Lipase‐catalyzed interesterification reactions for human milk fat substitutes production: A review

Soumanou, Mohamed M.; Pérignon, Marlène; Villeneuve, Pierre

doi:10.1002/ejlt.201200084

Cited by 110 publications

(84 citation statements)

References 94 publications

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“…However, the incorporation increased only 1.2 times when lipase load increased from 5% to 20%. According to Soumanou et al (2013), higher enzyme amounts can accelerate the reaction rate and increase the incorporation during acidolysis, although high acyl migration may occur under these conditions. In fact, acyl migration depends on lipase load, enzyme supports with surface charges, water content and water activity, solvent and temperature (Iwasaki and Yamane, 2000;Xu 2000aXu , b, 2003Fernadez-Lafuente, 2010).…”

Section: Structured Lipid Synthesismentioning

confidence: 99%

Incorporation of capric acid in pumpkin seed oil by sn-1,3 regioselective lipase-catalyzed acidolysis

Sousa

Campos

Nunes

et al. 2018

OCL

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-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.Keywords: structured lipid / acidolysis / pumpkin seed oil / capric acid / lipozyme TL IM Résumé -Incorporation d'acide caprique dans de l'huile de pépin de citrouille par acidolyse catalysée par une lipase sn-1,3 régiosélective. Les lipides structurés sont de nouveaux triacylglycérols obtenus en changeant les profils des acides gras (AG) natifs ou par l'incorporation de nouveaux AG souhaités dans le squelette glycérol. Ces graisses modifiées présentent des propriétés médicales et fonctionnelles importantes pour des applications alimentaires. Ce travail vise à synthétiser un lipide structuré de type MLM, qui consiste en des triacylglycérols contenant un AG à chaîne moyenne (M) en positions sn-1,3 et un acide gras à chaîne longue (L) en position sn-2, par acidolyse de l'huile de graine de citrouille avec l'acide caprique, catalysée par une préparation commerciale de lipase de Thermomyces lanuginosa (Lipozyme TL IM). Les réactions ont été effectuées à 45°C, sans solvant, avec un rapport molaire de 1:2 (huile de graines de citrouille: acide caprique) et une quantité fixe de lipase immobilisée de 5 %, 10 %, 15 % ou 20 %. Avec une charge en lipase de 5 %, l'incorporation du C10:0 a augmenté avec le temps jusqu'à 31 h (29,9 ± 0,7 mol %). Des différences significatives ont été observées seulement entre les résultats obtenus avec 5 et 20 % de charge en biocatalyseur. L'expérience suivante a été réalisée avec une charge en lipase de 5 %, à 45°C, un rapport molaire 1:2 et en présence de n-hexane. Les résultats ont montré des rendements d'incorporation lég...

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Section: Structured Lipid Synthesismentioning

confidence: 99%

Incorporation of capric acid in pumpkin seed oil by sn-1,3 regioselective lipase-catalyzed acidolysis

Sousa

Campos

Nunes

et al. 2018

OCL

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“…In this case, the fatty acid (FA) redistribution occurs at random, and the high temperature and pressure conditions affect the final sensory properties of the product, resulting in the need for additional purification (NUNES et al, 2010). Enzymatic interesterification using lipases (EC 3.1.1.3; triacylglycerol acylhydrolases) is advantageous because the milder conditions allow for a process design with fewer unit operations and lower investment requirements (SOUMANOU et al, 2013). Moreover, another advantage is its minimum generation of byproducts, since lipases are highly regioselective in their reactions (MUKHERJEE, 2014).…”

Section: Introductionmentioning

confidence: 99%

Assessing the reaction conditions to mediate the milkfat-soybean oil enzymatic interesterification

Paula

Nunes

Castro

et al. 2016

Braz. J. Food Technol.

