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WO2008133573A1 - Huile marine enrichie en acide gras polyinsaturé (pufa), comprenant l'acide eicosapentaénoïque (epa) et l'acide docosahexaénoïque (dha) et son procédé de fabrication - Google Patents

Huile marine enrichie en acide gras polyinsaturé (pufa), comprenant l'acide eicosapentaénoïque (epa) et l'acide docosahexaénoïque (dha) et son procédé de fabrication Download PDF

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Publication number
WO2008133573A1
WO2008133573A1 PCT/SE2008/000290 SE2008000290W WO2008133573A1 WO 2008133573 A1 WO2008133573 A1 WO 2008133573A1 SE 2008000290 W SE2008000290 W SE 2008000290W WO 2008133573 A1 WO2008133573 A1 WO 2008133573A1
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WIPO (PCT)
Prior art keywords
mol
acid
oil
dha
epa
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Application number
PCT/SE2008/000290
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English (en)
Inventor
Patrick Adlercreutz
Ann-Marie Lyberg
Original Assignee
Patrick Adlercreutz
Ann-Marie Lyberg
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Patrick Adlercreutz, Ann-Marie Lyberg filed Critical Patrick Adlercreutz
Priority to EP08741864A priority Critical patent/EP2147088A4/fr
Priority to CA002685272A priority patent/CA2685272A1/fr
Publication of WO2008133573A1 publication Critical patent/WO2008133573A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols

Definitions

  • a polyunsaturated fatty acid (PUFA) enriched marine oil comprising eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) , and a process of production thereof
  • PUFA polyunsaturated fatty acid
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • the invention relates to a PUFA enriched marine oil being substantially free from heavy metals, PCB and dioxins comprising at least 40 mol % eicosapentaenoic acid and docosahexaenoic acid and at least 50 mol % of mono and diglycerides as well as a method to produce such a PUFA enriched marine oil.
  • n-3 fatty acids have well documented positive health effects.
  • the most important fatty acids in this group are eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • the dominating source of these fatty acids is various kinds of marine oils. Large efforts have been made to enrich EPA and DFIA from marine oils to obtain more concentrated products for use as food supplements or food ingredients. Most commonly the EPA and DHA containing triglycerides from the marine oil are hydrolysed to free fatty acids, followed by fractionation of the fatty acids using urea as complexation agent.
  • lipases More recently, the fatty acid specificity of lipases has been utilised to enrich EPA and/or DHA from marine oils. Most lipases have an ability to discriminate against the n-3 fatty acids and especially docosahexaenoic acid (DHA). Therefore lipases are utilised for enrichment of DHA and eicosapentaenoic acid (EPA) in marine oils, in free fatty acids or in simple esters of fatty acids. Furthermore, the lipases are able to operate at mild conditions, which is preferable since EPA and DHA are prone to oxidation. The choice of lipase and raw material depends on the desired lipid structure and ratio of EPA and DHA in the final product.
  • DHA docosahexaenoic acid
  • EPA eicosapentaenoic acid
  • the fatty acid specificity of the lipase should also be considered. If the fatty acids are located in triglycerides, the regiospecificity and triglyceride specificity also have an effect on the enrichment. Thus the positional distribution of the fatty acids and the glyceride molecule structure may have an impact on the ability of the lipase to enrich DHA and/or EPA in either the substrate or product and a product containing DHA and EPA as mono and di-glycerides will give rise to additional health benefits as well as emulsifying properties.
  • EPA and/or DHA of marine origin have been concentrated by different strategies using lipases. Most lipases discriminate against DHA more than against EPA such as Candida rugosa (formerly Candida cylindraced) and Rhizomucor miehei (Mukherjee et al. 1993). Nevertheless, there are lipases that discriminate against EPA more than against DHA such as porcine pancreas, Chromobacterium viscosum, Pseudomonas sp., Pseudomonas cepacia and Pseudomonas fluorescens (Breivik et al. 1997, Halldorsson et al. 2004, Mukherjee et al. 1993).
  • the lipase from Rhizomucor miehei was utilised for enrichment of DHA in free fatty acid from fish oil by esterification of the oil with butanol or glycerol (Halldorsson et al. 2003, Hills et al. 1990).
  • Another approach for concentrating both DHA and EPA in the free fatty acids was to esterify free fatty acids from marine origin with glycerol catalysed by one of the lipases from Pseudomonas sp., Pseudomonas fluoresceins, Thermomyces lanuginosus (formerly Humicula lanuginosa) or Rhizopus oryzae (Haraldsson et al. 2000).
  • Enrichment of both DHA and EPA in the glyceride fraction was obtained by ethanolysis or hydrolysis of fish oil catalysed by the lipase from Pseudomonas sp., Pseudomonas fluorescens, Geotrichum candidum (Breivik and Haraldsson 1995, Breivik et al. 1997, Haraldsson et al. 1997).
  • US 5945318 disclose a method in which a number of different lipases have been evaluated. Many of the lipases showed a low or no selectivity between different fatty acids. None of the lipases was immobilized.
  • EPA and DHA in the final product are ethyl esters and not mono-and di-glycerides. Examples of such method are disclosed in WO 2004043894 and Liang et al., 2000).
  • EPA and DHA containing products available for use as food supplements and food ingredients have the fatty acids as free fatty acids, simple esters (methyl or ethyl), as triglycerides and recently also as phospholipids. Most products contain more EPA than DHA.
  • the product of the present invention contains EPA and DHA mainly as di- and mono-glycerides, with additional health benefits as well as emulsifying properties, useful for some applications. Furthermore the product of the present invention contains more DHA than EPA, thus strengthening the specific health benefits of DHA. In this product, the positive effects of DHA and diglycerides are thus combined in a new way.
  • the invention relates to a PUFA enriched marine oil being substantially free from heavy metals, PCB and dioxins comprising at least 40 mol % eicosapentaenoic acid and docosahexaenoic acid and at least 50 mol % of mono and diglycerides.
  • an improved oil is available providing EPA and DHA mainly as di- and mono-glycerides, with additional health benefits as well as emulsifying properties. Furthermore the product of the present invention contains more DHA than EPA, thus strengthening the specific health benefits of DHA.
