WO2005038037A3 - Methods for preparing phospholipids containing omega-3 and omega-6 moieties - Google Patents
Methods for preparing phospholipids containing omega-3 and omega-6 moieties Download PDFInfo
- Publication number
- WO2005038037A3 WO2005038037A3 PCT/IL2004/000958 IL2004000958W WO2005038037A3 WO 2005038037 A3 WO2005038037 A3 WO 2005038037A3 IL 2004000958 W IL2004000958 W IL 2004000958W WO 2005038037 A3 WO2005038037 A3 WO 2005038037A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- omega
- methods
- moieties
- phospholipids containing
- preparing
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 title abstract 2
- 150000003904 phospholipids Chemical class 0.000 title 1
- 230000002255 enzymatic effect Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 abstract 1
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 abstract 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 abstract 1
- 101100083853 Homo sapiens POU2F3 gene Proteins 0.000 abstract 1
- 101100058850 Oryza sativa subsp. japonica CYP78A11 gene Proteins 0.000 abstract 1
- 101150059175 PLA1 gene Proteins 0.000 abstract 1
- 102100026466 POU domain, class 2, transcription factor 3 Human genes 0.000 abstract 1
- 102100026918 Phospholipase A2 Human genes 0.000 abstract 1
- 101710096328 Phospholipase A2 Proteins 0.000 abstract 1
- 102000011420 Phospholipase D Human genes 0.000 abstract 1
- 108090000553 Phospholipase D Proteins 0.000 abstract 1
- 102000015439 Phospholipases Human genes 0.000 abstract 1
- 108010064785 Phospholipases Proteins 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 150000002327 glycerophospholipids Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 abstract 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 abstract 1
- 150000003905 phosphatidylinositols Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
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
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6481—Phosphoglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- 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
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
-
- 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
-
- 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
- C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL158553 | 2003-10-22 | ||
IL15855303A IL158553A0 (en) | 2003-10-22 | 2003-10-22 | Method for preparing phosphatidylserine containing omega-3 acid moieties |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2005038037A2 WO2005038037A2 (en) | 2005-04-28 |
WO2005038037A3 true WO2005038037A3 (en) | 2005-12-01 |
Family
ID=34044223
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IL2004/000958 WO2005038037A2 (en) | 2003-10-22 | 2004-10-21 | Methods for preparing phospholipids containing omega-3 and omega-6 moieties |
Country Status (2)
Country | Link |
---|---|
IL (1) | IL158553A0 (en) |
WO (1) | WO2005038037A2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9028877B2 (en) | 2007-03-28 | 2015-05-12 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
US9220735B2 (en) | 2007-03-28 | 2015-12-29 | Aker Biomarine Antarctic As | Methods of using krill oil to treat risk factors for cardiovascular, metabolic, and inflammatory disorders |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8052992B2 (en) | 2003-10-22 | 2011-11-08 | Enzymotec Ltd. | Glycerophospholipids containing omega-3 and omega-6 fatty acids and their use in the treatment and improvement of cognitive functions |
US7935365B2 (en) | 2003-10-22 | 2011-05-03 | Enzymotec, Ltd. | Glycerophospholipids for the improvement of cognitive functions |
US20050130937A1 (en) | 2003-10-22 | 2005-06-16 | Enzymotec Ltd. | Lipids containing omega-3 and omega-6 fatty acids |
CA2654631A1 (en) * | 2006-06-09 | 2007-12-13 | Erasmus University Medical Center Rotterdam | Modulation of the immune system by inositol phospholipids |
