[go: up one dir, main page]

WO1998018952A1 - Procede de production de matieres grasses contenant des acides gras hautement insatures contenant eux-memes un acide docosahexaenoique a concentration selective - Google Patents

Procede de production de matieres grasses contenant des acides gras hautement insatures contenant eux-memes un acide docosahexaenoique a concentration selective Download PDF

Info

Publication number
WO1998018952A1
WO1998018952A1 PCT/JP1997/003949 JP9703949W WO9818952A1 WO 1998018952 A1 WO1998018952 A1 WO 1998018952A1 JP 9703949 W JP9703949 W JP 9703949W WO 9818952 A1 WO9818952 A1 WO 9818952A1
Authority
WO
WIPO (PCT)
Prior art keywords
lipase
lipases
unsaturated fatty
highly unsaturated
dha
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP1997/003949
Other languages
English (en)
Japanese (ja)
Inventor
Yuji Okita
Yukie Imai
Nobuyoshi Shimizu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nissui Corp
Original Assignee
Nippon Suisan Kaisha Ltd
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.)
Filing date
Publication date
Application filed by Nippon Suisan Kaisha Ltd filed Critical Nippon Suisan Kaisha Ltd
Publication of WO1998018952A1 publication Critical patent/WO1998018952A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6409—Fatty acids
    • C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
    • C12P7/6434—Docosahexenoic acids [DHA]
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone

Definitions

  • the present invention relates to a method for producing a highly unsaturated fatty acid-containing oil or fat in which docosahexanoic acid is selectively concentrated.
  • polyunsaturated fatty acids are eicosapentaenoic acid (hereinafter abbreviated as “EPA”) and docosahexaenoic acid (hereinafter abbreviated as “DHA”).
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • Such rivases include Candi da Lugosa ( ⁇ .
  • An object of the present invention is to produce a highly unsaturated fatty acid-containing fat or oil having an increased ratio of DHA to EPA.
  • the present inventors have started to search for rivases that achieve both selective enrichment ability and high recovery rate with respect to the above-mentioned problems, and through experiments in which multiple types of lipases obtained from various biological species are combined to act on a substrate.
  • they have found that an increase in the DHA selective enrichment ability of a reaction system, which could not be achieved with a single lipase, can be achieved by using a specific combination of lipase groups, and thus completed the present invention.
  • the present invention provides a highly unsaturated fatty acid in which docosahexaenoic acid is selectively concentrated by performing a hydrolysis reaction of a polyunsaturated fatty acid-containing oil or fat with a lipase group having an enhanced ability to selectively concentrate docosahexaenoic acid. This is a method for producing fats and oils. / JP97 / 03949
  • Fatty acids other than PUFA in the constituent fatty acids of fish oils are hydrolyzed by lipase, which hardly or only slightly hydrolyzes the ester bond between PUFA and glycerin in the fatty acids of fish oil.
  • the ester bond between glycerin and glycerin is easily hydrolyzed, and PUFA is concentrated in the glyceride part.
  • the concentrated PUFA hydrolyzes EPA rather than DHA, and as a result, DHA is more concentrated in the glyceride than EPA.
  • the intrinsic properties of the rivase that is, the property of hardly or only slightly hydrolyzing the ester bond between PUFA and glycerin in the constituent fatty acids of fish oil are hardly affected.
  • the system exhibits a new property in that the added rivase hydrolyzes EPA in preference to DHA.
  • the lipase group that has enhanced the selective enrichment ability of docosahexaenoic acid is two or more lipases including one or more monodari lipase and / or diglyceride lipase and one or more other lipases.
  • the term “monoglyceride lipase and / or diglyceride driver” means a lipase which does not act on triglyceride but acts on diglyceride and monoglyceride to cause a hydrolysis reaction.
  • the present invention relates to a method for producing a highly unsaturated fatty acid-containing fat or oil using a monoglyceride lipase. And / or hydrolysis by two or more rivases, including one or more diglyceride lipases and one or more other lipases, to selectively concentrate docosahexanoic acid.
  • This is a method for producing saturated fatty acid-containing fats and oils.
  • the above monoglyceride lipase and / or diglyceride lipase is preferably derived from a microorganism (Penicilliun microorganism.
  • the present invention relates to a method for preparing a highly unsaturated fatty acid-containing fat or oil,
  • Penicillium By selectively conducting the hydrolysis reaction with two or more lipases including one or more of mono-glyceride lipase and Z or diglyceride rivase derived from microorganisms and one or more other lipases, docosahexane is selectively obtained. This is a method for producing fats and oils containing highly unsaturated fatty acids in which the acid is concentrated.
  • the above microorganism belonging to the genus Penicillium is used as a microorganism of the genus Penicillium.
  • the present invention relates to a highly unsaturated fatty acid-containing fat or oil, comprising: a monoglyceride drino derived from Penicllium camemberti. —Selective enrichment of docosahexaenoic acid by hydrolysis with two or more lipases, including at least one lipase and / or at least one diglyceride rivase This is a method for producing fats and oils containing highly unsaturated fatty acids.
  • lipases other than monoglyceride lipase and / or diglyceride lipase are known genus Candida (
  • Candida Candida
  • Mucor ⁇ Rhizopus ⁇
  • As ⁇ Noreginoles ⁇ (Aspergi 1 lus) x
  • Penicllium Pengull Acuobacterium (Achromobacter) Tric Geotrichum F Fusarium, Huraicuia, Serratia, Chromobacterium, and / Or lipase derived from microorganisms of Staphylococcus (Staphylococcus) microorganisms, which are described in "Enzymes in Food Processing" Third Edition p.206-208, ACADEMIC PRESS. , INC., Llarcourt Brace & Company ".
  • the present invention relates to a method for producing a polybutadiene containing polyunsaturated fatty acid
  • Penicillium By selectively performing a hydrolysis reaction with at least one of mono- and diglyceride rivases derived from microorganisms, and at least one lipase derived from microorganisms belonging to the genus listed above. This is a method for producing a highly unsaturated fatty acid-containing oil in which docosahexaenoic acid is concentrated.
  • a combination of two or more lipases, including one or more of the above-mentioned monoglyceride lipase and / or diglyceride lipase and one or more other lipases, is a combination of Penicillium and Candida or Penicillium. Rhium and Mucor II, or Nissiliium and Rhizops II.
