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Human milk lipids generally have the maximum long-chain fatty acids at the sn-2 position of the glycerol backbone. This positioning makes them more digestible than long-chain fatty acids located at the sn-1, 3 positions. These unique fatty acid distributions are not found elsewhere in nature. When lactation is insufficient, infant formula milk has been used as a substitute. However, the distribution of most fatty acids ininfant formula milk is still different from human milk. Therefore, structured lipids were produced by the redistribution of medium-chain fatty acids from commercial butterfat (CBF) and n-3 and n-6 long-chain fatty acids from skipjack tuna eyeball oil (STEO). Redistribution was carried out via transesterification facilitated by Asian seabass liver lipase (ASL-L). Under the optimum conditions including a CBF/STEO ratio (3:1), transesterification time (60 h), and ASL-L unit (250 U), the newly formed modified-STEO (M-STEO) contained 93.56% triacylglycerol (TAG), 0.31% diacylglycerol (DAG), and 0.02% monoacylglycerol (MAG). The incorporated medium-chain fatty acids accounted for 18.2% of M-STEO, whereas ASL-L could incorporate 40% of n-3 fatty acids and 25–30% palmitic acid in M-STEO. The 1H NMRA and 13CNMR results revealed that the major saturated fatty acid (palmitic acid) and unsaturated fatty acids (DHA and EPA) were distributed at the sn-2 position of the TAGs in M-STEO. Thus, M-STEO enriched with medium-chain fatty acids and n-3 fatty acids positioned at the sn-2 position of TAGs can be a potential substitute for human milk fatty acids in infant formula milk (IFM). [ABSTRACT FROM AUTHOR]

为开发高效、绿色、低成本的脂肪酶应用于结构脂质的制备，从内源性（脂肪酶的来源、基因序列、空间位阻）和外源性(底物空间结构、反应介质、固定化条件及反应pH)两方面讨论了脂肪酶位置选择性的影响因素。脂肪酶催化特异性由内源性因素和外源性因素共同决定。改变底物空间结构、反应介质、固定化条件和反应pH，常被用作提高脂肪酶催化性能的处理方式。只有充分考虑内外两方面因素的影响，才能充分提高脂肪酶的位置选择性和催化效率。该综述有望为高选择性脂肪酶的开发开辟新的研究方向，为后续结构脂质的高效合成提供启发性的研究思路。 To develop efficient, green and low-cost lipases for the preparation of structured lipid, the factors affecting lipase regioselectivity were discussed in terms of both endogenous (source of lipase, gene sequence, spatial resistance) and exogenous (substrate spatial structure, reaction medium, immobilization conditions and reaction pH). The lipases catalytic specificity were determined by the endogenous and exogenous factors, and changing the substrate spatial structure, reaction medium, immobilization conditions and reaction pH, were often used as treatment ways to improve the catalytic performance of the lipase. Only by fully considering the effects of both internal and external factors, the regioselectivity and catalytic efficiency could be improved. The summarize is expected to develop new research directions for the development of highly selective lipase and provide enlightening research ideas for the subsequent efficient synthesis of structured lipid.

The modification of triglycerides (TGs) via acidolysis with fatty acids (FAs) was investigated using three commercial lipases activated via hydration–aggregation pretreatment. Lipase powder was dispersed i n n -fatty alcohols and hydrated with a small volume of buffer solution under mechanical agitation. Subsequently, paste-like lipase aggregates were recovered from the mixture and lyophilized. Rhizopus japonicus lipase (RJL) exhibited acidolysis activity after hydration–aggregation pretreatment in free powder form without immobilization on solid supports, whereas non-activated lipase showed no detectable activity: the incorporation ratio of stearic acid in tripalmitin during acidolysis reached 33% within 24 h using activated RJL, whereas the acidolysis products were not detected using non-activated RJL. Morphological analysis demonstrated that the hydration of lipase powder and formation of a large oil–water interface area are essential for obtaining highly activated lipases. Decrease in chain length and increase in the degree of TG substrate unsaturation tended to increase the acidolysis activity of activated RJL, whereas the effect of chain length and degree of FA substrate unsaturation showed different trends. Chromobacterium viscosum lipase and RJL were activated via hydration–aggregation pretreatment, whereas Candida rugosa lipase was not. [Display omitted] • Lipases hydrated in fatty alcohols form aggregates containing an oil-water interface. • Hydrated, aggregated lipases show high catalytic activity after lyophilization. • Modification of triglycerides is achieved via acidolysis using activated lipases. • The oil-water interface and enzyme hydration are essential for lipase activation. • Combination of triglycerides and fatty acid substrates influences lipase activity. [ABSTRACT FROM AUTHOR]

Acylglycerols in natural oils includes monoacylglycerols (MAG), diacylglycerols (DAG) and triacylglycerols (TAG). Each acylglycerol possesses different isomers, which results in variation in physicochemical and nutritional properties that can be used in various applications. Acyl migration is a spontaneous reaction involving the transition of acylglycerols into more stable isomers. Inhibition of acyl migration is beneficial for the application of different acylglycerol isomers. Whilst, the promotion of acyl migration positively impacts the synthesis of acylglycerols, altering the properties and improving the stability of the lipid system. Few studies have been performed recently on the synthesis of various acylglycerol isomers and the approach to control the acyl migration of acylglycerols. This paper discusses the preparation of acylglycerols isomers, the factors influencing acyl migration and the application of the isomers of acylglycerols, which is important for expanding the use of different isomeric acylglycerols as functional foods.

