Structured lipids (SLs) are lipids that have been chemically or enzymatically modified from their natural biosynthetic form. Because SLs are made to possess desired nutritional, physicochemical, or textural properties for various applications in the food industry, many research activities have been aimed at their commercialization. The production of SLs by enzymatic procedures has a great potential in the future market because of the specificity of lipases and phospholipases used as the biocatalysts. The aim of this review is to provide concise information on the recent research trends on the enzymatic synthesis of SLs of commercial interest, such as medium- and long-chain triacylglycerols, human milk fat substitutes, cocoa butter equivalents, trans-free or low-trans plastic fats (such as margarines and shortenings), low-calorie fats/oils, health-beneficial fatty acid-rich fats/oils, mono- or diacylglycerols, and structurally modified phospholipids. This limited review covers 108 research articles published between 2010 and 2014 which were searched in Web of Science.
Structured lipids (SLs) for formulating trans-free margarines were synthesized by lipase-catalyzed interesterification of the blends of canola oil (CO), palm stearin (PS), and palm kernel oil (PKO) in weight ratios (CO/PS/PKO) of 40:60:0, 40:50:10, 40:40:20, 40:30:30, 50:30:20, and 60:25:15. The atherogenicity was determined using fatty acid profiles. We also determined the physical properties (melting/crystallization profiles, solid fat content, polymorphism, and microstructure) of SLs and the textural properties of margarines made with the SLs. The SLs from the 50:30:20 and 60:25:15 blends had atherogenic indices similar to or lower than those of the commercial trans (CTMF) and similar to the trans-free margarine fats (CTFMF). SLs from the blends with PKO contained a wide range of fatty acids (C6-C20) and had more beta' than beta polymorphs. Margarines made with SLs from 50:30:20 and 60:25:15 blends possessed similar hardness, adhesiveness, or cohesiveness to margarines made with CTMF and CTFMF, respectively. Therefore, CO/PS/PKO-based SLs were suitable for formulating trans-free margarines with low atherogenicity and desirable textural properties.
Lipase-catalyzed acidolysis in hexane to produce structured lipids (SLs) from sesame oil and caprylic acid was optimized by considering both total incorporation (Y1) and acyl migration (Y2). Response surface methodology was applied to model Y1 and Y2, respectively, with three reaction parameters: temperature (X1), reaction time (X2), and substrate molar ratio (X3). Well-fitting models for Y1 and Y2 were established after regression analysis with backward elimination and verified by a chi2 test. All factors investigated positively affected Y1. For Y2, X1 showed the greatest positive effect. However, there was no effect of X3. We predicted the levels of Y2 and acyl incorporation into sn-1,3 positions (Y3) based on Y1. The results showed that over the range of ca. 55 mol % of Y1, Y3 started to decrease, and Y2 increased rapidly, suggesting that Y1 should be kept below ca. 55 mol % to prevent decrease in quality and yield of targeted SLs.
Structured lipid (SL) was prepared from roasted sesame oil and caprylic acid (CA) by Rhizomucor miehei lipase-catalyzed acidolysis in a bench-scale continuous packed bed reactor. Total incorporation and acyl migration of CA in the SL were 42.5 and 3.1 mol %, respectively, and the half-life of the lipase was 19.2 days. The SL displayed different physical and chemical properties, less saturated dark brown color, lower viscosity, lower melting and crystallization temperature ranges, higher melting and crystallization enthalpies, higher smoke point, higher saponification value, and lower iodine value, in comparison to those of unmodified sesame oil. The oxidative stability of purified SL was lower than that of sesame oil. There were no differences in the contents of unsaponifiables including tocopherols and phytosterols. However, total sesame lignans content was decreased in SL due to the loss of sesamol when compared to sesame oil. Most of the 70 volatiles present in roasted sesame oil were removed from SL during short-path distillation of SL. These results indicate that the characteristics of SL are different from those of original sesame oil in several aspects except for the contents of tocopherols and phytosterols.
The aim of this study was to verify the authenticity of sesame oils using combined analysis of stable isotope ratio, (1)H NMR spectroscopy, and fatty acid profiles of the oils. Analytical data were obtained from 35 samples of authentic sesame oils and 29 samples of adulterated sesame oils currently distributed in Korea. The orthogonal projection to latent structure discriminant analysis technique was used to select variables that most effectively verify the sesame oil authenticity. The variables include δ(13)C value, integration values of NMR peaks that signify the CH3 of n-3 fatty acids, CH2 between two C═C, protons from sesamin/sesamolin, and 18:1n-9, 18:3n-3, 18:2t, and 18:3t content values. The authenticity of 65 of 70 blind samples was correctly verified by applying the range of the eight variables found in the authentic sesame oil samples, suggesting that triple analysis is a useful approach to verify sesame oil authenticity.
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