  • the present invention relates to a method for producing a monoglyceride derived from a microorganism containing a polyunsaturated fatty acid, which is derived from microorganisms of Pseudomonas and Candida, Pseudomonas and Mucor, or Pseudomonas and Rhizopus. Hydrolysis by two or more lipases, including one or more lipases and / or one or more other lipases, selectively converts docosahexaenoic acid. Contains concentrated polyunsaturated fatty acids This is a method for producing an oil and fat.
  • PUFA such as arachidonic acid (C20: 4w6), EPA (C20: 5 ⁇ 3) and DHA (C22: 6w3). May be something. It is known that such fats and oils containing PUFA are produced by fish such as sardines and tuna, marine animals such as crustaceans, and certain microorganisms. For example, tuna oil is known to contain DHA in a large amount of 22.0%, compared to 14.6% of valmic acid and 17.2% of oleic acid.
  • the monoglyceride lipase and Z or diglyceride lipase used in the present invention have little or no action on triglyceride, and may be any that act on monoglyceride and / or diglyceride. Examples include those derived from Penicllium microorganisms. These lipases are all commercially available.
  • Penicllium camemberti is exemplified as a preferred example. It is also possible to use commercially available and easily available rivase derived from P. nigerium mannberti [trade name: Lipase 6, Amano Pharmaceutical Co., Ltd.].
  • the lipase used in the present invention which is used in combination with one or more of the above-mentioned monoglyceride lipase and Z or diglyceride lipase, includes Candida, Mucor, Rhizopus, Aspergillus, Pseudomonas; Panorama, Alcal igenes, Peniclium, Peniclium Terminology (Achromobacter), genus Geotrichum, Fusarium, Humicula, Serratia, Chromobacterium ), Lipases derived from Staphylococcus microorganisms, etc. These lipases can be appropriately selected from these known lipases according to the purpose.
  • Commercially available enzymes include lipase derived from Candida cylindrache [trade name: Lipase OF, Meito Sangyo Co., Ltd.], and Mucor My High.
  • Livase derived from (Mucor miehei) (trade name: Lipposim, Novo Nordeisk) can be used. These lipases may be immobilized if necessary.
  • Examples of the two or more lipases containing one or more of the above-mentioned monoglyceride rivase and Z or diglyceride rivase and one or more other rivases used in the present invention include, for example, Penicillium and Candida. Or a combination of a genera of the genus Pseudomonas and the genus Mukoru, or a genus of the genus Pseudomonas and Rhizopus.
  • the two or more rivases may be added all at once from the start of the reaction, or may be added one or several at a time.
  • the amount of lipase to be added may be any amount as long as the above purpose can be achieved.For example, 0.1 to 1000 units per 1 g of fat or oil, usually about 1 to 2000 units are used. I do.
  • the hydrolysis reaction in the present invention must be carried out in the presence of a sufficient amount of water or a buffer, for example, 1 to 100% (% by weight) with respect to fish oil, preferably 10 to 10%. Use around 0%.
  • the hydrolysis reaction proceeds by static or stirring at a temperature at which the lipase used is not inactivated.
  • the fat is hydrolyzed using two or more of the above specific lipases, and the glycerin-fatty acid produced by the hydrolysis reaction is obtained by a known method, such as alcohol deoxidation, steam distillation, solvent extraction, ion exchange resin, etc. It can be removed by the following method. In this way, the glyceride portion is fractionated from the hydrolyzed oil, and an oil or fat achieving the above object can be obtained.
  • the progress of the hydrolysis reaction can be grasped by measuring the acid value of the reaction mixture. That is, the hydrolysis rate is given by the following formula [1]:
  • Hydrolysis rate (%) (acid value Z saponification value of base oil) X 100 I: 1]
  • the recovery rate of each fatty acid is based on the corresponding fatty acid amount in the base oil and the corresponding fatty acid amount in the lipase-treated oil. It is determined from the ratio of For example, the DI-IA recovery rate is obtained from the ratio of the amount of DHA in the feedstock to the amount of DHA ift in rivase-treated Shanchu. That is, the following equation [2]:
  • Example 1
  • Tuna oil (D HA 21.97% s 7.60% EPA, D HA / EPA 2.89, saponification value 185) 2 m1, Mucor Meiha in 2 m1 of distilled water
  • lipase derived from lipase (trade name: Lipozyme, Novo Nordisk) 400 units per unit, lipase derived from Penicillium Power Mmberberry [trade name: Reno. —Ze G, Amano Pharmaceutical Co., Ltd.] 80 units were added and stirred at 35 ° C. for 16 hours.
  • the hydrolysis rate was 43.4%.
  • the glyceride fraction obtained by deacidifying and dehydrating the hydrolyzate is DHA 35.72%, EPA 7.27%, DHA ZE PA 4.92, and DHA is selected for EPA. Concentrated. At this time, the DHA recovery rate was as high as 92.6%.
  • Example 3 The test was performed again under the same conditions as in Example 1. The hydrolysis rate was 46.6%, and the resulting glyceride fraction was DHA 37.14%, EPA 7.01%, and DHA / EPA 5.30. It was selectively concentrated. At this time, the DHA recovery rate was as high as 90.23%.
  • Example 3 The hydrolysis rate was 46.6%, and the resulting glyceride fraction was DHA 37.14%, EPA 7.01%, and DHA / EPA 5.30. It was selectively concentrated. At this time, the DHA recovery rate was as high as 90.23%.