Human milk lipids generally have the maximum long-chain fatty acids at the sn-2 position of the glycerol backbone. This positioning makes them more digestible than long-chain fatty acids located at the sn-1, 3 positions. These unique fatty acid distributions are not found elsewhere in nature. When lactation is insufficient, infant formula milk has been used as a substitute. However, the distribution of most fatty acids ininfant formula milk is still different from human milk. Therefore, structured lipids were produced by the redistribution of medium-chain fatty acids from commercial butterfat (CBF) and n-3 and n-6 long-chain fatty acids from skipjack tuna eyeball oil (STEO). Redistribution was carried out via transesterification facilitated by Asian seabass liver lipase (ASL-L). Under the optimum conditions including a CBF/STEO ratio (3:1), transesterification time (60 h), and ASL-L unit (250 U), the newly formed modified-STEO (M-STEO) contained 93.56% triacylglycerol (TAG), 0.31% diacylglycerol (DAG), and 0.02% monoacylglycerol (MAG). The incorporated medium-chain fatty acids accounted for 18.2% of M-STEO, whereas ASL-L could incorporate 40% of n-3 fatty acids and 25–30% palmitic acid in M-STEO. The 1H NMRA and 13CNMR results revealed that the major saturated fatty acid (palmitic acid) and unsaturated fatty acids (DHA and EPA) were distributed at the sn-2 position of the TAGs in M-STEO. Thus, M-STEO enriched with medium-chain fatty acids and n-3 fatty acids positioned at the sn-2 position of TAGs can be a potential substitute for human milk fatty acids in infant formula milk (IFM).

In this research, attempts were made to use rice bran lipase (RBL) from bran to optimize the fatty acid profile of existing commercial sunflower oil by either replacing or incorporating n-3 fatty acids from marine source that can be a value addition to the superior usability of rice bran. Preliminary assay of crude lipase with the substrate 4-nitrophenyl palmitate (4-NPP) showed specific activity of 0.04 U/mg. Subsequently a 9.45-fold purification (specific activity of 0.37 U/mg) was achieved through ammonium sulfate precipitation followed by fast protein liquid chromatography (FPLC) and reverse-phase high performance liquid chromatography (RP-HPLC) method of purifications. The SDS-PAGE and in-gel overlay staining of purified RBL with 4-methylumbelliferyl (4-MU) butyrate showed a single band of 33 kDa. Purified RBL showed a specificity for natural oils having long chain unsaturated fatty acids with a maximum specific activity (0.452 U/mg) in case of rice bran oil. Immobilized RBL was used to blend fish oil free fatty acids (FFA) with sunflower oil (SO) at varying ratios (v/v). Clinically desirable novel structured lipid (SL) were obtained with n-6:n-3 ratios (v/v) of 5.6:1 and 3.6:1 Thus, the current study offers better nutritional desirability to the existing nutrition profile of commercial sunflower oil and further can be exploited to modify other triglycerides to optimize the n-6:n-3 ratio. [ABSTRACT FROM AUTHOR]

This study evaluated the physio-chemical properties of a structural lipid (SL) obtained by the enzymatical incorporation of flaxseed oil into mutton tallow (MT). By measuring the melting point, colour, safety, fatty acids, apparent viscosity, shear stress and volatile compounds of the samples, the results showed that compared to MT, SL exhibited lower L∗(lightness) value, melting point, apparent viscosity and shear stress (p < 0.05). Noteworthy, the Saturated fatty acids (SFA)content of MT was reduced from 61.46% to 25.49% (p < 0.05), although SL was found to be more prone to oxidation during storage. The clearest discrepancy in volatile compounds was the increase of heterocyclic compounds in SL. In summary, improving the edible properties of animal fats by adding vegetable oils is an effective solution, and SL may have a great potential to be developed into a high-quality product with improved nutritional composition of animal fat.

BACKGROUND Chemical interesterification (CIE) is one of the important technological processes for the production of zero‐trans fats. The aim of this study was to produce trans‐free cocoa butter alternatives (CBAs) from palm kernel stearin (PKS), coconut oil (CNO) and fully‐hydrogenated palm stearin (FHPS) blends via CIE using sodium methoxide as a catalyst. The physicochemical properties, crystallization and melting behavior, solid fat content (SFC), crystal morphology and polymorphism of the structured lipids (SLs) obtained and the corresponding physical blends (PBs) were characterized and compared with commercial CBAs. RESULTS: After CIE, randomization of fatty acid distribution within and among triacylglycerol (TAG) molecules of PKS, CNO and FHPS resulted in a modification in TAG compositions of the PKS/CNO/FHPS blends and improved the properties and crystallization behavior of the blends. SFC and slip melting points of all SLs decreased from those of their respective PBs. In particular, SLs obtained from CIE of blends with 60–70% wt. PKS (blend ratios 60:10:30 and 70:10:20) exhibited the melting characteristic, SFC curves, crystal morphology and polymorphic form most similar to the commercial CBAs. In addition, these blends melted almost completely at body temperature, an improvement from that of the commercial CBAs. CONCLUSION: SLs obtained from CIE of blends with 60–70% wt. PKS has high potential to be used commercially as trans‐free CBAs for the confectionery industry. © 2021 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