WO2009020406A1 (en) * | 2007-08-07 | 2009-02-12 | Granate Seed Limited | Methods of making lipid substances, lipid substances made thereby and uses thereof |
US8372812B2 (en) | 2009-02-26 | 2013-02-12 | Aker Biomarine Asa | Phospholipid and protein tablets |
WO2011095836A2 (en) * | 2010-02-02 | 2011-08-11 | Soluciones Extractivas Alimentarias, S.L. (Solutex) | Trackable therapeutic macrophages |
US11712429B2 (en) | 2010-11-29 | 2023-08-01 | Amarin Pharmaceuticals Ireland Limited | Low eructation composition and methods for treating and/or preventing cardiovascular disease in a subject with fish allergy/hypersensitivity |
NZ744990A (en) | 2010-11-29 | 2019-10-25 | Amarin Pharmaceuticals Ie Ltd | Low eructation composition and methods for treating and/or preventing cardiovascular disease in a subject with fish allergy/hypersensitivity |
US8846604B2 (en) | 2011-09-02 | 2014-09-30 | Artic Nutrition AS | Lipid compositions with high DHA content |
WO2013136183A2 (en) | 2012-03-12 | 2013-09-19 | Innolipid, As | Oxidixable fatty acid composition delivery form |
CN104379757B (en) * | 2012-06-13 | 2017-03-15 | 株式会社钟化 | Contain the manufacture method of phospholipid composite and contain phospholipid composite |
US20140080791A1 (en) | 2012-09-19 | 2014-03-20 | Aker Biomarine As | Omega-3 phospholipid supplements for females |
AU2014229540A1 (en) | 2013-03-14 | 2015-10-08 | Aker Biomarine Antarctic As | Omega- 3 phospholipid supplements for improved brain maturity |
AU2014203179C1 (en) | 2013-06-14 | 2017-05-04 | Aker Biomarine Antarctic As | Lipid extraction processes |
CA2932766C (en) | 2013-12-05 | 2018-05-01 | Enzymotec Ltd. | Serine glycerophospholipid preparation and method for treatment of seizures |
GB201400431D0 (en) | 2014-01-10 | 2014-02-26 | Aker Biomarine As | Phospholipid compositions and their preparation |
ES2745226T3 (en) | 2014-11-20 | 2020-02-28 | Enzymotec Ltd | Preparation of phospholipids for the improvement of communication skills |
KR102515207B1 (en) | 2015-02-11 | 2023-03-29 | 에이커 바이오마린 앤탁틱 에이에스 | Lipid compositions |
WO2016128830A1 (en) | 2015-02-11 | 2016-08-18 | Aker Biomarine Antarctic As | Lipid extraction processes |
US10894056B2 (en) | 2015-07-13 | 2021-01-19 | Enzymotec Ltd | Phospholipid preparations for the improvement of sleep |
AU2017231891B2 (en) | 2016-03-10 | 2022-03-10 | Frutarom Limited | Phospholipid preparations for the improvement of brain plasticity |
FI4056176T3 (en) | 2018-09-24 | 2024-05-30 | Amarin Pharmaceuticals Ie Ltd | Methods of reducing the risk of cardiovascular events in a subject |
WO2020177728A1 (en) * | 2019-03-05 | 2020-09-10 | 四川国为制药有限公司 | Fatty acid composition and application thereof |
CN109852643B (en) * | 2019-03-18 | 2022-05-06 | 威海深蓝奇迹生物科技有限公司 | Method for preparing sn-1-DHA-lyso-phosphatidylserine |
CA3145418A1 (en) * | 2019-06-26 | 2020-12-30 | Kannalife Sciences, Inc. | Use of certain phosphatidylcholines containing long chain polyunsaturated fatty acids as neuroprotective agents |
CN111154813A (en) * | 2020-01-19 | 2020-05-15 | 烟台新时代健康产业日化有限公司 | Preparation method of euphausia superba phospholipid |
CN111518814B (en) * | 2020-05-19 | 2022-07-01 | 西南大学 | Application and method of brassica napus Bna.A05DAD1 gene |
AU2022263358A1 (en) | 2021-04-21 | 2023-11-30 | Amarin Pharmaceuticals Ireland Limited | Methods of reducing the risk of heart failure |
US20230091294A1 (en) * | 2021-09-22 | 2023-03-23 | Wilson Martinez Gutierrez | Enzymatically synthesized omega-3 structured phospholipids |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991000918A1 (en) * | 1989-07-12 | 1991-01-24 | Berol Nobel Ab | A METHOD FOR THE PREPARATION OF A PHOSPHOLIPID WITH A CARBOXYLIC ACID RESIDUE IN THE 2-POSITION AND A PHOSPHOLIPID WITH AN φ-3-FATTY ACID RESIDUE IN THE 2-POSITION |
