US20070009608A1 - Composition comprising plant and/or fish oils and compounds comprising non-oxidizable fatty acid entities - Google Patents

Composition comprising plant and/or fish oils and compounds comprising non-oxidizable fatty acid entities Download PDF

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US20070009608A1
US20070009608A1 US10/550,129 US55012905A US2007009608A1 US 20070009608 A1 US20070009608 A1 US 20070009608A1 US 55012905 A US55012905 A US 55012905A US 2007009608 A1 US2007009608 A1 US 2007009608A1
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group
atom
fatty acid
carbon atoms
oxygen atom
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Rolf Berge
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Life Science Nutrition AS
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Thia Medica AS
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Priority claimed from NO20043093A external-priority patent/NO324534B1/no
Priority claimed from NO20043091A external-priority patent/NO324533B1/no
Priority claimed from NO20045544A external-priority patent/NO326252B1/no
Application filed by Thia Medica AS filed Critical Thia Medica AS
Assigned to THIA MEDICA AS reassignment THIA MEDICA AS ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BERGE, ROLF
Publication of US20070009608A1 publication Critical patent/US20070009608A1/en
Assigned to LIFE SCIENCE NUTRITION AS reassignment LIFE SCIENCE NUTRITION AS ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: THIA MEDICA AS
Priority to US13/423,884 priority Critical patent/US20120276212A1/en
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Definitions

  • the use of a combination of compounds comprising non ⁇ -oxidizable fatty acid entities and plant oil or fish oil has shown surprising synergistic effects.
  • the present invention concerns a composition prepared from a combination of compounds comprising non ⁇ -oxidizable fatty acid entities and plant oil and/or fish oil.
  • Said composition may be used for the preparation of a pharmaceutical or nutritional composition for the prevention and/or treatment of insulin resistance, obesity, diabetes, fatty liver, hypercholesterolemia, dyslipidemia, atherosclerosis, coronary heart disease, thrombosis, stenosis, secondary stenosis, myocardial infarction, stroke, elevated blood pressure, endothelial dysfunction, procoagulant state, polycystic ovary syndrome, the metabolic syndrome, cancer, inflammatory disorders and proliferate skin disorders.
  • Said composition may also be used as an additive to animal fodder for routine feeding of animals in order to affect their body composition in general and fatty acid composition specifically.
  • non ⁇ -oxidizable fatty acid analogues of the present invention in the treatment and prevention of obesity (NO 2000 5461), diabetes (NO 2000 5462), primary and secondary stenosis (NO 2000 5463), cancer (NO 2002 5930), proliferate skin disorders (NO 2003 1080), inflammatory and autoimmune disorders (NO 2003 2054).
  • the present inventors have now shown that the use of a combination of compounds comprising non ⁇ -oxidizable fatty acid entities with plant oil or fish oil has synergistic beneficial biological effects.
  • the inventors show that the combination of non ⁇ -oxidizable fatty acid entities with plant oil or fish oil lowers the concentration of plasma cholesterol, triglycerides and phospholipids, and increase fatty acyl CoA oxidase activity.
  • the inventors describe how non ⁇ -oxidizable fatty acid entities and plant or fish oils can be directly added to animal feed.
  • the feed is digestible, and has shown surprising effects on the fatty acid composition of the animals.
  • Lipid is a cheaper energy source than protein, and farmers want the animals to obtain as much energy as possible from lipid in the diet (by increased lipid oxidation) and as little as possible from protein. Animals also tend to grow more rapidly when their feed contains a large proportion of fats, which is generally a desirable feature.
  • the invention is here exemplified by reference to fish farming and fish, specifically Atlantic salmon.
  • TTA 3-thia fatty acid tetradecylthioacetic acid
  • the present invention relates to the use of a preparation comprising a combination of:
  • R′′ is a linear or branched alkyl group, saturated or unsaturated, optionally substituted, wherein the main chain of said R′ contains from 13 to 23 carbon atoms and optionally one or more heterogroups selected from the group comprising an oxygen atom a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group, a SO group and a SO 2 group; and R′′ is a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms; and/or
  • At least one of R1, R2 or R3 is an alkyl.
  • At least one of R1, R2 or R3 is an alkene.
  • At least one of R1, R2 or R3 is an alkyne.
  • At least one of R1, R2 or R3 is tetradecylthioacetic acid.
  • At least one of R1, R2 or R3 is tetradecylselenoacetic acid.
  • Preferred embodiments of the compounds according to the invention are non ⁇ -oxidizable fatty acids.
  • X is a sulphur atom or a selenium atom.
  • Preferred embodiments of the compounds according to the invention are tetradecylthioacetic acid (TTA), tetradecylselenoacetic acid and 3-Thia-15-heptadecyne.
  • n is 0 or 1.
  • said compound is a phospholipid, wherein said phospholipid is selected from the group comprising phosphatidyl serine, phosphatidyl choline, phosphatidyl ethanolamine phosphatidyl inositol, phosphatidyl glycerol, diphosphatidyl glycerol.
  • said compound is a triacylglycerol.
  • said compound is a diacylglycerol.
  • said compound is a monoacylglycerol.
  • said compound is the phosphatidylcholine (PC) derivative 1,2-ditetradecylthioacetoyl-sn-glycero-3-phosphocholine.