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This is an Open Access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Assessing the reaction conditions to mediate the milkfat-soybean oil enzymatic interesterification Determinação das condições reacionais para mediar a interesterificação enzimática da gordura do leite e do óleo de soja SummaryA food grade lipase from Rhizopus oryzae immobilized on a hybrid polysiloxane-polyvinyl alcohol matrix (SiO 2 -PVA) was used as the biocatalyst to mediate the interesterification reactions of a blend containing 65% milkfat and 35% soybean oil. All the reactions occurred in an inert nitrogen atmosphere in cylindrical glass reactors (80 mL) with 40 g of the milkfat-soybean oil blend. The influence of the following variables was evaluated: biocatalyst loading (250-1500 activity units per gram of blend), biocatalyst moisture content (5-20%), temperature (45-60 °C) and incubation time (2-48 h). The reactions were monitored by determining the free fatty acid content, triacylglycerol (TAGs) composition in carbon species, and the consistency of the interesterified (IE) products. The reaction conditions were set based on the parameters that provided a high interesterification yield and good consistency of the final product within the ideal range (200 to 800 gf cm -2 ). Hence the best results were obtained using a biocatalyst loading of 500 U g -1 of blend with 10% moisture content at 45 °C for 4 h. Under these conditions the consistency of the interesterified product was 539.7 ± 38 gf cm -2 . The results demonstrated the potential of the immobilized lipase to alter the TAGs profile of the milkfat-soybean oil blend, allowing for the production of structured lipids.Keywords: Rhizopus oryzae lipase; Milkfat; Soybean oil; Interesterification. ResumoLipase de grau alimentício de Rhizopus oryzae, imobilizada em uma matriz híbrida de polissiloxano-polivinilálcool (SiO 2 -PVA), foi usada como biocatalisador para mediar reações de interesterificação de uma mistura contendo 65% de gordura de leite e 35% de óleo de soja. Todas as reações ocorreram sob atmosfera inerte de nitrogênio, em reatores de vidro cilíndricos (80 mL) com 40 g da mistura. Avaliou-se a influência das seguintes variáveis: carregamento de biocatalisador (250-1.500 unidades de atividade por grama de mistura), umidade do biocatalisador (5-20%), temperatura (45-60 °C) e tempo de incubação (2-48 h). O progresso das reações foi monitorado pela determinação do conteúdo de ácidos graxos livres, da composição em triacilgliceróis (TAGs) em espécies de carbono e da consistência de produtos interesterificados (IE). As condições reacionais foram estabelecidas com base nos parâmetros que proporcionaram alto grau de interesterificação e consistência do produto final dentro da faixa ideal (200 a 800 gf cm -2 ). Neste contexto, os melhores resultados foram obtidos utilizando-se 500 U de biocatalisador por grama de mistura, com 10% de...

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“…The differences in the stereospecific distribution can explain the enhanced absorption of HM lipids. The TAG structure affects the products formed by lipase and helps control FA absorption (Innis, 2011;Soumanou et al, 2013). The hydrolysis of HM results in SFA mainly as sn-2-monoacylglycerides, which are well absorbed.…”

Section: Stereospecific Distribution Of Fas On Tagmentioning

confidence: 99%

“…The unsaturated fatty acids (UFAs) and PUFAs are at the sn-1,3 (outer) positions of the TAG molecules. There is considerable interest in using enzymatic interesterification of edible oils for the synthesis of HM fat substitutes (HMFS) with the physical, chemical, and nutritional properties of HM fat (Djajasoepena et al, 2015;Ghosh et al, 2016;Karabulut et al, 2007;Soumanou et al, 2013). In this sense, there is a need for new analytical tools to evaluate the stereospecific distribution of the FAs in TAGs.…”

Section: Introductionmentioning

confidence: 99%

Toward Precision Nutrition: Commercial Infant Formulas and Human Milk Compared for Stereospecific Distribution of Fatty Acids Using Metabolomics

Lopes

Cañedo

Oliveira

et al. 2018

OMICS: A Journal of Integrative Biology

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Precision nutrition and nutrimetabolomics are emerging omics technology applications in public health. In this context, the infant formula (IF) is a manufactured foodstuff that aims to match the composition of human milk (HM), especially the lipid profile. The IF manufacturers have achieved relative success in matching the predominant fatty acid (FAs) profiles, but the stereospecific structures of the triacylglycerides in HM require deeper analyses with system sciences. We employed NMR-based metabolomics to compare the lipid profiles of 12 commercial IF samples and 10 HM samples. Additionally, vegetables, fish, and microalgae oil as raw materials in IFs were also investigated to understand the lipid profile of IFs. We found that IF has significantly less saturated fatty acids (SFA), higher unsaturated FAs, and similar polyunsaturated fatty acid (PUFA) content, compared with HM. However, the main difference was the stereospecific distribution of FAs: HM samples were associated with a high content of SFAs in the sn-2 position (26.03% -2.93%) and PUFAs in the sn-1,3 position (15.35% -3.94%). The IF had the opposite distribution, with SFAs esterified mainly in the sn-1,3 position (33.07 -4.93%) and PUFAs in the sn-2 position (9.57% -7.05%). Consequently, the hydrolysis of HM results in SFA mainly as sn-2-monoacylglycerides, which are well absorbed. In contrast, the hydrolysis of the IF provided SFA, mainly as free FAs, which tend to bind calcium and form insoluble calcium soaps in the intestine. Taken together, these observations can inform optimal design of infant formulas with a view to precision nutrition.

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Lipase‐catalyzed interesterification reactions for human milk fat substitutes production: A review

Cited by 110 publications

References 94 publications

Incorporation of capric acid in pumpkin seed oil by sn-1,3 regioselective lipase-catalyzed acidolysis

Incorporation of capric acid in pumpkin seed oil by sn-1,3 regioselective lipase-catalyzed acidolysis

Assessing the reaction conditions to mediate the milkfat-soybean oil enzymatic interesterification

Toward Precision Nutrition: Commercial Infant Formulas and Human Milk Compared for Stereospecific Distribution of Fatty Acids Using Metabolomics

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