Enzymatic interesterification of perilla seed oil and palm stearin: A sustainable approach to develop a novel zero-trans-fat margarine rich in omega-3 fatty acids.

The study focuses on developing a novel perilla seed oil (PeO)-based polyunsaturated fatty acid-rich margarine fat analogue using enzymatic interesterification. PeO is a rich source of omega-3 fatty acids, however, has limited application due to susceptibility to oxidative and thermal degradation. Moreover, low consumption of omega-3 fatty acids in modern diets serves as a major cause for increased prevalence of cardiovascular diseases. The stability of such oils can be improved by techniques like blending and interesterification. However, blending lacks uniformity, which can be overcome by interesterification. The process conditions, namely, enzyme load, temperature, substrate molar ratio, and reaction time, were systematically optimized using response surface methodology. The optimized interesterified fat was characterized for fatty acid and triacylglyceride (TAG) composition. The physicochemical and functional properties, along with oxidative stability, were also evaluated to determine its overall quality. The structured lipid with zero trans and low saturated fat was developed with 50:50 substrate molar ratio of PeO and palm stearin at 54°C within 5.4 h at 6.2% w/w concentration of TLIM enzyme. It exhibited 23.8% degree of interesterification, 435.5 g hardness, and 33°C slip melting point. The TAG profile of the resulting fat was significantly modified with increased triunsaturated TAGs like LnLnLn and LnLnL but reduced trisaturated TAGs like PPP. The interesterification process lowered tocopherol composition by 3%. The acid, peroxide, IP (Induction Period), and p-anisidine values of PeO significantly enhanced. The thermal behavior of the developed fat was also modified. The textural properties of margarine developed from optimized fat were comparable to commercial margarine, revealing the application of PeO in healthy margarine formulation.

Batch and continuous enzymatic interesterification of beef tallow: Interesterification degree, reaction relationship, and physicochemical properties.

The relationship between batch and continuous enzymatic interesterification was studied through enzymatic interesterification of beef tallow. The interesterification degree (ID) during the batch reaction was monitored based on triacylglycerol composition, sn-2 fatty acid composition, solid fat content, and melting profile and was described by an exponential model. A relationship equation featuring reaction parameters of the two reations was established to predict the ID and physicochemical characteristics in continuous interesterification. The prediction of the ID based on triacylglycerol composition was reliable, with an R2 value greater than 0.85. Interesterification produced more high-melting-point components for both reactions, but the acyl migration in the batch-stirring reactor was much greater, resulting in faster crystallization, a more delicate crystal network, and lower hardness. The relationship equation can be employed to predict the ID, but the prediction of physicochemical properties was constrained by the difference in acyl migration degree between the two reactions.

Novel Approaches for Elongation of Fish Oils into Very-Long-Chain Polyunsaturated Fatty Acids and Their Enzymatic Interesterification into Glycerolipids.

Elongation of the Very-Long-Chain Fatty Acids-4 (ELOVL4) enzyme that is expressed in neuronal tissues, sperm, and testes mediates biosynthesis of very-long-chain polyunsaturated fatty acids (VLC-PUFAs) from dietary long chain PUFAs (LC-PUFAs). The VLC-PUFAs are critical for neuronal and reproductive function. Therefore, mutations in ELOVL4 that affect VLC-PUFA biosynthesis contribute to retinal degenerative diseases including Autosomal Dominant Stargardt-like Macular Dystrophy (STGD3). Recent studies have also shown not only a depletion of retinal VLC-PUFAs with normal aging but also a more significant loss of VLC-PUFAs in donor eyes of patients with age-related macular degeneration (AMD). However, currently, there are no natural sources of VLC-PUFAs to be evaluated as dietary supplements for the attenuation of retinal degeneration in animal models of STGD3. Here, we report the development of a novel chemical approach for elongation of eicosapentaenoic (C20:5 n-3) and docosahexaenoic (C22:6 n-3) acids from fish oils by 6 carbon atoms to make a unique group of VLC-PUFAs, namely all-cis-hexacosa-11,14,17,20,23-pentaenoic acids (C26:5 n-3) and all-cis-octacosa-10,13,16,19,22,25-hexaenoic acids (C28:6 n-3). The three-step elongation approach that we report herein resulted in a good overall yield of up to 20.2%. This more sustainable approach also resulted in improved functional group compatibility and minimal impact on the geometrical integrity of the all-cis double bond system of the VLC-PUFAs. In addition, we also successfully used commercial deep-sea fish oil concentrate as an inexpensive material for the C6 elongation of fish oil LC-PUFAs into VLC-PUFAs, which resulted in the making of gram scales of VLC-PUFAs with an even higher isolation yield of 31.0%. The quality of fish oils and the content of oxidized lipids were key since both strongly affected the activity of the PEPPSI-IPr catalyst and ultimately the yield of coupling reactions. Downstream enzymatic interesterification was used for the first time to prepare structured glycerolipids enriched with VLC-PUFAs that could be evaluated in vivo to determine absorption and transport to target tissues relative to those of the free fatty acid forms. It turned out that in the synthesis of structured triacylglycerols and glycerophospholipids with VLC-PUFAs, the polarity of the immobilized lipase carrier and its humidity were essential.