The normal development and maintenance of central neural functions are highly correlated with the amount of docosahexaenoic acid (DHA; ω-3 fatty acid) accumulated in the brain. DHA incorporated at the sn-2 position of lipids is well absorbed by intestinal mucosa and utilized efficiently in vivo. However, modern consumers have a reduced direct intake of DHA and increased intake of saturated fats or ω-6 fatty acid oils, resulting in behavioral and neurophysiological deficits. To provide an understanding of the integrated beneficial effects of DHA on the human brain, this review introduces the positional difference (sn-2 and sn-1,3 positions) of DHA on a glycerol skeleton in natural fats and oils, and further discusses the possible functional mechanism regarding DHA supplementation and the gut–brain axis. The multiple bidirectional routes in this axis offer a novel insight into the interaction between DHA supplementation, the gut microbiota, and brain health. To achieve high sn-2 DHA in diets, it is suggested that sn-2 DHA lipids be enzymatically produced in more efficient and economical ways by improving the specific activities of lipases and optimizing the purification procedures. These types of diets will benefit individuals with strong needs for sn-2 ω-3 lipids such as infants, children, and pregnant and lactating women.

Medium- and long-chain triacylglycerol (MLCT) is a structured lipid with both medium- and long-chain fatty acids in one triacylglycerol molecule. Compared with long-chain triacylglycerol (LCT), which is mainly present in common edible oils, and the physical blend of medium-chain triacylglycerol with LCT (MCT/LCT), MLCT has different physicochemical properties, metabolic characteristics, and nutritional values. In this article, the recent advances in the use of MLCT in food formulations are reviewed. The natural sources and preparation of MLCT are discussed. A comprehensive summary of MLCT digestion, absorption, transport, and oxidation is provided as well as its health benefits, including reducing the risk of overweight, hypolipidemic and hypoglycemic effects, etc. The potential MLCT uses in food formulations, such as infant formulas, healthy foods for weight loss, and sports foods, are summarized. Finally, the current safety assessment and regulatory status of MLCT in food formulations are reviewed.

Structured lipids (SL) were produced from enzymatic interesterification (EIE) of palm kernel stearin (PKS), coconut oil (CNO), and fully hydrogenated palm stearin (FHPS) blends in various mass ratios. The EIE reactions were performed at 60 °C for 6 hours using immobilized Lipozyme RM IM with a mixing speed of 300 rpm. The physicochemical properties, crystallization and melting behavior, solid fat content (SFC), crystal morphology and polymorphism of the physical blends (PB), and the SL were characterized and compared with commercial cocoa butter and cocoa butter alternatives (CBA). EIE significantly modified the triacylglycerol compositions of the fat blends, resulting in changes in the physical properties and the crystallization and melting behavior. SFC and slip melting point of all SL decreased from those of their counterpart PB. In particular, SL obtained from EIE of blends 60:10:30 and 70:10:20 (PKS:CNO:FHPS) exhibited a high potential to be used as trans‐free CBA as they showed similar melting ranges, melting peak temperatures, and SFC curves to the commercial CBA with fine needle‐like crystals and desirable β' polymorph. [ABSTRACT FROM AUTHOR]

Enzymatic interesterification has the advantage of promoting great control over the positional distribution of fatty acids in the final product. However, the difficulties associated with process control and scaling-up have reduced its industrial use as a catalyst for lipid modification. Thus, the objective of this work was to scale-up production and to evaluate the physic-chemical properties of a structured lipid (SL) based on soybean, olive and fully hydrogenated crambe oils obtained by an enzymatic interesterification process. Enzyme conditioning promoted low concentration of free fatty acids in the SL and the rearrangement of trisaturated triacylglycerols was completed after a reaction time of 4h. The scaling-up did not reproduce exactly the same physicochemical modifications previously observed in SL obtained in a benchscale, but the process of obtaining the SL was controlled and showed low variation of the acidity indexes, triacylglycerol composition, regiospecificity and crystallization profile, and the levels of tocopherols, chlorophyll and oxidative stability did not altered. Thus, it was possible to upscale the SL production by 50 times, with modifications in its physico-chemical properties due to differences in lipase activity. [ABSTRACT FROM AUTHOR]

• We encapsulated structured lipids by complex coacervation of gelatin and gum arabic. • We developed a functional kefir product fortified with encapsulated structured lipids. • Oxidative stability and in vitro controlled release studies were conducted. The aim of the present study is to encapsulate structured lipids (SLs) by complex coacervation of gelatin and gum arabic with or without using transglutaminase enzymes and to develop a functional kefir product via the addition of encapsulated SLs in the form of suspension and freeze-dried coacervates. Encapsulated SLs were evaluated for their oxidative stability during 30 days of cold storage. The data showed that coacervate solutions were more sensitive to lipid oxidation compared to freeze-dried capsules. Traditionally produced kefir samples that were fortified with complex coacervation products were stored for 10 days at 4 °C. The pH values of the samples decreased, whereas titratable acidity consistently increased during the storage period. Moreover, an in vitro controlled release study was conducted with a fortified kefir sample containing freeze-dried capsules. According to the results, kefir had no significant matrix effect on oil release from the freeze-dried capsules (p > 0.05). [ABSTRACT FROM AUTHOR]

