Production of stearidonic acid-rich triacylglycerol via a two-step enzymatic esterification

Kim, Nam Ho; Kim, Heejin; Choi, Nakyung; Kim, Yangha; Kim, Byung Hee; Kim, In Hwan

doi:10.1016/j.foodchem.2018.07.121

Cited by 15 publications

(13 citation statements)

References 25 publications

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“…Several researchers attempted experiments for the synthesis of TAG from FA and glycerol using Lipozyme TL IM, they did not achieve successful results (Oh et al, 2022). In our previous study (Kim et al, 2019), Lipozyme TL IM was used for the synthesis of SDA‐enriched TAG from glycerol and FA, but Novozym 435 was required for the first 2 h of the reaction. However, in the current study, GLA rich TAG was synthesized with only Lipozyme TL IM as a biocatalyst.…”

Section: Resultsmentioning

confidence: 99%

Preparation of γ‐linolenic acid rich triacylglycerol from borage oil via a two‐step lipase‐catalyzed reaction

Yoon

Lee

Kim

et al. 2023

J Americ Oil Chem Soc

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γ‐Linolenic acid (GLA) rich triacylglycerol (TAG) was successfully synthesized from glyceride, instead of glycerol, and fatty acid (FA) via Lipozyme TL IM‐catalyzed esterification as a novel strategy. In the first step, GLA was enriched into glyceride fraction from borage oil by Candida rugosa lipase‐catalyzed hydrolysis. The glyceride was separated from the reaction mixture by molecular distillation. GLA was enriched from 20.64% in borage oil to 45.94% in the glyceride fraction under optimum conditions. In the second step, the Lipozyme TL IM‐catalyzed synthesis of TAG was carried out with the glyceride, and the FA obtained by saponification of a portion of the glyceride. The optimum conditions were the temperature of 50°C, the enzyme loading of 10%, and the vacuum level of 20 mmHg, respectively. The maximum TAG content of approximately 92% was achieved after 12 h under the optimum conditions.

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Section: Resultsmentioning

confidence: 99%

Preparation of γ‐linolenic acid rich triacylglycerol from borage oil via a two‐step lipase‐catalyzed reaction

Yoon

Lee

Kim

et al. 2023

J Americ Oil Chem Soc

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“…Differences in the structure and composition of EPA and DHA in different lipid or acyl groups can affect the function of Omega-3 lipids. Polyunsaturated fatty acids in the form of acylglycerols are more easily absorbed by the body and have higher antioxidant capacity than free fatty acid and ethyl ester polyunsaturated fatty acids [ 28 , 29 ]. Ding et al found that the bioavailability of DHA in the form of TAG was higher than that in other forms, which is more likely to be digested and absorbed [ 30 ].…”

Section: Results and Analysismentioning

confidence: 99%

Comparative Lipidomics Profiling of Acylglycerol from Tuna Oil Selectively Hydrolyzed by Thermomyces Lanuginosus Lipase and Candida Antarctica Lipase A

Xuan

Wang

Xia

et al. 2022

Foods

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Lipase hydrolysis is an effective method to develop different functional types of lipids. In this study, tuna oil was partially hydrolyzed at 30% and 60% by Thermomyces lanuginosus lipase (TL 100 L) and Candida Antarctica lipase A (ADL), respectively, to obtain lipid-modified acylglycerols. The lipidomic profiling of th4 acylglycerols was investigated by UPLC-Q-TOF-MS and GC–MS to clarify the lipid modification effect of these two lipases on tuna oil. The results showed that 247 kinds of acylglycerols and 23 kinds of fatty acids were identified in the five samples. In the ADL group, the content of triacylglycerols (TAG) and diacylglycerols (DAG) increased by 4.93% and 114.38%, respectively, with an increase in the hydrolysis degree (HD), while there was a decreasing trend in the TL 100 L group. TL 100 L had a better enrichment effect on DHA, while ADL was more inclined to enrich EPA and hydrolyze saturated fatty acids. Cluster analysis showed that the lipids obtained by the hydrolysis of TL 100 L and ADL were significantly different in the cluster analysis of TAG, DAG, and monoacylglycerols (MAG). TL 100 L has strong TAG selectivity and a strong ability to hydrolyze acylglycerols, while ADL has the potential to synthesize functional lipids containing omega-3 PUFAs, especially DAG.

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“…In another work, Kim et al produced an SDA‐rich TAG (TAG conversion of ca. 86.4 wt%) via a two‐step lipase‐catalyzed esterification of SDA‐rich fatty acid with glycerol using commercial biocatalysts, but using longer reaction times (12 hour) (Kim et al, 2019). In any case, none of these studies involved the previous production of the oil to be used in the further enzymatic reactions.…”

Section: Resultsmentioning

confidence: 99%

Integrated Green and Enzymatic Process to Produce Omega‐3 Acylglycerols from Echium plantagineum Using Immobilized Lipases

Castejón

Señoráns

2020

J Americ Oil Chem Soc

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This work presents an original approach to develop an integrated process to improve the nutritional characteristics of natural oils, starting with the extraction from raw material by ecofriendly methods, followed by the production of novel acylglycerols using immobilized lipases. Specifically, 2‐monoacylglycerols (2‐MAG) enriched in omega‐3 stearidonic acid (SDA) were synthesized by selective ethanolysis of extracted Echium plantagineum oil using the lipase from Thermomyces lanuginosus (TLL). Different reaction conditions were investigated to minimize acyl migration and to ensure the purity of final products. The biocatalyst produced in our laboratory by the immobilization of TLL on Sepabeads C‐18 reached the maximum theoretical amount of 2‐MAG (33%) in only 2 hour at mild reaction conditions (25 °C), achieving a product enriched in omega‐3 SDA (up to 25%). Moreover, the produced biocatalyst exhibited higher stability than commercial lipases. The average activity after five cycles was 71%, allowing several reutilization cycles and developing a feasible enzymatic process. Finally, 2‐MAG were used as starting material to synthesize structured triacyclglycerols (STAG) through transesterification with caprylic acid ethyl esters using the lipase from Rhizomucor miehei (RML) in solvent‐free systems. The use of molecular sieves in combination with RML immobilized on Sepabeads C‐18 was demonstrated to be an extraordinarily fast strategy to produce pure STAG (100% in 1 hour), four times higher than the activity showed by commercial biocatalyst. Thus, the enzymatic processes developed in this study open a range of possibilities to synthesize omega‐3 acylglycerols with improved characteristics, proving the usefulness of immobilized lipases to produce novel lipids.

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Production of stearidonic acid-rich triacylglycerol via a two-step enzymatic esterification

Cited by 15 publications

References 25 publications

Preparation of γ‐linolenic acid rich triacylglycerol from borage oil via a two‐step lipase‐catalyzed reaction

Preparation of γ‐linolenic acid rich triacylglycerol from borage oil via a two‐step lipase‐catalyzed reaction

Comparative Lipidomics Profiling of Acylglycerol from Tuna Oil Selectively Hydrolyzed by Thermomyces Lanuginosus Lipase and Candida Antarctica Lipase A

Integrated Green and Enzymatic Process to Produce Omega‐3 Acylglycerols from Echium plantagineum Using Immobilized Lipases

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