Lipase-catalyzed glycerolysis of anchovy oil in a solvent-free system: Simultaneous optimization of monoacylglycerol synthesis and end-product oxidative stability

Palacios, David; Ortega, Natividad; Rubio-Rodríguez, Nuria; Busto, María D.

doi:10.1016/j.foodchem.2018.07.184

Cited by 31 publications

(15 citation statements)

References 36 publications

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“…Generally, an increase in the unsaturation of fatty acids results in decreased oxidative stability. PUFAs (for example, n ‐3 series) are usually incorporated into SLs to enhance nutrition (He et al., ; He et al., ; Palacios, Ortega, Rubio‐Rodríguez, & Busto, ; Wang, Wang, Wang, Jin, & Wang, ), but these types of fatty acids are highly liable molecules and are easily susceptible to oxidation (Shahidi & Zhong, ). In contrast, a decreased unsaturated level leads to increased oxidative stability.…”

Section: Physicochemical Properties Of Slsmentioning

confidence: 99%

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Guo

Cai

Xie

et al. 2020

Comp Rev Food Sci Food Safe

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Structured lipids (SLs) refer to a new type of functional lipids obtained by chemically, enzymatically, or genetically modifying the composition and/or distribution of fatty acids in the glycerol backbone. Due to the unique physicochemical characteristics and health benefits of SLs (for example, calorie reduction, immune function improvement, and reduction in serum triacylglycerols), there is increasing interest in the research and application of novel SLs in the food industry. The chemical structures and molecular architectures of SLs define mainly their physicochemical properties and nutritional values, which are also affected by the processing conditions. In this regard, this holistic review provides coverage of the latest developments and applications of SLs in terms of synthesis strategies, physicochemical properties, health aspects, and potential food applications. Enzymatic synthesis of SLs particularly with immobilized lipases is presented with a short introduction to the genetic engineering approach. Some physical features such as solid fat content, crystallization and melting behavior, rheology and interfacial properties, as well as oxidative stability are discussed as influenced by chemical structures and processing conditions. Health‐related considerations of SLs including their metabolic characteristics, biopolymer‐based lipid digestion modulation, and oleogelation of liquid oils are also explored. Finally, potential food applications of SLs are shortly introduced. Major challenges and future trends in the industrial production of SLs, physicochemical properties, and digestion behavior of SLs in complex food systems, as well as further exploration of SL‐based oleogels and their food application are also discussed.

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Section: Physicochemical Properties Of Slsmentioning

confidence: 99%

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Guo

Cai

Xie

et al. 2020

Comp Rev Food Sci Food Safe

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“…Regarding the glycerolysis of VO, an important point is the product quality. In this sense, certain VO compositions are sensitive to temperature, and the use of a less aggressive catalytic route is important for achieving products of higher added value (Majid and Cheirsilp, 2012; Palacios et al, 2019). The works of Palacios et al (2019) and Majid and Cheirsilp (2012) are important examples of this aspect.…”

Section: Introductionmentioning

confidence: 99%

“…In this sense, certain VO compositions are sensitive to temperature, and the use of a less aggressive catalytic route is important for achieving products of higher added value (Majid and Cheirsilp, 2012; Palacios et al, 2019). The works of Palacios et al (2019) and Majid and Cheirsilp (2012) are important examples of this aspect. In the first one, the authors proposed the enzymatic catalysis as an alternative to minimize the effects of the thermal‐oxidative degradation in the production of MAG by the glycerolysis of anchovy oil, a substrate rich in polyunsaturated fatty acids.…”

Section: Introductionmentioning

confidence: 99%

Glycerolysis of Buriti Oil (Mauritia flexuosa) by Magnesium Oxide and Immobilized Lipase Catalysts: Reaction Yield and Carotenoids Degradation

Silva

Bönmann

Kuamoto

et al. 2021

J Americ Oil Chem Soc

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Buriti (Mauritia flexuosa) is a palm tree widely distributed in South America. The oil extracted from its fruit is an added value product for its high carotenoids content. The aim of this work was to evaluate the alkaline (magnesium oxide-MgO) and enzymatic (lipase B from Candida antarctica immobilized on macroporous acrylic resin) glycerolysis of buriti oil to obtain non-ionic emulsifiers and evaluate the carotenoids degradation during this process. Alkaline glycerolysis was carried out using a 3:1 glycerol/oil molar ratio, temperatures of 170 and 210 C, and MgO contents of 0.5 and 1%wt. Enzymatic glycerolysis reactions were performed using 3%wt. of a lipase catalyst and varying the following parameters: glycerol: oil molar ratio (3:1, 6:1, and 9:1), solvent (tert-butyl alcohol) concentration (50%, 150%, and 250%, vol./substrate mass), and temperature (40, 55 and 70 C). The products were analyzed by liquid chromatography and UV-visible spectroscopy (370-520 nm). Enzymatic glycerolysis was superior in terms of conversion and selectivity to monoacylglycerols (MAG). MAG yields were close to 80% or higher for most conditions tested for enzymatic glycerolysis, while the maximum yield for alkaline glycerolysis was of 58%. UV-Vis data showed that carotenoids were severally degraded in alkaline glycerolysis, while the enzymatic product exhibited high preservation of carotenoids and color and odor similar to those of the pure buriti oil. Based on the final composition of the non-ionic emulsifiers obtained from buriti oil by enzymatic glycerolysis, they can be considered potential raw materials for cosmetic and food industries.

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“… 5 − 7 Generally speaking, 1,3-DAG can be produced through enzymatic and chemical methods from oils and fats of plants and animals sources. 8 − 11 Although the chemical way is less costly, the process should be performed at very high temperatures (220–260 °C) and result in the heat labile polyunsaturated fatty acid degradation. 12 , 13 The enzymatic way is more preferable as it has the superiorities of being environmentally friendly, having mild reaction condition, and being specific in their reaction.…”

Section: Introductionmentioning

confidence: 99%

Kinetics and Mechanism of Solvent Influence on the Lipase-Catalyzed 1,3-Diolein Synthesis

et al. 2020

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1,3-Diacylglycerol preparation has roused increasing attention in recent years as the 1,3-diacylglycerol-rich oils can suppress the deposition of visceral fat and prevent the body weight increasing. Lipozyme TL IM-mediated esterification of oleic acid with monoolein was effective for 1,3-diacylglycerol production. During the esterification process, the solvent shows obvious influence on the diolein synthesis as well as the 1,3-diolein production. This work investigated the related kinetics and mechanism of the solvent effect on the esterification and Lipozyme TL IM performance. The results indicated that both the esterification rate constant and the acyl migration rate constant positively correlated with the log P of the solvent, while the site specificity of lipase has negative correlation with solvent log P . The acylation toward the 2-position of 1-monoolein was more sensitive to the solvent log P compared to the 1-position of glycerides. Molecular dynamics simulation revealed that solvents with different log P influenced the structure of Lipozyme TL IM including RMSD, hydrogen bond, and radial distribution function to a large extent, which subsequently led to the catalytic activity and selectivity variation of the lipase.

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Lipase-catalyzed glycerolysis of anchovy oil in a solvent-free system: Simultaneous optimization of monoacylglycerol synthesis and end-product oxidative stability

Cited by 31 publications

References 36 publications

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Synthesis, physicochemical properties, and health aspects of structured lipids: A review

Glycerolysis of Buriti Oil (Mauritia flexuosa) by Magnesium Oxide and Immobilized Lipase Catalysts: Reaction Yield and Carotenoids Degradation

Kinetics and Mechanism of Solvent Influence on the Lipase-Catalyzed 1,3-Diolein Synthesis

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