Menhaden oil was enzymatically modified with caprylic (8:0) and/or stearic acid (18:0) to produce structured lipids (SL). The goal was to produce SL with high amounts of polyunsaturated fatty acids (PUFA), a low level of saturation, and a melting point of 25–35 °C. Substrate (menhaden oil to acyl donor) molar ratios were 1:1, 1:3, and 1:5 for 8:0, and 1:1, 1:2, and 1:3 for 18:0. Enzyme load was 10% of the total weight of substrates. Time course study determined optimal time for maximum acyl donor incorporation. Linear interpolation estimated molar ratios that yielded SL with 20 or 30 mol% incorporation of 8:0 or 18:0. Enzymatic reactions were also conducted with molar ratios of menhaden oil to acyl donors:8:0:18:0 (1:1:3, 1:2:2, and 1:3:1). Lipases from Candida antarctica, Lipozyme® 435, and Rhizomucor miehei, Lipozyme® RM IM (Novozymes North America, Inc., Franklinton, NC, USA), were compared for all reactions. Total and sn‐2 fatty acid compositions, triacylglycerol (TAG) molecular species, thermal behavior, volatile lipid oxidation products, solid fat contents, and oxidative stability were compared. When 8:0 was the acyl donor, the 1:3.03 and 1:4.58 ratios resulted in incorporation of 20 and 30 mol% 8:0, respectively. With 18:0 as the acyl donor, the 1:1.32 and 1:2.41 ratios led to incorporation of 20 and 30 mol% 18:0, respectively. The 1:3:1 ratio SL had a crystallization onset (C0) of 15.3 °C and a melting completion (Mc) of 33.1 °C. The physicochemical properties of these SL suggest that some may be useful in formulating food products such as margarines and spreads. [ABSTRACT FROM AUTHOR]

The objective of this research was to evaluate enzymatic glycerolysis-interesterification to synthesize structured lipids (SLs) containing high monoacylglycerol (MAG) and diacylglycerol (DAG) from a palm stearin-olein blend (PS-PO blend). The results showed that the optimum conditions for the solvent to fat ratio, glycerol to fat ratio, and enzyme concentration were 2:1 (v/w), 1.5:1, and 15% (w/w), respectively. The conversion rate of MAG and DAG decreased at a high glycerol to fat ratio, low solvent to fat ratio, and high enzyme concentration due to an increase in viscosity and low agitation effectiveness. The emulsion capacity and stability of the SLs were 60.19% and 96.80%, respectively. The hardness of the SLs increased about 3.1-fold. The MAG, DAG, and triacylglycerol conversion rates were 0.45, 0.48, and 1.02%/h, respectively. Thus, glycerolysis-interesterification of a PS-PO blend increased DAG and MAG concentrations and further improved the hardness, emulsion capacity, and emulsion stability of the SLs. [ABSTRACT FROM AUTHOR]

Abstract Novel structured lipids (SLs) enriched with medium-and long-chain triacylglycerols (MLCTs) were synthesized to combine the benefits of both arachidonic acid and medium-chain fatty acids; however, they are susceptible to oxidative degradation. In this work, the influences of the partial replacement of whey protein isolate (WPI) as the primary wall material by prebiotic carbohydrates, such as maltodextrin (MD) and inulin (IN) as the secondary wall materials on the physicochemical characteristics and oxidative stability of the spray-dried MLCTs-rich SLs microcapsules were investigated. The highest values of viscosity and zeta-potential were achieved by the WPI/IN (1:1) emulsions. Size distributions of all the emulsions were mono modal and became bimodal after microencapsulation process. The microcapsules prepared with WPI/IN (1:1) had the lowest lightness and the highest yellowness values. The partial replacement treatments increased the solubility and reduced the moisture content of the produced microcapsules. The partial replacement of WPI by IN significantly enhanced the encapsulation efficiency (89.10 ± 1.03%), wettability properties (205 ± 10.61 S), and decreased the incidence of surface oil on the microcapsules. The free oil content was noted as 5.73 ± 0.05, 3.83 ± 0.01, and 2.40 ± 0.03% for the microcapsules produced using WPI, WPI/MD (1:1), and WPI/IN (1:1), respectively. Larger microcapsules and fairer flowing properties were achieved in the powders produced with only WPI. The partial replacement of WPI by IN provided the best oxidative stability of the microencapsulated MLCTs-rich SLs. The results revealed that MD and IN with WPI together, particularly IN proved to be a good substitute secondary wall material for spray-dried MLCTs-rich SLs, therefore suggesting its usefulness in functional food applications. Graphical abstract Unlabelled Image Highlights • Microcapsules containing MLCTs-rich SLs were prepared by using whey protein isolate without and with maltodextrin or inulin. • Microencapsulation efficiency (89.10 ± 1.03%), with 25% oil load was achieved by WPI/IN. • WPI/IN microcapsules exhibited the best oxidative stability of microencapsulated MLCTs-rich SLs. [ABSTRACT FROM AUTHOR]

