Increasing Stearidonic Acid (SDA) in Modified Soybean Oil by Lipase‐Mediated Acidolysis

Kleiner, Leslie; Vázquez, Luís; Akoh, Casimir C.

doi:10.1007/s11746-012-2022-1

Cited by 4 publications

(7 citation statements)

References 28 publications

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“…The average and standard deviation of triplicate analyses are reported. The fatty acid profiles of MSO and LTC-TAG were in agreement with those reported previously [11,15].…”

Section: Pancreatic Lipase-catalyzed Sn-2 Positional Analysissupporting

confidence: 91%

“…We have previously reported the production of SL with SDA contents of 37.61 %. These were synthesized by the acidolysis reaction between MSO and FFA obtained from the low temperature crystallization of MSO (LTC-FFA) [15]. We also reported the production of SLs containing 53.46 % SDA by the acidolysis reaction between TAG obtained from low temperature crystallization of MSO (LTC-TAG) and LTC-FFA [15].…”

Section: Introductionmentioning

confidence: 98%

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Lipase‐Catalyzed Concentration of Stearidonic Acid in Modified Soybean Oil by Partial Hydrolysis

Kleiner

Vázquez

Akoh

2012

J Americ Oil Chem Soc

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Stearidonic acid (SDA, 18:4 ω‐3) content of modified soybean oil (MSO) containing ~25 % SDA, was increased by lipase‐catalyzed hydrolysis. Four non‐immobilized powdered lipases, Lipase AY 30 (Candida rugosa), Lipase G 50 (Penicillium camembertii), Lipomod™ 34P‐L034P (Candida cylindracea [rugosa]), Lipomod™ 36P‐L036P (Rhizopus oryzae), and an immobilized lipase, Lipozyme RM IM (Rhizomucor miehei) were assessed, at various incubation times, for their ability to hydrolyze MSO and specificity toward SDA. The SDA enriched products contained triacylglycerols (TAG), diacylglycerols (DAG) and monoacylglycerols (MAG). Lipase 34P‐L034P exhibited specificity towards SDA, while Lipase AY was able to discriminate against it. The highest total SDA content (40.9 mol%) was obtained with Amano AY lipase at 4 h incubation (66.2 % hydrolysis). Unhydrolyzed TAG, 1,3‐DAG, 2,3(1)‐DAG, and MAG contained 37.7 (56.4 at the sn‐2 position), 41.6, 51.5 (54.9 at the sn‐2 position), and 49.9 % SDA, respectively. Amano AY lipase was also used to hydrolyze previously SDA‐enriched TAG (48.7 % SDA) obtained from low temperature crystallization of MSO. The highest total SDA content (62.7 mol%) was obtained at 12 h incubation (85.9 % hydrolysis). The SDA contents of unhydrolyzed TAG, 1,3‐DAG, 2,3(1)‐DAG, and MAG were 58.7 (65.7 at the sn‐2 position), 71.2, 70.2 (52.9 at the sn‐2 position), and 59.4 %, respectively.

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“…The average and standard deviation of triplicate analyses are reported. The fatty acid profiles of MSO and LTC-TAG were in agreement with those reported previously [11,15].…”

Section: Pancreatic Lipase-catalyzed Sn-2 Positional Analysissupporting

confidence: 91%

Section: Introductionmentioning

confidence: 98%

Lipase‐Catalyzed Concentration of Stearidonic Acid in Modified Soybean Oil by Partial Hydrolysis

Kleiner

Vázquez

Akoh

2012

J Americ Oil Chem Soc

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“…Unlike the industrial process for the preparation of n ‐3 FA‐rich SLs, recent studies employed lipase‐catalyzed direct esterification, interesterification, or acidolysis for the preparation of n ‐3 FA‐rich SLs (Table ). The researchers prepared the SLs from α‐linolenic acid‐rich plant oils, such as perilla and linseed oils (Mitra and others ; Farfan and others ; Yang and others ), stearidonic acid‐rich plant oils (Bilgic and Yesilcubuk ; Kleiner and others ) such as high‐stearidonic soybean and echium oils, and fish oils, such as from tuna and sardines (de Araujo and others ; Nagao and others ; Sengupta and Ghosh ; Bispo and others ) or their free FA fractions using Lipozyme RM IM, Lipozyme TL IM, or Novozym 435. The table also shows that some researchers have produced conjugated FA‐rich SLs using conjugated linoleic acid ethyl esters or free FAs obtained from bitter gourd seed oil, which is rich in conjugated linolenic acid, as the substrates (Elibal and others ; Yang and others ).…”

Section: Health‐beneficial Fa‐rich Fats /Oilsmentioning

confidence: 99%

Recent Research Trends on the Enzymatic Synthesis of Structured Lipids

Kim

Akoh

2015

Journal of Food Science

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136

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Structured lipids (SLs) are lipids that have been chemically or enzymatically modified from their natural biosynthetic form. Because SLs are made to possess desired nutritional, physicochemical, or textural properties for various applications in the food industry, many research activities have been aimed at their commercialization. The production of SLs by enzymatic procedures has a great potential in the future market because of the specificity of lipases and phospholipases used as the biocatalysts. The aim of this review is to provide concise information on the recent research trends on the enzymatic synthesis of SLs of commercial interest, such as medium- and long-chain triacylglycerols, human milk fat substitutes, cocoa butter equivalents, trans-free or low-trans plastic fats (such as margarines and shortenings), low-calorie fats/oils, health-beneficial fatty acid-rich fats/oils, mono- or diacylglycerols, and structurally modified phospholipids. This limited review covers 108 research articles published between 2010 and 2014 which were searched in Web of Science.