  • PC phosphatidylcholine
  • said compound is the phosphatidylethanolamine (PE) derivative 1,2-ditetradecylthioacetoyl-sn-glycero-3-phosphoethanolamine.
  • PE phosphatidylethanolamine
  • Preferred embodiments of the compounds according to the invention are mono-, di- or tri-acylglycerides.
  • Preferred embodiments of the compounds according to the invention are tri-acylglycerides comprising tetradecylthioacetic acid (TTA).
  • TTA tetradecylthioacetic acid
  • A1 and A3 both represent an oxygen atom, while A2 represent a sulphur atom or an N—R4 group in which R4 is a hydrogen atom or a linear or branched alkyl group, saturated or unsaturated, optionally substituted, containing from 1 to 5 carbon atoms.
  • the compounds according to the invention are analogues of naturally occurring compounds, and as such are recognized by the same systems which process the natural compounds, including the enzymes that ⁇ - and in some cases ⁇ -oxidize natural long chain fatty acids.
  • the analogues differ from their naturally occurring counterparts in that they cannot be completely oxidized in this manner.
  • the compounds according to the invention may be non ⁇ -oxidizable fatty acid analogues, as represented by the formula R′′CCO—(CH 2 ) 2n+1 —X—R′.
  • said compounds may also be more complex structures derived from one or more of said non ⁇ -oxidizable fatty acid analogues, as represented by the general formulas (I) or (II).
  • These compounds are analogues of naturally occurring mono-, di-, and triacylglycerols, or phospholipids including phosphatidyl serine, phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl inositol, phosphatidyl glycerol, and diphosphatidyl glycerol.
  • Said compounds may also comprise a substitution in the glycerol backbone, as shown in formula (II). Said substitution of the oxygen(s) is achieved by replacing the oxygen(s) with sulphur or a nitrogen containing group. This may block hydrolysis before uptake by the intestines, thus increasing the bioavailability of the compounds.
  • the above complex structures derived from one or more of said non ⁇ -oxidizable fatty acid entities have their effect because the fatty acid analogues they comprise are not capable of being fully ⁇ -oxidized.
  • Said complex structures may have an effect as complete structures, and as naturally resulting degradation products comprising the fatty acid analogues. Because the compounds are not able to be fully ⁇ -oxidized, they will build up, and this triggers an increase in the ⁇ -oxidation of naturally occurring fatty acids. Many of the effects of the compounds according to the invention are due to this increase in ⁇ -oxidation.
  • ⁇ -oxidation a fatty acid is enzymatically oxidized cleaved between carbons 2 and 3 (when counting from the carboxylic end of the fatty acid), resulting in the removal of the two carbon atoms on either side of the oxidation site as acetic acid. This step is then repeated on the now two carbons shorter fatty acid, and repeated again until the fatty acid is fully oxidized.
  • ⁇ -oxidation is the usual way in which the majority of fatty acids are catabolized in vivo.
  • the ⁇ -oxidation blocking by the compounds according to the invention is achieved by the insertion of a non-oxidizable group in the X position in the formula of the present invention. Because the mechanism for ⁇ -oxidation is well known, X is defined as S, O, SO, SO 2 , CH 2 or Se.
  • the compounds may contain more than one block, i.e. in addition to X, R′ may optionally comprise one or more heterogroups selected from the group comprising an oxygen atom, a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group, a SO group and a SO 2 group.
  • R′ may optionally comprise one or more heterogroups selected from the group comprising an oxygen atom, a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group, a SO group and a SO 2 group.
  • R′ may optionally comprise one or more heterogroups selected from the group comprising an oxygen atom, a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group, a SO group and a SO 2 group.
  • one may insert two or three sulphurs as X to induce a change in the degradation of the fatty acid and thus a modulated effect
  • n is an integer of 0 to 11.
  • fatty acids which normally undergo ⁇ -oxidation are usually 14 to 24 carbon atoms long, and this length is therefore most ideal for undergoing enzymatic ⁇ -oxidation.
  • the ranges of n and R′ are thus given so that the fatty acid analogues will cover this range.
  • option ii) of formulas (I) and (II) and define R to have 1 to 25 carbon groups
  • option i) of formula (II) define the alkyl group to contain from 1 to 23 carbon atoms, to be analogous to naturally occurring compounds.
  • the total number of carbon atoms in the fatty acid backbone is preferably between 8 and 30, most preferably between 12 and 26. This size range is also desirable for the uptake and transport through cell membranes of the fatty acid analogues of We present invention.
  • fatty acid analogues and other compounds represented by the general formulas (I) and (II), (which comprise said fatty acid analogue(s),) which block ⁇ -oxidation at different distances from the carboxylic end of the analogues as the compounds of the present invention all do indeed block ⁇ -oxidation, even if the effect thereof can be modulated.
  • This modulation will after all differ under wearying conditions; in different tissues, with wearying dosages, and by changing the fatty acid analogue so that it is not so easily broken down, as will be described next.
  • fatty acid analogues as described with a block in the X position cannot undergo ⁇ -oxidation, they may still undergo ⁇ -oxidation.
  • This is a much less common and slower biological process, which oxidizes the fatty acid not from the carboxylic end, but rather from the methyl/hydrophobic head group, here termed R′.
  • R′ methyl/hydrophobic head group
  • the carbon atom at the ⁇ -end of the fatty acid is hydroxylated by a member of the cytochrome P450 enzyme family.
