Abstract
Low-calorie structured lipids (SLs) rich in behenic and oleic acids were produced by enzymatic (EI) and chemical interesterification (CI) of high oleic sunflower oil and fully hydrogenated Crambe abyssinica oil in proportions of 60:40, 50:50, 40:60 and 30:70 (w/w), respectively. The immobilized lipase from Thermomyces lanuginosus (Lipozyme TL IM) was used for 3 h at 70 °C at a dosage of 7% (w/w) free of organic solvents. The original blend (BE) and the reaction products were evaluated for their fatty acid (FA) and triacylglycerols (TAG) compositions, solid fat contents, thermal analysis, regiospecific distribution of the FA, microstructure and polymorphism. The tendency was towards a reduction in the C52, C54, C60, C62 and C64 TAG contents and an increase in the C56, C58 e C66 TAG contents, therefore the solid fat content was reduced. There was lower acyl migration at the sn-2 position of the TAGs in EI as compared to CI in all the blends ratios. Needle-like crystals were predominant in the IE while large symmetrical spherulites were observed in the BE. Reduction in the mean crystal diameter was observed in all the blends, in addition to modifications of the crystal morphology. X-ray diffraction analysis showed a predominance of the β’ form crystals in both the IE and CI. The SLs were produced for application in the food industry as bakery/confectionery fats in the proportions of 60:40/50:50 and as additive in the crystallization of lipids in the proportions of 40:60/30:70.
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Ahmadi L, Wright AJ, Marangoni AG (2008) Chemical and enzymatic interesterification of tristearin/triolein-rich blends: microstructure and polymorphism. Eur J Lipid Sci Technol 110:1025–1034
Akoh CC (1995) Structured lipids. Enzym Approach Inf 6:1055–1061
Alberio C, Izquierdo NG, Galellac T (2016) A new sunflower high oleic mutation confers stable oil grain fatty acid composition across environments. Eur J Agron 73:25–33
AOCS (2009) Official methods and recommended practices of the AOCS, 6th edn. American Oil Chemists’ Society, Champaign
Basso RC, Ribeiro APB, Masuchi MH, Gioielli LA et al (2010) Tripalmitin and monoacylglycerols as modifiers in the crystallisation of palm oil. Food Chem 122:1185–1192
Grimaldi R, Gonçalves LAG, Ando MY (2005) Otimização da reação de interesterificação química de óleo de palma. Quím. Nova 28:633–636
Guedes AMM, Ming CC, Ribeiro APB, Silva RC et al (2014) Physicochemical properties of interesterified blends of fully hydrogenated Crambe abyssinica oil and soybean oil. J Am Oil Chem Soc 91:111–123. doi:10.1007/s11746-013-2360-7
Hartman L, Lago RCA (1973) Rapid preparation of fatty acid methyl esters from lipids. Lab Pract 22:475–494
Ifeduba EA, Martini S, Akoh CC (2016) Enzymatic interesterification of high oleic sunflower oil and tripalmitin or tristearin. J Am Oil Chem Soc 93:61–67
Kojima M, Tachibana N, Yamahira T, Seino S et al (2010) Structured triacylglycerol containing behenic and oleic acids suppresses triacylglycerol absorption and prevents obesity in rats. Lipids Health Dis 9:77
Labalette F, Jouffret P, Merrien A (2012) Oleic Sunflower production: current situation and trends for the future. In: Proceedings of 18th international sunflower conference
Laghetti G, Piergiovanni AR, Perrino P (1995) Yield and oil quality in selected lines of Crambe abyssinica grow in Italy. Ind Crop Prod 4:203–212
Lee JH, Akoh CC, Lee KT (2008) Physical properties of trans-free bakery shortening produced by lipase-catalyzed interesterification. J Am Oil Chem Soc 85:1–11
Lopes JD, Grosso CRF, Calligaris GA, Cardoso LP et al (2015) Solid lipid microparticles of hardfats produced by spray cooling as promising crystallization modifiers in lipid systems. Eur J Lipid Sci Technol 117:1733–1744
