Enrichment of DHA from Tuna Oil in a Packed Bed Reactor via Lipase‐Catalyzed Esterification

Hong, Seung In; Ma, Na; No, Da Som; Choi, Nakyung; Baik, Ji Yeon; Kim, Chong Tai; Kim, Yangha; Chang, Eugene; Kim, In Hwan

doi:10.1007/s11746-014-2536-9

Cited by 11 publications

(4 citation statements)

References 46 publications

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“…In contrast, 435, as a nonselective lipase, can catalyze transesterification of hydroxyl groups at any position . Therefore, more substrates could be consumed during the transesterification with 435 than those with RM IM and TL IM, yielding the highest content of triacylglycerols with 435 . Accordingly, 435 was selected for transesterification in subsequent studies.…”

Section: Resultsmentioning

confidence: 99%

Two-Stage Enzymatic Preparation of Eicosapentaenoic Acid (EPA) And Docosahexaenoic Acid (DHA) Enriched Fish Oil Triacylglycerols

Zhang

Liu

et al. 2017

J. Agric. Food Chem.

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Fish oil products in the form of triacylglycerols generally have relatively low contents of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and so it is of potential research and industrial interest to enrich the related contents in commercial products. Thereby an economical and efficient two-stage preparation of EPA and DHA enriched fish oil triacylglycerols is proposed in this study. The first stage was the partial hydrolysis of fish oil by only 0.2 wt.‰ AY "Amano" 400SD which led to increases of EPA and DHA contents in acylglycerols from 19.30 and 13.09 wt % to 25.95 and 22.06 wt %, respectively. Subsequently, products of the first stage were subjected to transesterification with EPA and DHA enriched fatty acid ethyl esters (EDEE) as the second stage to afford EPA and DHA enriched fish oil triacylglycerols by using as low as 2 wt % Novozyme 435. EDEEs prepared from fish oil ethyl ester, and recycled DHA and EPA, respectively, were applied in this stage. Final products prepared with two different sources of EDEEs were composed of 97.62 and 95.92 wt % of triacylglycerols, respectively, with EPA and DHA contents of 28.20 and 21.41 wt % for the former and 25.61 and 17.40 wt % for the latter. Results not only demonstrate this two-stage process's capability and industrial value for enriching EPA and DHA in fish oil products, but also offer new opportunities for the development of fortified fish oil products.

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Section: Resultsmentioning

confidence: 99%

Two-Stage Enzymatic Preparation of Eicosapentaenoic Acid (EPA) And Docosahexaenoic Acid (DHA) Enriched Fish Oil Triacylglycerols

Zhang

Liu

et al. 2017

J. Agric. Food Chem.

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“…In our previous study (No et al, 2015), pinolenic acid, which is one of Δ-5 fatty acids in pine nut oil, was efficiently enriched from initial value of 13% to 42.6% in the unesterified fatty acid fraction after Candida rugosa lipase-catalyzed esterification of pine nut oil fatty acid with lauryl alcohol. In other study (Baik et al, 2014), the stearidonic acid (18:4), which is one of ω-3 PUFAs, was enriched up to 54.1% from 14% of echium oil fatty acid by a two-step lipase-catalyzed esterification.…”

Section: Introductionmentioning

confidence: 83%

“…The fatty acids used for concentration of DHA were prepared from a tuna oil (Kwangjin Technology, Seoul, Republic of Korea) by saponification according to the method of Hong et al (2014). A low temperature bath employed in solvent crystallization was purchased from Eyela (Model PSL‐2000, Tokyo, Japan).…”

Section: Methodsmentioning

confidence: 99%

Concentration of docosahexsaenoic acid from tuna oil by a combination of solvent crystallization and lipase‐catalyzed ethanolysis

Park,

Wee,

Lee

et al. 2024

J Americ Oil Chem Soc

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The docosahexaenoic acid (DHA) was concentrated from tuna oil fatty acid using solvent crystallization combined with lipase‐catalyzed ethanolysis. In the first step, solvent crystallization was carried out to concentrate DHA from tuna oil fatty acid using acetonitrile as a solvent. The optimal conditions of solvent crystallization were the crystallization temperature of −40°C and the fatty acid to solvent ratio of 1:8 (w/v). This step increased the DHA content in the original tuna oil fatty acid from 22% up to 61%. In the second step, lipase‐catalyzed ethanolysis was conducted with DHA‐enriched fatty acid from the first step using Lipozyme RM IM (from Rhizomucor miehei) as a biocatalyst. The optimum conditions of this second step were the reaction temperature of 20°C and the molar ratio of 1:1 (fatty acid to ethanol). Overall, DHA enrichment with purity of 85% was obtained by the two step processes.

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“…The enrichment of EPA and DHA in fats and oils can be achieved via physical, chemical, or enzymatic methods such as low-temperature solvent crystallization, supercritical fluid extraction, urea complexation, and silver nitrate complexation [ 80 , 81 , 82 , 83 , 84 , 85 ]. Via these techniques, EPA and DHA in fish oil are first hydrolyzed or trans-esterified into their free form or ethyl ester before enrichment.…”

Section: Enzymatic Preparation and Application Of Slsmentioning

confidence: 99%

Future of Structured Lipids: Enzymatic Synthesis and Their New Applications in Food Systems

Zhou

Lee

Mao

et al. 2022

Foods

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Structured lipids (SLs) refer to a new type of functional lipid obtained by modifying natural triacylglycerol (TAG) through the restructuring of fatty acids, thereby altering the composition, structure, and distribution of fatty acids attached to the glycerol backbones. Due to the unique functional characteristics of SLs (easy to absorb, low in calories, reduced serum TAG, etc.), there is increasing interest in the research and application of SLs. SLs were initially prepared using chemical methods. With the wide application of enzymes in industries and the advantages of enzymatic synthesis (mild reaction conditions, high catalytic efficiency, environmental friendliness, etc.), synthesis of SLs using lipase has aroused great interest. This review summarizes the reaction system of SL production and introduces the enzymatic synthesis and application of some of the latest SLs discussed/developed in recent years, including medium- to long-chain triacylglycerol (MLCT), diacylglycerol (DAG), EPA- and DHA-enriched TAG, human milk fat substitutes, and esterified propoxylated glycerol (EPG). Lastly, several new ways of applying SLs (powdered oil, DAG plastic fat, inert gas spray oil, and emulsion) in the future food industry are also highlighted.

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Enrichment of DHA from Tuna Oil in a Packed Bed Reactor via Lipase‐Catalyzed Esterification

Cited by 11 publications

References 46 publications

Two-Stage Enzymatic Preparation of Eicosapentaenoic Acid (EPA) And Docosahexaenoic Acid (DHA) Enriched Fish Oil Triacylglycerols

Two-Stage Enzymatic Preparation of Eicosapentaenoic Acid (EPA) And Docosahexaenoic Acid (DHA) Enriched Fish Oil Triacylglycerols

Concentration of docosahexsaenoic acid from tuna oil by a combination of solvent crystallization and lipase‐catalyzed ethanolysis

Future of Structured Lipids: Enzymatic Synthesis and Their New Applications in Food Systems

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