WO2009064195A2 - Maturation sexuelle réduite chez des poissons - Google Patents

Maturation sexuelle réduite chez des poissons Download PDF

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Publication number
WO2009064195A2
WO2009064195A2 PCT/NO2008/000408 NO2008000408W WO2009064195A2 WO 2009064195 A2 WO2009064195 A2 WO 2009064195A2 NO 2008000408 W NO2008000408 W NO 2008000408W WO 2009064195 A2 WO2009064195 A2 WO 2009064195A2
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group
atom
carbon atoms
oxygen atom
unsaturated
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PCT/NO2008/000408
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WO2009064195A3 (fr
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Kjell-Arne Rorvik
Magny Thomassen
Henriette Alne
Rolf Kristian Berge
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Thia Medica As
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Priority to EP08848926A priority Critical patent/EP2219636A2/fr
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Publication of WO2009064195A3 publication Critical patent/WO2009064195A3/fr
Priority to NO20100744A priority patent/NO20100744L/no

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to the use of a compound for the preparation of a nutritional and/or pharmaceutical composition for inhibiting of sexual maturation of a fish.
  • Precocious sexual maturation has been, and still is, a problem in intensive farming of several different fish species, such as tilapia (Oreochromis niloticus ), Atlantic cod (Gadus Morhua), Atlantic halibut (Hippoglossus hippoglossus), European sea bass (Dicentrarchus labrax) and the salmonides, e.g. rainbow trout (Oncorhynchus mykiss) and Atlantic salmon (Salmo salar).
  • tilapia Ocean Morhua
  • Atlantic halibut Atlantic halibut
  • European sea bass European sea bass
  • the salmonides e.g. rainbow trout (Oncorhynchus mykiss) and Atlantic salmon (Salmo salar).
  • Farmed Atlantic salmon may mature sexually in freshwater (parr maturation), first autumn in sea (jack maturation), second autumn in sea (grilse maturation) or after two or more sea winters.
  • the term "early sexual maturation” in commercial on- growing production refers to fish getting sexual mature either during first or second autumn in sea.
  • Intrinsic biological factors influencing the time of first maturity in Atlantic salmon include growth rate, size and age at smolting and the status of the endocrine regulators of development. The external factors influencing these regulators are called extrinsic biological factors and include for instance food supply and competition for food.
  • a first aspect of the present invention thus relates to the use of a non beta- oxidable compound selected from;
  • R'- X-(CH 2 ) 2n +i-COOR a compound represented by the general formula R'- X-(CH 2 ) 2n +i-COOR", wherein X is a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group, a SO group or a SO 2 group; n is an integer of 0 to 11 ; and 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; or
  • R1 , R2, and R3 each independently represent i) a hydrogen atom; or H) a group having the formula CO-R in which R is a linear or branched alkyl group, saturated or unsaturated, optionally substituted, and the main chain of said R contains from 1 to 25 carbon atoms; or iii) a group having the formula CO-(CH 2 WrX-R', wherein X is a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group, a SO group or a SO 2 group; n is an integer of 0 to 11 ; and 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
  • A1 , A2 and A3 are chosen independently and represent an oxygen atom, 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; wherein R1 , R2, and R3 represent i) a hydrogen atom or a linear or branched alkyl group, saturated or unsaturated, optionally substituted, containing from 1 to 23 carbon atoms; or ii) a group having the formula CO-R in which R is a linear or branched alkyl group, saturated or unsaturated, optionally substituted, and the main chain of said R contains from 1 to 25 carbon atoms; or iii) a group having the formula CO-(CH 2 )2n+i-X-R', wherein X is a sulphur atom, a selenium atom, an oxygen atom, a CH 2 group
  • R1 , R2, and R3 are chosen independently from i), ii), iii), or iv), but at least one of R1 , R2, or R3 is defined by iii); or
  • the reduced sexual maturation is obtained without any influence on the growth rate.
  • the compound is administered to the fish orally, i.e. as a component of a feed material.
  • Preferred aspects of the invention relates to all kind of fish where an early sexual maturation will influence the growth and health characteristics of the fish. More preferable said fish is selected from the group comprising tilapia, Atlantic cod, Atlantic halibut, European sea bass and salmonides. A preferred embodiment of the invention relates to inhibiting the sexual maturation of Atlantic salmon and rainbow trout.
  • a further preferred embodiment relates to the inhibition of parr maturation, jack maturation and/or grilse maturation.
  • a preferred aspect relates to a feeding period of about 3 weeks, or about six weeks, where the feed composition contains about 0.25% of the compound of the present invention, or about 0.5% of the compound of the present invention, or about 1.0% of the compound of the present invention, or about 1.5% of the compound of the present invention.