  • This hydroxylated fatty acid is then converted into an aldehyde by an alcohol dehydrogenase, and subsequently this aldehyde is converted into a carboxyl group by an aldehyde dehydrogenase.
  • the final product of the pathway is a dicarboxylic fatty acid, which can be degraded further by ⁇ -oxidation from the ⁇ -end.
  • ⁇ -oxidation is believed to be the main pathway for degradation of the fatty acid analogues as described with a block in the X position.
  • R′ was changed to block ⁇ -oxidation, by introducing a triple bond at the methyl end of the fatty acid analogue.
  • This is important for the use of the fatty acid analogues in pharmaceutical preparation, as it may potentiate the effects of the ⁇ -oxidizable fatty acid analogues by further slowing down their breakdown.
  • R′ methyl/hydrophobic head group end of the molecule
  • R′ may be substituted in one or several positions with heterogroups selected from the group comprising an oxygen atom, a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group, a SO group and a SO 2 group.
  • R′ may also be substituted with one or more compounds selected from the group comprising fluoride, chloride, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 2 -C 5 acyloxy or C 1 -C 4 alkyl.
  • the compounds according to the present invention are either fatty acids analogous to naturally occurring fatty acids, which are not capable of being ⁇ -oxidized, or naturally occurring lipids comprising said fatty acid analogues.
  • the fatty acid analogues show a strong preference for being incorporated into phospholipids.
  • a complex by including a fatty acid(s) which are not capable of being ⁇ -oxidized into a triacylglycerol, Such compounds are encompassed by formulas (I) and (II). If such a triacylglycerol was taken orally, for instance in an animal feed product, it would probably be transported like any triacylglycerol, from the small intestine in chylomicrons and from the liver in the blood in lipoproteins to be stored in the adipose tissue or used by muscles, heart or the liver, by hydrolyzes of the triacylglycerol into glycerol and 3 free fatty acids. The free fatty acids would at this point be the parent compound of the present invention, and not a complex anymore.
  • glycerophospholipid derivatives of the fatty acids of the present invention includes, but are not limited to, phosphatidyl cholines, phosphatidyl ethanolamines, phosphatidyl inositols, phosphatidyl serines and phosphatidyl glycerols.
  • Another esterification of fatty acids found in vivo which could be easily used to make a complex for a compound of the present invention would be to make the alcohol or polyalcohol corresponding to the fatty acid, for example one could make a sphingolipid derivative such as ceramide or sphingomyelin by making the corresponding amino alcohol.
  • a sphingolipid derivative such as ceramide or sphingomyelin
  • glycerophospholipid complexes such complexes would be very water insoluble and less hydrophilic.
  • polar complexes of the present invention may be, but are not limited to, lysophospholipids, phosphatidic acis, alkoxy compounds, glycerocarbohydrates, gangliosiedes, and cerebrosides.
  • the fatty acid ⁇ -oxidation pathway is the main pathway for the metabolism of fats.
  • the initial and rate limiting reaction is carried out in the peroxisomes of the liver by acyl-CoA oxidase.
  • Acyl-CoA oxidase catalyze the dehydrogenation of acyl-CoA thioesters to the corresponding tans-2-enoyl CoA.
  • a fatty acid analogue according to formula (I); tetradecylthioacetic acid (TTA), has been used previously by the present inventors to test the various biological effects of the fatty acids. In the current invention, its effect on acyl-CoA oxidase was tested, as well as the effect of various plant oils and fish oil, alone or in concurrence.
  • TTA alone showed effected a large increase in this enzyme activity compared to the negative control.
  • the plant and fish oils alone exhibited a very small increase in acyl-CoA oxidase activity compared to the negative control.
  • Sunflower oil did not increase the activity of TTA when administered together. This is what one would expect, that the acyl-CoA oxidase activity of TTA with oils would stay the same as without added oils.
  • Fish and olive oil showed a slight potentiation of the increase in acyl-CoA oxidase activity by TTA. Soy oil without TTA had negligible effects on —CoA oxidase activity, but combined with TTA it exhibited a 60% increase when compared to the effects of TTA alone. This potentiating of TTA as an acyl-CoA oxidase activator by soy oil is quite unexpected.
  • TTA lowered the cholesterol level more than any of the plant or fish oils alone.
  • Sunflower oil or fish oil without TTA lowered the cholesterol levels somewhat, with TTA the cholesterol levels were lowered beyond that of TTA alone.
  • Olive and soy oil actually increased the cholesterol levels on their own, but, quite unexpectedly, when added to TTA these oils improved on TTAs ability to lower cholesterol. This TTA potentiating effect was greatest with soy oil, which reduced the cholesterol level with 60% when compared with TTA alone.
  • TTA has been shown to reduce the plasma triacylglycerol level by increasing the number of mitochondria and stimulating mitochondrial ⁇ -oxidation of normal saturated and unsaturated fatty acids to ketone bodies (Froyland L et al. (1997) J Lipid Res 38:1851-1858).
  • this effect was ether unexpectedly potentiated by the addition of plant and fish oils.
  • Olive, sunflower and fish oil all lowered the triacylglycerol levels on their own, sunflower and fish oil even more so than TTA alone, and further potentiated the cholesterol lowering effect of TTA beyond that seen for either the oils or TTA on its own. Soy oil showed the most spectacular results; on it's own it actually increased cholesterol levels by 15% compared to the control, but quite unexpectedly it potentiated TTAs cholesterol lowering effect by 130%.
