WO1996031457A1 - Triglycerides - Google Patents

Triglycerides Download PDF

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Publication number
WO1996031457A1
WO1996031457A1 PCT/GB1996/000828 GB9600828W WO9631457A1 WO 1996031457 A1 WO1996031457 A1 WO 1996031457A1 GB 9600828 W GB9600828 W GB 9600828W WO 9631457 A1 WO9631457 A1 WO 9631457A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
triglycerides
residue
fatty acids
acids
Prior art date
Application number
PCT/GB1996/000828
Other languages
English (en)
Inventor
David Frederick Horrobin
Austin Mcmordie
Mehar Singh Manku
Philip Knowles
Original Assignee
Scotia Holdings Plc
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 Scotia Holdings Plc filed Critical Scotia Holdings Plc
Priority to NZ304924A priority Critical patent/NZ304924A/xx
Priority to AU52809/96A priority patent/AU5280996A/en
Priority to EP96909235A priority patent/EP0832058A1/fr
Publication of WO1996031457A1 publication Critical patent/WO1996031457A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
    • 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

Definitions

  • the invention relates to triglycerides.
  • the essential fatty acids consist of a series of twelve compounds illustrated in Table 1 below.
  • Linoleic acid (LA) the parent compound of the n-6 series of EFAs
  • alpha-linolenic acid (ALA) the parent compound of the n-3 series
  • the parent compounds are metabolized by the sequence of reactions shown in Table 1.
  • DGLA dihomo-gamma-linolenic acid
  • AA arachidonic acid
  • EPA eicosapentaenoic acid
  • DHA docosahexaenoic acid
  • DGLA, AA, EPA and DHA are important constituents of most of the lipids in the body. As well as being important in themselves they can also give rise to a wide range of oxygenated derivatives, the eicosanoids, including the prostaglandins, leukotrienes and other compounds.
  • the acids which in nature are of the all-cis configuration, are systematically named as derivatives of the corresponding octadecanoic, eicosanoic or docosanoic acids, e.g. delta-9, 12-octadecadienoic acid or delta-4,7,10,13,16, 19-docosahexaenoic acid, but numerical designations such as, correspondingly, 18:2 n-6 or 22:6 n-3 are convenient.
  • n-3 series only 18:3 n-3 has a commonly used trivial name, alpha- linolenic acid, though the name stearidonic acid is coming into use for the 18:4 n-3 acid and die names eicosapentaenoic acid and docosahexanenoic acid as such are also used.
  • EFA biochemistry leading to abnormal EFA levels in various lipid fractions and in various tissues.
  • diseases of the heart and circulation such as hypertension and coronary and peripheral vascular disease, diseases of inflammation and immunity such as atopic disorders, osteoarthritis, rheumatoid arthritis, ulcerative colitis, Crohn's disease and various disorders going under the general classifications of inflammatory or auto-immune, neurological disorders such as Alzheimer's disease, Parkinson's disease and multiple sclerosis, disorders of the kidney, disorders of the skin, disorders of the gastrointestinal tract, disorders of metabolism of calcium and other minerals, disorders of bone and connective tissue, disorders of the reproductive and endocrine systems, psychiatric disorders including schizophrenia, and disorders of aging.
  • diseases of the heart and circulation such as hypertension and coronary and peripheral vascular disease, diseases of inflammation and immunity such as atopic disorders, osteoarthritis, rheumatoid arthritis, ulcerative colitis, Crohn's disease and various disorders going under the general classifications of inflammatory or auto-immune,
  • the EFAs are exceptionally susceptible to oxidation and so it may be appropriate to co-administer the EFAs with oleic acid (OA) which has potent properties as an antioxidant.
  • OA oleic acid
  • the EFAs can be supplied in various forms and in various mixtures, it is in principle convenient in both nutrition and in medical treatment to be able to supply the fatty acids as predetermined, particular molecules. This is particularly true with respect to pharmaceuticals, where regulations and directives covering combination products are becoming steadily more restrictive. For example, in order to win government approval for a combination drug product containing compounds A, B and C, it is now no longer adequate to mix the three compounds together in formulation X, and then to compare X with placebo, P.
  • the different EFAs and oleic acid may be present in the same molecule, either randomly distributed among the 1, 2 and 3 positions or with a particular EFA being found specifically in one of the positions on the molecule. With each triglyceride one or two positions will be occupied by one fatty acid while the other one or two positions will be occupied by one or two other fatty acids.
  • esterification may in principle be directed to favour a desired isomer, but if it is not, then the position of individual acid residues in the triglycerides produced from starting mixtures of two acids is one of the several possibilities: -
  • a previous filing has described in detail a range of triglycerides for use in pharmaceuticals, nutritional supplements, foods and skin care preparations.
  • the parent essential fatty acids, linoleic acid and alpha- linolenic acid had few biological actions themselves and so those fatty acids were excluded from the triglycerides described.
  • the described triglycerides contained fatty acids which were divided into one of the following four categories: a) GLA and DGLA. b) A A, adrenic acid and the 22:5n-6 acid. c) Stearidonic acid and the 20:4n-3 acid. d) EPA, the 22:5n-3 acid and DHA.
  • Triglycerides were described which contained either two residues of a fatty acid from one group, and one residue selected from a different group, or which contained three different fatty acids selected from three different groups. These triglycerides optionally contained oleic acid as one of the fatty acid residues due to its potent antioxidant properties.
  • LA and ALA themselves have little value may have been overstated and it is probable that LA and ALA do have important actions in their own right.
  • linoleic acid appears to have specific actions on the skin (Prottey et al, Br J Dermatol 1977; 97:29-38) and recent unpublished studies (AC Buck) indicate that it may stimulate calcium abso ⁇ tion from the gut.
  • ALA itself may have actions which result in a considerable reduction in the risk of myocardial infarction (M de Lorgeril et al, Lancet 1994; 343: 1454-9). It therefore seems that LA and ALA may have useful actions in their own right and that at the very least they do not have adverse effects and can act as useful carriers for the other fatty acids.
  • fatty acids might include stearic acid, palmitic acid, lauric acid, myristic acid or any other fatty acid containing 8 to 26 carbon atoms, whether saturated, mono-unsaturated or polyunsaturated, and whether in the case of unsaturated fatty acids having its double bonds in either cis or trans configurations.
  • the invention provides, as groups of isomers or singly, triglycerides containing :- a) one residue of an acid selected from oleic acid and the following groups of acids: -
  • GLA gamma-linolenic acid
  • DGLA dihomo-gamma linolenic acid
  • the groups of isomers so defined comprise mixtures of positional and/or optical isomers, which may be in the proportions arising from directed or undirected synthesis, or in proportions arising from treatment of as-synthesised mixtures to enhance the proportion of particular isomers or groups of isomers. Further, according to the method of synthesis and degree of enhancement if any, varying amounts of triglycerides other than those defined may also be present.
  • TG45 is the possible mono-linoleoyl - mono-alpha linolenoyl - mono- Group (iv) glycerides eg. the mono-linoleoyl) - mono - (alpha linolenoyl) - mono- (eicosapentanoyl) glyceride.
  • the table is:- Oleic G ⁇ .l G ⁇ .2 G ⁇ .3 G ⁇ .4 Other FA 1 - - 1
  • the invention may be considered in terms of starting mixtures of acids, selected from oleic acid and the acids of Groups i) - iv) above, linoleic acid, alpha-linolenic acid and other Cg_26 fatty acids, namely in molar terms (33% stands for one third, 66% stands for two thirds):- i) 33% of an acid selected from oleic acid and the acids of Groups i), ii), iii) and iv), 33% of a different acid selected therefrom and 33% of linoleic acid, alpha linolenic acid, or any other Cg_26 fatty acid other than oleic acid and the twelve n-6 and n-3 essential fatty acids; or ii) 66% of an acid selected from oleic acid and the acids of Groups i), ii), iii) and iv) and 33% of an acid selected from alpha-linole
  • Preferred starting mixtures with arbitrary reference numbers for the triglycerides, or rather possible groups of triglyceride isomers (TGs), that they formally represent, are derived from Table 3, specifying numbers of residues, by reading 33 mole % (one third) for ' 1 ' and 66 mole % (two thirds) for *2'.
  • species AAA and BBB of Tables 2a and 2b are for example unwanted components of the synthesized mixture but the mixed species predominate and the as-synthesized mixtures are therefore valuable.
  • species AAA and BBB of Tables 2a and 2b are for example unwanted components of the synthesized mixture but the mixed species predominate and the as-synthesized mixtures are therefore valuable.
  • desired species can be separated or part separated from others by chromatographic or other methods known in themselves.
  • triglycerides either containing three different fatty acids or two fatty acids in a 2: 1 ratio, may thus be manufactured by chemical or enzymatic means by methods known in themselves to those skilled in the art. If the method of synthesis or manufacture does not provide an adequate concentration of the desired triglyceride, then that triglyceride may be concentrated and purified by appropriate techniques as outlined later.
  • triglyceride isomers consist of new triglycerides which do not appear in nature and have not previously been described. They may broadly be prepared as follows: a) The individual fatty acids are purified from natural animal, vegetable or microbial sources or are chemically synthesized, there being methods known in themselves to those skilled in the art. b) The individual fatty acids are then esterified with glycerol by chemical or enzymatic methods, there being again methods known in themselves to those skilled in the art. For example, the fatty acids and glycerol may be allowed to react together in the presence of one of a number of appropriate enzymes, or of p-toluene sulphonic acid hydrate.
  • the specific triglycerides are further purified by appropriate methods, again known to those skilled in the art, in particular high pressure liquid chromatography or other appropriate forms of chromatography; low temperature crystallisation; or the use of solvents which differentially select triglycerides of particular composition.
  • a specified particular triglyceride or group of triglycerides forms more than 10%, preferably more than 30% very preferably more than 70% and ideally more than 90% of the triglycerides present in any triglyceride mixture used for the preparation of pharmaceutical compositions, foods, or skin care products.
  • the triglycerides may be made up into appropriate pharmaceuticals or foods so as to provide a daily dose of lmg to lOOg per day, preferably lOmg to lOg and very preferably 500mg to 4g.
  • the triglycerides may be inco ⁇ orated in concentrations of 0.001 to 50%, preferably 0.05 to 20% and very preferably 0.1 to 5%.
  • the specified triglycerides have a wide variety of possible uses. They may be used as pharmaceuticals for the treatment or prevention of disease in which abnormalities of EFAs have been identified. They may be added to foods or be added to or used as nutritional supplements for those who require the particular EFAs for the treatment or prevention of disease. They may also be used in foods or pharmaceuticals for veterinary use. They may be used for skin care.
  • the triglycerides may be formulated in any way appropriate, as well known to those skilled in the art of preparing pharmaceuticals, skin care products or foods. They may be administered orally, enterally, topically, parenterally, (subcutaneously, intramuscularly, intravenously or by any other route), rectally, vaginally or by any other appropriate route.
  • LA linoleic acid (cis, cis - 9, 12 - octadecadienoic acid)
  • ALA alpha-linolenic acid (cis, cis, cis - 9, 12, 15 -octadecatrienoic acid)
  • GLA ⁇ -linolenic acid (cis,cis,cis - 6,9,12-octadecatrienoic acid)
  • DHA cis, cis, cis, cis, cis, cis, - 4,7, 10, 13,16, 19-docosahexaenoic acid
  • Step (v.) A solution of DCC (HOmg, 0.53mmol) and DMAP (65mg, 0.53mmol) in methylene chloride (5 ml) was added to a solution of the diacylglycerol (prepared as in (ii)) (250mg, 0.41mmol) and ALA (130mg, 0.47mmol) in methylene chloride (10 ml) and the mixture was stirred at room temperature under nitrogen. After 2h the reaction mixture was diluted with hexane (50 ml), filtered, concentrated and purified by flash chromatography (5% ethyl acetate / hexane) to yield the pure triglyceride ⁇ LLG as a colourless oil. (Yield 290mg, 79%).
  • Any one or more of the specified triglycerides added to any appropriate food material such as a spread, drink, candy, cereal, infant food or bakery product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Mycology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention décrit des triglycérides comportant deux ou trois acides gras différents choisis parmi les douze acides gras essentiels, l'acide oléique et autres acides gras contenant 8 à 26 atomes de carbone, et qui sont utilisés dans la nutrition et en médecine.
PCT/GB1996/000828 1995-04-03 1996-04-03 Triglycerides WO1996031457A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
NZ304924A NZ304924A (en) 1995-04-03 1996-04-03 hybridised triglycerides
AU52809/96A AU5280996A (en) 1995-04-03 1996-04-03 Triglycerides
EP96909235A EP0832058A1 (fr) 1995-04-03 1996-04-03 Triglycerides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9506837.5 1995-04-03
GBGB9506837.5A GB9506837D0 (en) 1995-04-03 1995-04-03 Triglycerides

Publications (1)

Publication Number Publication Date
WO1996031457A1 true WO1996031457A1 (fr) 1996-10-10

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ID=10772402

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1996/000828 WO1996031457A1 (fr) 1995-04-03 1996-04-03 Triglycerides

Country Status (6)

Country Link
EP (1) EP0832058A1 (fr)
AU (1) AU5280996A (fr)
CA (1) CA2217258A1 (fr)
GB (1) GB9506837D0 (fr)
NZ (1) NZ304924A (fr)
WO (1) WO1996031457A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19757414A1 (de) * 1997-12-23 1999-07-01 Nutricia Nv Fettmischung
WO2000044360A2 (fr) * 1999-01-27 2000-08-03 Laxdale Limited Medicaments pour le traitement de troubles psychiatriques et cerebraux
US6107334A (en) * 1998-02-23 2000-08-22 Wake Forest University Dietary control of arachidonic acid metabolism
WO2000051576A2 (fr) * 1999-03-03 2000-09-08 Ida Royalty Aps Nouveaux produits pharmaceutiques, supplements alimentaires et compositions cosmetiques, et utilisation de certains melanges pour preparer un medicament ou un supplement alimentaire afin de traiter ou de prevenir une inflammation, des reactions d'hypersensibilite ou une douleur
US6130244A (en) * 1998-02-25 2000-10-10 Abbott Laboratories Product and method to reduce stress induced immune suppression
US6426100B2 (en) 2000-02-17 2002-07-30 The Iams Company Method for improving bone modeling and chondrocyte functioning in growing canines
WO2003030891A1 (fr) * 2001-10-11 2003-04-17 Universitat De Les Illes Balears Utilisation de l'acide hydorxy-oleique et de composes analogues dans la fabrication de medicaments
ES2229935A1 (es) * 2003-10-10 2005-04-16 Universitat De Les Illes Balears Utilizacion del acido hidroxioleico y compuestos analagos del mismo como aditivos alimentarios funcionales.
US7138431B1 (en) 1998-02-23 2006-11-21 Wake Forest University Dietary control of arachidonic acid metabolism
US7439267B2 (en) 2001-01-25 2008-10-21 Pfizer Italia S.R.L. Essential n-3 fatty acids in cardiac insufficiency and heart failure therapy
WO2012131493A1 (fr) * 2011-03-29 2012-10-04 Palupa Medical Ltd. Compositions pour le traitement de troubles neurologiques

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994015464A1 (fr) * 1993-01-15 1994-07-21 Abbott Laboratories Lipides structures
EP0609001A2 (fr) * 1993-01-27 1994-08-03 Scotia Holdings Plc Triglycérides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994015464A1 (fr) * 1993-01-15 1994-07-21 Abbott Laboratories Lipides structures
EP0609001A2 (fr) * 1993-01-27 1994-08-03 Scotia Holdings Plc Triglycérides

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19757414A1 (de) * 1997-12-23 1999-07-01 Nutricia Nv Fettmischung
US7045143B1 (en) 1997-12-23 2006-05-16 N.V. Nutricia Fat blend
US8247449B2 (en) 1998-02-23 2012-08-21 Wake Forest University Methods and compositions for the treatment of asthma
US6107334A (en) * 1998-02-23 2000-08-22 Wake Forest University Dietary control of arachidonic acid metabolism
US7138431B1 (en) 1998-02-23 2006-11-21 Wake Forest University Dietary control of arachidonic acid metabolism
EP1063987A4 (fr) * 1998-02-23 2005-01-12 Univ Wake Forest Regulation dietetique du metabolisme de l'acide arachidonique
US6444700B1 (en) 1998-02-25 2002-09-03 Abbott Laboratories Product and method to reduce stress induced immune suppression
US6130244A (en) * 1998-02-25 2000-10-10 Abbott Laboratories Product and method to reduce stress induced immune suppression
US6255341B1 (en) 1998-02-25 2001-07-03 Abbott Laboratories Product and method reduce stress induced immune suppression
WO2000044360A3 (fr) * 1999-01-27 2000-11-30 Laxdale Ltd Medicaments pour le traitement de troubles psychiatriques et cerebraux
WO2000044360A2 (fr) * 1999-01-27 2000-08-03 Laxdale Limited Medicaments pour le traitement de troubles psychiatriques et cerebraux
WO2000051576A2 (fr) * 1999-03-03 2000-09-08 Ida Royalty Aps Nouveaux produits pharmaceutiques, supplements alimentaires et compositions cosmetiques, et utilisation de certains melanges pour preparer un medicament ou un supplement alimentaire afin de traiter ou de prevenir une inflammation, des reactions d'hypersensibilite ou une douleur
US6638525B2 (en) 1999-03-03 2003-10-28 Eurovita A/S Pharmaceuticals, dietary supplements and cosmetic compositions, and the use of certain mixtures for preparing a medicament or a dietary supplement for the treatment or prevention of inflammation, hypersensitivity reactions or pain
WO2000051576A3 (fr) * 1999-03-03 2001-03-29 Ida Developments As Nouveaux produits pharmaceutiques, supplements alimentaires et compositions cosmetiques, et utilisation de certains melanges pour preparer un medicament ou un supplement alimentaire afin de traiter ou de prevenir une inflammation, des reactions d'hypersensibilite ou une douleur
US6482421B2 (en) 1999-03-03 2002-11-19 Eurovita A/S Pharmaceuticals, dietary supplements and cosmetic compositions, and the use of certain mixtures for preparing a medicament or a dietary supplement for the treatment or prevention of inflammation, hypersensitivity reactions or pain
US6426100B2 (en) 2000-02-17 2002-07-30 The Iams Company Method for improving bone modeling and chondrocyte functioning in growing canines
US7439267B2 (en) 2001-01-25 2008-10-21 Pfizer Italia S.R.L. Essential n-3 fatty acids in cardiac insufficiency and heart failure therapy
US7851507B2 (en) 2001-10-11 2010-12-14 Universitat Des Less Illes Balears Use of hydroxyoleic acid and related compounds in the manufacture of drugs
WO2003030891A1 (fr) * 2001-10-11 2003-04-17 Universitat De Les Illes Balears Utilisation de l'acide hydorxy-oleique et de composes analogues dans la fabrication de medicaments
US8778995B2 (en) 2001-10-11 2014-07-15 Universitat de les Illies Balears Use of hydroxyoleic acid and related compounds in the manufacture of drugs
ES2229935A1 (es) * 2003-10-10 2005-04-16 Universitat De Les Illes Balears Utilizacion del acido hidroxioleico y compuestos analagos del mismo como aditivos alimentarios funcionales.
WO2012131493A1 (fr) * 2011-03-29 2012-10-04 Palupa Medical Ltd. Compositions pour le traitement de troubles neurologiques
EA025232B1 (ru) * 2011-03-29 2016-12-30 Палупа Медикал Лтд. Композиции для лечения нервных расстройств

Also Published As

Publication number Publication date
CA2217258A1 (fr) 1996-10-10
EP0832058A1 (fr) 1998-04-01
GB9506837D0 (en) 1995-05-24
AU5280996A (en) 1996-10-23
NZ304924A (en) 2000-05-26

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