  • the invention also relates to a method of treating a marine oil having an eicosapentaenoic acid and docosahexaenoic acid content of at least 25 mol % comprising the steps of; providing an immobilised lipase, transesterifying said oil with a C1-C6 alcohol in the presence of said immobilised lipase and obtaining a product with EPA and DHA enriched in the glyceride fraction and a large part of the other fatty acid being in the form of esters of the alcohol used or as free fatty acids, removal of simple fatty acid esters and free fatty acids by distillation and obtaining a PUFA enriched marine oil being substantially free from heavy metals, PCB and dioxins comprising at least 40 mol % eicosapentaenoic acid and docosahexaenoic acid and at least 50 mol % of mono and diglycerides.
  • FIG 1 shows Mol% DHA in the glyceride fraction (TG + DG + MG) against loss of DHA from this fraction during ethanolysis of squid oil catalysed by RM, TL, PC and PF.
  • FIG 2 shows the reaction profile for the lipase from Thermomyces lanuginosus.
  • FIG 3 shows Mol% EPA in the glyceride fraction (TG + DG + MG) against loss of EPA from this fraction during ethanolysis of squid oil catalysed by RM, TL, PC and PF.
  • emulsifying properties is intended to mean that emulsions can be formed easily when oil and water are vigorously mixed.
  • fatty acid compositions are expressed using the term "mol %".
  • One mol % of fatty acid X means that 1 % of the fatty acid residues in that fraction is fatty acid X.
  • mol % Contents of different lipid classes (triglycerides, diglycerides, monoglycerides, free fatty acids and fatty acid ethyl esters) are expressed as mol %.
  • One mol % diglycerides means that the number of moles of diglycerides constitutes 1 % of the total number of moles of the different lipid classes.
  • the term "substantially free from” is intended to mean that the analysed values of contaminants are far below the limits set by the EU Commission according to heavy metals, PCB:s and dioxins in fish oil. ( ⁇ 0.1 ppm of each one of the elements: arsenic, cadmium, mercury and lead.)
  • PUFA polyunsaturated fatty acids
  • DHA docosahexaenoic acid
  • EPA eicosapentaenoic acid
  • OIL EXTRACT The invention relates to an improved PUFA enriched marine oil being substantially free from heavy metals, PCB and dioxins comprising at least 40 mol % eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and at least 50 mol % of mono and diglycerides.
  • Said invented marine oil having improved properties such as having emulsifying properties which enables the possibility to form emulsions with water rich components to form dressings, sauces, desserts, doughs, dairy drinks, fruit and vegetable based drinks and many other kinds of food.
  • the content of eicosapentaenoic acid and docosahexaenoic acid in the oil extract may be at least or equal to 40 mol % and the content of the mono and diglycerides at least or equal to 60 mol %.
  • Other examples are at least 45 mol % EPA + DHA and at least 55 mol % mono and diglycerides or 50 mol % EPA + DHA and 50 % mono and diglycerides.
  • the ratio between eicosapentaenoic acid and docosahexaenoic acid may be lower than 1 and the molar ratio between mono and diglycerides may be lower than 1.
  • the content of the mono and diglycerides mat be at least 50, 60, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75 ,76, 77, 78, 79, 80 mol %or even higher.
  • the content of the triglycerides may be from about 5 to about 30 %, such as 5-25, 5-20, 5-15 mol %. Specific examples are 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30 mol %.
  • the oil extract may be obtained from any suitable marine oil source such as be selected from the group consisting of different kinds of fish, algae, crustaceans and for example one suitable source is squid.
  • the invention relates to a method of treating a marine oil having an eicosapentaenoic acid and docosahexaenoic acid content of at least 25 % comprising the steps of; providing an immobilised lipase or a mixture of lipases, transesterifying said oil with a C1-C6 alcohol in the presence of said immobilised lipase and obtaining a product in which EPA and DHA are enriched in the glyceride fraction and a large part of the other fatty acids are present as esters of the alcohol used or as free fatty acids.
  • a PUFA-enriched marine oil substantially free from heavy metals, PCB and dioxins comprising at least 40 mol % eicosapentaenoic acid and docosahexaenoic acid and an at least 50 mol % of mono and diglycerides.
  • Immobilisation of the lipase or lipases provides several advantages such as higher activity and stability of the lipases.
  • Suitable support materials are porous inorganic or organic materials, with silica and polypropylene as a couple of examples.
  • Some immobilised lipases are commercially available, such as Lipozym RM IM from Novozymes, Denmark.
  • lipases examples include those from Thermomyces lanuginosus, Pseudomonas cepacia, Pseudomonas fluorescens and Rhizomucor miehei.
  • One suitable lipase being the one from Thermomyces lanuginosus, which can be obtained from Novozymes, Denmark or Sigma-Aldrich, St Louis, MO, USA.
  • the transesterification step may be done with an alcohol or a mixture of alcohols such as methanol, ethanol, propanol, butanol, pentanol or hexanol. During the transesterification it is of importance to protect the unsaturated fatty acids from oxidation. This may be done by carrying out the reaction under nitrogen.
  • the concentration of the marine oil extract may be done by distillation in one or several distillation steps, whereby the relatively volatile fatty acid esters and free fatty acids can be removed from the less volatile residual glyceride mixture. In the distillation step potential volatile contaminants such as PCB and dioxins are efficiently removed from the glyceride mixture.
