Öcal, A., 2005. Zeytinya?? at?k suyu ve pirinan?n bitki yeti?tirilmesinde kullan?m olanaklar?n?n anla??lmas?. Çukuroava Üniversitesi fen Bilimleri Enstitüsü, Yüksek Lisans Tezi, Adana, Turkey.
Parra, A., Lopez, P.E. and Garcia-Granados, A., 2010. Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry. Chemistry and Biodiversity 7: 421-439.
Petronelli, A., Pannitteri, G. and Testa, U., 2009. Triterpenoids as new promising anticancer drugs. Anti-Cancer Drugs 20: 880-892.
Roig, A., Cayuela, M.L. and Sánchez-Monedero, M.A., 2006. An overview on olive mill wastes and their valorisation methods. Waste Management 26: 960-969.
Tang, X.-Z., Guan, T., Qian, Y.-S., Li, Y.-M., Sun, H.-B., Huang, J.-H. and Zhang, Y., 2008. Effects of maslinic acid as a novel glycogen phosphorylase inhibitor on blood glucose and hepatic glycogen in mice. Chinese Journal of Natural Medicines 6: 53-56.
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Oct 10, 2016
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