  • Example 3 The hydrolysis rate was 46.6%, and the resulting glyceride fraction was DHA 37.14%, EPA 7.01%, and DHA / EPA 5.30. It was selectively concentrated. At this time, the DHA recovery rate was as high as 90.23%.
  • Example 3 The hydrolysis rate was 46.6%, and the resulting glyceride fraction was DHA 37.14%, EPA 7.01%,
  • the hydrolysis rate was 50.6%.
  • the glyceride fraction obtained by deacidifying and dehydrating the hydrolyzate is DHA 39.58%, EPA 7.48%, DHA In ZE PA 5.29, D HA was selectively enriched for EPA. At this time, the DHA recovery rate was as high as 88.94%. Comparative Example 1
  • Example 2 The same as in Example 1, 2 ml of tuna oil and 2 ml of distilled water were added with 400 units of rivase derived from Mucor Mihai, and 35 ° C without addition of lipase derived from Penicillium Power Mamberti For 16 hours.
  • the hydrolysis rate was 25.1%, and the hydrolysis reaction did not proceed much as compared with Example 1.
  • the glyceride fraction obtained by deoxidizing and dehydrating the hydrolyzate showed a high DHA recovery rate of 97.17%, but the concentration capacity was DHA 28.5 2%, EPA 7.74%, DHA / EPA 3.69 resulted in less concentrated DHA.
  • Lipase derived from Candida Silicone Drache [Trade name: Lipase OF, Meito Sangyo Co., Ltd.] in 2 m 1 of tuna oil and 2 m 1 of distilled water as in Example 1 200 units, Penicillium power 40 uM of mannose-derived lyase was added, and the mixture was stirred at 35 ° C for 16 hours.
  • the hydrolysis rate was 52.6% (the glyceride fraction obtained by deacidifying and dehydrating the hydrolyzate was DHA 40.86%, EPA 8.84%, DHA / EPA 4.6)
  • DHA was selectively enriched for EPA.
  • Example 2 To 2 ml of tuna oil and 2 ml of distilled water as in Example 1, 400 units of lipase derived from Candida silyl dorache and 400 units of lipase derived from Penicillium power manberti were added. The mixture was stirred at C for 20 hours. The hydrolysis rate was 74.0%. The glyceride fraction obtained by deacidifying and dehydrating the hydrolyzate is DHA48.10%, EPA5.50%, and DHA / EPA8.75. Was selectively concentrated. Comparative Example 3
  • Example 4 To 2 ml of tuna oil and 2 ml of distilled water, the same as in Example 1, 200 units of lipase derived from Candida silicon dorache was added, and at 35 ° C without addition of lipase derived from Penicillium kerman Berti. Stirred for 16 hours. The hydrolysis rate was 34.1%, and the hydrolysis reaction did not progress as compared with Example 4. won.
  • the glyceride fraction obtained by deacidifying and dehydrating the hydrolyzate was DHA 31.82%, EPA 9.08%, DHA / EPA 3.51, and although DHA was concentrated, As compared with Example 4, the value was low, and the selective enrichment of DHA with respect to EPA was low. Comparative Example 4
  • Example 2 To 2 ml of the same tuna oil and 2 ml of distilled water as in Example 1, 1600 units of lipase derived from Candida Silicone Drachet were added, and 3 g of lipase derived from Penicillium Powerummberti were added. Stirred at 5 ° C for 20 hours. The hydrolysis rate was 62.7%. Compared with Example 5, the hydrolysis reaction had not progressed. The glyceride fraction obtained by deacidifying and dehydrating the hydrolyzate was DHA 44.74%, EPA 5.78%, and DHA / EPA 7.78. The results showed a low value in comparison, and the selective enrichment of DHA for EPA was also low.
  • Ripase derived from Rhizopus oryzae (trade name: Lipase F—AP15, Amano Pharmaceutical Co., Ltd.) 400 units, Benishirium power in 2 ml of tuna oil and 2 ml of distilled water as in Example 1 80 units of lipase derived from Nmberti were added, and the mixture was stirred at 35 ° C for 16 hours. The hydrolysis rate was 51.8%.
  • the glyceride fraction obtained by deacidifying and dehydrating the hydrolyzate is ⁇ 0
  • DHA was selectively enriched over EPA.
  • Example 7 To 2 ml of tuna oil and 2 ml of distilled water as in Example 1, 400 liters of lipase derived from Rhizobium spores was added, and 35 ° C without addition of lipase derived from P. nigerium manmberti. For 16 hours. The hydrolysis rate was 32.7%, and the hydrolysis reaction did not proceed as compared with Example 6. The glyceride fraction obtained by deoxidizing and dehydrating the hydrolyzate was DHA 32.08% EPA 7.05% DHA / EPA 4.55, and DHA was concentrated. Compared to 6, the value was low, and the selective enrichment of DHA for EPA was also low. Example 7
  • Example 6 With respect to the DHA concentrated oil obtained in Example 6, the rivase reaction was further repeated. That is, 2 ml of the glyceride fraction obtained in Example 6 and 2 ml of distilled water were added to 400 ml of lysose olase-derived lipase and 80 liters of lipase derived from sillium mannberti. Then, the mixture was stirred at 35 C for 16 hours. The hydrolysis rate was 35.6%. The hydrolyzate was deacidified. The glyceride fraction obtained by dehydration was DHA 52.36% EPA 5.81% DHA / EPA9 ⁇ 011. Compared with Example 6, the selective enrichment of DHA with respect to EPA was further improved.
  • lipases with much lower DHA-selective enrichment compared to lipases from Candida silin dorache can be combined with monoglyceride lipase and Z or diglyceride lipase.
  • a highly unsaturated fatty acid-containing fat or oil with an increased ratio of DHA to EPA can be produced.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