Marangoni AG, Narine SS (2002) Identifying key structural indicators of mechanical strength in networks of fat crystals. Food Res Int 35:957–969
Meng Z, Geng WX, Li JW, Yang ZQ et al (2013) Enzymatically catalyzed synthesis of anti-blooming agent 1, 3- dibehenoyl-2-oleoyl glycerol in a solvent-free system: optimization by response surface methodology. J Agric Food Chem 61:10798–10806
Mori H (1989) BOB: a fat bloom inhibitor. Manuf Conf 69:63–66
Mu H, Porsgaard T (2005) The metabolism of structured triacylglycerols. Prog Lipid Res 44:430–448
Narine SS, Marangoni AJ (1999) Relating structure of fat crystal networks to mechanical properties: a review. Food Res Int 32:227–248
Oliveira GM, Ribeiro APB, Santos AO et al (2015) Hard fats as additives in palm oil and its relationships to crystallization process and polymorphism. LWT—Food Science and Technology 63:1163–1170
Pacheco C, Crapiste GH, Carrín ME (2015) Study of acyl migration during enzymatic interesterification of liquid and fully hydrogenated soybean oil. J Mol Catal B Enzym 122:117–124
Pande G, Sabir JSM, Baeshen NA, Akoh CC (2013) Enzymatic synthesis of extra virgin olive oil based infant formula fat analogues containing ARA and DHA: one-stage and two-stage syntheses. J Agric Food Chem 61:10590–10598
Panno G, Prior M (2009) Avaliação de substratos para a germinação de crambe (Crambe abyssinica). Rev Cultiv Saber 2:151–157
Ribeiro APB, Basso RC, Santos AO, Andrade GC et al (2013a) Hardfats as crystallization modifiers of cocoa butter. Eur J Lipid Sci Technol 11:1462–1473
Ribeiro APB, Basso RC, Kieckbusch TG (2013b) Effect of the addition of hardfats on the physical properties of cocoa butter. Eur J Lipid Sci Technol 115:301–312
Sato K (2001) Crystallization behaviour of fats and lipids:a review. Chem Eng Sci 56:2255–2265
Smith KW, Bhaggan K, Talbot G, van Malssen KF (2011) Crystallization of fats: influence of minor components and additives. J Am Oil Chem Soc 88:1085–1101
Souza ADV, Fávaro SP, Ítavo IC, Roscoe R (2009) Caracterização química de sementes e tortas de pinhão-manso, nabo-forrageiro e Crambe. Pesq Agropec Bras 44:1328–1335
Speranza P, Ribeiro APB, Macedo GAM (2015) Lipase catalyzed interesterification of Amazonian patauá oil and palm stearin for preparation of specific-structured oils. J Food Sci Technol 52:8268–8275. doi:10.1007/s13197-015-1943-8
Timms RE (1984) Phase behaviour of fats and their mixtures. Prog Lipid Res 23:1–38
Tynek M, Ledóchowska E (2005) Structured triacylglycerols containing behenic acid: preparation and properties. J Food Lipids 12:77–89
Vlahov G, Giuliani AA, Del RP (2010) 13C NMR spectroscopy for determining the acylglycerol positional composition of lampante olive oils. Chemical shift assignments and their dependence on sample concentration. Anal Method 2:916–923
Zhao SQ, Hu JN, Zhu XM et al (2014) characteristics and feasibility of trans-free plastic fats through lipozyme TL IM-catalyzed interesterification of palm stearin and akebia trifoliata variety australis seed oil. J Agric Food Chem 62:3293–3300
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The authors gratefully acknowledge the financial support of CAPES, CNPq and FAPESP, and the suppliers of the raw materials.
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Ribeiro, M.D.M.M., Ming, C.C., Lopes, T.I.B. et al. Synthesis of structured lipids containing behenic acid from fully hydrogenated Crambe abyssinica oil by enzymatic interesterification. J Food Sci Technol 54, 1146–1157 (2017). https://doi.org/10.1007/s13197-017-2540-9
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DOI: https://doi.org/10.1007/s13197-017-2540-9