  • the distillation is preferably carried out at low temperature and pressure.
  • the invented process is especially adapted to the preparation of marine oil extracts as defined above having a specific combination and amount of mono- and diglycerides as well as EPA and DHA having healthy effects on the mammal, such as a human being.
  • Examples are intended to illustrate, but not to limit, the invention in any manner, shape, or form, either explicitly or implicitly.
  • Tridecanoic acid albumin from bovine serum and non-immobilised lipases from Rhizomucor miehei (RM), Thermomyces lanuginosus (TL), Pseudomonas cepacia (Amano lipase PS)(PC) and Pseudomonas fluorescens (Amano lipase)(PF) were bought from Sigma (St Louis, MO, USA). The squid oil was deodorized. Accurel MPlOOO, a polypropylene support for immobilisation, was obtained from Akzo (Obernburg, Germany).
  • the lipases were immobilised on the polypropylene support MPlOOO by adsorption.
  • the amount of lipase added during the immobilisation corresponded to a 40 mg protein/g support.
  • the lipase was dissolved in 20 mM sodium phosphate buffer (pH 6). The solution was centrifuged and the supernatant was added to the MPlOOO, which was prewetted with ethanol (3 ml/g preparation). The mixture containing both enzyme and support was shaken overnight at room temperature. Then the enzyme preparation was filtered and washed with sodium phosphate buffer (20 mM, pH 6). To the enzyme preparation 1 ml sodium phosphate buffer (200 mM, pH I)Ig preparation was added and this preparation was dried under reduced pressure overnight.
  • the protein loading of the lipase preparations was determined to 22 mg protein/g support for Rhizomucor miehei, 33 mg protein/g support for Thermomyces lanuginosus, 19 mg protein/g support for Pseudomonas cepacia and 6 mg protein/g support for Pseudomonas fluorescens.
  • TG Triglycerides
  • DG diglycerides
  • MG monoglycerides
  • FFA free fatty acids
  • the TLC plate was sprayed with 0.1% 2,7-dichlorofluorescein in ethanol.
  • the bands of TG (start samples only), DG, MG and FFA were scraped off and placed in glass tubes for fatty acid analysis.
  • Triglycerides, diglycerides and monoglycerides were separately methylated using sodium methoxide as reagent. Methylation of free fatty acids was carried out using sulphuric acid as catalyst. Ethyl esters from the TLC plates were extracted in cyclohexane. Fatty acids in the form of either methyl esters or ethyl esters were analysed using gas chromatography.
  • the response factors of the different fatty acid methyl esters were obtained from analysis of a standard mixture. These response factors were used to calculate the relative amounts of different fatty acids within a sample based on mol%. These data were compared with the internal standard (methyl tridecanoate) to determine the absolute amount ( ⁇ mol) of the fatty acids in the sample. Results
  • Ethanolysis of squid oil was catalysed by lipases from Rhizomucor miehei (RM), Thermomyces lanuginosus (TL), Pseudomonas cepacia (PC) and Pseudomonas fluoresceins (PF) in order to compare their ability to discriminate against EPA and DHA.
  • RM Rhizomucor miehei
  • TL Thermomyces lanuginosus
  • PC Pseudomonas cepacia
  • PF Pseudomonas fluoresceins
  • Fig. 1 shows the enrichment of DHA against the DHA loss for four lipases.
  • the lipase that obtained the highest DHA recovery during the enrichment of DHA was that from Thermomyces lanuginosus. After 24 hours of reaction the glyceride fraction contained 37 mol%, and 1.7 mol% of DHA was lost. An even higher enrichment after 24 hours of reaction was provided by the lipase from Rhizomucor miehei. However, this lipase also showed a considerable DHA loss (6.8 mol%). The lipase from Thermomyces lanuginosus was therefore considered the most suitable lipase for enrichment of DHA in the squid oil.
  • the reaction profile provided by the lipase from Thermomyces lanuginosus is shown in Fig. 2.
  • the triglycerides were converted to diglyceride at a high rate.
  • No DHA ethyl esters were formed during the first 1.5 hours.
  • the lipase from Thermomyces lanuginosus was chosen to catalyse ethanolysis in a larger scale.
  • Squid oil (500 g), ethanol (108 ml) and immobilised lipase from Thermomyces lanuginosus (13.9 g) were stirred with continuous nitrogen addition for 24 hours.
  • the DHA and EPA content of the glyceride fraction had reached 35 and 17 mol%, respectively.
  • the recovery of DHA was 97 mol% and the recovery of EPA was 79 mol%.
  • the dominating glyceride fraction was the diglycerides (Table T).
  • the reaction was stopped by filtering off the enzyme after which the ethanol was evaporated.
  • the ethyl esters were separated from the glyceride fraction after ethanolysis by using short path distillation (KD4, UIC GmbH, Alzenau-H ⁇ rstein, Germany). The distillation was first performed at 120 0 C, and the remaining part was distilled once more at 130°C. After the first distillation the distillate contained 167.6 g and the remainder 270.3 g. After the second distillation the distillate contained 6.1 g and the remainder (the final product) contained 243.1 g.
  • the reaction as well as the purification step was repeated and the result was a lipid composition in which there were at least 40 mo% EPA and DPA as well as at least 50 mol% of mono- and di-glycerides.