L'invention porte sur un procédé de production de matières grasses contenant des acides gras hautement insaturés contenant eux-mêmes un acide docosahexaénoïque à concentration sélective, ce procédé consistant à hydrolyser les matières grasses contenant des acides gras hautement insaturés avec des lipases ayant une capacité élevée à concentrer sélectivement l'acide docosahexaénoïque. Ces lipases sont au moins deux lipases comprenant une lipase monoglycéride et/ou une lipase diglycéride et provenant de micro-organismes appartenant aux genres Penicillium et Candida, Penicillium et Mucor, ou Penicillium et Rhizopus. Ce procédé permet d'obtenir des matières grasses contenant des acides gras hautement insaturés et présentant un rapport élevé de DHA/EPA.
PCT/JP1997/003949 1996-10-30 1997-10-30 Procede de production de matieres grasses contenant des acides gras hautement insatures contenant eux-memes un acide docosahexaenoique a concentration selective Ceased WO1998018952A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP30410496 1996-10-30
JP8/304104 1996-10-30

Publications (1)

Publication Number Publication Date
WO1998018952A1 true WO1998018952A1 (fr) 1998-05-07

Family

ID=17929086

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/003949 Ceased WO1998018952A1 (fr) 1996-10-30 1997-10-30 Procede de production de matieres grasses contenant des acides gras hautement insatures contenant eux-memes un acide docosahexaenoique a concentration selective

Country Status (1)

