WO2008136739A1 - Compound feed for aquaculture - Google Patents
Compound feed for aquaculture Download PDFInfo
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- WO2008136739A1 WO2008136739A1 PCT/SE2008/050477 SE2008050477W WO2008136739A1 WO 2008136739 A1 WO2008136739 A1 WO 2008136739A1 SE 2008050477 W SE2008050477 W SE 2008050477W WO 2008136739 A1 WO2008136739 A1 WO 2008136739A1
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- Prior art keywords
- oil
- feed
- group
- aquaculture
- lignan
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
- Y02A40/81—Aquaculture, e.g. of fish
- Y02A40/818—Alternative feeds for fish, e.g. in aquacultures
Definitions
- the present invention generally relates to a novel compound feed for aquaculture, and in particular to such a feed having capability of altering muscle fatty acid composition in species reared in aquaculture.
- Compound feed for aquaculture including plant oils differ in their biochemical composition compared to feeds based on oils from species living in fresh and marine waters. So far, studies have mostly concentrated on the production yield when aquaculture species like fish are grown on feeds with a partial replacement of oils originating from fresh water and marine species by plant oils, e.g. linseed, hempseed, soybean and rapeseed oils. It has been shown that up to 50 % replacement of oils originating from fresh water and marine species by several plant oils does not alter the growth of aquaculture species and feeds with a replacement of 10 to 25 % of the plant oil with oil originating from fresh water and marine species are frequently commercialized .
- plant oils e.g. linseed, hempseed, soybean and rapeseed oils. It has been shown that up to 50 % replacement of oils originating from fresh water and marine species by several plant oils does not alter the growth of aquaculture species and feeds with a replacement of 10 to 25 % of the plant oil with oil originating from fresh water and marine species
- a major drawback of the prior art of plant oil-based feeds for aquaculture species is the decreased amount of eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA) and to some extent arachidonic acid (AA) and an increase in n-6 fatty acids, especially linoleic acid (LA).
- EPA eicosapentaenoic acid
- DPA docosapentaenoic acid
- DHA docosahexaenoic acid
- LA arachidonic acid
- AA arachidonic acid
- LA linoleic acid
- not only the fatty acid composition will be altered towards a lower amount of "marine" fatty acids, notably DHA and EPA, but also the content of several bioactive compounds including phytoestrogens, phytosterols, and other phenolic compounds, may be increased.
- Document [1] discloses the effects of different supplementary feeds on the growth rate of Indian major carp Catla catla.
- Nine different supplementary feeds made from locally available ingredients in India were manufactured and used as supplements to natural feed.
- the best results in terms of gain in total weight, total length and body depths of fingerlings of Catla catla were obtained with oiled and/ or deoiled rice bran.
- Sesame cake mixed with oiled or deoiled rice bran were also tested as supplementary feed but resulted in a decrease of total body depth (thickness) as compared to control feed.
- Document [2] discloses usage of different supplementary feeds in three experimental sets with the supplementary feeds alone or complemented with frozen zooplankton or live zooplankton for Indian major carp Catla catla. In all experiments, reduction in total length, total body depth and total weight were observed for all supplementary feeds.
- One of the feeds contained a mixture of sesame cake and rice bran.
- Document [3] discloses the usage of different supplementary fish feeds made from locally available ingredients in Bangladesh for a carp polyculture system (40 % Catla catla, 20 % Labeo rohita, 20 % Cirrhinus mrigala, 5 % Cyprinus caripo and 15 % Puntius gonionotus).
- One of the fish feed contained fish meal, wheat bran, sesame cake, molasses and a pre-mixture of vitamins and minerals.
- the feed that contained rice bran and mustard oil cake instead of wheat bran and sesame cake resulted in highest gross production of fish, highest carcass protein, protein efficiency ratio and apparent net protein utilization and best apparent feed conversion ratio. This feed also resulted in the highest benefit- to-cost ratio (BCR), whereas the feed containing wheat bran and sesame cake had the lowest BCR.
- BCR benefit- to-cost ratio
- the present invention overcomes drawbacks of the prior art feeds based on vegetable oils, including the decrease in highly unsaturated fatty acids (HUFA).
- HUFA highly unsaturated fatty acids
- the present invention involves a compound feed for aquaculture species comprising i) a lignan represented by formula (I):
- Ri to RO each independently represents an hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a sugar moiety, or Ri and R2 and/ or R 4 and R5 together represent a methylene group or an ethylene group and k, m and n each independently represents 0 or 1, and R7 and Rs independently represents a methyl group or -CH2-O- forming a tetrahydrofuran group with the lignan backbone, ii) an oil or oil mixture containing a 18-carbon chain omega-3 fatty acid, and iii) an antioxidant.
- the lignan of the present invention is preferably a dioxabicyclo [3.3.0] octane derivate represented by formula (II):
- the dioxabicyclo[3.3.0]octane derivates of the present invention are preferably sesame lignans, including sesamin, episesamin and/ or sesamolin.
- the derivates can be present in a pure form in the feed or in the form of different natural or processed sesame products comprising the lignans, such as sesame seeds, sesame oil, sesame meal or sesame cake.
- the oil can be a single plant or vegetable oil comprising the omega-3 fatty acid or a mixture of at least two plant oils, of which at least one comprises the omega-3.
- the omega-3 fatty acid of the oil is preferably ⁇ -linolenic acid and/ or stearidonic acid.
- the oil or oil mixture can also contain an 18-carbon chain omega-6 fatty acid, such as linoleic acid.
- the preferred antioxidant is employed for inhibiting oxidization of the high content of polyunsaturated fatty acids in the oil or oil mixture, thereby increasing the shelf life of the aquaculture feed.
- the antioxidant can, depending on which antioxidant or antioxidant mixture that is employed, result in a coloring of the species fed on the compound feed for aquaculture based on this invention.
- the lignans of the present invention will cause an elongation and desaturation of the 18-carbon chain omega-3 and omega-6 fatty acid in the aquaculture species, in particular in the triacylglycerols and phospholipids of white muscle.
- these shorter carbon chain omega-3 and omega-6 fatty acids are transformed into longer carbon chain omega-3 and omega-6 HUFA, including eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), docosahexaenoic acid (DHA) and arachidonic acid (AA).
- EPA eicosapentaenoic acid
- DPA docosapentaenoic acid
- DHA docosahexaenoic acid
- AA arachidonic acid
- a particular embodiment of the compound feed for aquaculture comprises the lignan defined by formula (I), an antioxidant and an oil or oil mixture having a total 18-carbon chain omega-3 fatty acid content of at least 5 % by weight of the oil or oil mixture, preferably at least 10 %, such as at least 20 % and more preferably at least 30 % or even about or at least 40 % by weight or sometimes even more.
- the aquaculture feed comprises the sesame lignan 2,6-fois-(3,4-methylenedioxy phenyl)- trans-3, 7- dioxabicyclo[3.3.0]octane, an antioxidant and an oil or oil mixture comprising an 18-carbon chain omega-3 fatty acid.
- the feed preferably also comprises at least one additional sesame lignan, preferably sesamin and/ or sesamolin.
- the compound feed for aquaculture of the present invention will, through the induced fatty acid elongation and desaturation, change the fatty acid composition of the muscles and other edible organs and tissues of the aquaculture species. As a consequence, this changed fatty acid composition will be closer to the fatty acid composition of corresponding wild or farmed species fed compound feed for aquaculture based on oils or meals from wild living species compared to the prior art of plant oil-based compound feed for aquacultures.
- the invention therefore provides an improved marine fatty acid profile and quality both for the welfare of the aquaculture species and as aquaculture species are consumed by humans or given as animal food.
- the invention offers the following advantages: - Increases the proportion of omega-3 HUFA in aquaculture species fed the innovative compound feed for aquaculture;
- Fig. 1 is a diagram illustrating the effect of feed components on the relative proportions of omega-3 fatty acids expressed as percentage of total fatty acid content in white muscle triacylglycerols;
- Fig. 2 is a diagram illustrating the effect of feed components on the changes of ⁇ -linolenic acid and docosahexaenoic acid in white muscle triacylglycerol;
- Fig. 3 is a diagram illustrating the effect of feed components on the desaturation index in white muscle triacylglycerol
- Fig. 4 is a diagram illustrating percentage distribution of oxaloacetate and matate (ox-mal) and acetate in the acid soluble fraction from 18:3 (n-3) oxidation;
- Figs. 5A to 5E illustrate relative expression of SRB, cd36, PPAR ⁇ , ⁇ , ⁇ in different sesamin concentrations, with significant differences to control group without sesamin denoted with *;
- Fig. 6 illustrates relative expression of some lipid related genes in salmon, * indicates significant difference between control group and sesamin group (p ⁇ 0.05); and
- Figs. 7 A and 7B illustrate relative expression of ⁇ -5 and ⁇ -6 desaturase with significant differences between the groups denoted with *.
- the present invention generally relates to a new compound feed for aquaculture, the manufacture and use thereof.
- the aquaculture feed of the present invention is based on an oil or oil mixture, in particular a plant oil or oil mixture, complemented with one or more specific lignans, in particular dioxabicyclo [3.3.0] octane derivates or derivatives and sesame lignans. These lignans have the unexpected effect of altering the fatty acid composition in aquaculture species fed the feed.
- the aquaculture species will then have a fatty acid composition that is closer to the fatty acid composition in farmed aquaculture species fed a feed based on traditional ingredients from species living in fresh or marine waters or corresponding wild species.
- it is expected that aquaculture species fed a feed of the present invention will have a better fatty acid composition when used as a food source for humans and other animals as compared to aquaculture species fed prior art plant oil-based feeds.
- the compound feed for aquaculture of the present invention can be used as a primary feed for the aquaculture species or as a supplementary feed, complementing a traditional feed based on raw materials originating from species living in fresh and marine waters.
- the feed of the present invention can be generally be used as feed for any aquaculture species.
- the feed is in particular adapted for carnivorous aquaculture species and preferably carnivorous cold or temperate water aquaculture species.
- Examples of such species include aquaculture species farmed on the Northern and Southern hemispheres, especially in Europe, the Americas, Japan, China and Australia.
- These species include aquaculture species belonging to the family Salmonidae, the orders Gadiformes and Perciformes and flat fishes.
- Salmonidae species include species of the genus Coregonous (whitefishes), Prospoium (round whitefishes), Stenodus (inconnus), Thymallus (graylings),
- Gadiformes is the order of ray-finned fish and include the family of Gadidae, which comprises, among others, cod, haddock, whiting, hake, myh and Pollock.
- Perciformes include both freshwater and saltwater species, e.g.
- Percidae family such as perch pike-perch
- species of the Sparidae family such as sea breams
- species of the Serranidae family such as sea bass
- species of the Scombridae such as Southern Bluefin Tuna (Thynnus maccoyii).
- Other perciformes include Yellowtail (Seriola sp.), Wolffish (Anharhichas lupus) and Barramundi (Lates calcarifer).
- different flat fish species can benefit from the feed of the invention, e.g.
- turbot Piert (Psetta maxima, Scopthalmus rhombus), soles (Soleace), flounders, plaice and Atlantic halibut.
- Pleuronectiformes families Pleuronectidae, Scophthalmidae, Soleidae can be fed by the feed of the invention.
- the feed of the invention is though not limited to carnivorous aquaculture species and fishes but can also be given to non-carnivorous species, including carnivorous and non-carnivorous species of, for instance the Teleostei infraclass.
- a particular preferred aquaculture species of the invention is different fish species.
- Other preferred aquaculture species include telestes, crustaceans and mollusks
- the aquaculture feed of the invention comprises a lignan represented by formula (I):
- Ri to RO each independently represents an hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a sugar moiety, or Ri and R2 and/ or R 4 and R5 together represent a methylene group or an ethylene group and k, m and n each independently represents 0 or 1, and R7 and Rs independently represents a methyl group or -CH2-O- forming a tetrahydrofuran group with the lignan backbone.
- Examples of an alkyl group having 1 to 3 carbon atoms include a methyl group, ethyl group, n-propyl group and isopropyl group.
- Examples of a sugar moiety include a monoglycoside, a diglycoside and a triglycoside moiety, such as mono-, di- or triglucoside, -galactoside, -fructoside or -glucuronide.
- the lignan is a dioxabicyclo [3.3.0] octane derivate represented by formula (II):
- Ri to Re each independently represents an hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a sugar moiety, or Ri and R2 and/ or R 4 and R5 together represent a methylene group or an ethylene group and k, m and n each independently represents 0 or 1.
- the octane derivate is R7 and Rs in the form of -CH2-O- forming a respective tetrahydrofuran group with the lignan backbone to the structure II.
- Ri and R2 together represent a methylene group and R 4 and R5 together represent a methylene group or R 4 is a hydrogen atom and R5 is a methyl group.
- k, m, n are all zero or k and m are zero and n is one.
- the feed can comprise one of the lignans defined by formula (I), such as one of the dioxabiocyclo [3.3.0] octane derivates defined by the formula (II), or a mixture of at least two such lignans.
- This lignan mixture can be in any range from 1 :0, i.e. only a first lignan, to 0: 1 , i.e. only a second lignan.
- the same principles apply mutatis mutandis to a lignan mixture of more than two lignan.
- an equimixture 1 : 1 of two lignans of the invention, such as sesamin and episesamin can be used in the feed.
- more than two lignans of the invention are used in a mixture.
- different mixtures of sesamin and sesamolin as present in natural sesame oil can be used.
- the lignan is a sesame seed lignan, or a derivate of such a sesame lignan.
- Specific examples of such lignans encompassed by the formula (II) include 2,6-fois-(3,4-methylenedioxy phenyl)-cis-3,7- dioxabicyclo [3.3.0] octane (sesamin); 2,6-fois-(3,4-methylenedioxy pheny I)- trans- 3,7-dioxabicyclo[3.3.0]octane (episesamin); 2-(3,4-methylenedioxy-6-hydroxy phenyl)-6-(3,4-methylenedioxy pheny l)-cis-3,7-dioxabicyclo [3.3.0] octane
- Such glycosides include mono-, di- and triglycosides, especially of sesaminol, episesaminol, sesamolinol, pinoresionol or 2-(3-methoxy-4-hydroxy phenyl)-6-(3,4- methylenedioxy phenyl)-cis-3,7-dioxabicyclo [3.3.0] octane.
- Preferred lignans of the present invention are sesamin, episesamin, sesamolin, a mixture of sesamin and episesamin, a mixture of sesamin and sesamolin, a mixture of episesamin and sesamolin, or a mixture of sesamin or sesamolin and at least one additional sesame lignan presented above.
- Sesamin and sesamolin are the major oil-soluble lignans of sesame seeds.
- sesaminol 2-(3-methoxy-4-hydroxy phenyl)-6- (3,4-methylenedioxy phenyl)-cis-3,7-dioxabicyclo[3.3.0]octane, sesamolinol and pinoresinol are also found in the sesame seeds in free or glucosilated forms.
- other lignans has been reported in wild species of genus Sesamum, such as sesangolin in Sesamum angolense and Sesamum angustifolium and 2-episealatin in Sesamum alatum.
- the lignans of the present invention can be obtained by extraction and concentration from sesame seed or oil using various organic solvents that are able to extract and dissolve the derivates.
- solvents include super-critical carbon dioxide, acetone, methyl ethyl ketone, diethyl ketone, methanol, ethanol or mixtures of these solvents.
- a particular example of such extraction involves uniformly mixing sesame oil with any of the above-mentioned solvents, allowing the mixture to stand undisturbed at a low temperature, performing phase separation in accordance with routine methods, such as centrifugal separation, and distilling off the solvent from the solvent fraction. More specifically, after dissolving sesame oil in 2 to 10 volumes, and preferably 6 to 8 volumes, of acetone, the solution is allowed to stand undisturbed overnight at -
- the resulting oil component forms a precipitate and the acetone is removed from the filtrate obtained by filtration to obtain an extract having as its main ingredient the lignan of the present invention.
- supercritical extraction and fractionation methods can be used.
- another method for obtaining a product containing the lignans of the present invention comprises mixing sesame oil with hot methanol or hot ethanol, allowing the mixture to stand undisturbed at room temperature and distilling off the solvent from the solvent fraction. More specifically, after vigorously mixing sesame oil with 2 to 10 volumes and preferably 5 to 7 volumes of hot methanol or ethanol (50 0 C or higher), phase separation is carried out in accordance with routine methods, such as by standing the mixture undisturbed at room temperature or by centrifugal separation. The solvent is distilled off from the solvent fraction to obtain an extract having for its main ingredient the derivative of the present invention. Moreover, the extract can also be obtained by utilizing super-critical gas extraction.
- the sesame oil to be used may be a finished product or any of the crude products in the production process of sesame oil prior to the decoloring step.
- a product containing the lignan of the present invention can be obtained by extraction from sesame seeds or the defatted products sesame seeds (residual oil content: 8 to 10 %). After crushing the sesame seeds or defatted products as necessary, extraction can be performed in accordance with routine methods by pressing or by using any of the above-given solvents. After separating the extraction residue, the solvent is removed from the extract liquid by evaporation and so forth to obtain the extract. Further purification can be performed using traditional methods such as column chromatography, high-performance liquid chromatography, recrystallization, distillation and liquid-liquid exchange distribution chromatography.
- the lignan of the present invention can also be obtained by synthesis in accordance with routine methods.
- Episesamin is a sesame lignan that is not naturally occurring in natural sesame products. It is, however, produced during refining of sesame oil and is variably present in refined sesame oils. It can thus be manufactured from sesamin, for instance, by bleaching in the presence of acidic clay.
- lignans of the present invention can be extracted different tree species, such as from the heart wood and/ or leaves from, for instance, Hinoki cypress ⁇ Chamaecyparis obtuse), Chamaecyparis pisife ⁇ a, Chamaecyparis obtusa, Chamaecyparis obtusa cv. Breviramea, Chamaecyparis pisifera cv. Plumosa-aurea, Chamaecyparis lawsoniana, Paulownia species.
- other plant sources including tea seeds (Camellia oleifera), can be used as lignan source.
- the lignans of the present invention must not necessarily be used in highly pure form in the feed.
- substances that contain the lignans of the invention and which may be obtained from naturally occurring sources can be used according to the present invention. These include sesame seeds, sesame oil, such as crude/virgin, roasted or refined oil, and sesame cakes or similar products from different species of the genus Sesamum.
- a preferred derivate source of the present invention is sesame cake comprising a mixture of sesame lignans having the fatty acid elongation and desaturation effect in fed aquaculture species.
- the compound feed for aquaculture feed of the invention also comprises an oil or a mixture of oils, preferably plant oils.
- the oil or oil mixture comprises an 18-carbon chain omega-3 fatty acid and optionally an 18-carbon chain omega-6 fatty acid.
- These 18-carbon chain fatty acids will, when digested by the aquaculture species, be elongated and desaturated into longer chain fatty acids due to the presence of the lignan of the present invention. Thus, the inclusion of the lignan will trigger a conversion of these shorter chain omega-3 and omega-6 fatty acids to the corresponding longer chain omega-3 and omega-6 fatty acids in the aquaculture species.
- a fatty acid can be denoted by Y: Z, where Y specifies the number of carbons in the carbon chain while Z specifies the number of double bounds in the carbon chain. If the fatty acid is an omega-3 fatty acid, the postfix (n-3) is used. An omega-6 fatty acid correspondingly has (n-6) as postfix.
- the change in fatty acid composition brought by the feed of the present invention is particularly taking place in white muscles of the aquaculture species, while fatty acids in red muscle and liver were only slightly affected.
- the white muscles represent the main muscle part in the most important aquaculture species, approximately 95 %, so the change in fatty acid composition caused by the present invention will have a major impact to the total fatty acid composition in the aquaculture species.
- the lack of effect of the lignan of the invention in modifying the fatty acid composition in liver may be positive for the welfare of the aquaculture species, as the species might otherwise experience negative effects on the liver function.
- the change in fatty acid composition in the white muscles was detected both in the phospholipid fraction (PL) and in the triacylglycerol fraction (TAG).
- the lignans of the present invention affect the genes involved in the lipid metabolism in the aquaculture species, in particular in white muscles.
- This gene activation may lead to a modulation of the activity of the ⁇ 5 desaturase and/ or ⁇ 6 desaturase activity, which two enzymes are involved in the elongation and desaturation of 18:3 (n- 3) and 18:4 (n-3) into 20:4 (n-3), 20:5 (n-3), 22:5 (n-3) and 22:6 (n-3) and elongation and desaturation of 18:2 (n-6) into 20:4 (n-6).
- Suitable oils that can be used according to the present invention include plant oils having a high 18-carbon chain omega-3 content.
- the oil or oil mixture preferably has a total 18-carbon chain omega-3 content of at least 5 % by weight of the oil or oil mixture, preferably at least 10 % by weight and more preferably at least 20 %, such as at least 30 % by weight or about or at least 40 % by weight.
- the oil or oil mixture of the present invention preferably also has a high polyunsaturated fatty acid content.
- this polyunsaturated fatty acid content is at least 40 % and more preferably at least 50 % of the total fatty acid content of the oil or oil mixture.
- Preferred oils can be selected from the group of linseed/ flaxseed oil, perilla seed oil, soybean oil, rapeseed oil, hempseed oil, black current seed oil and oils from the Boraginaceoe family.
- the compound feed for aquaculture can contain a single oil or a mixture of at least two of the above-mentioned oils or other similar oils. As some of these oils have a very high 18-carbon chain omega-3 content, it is also possible to provide an oil mixture of at least one of the above- mentioned oils and another plant oil with low or no 18-carbon chain omega-3 or 18-carbon chain omega-6 content, such as sunflower oil or sesame oil.
- the oil is preferably present in at least 10 % by weight of the feed, more preferably at least 20 % by weight, such as 20 to 35 % by weight.
- the lignan of the invention is preferably present in at least 0.5 % by weight of the oil or oil mixture in the feed, more preferably at least 1 % by weight, such as at least 2 % by weight of the oil or oil mixture.
- the aquaculture feed of the present invention furthermore preferably comprises an antioxidant or a mixture of antioxidants.
- the antioxidative effect is very advantageous for the shelf life and integrity of the high oil content of the feed.
- the antioxidants protect the polyunsaturated fatty acids in the feed from oxidation during storage. These polyunsaturated fatty acids are otherwise readily oxidized in air because of their unsaturated bonds. If such an oxidation is taking place at a great extent, the amount of 18-carbon chain omega-3 fatty acids in the feed will diminish, leading to a less positive effect for animals feeding on the feed of the invention.
- Preferred antioxidants of the invention preferably have advantageous health effects to the aquaculture species feeding on the feed of the invention.
- Such antioxidants include carotenoids, vitamin E, tocopherols, tocotienols.
- Carotenoids are organic pigments that are naturally occurring in chromoplasts of plants and some other photosynthetic organisms like algae, some fungus and bacteria or can be manufactured synthetically.
- the carotenoids of the present have dual functions in the feed. Firstly, they are antioxidants.
- the carotenoids of the invention can also affect the coloring of the aquaculture species feeding on the carotenoid-containing feed. For instance, the pink color of salmon is due to the presence of carotenoids in the salmon feed. This means that the carotenoids contribute to a more inviting and enticing appearance of the species when used as human food.
- Astaxanthin is an example of a preferred carotenoid that can be used in the feed of the invention. Astaxanthin is a xanthophyll that causes a coloring of
- Salmonidae fishes can taxan thin is another carotenoid example that can be used according to the present invention. Cantaxanthin is traditionally used in similar applications as astaxanthin and the two carotenoids may also be used in combination. If the feed of the invention is intended for Salmonidae species, the antioxidant is preferably astaxanthin or a mixture of astaxanthin and at least one other antioxidant.
- Preferred tocopherols and tocotrienols include ⁇ -, ⁇ -, ⁇ -, ⁇ -tocopherols and tocotrienols.
- the antioxidant or mixture of at least two antioxidants is preferably added to the aquaculture feed to have a final concentration traditionally employed in aquaculture feeds.
- the feed can comprise at least 5 mg antioxidant per kilogram dry weight of the feed.
- the antioxidant concentration is at least 10 mg/kg, preferably at least 20 mg/kg, such as at least 40 mg/kg, at least 50 mg/kg or more preferably 60 mg/kg by dry weight of the feed.
- the feed of the present invention may contain one or more additional ingredients besides the oil (mixture), the antioxidant and the lignan.
- these ingredients can be selected from traditional additives and ingredients of the prior art (supplementary) aquaculture feeds.
- Non-limiting examples include casein, gelatin, meal processed from fresh water or marine water species, corn, wheat gluten, starch and other cereal products, soy lecithin and other soy products, dextrin, vitamins, minerals, Ca3SO4, sodium alginate, etc.
- the concentration of the lignan of the present invention may preferably be in the range of 0.1 to 10 % by dry weight of the feed.
- the main constituents of the present invention i.e.
- the lignan and the oil or oil mixture can be manufactured separately and even be provided as separate pellets.
- a compound feed of the invention may then be provided by mixing the two main constituents before or in connection with the feeding of the actual aquaculture species. It is also possible to administer the two constituents without prior mixing, i.e. feeding the species sequentially or substantially simultaneously with the derivate and the oil.
- the final compound feed for aquaculture can for instance be in the form of pellets, powder or in a wet form.
- a first aspect of the invention relates to a compound feed for aquaculture comprising a lignan represented by formula (I), an oil or oil mixture having a total 18-carbon chain omega-3 fatty acid content of at least 5 % by weight of the oil or oil mixture and optionally but preferably an antioxidant.
- the feed may optionally include well-known aquaculture feed additives.
- a second aspect of the invention defines a method of manufacturing the compound feed for aquaculture of the first aspect. This method involves mixing the lignan(s) with the oil or oil mixture and the antioxidant(s), optionally also involving adding well-known feed additives. If including more than two ingredients, the feed can be manufactured by mixing them in any order. The ingredients may be ground prior to or after mixture and can then be pressed into feed pellets of selected sizes, feed powder or in some other form.
- a third aspect of the invention relates to the use of the lignan represented by formula (I) as an additive to an oil-containing aquaculture feed having a 18- carbon chain omega-3 fatty acid content of at least 5 % by weight of the oil and comprising at least one antioxidant.
- a fourth aspect of the invention relates to a compound feed for aquaculture comprising episesamin, an antioxidant and an oil or oil mixture comprising an 18-carbon chain omega-3 fatty acid.
- the feed preferably also comprises sesamin and may optionally include well-known aquaculture feed additives.
- a fifth aspect of the invention defines a method of manufacturing the aquaculture feed of the fourth aspect. This method involves mixing the episesamin with the oil or oil mixture and the antioxidant, optionally also involving adding sesamin and/ or well-known aquaculture feed additives. If including more than two ingredients, the feed can be manufactured by mixing them in any order. The ingredients may be ground prior or after mixture and can then be pressed into feed pellets of selected sizes.
- a sixth aspect of the invention relates to the use of episesamin as an additive in an oil-based, antioxidant-comprising aquaculture feed, preferably such a feed comprising one or more 18-carbon chain omega-3 fatty acids.
- the feeds of the invention can be used for altering the muscle fatty acid composition in an aquaculture species.
- This composition altering involves feeding the species with the feed to thereby induce the elongation and desaturation of the 18-carbon chain omega-3 fatty acids in the feed into longer chain polyunsaturated omega-3 fatty acids, preferably into such omega-3 fatty acids having 20 or 22 carbon atoms in their respective carbon chains.
- a seventh aspect of the invention relates to the use of the lignan represented by the formula (I) in increasing a proportion of N-carbon chain omega-3 fatty acids in muscle of the aquaculture species, where N is larger than 18. In a preferred embodiment, N is 20 or 22.
- An eighth aspect of the invention relates to the use of the lignan represented by the formula (I) in increasing elongation and desaturation of 18:3 (n-3) and/or 18:4 (n-3) in muscle of the aquaculture species.
- the feed of the present invention has a further advantageous effect if the lignin is sesamin or a mixture of sesamin and at least one additional lignan. Sesamin present in the feed is partly taken up by the aquaculture species and becomes accumulated in the muscles. Sesamin can therefore be used as a traceable marker for detecting the presence of sesamin in the feed of the aquaculture species.
- sesamin in the muscle of aquaculture species will have several beneficial effects.
- PPAR- ⁇ peroxisome proliferator activator receptor alpha
- the lignan of the feed is exchanged for a 1 ,3-benzodioxole or a 1 ,3-benzodioxole derivate.
- 1 ,3- benzodioxole is represented by formula (III):
- a 1 ,3-benzodioxole derivate is defined as a chemical substance having a functional 1 ,3-benzodioxole moiety connected to at least one side chain X connected to the benzodioxole moiety as defined by formula (IV) :
- the derivate could be sesamin, episesamin, sesamolin, episesaminol, sesaminol, piperitol, sesamolinol, episesaminone, sesangolin, 2-episesalatin.
- 1 ,3-benzodioxole derivates include 5-[l-[2-(2-ethoxyethoxy)ethoxy)ethoxy]- 1 ,3-benzodioxole (sesamex) illustrated by formula (V):
- PBO piperonyl butoxide
- 5-[2-(2- butoxyethoxy)ethoxymethyl]-6-propyl]- 1 ,3-benzodioxole having formula (VI):
- the aquaculture feed comprises 1 ,3-benzodioxole or a 1 ,3- benzodioxole derivate, an oil or oil mixture having a total 18-carbon chain omega-3 fatty acid content of at least 5 % by weight of the oil or oil mixture and optionally but preferably an antioxidant.
- the feed according to this aspect can be used in the same way as the previously discussed feeds.
- Sesame lignans were used in the form of a sesamin/ episesamin mixture (1 : 1 , w/w). Fatty acid peaks were identified by comparison with the standard mixture GLC-68 A (Nu-check Prep, Inc, Elysian, Minnesota, USA). All solvents and other chemicals were also purchase from Merck and were used without further purification.
- the feed was prepared according to the method of document [5].
- the composition of the diet is shown in Table I and fatty acid composition of diets is shown in Table II.
- Lipid source was either linseed oil or linseed oil : sunflower oil (6 : 4)
- (n-3)/(n-6) 4.88 0.97 1.04 3.61 3.62 saturated fatty acids include, among others, 14:0, 16:0, 18:0, 20:0, 22:0 monounsaturated fatty acids include, among others, 16: 1 , 18: 1 (n-9), 18: 1 (n-7), 20: 1 , 22: 1 , polyunsaturated fatty acids include, among others, 18:2 (n-6), 18:3 (n- 3), 20:5 (n-3), 22:6 (n-3)
- Tissues and diets were extracted following the method of document [6] .
- Total lipids of tissues were separated into phospholipids (PL) and triacylglycerols (TG) according to the method disclosed in document [7].
- Total lipids in the diets and the PL and TG lipid fractions of tissues were methylated following the procedure of document [8] and the fatty acids were analyzed with gas chromatograph CP3800 (Varian AB, Sweden) equipped with flame ionisation detector (FID) and split injector and fitted with a fused silica capillary column BPX 70 (SGE, Austin, Texas, length 50 m, inner diameter 0.22 mm, 0.25 ⁇ m film thickness).
- gas chromatograph CP3800 Varian AB, Sweden
- FID flame ionisation detector
- BPX 70 fused silica capillary column
- the column temperature was programmed to start at 158 0 C, hold 5 min and then increase 2 °C/min from 158 °C to 220 °C and remain at 220 0 C for 8 min.
- the carrier gas was helium (0.8 ml/ min) and make up gas was nitrogen.
- the injector and detector temperatures were 230 0 C and 250 0 C respectively.
- Fatty acids were identified by comparison with the standard fatty acid mixture GLC-68. Peak areas were integrated using a Star chromatography workstation software version 5.5 (Varian AB, Sweden).
- the fat content was about 2 % in the white muscle and about 15 % in the red muscle.
- the phospholipid fraction (PL) represented about 25 % of the white muscle lipids but only a few percent of the red muscle lipids.
- White muscle represents the main muscle part, approximately 95 %, and the red muscle consists of the remaining 5 %. Therefore, the triacylglycerol storage fat fraction (TG) is the important fraction in terms of the fatty acid composition of fish muscle as human food.
- n-3 HUFA the ratio of n-3 HUFA to 18:3 (n-3), i.e. the proportion of fatty acids with more than or equal to 20 carbons and at least 3 double bounds to ⁇ -linolenic acid, increased in the white muscle TG, see Fig. 3.
- SAFA saturated fatty acids
- MUFA monounsaturated fatty acids
- PUFA polyunsaturated fatty acids
- HUFA highly unsaturated fatty acids (>3 double bounds)
- liver fatty acid composition was not significantly altered in any of the two lipid fractions, TG and PL.
- Triacylglycerols TAG
- Sesamin/episesamin especially increased the proportion of DHA and decreased that of ALA, see Fig. 2.
- addition of the sesame lignans in the vegetable oil-containing feed increases the desaturation index in the oil fed fish as is illustrated in
- Lipid class Triglycerides Phospholipids
- Lipid class Triglycerides Phospholipids
- sesamin and episesamin can be added to feeds containing plant oils containing eighteen carbons, unsaturated fatty acids to improve their elongation and desaturation in aquaculture species towards long chain polyunsaturated fatty acids (LCPUFA), especially DHA, which is beneficial in relation to nutrition of both aquaculture species and humans.
- LCPUFA long chain polyunsaturated fatty acids
- the total amount of PUFA in sesamin fed aquaculture species is lower than in species fed diets without sesamin.
- Previously sesamin has been reported to increase ⁇ -oxidation, which may be the mechanism causing a lower PUFA content in sesamin fed species.
- Sesame lignans were also tested for possible interactions in lipid metabolism in Atlantic salmon (Salmo solar L.) hepatocytes. Incubation with the lignans resulted in the increased percentage of DHA and clearly increased ⁇ - oxidation, elongation and desaturation of 18:3 (n-3). The main ⁇ -oxidation product of the acid soluble fraction was acetate. The DHA levels elongated and desaturated from 18:3 (n-3) were twice as high when hepatocytes were incubated with the lignans compared to the control group. The amount of secreted triacylglycerol was lower in lignan-incubated hepatocytes. Incubation with the lignans also showed effects of expression on some lipid related genes.
- the radiolabeled FA [1- 14 C] 18:3 (n-3) (specific radioactivity 50 mCi/mmol) was obtained from American Radiolabeled Chemicals (St. Louis, MO, USA).
- BSA essential fatty acid free bo
- Sesamin Sesamin/episesamin mixture, 1 : 1 , w/w was a kind gift from Takemoto Oil and Fat Co., Ltd. (Gamagori Aichi, Japan). Fatty acid peaks were identified by comparison with the standard mixture GLC-68 A (Nu-check Prep, Inc, Elysian, Minnesota, USA). Ammonium dihydrogenphosphate, Perchloric acid (HClO 4 ), TLC-plates, all solvents and other chemicals for fatty acid and sesamin analysis and were purchase from Merck (Darmstadt, Germany).
- the cells were incubated at 12 0 C for 48 h.
- the radiolabeled experiment flasks with and without sesamin (4 each) were washed and harvested in PBS for further analysis of ⁇ -oxidation and radiolabeled lipid classes and radiolabeled cellular fatty acids.
- the cells in the two flasks with no FA substrate added were denaturated after the incubation and thereafter added radiolabeled substrate in order to be used as a negative control for the ASP measurements and HPLC analyses.
- control and sesamin flask (4 each) were washed in PBS prior to isolation of mRNA according to the protocol RNeasy ® Mini Kit for gene expression analysis and 3 flasks of each control and sesamin were washed and harvested in PSB for fatty acid and sesamin analysis.
- Sesamin solved in DMSO (7.4 ⁇ l/5 ml medium) was added the flasks with final concentrations of: 0.005 mM, 0.05 mM, 0.075 mM and 0.1 1 mM to duplicate flasks of cells in a regression design and incubated for 42 h at 12 0 C.
- the final concentration of 0.05 mM sesamin in culture medium were added to the hepatocytes in duplicates flasks. The cells were incubated for 0, 18, 24, 42, 48, 66 and 72 h. As control in both the dose response study and the time study DMSO (7.4 ⁇ l/5 ml medium) was added the cells.
- the cells were washed in PBS prior to isolation of mRNA according to the protocol RNeasy ® Mini Kit for gene expression analysis.
- the FAs were identified by comparison with external standards and retention times.
- the lipids extracted from the media were separated on TLC-plates into lipid classes using a mixture of petroleum ether, diethyl eter and acetic acid (1 13:20:2 v/v/v).
- the lipid classes, phospholipids (PL), monoglycerides (MG) free fatty acids (FFA) and triacylglycerols (TAG) were developed by spraying 0.2 % 2', 7 '-dichloro fluorescein in methanol and identified by compassion to standards under UV-light.
- the lipid classes were scraped off and dissolved in scintillation fluid for scintillation counting (TRI-CARB 1900 TR, Packard Instruments).
- the esterified fatty acids, PL, MG and TAG fraction will be denoted as secreted fatty acids.
- Lipids from the none-radioactive cells and media used for the time course gene expression study were extracted by using hexane:isopropanol (3:2 v/v). Total lipids were converted to fatty acid methylesters by using BF3 and analysed with Gas Chromatograph CP3800 (Varian AB, Sweden) according to Fredriksson et al. [15].
- the capacity of ⁇ -oxidation was measured by determination of the oxidation products 14 C acid soluble products (ASP) and 14 C CO2 as described by Christiansen et al. [16].
- 14 C CO2 produced during the incubation of the cells was measured by transferring 1.5 ml of the media to glass vials sealed with a rubber stop and a central well containing a Whatman filer paper with 0.3 ml phenylethylamine/ methanol (1 : 1 , v/v). The medium were acidified with 0.3 ml IM HClO 4 and 14 C CO2 was trapped for 1 h.
- the remaining supernatant was neutralised with NaOH and the different ASP were detected by using high pressure liquid chromatography (HPLC) equipped with a ChromSep Inertsil C8-3 column (250 mm x 4.6 mm stainless steel), an UV- detector at 210 nm and radioactive detector A- 100 (Radiomatic Instrument & Chemicals, Tampa, FL, USA) coupled to the UV detector.
- HPLC high pressure liquid chromatography
- the mobile phase was 0.1 M ammonium dihydrogenphosphate adjusted with phosphoric acid to pH 2.5, the flow rate was 1 ml/min.
- the components were identified by comparison to external standards and retention times.
- the protein content of the cells was determined by using the total protein kit
- CoA oxidase activity was determined according to Small et al. [19].
- the oxidation of 2,7 dichloroflourescin (LDCF) was measured with GBC UV/VIS 98 (GBC Scientific equipment, PTY, LTD, Melborne, Victoria, Australia) spectrophotometer (502 nm) during 3 min.
- the assay mixture contained lO ⁇ l LDCF, 50 ⁇ l peroxidase type II in 0.1 M TRIS, 10 ⁇ l BSA (60 mg/ml), lO ⁇ l
- the cDNA was synthesized following a modified protocol from the Taq Man Reverse Transcription Reagents kit (Applied Biosystems).
- the Oligo d(T) 16 primers were used.
- the reaction was preformed by incubating the samples at 25 0 C for 10 min, 48 0 C for 6 min, 95 0 C for 50 min and was terminated by reducing temperature to 10 0 C.
- Primers for Real-Time PCR analysis (Table VI) were designed using the Primer Express® software and ordered from Invitrogene (CA, USA). They were designed on available salmon sequences in the GenBank ®
- AACTCAGTGAAGAG- TGCGGCGGTGATG- DQ26604 1.79 1 1 , 12 ssalSRB GCCAAACTTG ATG 3
- Relative expressions of the different genes, in relation to housekeeping genes were determined using the Relative Expression Software Tool (REST-384 ⁇ - version 1). For all other data, the student t-test in Microsoft Office Excel 2003 was used.
- the addition of sesamin significantly reduced the saturated fatty acids (SAFA, p ⁇ 0.01) and the monounsaturated fatty acids (MUFA, p ⁇ 0.02) and elevated the n-3 polyunsaturated fatty acids (p ⁇ 0.01).
- the proportion of DHA was significantly higher in the sesamin-incubated hepatocytes, from 27.2 % to 36.0 % (p ⁇ 0.01) while the proportion of EPA did not change.
- the desaturation index (n-3 LCPUFA/ 18:3n-3) was increased from 27.0 to 33.8 in the presence of sesamin (p ⁇ 0.05).
- SAFA saturated fatty acids
- MUFA monounsaturated fatty acids
- PUFA polyunsaturated fatty acids (n-3)
- LCPUFA 20:5 (n-3) + 22:5 (n-3) + 22:6 (n-3) *P- value present comparison of sesamin and control group.
- the percentage of DHA was significantly higher in the sesamin treated group than in the control group, 20.2 % versus 10.5 % (p ⁇ 0.001).
- the percentages of 18:4 (n-3) (p 0.04) and the total amount of
- the compound increased by sesamin in the ASP fraction was the acetate being 53.5 % of ASP in the control group and 72.6 % of ASP in the sesamin group (P ⁇ 0.001), correspondingly the oxaloacetate and malate decreased, see Fig. 4. No significant differences in the enzymatic activity of acetyl CoA-oxidase between the groups were found, being 0.35 ⁇ 0.08 and 0.39 ⁇ 0.02 m unit mg protein- 1 in control respectively sesamin cells.
- PPAR ⁇ and CD36 were significantly down regulated at a concentration of 0.05 niM, when the concentration was increased to 0.075 mM only CD36 was significantly down regulated and at a dose of 0.1 ImM SRB and PPAR ⁇ were significantly down-regulated, see Figs. 5A to 5E. The lowest concentration 0.005 mM had no effect.
- ⁇ -5 and ⁇ -6 desaturases were significantly lower at several time points.
- Fig. 6 shows relative expression of respectively gene for each group. The relative expression decrease in the sesamin treated cells during the first 42 h. Both ⁇ -5 and ⁇ -6 desaturases followed the same pattern of relative expression.
- Fig. 6 illustrates relative expression of some lipid related genes in salmon.
- the increased DHA levels on this study could also indicate increased peroximal ⁇ -oxidation.
- the increased expression of cptl indicates mitochondria ⁇ - oxidation.
- 18:3 (n-3) and its elongated and desaturated products were manly oxidized in the peroxisomes and that ⁇ - oxidation of other fatty acids can be increased in the mitochondria.
- 18:3 (n-3) In the sesamin treated cells incubated with non radiolabeled 18:3 (n-3), lower percentage of 16:0 was found, possibly due to increased mitochondrial ⁇ - oxidation.
- CD36 a gene involved in lipid storage and uptake is regulated by PPAR ⁇ and was also downregulated in the dose study at 0.05 and 0.075 niM sesamin. This may also affect the content of TAG in secreted lipids.
- the sesamin content in the cells was only a small proportion of the given amount of sesamin to the cells (data not shown). The bioavailability of episesamin was higher than that of sesamin.
- sesamin is a potent modulator of fatty acid metabolism in salmon hepatocytes. It significantly increased desaturation and elongation of 18:3
- sesamin has effect on several lipid related genes such as ⁇ -5 and ⁇ -6 desaturase and it decreases secretion of lipid from hepatocytes, in particular
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Abstract
Description
Claims
Priority Applications (5)
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EP08779278A EP2152093A4 (en) | 2007-05-04 | 2008-04-25 | Compound feed for aquaculture |
US12/598,756 US20100144865A1 (en) | 2007-05-04 | 2008-04-25 | Compound feed for aquaculture |
CA002686318A CA2686318A1 (en) | 2007-05-04 | 2008-04-25 | Compound feed for aquaculture |
AU2008246396A AU2008246396A1 (en) | 2007-05-04 | 2008-04-25 | Compound feed for aquaculture |
CL2008001277A CL2008001277A1 (en) | 2007-05-04 | 2008-05-02 | Feed for aquaculture and production method, which comprises a ligano of formula (1), at least 20% by weight of a vegetable oil with a total of 18 c chain omega-3 fatty acid of at least 30% in weight, and carotenoid; method to alter the composition of fatty acids in the muscle in aquaculture species. |
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EP (1) | EP2152093A4 (en) |
AU (1) | AU2008246396A1 (en) |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2011007102A1 (en) * | 2009-07-15 | 2011-01-20 | Universite Joseph Fourier (Grenoble 1) | Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid |
WO2011031166A3 (en) * | 2009-09-14 | 2011-07-28 | Ewos Innovation As | Fish feed |
WO2015028832A1 (en) | 2013-08-29 | 2015-03-05 | Nemzeti Agrárkutatási És Innovációs Központ (Naik) | Process for feeding fish, fish meat and food product |
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CN107846938A (en) * | 2015-05-20 | 2018-03-27 | 印第安纳大豆联盟有限公司 | The method that soybean protein utilization rate is improved by salmonidae fish |
KR102578152B1 (en) * | 2020-08-31 | 2023-09-14 | 부산대학교 산학협력단 | Additive composition for low fish meal feed comprising PPARγ antagonist |
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US5336496A (en) * | 1989-03-07 | 1994-08-09 | Suntory Limited | Inhibitor for delta 5-desaturase |
CN1132042A (en) | 1995-12-03 | 1996-10-02 | 张利民 | Puffed foodstuff containing fish oil |
EP0782827A1 (en) * | 1995-07-04 | 1997-07-09 | Suntory Limited | FOOD COMPOSITION CONTAINING BALANCING AGENT FOR $g(v)-6 AND $g(v)-3 UNSATURATED FATTY ACIDS |
JPH11269456A (en) | 1998-03-19 | 1999-10-05 | Suntory Ltd | Highly unsaturated fatty acid composition |
CN1339262A (en) | 2001-09-21 | 2002-03-13 | 阮生 | Edible sesame oil |
US6358998B1 (en) * | 1999-04-28 | 2002-03-19 | Rinoru Oil Mills Co., Ltd | Body fat-reducing agent comprising dioxabicyclo[3.3.0] octane derivative as active ingredient |
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GB9704904D0 (en) * | 1997-03-10 | 1997-04-30 | Riley Fletcher Foundation The | Essential oil composition |
DE60001229T2 (en) * | 1999-04-09 | 2003-10-30 | Smithkline Beecham Corp | triarylimidazoles |
GB0007405D0 (en) * | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
-
2008
- 2008-04-25 EP EP08779278A patent/EP2152093A4/en not_active Withdrawn
- 2008-04-25 AU AU2008246396A patent/AU2008246396A1/en not_active Abandoned
- 2008-04-25 WO PCT/SE2008/050477 patent/WO2008136739A1/en active Application Filing
- 2008-04-25 CA CA002686318A patent/CA2686318A1/en not_active Abandoned
- 2008-04-25 US US12/598,756 patent/US20100144865A1/en not_active Abandoned
- 2008-05-02 CL CL2008001277A patent/CL2008001277A1/en unknown
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US5336496A (en) * | 1989-03-07 | 1994-08-09 | Suntory Limited | Inhibitor for delta 5-desaturase |
EP0782827A1 (en) * | 1995-07-04 | 1997-07-09 | Suntory Limited | FOOD COMPOSITION CONTAINING BALANCING AGENT FOR $g(v)-6 AND $g(v)-3 UNSATURATED FATTY ACIDS |
CN1132042A (en) | 1995-12-03 | 1996-10-02 | 张利民 | Puffed foodstuff containing fish oil |
JPH11269456A (en) | 1998-03-19 | 1999-10-05 | Suntory Ltd | Highly unsaturated fatty acid composition |
US6358998B1 (en) * | 1999-04-28 | 2002-03-19 | Rinoru Oil Mills Co., Ltd | Body fat-reducing agent comprising dioxabicyclo[3.3.0] octane derivative as active ingredient |
CN1339262A (en) | 2001-09-21 | 2002-03-13 | 阮生 | Edible sesame oil |
WO2006025988A1 (en) * | 2004-07-29 | 2006-03-09 | Schering-Plough Ltd. | Use of alk 5 inhibitors to modulate or inhibit myostatin activity leading to increased lean tissue accretion in animals |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2011007102A1 (en) * | 2009-07-15 | 2011-01-20 | Universite Joseph Fourier (Grenoble 1) | Use of at least one omega-3 fatty acid and of at least one polyphenol for the endogenous synthesis of eicosapentanoic acid and docosahexanoic acid |
WO2011031166A3 (en) * | 2009-09-14 | 2011-07-28 | Ewos Innovation As | Fish feed |
WO2015028832A1 (en) | 2013-08-29 | 2015-03-05 | Nemzeti Agrárkutatási És Innovációs Központ (Naik) | Process for feeding fish, fish meat and food product |
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CL2008001277A1 (en) | 2009-01-23 |
EP2152093A1 (en) | 2010-02-17 |
AU2008246396A1 (en) | 2008-11-13 |
EP2152093A4 (en) | 2011-05-25 |
US20100144865A1 (en) | 2010-06-10 |
CA2686318A1 (en) | 2008-11-13 |
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