Effect of novel synthesised policosanyl phenolates on lipid oxidation
Zhiqiang Wang, Seung Hwan Hwang, Soon Sung Limhttps://doi.org/10.17221/530/2015-CJFSCitation:Wang Z., Hwan Hwang S., Sung Lim S. (2016): Effect of novel synthesised policosanyl phenolates on lipid oxidation. Czech J. Food Sci., 34: 414-421.
Lipophilic derivatisation of phenolic acids could greatly improve their antioxidant activities and solubility in hydrophobic environments, broadening their applications in food, pharmaceutical, and cosmetic industries. In this study, we conducted enzymatic lipophilisation of eight phenolates with policosanols. Vinyl phenolates were used as intermediates to improve the efficiency of enzymatic lipophilisation; and the yields of policosanyl phenolates were in the range of 1.32–20.58%. The antioxidant activities of the resulting phenolipids were compared using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) assay and linoleic acid peroxidation ferric thiocyanate assay. The synthesised policosanyl phenolates showed lower ABTS radical scavenging capacities (IC50s > 15 mM); whereas they showed high lipid peroxidation inhibitory activities (IC50s of peroxidation value < 0.25 mM). The lipid oxidation inhibitory activities of policosanol phenolates were further evaluated using the total oxidation value in a linoleic acid model system and the thiobarbituric acid reactive substances value in a cooked pork model system. Finally, policosanyl 4-hydroxybenzoate, policosanyl syringate, and policosanyl 4-hydroxyphenylacetate showed the highest inhibition effects on lipid oxidation and a potential for use as lipid antioxidants.Keywords:
Novozyme 435; lipophilisation; policosanols; phenolic acids; antioxidanReferences:
Berthold Heiner K., Unverdorben Susanne, Degenhardt Ralf, Bulitta Michael, Gouni-Berthold Ioanna (2006): Effect of Policosanol on Lipid Levels Among Patients With Hypercholesterolemia or Combined Hyperlipidemia. JAMA, 295, 2262- https://doi.org/10.1001/jama.295.19.2262Buettner G.R. (1993): The Pecking Order of Free Radicals and Antioxidants: Lipid Peroxidation, α-Tocopherol, and Ascorbate. Archives of Biochemistry and Biophysics, 300, 535-543 https://doi.org/10.1006/abbi.1993.1074Chaiyasit Wilailuk, Elias Ryan J., McClements D. Julian, Decker Eric A. (2007): Role of Physical Structures in Bulk Oils on Lipid Oxidation. Critical Reviews in Food Science and Nutrition, 47, 299-317 https://doi.org/10.1080/10408390600754248Chigorimbo-Murefu Nyaradzo T.L., Riva Sergio, Burton Stephanie G. (2009): Lipase-catalysed synthesis of esters of ferulic acid with natural compounds and evaluation of their antioxidant properties. Journal of Molecular Catalysis B: Enzymatic, 56, 277-282 https://doi.org/10.1016/j.molcatb.2008.05.017Decker E.A. (1998): Strategies for manipulating the prooxidative/antioxidative balance of foods to maximize oxidative stability. Trends in Food Science & Technology, 9: 241–248.Decker E., Elias R., McClements D.J. (eds) (2010): Oxidation in foods and beverages and antioxidant applications. Vols 1 & 2. Cambringe, Woodhead Publishing.Figueroa-Espinoza Maria-Cruz, Villeneuve Pierre (2005): Phenolic Acids Enzymatic Lipophilization. Journal of Agricultural and Food Chemistry, 53, 2779-2787 https://doi.org/10.1021/jf0484273Fu Yuanqing, Zhang Yan, Hu Huiying, Chen Ying, Wang Rong, Li Duo, Liu Songbai (2014): Design and straightforward synthesis of novel galloyl phytosterols with excellent antioxidant activity. Food Chemistry, 163, 171-177 https://doi.org/10.1016/j.foodchem.2014.04.093Irmak Sibel, Dunford Nurhan Turgut, Milligan Jeff (2006): Policosanol contents of beeswax, sugar cane