Country Link
WO (1) WO1998018952A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000049117A1 (fr) * 1999-02-17 2000-08-24 Norsk Hydro Asa Esterification d'huile marine catalysee par lipase
JP2002136298A (ja) * 2000-11-01 2002-05-14 Tama Seikagaku Kk Ｄｈａを高濃度に含有するアシルグリセリドの製造方法
US7678930B2 (en) 2002-07-11 2010-03-16 Pronova Biopharma Norge As Process for decreasing the amount of cholesterol in a marine oil using a volatile working fluid
US7718698B2 (en) 2002-07-11 2010-05-18 Pronova Biopharma Norge As Process for decreasing environmental pollutants in an oil or a fat
JP2010183881A (ja) * 2009-02-13 2010-08-26 Kao Corp ドコサヘキサエン酸高含有油脂の製造方法
US7807849B2 (en) 2004-04-22 2010-10-05 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US7834250B2 (en) 2004-04-22 2010-11-16 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
WO2011149040A1 (fr) 2010-05-28 2011-12-01 日本水産株式会社 Procédé de production d'huile ou de graisse contenant un acide gras fortement insaturé au moyen d'une lipase
JP2013055893A (ja) * 2011-09-07 2013-03-28 Nippon Suisan Kaisha Ltd 高度不飽和脂肪酸濃縮油の製造方法
US8816111B2 (en) 2012-06-15 2014-08-26 Commonwealth Scientific And Industrial Research Organisation Lipid comprising polyunsaturated fatty acids
US9718759B2 (en) 2013-12-18 2017-08-01 Commonwealth Scientific And Industrial Research Organisation Lipid comprising docosapentaenoic acid
US9938486B2 (en) 2008-11-18 2018-04-10 Commonwealth Scientific And Industrial Research Organisation Enzymes and methods for producing omega-3 fatty acids
US10005713B2 (en) 2014-06-27 2018-06-26 Commonwealth Scientific And Industrial Research Organisation Lipid compositions comprising triacylglycerol with long-chain polyunsaturated fatty acids at the sn-2 position
US10513717B2 (en) 2006-08-29 2019-12-24 Commonwealth Scientific And Industrial Research Organisation Synthesis of fatty acids
CN110835637A (zh) * 2019-11-22 2020-02-25 华南理工大学 一种脂肪酸的合成方法
WO2020050304A1 (fr) 2018-09-04 2020-03-12 日本水産株式会社 Procédé de fabrication de glycéride à teneur en acide docosahexaénoïque mettant en œuvre une réaction d'hydrolyse par lipase
WO2020050303A1 (fr) 2018-09-04 2020-03-12 日本水産株式会社 Procédé de production de glycéride contenant un acide gras polyinsaturé au moyen d'une réaction d'hydrolyse par une lipase
CN110878289A (zh) * 2019-12-26 2020-03-13 中国海洋大学 一种脂肪酶及其应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02295490A (ja) * 1989-05-10 1990-12-06 Nippon Oil & Fats Co Ltd 油脂加水分解物の改質方法
JPH02295489A (ja) * 1989-05-10 1990-12-06 Nippon Oil & Fats Co Ltd 長鎖高度不飽和脂肪酸含有トリグリセリドの製造方法
JPH0751075A (ja) * 1993-08-18 1995-02-28 Nippon Oil & Fats Co Ltd ドコサヘキサエン酸含有物質の製造方法
JPH08214892A (ja) * 1995-02-17 1996-08-27 Osaka City 高度不飽和脂肪酸含有部分グリセリドの製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02295490A (ja) * 1989-05-10 1990-12-06 Nippon Oil & Fats Co Ltd 油脂加水分解物の改質方法
JPH02295489A (ja) * 1989-05-10 1990-12-06 Nippon Oil & Fats Co Ltd 長鎖高度不飽和脂肪酸含有トリグリセリドの製造方法
JPH0751075A (ja) * 1993-08-18 1995-02-28 Nippon Oil & Fats Co Ltd ドコサヘキサエン酸含有物質の製造方法
JPH08214892A (ja) * 1995-02-17 1996-08-27 Osaka City 高度不飽和脂肪酸含有部分グリセリドの製造方法