  • example 2.1 fish feed was composed from coating common feed pellets with fish oil including TTA. This feed was then used in example 2.2 as the food supply for Atlantic salmon, and the presence of TTA had beneficial effects on the thus produced compared to fish fed equivalent feed without TTA (examples 2.3 and 2.4).
  • the common feed pellets used comprised mostly fish meal, some wheat and a vitamin and mineral additive.
  • the oil used for the coating of the pellets was of marine origin, from capelin, and had various amounts of TTA mixed in.
  • Table 1 describes the formulation and chemical composition of the diets.
  • the origin of the protein (fish meal) or carbohydrates (wheat) is in itself not so important, the important part is that this is a common feed, well suited for the test species (in this example Atlantic salmon), which upon addition of TTA exhibits beneficial effects.
  • TTA administered together with protein has an added beneficial effect as compared to TTA alone.
  • the source of fat chosen for the diet might be more important, as TTA herein has been shown to have surprising synergistic effects with oils, especially of marine origin.
  • this common feed is high in fats and protein and low in carbohydrates probably increased the beneficial effects of TTA over TTA being administered alone, or in a diet with more carbohydrates.
  • the fermented soy protein material is resulting from a fermentation of soy beans. It comprises modified and unmodified soy proteins and isoflavones, as well as other soy constituents.
  • a preferred embodiment of the invention uses the fermented soy protein material Gendaxin®.
  • Table 2 describes the fatty acid composition of the diets. There were only minor differences in the fatty acid composition of the diets (all contained nearly 100% fish oil), the percentage of n-3 fatty acids (FA) was almost equal. Diets supplemented with TTA, however, led to substantial changes in the percentage of n-3 fatty acid composition of the phospholipids (PL), triacylglycerols (TAG) and free fatty acids (FFA) of gills, heart and liver of Atlantic salmon. Administration of TTA during the 8 weeks also resulted in a decreased percentage of saturated FAs in almost all the lipids fractions. The percentage of the n-3 FAs, especially DHA, increased in the gills and heart, as can be seen in example 2.3.
  • Atlantic salmon fed diets containing TTA grew at a slower rate than fish fed the control diet.
  • the body lipid level in fish fed the diets supplemented with TTA was significantly lower than it was in fish fed the control diet
  • Old fish may experience arterial sclerosis and resulting health problems just like humans, and a lowering of lipids will have a beneficial effect on this.
  • lean meat as obtained by the method of the present invention, is considered beneficial in most animal species reared for consumption.
  • the effect of lowering the total lipid levels is in itself advantageous.
  • the specific changes in fatty acid composition are particularly positive. It is widely recognized that consuming less saturated fatty acids is healthy, and an increased consumption of n-3 has been associated with a whole host of health benefits, from reducing the chance of heart diseases to anti-inflammatory effects and even smarter babies.
  • animal products obtained from animals fed the feed of the present invention may also have beneficial effects.
  • fish oil thus obtained have an advantageous nutritional composition when compared to oil from fish fed commercial diets.
  • Other products, such as fish skins, may also have beneficial effects seeing as the whole body composition is improved.
  • the level of fatty acids in the blood is normally determined by the relative rates of lipolysis and esterification in adipose tissue, and the uptake of fatty acids in the muscles. In the muscles, fatty acids inhibit glucose uptake and oxidation. Increased levels of fatty acids and triacylglycerol in the blood and muscles therefore correlate with obesity and insulin resistance, as well as a reduced ability to metabolize glucose (Olefsky J M (2000) J Clin Invest 106:467-472; Guerre-Millo M et al. (2000) J Biol Chem 275:16638-16642).
  • Stimulation of fatty acid oxidation and decreased plasma fatty acid concentration by non ⁇ -oxidizable fatty acid entities and plant and/or fish oils can therefore prevent and treat insulin resistance and diseases caused thereby (Shulman G I (2000) J Clin Invest 106(2):171-176).
  • TTA has been found to completely prevent high-fat diet induced insulin resistance and adiposity, and reduce adiposity, hyperglycaemia and insulin sensitivity in obese rats (Madsen M et al. (2002) J Lipid Res 43(5):742-50).
  • TTA is potentiated by fish and plant oils in treating related diseases and disorders including elevated blood pressure, increased lipid and cholesterol levels, endothelial dysfunction, procoagulant state, polycystic ovary syndrome and the metabolic syndrome.
  • the peroxisome proliferator-activated receptor (PPAR) family are pleiotropic regulators of cellular functions such as cellular proliferation, differentiation and lipid homeostasis (Ye J M et al. (2001) Diabetes 50:411-417).
  • the PPAR family is comprised of three subtypes; PPAR ⁇ , PPAR ⁇ , and PPAR ⁇ .
  • TTA is a potent ligand of PPAR ⁇ (Forman B M, Chen J, Evans R M (1997) Proc Natl Acad Sci 94:4312-4317; Gottlich M et al. (1993) Biochem Pharmacol 46:2177-2184; Berge R K et al.
