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Lipase catalyzed interesterification of Amazonian patauá oil and palm stearin for preparation of specific-structured oils

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Abstract

This study showed that enzymatic interesterification of Amazonian oils could be an important tool in order to produce new oils with physicochemical properties that improve the applications of these raw materials. Structured oils of Amazonian patauá oil and palm stearin using two lipases were produced in three different enzymatic systems: first, a crude lipase from the fungus Rhizopus sp (a microorganism isolated in our laboratory); second, a commercial lipase; and third, to check any synergistic effect, a mixture of both lipases (Rhizopus sp and commercial). The lipase from Rhizopus sp was specific in the incorporation of oleic acid at the sn-1,3 positions of the triacylglycerol, resulting in an oil richer in saturated fatty acid in the sn-2 position. This enzyme, produced by solid-state fermentation, even though crude, was fatty acid and positional specific and able to operate at low concentration (2.5 %, w/w). In the second enzyme system, the commercial lipase from Thermomyces lanuginosus was not specific in the tested conditions; there was no change in the distribution of saturated and unsaturated fatty acids in the three positions of the triacylglycerol profile, there was only a replacement by the type of fatty acid at the same position. In the third enzyme system, the mixture of both lipases shows no synergic effect. The structured oils retained the concentration of bioactive α- and γ- tocopherol in the three enzyme systems. Triacylglycerol classes and Thermal behavior tests indicated the formation of more homogeneous triacylglycerols, especially the mono and di-unsaturated.

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References

  • Antoniosi Filho NR, Mendes OL, Lanças FM (1995) Computer prediction of triacylglycerol composition of vegetable oils by HRGC. Chromatographia 40:557–562

    Article  CAS  Google Scholar 

  • AOCS: Official Methods and Recommended Practices of the AOCS (2009) 6th edition. American Oil Chemists’ Society, Champaign

  • Basso RC, Almeida AJ, Batista EAC (2012) Liquid–liquid equilibrium of pseudoternary systems containing glycerol + ethanol + ethylic biodiesel from crambe oil (Crambe abyssinica) at T/K = (298.2, 318.2, 338.2) and thermodynamic modeling. Fluid Phase Equilib 333:55–62

    Article  CAS  Google Scholar 

  • Campos R (2005) Experimental methodology. In: Marangoni AJ (ed) Fat crystal networks. Marcel Dekker, New York, pp 267–349

    Google Scholar 

  • D’Agostini D, Gioielli LA (2002) Stereospecific distribution of structured lipids obtained from palm oil, palm kernel oil, and medium chain triacylglycerols. Braz J Pharm Sci 38:345–354

    Google Scholar 

  • Esteban L, Jiménez MJ, Hita E, González PA, Martín L, Robles A (2011) Production of structured triacylglycerols rich in palmitic acid at sn-2 position and oleic acid at sn - 1,3 positions as human milk fat substitutes by enzymatic acidolysis. Biochem Eng J 54:62–69

    Article  CAS  Google Scholar 

  • Farmani J, Safari M, Hamedi M (2006) Application of palm olein in the production of zero-trans Iranian vanaspati through enzymatic interesterification. Eur J Lipid Sci Technol 108:636–643

    Article  CAS  Google Scholar 

  • Fernandez-Lafuente R (2010) Lipase from Thermomyces lanuginosus: Use and prospects as an industrial biocatalyst. J Mol Catal B Enzym 62:197–212

    Article  CAS  Google Scholar 

  • Guedes AMM, Ming CC, Ribeiro APB, Silva RC, Gioielli LA, Gonçalves LAG (2014) Physicochemical properties of interesterified blends of fully hydrogenated Crambe abyssinica Oil and soybean Oil. J Am Oil Chem Soc 91:111–123

    Article  CAS  Google Scholar 

  • Hartman L, Lago RCA (1973) Rapid preparation of fatty acid methyl esters from lipids. Lab Pract 22:475–494

    CAS  Google Scholar 

  • Holm HC, Cowan D (2008) The evolution of enzymatic interesterification in the oils and fats industry. Eur J Lipid Sci Technol 110:679–691

    Article  CAS  Google Scholar 

  • Issariyakul T, Dalai AK (2014) Biodiesel from vegetable oils. Renew Sust Energ Rev 31:446–471

    Article  CAS  Google Scholar 

  • Jiang Q (2014) Natural forms of vitamin E: Metabolism, antioxidant, and anti-inflammatory activities and their role in disease prevention and therapy. Free Radical Bio Med 72:76–90

    Article  CAS  Google Scholar 

  • Jiménez MJ, Esteban L, Robles A, Hita E, González PA, Muñío MM, Molina E (2010) Production of triacylglycerols rich in palmitic acid at sn-2 postion by lipase-catalyzed acidolysis. Biochem Eng J 51:172–179

    Article  Google Scholar 

  • Lopes DB, Duarte MCT, Macedo GA (2011) Biosynthesis of oleyl oleate wax ester by non-commercial lipase. Food Sci Biotechnol 20:1203–1209

    Article  CAS  Google Scholar 

  • Lunn J (2007) Monounsaturated in the diet. Br Nutr Found 32:378–391

    Article  Google Scholar 

  • Macedo GA, Pastore GM, Rodrigues MI (2004) Optimising the synthesis of isoamyl butyrate using Rhizopus sp lipase with a central composite rotatable design. Process Biochem 39:687–692

    Article  CAS  Google Scholar 

  • Montúfar R, Laffargue A, Pintaud J-C, Hamon S, Avallone S, Dussert S (2010) Oenocarpus bataua Mart. (Arecaceae): Rediscovering a source of high oleic vegetable oil from Amazonia. J Am Oil Chem Soc 87:167–172