Cited By (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000049117A1 (fr) * 1999-02-17 2000-08-24 Norsk Hydro Asa Esterification d'huile marine catalysee par lipase
US6518049B1 (en) 1999-02-17 2003-02-11 Norsk Hydro Asa Lipase-catalysed esterification of marine oil
JP2002136298A (ja) * 2000-11-01 2002-05-14 Tama Seikagaku Kk Ｄｈａを高濃度に含有するアシルグリセリドの製造方法
US7678930B2 (en) 2002-07-11 2010-03-16 Pronova Biopharma Norge As Process for decreasing the amount of cholesterol in a marine oil using a volatile working fluid
US7718698B2 (en) 2002-07-11 2010-05-18 Pronova Biopharma Norge As Process for decreasing environmental pollutants in an oil or a fat
US7732488B2 (en) 2002-07-11 2010-06-08 Pronova Biopharma Norge As Pharmaceutical composition comprising low concentrations of environmental pollutants
US9453183B2 (en) 2004-04-22 2016-09-27 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US10781463B2 (en) 2004-04-22 2020-09-22 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US7834250B2 (en) 2004-04-22 2010-11-16 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US7932438B2 (en) 2004-04-22 2011-04-26 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US11597953B2 (en) 2004-04-22 2023-03-07 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US8071341B2 (en) 2004-04-22 2011-12-06 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US8158392B1 (en) 2004-04-22 2012-04-17 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US11220698B2 (en) 2004-04-22 2022-01-11 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US9951357B2 (en) 2004-04-22 2018-04-24 Commonweatlh Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US7807849B2 (en) 2004-04-22 2010-10-05 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US8853432B2 (en) 2004-04-22 2014-10-07 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US9926579B2 (en) 2004-04-22 2018-03-27 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US9963723B2 (en) 2004-04-22 2018-05-08 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cells
US9458410B2 (en) 2004-04-22 2016-10-04 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US10443079B2 (en) 2004-04-22 2019-10-15 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US9994880B2 (en) 2004-04-22 2018-06-12 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US9970033B2 (en) 2004-04-22 2018-05-15 Commonwealth Scientific And Industrial Research Organisation Synthesis of long-chain polyunsaturated fatty acids by recombinant cell
US10513717B2 (en) 2006-08-29 2019-12-24 Commonwealth Scientific And Industrial Research Organisation Synthesis of fatty acids
US9938486B2 (en) 2008-11-18 2018-04-10 Commonwealth Scientific And Industrial Research Organisation Enzymes and methods for producing omega-3 fatty acids
JP2010183881A (ja) * 2009-02-13 2010-08-26 Kao Corp ドコサヘキサエン酸高含有油脂の製造方法
KR20130111233A (ko) 2010-05-28 2013-10-10 닛폰 스이산 가부시키가이샤 리파아제에 의한 고도 불포화 지방산 함유 유지의 제조 방법
US10138502B2 (en) 2010-05-28 2018-11-27 Nippon Suisan Kaisha, Ltd. Method for producing oil containing polyunsaturated fatty acid using lipase
WO2011149040A1 (fr) 2010-05-28 2011-12-01 日本水産株式会社 Procédé de production d'huile ou de graisse contenant un acide gras fortement insaturé au moyen d'une lipase
JP2013055893A (ja) * 2011-09-07 2013-03-28 Nippon Suisan Kaisha Ltd 高度不飽和脂肪酸濃縮油の製造方法
US9932289B2 (en) 2012-06-15 2018-04-03 Commonwealth Scientific And Industrial Research Ogranisation Process for producing ethyl esters of polyunsaturated fatty acids
US9550718B2 (en) 2012-06-15 2017-01-24 Commonwealth Scientific And Industrial Research Organisation Lipid comprising polyunsaturated fatty acids
US8816111B2 (en) 2012-06-15 2014-08-26 Commonwealth Scientific And Industrial Research Organisation Lipid comprising polyunsaturated fatty acids
US9556102B2 (en) 2012-06-15 2017-01-31 Commonwealth Scientific And Industrial Research Organisation Process for producing ethyl esters of polyunsaturated fatty acids
US8946460B2 (en) 2012-06-15 2015-02-03 Commonwealth Scientific And Industrial Research Organisation Process for producing polyunsaturated fatty acids in an esterified form
US10335386B2 (en) 2012-06-15 2019-07-02 Commonwealth Scientific And Industrial Research Organisation Lipid comprising polyunsaturated fatty acids
US10190073B2 (en) 2013-12-18 2019-01-29 Commonwealth Scientific And Industrial Research Organisation Lipid comprising long chain polyunsaturated fatty acids
US11623911B2 (en) 2013-12-18 2023-04-11 Commonwealth Scientific And Industrial Research Organisation Lipid comprising docosapentaenoic acid
US10800729B2 (en) 2013-12-18 2020-10-13 Commonwealth Scientific And Industrial Research Organisation Lipid comprising long chain polyunsaturated fatty acids
US9718759B2 (en) 2013-12-18 2017-08-01 Commonwealth Scientific And Industrial Research Organisation Lipid comprising docosapentaenoic acid
US9725399B2 (en) 2013-12-18 2017-08-08 Commonwealth Scientific And Industrial Research Organisation Lipid comprising long chain polyunsaturated fatty acids
US10125084B2 (en) 2013-12-18 2018-11-13 Commonwealth Scientific And Industrial Research Organisation Lipid comprising docosapentaenoic acid
US10005713B2 (en) 2014-06-27 2018-06-26 Commonwealth Scientific And Industrial Research Organisation Lipid compositions comprising triacylglycerol with long-chain polyunsaturated fatty acids at the sn-2 position
US10793507B2 (en) 2014-06-27 2020-10-06 Commonwealth Scientific And Industrial Research Organisation Lipid compositions comprising triacylglycerol with long-chain polyunsaturated fatty acids at the SN-2 position
WO2020050304A1 (fr) 2018-09-04 2020-03-12 日本水産株式会社 Procédé de fabrication de glycéride à teneur en acide docosahexaénoïque mettant en œuvre une réaction d'hydrolyse par lipase
JPWO2020050304A1 (ja) * 2018-09-04 2021-09-30 日本水産株式会社 リパーゼ加水分解反応を用いるドコサヘキサエン酸含有グリセリドの製造方法
US20210324432A1 (en) * 2018-09-04 2021-10-21 Nippon Suisan Kaisha, Ltd. Method of producing docosahexaenoic acid containing glyceride using a lipase hydrolysis reaction
EP3848465A4 (fr) * 2018-09-04 2022-06-29 Nippon Suisan Kaisha, Ltd. Procédé de fabrication de glycéride à teneur en acide docosahexaénoïque mettant en oeuvre une réaction d'hydrolyse par lipase
WO2020050303A1 (fr) 2018-09-04 2020-03-12 日本水産株式会社 Procédé de production de glycéride contenant un acide gras polyinsaturé au moyen d'une réaction d'hydrolyse par une lipase
US11840714B2 (en) 2018-09-04 2023-12-12 Nissui Corporation Enriching DHA in glyceride fractions
CN110835637A (zh) * 2019-11-22 2020-02-25 华南理工大学 一种脂肪酸的合成方法
CN110878289A (zh) * 2019-12-26 2020-03-13 中国海洋大学 一种脂肪酶及其应用

