Production of structured triacylglycerols rich in palmitic acid at sn-2 position and oleic acid at sn-1,3 positions as human milk fat substitutes by enzymatic acidolysis

Esteban, Luis; Jiménez, M.J.; Hita, Estrella; González, P.; Martín, Lorena; Robles, Alfonso

doi:10.1016/j.bej.2011.01.009

Cited by 66 publications

(65 citation statements)

References 27 publications

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“…Total palmitic acid incorporation of the present work was found to be higher than those results. Esteban et al (2011) obtained incorporation values similar to the current study. They used palmitic acid as the acyl donor for the incorporation at the sn-2 position of palm stearin via enzymatic reaction.…”

Section: Verification Of the Modelssupporting

confidence: 91%

“…They used palmitic acid as the acyl donor for the incorporation at the sn-2 position of palm stearin via enzymatic reaction. Esteban et al (2011) produced a SL as a HMFS with total palmitic acid amount of 39 mol/100 mol total FA of which 66% was present at the sn-2 position after the acidolysis and purification steps. Even though total palmitic acid amount was higher than that of HMF, the sn-2 position of the product contained similar palmitic acid amount as in HMF.…”

Section: Verification Of the Modelsmentioning

confidence: 99%

“…Amaranth oil was enriched at the sn-2 position with ethyl palmitate through chemical and enzymatic reactions by Pina-Rodriguez and Akoh (2009a). In another study, palm stearin was enriched with palmitic acid at the sn-2 position as a result of enzymatic reactions (Esteban et al, 2011). Teichert and Akoh (2011b) used stearidonic acid enriched soybean oil and tripalmitin to produce SLs enriched with palmitic acid at the sn-2 position through enzymatic reactions using Novozym 435 or Lipozyme TL IM as enzymatic catalyst and optimized the reaction conditions by response surface methodology (RSM).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Enrichment of sn-2 position of hazelnut oil with palmitic acid: Optimization by response surface methodology

Turan

Şahin‐Yeşilçubuk

Akoh

2013

LWT - Food Science and Technology

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Section: Verification Of the Modelssupporting

confidence: 91%

Section: Verification Of the Modelsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Enrichment of sn-2 position of hazelnut oil with palmitic acid: Optimization by response surface methodology

Turan

Şahin‐Yeşilçubuk

Akoh

2013

LWT - Food Science and Technology

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“…In typical HMF, the total fatty acid composition is about 21.8% palmitic acid and 33.9% oleic acid [16]. About 70% of the palmitic acid of HMF is in the sn-2 position; alternatively stated, 57.2% of the sn-2 position is occupied by palmitic acid [16].…”

Section: Introductionmentioning

confidence: 99%

Structure-Guided Modification of Rhizomucor miehei Lipase for Production of Structured Lipids

et al. 2013

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To improve the performance of yeast surface-displayed Rhizomucor miehei lipase (RML) in the production of human milk fat substitute (HMFS), we mutated amino acids in the lipase substrate-binding pocket based on protein hydrophobicity, to improve esterification activity. Five mutants: Asn87Ile, Asn87Ile/Asp91Val, His108Leu/Lys109Ile, Asp256Ile/His257Leu, and His108Leu/Lys109Ile/Asp256Ile/His257Leu were obtained and their hydrolytic and esterification activities were assayed. Using Discovery Studio 3.1 to build models and calculate the binding energy between lipase and substrates, compared to wild-type, the mutant Asp256Ile/His257Leu was found to have significantly lower energy when oleic acid (3.97 KJ/mol decrease) and tripalmitin (7.55 KJ/mol decrease) were substrates. This result was in accordance with the esterification activity of Asp256Ile/His257Leu (2.37-fold of wild-type). The four mutants were also evaluated for the production of HMFS in organic solvent and in a solvent-free system. Asp256Ile/His257Leu had an oleic acid incorporation of 28.27% for catalyzing tripalmitin and oleic acid, and 53.18% for the reaction of palm oil with oleic acid. The efficiency of Asp256Ile/His257Leu was 1.82-fold and 1.65-fold that of the wild-type enzyme for the two reactions. The oleic acid incorporation of Asp256Ile/His257Leu was similar to commercial Lipozyme RM IM for palm oil acidolysis with oleic acid. Yeast surface-displayed RML mutant Asp256Ile/His257Leu is a potential, economically feasible catalyst for the production of structured lipids.

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“…In another study, the enzyme from Rhizopus oryzae was used in the reaction between palm stearin enriched with palmitic acid and oleic acid (Esteban et al 2011). The enzyme was specific in the incorporation of oleic acid at the sn-1, 3 positions of the TAG.…”

Section: Regiospecific Distributionmentioning

confidence: 99%

Lipase catalyzed interesterification of Amazonian patauá oil and palm stearin for preparation of specific-structured oils

2015

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This study showed that enzymatic interesterification of Amazonian oils could be an important tool in order to produce new oils with physicochemical properties that improve the applications of these raw materials. Structured oils of Amazonian patauá oil and palm stearin using two lipases were produced in three different enzymatic systems: first, a crude lipase from the fungus Rhizopus sp (a microorganism isolated in our laboratory); second, a commercial lipase; and third, to check any synergistic effect, a mixture of both lipases (Rhizopus sp and commercial). The lipase from Rhizopus sp was specific in the incorporation of oleic acid at the sn-1,3 positions of the triacylglycerol, resulting in an oil richer in saturated fatty acid in the sn-2 position. This enzyme, produced by solid-state fermentation, even though crude, was fatty acid and positional specific and able to operate at low concentration (2.5 %, w/w). In the second enzyme system, the commercial lipase from Thermomyces lanuginosus was not specific in the tested conditions; there was no change in the distribution of saturated and unsaturated fatty acids in the three positions of the triacylglycerol profile, there was only a replacement by the type of fatty acid at the same position. In the third enzyme system, the mixture of both lipases shows no synergic effect. The structured oils retained the concentration of bioactive α-and γ-tocopherol in the three enzyme systems.Triacylglycerol classes and Thermal behavior tests indicated the formation of more homogeneous triacylglycerols, especially the mono and di-unsaturated.

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Production of structured triacylglycerols rich in palmitic acid at sn-2 position and oleic acid at sn-1,3 positions as human milk fat substitutes by enzymatic acidolysis

Cited by 66 publications

References 27 publications

Enrichment of sn-2 position of hazelnut oil with palmitic acid: Optimization by response surface methodology

Enrichment of sn-2 position of hazelnut oil with palmitic acid: Optimization by response surface methodology

Structure-Guided Modification of Rhizomucor miehei Lipase for Production of Structured Lipids

Lipase catalyzed interesterification of Amazonian patauá oil and palm stearin for preparation of specific-structured oils

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