The aim of this study is to develop a clean and environmentally friendly process for production of low‐calorie structured lipids in accordance with the requirement of cleaner production and sustainable developments. To achieve this, polymeric acidic ionic liquid (IL)‐functionalized SBA‐15 catalysts were prepared by surface grafting copolymerization of IL 1‐propylsulfonate‐3‐vinylimidazolium hydrogen sulfate onto the SBA‐15 support using azobisisobutyronitrile (AIBN) as an initiator. The as‐prepared solid catalysts were fully characterized using several techniques. Results demonstrated that the polymeric acidic IL was successfully tethered on the SBA‐15 silica, and the mesoporous structure of the SBA‐15 support remained intact after the grafting copolymerization. The solid catalyst showed high activities in the soybean oil acidolysis with capric and caprylic acids. The acidolysis products were analyzed by a gas chromatographic method, and the incorporation of medium‐chain fatty acids into soybean triacylglycerols was 53.4% over this solid catalyst. Furthermore, the solid catalyst could be recycled several times without appreciable loss of its activity. [ABSTRACT FROM AUTHOR]

Partial hydrolysis of emu oil was performed using Thermomyces lanuginosus lipase to remove some shorter chain fatty acids. Then eicosapentaenoic acid (EPA) was incorporated into the modified emu oil using either Lipozyme RMIM or Lipozyme TLIM to produce new EPA enriched structured lipids. Using Isooctane as a reaction solvent increased the level of EPA incorporation, which was higher with RMIM than with TLIM. TLIM incorporated EPA almost exclusively into the sn-1,3 positions, whereas RMIM incorporated EPA at sn-1,3 and sn-2 positions in an almost statistical ratio. Both structured lipids were less oxidatively stable than emu oil.

Structured lipids (SLs) are novel triacylglycerols obtained by changing the native fatty acid (FA) profiles or by the incorporation of a new desired FA in the acylglycerol backbone. These modified fats present important medical and functional properties for food applications. This work aimed to synthetize a MLM-type SL, which consists of triacylglycerols containing a medium-chain FA (M) at sn-1,3 positions and a long-chain FA (L) at sn-2 position, by acidolysis of pumpkin seed oil with capric acid, catalyzed by a commercial lipase preparation from Thermomyces lanuginosa (Lipozyme TL IM). Reactions were performed at 45 °C, in solvent-free media, at 1:2 molar ratio (pumpkin seed oil:capric acid) and a fixed amount of immobilized lipase of 5%, 10%, 15% or 20%. Incorporations of C10:0 increased with time up to 31 h (29.9 ± 0.7 mol-%) when 5% lipase load was used. Significant differences were only observed between the results obtained with 5 and 20% of biocatalyst load. The subsequent experiment was carried out with 5% lipase load, at 45 °C, 1:2 molar ratio and in the presence of n-hexane. The results showed slightly higher incorporation yields in the presence of solvent, namely at 48 h-reaction (34.7 ± 1.0 mol-%). However, since the structured lipids are to be used in food products, together with environmental and economic concerns, solvent-free systems are preferred. In this study, the synthesis of a MLM-type SL from pumpkin seed oil for food uses was well succeeded.

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The purpose of this work is to develop robust and stable catalysts for production of low-calorie lipids in a heterogeneous manner to meet the demand of green food engineering. To accomplish this, magnetic Fe 3 O 4 @SiO 2 support was prepared, and then dual acidic ionic liquid, 1-(propyl-3-sulfonate)imidazolium hydrogen sulfate, was bound onto the magnetic support via covalent attachments to prepare solid acid catalysts. The so-prepared solid catalyst was characterized by Brönsted acidity determination, elemental analysis, XRD, FT-IR, TEM, VSM, and N 2 adsorption-desorption techniques. Results showed that the ionic liquid was successfully immobilized on the Fe 3 O 4 @SiO 2 support, and the structure of magnetic support remained unchangeable after the functionalization. This solid catalyst displayed a strong magnetic responsiveness, allowing it to be easily separated by an external magnet. By using this magnetic catalyst, soybean oil was acidolyzed with caprylic and capric acids to produce medium-chain structured lipids. The medium-chain fatty acids incorporated into triacylglycerols were determined by GC techniques, and the total incorporations of caprylic and capric acids were found to be 42.5% over the catalyst. Moreover, the solid catalyst could be reused efficiently for several cycles without appreciable loss of its activity. [ABSTRACT FROM AUTHOR]