Texture and volatile profiles of beef tallow substitute produced by a pilot-scale continuous enzymatic interesterification.

Edible beef tallow (BT) has been widely used in Sichuan hotpot due to its unique flavor and texture. However, BT should not be consumed in excess caused by its trans-fatty acids and cholesterol issues. In this study, a BT substitute was prepared after enzymatic interesterification in a pilot-scale packed-bed reactor using soybean oil and fully hydrogenated palm oil (4:3, w/w) as feedstock. The products were characterized against BT in terms of fatty acid/triacylglycerol compositions, solid fat content, polymorphism, and melting/crystallization behaviors to select the most promising BT substitute. The optimal flow rate was 120 mL/min. Changes in volatile compounds during stir-frying and simmering were also investigated for Sichuan hotpots made with these two oils. The volatile compounds of BT substitute were similar to that of natural BT. The findings will contribute to expanding the base oil categories of Sichuan hotpot oils.

Enzymatic Interesterification of Palm Stearin, Flaxseed Oil and Cottonseed Stearin to Produce Stable Plastic Fat with Balanced Omega-6 and Omega-3 Fatty Acids.

This study aimed to produce stable plastic fat with desired physicochemical characteristics and ω-6/ω-3 fatty acid ratio (1:1-4:1) from palm stearin (PS), flaxseed oil (FSO) and cottonseed stearin (CS) via enzymatic interesterification (EIE). For the first time, the EIE variables of the blends containing PS, FSO and CS were investigated and optimized through single-factor experiments and response surface design to achieve a high interesterification degree. The optimized enzymatic interesterification conditions were: 60°C, 6 wt% Lipase UM1, and 6 h. Lipase UM1 had a similar effect on ID values with commercial lipases. The EIE improved the compatibility of the lipid blends, with the interesterified product EIE-721 (7:2:1, PS: FSO:CS) being the best candidate base stock for shortening considering its solid fat content, desired ω-6/ω-3 fatty acid ratio, wide melting range, abundant ß' form crystal, and compact microstructure. This study provides a strategy to produce balanced ω-6/ω-3 fatty acid plastic fat through enzymatic interesterification and validates the application of Lipase UM1 in the preparation of plastic fat.

Trends in Fat Modifications Enabling Alternative Partially Hydrogenated Fat Products Proposed for Advanced Application.