WO1991003564A1 (en) * | 1989-08-30 | 1991-03-21 | Novo Nordisk A/S | Interesterification of phospholipids |
US5288619A (en) * | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
EP0609078A1 (en) * | 1993-01-27 | 1994-08-03 | Scotia Holdings Plc | Formulations containing unsaturated fatty acids |
EP0739985A2 (en) * | 1995-04-24 | 1996-10-30 | Societe Des Produits Nestle S.A. | Process for phospholipid interesterification |
US6369252B1 (en) * | 1998-02-26 | 2002-04-09 | The University Of Georgia Research Foundation, Inc. | Structured lipids |
WO2005037848A2 (en) * | 2003-10-22 | 2005-04-28 | Enzymotec Ltd. | Glycerophospholipids containing omega-3 and omega-6 fatty acids |
-
2003
- 2003-10-22 IL IL15855303A patent/IL158553A0/en unknown
-
2004
- 2004-10-21 WO PCT/IL2004/000958 patent/WO2005038037A2/en active Application Filing
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991000918A1 (en) * | 1989-07-12 | 1991-01-24 | Berol Nobel Ab | A METHOD FOR THE PREPARATION OF A PHOSPHOLIPID WITH A CARBOXYLIC ACID RESIDUE IN THE 2-POSITION AND A PHOSPHOLIPID WITH AN φ-3-FATTY ACID RESIDUE IN THE 2-POSITION |
WO1991003564A1 (en) * | 1989-08-30 | 1991-03-21 | Novo Nordisk A/S | Interesterification of phospholipids |
US5288619A (en) * | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
EP0609078A1 (en) * | 1993-01-27 | 1994-08-03 | Scotia Holdings Plc | Formulations containing unsaturated fatty acids |
EP0739985A2 (en) * | 1995-04-24 | 1996-10-30 | Societe Des Produits Nestle S.A. | Process for phospholipid interesterification |
US6369252B1 (en) * | 1998-02-26 | 2002-04-09 | The University Of Georgia Research Foundation, Inc. | Structured lipids |
WO2005037848A2 (en) * | 2003-10-22 | 2005-04-28 | Enzymotec Ltd. | Glycerophospholipids containing omega-3 and omega-6 fatty acids |
Non-Patent Citations (3)
Title |
---|
KIM JUHAN ET AL: "Production of egg yolk lysolecithin with immobilized phospholipase A2", ENZYME AND MICROBIAL TECHNOLOGY, vol. 29, no. 10, 5 December 2001 (2001-12-05), pages 587 - 592, XP002335012, ISSN: 0141-0229 * |
MUTUA L N ET AL: "LIPASE-CATALYZED MODIFICATION OF PHOSPHOLIPIDS: INCORPORATION OF N-3 FATTY ACIDS INTO BIOSURFACTANTS", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, AMERICAN OIL CHEMISTS' SOCIETY, CHAMPAIGN, IL, US, vol. 70, no. 2, February 1993 (1993-02-01), pages 125 - 128, XP008048477, ISSN: 0003-021X * |
PARK CHANG WON ET AL: "Transesterification of phosphatidylcholine with eicosapentaenoic acid ethyl ester using phospholipase A2 in organic solvent", BIOTECHNOLOGY LETTERS, vol. 22, no. 2, January 2000 (2000-01-01), pages 147 - 150, XP002335196, ISSN: 0141-5492 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9028877B2 (en) | 2007-03-28 | 2015-05-12 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
US9034388B2 (en) | 2007-03-28 | 2015-05-19 | Aker Biomarine Antartic As | Bioeffective krill oil compositions |
US9072752B1 (en) | 2007-03-28 | 2015-07-07 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
US9078905B2 (en) | 2007-03-28 | 2015-07-14 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
US9119864B2 (en) | 2007-03-28 | 2015-09-01 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
US9220735B2 (en) | 2007-03-28 | 2015-12-29 | Aker Biomarine Antarctic As | Methods of using krill oil to treat risk factors for cardiovascular, metabolic, and inflammatory disorders |
US9320765B2 (en) | 2007-03-28 | 2016-04-26 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
US9375453B2 (en) | 2007-03-28 | 2016-06-28 | Aker Biomarine Antarctic As | Methods for producing bioeffective krill oil compositions |
Also Published As
Publication number | Publication date |
---|---|
IL158553A0 (en) | 2004-05-12 |
WO2005038037A2 (en) | 2005-04-28 |
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