Abstract: This study aims to synthesize a cocoa butter equivalent (CBE)‐structured lipid from a blend of illipe butter (IB) and palm midfraction (PMF) by means of enzymatic interesterification using Rhizomucor miehei sn‐1,3 specific lipase, Lipozyme® RM IM (Novozymes North America, Inc., Franklinton, NC, USA) as the biocatalyst. Physical and chemical attributes of the CBE and cocoa butter (CB) were analyzed. The synthesized CBE matched the triacylglycerol (TAG) profile range of a commercial CB and is therefore hypothesized to show similar physical and chemical characteristics to CB. The TAG profile, fatty‐acid constituents, melting and cooling behavior, polymorphism, and crystal morphology were determined using high‐performance liquid chromatography, gas chromatography, differential scanning calorimetry, X‐ray diffraction (XRD), and polarized light microscopy, respectively. Four enzymatically interesterified blends of IB:PMF at different weight ratios were analyzed for their TAG profiles, and a ratio of IB:PMF 10:3 (%, w/w) at 5% enzyme load and a reaction time of 30 min gave similar TAG results to CB. The TAG values of the IB:PMF 10:3 interesterified product (IP) were 1,3‐dipalmitoyl‐2‐oleoylglycerol at 19.1 ± 1.0%, 1‐palmitoyl‐2‐oleoyl‐3‐stearoylglycerol at 42.7 ± 1.0%, and 1,3‐distearoyl‐2‐oleoylglycerol at 29.9 ± 0.3%. The melting and the cooling profile of IP and CB showed no significant difference. XRD of IP and CB displayed similar dominant peaks at 4.6 Å, representing a β polymorph. Both CB and IP have similar granular spherulitic crystals. [ABSTRACT FROM AUTHOR]

The aim of this study was to synthesize structured lipid from hazelnut oil with conjugated linoleic acid (CLA) by lipase-catalyzed esterification reaction. The incorporation of CLA into hazelnut oil was optimized by response surface methodology (RSM). Substrate molar ratio, time, and temperature were independent variables chosen for optimization of the reaction. Substrate molar ratio was the most significant variable on the incorporation of conjugated linoleic acid. Good quadratic model was achieved by multiple regression analysis and backward elimination. Optimal incorporation conditions were determined as follows: reaction temperature, 59 °C; time, 6 hours; substrate molar ratio, 4. Under these optimum conditions, a maximum incorporation ratio of CLA into hazelnut oil of 49.42% was achieved. [ABSTRACT FROM AUTHOR]

Medium-and-Long Chain Triacylglycerol (MLCT) is a type of structured lipid that is made up of medium chain, MCFA (C8-C12) and long chain, LCFA (C16-C22) fatty acid. Studies claimed that consumption of MLCT has the potential in reducing visceral fat accumulation as compared to long chain triacylglycerol, LCT. This is mainly attributed to the rapid metabolism of MCFA as compared to LCFA. Our study was designed to compare the anti-obesity effects of a enzymatically interesterified MLCT (E-MLCT) with physical blend of palm kernel and palm oil (B-PKOPO) having similar fatty acid composition and a commercial MLCT (C-MLCT) made of rapeseed/soybean oil on Diet Induced Obesity (DIO) C57BL/6 J mice for a period of four months in low fat, LF (7%) and high fat, HF (30%) diet. The main aim was to determine if the anti-obesity effect of MLCT was contributed solely by its triacylglycerol structure alone or its fatty acid composition or both. Out of the three types of MLCT, mice fed with Low Fat, LF (7%) E-MLCT had significantly ( P < 0.05) lower body weight gain (by ~ 30%), body fat accumulation (by ~ 37%) and hormone leptin level as compared to both the LF B-PKOPO and LF C-MLCT. Histological examination further revealed that dietary intake of E-MLCT inhibited hepatic lipid accumulation. Besides, analysis of serum profile also demonstrated that consumption of E-MLCT was better in regulating blood glucose compared to B-PKOPO and C-MLCT. Nevertheless, both B-PKO-PO and E-MLCT which contained higher level of myristic acid was found to be hypercholesterolemic compared to C-MLCT. In summary, our finding showed that triacylglycerol structure, fatty acid composition and fat dosage play a pivotal role in regulating visceral fat accumulation. Consumption of E-MLCT in low fat diet led to a significantly lesser body fat accumulation. It was postulated that the MLM/MLL/LMM/MML/LLM types of triacylglycerol and C8-C12 medium chain fatty acids were the main factors that contributed to the visceral fat suppressing effect of MLCT. Despite being able to reduce body fat, the so called healthful functional oil E-MLCT when taken in high amount do resulted in fat accumulation. In summary, E-MLCT when taken in moderation can be used to manage obesity issue. However, consumption of E-MLCT may lead to higher total cholesterol and LDL level. [ABSTRACT FROM AUTHOR]

[Display omitted] • Synthesis methods of different isomeric acylglycerides with high purity are summarized. • Two paths of acyl migration of different isomeric acylglycerides were summarized. • The influencing factors of acylglyceryls acyl group migration rate were summarized. • The differences in the applicable fields of different isomeric triglycerides are summarized. Acylglycerols in natural oils includes monoacylglycerols (MAG), diacylglycerols (DAG) and triacylglycerols (TAG). Each acylglycerol possesses different isomers, which results in variation in physicochemical and nutritional properties that can be used in various applications. Acyl migration is a spontaneous reaction involving the transition of acylglycerols into more stable isomers. Inhibition of acyl migration is beneficial for the application of different acylglycerol isomers. Whilst, the promotion of acyl migration positively impacts the synthesis of acylglycerols, altering the properties and improving the stability of the lipid system. Few studies have been performed recently on the synthesis of various acylglycerol isomers and the approach to control the acyl migration of acylglycerols. This paper discusses the preparation of acylglycerols isomers, the factors influencing acyl migration and the application of the isomers of acylglycerols, which is important for expanding the use of different isomeric acylglycerols as functional foods. [ABSTRACT FROM AUTHOR]