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
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  • Fats And Perfumes (AREA)

Abstract

L'invention porte sur une huile marine enrichie en PUFA qui est sensiblement exempte de métaux lourds, PCB et dioxines, comprenant au moins 40 % en moles d'acide eicosapentaénoïque et d'acide docosahexaénoïque sous la forme telle qu'au moins 50 % en moles de mono- et diglycérides, ainsi que sur un procédé de fabrication d'une telle huile marine enrichie en PUFA.
PCT/SE2008/000290 2007-04-26 2008-04-25 Huile marine enrichie en acide gras polyinsaturé (pufa), comprenant l'acide eicosapentaénoïque (epa) et l'acide docosahexaénoïque (dha) et son procédé de fabrication WO2008133573A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP08741864A EP2147088A4 (fr) 2007-04-26 2008-04-25 Huile marine enrichie en acide gras polyinsaturé (pufa), comprenant l'acide eicosapentaénoïque (epa) et l'acide docosahexaénoïque (dha) et son procédé de fabrication
CA002685272A CA2685272A1 (fr) 2007-04-26 2008-04-25 Huile marine enrichie en acide gras polyinsature (pufa), comprenant l'acide eicosapentaenoique (epa) et l'acide docosahexaenoique (dha) et son procede de fabrication

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SE0701001 2007-04-26
SE0701001-0 2007-04-26

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WO2008133573A1 true WO2008133573A1 (fr) 2008-11-06

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CA (1) CA2685272A1 (fr)
WO (1) WO2008133573A1 (fr)

Cited By (17)

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WO2010010365A1 (fr) * 2008-07-24 2010-01-28 Pharma Marine As Acides gras polyinsaturés pour améliorer la vision
WO2010010364A2 (fr) * 2008-07-24 2010-01-28 Pharma Marine As Procédé de purification d’huiles
CN101736044A (zh) * 2008-11-18 2010-06-16 浙江海洋学院 一种连续化酶促合成n-3PUFA甘油酯的方法
WO2012160442A1 (fr) * 2011-05-20 2012-11-29 Pharma Marine As Procédé pour améliorer les oméga-3 et éliminer les contaminants volatils simultanément
WO2013007315A1 (fr) 2011-07-14 2013-01-17 Soluciones Extractivas Alimentarias, S.L. Nouveau procédé de réduction des polluants dans les graisses et les huiles et leurs dérivés
US20130196393A1 (en) * 2010-06-25 2013-08-01 Epax As Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids
US9050309B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
JPWO2013172346A1 (ja) * 2012-05-14 2016-01-12 日本水産株式会社 環境汚染物質を低減させた高度不飽和脂肪酸又は高度不飽和脂肪酸エチルエステル及びその製造方法
JP2016502573A (ja) * 2012-11-02 2016-01-28 プロノヴァ・バイオファーマ・ノルゲ・アーエスＰｒｏｎｏｖａ ＢｉｏＰｈａｒｍａ Ｎｏｒｇｅ ＡＳ 油組成物からの好ましくない成分の除去
US9492545B2 (en) 2012-05-07 2016-11-15 Omthera Pharmaceuticals Inc. Compositions of statins and omega-3 fatty acids
WO2016207734A1 (fr) * 2015-06-26 2016-12-29 Pronova Biopharma Norge As Composition pour le traitement de la nafld
KR20170018825A (ko) * 2014-06-06 2017-02-20 마린 인그리디언츠, 엘엘씨 오메가-3 조성물, 제형 및 사용 방법
ITUB20153877A1 (it) * 2015-09-24 2017-03-24 Tiberio Bruzzese Metodo di purificazione di gliceridi di acidi grassi, composizioni che ne derivano, e loro uso
EP3165591A4 (fr) * 2014-07-02 2017-11-29 Nippon Suisan Kaisha, Ltd. Procédé de fabrication d'acides gras libres insaturés monovalents dérivés d'un produit de la mer ou de leurs esters d'alcool de basse qualité
CN111172211A (zh) * 2020-03-20 2020-05-19 江南大学 一种酶法制备富含鱼油n-3长链多不饱和脂肪酸甘油酯的方法及其产品
CN111172210A (zh) * 2020-03-20 2020-05-19 江南大学 一种两步酶法制备富含花生四烯酸甘油酯的方法及其产品
WO2022211017A1 (fr) * 2021-04-01 2022-10-06 花王株式会社 Composition d'huile/matière grasse

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Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010010365A1 (fr) * 2008-07-24 2010-01-28 Pharma Marine As Acides gras polyinsaturés pour améliorer la vision
WO2010010364A2 (fr) * 2008-07-24 2010-01-28 Pharma Marine As Procédé de purification d’huiles
WO2010010364A3 (fr) * 2008-07-24 2010-03-25 Pharma Marine As Procédé de purification d’huiles
CN101736044A (zh) * 2008-11-18 2010-06-16 浙江海洋学院 一种连续化酶促合成n-3PUFA甘油酯的方法
US20130196393A1 (en) * 2010-06-25 2013-08-01 Epax As Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids
US9476008B2 (en) 2010-06-25 2016-10-25 Epax As Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids
WO2012160442A1 (fr) * 2011-05-20 2012-11-29 Pharma Marine As Procédé pour améliorer les oméga-3 et éliminer les contaminants volatils simultanément
WO2013007315A1 (fr) 2011-07-14 2013-01-17 Soluciones Extractivas Alimentarias, S.L. Nouveau procédé de réduction des polluants dans les graisses et les huiles et leurs dérivés
US9050308B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US9050309B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US10117844B2 (en) 2012-01-06 2018-11-06 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US9492545B2 (en) 2012-05-07 2016-11-15 Omthera Pharmaceuticals Inc. Compositions of statins and omega-3 fatty acids
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