  • PPAR ligands affect proliferation of various cancer cell lines. TTA in particular has been found to reduce proliferation of many cancer cell lines (Berge K et al. (2001) Carcinogenesis 22:1747-1755; Abdi-Dezfuli F et al. (1997) Breast Cancer Res Treat 45:229-239; Tronstad K J et al. (2001) Biochem Pharmacol 61:639-649; Tronstad K J et al. (2001) Lipids 36:305-313). This reduction is related to reduction in triacylglycerol levels (Tronstad K J et al.
  • TTA may be used for the prevention and/or treatment of cancer including inhibition of: primary and secondary neoplasms, the growth of tumours, invasion of a primary tumour into connective tissue, and formation of secondary tumours (NO 2002 5930).
  • PPAR agonists and poly unsaturated fatty acids modulate the inflammatory response.
  • TTA modulate inflammatory response by depressing the release of inflammatory cytokine interleukin-2 and suppressing PHA stimulated proliferation of peripheral mononuclear cells (Aukrust P et al. (2003) Eur J Clin Invest 33(5):426-33).
  • the modulation of cytokine by TTA may be PPAR mediated or through altered prostaglandin levels or by modification of lipid mediated signal transduction, the latter which also is the proposed mechanism of action for poly unsaturated fatty acids, as those found in plant and fish oils.
  • plant oil and/or fish oil in combination with non ⁇ -oxidizable fatty acid entities will potentiate the effect of the fatty acid analogues on inflammatory disorders including immune mediated disorders such as rheumatoid arthritis, systemic vasculitis, systemic lupus erythematosus, systemic sclerosis, dermatomyositis, polymyositis, various autoimmune endocrine disorders (e.g. thyroiditis and adrenalitis), various immune mediated neurological disorders (e.g. multiple sclerosis and myastenia gravis), various cardiovascular disorders (e.g.
  • immune mediated disorders such as rheumatoid arthritis, systemic vasculitis, systemic lupus erythematosus, systemic sclerosis, dermatomyositis, polymyositis, various autoimmune endocrine disorders (e.g. thyroiditis and adrenalitis), various immune mediated neurological disorders (e.g. multiple sclerosis and my
  • myocarditis congestive heart failure, arteriosclerosis and stable and unstable angina, and Wegener's granulomatosis
  • inflammatory bowel diseases Crohn's disease, congestive heart failure, arteriosclerosis and stable and unstable angina, and Wegener's granulomatosis
  • inflammatory bowel diseases Crohn's disease, rhepatosis, rhepatosis, rhepatosis, fibrosis of the liver, and acute and chronic allograft rejection after organ transplantation, as well as proliferate skin disorders like psoriasis, atopic dermatitis, non-specific dermatitis, primary irritant contact-dermatitis, allergic contact-dermatitis, lamellar ichthyosis, epidermolytic hyperkeratoses, pre-malign sun-induced keratoses, and seborrhoea, and diseases that have an inflammatory component such as e.g. Alzheimer's disease or impaired/improvable cognitive
  • FIG. 1 shows that the increase in fatty acyl-CoA activity by TTA is potentated by soy oil, olive oil and fish oil.
  • FIG. 2 shows that the phospholipids lowering effect of TTA is potentated by sunflower oil, soy oil and fish oil.
  • FIG. 3 shows that the cholesterol lowering effect of TTA is potentated by olive oil, sunflower oil, soy oil and fish oil.
  • FIG. 4 shows that the triacylglycerol lowering effects of TTA is potentated by olive oil, sunflower oil, soy oil and fish oil.
  • mammals include mammals such as humans and farm (agricultural) animals, especially the animals of economic importance such as gallinaceous birds, bovine, ovine caprine and porcine mammals, especially those that produce products suitable for the human consumption, such as meat, eggs and milk.
  • the term is intended to include fish and shellfish, such as salmon, cod, Tilapia, clams, oysters, lobster or crabs.
  • the term also includes domestic is such as dogs and cats.
  • animal feed refers to food for animals (as defined above).
  • Animal feed usually comprise appropriate amounts of fats, proteins, carbohydrates, vitamins and minerals necessary for the sustenance of the intended animal recipient, and may comprise additional components for the improvement of taste, texture, colour, smell, stability, storage life etc, or antibiotics or other components added for the benefit of the health of the animal.
  • the animal feed is preferably but not necessary dry matter, most preferably a pellet material.
  • animal feed is also intended to include nutritional compositions, veterinary compositions, and/or functional food products for animal consumption.
  • meat refers to flesh from any animal as defined above.
  • protein containing flesh from mammals, birds, fish and shellfish is all referred to as meat.
  • meat product refers to any product produced from meat as defined above.
  • oils of plant or marine origin including but not limited to fatty or fixed oils as well as essential or volatile oils, and any combination thereof. They do not necessarily need to be in liquid form.
  • Sunflower oil which was used in the present invention, is really oil from the sunflower seed, not the flower itself.
  • This term include all oils of a marine origin.
  • This term is meant to include any ingestible material, including but not restricted to nutritional supplements, functional foods, herbal supplements etc. for human or animal consumption.
  • the term also includes food products for human consumption and animal fodder, wherein the composition of the present invention is an additive, and not the main ingredient. This especially concerns animal fodder, where any fodder can be supplemented with the composition of the present invention, to attain the biological effects thereof.
  • treatment refers to a reduction of the severity of the disease.
  • prevention refers to the preventing of a given disease, i.e. a compound of the present invention is administered prior to the onset of the condition.