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“…In the study by Kleiner et al, (2012), firstly, low temperature crystallization (LTC) was applied in order to increase SDA content in modified soybean oil from 25% to 48.72% (TAG) and 60.78% (FFA). In the next step, SL with the highest SDA content (53.46 ± 1.85% SDA with 36.37 ± 3.14% at sn-2 position) was produced via the acidolysis reaction between the TAG and FFA of LTC catalyzed by Lipozyme ® TL IM in solvent free conditions.…”

Section: Introductionmentioning

confidence: 99%

“…As a result of the study, SLs were produced with 4.9% SDA and 43% PUFA contents. To sum up, previous studies used SDA rich oil sources or Echium oil to enrich oils in terms of omega-3 and omega-6 PUFAs (Bilgiç and Yeşilçucuk, 2012;Kleiner et al, 2012;Gökçe, Sahin-Yeşilçubuk and Üstün, 2013;Ifeduba and Akoh, 2014). However, no previous study investigated the influence of reaction conditions for obtaining MLM-type SL from Echium oil fatty acids and tricaprylin.…”

Section: Introductionmentioning

confidence: 99%

Use of <em>Echium</em> oil fatty acids and tricaprylin as substrates of enzymatic interesterification for the production of structured lipids

Yüksel

Şahin‐Yeşilçubuk

2018

Grasas y Aceites

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SUMMARY:Structured lipids (SLs) were produced from the free fatty acids of Echium oil and tricaprylin by enzymatic acidolysis reactions. Lipozyme ® RM IM, immobilized sn-1,3 specific lipase was used in the enzymatic reactions. In order to optimize the incorporation of stearidonic acid (SDA), three factors were chosen , reaction time (6-12 hour) and substrate molar ratio (3-6 mol/mol (total free fatty acids/ tricaprylin)] for the application of response surface methodology (RSM) using a central composite circumscribed design (CCC) with five levels. The optimum temperature, time and substrate molar ratio obtained from the models were 60 ºC; 6 h, 6 mol/mol, respectively. Furthermore, SLs with 6.2% SDA content at sn-2 position were produced by scaling up the process. SL was obtained with nearly 78-79% of long-chain fatty acids at the sn-2 position. According to the melting profile analysis, the melting peaks of tricaprylin and Echium oil were sharper and narrower while the SL had more broadened peaks. KEYWORDS: Echium oil; Enzymatic acidolysis; Lipozyme® RM IM; Response surface methodology; Stearidonic acid; Tricaprylin RESUMEN: Uso de ácidos grasos de aceite de Echium y tricaprilina como sustratos de interesterificación enzimática para la producción de lípidos estructurados. Se produjeron lípidos estructurados (SL) a partir de ácidos grasos libres de aceite de Echium y tricaprilina mediante reacciones de acidolisis enzimática. Se usó Lipozyme ® RM IM, lipasa inmovilizada específica de sn-1,3 en las reacciones enzimáticas. Para optimizar la incorporación de ácido estearidónico (SDA), se eligieron tres factores [Temperatura de reacción (50-60 ºC), tiempo de reacción (6-12 horas) y proporción molar del sustrato (3-6 mol/mol (total de ácidos grasos libres) / tricaprylin)] para la aplicación de la metodología de superficie de respuesta (RSM) mediante el uso de un diseño compuesto central circunscrito (CCC) con cinco niveles. La relación óptima de temperatura, tiempo y sustrato obtenida de los modelos fue 60 ºC; 6 h, 6 mol/mol. Además, se produjeron SL con un contenido de SDA del 6,2% en la posición sn-2 mediante el proceso de escalamiento, SL se obtuvo con casi 78-79% de ácidos grasos de cadena larga en la posición sn-2. Según el análisis del perfil de fusión, los picos de fusión de la tricaprilina y el aceite de Echium fueron más agudos y estrechos, mientras que los SL tuvieron picos más amplios.

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Increasing Stearidonic Acid (SDA) in Modified Soybean Oil by Lipase‐Mediated Acidolysis

Cited by 4 publications

References 28 publications

Lipase‐Catalyzed Concentration of Stearidonic Acid in Modified Soybean Oil by Partial Hydrolysis

Lipase‐Catalyzed Concentration of Stearidonic Acid in Modified Soybean Oil by Partial Hydrolysis

Recent Research Trends on the Enzymatic Synthesis of Structured Lipids

Use of <em>Echium</em> oil fatty acids and tricaprylin as substrates of enzymatic interesterification for the production of structured lipids

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