    Article  Google Scholar 

  • Muralidhar RV, Chirumamilla RR, Marchant R, Ramachandran VN, Ward OP, Nigam P (2002) Understanding lipase stereoselectivity. World J Microb Biot 18:81–97

    Article  CAS  Google Scholar 

  • Nunes PA, Pires-Cabral P, Ferreira-Dias S (2011) Compositional and textural properties of milk-soybean oil blends following enzymatic interesterification. Food Chem 127:993–998

    Article  CAS  Google Scholar 

  • O’Brien RD (2009) Fats and Oils: formulating and processing for applications, 3rd edn. CRC Press, New York

    Google Scholar 

  • Pacheco YM, López S, Bermúdez B, Abia R, Villar J, Muriana FJ (2008) A meal rich in oleic acid beneficially modulates postprandial sICAM-1 in and sVCAM-1 in normotensive and hypertensive hypertriglyceridemic subjects. J Nutr Biochem 19:200–205

    Article  CAS  Google Scholar 

  • Poppe JK, Matte CR, Peralba MCR, Fernandez-Lafuente R, Rodrigues RC, Ayub MAZ (2015) Optimization of ethyl ester production from olive and palm oils using mixtures of immobilized lipases. Appl Catal A Gen 490:50–56

    Article  CAS  Google Scholar 

  • Quinlan P, Moore S (1993) Modification of triacylglycerols by lipases: Process technology and its application to the production of nutritionally improved fats. Inform 4:580–585

    Google Scholar 

  • Reshma MV, Saritha SS, Balachandran C, Arumughan C (2008) Lipase catalyzed interesterification of palm stearin and rice bran oil blends for preparation of zero trans shortening with bioactive phytochemicals. Bioresource Technol 99:5011–5019

    Article  CAS  Google Scholar 

  • Ribeiro APB, Basso RC, Grimaldi R, Gioielli LA, Gonçalves LAG (2009) Instrumental methods for evaluation of interesterified fats. Food Anal Methods 2:282–302

    Article  Google Scholar 

  • Rodrigues AMC, Darnet S, Silva LHM (2010) Fatty acid profiles and tocopherol contents of buriti (Mauritia flexuosa), patawa (Oenacarpus bataua), tucuma (Astrocaryum vulgare), mari (Poraqueiba paraensis) and inaja (Maximilian maripa) fruits. J Brazil Chem Soc 21:2000–2004

    Article  CAS  Google Scholar 

  • Rodrigues RC, Ayub MAZ (2011) Effects of the combined use of Thermomyces lanuginosus and Rhizomucor miehei lipases for the transesterification and hydrolysis of soybean oil. Process Biochem 46:682–688

    Article  CAS  Google Scholar 

  • Rosset IG, Tavares MCH, Assaf EM, Porto ALM (2011) Catalytic ethanolysis of soybean oil with immobilized lipase from Candida antarctica and 1H NMR and GC quantification of the ethyl esters (biodiesel) produced. Appl Catal A Gen 392:136–142

    Article  CAS  Google Scholar 

  • Sengupta A, Ghosh M, Bhattacharyya DK (2014) In vitro antioxidant assay of medium chain fatty acid rich rice bran oil in comparison to native rice bran oil. J Food Sci Technol. doi:10.1007/s13197-014-1543-z

    Google Scholar 

  • Silva RC, Soares DF, Lourenço MB, Soares FASM, Silva KG, Gonçalves MIA, Gioielli LA (2010) Continuos enzymatic interesterification of lard and soybean oil blend: Effects of different flow rates on physiscal properties and acyl migration. LWT - Food Sci Technol 43:752–758

    Article  Google Scholar 

  • Speranza P, Macedo GA (2012) Lipase-mediated production of specific lipids with improved biological and physicochemical properties. Process Biochem 47:1699–1706

    Article  CAS  Google Scholar 

  • Speranza P, Macedo GA (2013) Biochemical characterization of highly organic solvent-tolerant cutinase from Fusarium oxysporum. Biocatal Agric Biotechnol 2:372–376

    Google Scholar 

  • Speranza P, Ribeiro APB, Cunha RL, Macedo JA, Macedo GA (2015) Influence of emulsion droplet size on antimicrobial activity of interesterified Amazonian oils. LWT - Food Sci Technol 60:207–212

    Article  CAS  Google Scholar 

  • Svensson J, Adlercreutz P (2011) Effect of acyl migration in Lipozyme TL IM-catalyzed interesterification using a triacylglycerol model system. Eur J Lipid Sci Technol 113:1258–1265

    Article  CAS  Google Scholar 

  • Vlahov G (1998) Regiospecific analysis of natural mixtures of triglycerides using quantitative 13C nuclear magnetic resonance of acyl chain carbonyl carbons. Magn Reson Chem 36:359–362

    Article  CAS  Google Scholar 

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Acknowledgments

The authors wish to thank to Dr. Luiza H. Meller da Silva and Dr. Antonio M. da Cruz Rodrigues of the University of Pará for providing the oils. The authors are also grateful to Dr. Rodrigo Corrêa Basso - DEA/FEA- Unicamp for his support during the fatty acid analyses. Financial supports were provided by National Council for the Improvement of Higher Education (Capes) and by grant # 2012-22774-5, São Paulo Research Foundation (Fapesp).

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Correspondence to Paula Speranza.

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Speranza, P., Ribeiro, A.P.B. & Macedo, G.A. Lipase catalyzed interesterification of Amazonian patauá oil and palm stearin for preparation of specific-structured oils. J Food Sci Technol 52, 8268–8275 (2015). https://doi.org/10.1007/s13197-015-1943-8

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  • DOI: https://doi.org/10.1007/s13197-015-1943-8

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