Enzymatic modification of evening primrose oil: Incorporation of n−3 polyunsaturated fatty acids

Akoh, Casimir C.; Jennings, Brenda H.; Lillard, D. A.

doi:10.1007/bf02523416

Cited by 54 publications

(31 citation statements)

References 16 publications

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“…In present study, the incorporation of ALA into olive oil increased by increasing the molar ratio of ALA: olive oil. Other investigators have also reported that the incorporation of n-3 fatty acid into seed oil raises by increasing the substrate molar ratio [11,22]. Also, it has been stated that incorporation rate can be improved by choosing high substrate molar ratios while reducing the reaction time, but Jennings and Akoh [27] have pointed out a significant modification in large scale, using excess amounts of n-3 fatty acid had resulted in lipase inhibition and decreased in product yield while removing excess fatty acids.…”

Section: Effect Of Ratio Of Ala: Olive Oil For Enrichment Of Olivementioning

confidence: 93%

“…Recently, many efforts have been carried out in transesterification or inter-esterification reactions to Transesterification Reaction: A small scale modify and enrich the content of n-3 PUFA in vegetable transesterification reaction was conducted in 50 ml oil, melonseed oil, borage oil and evening primrose oil round bottom capped flask. According to author with implementation of biocatalysts such as lipases previous work [13], -linolenic acid (ALA) which is used [11,12].…”

Section: Introductionmentioning

confidence: 99%

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Enrichment of Olive Oil with Alpha Linolenic Acid Catalyzed by Lipase Mediated Trans-Esterification

Rupani

Gadre²,

Kodam³

et al. 2014

IJEE

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Consumption of Polyunsaturated fatty acid omega-3 is the most recommended fatty acids which have a health benefits for brain, kidney and eye. The conversion of plant-derived omega-3 (n-3) -linolenic acid (ALA, 18:3n-3) to long-chain eicosapentaenoic acid (EPA, 20:5n-3) and docosahexaenoic acid (DHA, can enhance ALA sufficient diets in compare to ALA deficient diets. Alpha-linolenic acid (ALA) was extracted and enriched from flax seed oil. Commercial lipases Candida rugosa, Pseudomonas cepacea and P. fluorescens were used for transesterification of ALA enriched from flax seed oil into olive oil TAG back bone. Gas chromatography of olive oil showed it contained high amounts of oleic acid (C18:1, n-9), linoleic acid (C18:2, n-6) and palmitic acid (C18:0) with 0% of ALA. Among the commercial lipase C. rugosa has more preference to ALA and 27% of ALA was incorporated to TAG back bone of olive oil. In 24 hours reaction time, the ALA concentration in TAG of olive has increased to 26% while oleic acid decreased to 60% and palmitic acid decreased from 25 to 7%. The highest incorporation of ALA into olive oil (29%) occurred for ALA: olive oil mole ratio (1:2). There was a decline in incorporation of ALA in olive oil backbone with an increase in the amount of water. ALA incorporation of 25% occurred with 100 µl water while without water it was 27%; it decreased to 15% with 1 ml of water.

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Section: Effect Of Ratio Of Ala: Olive Oil For Enrichment Of Olivementioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Enrichment of Olive Oil with Alpha Linolenic Acid Catalyzed by Lipase Mediated Trans-Esterification

Rupani

Gadre²,

Kodam³

et al. 2014

IJEE

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“…Akoh e colaboradores 55 descreveram a reação de transesterificação entre óleo de prímula (ácido γ-linolênico) e éster etílico de EPA como doadores de grupo acil, catalisada por lipase imobilizada de Candida antarctica. A incorporação de EPA foi de 34%, enquanto os níveis de ácido γ-linolênico não sofreram mudanças significativas, o que resultou em uma modificação favorável na taxa de ω3/ω6 de 0,01 para 0,60 após reação de transesterificação.…”

Section: Interesterificaçãounclassified

Aplicação de lipases microbianas na obtenção de concentrados de ácidos graxos poliinsaturados