  • the compounds of the present invention can be used as prophylactic agents or as ingredients in a nutritional composition in order to prevent the risk or onset of a given disease.
  • This term is meant to include any ingestible material, including but not restricted to nutritional supplements, functional foods, herbal supplements etc. for human or animal consumption.
  • the term also includes food products for human consumption and animal fodder, wherein the composition of the present invention is an additive, and not the main ingredient. This especially concerns animal fodder, where any fodder can be supplemented with the composition of the present invention, to attain the biological effects thereof.
  • the compounds of the present invention may be administered directly to the animal by any suitable technique, including parenterally, intransally, orally, or by absorption through the skin. They can be administered locally or systemically.
  • the specific route of administration of each agent will depend, e.g., on the medical history of the recipient human or animal.
  • parenteral administration examples include subcutaneous, intramuscular, intravenous, intra-arterial, and intra-peritoneal administration
  • the total pharmaceutically effective amount of each of the non ⁇ -oxidizable fatty acid entities administered parenterally per dose will preferably be in the range of about 1 mg/kg/day to 200 mg/kg/day of patient body weight for humans, although, as noted above, this will be subject to a great deal of therapeutic discretion.
  • a dose of 5-50 mg/kg/day is most preferable.
  • a dose of 1-300 mg/kg/day of oil is preferable, and a dose of 10-150 mg/kg/day is most preferable.
  • the compounds of the present invention are each typically administered by 1-4 injections per day or by continuous subcutaneous infusions, for example, using a mini-pump.
  • An intravenous bag solution may also be employed.
  • the key factor in selecting an appropriate dose is the result obtained, as measured by decreases in total body weight or ratio of fat to lean mass, or by other criteria for measuring control or prevention of obesity or prevention of obesity-related conditions, as are deemed appropriate by the practitioner.
  • the compounds of the present invention are formulated generally by mixing each at the desired degree of purity, in a unit dosage injectable form (solution, suspension, or emulsion), with a pharmaceutically acceptable carrier, i.e., one that is non-toxic to recipients at the dosages and concentrations employed and is compatible with other ingredients of the formulation.
  • a pharmaceutically acceptable carrier i.e., one that is non-toxic to recipients at the dosages and concentrations employed and is compatible with other ingredients of the formulation.
  • the formulations are prepared by contacting the compounds of the present invention each uniformly and intimately with liquid carriers or finely divided solid carriers or both. Then, if necessary, the product is shaped into the desired formulation.
  • the carrier is a parenteral carrier, more preferably a solution that is isotonic with the blood of the recipient. Examples of such carrier vehicles include water, saline, Ringer's solution, and dextrose solution. Non-aqueous vehicles such as fixed oils and ethyl oleate are also useful herein, as well as liposomes.
  • the carrier may suitably contain minor amounts of additives such as substances that enhance isotonicity and chemical stability.
  • additives such as substances that enhance isotonicity and chemical stability.
  • Such materials are non-toxic to recipients at the dosages and concentrations employed, and include buffers such as phosphate, citrate, succinate, acetic acid, and other organic acids or their salts; antioxidants such as ascorbic acid; immunoglobulins; hydrophilic polymers such as polyvinylpyrrolidone; amino acids, such as glycine, glutamic acid, aspartic acid, or arginine; monosaccharides, disaccharides, and other carbohydrates including cellulose or its derivatives, glucose, mannose, or dextrins; chelating agents such as EDTA; sugar alcohols such as mannitol or sorbitol; counterions such as sodium, and/or non-ionic surfactants such as polysorbates, poloxamers, or PEG.
  • buffers such as phosphate, citrate
  • compositions such carrier material as, for example, water, gelatine, gums, lactose, starches, magnesium-stearate, talc, oils, polyalkene glycol, petroleum jelly and the like may be used.
  • Such pharmaceutical preparation may be in unit dosage form and may additionally contain other therapeutically valuable substances or conventional pharmaceutical adjuvants such as preservatives, stabilising agents, emulsifiers, buffers and the like.
  • the pharmaceutical preparations may be in conventional liquid forms such as tablets, capsules, dragees, ampoules and the like, in conventional dosage forms, such as dry ampoules, and as suppositories and the like.
  • the compounds of the present invention i.e. the compounds comprising ⁇ -oxidizable fatty acid analogue and plant and/or fish oils
  • the plant and/or fish oils can be a substantial part of the fodder, and thus have a nutritional value as well as potentiating the non ⁇ -oxidizable fatty acid analogues.
  • Oil of the present invention can comprise up to all of the fat in a nutritional composition.
  • the amount of non ⁇ -oxidizable fatty acid analogue can be up to 10 times that in products for human consumption, that is, up to 2 g/kg/day of animal body weight.
  • Such animal fodder may be used for routine feeding of animals.
  • An animal feed composition may also comprise fermented soy protein material. Fermented soy protein material is especially useful as a functional protein in food products, particularly when used as a substitute for natural plasma in animal feeds and in pet foods.
  • An animal feed composition may also comprise additional ingredients such as fats, sugars, salt, flavourings, minerals, etc.
  • the product may then be formed into chunks resembling natural meat chunks in appearance and texture.
  • the product of the invention has the further advantages that this is readily formulated to contain necessary nutrients, is easily digested by the animals and is palatable to the animals.
  • Chemicals were obtained from common commercial sources and were of reagent grade.