The natural properties of oils and fats do not always allow for their direct use in industry (e.g., for food, cosmetics, and pharmaceuticals). Furthermore, such raw materials are often too expensive. Nowadays, the requirements for the quality and safety of fat products are increasing. For this reason, oils and fats are subjected to various modifications that make it possible to obtain a product with the desired characteristics and good quality that meets the needs of product buyers and technologists. The modification techniques of oils and fats change their physical (e.g., raise the melting point) and chemical properties (e.g., fatty acid composition). Conventional fat modification methods (hydrogenation, fractionation, and chemical interesterification) do not always meet the expectations of consumers, nutritionists, and technologists. In particular, Hydrogenation, while it allows us to obtain delicious products from the point of view of technology, is criticised for nutritional reasons. During the partial hydrogenation process, trans-isomers (TFA), dangerous for health, are formed. One of the modifications that meets current environmental requirements and trends in product safety and sustainable production is the enzymatic interesterification of fats. The unquestionable advantages of this process are the wide spectrum of possibilities for designing the product and its functional properties. After the interesterification process, the biologically active fatty acids in the fatty raw materials remain intact. However, this method is associated with high production costs. Oleogelation is a novel method of structuring liquid oils with small oil-gelling substances (even 1%). Based on the type of oleogelator, the methods of preparation can differ. Most oleogels of low molecular weight (waxes, monoglycerides, and sterols) and ethyl cellulose are prepared by dispersion in heated oil, while oleogels of high molecular weight require dehydration of the emulsion system or solvent exchange. This technique does not change the chemical composition of the oils, which allows them to keep their nutritional value. The properties of oleogels can be designed according to technological needs. Therefore, oleogelation is a future-proof solution that can reduce the consumption of TFA and saturated fatty acids while enriching the diet with unsaturated fatty acids. Oleogels can be named "fats of the future" as a new and healthy alternative for partially hydrogenated fats in foods.

Insight into the medium-long-medium structured lipids made from Camellia oil: Composition-structure relationship.

Medium-long-medium (MLM) structured lipid (SL) as a new SL is a potential functional ingredient in food and nutraceutical products, but its composition-structure-physicochemical properties relationship has not been revealed in food industry. MLM type of medium-long chain triacylglycerol (MLCT) was synthesized from Camellia oil by combi-lipase; its physicochemical properties and composition-structure relationship were investigated in this research. The higher MLCT (67.24% ± 0.09) and MLM (52.71% ± 0.53) productivities were achieved after parameter optimization. The physicochemical characterization of SLs exhibited mild thermal property, intermediate Fourier transform infrared spectroscopy absorption intensity, and better crystal morphology. Joint characterizations identified that MLM and long-medium-long type SL were rich in 1,3-dioctanoyl-2-linoleoyl glyceride (CaLCa), 1,3-dioctanoyl-2-oleoyl glyceride (CaOCa), 1,3-dilinoleoyl-2-octanoyl glyceride (LCaL), and 1,3-dilinoleoyl-2-decanoyl glyceride (LCL) components, respectively. This is ascribed to the higher proportion of caprylic and linoleic acid in 1,3-specific enzyme. The 3D structural analysis further demonstrated that the CaLCa, CaOCa, LCaL, and LCL molecules had lower steric energy to form symmetrical structure at 1,3-position. This research provides a practical method to produce MLM-type SL from edible oils and fats in food industry.

Preparation of functional oils rich in diverse medium and long-chain triacylglycerols based on a broadly applicable solvent-free enzymatic strategy.

To address the problems of long reaction times and limited range of adaptation in enzymatic synthesis medium- and long-chain triacylglycerols (MLCTs), a broadly applicable solvent-free enzymatic interesterification strategy was proposed. Candida sp. lipase (CSL) was immobilized on hydrophobic hollow mesoporous silica spheres (HHSS) to construct a biocatalyst designated as CSL@HHSS with a 15.3 % immobilization yield and a loading amount of 94.0 mg/g. The expressed activity and the specific activity were 20.14 U/g and 173.62 U/g, which were 4.6 and 5.6 times higher than that of free CSL, respectively. This biocatalyst demonstrated higher activity, wider applicability, and excellent reusability. Linseed oil, sunflower oil, perilla seed oil, algal oil, and malania oleifera oil were applied as substrates to produce MLCTs with medium-chain triacylglycerols (MCT) catalyzed by CSL@HHSS through interesterification in yields ranging from 69.6 % to 78.0 % within 20 min. Specific fatty acids, including linolenic acid, oleic acid, DHA, and nervonic acid (the first reported), were introduced into MLCT's skeleton, respectively. The structures were finely analyzed and identified by GC and UPLC-MS. The catalytic efficiency value of CSL@HHSS in catalyzing interesterification between linseed oil and MCT (70 ℃, 20 min, lipase 6 wt%) is 0.86 g/g∙min, which is the highest ever reported. This paper presents an effective and sustainable strategy for functional MLCTs production.

