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Lipase-Catalyzed Acidolysis of Olive Oil with Echium Oil Stearidonic Acid: Optimization by Response Surface Methodology

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Journal of the American Oil Chemists' Society

Abstract

In this study, our aim was to enrich olive oil with stearidonic acid (SDA) together with polyunsaturated fatty acids (PUFA) by lipase-catalyzed acidolysis using olive oil (OO) and free fatty acids of Echium oil, in the presence of Lipozyme® TL IM. The reaction conditions were optimized by using response surface methodology. A three-factor, five level central composite circumscribed designs was used to generate the design points. The factors chosen were: substrate molar ratio (S r, 4–6 mol/mol), reaction temperature (T, 55–65 °C), and reaction time (t, 6–9 h). Targeted incorporation (5 %) of SDA into OO was achieved at substrate molar ratio of 6 mol/mol, 55 °C, and 8.4 h. Model verification performed under these conditions for mg- and g-scale production yielded SDA contents of 4.9 and 4.8 %, respectively. Moreover, it was observed that the structured lipid (SL) obtained under optimum conditions contained approximately 42 % oleic acid and 43 % PUFA including linoleic acid, α-linolenic acid, and γ-linolenic acid. Omega-6/omega-3 fatty acid ratio of SLs was 0.7. Analysis of oxidative properties resulted in lower oxidative stability of SL than unmodified OO. This type of SL containing SDA and other PUFA is believed to be beneficial for human health.

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References

  1. Coupland K (2008) Stearidonic acid: a plant produced omega-3 PUFA and a potential alternative for marine oil fatty acids. Lipid Tech 20:152–154

    Article  CAS  Google Scholar 

  2. Anon (2010) WHO & FAO joint consultation fats and oils in human nutrition. Report of an expert consultation. FAO food and nutrition, paper 91

  3. Gomez-Candela C, Bermejo López LM, Loria Kohen V (2011) Importance of a balanced omega 6/omega 3 ratio for the maintenance of health nutritional recommendations. Nutr Hosp 26:323–329

    CAS  Google Scholar 

  4. Simopoulos AP (2006) Evolutionary aspects of diet, the omega-6/omega-3 ratio and genetic variation: nutritional implications for chronic diseases. Biomed Pharmacother 60:502–507

    Article  CAS  Google Scholar 

  5. Ruiz-Lopez N, Haslam RP, Venegas-Caleron M, Larson TR, Graham IA, Napier JA, Sayanova O (2009) The synthesis and accumulation of stearidonic acid in transgenic plants: a novel source of ‘heart-healthy’ omega-3 fatty acids. Plant Biotechnol J 7:704–716

    Article  CAS  Google Scholar 

  6. Yıldırım A, Ekin T (2003) Orta Anadolu Bölgesi Yabancı Ot Florası. Bitki Koruma Bülteni 43:1–98

    Google Scholar 

  7. Nogala-Kalucka M, Rudzinska M, Zadernowski R, Siger A, Krzyzostaniak I (2010) Phytochemical content and antioxidant properties of seeds of unconventional oil plants. J Am Oil Chem Soc 87:1481–1487

    Article  CAS  Google Scholar 

  8. Tardío J, Pardo-De-Santayana M, Morales R (2006) Ethnobotanical review of wild edible plants in Spain. Bot J Linn Soc 152:27–71

    Article  Google Scholar 

  9. Czaplicki S, Zadernowski N, Ogrodowska D (2009) Triacylglycerols from viper bugloss (Echium vulgare L.) seed bio-oil. Eur J Lipid Sci Technol 111:1266–1269

    Article  CAS  Google Scholar 

  10. Guil-Guerrero JL (2007) Stearidonic acid (18:4n-3): metabolism, nutritional importance, medical uses and natural source. Eur J Lipid Sci Technol 109:1226–1236

    Article  CAS  Google Scholar 

  11. Senanayake SPJ, Shahidi F (1999) Enzymatic incorporation of docosahexaenoic acid into borage oil. J Am Oil Chem Soc 76:1009–1015

    CAS  Google Scholar 

  12. Pina-Rodriguez AM, Akoh CC (2009) Enrichment of amaranth oil with ethyl palmitate at the sn-2 position by chemical and enzymatic synthesis. J Agric Food Chem 57:4657–4662

    Article  CAS  Google Scholar 

  13. Lee JH, Shin JA, Lee JH, Lee KT (2004) Production of lipase-catalyzed structured lipids from safflower oil with conjugated linoleic acid and oxidation studies with rosemary extracts. Food Res Int 37:967–974

    Article  CAS  Google Scholar 

  14. Lee JH, Lee KT, Akoh CC, Chung SK, Kim MR (2006) Antioxidant evaluation and oxidative stability of structured lipids from extra virgin olive oil and conjugated linoleic acid. J Agric Food Chem 54:5416–5421