A structured lipid (SL) constituting omega fatty acids was synthesized by using linseed and grape seed oils as substrates via a lipase-catalyzed reaction. Lipozyme® TL IM was used as a biocatalyst. Good quadratic models predicting the incorporation of omega fatty acids were achieved via the Response surface methodology (RSM). The optimal conditions for targeted omega-6/omega-3 fatty acid ratio (2:1) were obtained at a substrate molar ratio 1.4, time 8.4 h, and enzyme amount 6.4%. The SL contained linoleic acid (43 g 100g-1), which was mainly located in the sn-2 position (40 g 100g-1). ?-Linoleic acid, and α-linolenic acid at the sn-2 position were 22 g 100g-1, and 11 g 100g-1, respectively. The oxidative stability of the SL, and SL with antioxidants was also investigated. The produced SL may be proposed as a source of a balanced intake of omega fatty acids and an ingredient in functional food formulations.

The Keggin-type CsHPWO was encapsulated in metal-organic framework UiO-66 by a simple solvothermal synthesis method. The characterization results showed that the morphology and crystal structure of UiO-66 were preserved, and the heteropolyanion structure remained unchanged after CsHPWO encapsulation. The prepared CsHPWO@UiO-66 material has demonstrated to be an environmentally benign catalyst in the acidolysis of soybean oil with medium-chain fatty acids for the production of low-calorie structured lipids. The FT-IR CO adsorption experiments revealed that additional Lewis acid sites were formed in the solid acid catalyst, which were essential to catalyze the acidolysis reaction. The solid catalyst could be reused for several recycles without obvious deactivation due to hardly leaching of active components into the reaction mixture. Graphical Abstract: [ABSTRACT FROM AUTHOR]

In this study, Candida lipolytica lipase ( CLL ) was immobilized on magnetic multi-walled carbon nanotubes (mMWCNTs) via hydrophobic and cation-exchange interaction. The resultant immobilized CLL showed much better thermal stability, biocatalyst activity and easier recycling than the free form. A method for efficient enzymatic acidolysis of tripalmitin (PPP) with oleic acid (OA), to produce OPO-rich TAGs, was developed, using the immobilized CLL as the biocatalyst. Under optimized conditions (2% water, 20 mg/ml enzyme, 1:6 PPP/OA, 50 °C, 2 h), the content of OPO in the final product reached 46.5%. CLL @mMWCNTs had a better activity and manipulative stability than commercial lipases. More importantly, the feasibility of CLL @mMWCNTs was also validated in the practical production of OPO-rich TAGs, using lard and restructured palm oil as the raw material. These results suggest that CLL @mMWCNTs is a promising biocatalyst for the OPO-rich TAGs production and will be helpful for the infant formula industry. [ABSTRACT FROM AUTHOR]

A structured lipid (SL) constituting omega fatty acids was synthesized by using linseed and grape seed oils as substrates via a lipase-catalyzed reaction. Lipozyme® TL IM was used as a biocatalyst. Good quadratic models predicting the incorporation of omega fatty acids were achieved via the Response surface methodology (RSM). The optimal conditions for targeted omega-6/omega-3 fatty acid ratio (2:1) were obtained at a substrate molar ratio 1.4, time 8.4 h, and enzyme amount 6.4%. The SL contained linoleic acid (43 g 100g-1), which was mainly located in the sn-2 position (40 g 100g-1). α-Linoleic acid, and α-linolenic acid at the sn-2 position were 22 g 100g-1, and 11 g 100g-1, respectively. The oxidative stability of the SL, and SL with antioxidants was also investigated. The produced SL may be proposed as a source of a balanced intake of omega fatty acids and an ingredient in functional food formulations. [ABSTRACT FROM AUTHOR]

A glucose-cysteine Maillard reaction product (MRP) was produced and its antioxidant effects on lipid oxidation were determined for a structured-lipid enriched with polyunsaturated fatty acids in a complex emulsion. Trolox equivalent antioxidant capacities (TEAC) were determined for MRP heating intervals of 2, 4, and 6 h and were compared to α-tocopherol (TOC), MRP with TOC (TOC-MRP), and TOC with ascorbyl palmitate (TOC-AP). Emulsions were produced with total antioxidant additions of 0.02% of the oil, and lipid oxidation was monitored by peroxide and p-anisidine values over 56 d. Positive correlations between browning and heating time as well as TEAC were observed. Total TEAC values for the MRP at 6 h, TOC, TOC with the MRP at 6 h, and TOC-AP were 2.51, 3.87, 2.68, and 2.76 mg trolox eq/g, respectively. Oxidation results indicated a possible antioxidant effect for the MRP at 6 h on secondary oxidation for days 14 to 28. These results suggest that the MRP at 6 h could be useful in inhibiting secondary oxidation in complex emulsions. [ABSTRACT FROM AUTHOR]