Structured lipids produced from palm-olein oil by interesterification: A controllable lipase-catalyzed approach in a solvent-free system.

Palm olein (POL) was modified by enzymatic interesterification with different degrees of acyl migration in a solvent-free packed bed reactor. The fatty acid and acylglycerol composition, isomer content, thermodynamic behavior, and relationship between crystal polymorphism, solid fat content (SFC), crystal microstructure, and texture before and after modification were studied. We found that the increase in sn-2 saturation interesterification was not only due to the generated tripalmitin (PPP) but also caused by acyl migration, and the SFC profiles were changed accordingly. The emergence of high melting point acylglycerols was an important factor accelerating the crystallization rate, further shortening the crystallization induction time, leading to the formation of large crystal spherulites, thereby reducing the hardness. The transformation from the ß' to the ß form occurred during post-hardening during storage. The isomer content also affected the physicochemical properties of the modified POL.

Enzymatic Interesterification of Vegetable Oil:A Review on Physicochemical and Functional Properties, and Its Health Effects.

In recent years, scientists and technologists have become increasingly interested in producing modified lipids with enhanced nutritional and functional properties. The application and functional properties of fats and oil depend on the composition and structure of triacylglycerols (TAG). As a result, lipid TAG changes can be used to synthesize tailored lipids with a broader range of applications. However, no natural edible oil is available with appropriate dietary and functional properties to meet the human recommended dietary allowances (RDA). On the other hand, the arising health concern is the transfat consumption produced during the chemical modification of vegetable oil through the partial hydrogenation process. Therefore, innovative technologies are shifting toward modifying fat and oil to improve their functionality. Enzymatic interesterification (EIE) is one of the emerging and novel technology to modify the technological traits of naturally available edible oil. It helps in modifying physicochemical, functional, oxidative, and nutritional characteristics of fats and oil due to the rearrangement of the fatty acid positions in the glycerol backbone after interesterification. Enzymatic interesterification utilizes lipase as a biocatalyst with specificity and selectivity to produce desired lipids. Alternation in the molecular structure of triacylglycerol results in changes in melting/dropping point, thermal properties, crystallization behavior, solid fat content, and oxidative stability. Because of its high acyl exchange reaction efficiency, simple reaction process, flexibility, eco-friendly, and generation of fewer by-products, (EIE) is gaining more attention as a substitute lipid modification approach. This review paper discusses the uses of EIE in developing modified fat with desirable physicochemical and nutritional properties. EIE is one of the potential techniques to modify vegetable oil's physicochemical, functional, and nutritional characteristics without producing any undesirable reaction products. EIE produces different modified lipids such as trans fat-free margarine, plastic fat, bakery, confectionery fat, therapeutic oil, infant food, cocoa butter substitute, and equivalent.

Rational Design of Lipase ROL to Increase Its Thermostability for Production of Structured Tags.

1,3-regiospecific lipases are important enzymes that are heavily utilized in the food industries to produce structured triacylglycerols (TAGs). The Rhizopus oryzae lipase (ROL) has recently gained interest because this enzyme possesses high selectivity and catalytic efficiency. However, its low thermostability limits its use towards reactions that work at lower temperature. Most importantly, the enzyme cannot be used for the production of 1,3-dioleoyl-2-palmitoylglycerol (OPO) and 1,3-stearoyl-2-oleoyl-glycerol (SOS) due to the high melting points of the substrates used for the reaction. Despite various engineering efforts used to improve the thermostability of ROL, the enzyme is unable to function at temperatures above 60 °C. Here, we describe the rational design of ROL to identify variants that can retain their activity at temperatures higher than 60 °C. After two rounds of mutagenesis and screening, we were able to identify a mutant ROL_10x that can retain most of its activity at 70 °C. We further demonstrated that this mutant is useful for the synthesis of SOS while minimal product formation was observed with ROL_WT. Our engineered enzyme provides a promising solution for the industrial synthesis of structured lipids at high temperature.