    Article  CAS  Google Scholar 

  15. Akoh CC, Moussata CO (2001) Characterization and oxidative stability of enzymatically produced fish and canola oil-based structured lipids. J Am Oil Chem Soc 78:25–30

    Article  CAS  Google Scholar 

  16. AOCS Official Method Cd 8b-90 and 18-90 (2009) Official methods and recommended practices of the American Oil Chemists’ Society. In: Firestone D (ed) 6th edn. American Oil Chemists’ Society, Champaign

  17. Shahidi F, Wanasundra UN (2002) Methods for measuring oxidative rancidity in fats and oils. In: Akoh CC, Min DB (eds) Food lipids chemistry, nutrition and biotechnology. CRC Press, New York, pp 465–487

    Google Scholar 

  18. Chopra R, Rastogi NK, Sambaiah K (2009) Enrichment of rice bran oil with α-linolenic acid by enzymatic acidolysis: optimization of parameters by response surface methodology. Food Bioprocess Tech 4:1153–1163

    Article  Google Scholar 

  19. Lumor SE, Akoh CC (2005) Enzymatic incorporation of stearic acid into a blend of palm olein and palm kernel oil: optimization by response surface methodology. J Am Oil Chem Soc 82:412–426

    Article  Google Scholar 

  20. Aranda F, Gomez-Alonso S, Rivera del Alamo RM, Salvador MD, Fregapane G (2004) Triglyceride, total and 2-position fatty acid composition of Cornicabra virgin olive oil: comparison with other Spanish cultivars. Food Chem 86:485–492

    Article  CAS  Google Scholar 

  21. Yang T, Xu X, He C, Li L (2003) Lipase-catalyzed modification of lard to produce human milk fat substitutes. Food Chem 80:473–481

    Article  CAS  Google Scholar 

  22. Maduko CO, Park YW, Akoh CC (2007) Enzymatic production of infant milk fat analogs containing palmitic acid: optimization of reactions by response surface methodology. J Dairy Sci 90:2147–2154

    Article  CAS  Google Scholar 

  23. Maduko CO, Park YW, Akoh CC (2008) Characterization and oxidative stability of structured lipids: infant milk fat analog. J Am Oil Chem Soc 85:197–204

    Article  CAS  Google Scholar 

  24. Osborn HT, Akoh CC (2003) Effect of emulsifier type, droplet size, and oil concentration on lipid oxidation in structured lipid based oil-in-water emulsions. Food Chem 84:451–456

    Article  Google Scholar 

  25. Martin D, Reglero G, Señoráns FJ (2010) Oxidative stability of structured lipids. Eur Food Res Technol 231:635–653

    Article  CAS  Google Scholar 

  26. Nielsen N, Xu X, Timm-Heinrich M, Jacobsen C (2004) Oxidative stability during storage of structured lipids produced from fish oil and caprylic acid. J Am Oil Chem Soc 81:375–383

    Article  CAS  Google Scholar 

  27. Bartee SD, Kim HJ, Min DB (2007) Effects of antioxidants on the oxidative stability of oils containing arachidonic, docosapentaenoic and docosahexaenoic acids. J Am Oil Chem Soc 84:363–368

    Article  CAS  Google Scholar 

  28. Rocha-Uribe A, Hernandez E (2008) Effect of conjugated linoleic acid and fatty acid positional distribution on physicochemical properties of structured lipids. J Am Oil Chem Soc 85:997–1004

    Article  CAS  Google Scholar 

  29. Jennings B, Akoh C (2009) Characterization of a rice bran oil structured lipid. J Agric Food Chem 57:3346–3350

    Article  CAS  Google Scholar 

  30. Kahveci D, Can A, Ozcelik B (2009) Production of lipase-catalyzed structured lipid from olive oil with omega-3 polyunsaturated fatty acids. Food Sci Biotechnol 18:79–83

    CAS  Google Scholar 

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Acknowledgments

This research was financially supported by the grant from İTÜ BAP Project No. 34370 (Istanbul Technical University Scientific Research Projects Department).

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Authors and Affiliations

  1. Department of Food Engineering, Faculty of Chemical and Metallurgical Engineering, Istanbul Technical University, Maslak, 34469, Istanbul, Turkey

    Sena Bilgiç & Neşe Şahin Yeşilçubuk

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  1. Sena Bilgiç
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  2. Neşe Şahin Yeşilçubuk
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Correspondence to Neşe Şahin Yeşilçubuk.

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Bilgiç, S., Yeşilçubuk, N.Ş. Lipase-Catalyzed Acidolysis of Olive Oil with Echium Oil Stearidonic Acid: Optimization by Response Surface Methodology. J Am Oil Chem Soc 89, 1971–1980 (2012). https://doi.org/10.1007/s11746-012-2097-8

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  • DOI: https://doi.org/10.1007/s11746-012-2097-8

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