  • the fish oil was obtained from Hordafor, while the plant oils were obtained from Mills.
  • Carboxymethylcellulose (CMC) was used as a control (negative).
  • mice Male Wistar rats weighing from 250 to 358 g, were bought from AnLab Ltd. (Prahg, The Check Republic), and were kept in wire cages in a temperature of 22+/ ⁇ 1° C. and light controlled (light from 7 am to 7 pm) room. There were no restrictions put on food and water intake. Three rats were kept in each cage. Increase in weight and food intake was monitored daily.
  • the rats were fed a standard Chow ST1 diet (from Vela Prahg, The Check Republic).
  • the rats were anaesthetized with a 1:1 mixture of HypnormTM (fentanyl citrate 0.315 mg/ml and fluanisone 10 mg/ml, Janssen Animal Health) and Dormicum® (midazolam 5 mg/ml, F. Hoffmann-La Roche) injected subcutaneously. Blood was drawn directly from the heart using a heparin rinsed syringe. The liver was immediately removed, weighed and divided into two parts, which were immediately chilled on ice or frozen in liquid nitrogen, respectively. Plasma and tissues were stored at ⁇ 80° until analysis. The protocol was approved by the Norwegian State Board of Biological Experiments with Living Animals.
  • Livers from the rats were homogenised individually in ice-cold sucrose-solution (0.25 mol/L sucrose in 10 mmol/L HEPES buffer pH 7.4 and 1 mmol/L EDTA) using a Potter-Elvehjem homogeniser. Subcellular fractionation of the livers was performed as previously described Merge R K et al. (1984) Eur J Biochem 141: 637-44). The procedure was performed at 0-4° C., and the fractions were stored at ⁇ 80° C. Protein was assayed with the BioRad protein assay kit using bovine serum albumin as the standard.
  • Fatty acyl-CoA oxidase activity was measured in the peroxisomal liver fraction as previously described (Small G M, Burdett K, Connock M J (1985) Biochem J 227: 205-10). The results were given as fatty acyl-CoA oxidase activity per total protein, baseline activity (activity of control) was subtracted, and the data which is presented in FIG. 1 were normalized to the activity of TTA.
  • Plasma and liver lipids were measured enzymatically on the Technicon Axon system (Miles, Tarrytown, N.Y.) using the Triglyceride kit from Bayer, Total cholesterol (Bayer, Tarrytown, N.Y.), and the PAP150 kit for choline containing phospholipids from bioMerieux. The results were given per total protein, and the data which is presented in FIGS. 2-4 were normalized to the activity of the positive control (no added TTA or oils; i.e. “normal” levels).
  • the experimental fishmeal-based diets were provided by EWOS and contained 0.01% Y 2 O 3 as an inert marker for digestibility determination (3 mm pellets).
  • Table 1 shows the formulations and chemical compositions of the three diets. All the three diets were produced from one feed mix. The different diets were obtained by coating the common feed pellet with the different oils and mixtures. The diets contained either fish oil (capelin oil) (Control), fish oil supplemented with 0.5% TTA (0.5% TTA) or fish oil supplemented with 1.5% TTA (1.5% TTA).
  • fish oil Control
  • fish oil added 1.5% TTA (1.5% TTA).
  • TTA 1.5%
  • TTA Formulation (% of total) Fish meal, LT 67.8 67.8 67.8 Capelin oil a 21.3 21 20.7 TTA 0.1 0.3 Wheat 10.4 10.4 10.4 Astax b -Cantax c 0.06 0.06 0.06 Mineral/Vitamin premix 0.49 0.49 0.49 Yttrium oxide 0.01 0.01 0.01 Chemical composition Dry matter (%) 97.1 96.1 93.8 Protein (%) 51.9 51.4 49.7 Fat (%) 26.9 26.7 26.7 Ash (%) 10.8 10.4 10 Energy (MJ/kg) 23.8 23.7 23.2 a Capelin oil, Norsildmel, Norway. b Asta, BASF, lucanthin red. c Canta, lucanthin pink.
  • the fatty acid composition of the diets clearly reflected that of the fish oil used (capelin oil) (Table 2).
  • the capelin oil contained relatively high levels of the monounsaturated FAs and was also rich in the long-chain n-3 FAs, 20:5 n-3 (EPA) and 22:6 n-3 (DHA).
  • the feed however, contained a significant amount of fish meal, which contained n-3 FAs, ensuring that the levels of these FA in the diet where higher than those in the added oil.
  • the trial was conducted at AKVAFORSK Research Station, Sunndals ⁇ ra, Norway.
  • Atlantic salmon Salmon salar
  • the tans were supplied with seawater with a constant temperature of 12° C.
  • the fish were acclimatised to the temperature and fed a commercial feed for two weeks before the start of the trial.
  • the growth trial consisted of one period of 8 weeks.
  • the diets were as described above in table 2, containing either fish oil (capelin oil) (Control), fish oil supplemented with 0.5% TTA (0.5% TTA) or fish oil supplemented with 1.5% TTA (1.5% TTA).
  • the tree diets were randomly assigned to triplicate tanks. The feed was distributed by electrically driven disc-feeders (Akva,er AS, Sunndals ⁇ ra). The tanks were designed such that waste feed was collected from the effluent water in wire mesh boxes. Wasted feed was collected, and this allowed the weight of feed consumed to be calculated.