Production of Cocoa Butter Substitute via Enzymatic Interesterification of Fully Hydrogenated Palm Kernel Oil, Coconut Oil and Fully Hydrogenated Palm Stearin Blends.

This research synthesized structure lipids (SL) from blends of fully hydrogenated palm kernel oil (FHPKO), coconut oil (CNO) and fully hydrogenated palm stearin (FHPS) by enzymatic interesterification (EIE)using rProROL, an sn-1,3-specific lipase from Rhizopus oryzae, as a catalyst. Five physical blends of FHPKO:CNO:FHPS were prepared with the following wt. ratios: 40:10:50, 50:10:40, 60:10:30, 70:10:20 and 80:10:10. The EIE reactions were carried out at 60℃ for 6 h in a batch-type reactor using rProROL 10% wt. of the substrate. It was found that EIE significantly modified the triacylglycerol compositions of the fat blends resulting in changes in the crystallization and melting behavior. In particular, SL obtained from EIE of blend 70:10:20 exhibited high potential to be used as a cocoa butter substitute (CBS) because it showed similar solid fat content curve to the commercial CBS and crystallized into fine spherulites and desirable ß' polymorph.

Modification of palm-based oil blend via interesterification: Physicochemical properties, crystallization behaviors and oxidative stabilities.

Interesterification is widely employed as an effective technique to modify oils and fats. This study utilizes palm-based oil (palm olein: palm kernel oil: palm stearin, 5:3:2, w/w/w) as the raw material for the interesterification process performed in a pilot-scale packed bed reactor. Enzymatic interesterification (EIE) was catalyzed by Lipozyme TL IM (813.0 g) at 60℃ with reaction flow rate of 100 mL/min. Chemical interesterification (CIE) was catalyzed using sodium methoxide (0.3 wt%) as catalyst at 105 °C for 30 min. The results showed that the EIE fats had lower solid fat content tendency compared to that of CIE fats. The crystallization onset temperature was higher in EIE fats (23.09℃) compared to that of CIE (19.08℃). The results were consistent with the crystallization kinetics whereby the Avrami K constants of EIE fats were higher than that of CIE fats at various temperatures, indicating rapid crystallization and instant nucleation. Linear growth mechanism was dominant and the crystals formed were smaller in size as observed using polarized light microscope. The interesterified fats exhibited the presence of ß and ß'-crystals. While most of the tocopherol content was retained after EIE (386.18 ug/g), the molecular distillation process reduced the tocopherol concentration (110.01 ug/g) which consequently affected the oxidative stability. The findings in this work contribute to the fundamental understanding on the differences between CIE and EIE fats and provides data to support the preparation of modified fats via EIE that shows great potential as a controllable technique for industrialization.

Rhizomucor miehei lipase-catalysed synthesis of cocoa butter equivalent from palm mid-fraction and stearic acid: Characteristics and feasibility as cocoa butter alternative.

In this study, cocoa butter equivalents (CBEs) were prepared through enzymatic interesterification of palm mid-fraction (PMF) with stearic acid (SA). The reaction process parameters were experimented and the performance of the product was analysed. PMF and stearic acid (at a mass ratio of 1:2) were catalysed by 80 g kg-1 enzyme loading of Lipozyme RM IM fromRhizomucor mieheiat 60 °C for 120 min. The yield of the CBE product was more than 92%, and the CBE resembled cocoa butter (CB) in terms of its triacylglycerol composition. The hardness of the CBE product was higher than that of CB at different storage temperatures, but this difference was not obvious at 25 °C. The polymorphic structures and SFC curve of the CBE were similar to those of the CB. In addition, the CBE could be mixed with CB in any ratio without an obvious eutectic phenomena. Up to 40% CBE could be added to CB without significantly affecting the thermodynamic properties of CB. Thus, replacing CB with the CBE product is feasible.

Evaluation of Nanostructured Lipid Carriers Produced with Interesterified Buriti Oil.