and wheat extracts. Food Chemistry, 95, 312-318 https://doi.org/10.1016/j.foodchem.2005.01.009Ito N., Hirose M., Fukushima S., Tsuda H., Shirai T., Tatematsu M. (1986): Studies on antioxidants: Their carcinogenic and modifying effects on chemical carcinogenesis. Food and Chemical Toxicology, 24, 1071-1082 https://doi.org/10.1016/0278-6915(86)90291-7Kwon H., Shin D.Y., Lee J.H., Kim S.W., Kang J.W. (2007): Molecular modeling and its experimental verification for the catalytic mechanism of Candida antarctica lipase B. Journal of Microbiology and Biotechnology, 17: 1098–1105.Paquot C. (1979): Standard Methods for the Analysis of Oils, Fats and Derivatives. Oxford, Pergamon Press.Re Roberta, Pellegrini Nicoletta, Proteggente Anna, Pannala Ananth, Yang Min, Rice-Evans Catherine (1999): Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26, 1231-1237 https://doi.org/10.1016/S0891-5849(98)00315-3Sakanaka Senji, Tachibana Yumi, Ishihara Noriyuki, Raj Juneja Lekh (2004): Antioxidant activity of egg-yolk protein hydrolysates in a linoleic acid oxidation system. Food Chemistry, 86, 99-103 https://doi.org/10.1016/j.foodchem.2003.08.014Sherwin E. R. (1978): Oxidation and antioxidants in fat and oil processing. Journal of the American Oil Chemists’ Society, 55, 809-814 https://doi.org/10.1007/BF02682653Soobrattee M.A., Neergheen V.S., Luximon-Ramma A., Aruoma O.I., Bahorun T. (2005): Phenolics as potential antioxidant therapeutic agents: Mechanism and actions. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 579, 200-213 https://doi.org/10.1016/j.mrfmmm.2005.03.023Sørensen Ann-Dorit Moltke, Nielsen Nina Skall, Yang Zhiyong, Xu Xuebing, Jacobsen Charlotte (2012): Lipophilization of dihydrocaffeic acid affects its antioxidative properties in fish-oil-enriched emulsions. European Journal of Lipid Science and Technology, 114, 134-145 https://doi.org/10.1002/ejlt.201100002Sun Yue-E, Wang Wei-Dong, Chen Hong-Wei, Li Chao (2011): Autoxidation of Unsaturated Lipids in Food Emulsion. Critical Reviews in Food Science and Nutrition, 51, 453-466 https://doi.org/10.1080/10408391003672086Tan Zhuliang, Shahidi Fereidoon (2011): Chemoenzymatic Synthesis of Phytosteryl Ferulates and Evaluation of Their Antioxidant Activity. Journal of Agricultural and Food Chemistry, 59, 12375-12383 https://doi.org/10.1021/jf2034237Tan Zhuliang, Shahidi Fereidoon (2012): A novel chemoenzymatic synthesis of phytosteryl caffeates and assessment of their antioxidant activity. Food Chemistry, 133, 1427-1434 https://doi.org/10.1016/j.foodchem.2012.02.030Tan Zhuliang, Shahidi Fereidoon (2013): Phytosteryl sinapates and vanillates: Chemoenzymatic synthesis and antioxidant capacity assessment. Food Chemistry, 138, 1438-1447 https://doi.org/10.1016/j.foodchem.2012.10.093Wang Tong, Hicks Kevin B., Moreau Robert (2002): Antioxidant activity of phytosterols, oryzanol, and other phytosterol conjugates. Journal of the American Oil Chemists' Society, 79, 1201-1206 https://doi.org/10.1007/s11746-002-0628-xWang Z., Hwang S.H., Lim S.S. (2015a): Lipophilization of phenolic acids with phytosterols by a chemoenzymatic method to improve their antioxidant activities. European Journal of Lipid Science and Technology, 117: 1037–1048.Wang Z., Hwang S.H., Lim S.S. (2015b): Chemoenzymatically synthesized policosanyl phenolates as autoxidation inhibitors. European Journal of Lipid Science and Technology, 117: 300–310.Whitaker Bruce D., Schmidt Walter F., Kirk Marion C., Barnes Stephen (2001): Novel Fatty Acid Esters of p -Coumaryl Alcohol in Epicuticular Wax of Apple Fruit. Journal of Agricultural and Food Chemistry, 49, 3787-3792 https://doi.org/10.1021/jf010409n