Carvalho¹,

Campos²,

Noffs³

et al. 2003

Quím. Nova

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Recebido em 7/12/01; aceito em 11/7/02 APPLICATION OF MICROBIAL LIPASES TO CONCENTRATE POLYUNSATURATED FATTY ACIDS. Several polyunsaturated fatty acids (PUFA) belonging to the ômega 6 series, such as cis-6,9,12 γ-linolenic acid, as well as those of the ômega 3 series, such as cis -5,8,11,14,17-eicosapentaenoic acid and cis-4,7,10,13,16,19-docosahexaenoic acid are of considerable interest due to their nutritional and therapeutic properties. Methods used for the concentration of PUFA from natural sources include urea adduct formation, solvent winterization, supercritical fluid extraction and lipase-catalyzed reaction. Lipases are known to have little reactivity on PUFA and these acids can be enriched by selective hydrolysis, direct esterification of glycerol with PUFA and interesterification. Since lipase reactions are advantageous with respect to fatty acid, positional specificities and mild incubation condition, these enzymes are considered to be suitable for the production of PUFA concentrates for medical purposes.Keywords: polyunsaturated fatty acid; lipase; fatty acid selectivity. INTRODUÇÃOA importância dos ácidos graxos essenciais (ácido linoléico e ácido α-linolênico) na dieta humana foi assunto de grande interesse nas décadas passadas. Estes ácidos que contém duas ou mais insaturações são chamados poliinsaturados e representados por sím-bolos numéricos, como C18:2 (9,12) que representa o ácido linoléico e o C18:3 (9,12,15), o ácido α-linolênico, sendo que o número justaposto ao símbolo C indica o número de átomos de carbono e o segundo número, a quantidade de duplas ligações. A posição da ligação dupla na cadeia hidrocarbonada é indicada entre parênteses, pela identificação do átomo de carbono mais próximo da carboxila implicado na respectiva insaturação. Os ácidos graxos também podem ser divididos em famílias ou séries, dependendo da localização da última ligação dupla em relação ao seu grupamento metílico terminal: família ômega-6 (ω6) representada pelo ácido linoléico e a família ômega-3 (ω3), pelo ácido α-linolênico.Esses dois tipos de ácidos graxos são chamados essenciais porque não podem ser sintetizados pelo organismo humano e devem ser fornecidos através da dieta. Após a ingestão, os ácidos graxos, uma vez absorvidos por células e tecidos, podem ser dessaturados e alongados a outros ácidos poliinsaturados de cadeia longa 1 . Os processos de alongação e dessaturação do ácidos linoléico e α-linolênico ocorrem nos animais e, vagarosamente, nos homens originando diversos metabólitos, como representado na Figura 1. Na atualidade, pesquisas têm enfatizado o importante papel dos metabólitos poliinsaturados, tais como ácido γ-linolênico (18:3 (6,9,12)) da família ω6, ácido eicosapentaenóico (20:5 (5,8,11,14,17)) e ácido docosaexaenóico (22:6 (4,7,10,13,16,19)) da família ω3, representados por EPA e DHA, respectivamente.Os diversos dos ácidos graxos poliinsaturados (AGPI) no metabolismo de lipoproteínas, síntese de eicosanóides e funcionamento das plaquetas e das paredes dos vasos, os tornam de especial i...

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“…It could be useful to use this oil as a model oil when incorporating long-chain EFA into MCT. Recently, the incorporation of n-3 PUFA, especially EPA and DHA, into melon seed oil (13), vegetable oils (14), borage oil (15)(16)(17)(18), evening primrose oil (18,19), and trilinolein (20) has been reported. Synthesis of SL containing MCFA in the sn-1,3 positions and an unsaturated LCFA in the sn-2 position of the glycerol backbone using 1,3-regiospecific lipases was recently reported by Soumanou et al (21).…”

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confidence: 99%

Lipase‐assisted acidolysis of high‐laurate canola oil with eicosapentaenoic acid

Hamam

Daun²,

Shahidi

2005

J Americ Oil Chem Soc

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The production of structured lipids via acidolysis of high-laurate canola oil (Laurical 15) with EPA in hexane was carried out using lipase from Pseudomonas sp. The optimal reaction conditions used 4% lipase, at a mole ratio of oil to EPA of 1:3 at 45°C over 36 h. The positional distribution of FA on the glycerol backbone of unmodified oil indicated that lauric acid was mainly located at the sn-1,3 positions. Stereospecific analysis of the oil modified with EPA showed that lauric acid remained mostly esterified to the sn-1,3 positions of the TAG molecules and that EPA was also primarily in the sn-1,3 positions of the TAG molecules. Thus, the resultant structured lipids may have optimal value for use in applications where quick energy release and EPA supplementation are required.Paper no. J11116 in JAOCS 82, 875-879 (December 2005).

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Enzymatic modification of evening primrose oil: Incorporation of n−3 polyunsaturated fatty acids

Cited by 54 publications

References 16 publications

Enrichment of Olive Oil with Alpha Linolenic Acid Catalyzed by Lipase Mediated Trans-Esterification

Enrichment of Olive Oil with Alpha Linolenic Acid Catalyzed by Lipase Mediated Trans-Esterification

Aplicação de lipases microbianas na obtenção de concentrados de ácidos graxos poliinsaturados

Lipase‐assisted acidolysis of high‐laurate canola oil with eicosapentaenoic acid

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