RESEARCH BACKGROUND: Extracted from the pulp of an Amazonian fruit, buriti oil is rich in micronutrients with antioxidant properties and high biological value. The few studies available indicate that this oil could be used in a wide range of applications; however, there are no studies that work on the improvement in the characteristics of this oil for commercial application. The enzymatic interesterification is one of the tools available to improve the properties of oils and fats and our recent studies have demonstrated that the lipase could specifically act on buriti oil to produce structured lipids rich in oleic acid, while preserving most of the minor compounds present in this oil. Still looking for ways to expand the applicability of this raw oil, in this work, we are interested in studying the behaviour of this structured oil in nanostructured lipid carriers (NLCs). EXPERIMENTAL APPROACH: The NLCs were produced with interesterified buriti oil and the stability, droplet size, electrical charge, microstructure, polymorphism and antioxidant activity of the samples were evaluated by ORAC and FRAP methods. RESULTS AND CONCLUSIONS: The results showed that the interesterification formed more unsaturated triacylglycerols (TAGs), and NLCs prepared with interesterified buriti oil had smaller droplets than NLCs with crude buriti oil. Particles remained stable throughout the storage period and NLCs exhibited complex polymorphism with the presence of three crystalline forms. The oxygen radical absorbance capacity (ORAC) value was approx. 23% higher in nanolipid carries with structured lipids than in the nanolipid carriers with crude buriti oil, and the ferric reducing antioxidant power (FRAP) value 16% higher, demonstrating the influence of interesterification on the antioxidant activity of nanocarriers. Thus, NLCs prepared with interesterified buriti oil had small droplets, high stability and antioxidant capacity, and have a potential for nutritional and biological applications. NOVELTY AND SCIENTIFIC CONTRIBUTION: This research showed that interesterification positively influenced the physicochemical properties of NLCs, producing the oil rich in oleic acid, high stability and antioxidant capacity. Therefore, it may be interesting to use these nanocarriers to obtain efficient carrier systems for future applications.

Lipase catalysis of α-linolenic acid-rich medium- and long-chain triacylglycerols from perilla oil and medium-chain triacylglycerols with reduced by-products.

BACKGROUND: Medium- and long- chain triacylglycerols (MLCTs) are functional structural lipids that can provide the human body with essential fatty acids and a faster energy supply. This study aimed to prepare MLCTs rich in α-linolenic by enzymatic interesterification of perilla oil and medium-chain triacylglycerols (MCTs), catalyzed by Lipozyme RM IM, Lipozyme TL IM, Lipozyme 435, and Novozyme 435 respectively. RESULTS: The effects of lipase loading, concentration of MCTs, reaction temperature, and reaction time on the yield of MLCTs were investigated. It was found that the reaction achieved more than a 70% yield of MLCTs in triacylglycerols under the conditions of 400 g kg-1 MCTs and 60 g kg-1 lipase loading after equilibrium. A novel two-stage deodorization was also applied to purify the interesterification products. The triacylglycerols reach over 97% purity in the products with significant removal (P < 0.05) of the free fatty acids, and the trans fatty acids were strictly controlled at below 1%. There was more than 40% α-linolenic in the purified products, with long-chain fatty acids mostly occupying the desired sn-2 position in acylglycerols, which are more active in hydrolysis. CONCLUSION: A series of novel α-linolenic acid-rich medium- and long-chain triacylglycerols was prepared. Under appropriate reaction conditions, the yield of MLCTs in triacylglycerols was above 70%. A novel two-stage deodorization can be used to promote the elimination of free fatty acids and limit the generation of trans fatty acids. © 2020 Society of Chemical Industry.

Characterization of enzymatically interesterified palm oil-based fats and its potential application as cocoa butter substitute.

