Synthesis of 2‐monoglycerides by alcoholysis of palm oil and tuna oil using immobilized lipases

Wongsakul, Sirirung; Prasertsan, Poonsuk; Bornscheuer, Uwe T.; H‐Kittikun, Aran

doi:10.1002/ejlt.200390019

Cited by 45 publications

(27 citation statements)

References 16 publications

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“…Among them Lipase DF 15 exhibited a typo-selectivity leading to a strong discrimination against DHA while Lipase PS showed high deacylation activity without any selectivity. Similar discrimination against DHA has been already reported for alcoholysis with other enzymes (Wongsakul et al 2003;Halldorsson et al 2004). …”

Section: Resultssupporting

confidence: 66%

Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study

et al. 2009

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Non-enzymatic acyl migration could be counter-productive for the preparation of structured phospholipids with docosahexaenoic acid (DHA) at a designated position. Therefore enzymatic approaches have been developed to investigate acyl migration. First, acyl migration from sn-2 to sn-1 position has been set into relief by a three step enzymatic method using a typo-selective lipase, a phospholipase A2 and a non-selective lipase. The effect of reaction temperature on acyl migration from sn-2 to sn-1 was monitored: lowering the reaction temperature from 40 to 30 degrees C allowed a reduction of DHA migration rate of 40%. Secondly, acyl migration from sn-1 to sn-2 position was negligible. This last result was obtained through the study of structured phosphatidylcholine selective deacylation using a phospholipase A2.

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Section: Resultssupporting

confidence: 66%

Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study

et al. 2009

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“…Moreover, Moreno‐Perez et al described the synthesis of DHA TAGs catalyzed by different immobilized lipases achieving the best production yield with CAL‐B. Wongsakul et al found that CAL‐B discriminates DHA from EPA and can therefore be used for the selective enrichment of the more desirable DHA . Zhang et al investigated the production of TAGs enriched in EPA and DHA from fish oil using the same lipases than in the present work, and also described the same incorporation degree order of CAL‐B > TLL > RML.…”

Section: Resultsmentioning

confidence: 99%

Strategies for Enzymatic Synthesis of Omega‐3 Structured Triacylglycerols from Camelina sativa Oil Enriched in EPA and DHA

Castejón

Señoráns

2019

Euro J Lipid Sci & Tech

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Enzymatic production of enriched eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) structured triacylglycerols (STAGs) is done in a two‐step reaction from a new source of omega‐3 α‐linolenic acid (ALA), Camelina sativa oil. A fast‐pressurized liquid extraction method with ethyl acetate as green solvent is used to produce camelina oil with a 39.3% yield in less than 20 min. In a first stage, camelina oil with a 29.7% of ALA is used to enzymatically produce 2‐monoacylglycerols (2‐MAGs) with high ALA composition in position sn‐2 (49.8% of ALA) using Lipozyme TL IM at 25 °C. For omega‐3 incorporation into STAGs, several lipases are studied, with 2‐MAG and omega‐3 FAEEs at different ratios (1:5, 1:10, and 1:20 (w/w)), 10% (w/w) of biocatalyst at 35 °C. STAGs yields reached with EPA ethyl esters are notably higher than using DHA‐EE. Lipase from Candida antarctica B (CAL‐B) and Thermomyces lanuginosus (TLL) incorporate EPA into STAGs in the same degree, 95.1 and 95.5%, respectively. However, for enriched DHA STAGs, maximum reaction yield is reached with CAL‐B (81.0%). The transesterification method of 2‐MAGs from vegetable omega‐3 sources like camelina oil, with marine EPA and DHA FAEEs, opens new approaches for developing VLC‐PUFA fortified functional foods. Practical Applications: Results provided in this research not only demonstrate the efficiency of this enzymatic method for enriching camelina oil in EPA and DHA, but offer a very effective strategy for the development of omega‐3‐enriched products from other vegetable oil sources like chia or echium as ingredients for functional foods with recognized health claims for applications in nutraceutical and food industries. Camelina oil proved to be an excellent source to enzymatically produce 2‐MAGs enriched in omega‐3 ALA. Moreover, lipase screening with commercial biocatalysts establish the most appropriate strategy to reach maximum STAGs yields with direct application in industry. Tested lipases exhibit different degree of substrate specificity toward EPA and DHA, omega‐3 acids not present in natural seed oils. Thus, CAL‐B seems to be the most suitable lipase to produce high content EPA and DHA enriched STAGs from camelina oil as new food ingredients for nutraceutical applications. Enzymatic production of structured TAGs enriched in EPA and DHA is done in a two‐step reaction from a natural source of omega‐3 ALA, camelina oil, studying reaction kinetics and characterizing isolated products.

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“…They suggested that this lipase showed strict regiospecificity in the presence of excess ethanol. Wongsakul and coworkers [16] evaluated the synthesis of 2-MAG from palm and tuna oils by ethanolysis in organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Optimization of the synthesis of lower glycerides rich in unsaturated fatty acid residues obtained via enzymatic ethanolysis of sesame oil

Criado

Otero

2010

Euro J Lipid Sci & Tech

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The lipases Novozym 435, Lipozyme TL IM and Lipozyme RM IM were employed in the production of lower acylglycerols (LG), i.e. mono-(MAG) and diacylglycerols (DAG), rich in unsaturated fatty acids from sesame oil in batch reactors. The effect of the molar ratio of ethanol to fatty acids on the reusability of these immobilized lipases was studied in detail. The effects of pretreatment on lipase activity for ethanolysis were investigated. Glycerol had a strong product inhibition effect on the ethanolysis reaction, and a relatively large excess of ethanol was necessary to remove the glycerol adsorbed on these biocatalysts. The enzymatic activity was drastically reduced by addition of water to the reaction medium. The presence of organic solvents (hexane and acetone) did not favor the production of LG. For the Novozym 435-catalyzed reaction, optimum conditions were a molar ratio of ethanol to fatty acid residues of 5 : 1, 15 wt-% lipase and 50 7C. For Lipozyme TL IM, the optimum conditions were a molar ratio of ethanol to fatty acid residues of 5 : 1, 20 wt-% biocatalyst, and 30 7C. Novozym 435 and Lipozyme TL IM produced LG with molar ratios of unsaturated to saturated fatty acids of 20.4 in 1 h and 25.3 in 5 h, respectively. In the original oil, this ratio was 5. For trials conducted under optimum conditions, the products from the Novozym 435 trials contained 21.8 wt-% triacylglycerols (TAG), 24 wt-% DAG and 54.2 wt-% MAG. The products of the Lipozyme TL IM trials consisted of 12.9 wt-% DAG and 87.1 wt-% MAG. No TAG species were detected.

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Synthesis of 2‐monoglycerides by alcoholysis of palm oil and tuna oil using immobilized lipases

Cited by 45 publications

References 16 publications

Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study

Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study

Strategies for Enzymatic Synthesis of Omega‐3 Structured Triacylglycerols from Camelina sativa Oil Enriched in EPA and DHA

Optimization of the synthesis of lower glycerides rich in unsaturated fatty acid residues obtained via enzymatic ethanolysis of sesame oil

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