Pancreatic lipase selectively hydrolyses DPA over EPA and DHA due to location of double bonds in the fatty acid rather than regioselectivity

Akanbi, Taiwo O.; Sinclair, Andrew J.; Barrow, Colin J.

doi:10.1016/j.foodchem.2014.03.092

Cited by 56 publications

(28 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This indicates that ultrasound may disrupt the structure of lipase, in turn reducing activity and shortening its service life in the reaction. These observations are, however, inconsistent with those reported by Akanbi, Sinclair, and Barrow (2014) and Lerin et al (2014), which may be attributed to different types and selectivities of enzymes used in the reaction.…”

Section: Reusability Of Lipozymecontrasting

confidence: 86%

Ultrasonic‐pretreated lipase‐catalyzed synthesis of medium–long–medium lipids using different fatty acids as sn‐2 acyl‐site donors

Wang

Xie

Johnson

et al. 2019

Food Science & Nutrition

View full text Add to dashboard Cite

The current work aimed to evaluate the effect of ultrasonic treatment on the enzymatic transesterification of medium–long–medium (MLM) lipids using 2‐monoacylglycerol, bearing distinct fatty acids at the sn ‐2 position with palmitic acid, octadecanoic acid, oleic acid, eicosapentaenoic acid, and docosahexaenoic acids as sn ‐2 acyl donors. The effects of ultrasonic treatment conditions, including substrate concentration, reaction temperature and time, and enzyme loading, on the insertion of fatty acids into the sn ‐2 acyl position of MLM lipids were investigated. The data showed that low‐frequency ultrasonic treatment could remarkably improve the insertion rate of polyunsaturated fatty acid (PUFA) into the sn ‐2 position of MLM lipids, compared with the conventional treatment method. By increasing the ultrasonic frequency from 20 to 30 KHz, while maintaining power at 150 W, the rate of synthesis of monounsaturated fatty acid and PUFA increased from 23.7% and 26.8% to 26.6% and 32.4% ( p < 0.05), respectively. Moreover, ultrasonic treatment reduced the optimum reaction temperature from 45 to 35°C. However, the activity of Lipozyme RM‐IM treated with ultrasound considerably declined from 31.10% to 26.90% ( p < 0.05) after its fourth cycle, which was lower than that without ultrasonic treatment. This work provokes new routes for the utilization of ultrasonic technology in the synthesis of MLM lipids using different fatty acids as sn ‐2 acyl donors.

show abstract

Section: Reusability Of Lipozymecontrasting

confidence: 86%

Ultrasonic‐pretreated lipase‐catalyzed synthesis of medium–long–medium lipids using different fatty acids as sn‐2 acyl‐site donors

Wang

Xie

Johnson

et al. 2019

Food Science & Nutrition

View full text Add to dashboard Cite

show abstract

“…This type of substrate specificity owing to the fact that lipases are quite sensitive to the double bond positions within fatty acid groups. Specifically, lipases show less catalytic rate when double bonds are located nearest the carboxyl group, such as DHA . The chemical structure of DHA implies a difficulty for lipases into the FAEEs incorporation, and therefore transesterification reaction rendered minor product yields in comparison with EPA‐EEs.…”

Section: Resultsmentioning

confidence: 54%

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

“…This is in agreement with the known kinetics of pancreatic lipase with increasing chain length. 7 Furthermore, differences observed between breast milk-fed and formula-fed infants are unlikely to be explained by differences in the sn position of LCPUFAs in breast milk compared to formula as the standard oils used to supplement formulas have, in contrast to breast milk, triglycerides with two versus one LCPUFA esterified per triglyceride molecule, LCPUFAs in all three sn positions, versus predominantly the sn-2 and sn-3 positions, and a greater proportion of LCPUFAs of the total fatty acid pool in the sn-2 position compared to that found in breast milk. 8 Thus, the data represented are consistent with limited pancreatic lipase production by the preterm infant with lipase being present in breast milk but not in formula.…”

Section: Discussionmentioning

confidence: 99%

Factors Determining Optimal Fatty Acid Absorption in Preterm Infants

Martin

Cheesman

Brown

et al. 2016

J. pediatr. gastroenterol. nutr.

View full text Add to dashboard Cite

Objectives To quantify absorption coefficients of specific fatty acids in preterm infants as a function of diet, formula (F) or breast milk (BM), and postnatal age; and, to identify the fatty acid structural characteristics that determine optimal fatty acid absorption. Methods Fatty acids from dietary and fecal samples were extracted and quantified by gas chromatography-mass spectroscopy. Fatty acid absorption coefficients (FA-CFAs) were calculated by comparing the total amount of fatty acids supplied by the diet to the amount quantified in the total fecal output over a 3-day period. Results 18 infants (BM=8; F=10) were studied at 2 weeks of age and 20 infants (BM=10; F=10) were studied at 6 weeks of age. FA-CFAs decreased with increasing carbon length in formula-fed infants at 2 and 6 weeks. Results were similar, but less in magnitude in breast milk-fed infants at 2 weeks with no difference at 6 weeks. Conclusions Preterm infants fed formula demonstrated lower FA-CFAs as a function of increasing carbon length. This is consistent with limited pancreatic lipase production and with lipase being present in breast milk but not in formula. The fact that this pattern was seen in BM-fed infants at 2 weeks but not 6 weeks of age suggests that intestinal immaturity may also play a role in impaired fatty acid absorption. These data highlight principles that need to be considered to optimize delivery and absorption of dietary LCPUFAs in preterm infants.

show abstract

Pancreatic lipase selectively hydrolyses DPA over EPA and DHA due to location of double bonds in the fatty acid rather than regioselectivity

Cited by 56 publications

References 35 publications

Ultrasonic‐pretreated lipase‐catalyzed synthesis of medium–long–medium lipids using different fatty acids as sn‐2 acyl‐site donors

Ultrasonic‐pretreated lipase‐catalyzed synthesis of medium–long–medium lipids using different fatty acids as sn‐2 acyl‐site donors

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

Factors Determining Optimal Fatty Acid Absorption in Preterm Infants

Contact Info

Product

Resources

About