Cocoa butter substitutes (CBS) used for chocolate preparation was produced using a mixture of palm kernel oil (PKO) and enzymatically interesterified fats. The interesterified fats consisted of palm olein (POL), fully hydrogenated palm oil (FHPO) and PKO that were catalyzed using Lipozyme TL IM at 65 °C in a solvent-free packed bed reactor. An interesterification degree of 97.10% was obtained using feed flow rate of 70 mL/min and the interesterified fats showed steep solid fat content (SFC) curve characteristics with low SFC at high temperature. In the binary system, PKO and the interesterified fats showed good compatibility at 5-10 °C, while eutectic effects were observed at 15-35 °C. CBS produced from PKO and the interesterified fats in a mass ratio of 4:6 (CBS-46) and 3:7 (CBS-37) had crystals formed prominently in the ß' form. Without the need of a tempering process, chocolate made using CBS-46 as the base oil exhibited the desired properties in terms of hardness and fracturability.

Evaluation of cytotoxicity of nanolipid carriers with structured Buriti oil in the Caco-2 and HepG2 cell lines.

Buriti oil is rich in monounsaturated fatty acids, carotenoids and tocopherols and it is used for the treatment of various diseases. One strategy to restructure the triglycerides is enzymatic interesterification and nanocarriers have been employed to improve the solubility, bioavailability and stability of active compounds. This work aims to investigate the in vitro cytotoxicity of this structured oil in nanoemulsions and nanostructured lipid carriers to expand the applicability of the crude oil. None of the samples had a cytotoxic effect on Caco-2 and HepG2 cell lines at the concentrations tested. Structured lipids acted protecting against oxidative stress and lipid peroxidation. Additionally, no consumption of glutathione has been observed in both cells, and the compounds present in buriti oil are possibly acting as antioxidants. Thus, nanoparticles prepared with interesterified buriti oil had low cytotoxicity and high oxidative stability, with great potential for future applications.

Interesterification of rice bran wax and palm olein catalyzed by lipase: Crystallization behaviours and characterization.

Rice bran wax (RBW) is a traditional plant based natural wax and an increasingly popular component in textiles, fruit coatings and cosmetics. Properties of RBW can be modified by acyglycerols, and the resulting products can possess features with great potential in different applications. In this study, RBW was interesterified with palm olein (POL) catalyzed by Lipozyme TL IM, and the effects of RBW on the crystallization rate, solid fat content (SFC) and thermodynamic properties were investigated. The crystallization rates of RBW-based enzymatically interesterified (EIE) products were significantly higher than both the starting mixture and fully hydrogenated rapeseed oil (FHRSO). The EIE RBW-based samples were predominantly crystallized in ß' form, and presented a much smoother SFC profile as compared to physically blended raw materials. The SFC values were significantly decreased, conversely increased, and remained constant, and at 10 °C, 20-30 °C, and 35-40 °C as the wax ester and acylglycerols compositions changes. Overall, RBW-based samples after EIE showed an increased hardness and good surface properties, which make it a potential plastic fats substitute.

Synthesis of cocoa butter substitutes from Cinnamomum camphora seed oil and fully hydrogenated palm oil by enzymatic interesterification.

Cinnamomum camphora trees have a vast range of distribution in southern China and the seed oil has unique fatty acid (FA) properties and various bio-activities. In this work, Cinnamomum camphora seed oil (CCSO) was utilized to synthesize value-added cocoa butter substitute (CBS) by enzymatic interesterification. The synthesis was conducted in a solvent-free system by blending CCSO with fully hydrogenated palm oil under the catalysis of Lipozyme RM IM. The reacted products were assessed with physicochemical properties, i.e. FA composition, slip melting point (SMP), triacylglycerol (TAG), crystal polymorphism, microstructure, melting and crystallization properties and solid fat content (SFC). It showed that MCFAs (capric acid plus lauric acid) was the main fatty acid in products, accounting for over 45%. Comparing to physical blends, some novel TAG species such as LaLaLa and LaMLa/LaLaM were observed after enzymatic interesterification whereas SSS TAGs were reduced. IP presented a ball-like, well-distributed and nearly round crystal microstructure and a smaller crystal size. Moreover, it should be mentioned that SFC of IP ranging from 31.85 to 38.47% at 25 °C with most ß' crystal forms, was beneficial to improve the spreadability in term of confectionery products and baked goods. The SMP of the interesterified products was 35.75-36.15 °C which closed to the commercial CBS. Hence, the products synthesized can be used to as CBS, and the results in this study also showed CCSO have value-added applications.