  • Gendaxin containing diets were used in a separate experiment, but the design thereof was the same as described above.
  • the fish were fasted for 2 days before the initial sampling.
  • Six fish from each tank were anesthetised in MS-222 at the beginning and at the end of the experiment, and the mean weight and mean length were determined. These six fish were killed by a blow to the head and the abdomen cut open. Samples of liver, heart gills and kidney were immediately frozen in liquid nitrogen and stored at ⁇ 80° C. These samples were subsequently used for the analysis of fatty acid composition. A further five fish per tank were anaesthetised and killed. These fish were used for determination of the composition of the whole body.
  • the second gill arch was removed from anaesthetised fish and rinsed in ice-cold SEI buffer (150 mM sucrose, 10 nM EDTA, 50 mM imidazole, pH 7.3) and immediately frozen in liquid nitrogen. Gill tissues were stored at ⁇ 80° C. Livers were homogenized in ice old sucrose medium.
  • Acetic acid, chloroform, petroleum ether and methanol were all obtained from Merck (Darmstadt, Germany). Benzene was obtained from Rathburn Chemicals Ltd. (Walkerburn, Scotland) and 2′,7′-dichlorofluorescein from Sigma Chemical Co. (St. Louis, Mo., USA). Methanolic HCl and 2,2-dimethoxypropane was purchased from Supelco Inc. (Bellfonte, Pa., USA). Glass-baked silica gel K6 plates were obtained from Whatman International Ltd. (Maidstone, England).
  • Total lipids were extracted from homogenised gills, liver and heart using the method described by Folch ( J Biol Chem 1957 226:497-509).
  • the chloroform-methanol phases from the gills were dried under nitrogen and dissolved in hexane.
  • Phospholipids (PL), triacylglycerol (TAG) and See fatty acids (FFA) were separated by thin-layer chromatography (TLC) using a mixture of petroleum ether, diethyl ether and acetic acid (113:20:2 by volume) as the mobile phase.
  • TLC thin-layer chromatography
  • the lipids were visualised by spraying the TLC plates with 0.2% (w/v) 2′,7′-dichlorofluorescein in methanol and they were identified by comparison with known standards under UV-light.
  • the methyl esters of FAs were separated in a gas chromatograph (Perkin-Elmer Auto system GC equipped with an injector, programmable split/splitless injector) with a CP wax 52 column (with lengh 25 m, internal diameter 0.25 mm and tickness of the film 0.2 ⁇ m), flame ionisation detector and 1022 data system.
  • the carrier gas was He, and the injector and detector temperatures were 280° C.
  • the oven temperature was raised from 50° C. to 180° C. at the rate of 10° C. min ⁇ 1 , and then raised to 240° C. at the rate of 0.7° C. min ⁇ 1 .
  • the relative quantity of each fatty acid present was determined by measuring the area under the peak corresponding to that fatty acid.
  • Apparent digestibility coefficients were calculated as described by Austreng ( Aquaculture, 1978 13:265-272).
  • TTA was incorporated into the PL fraction of the gills (0.8%) and heart (0.7%) of the Atlantic salmon fed the 1.5% TTA diet.
  • TTA was also incorporated into the TG and the FFA fractions of the gills (Table 7). Traces of TTA and its ⁇ 9 desaturase products were incorporated into the liver lipids, while no ⁇ 9 desaturase products from TTA were recovered in lipids from heart and gills.
  • n-3 FAs in the liver, gills and heart also depended on the diet given to the fish.
  • the percentage of EPA+DHA was significantly higher in fish fed the 1.5% TTA diet than in control fish, in all the lipid fractions of the gills and heart.
  • TTA led to only a moderate increase in the percentage of DHA and a slightly reduced percentage of EPA.
  • the percentage of palmitic acid (16:0) and the sum of all saturated FAs were significantly lower in the PL fraction of the gills, heart and liver of fish fed the 1.5% TTA diet than they were in fish fed the control diet (Tables 7, 8, 9).
  • the quantity of each fatty acid is given as percentage of the total fatty acids (FA).
  • the quantity of each fatty add is given as percentage of the total fatty acids (FA).
  • Gendaxin was obtained from Aximed, Bergen, Norway.
  • One capsule of Gendaxin® contains 35 mg isoflavones, inter alia 10 mg Genistein and 15 mg Daidzein.
  • Plasma lipids were measured enzymatically on the Technicon Axon system (Miles, Tarrytown, N.Y.) using the Triglyceride kit from Bayer, Total cholesterol (Bayer, Tarrytown, N.Y.), and the PAP150 kit for choline containing phospholipids from bioMerieux. The results were given in mmol/l, and the data is presented in table 10 below. TABLE 10 Total cholesterol, triglycerides and phospholipids of the plasma. Cholesterol Triglycerides Phospholipids Control 10.02 2.95 11.98 0.25% Gendaxin 9.14 2.71 11.19 0.5% Gendaxin + 9.10 2.12 10.66 0.9% TTA
  • Gendaxin to the fish feed has a positive effect on the fatty acid composition of the plasma of the salmon.
  • the fat component is 30% lard, or 2.5-5% of the lard is exchanged with fish oil or 0.15 of the lard is exchanged with TTA.
  • the protein material is 20% milk protein (casein), or half of it is exchanged with fish protein or “Bioprotein”.

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