Production of new human milk fat substitutes by enzymatic acidolysis of microalgae oils from Nannochloropsis oculata and Isochrysis galbana

He, Yongjin; Qiu, Changyang; Guo, Zheng; Huang, Jian; Wang, Mingzi; Chen, Bilian

doi:10.1016/j.biortech.2017.04.041

Cited by 40 publications

(30 citation statements)

References 34 publications

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“…Comparing our results with those reported in the literature (Table 1), in solvent-free media, CpLIP2 immobilized in Accurel MP 1000 showed much higher interesterification activity than either the commercial immobilized lipases (He et al, 2017;Pande et al, 2013;Simões et al, 2014) or the noncommercial immobilized lipases (Simões et al, 2014;Tecelão et al, 2012aTecelão et al, , 2012b used for the production of HMFS by acidolysis.…”

Section: Influence Of Ethyl Oleate/tripalmitin Mr On Oleic Acid Incorsupporting

confidence: 82%

Production of Human Milk Fat Substitutes by Interesterification of Tripalmitin with Ethyl Oleate Catalyzed by Candida parapsilosis Lipase/Acyltransferase

Tecelão

Perrier

Dubreucq

et al. 2019

J Americ Oil Chem Soc

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In human milk fat, the saturated fatty acids, namely palmitic acid, are located at the sn-2 position of triacylglycerols (TAG) while unsaturated fatty acids (e.g. oleic acid) are esterified at position sn-1,3. Thus, sn-1,3-dioleoyl-2-palmitoylglycerol (OPO) is the target TAG to be used as human milk fat substitutes (HMFS) in infant formulas. In this study, the noncommercial recombinant lipase/acyltransferase from Candida parapsilosis (CpLIP2) was immobilized in Accurel MP1000, and used as a biocatalyst for the interesterification of tripalmitin with ethyl oleate in a solvent-free medium, to obtain structured lipids used as HMFS. Different molar ratios (MR) of ethyl oleate to tripalmitin (2:1-8:1) were used. After 4 h reaction at 60 C, about 30 mol% of oleic acid incorporation was already observed for all tested MR. An apparent equilibrium was reached after 8-24 h, with 32-51 mol% final incorporation, increasing with the MR. The incorporation of oleic acid into TAG was compared with the maximum predicted values when a random or a sn-1,3-regioselective biocatalyst was used. The obtained values are consistent with the maximum incorporation expected for a sn-1,-3-regioselective enzyme. In fact, the amount of oleic acid at position sn-2 was approximately 15% for all the MR tested, which is explained by the acyl migration phenomenon. CpLIP2 exhibited higher activity than most commercial immobilized lipases (e.g. faster reaction in solvent-free media, low enzyme load, and low MR needed), and showed a recognized sn-1,3 regioselective behavior. Keywords Candida parapsilosis lipase acyltransferase Á Ethyl oleate Á Human milk fat substitute Á sn-1,3 regioselective enzyme Á Structured lipids J Am Oil Chem Soc (2019) 96: 777-787. Abbreviations CpLIP2 recombinant lipase/acyltransferase from Candida parapsilosis FAME fatty acid methyl ester HMF human-milk fat HMFS human-milk fat substitutes MR molar ratio(s) omega-3 PUFA omega-3 polyunsaturated fatty acid(s) OPO 1,3-dioleoyl-2-palmitoylglycerol SL structured lipid(s) TAG triacylglycerol(s)

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Section: Influence Of Ethyl Oleate/tripalmitin Mr On Oleic Acid Incorsupporting

confidence: 82%

Production of Human Milk Fat Substitutes by Interesterification of Tripalmitin with Ethyl Oleate Catalyzed by Candida parapsilosis Lipase/Acyltransferase

Tecelão

Perrier

Dubreucq

et al. 2019

J Americ Oil Chem Soc

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“…447 Human milk fat substitutes with four types of n-3 fatty acids for infant formula were produced via acidolysis of Nannochloropsis oculata rich oil by free fatty acids from Isochrysis galbana in a solvent-free SYSTEM using N435, TL-IM and RM-IM as biocatalysts. 448 A product containing a total of n-3 PUFAs of 13.92-17.12 wt% in the S n -2 position under optimal conditions could be obtained using N435 and Lipozyme TL-IM.…”

Section: View Article Onlinementioning

confidence: 99%

Novozym 435: the “perfect” lipase immobilized biocatalyst?

Ortíz

Ferreira

Barbosa

et al. 2019

Catal. Sci. Technol.

427

360

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“…When applying immobilized enzymes for the industrial production of SLs, several factors have to be considered to fulfill their catalytic potential and maximize the acquisition of the target products. First, for a specific SL, it is required to screen the desired immobilized lipase and determine the optimal processing conditions (for example, substrate ratio, enzyme amount, reaction temperature, time, and pH) (Bassan et al., ; He et al., ; Wang, Wang, Wang, Jin, & Wang, ). Second, it is also important to select suitable reactors.…”

Section: Synthesis Of Slsmentioning

confidence: 99%

“…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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Production of new human milk fat substitutes by enzymatic acidolysis of microalgae oils from Nannochloropsis oculata and Isochrysis galbana

Cited by 40 publications

References 34 publications

Production of Human Milk Fat Substitutes by Interesterification of Tripalmitin with Ethyl Oleate Catalyzed by Candida parapsilosis Lipase/Acyltransferase

Production of Human Milk Fat Substitutes by Interesterification of Tripalmitin with Ethyl Oleate Catalyzed by Candida parapsilosis Lipase/Acyltransferase

Novozym 435: the “perfect” lipase immobilized biocatalyst?

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

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