Similar Documents

Publication Publication Date Title
WO1998018952A1 (fr) Procede de production de matieres grasses contenant des acides gras hautement insatures contenant eux-memes un acide docosahexaenoique a concentration selective
Shimada et al. Purification of docosahexaenoic acid by selective esterification of fatty acids from tuna oil with Rhizopus delemar lipase
JP4530311B2 (ja) リパーゼを用いたグリセライドの製造方法
JP4236128B2 (ja) 精油組成物
US6537787B1 (en) Enzymatic methods for polyunsaturated fatty acid enrichment
CN102959083A (zh) 利用脂肪酶的含高度不饱和脂肪酸的油脂的制造方法
JP5416861B2 (ja) リパーゼによる高度不飽和脂肪酸含有油脂の製造方法
Nagao et al. Purification of conjugated linoleic acid isomers through a process including lipase-catalyzed selective esterification
JPH08302384A (ja) 高度不飽和脂肪酸の酵素分画方法
JP4079516B2 (ja) トリグリセリドの製造方法
Kojima et al. Different specificity of two types of Pseudomonas lipases for C20 fatty acids with a Δ5 unsaturated double bond and their application for selective concentration of fatty acids
JPH08214892A (ja) 高度不飽和脂肪酸含有部分グリセリドの製造方法
JP3840459B2 (ja) グリセリドおよびその製造方法
JP5237627B2 (ja) 高度不飽和脂肪酸の濃縮方法
JP4276539B2 (ja) オメガ６ｐｕｆａを含むコレステロール低下構造脂質
JP4310387B2 (ja) ω−３系高度不飽和脂肪酸含有部分グリセリド組成物及びその製造方法
JPH07268382A (ja) 長鎖高度不飽和脂肪酸含有油脂の製造方法
JP6645804B2 (ja) 構造油脂の製造方法
Fajardo et al. Concentration of eicosapentaenoic acid by selective esterification using lipases
JP5852972B2 (ja) 高度不飽和脂肪酸の濃縮方法
JP2007070486A (ja) グリセリド及びその製造方法
JPH10265795A (ja) 水和性を高めた高度不飽和脂肪酸含有油脂組成物
JP2008278781A (ja) ２位よりも１，３位のｄｈａ含有率が高いトリアシルグリセロールの製造方法
JP2007089522A5 (fr)
JP3995409B2 (ja) ５，８，１１−エイコサトリエン酸及び／又は６，９−オクタデカジエン酸を高濃度に含有するグリセリドの製造方法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA