Synthesis of structured lipids by two enzymatic steps: Ethanolysis of fish oils and esterification of 2-monoacylglycerols

Muñío, María del Mar; Robles, Alfonso; Esteban, Luis; González, P.; Molina, Emilio

doi:10.1016/j.procbio.2009.03.002

Cited by 52 publications

(30 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, ethanolysis reaction was carried out in pure ethanol without the use of an additional solvent as reaction medium. Whereas, other authors described the production of 2‐MAGs by ethanolysis using acetone or hexane as reaction medium. The advantage of using pure ethanol, besides of being a green solvent allowed in food industry, lies in the fact that solvent is critical to acyl migration rate.…”

Section: Resultssupporting

confidence: 92%

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

View full text Add to dashboard Cite

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.

show abstract

Section: Resultssupporting

confidence: 92%

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

View full text Add to dashboard Cite

show abstract

“…To date, structured TAGs containing specific FAs such as EPA, AA, and DHA [92][93][94] or palmitic acid [95,96] have been reported. However, specific papers on GLA and SDA-containing structured TAGs synthesis by using alcoholysis have not been reported.…”

Section: Enzymatic Methodsmentioning

confidence: 99%

Gamma‐linolenic and stearidonic acids: Purification and upgrading of C18‐PUFA oils

Guil‐Guerrero

Rincón‐Cervera

Venegas‐Venegas

2010

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

“…The fatty acid composition of each of the lipidic species was determined by preparative TLC followed by gas chromatography (GC), following the methods already described in various articles [26][27][28][29].…”

Section: Identification Of the Reaction Products And Determination Ofmentioning

confidence: 99%

Production of triacylglycerols rich in palmitic acid at position 2 as intermediates for the synthesis of human milk fat substitutes by enzymatic acidolysis

Jiménez

Esteban

Robles

et al. 2010

Process Biochemistry

Self Cite

View full text Add to dashboard Cite

This paper studies the synthesis of triacylglycerols (TAGs) rich in palmitic acid (PA) at position 2, from palm oil stearin (POS), a vegetable oil highly rich in this acid (60%). The developed process consists of two steps: (1) obtaining PA enriched free fatty acids (FFAs), and (2) enrichment of POS in PA by acidolysis of this oil with PA enriched FFAs, catalyzed by lipase Novozym 435. In step (1) two PA enriched FFA mixtures were obtained: one by saponification of POS, and a PA concentrate (75.1% PA) obtained by crystallization at low temperature in solvents. The latter was obtained carrying out two crystallizations in acetone at -24 and -20 ºC, from which PA was recovered in the solid phases with a total yield of 84%. These PA enriched FFA mixtures were used in step (2) of acidolysis of POS, along with commercial PA (98% PA). In this acidolysis step four factors were studied: temperature, hexane/reaction mixture ratio, FFA/POS molar ratio and the intensity of treatment (IOT = lipase amount × reaction time/POS amount). The best results (TAGs with 79% PA and 75% PA at position 2) were obtained with commercial PA, at 37 ºC, 10 mL hexane/g reaction mixture, a FFA/POS molar ratio 3:1 (1:1 w/w) and an IOT = 9.6 g lipase × h/g POS (for example 48 h, 10 g lipase and 50 g POS). PA enriched TAGs were purified neutralizing the FFAs by KOH hydroethanolic solutions and extracting the TAGs with hexane. In this way 99% pure acylglycerols (TAG+DAG) were obtained; the recovery yield of this purification step was 95%. The experiments carried out with POS demonstrated that it is possible to use only this oil (60% PA, 23% PA at position 2) as a source of PA to obtain a TAG with 70.7% PA and 70.5% PA at position 2. This process consists of four steps:(1) saponification of POS, (2) crystallization of FFAs to obtain PA enriched FFAs (75.1% PA), (3) acidolysis of POS with these FFAs, catalyzed with Novozym 435, to produce PA enriched TAGs at position 2 (70.5% PA) and (4) purification of TAGs to obtain approximately 95% purity and yield. These PA enriched TAGs could be used to obtain structured TAGs rich in PA at position 2 and in oleic acid at positions 1 and 3 (OPO), which is the principal TAG of human milk fat.

show abstract

Synthesis of structured lipids by two enzymatic steps: Ethanolysis of fish oils and esterification of 2-monoacylglycerols

Cited by 52 publications

References 31 publications

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

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

Gamma‐linolenic and stearidonic acids: Purification and upgrading of C18‐PUFA oils

Production of triacylglycerols rich in palmitic acid at position 2 as intermediates for the synthesis of human milk fat substitutes by enzymatic acidolysis

Contact Info

Product

Resources

About