The acidolysis reaction of terebinth fruit oil with caprylic and palmitic acid has been investigated. The reaction was catalyzed by lipase (Lipozyme IM from Rhizomucormiehei) and carried out in recirculating packed bed reactor. The effects of reaction parameters have been analyzed using response surface methodology. Reaction time (3.5–6.5 h), enzyme load (10–20%), substrate flow rate (4–8 mL·min-1) and substrate mole ratios (Terebinth oil : Palmitic acid : Caprylic acid, 1:1.83:1.22–1:3.07:2.05) were evaluated. The optimum reaction conditions were 5.9 h reaction time, 10% enzyme load, 4 mL·min-1 substrate flow rate and 1:3.10:2.07 substrate mole ratio. The structured lipid obtained at these optimum conditions had 52.23% desired triacylglycerols and a lower caloric value than that of terebinth fruit oil. The melting characteristics and microstructure of the structured lipid were similar to those of commercial margarine fat extracts. The results showed that the structured lipid had the highest oxidative stability among the studied fats.

The aim of the present work is to investigate the effects of blending and chemical interesterification reactions on the softening and melting behavior of chicken fat, its stearin and medium chain triacylglycerols, and blends thereof in various ratios. Chemical interesterification is a promising alternative to the current processes of modifying the physical properties of fats. In the experimental design 7 samples corresponding to 7 different blend proportions were used. The results were represented in triangular diagrams. The addition of stearin influenced the softening and melting points. The mixture response surface methodology proved to be an extremely useful tool for the optimization of the fat mixtures.

The objective of this work was to develop a feasible ecofriendly process to produce medium-chain fatty acid (MCFA)-enriched structured lipids (SLs) in heterogeneous manners. For this purpose, the propyl-SO 3 H or arene-SO 3 H-modified SBA-15 materials were prepared through a surface functionalization of SBA-15 silica with propyl-SO 3 H and arene-SO 3 H groups. The organosulfonic acid-functionalized SBA-15 materials were characterized by Brönsted acidity determination, elemental analysis, XRD, C 13 MAS NMR, FT-IR, SEM, TG, TEM, and N 2 adsorption-desorption techniques. Results showed that the propyl-SO 3 H and arene-SO 3 H groups were successfully tethered on the SBA-15 support, and the ordered mesoporous structure of SBA-15 silica was well retained after the organofunctionalization. This organic-inorganic hybrid material displayed high surface acidities and high activities in the acidolysis of soybean oil with caprylic or capric acid to produce SLs containing MCFAs. The influences of processing parameters on the reaction were investigated. The two studied catalysts showed an excellent recyclability for the reaction. [ABSTRACT FROM AUTHOR]

The acidolysis reaction of terebinth fruit oil with caprylic and palmitic acid has been investigated. The reaction was catalyzed by lipase (Lipozyme IM from Rhizomucormiehei) and carried out in recirculating packed bed reactor. The effects of reaction parameters have been analyzed using response surface methodology. Reaction time (3.5-6.5 h), enzyme load (10-20%), substrate flow rate (4-8 mL·min-1) and substrate mole ratios (Terebinth oil : Palmitic acid : Caprylic acid, 1:1.83:1.22-1:3.07:2.05) were evaluated. The optimum reaction conditions were 5.9 h reaction time, 10% enzyme load, 4 mL·min-1 substrate flow rate and 1:3.10:2.07 substrate mole ratio. The structured lipid obtained at these optimum conditions had 52.23% desired triacylglycerols and a lower caloric value than that of terebinth fruit oil. The melting characteristics and microstructure of the structured lipid were similar to those of commercial margarine fat extracts. The results showed that the structured lipid had the highest oxidative stability among the studied fats. [ABSTRACT FROM AUTHOR]

Low calorie structured lipid (SL1) containing essential fatty acids and having hypocholesterolemic activity was prepared by enzymatic interesterification of sunflower oil with ethyl behenate. DSC studies indicated the similarity in melting profile of SL1 with that of commercial bakery shortenings. The present study was designed to evaluate the effect of replacing bakery fat with SL1 in the preparation of biscuits and cakes on the sensory and acceptability of these products. The organoleptic and quality characteristics of the biscuits prepared with SL1 are comparable with those of biscuits prepared with commercial bakery fat. However, such replacement during the preparation of cake requires the addition of emulsifier to have the product indistinguishable from that prepared using traditional bakery fat. The bakery product prepared with SL1 is low in calorie and free from trans fats. Thus the utility of novel fat with lower calorific value and having hypocholesterolemic activity in product preparation is demonstrated. [ABSTRACT FROM AUTHOR]

Partial hydrolysis of emu oil was performed using Thermomyces lanuginosus lipase to remove some shorter chain fatty acids. Then eicosapentaenoic acid (EPA) was incorporated into the modified emu oil using either Lipozyme RMIM or Lipozyme TLIM to produce new EPA enriched structured lipids. Using Isooctane as a reaction solvent increased the level of EPA incorporation, which was higher with RMIM than with TLIM. TLIM incorporated EPA almost exclusively into the sn -1,3 positions, whereas RMIM incorporated EPA at sn -1,3 and sn -2 positions in an almost statistical ratio. Both structured lipids were less oxidatively stable than emu oil. [ABSTRACT FROM AUTHOR]