  • a preferred aspect relates to feeding of fish where the fish is given an amount of the compound of the present invention corresponding to about 0.05% to 0,5%, related to the weight of the total biomass, or more preferable 0.1 % to 0.25%, related to the weight of the total biomass.
  • 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.
  • X is a sulphur or 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, most preferably comprising at least one tetradecylthioacetic acid (TTA), such as preferable one TTAs, more preferable two TTAs and most preferable three TTAs.
  • TTA tetradecylthioacetic acid
  • said compound is a diacylglycerol.
  • said compound is a monoacylglycerol.
  • said compound is a non ⁇ -oxidizable fatty acid.
  • said compound is the phosphatidyl choline derivative 1 ,2-ditetradecylthioacetoyl-sn- glycero-3-phosphocholine.
  • said compound is the phosphatidyl ethanolamine derivative 1 ,2-ditetradecylthioacetoyl- sn-glycero-3-phosphoethanolamine.
  • 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'- X-(CH 2 WrCOOR". However, 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 analogues 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. Multiple sulphur atoms
  • 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 the 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.
  • 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 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 C1-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, glycerocarbohyd rates, gangliosiedes, and cerebrosides.
  • X is a sulphur atom
  • the thio-substituted compound used according to the present invention may be prepared by the general procedure indicated below:
  • TTA tetradecylthioaceticacid
  • X is a selenium atom: the seleno-substituted compound used according to the present invention may be prepared by the following general procedure
  • This compound was purified by carefully crystallisation from ethanol or methanol.
  • Alkyl-Se " + Hal-CH 2 .COOH > Alkyl-Se-CH 2 - COOH
  • the final compound e.g. when alkyl is tetradecyl, (CH3-(CH2)i3-Se-CH2-COOH (tetradecylselinioacetic acid (TSA)) can be purified by crystallisation from diethyl ether and hexane.
  • the dose level of 500 mg/kg/day also elicited body weight loss. There was no evidence of toxicity at dose levels of 50 or 500 mg/day/kg.
  • TTA and TSA did not induce mutations in strains of Salmonella typhimurium and Escherichia coli. Furthermore, TTA was not mutagenic when tested in mouse lymphoma cells and L5178Y.
  • TSA and TSA were found not to be mutagenic in these tests.
  • TSA and TTA have been tested for chromosomal aberrations in cultured Chinese hamster ovary cells and no aberrations were induced by the doses tested (12-140 mg/ml).
  • the compounds of the present invention are therefore potentially useful as pharmaceutical or nutritional compounds in this respect.
  • the compound of the present invention can be given or administered to the fish in any way, although to present the compound in the feed composition is the most preferred administration route.
  • the total effective amount of the compounds according to the invention administered in the feed will preferably be in the range of about 1 mg/kg/day to 2g/kg/day of total body weight.
  • a dose of 5 - 500 mg/kg/day is preferable, while a dose of 50-100 mg/kg/day is most preferable.
  • the amount of compounds according to the invention present in the feed should be between 0.005 % and 5 % of the total weight of the feed, preferably between 0.05 % and 1 %, more preferably between 0.1 % and 0.5 %, most preferably 0.5 % of the total weight of the feed.
  • the feed may contain any amount of fat common in fish feed. But the feed should preferably be optimized by being energy rich, that is, it should preferably comprise fairly high levels of fat, at least 15 % by weight, preferably 15 % - 45 %, more preferably 20 % - 40 % fat by weight. The exact preference will of course vary with different fish species. However, a high fat content is not required for the compounds according to the invention to work, but it will most likely enhance their effect.
  • the given daily amounts should of course be the total daily amounts in the total feed consumed, and the percentages of the compounds according to the invention and the percentages of fats should also be for the total amounts of feed.
  • the percentages by weight of both compounds according to the invention and fats may greatly exceed the percentages given above, up to a feed comprised entirely of fats (therein included the compounds according to the invention).
  • the feed is used as a supplementary feed in addition to another feed(s), it may be administered to the fish separately from said another feed(s), or at the same time, or mixed with said another feed(s), as an example any conventional feed can be sprayed or soaked with a mixture of fat (preferably in liquid form) and a compound according to the invention, to thus obtain a feed according to the present invention.
  • TTA tetradecylthioacetic acid
  • the compounds of the present invention are blocked in various positions and cannot be beta-oxidised. Without being bound by theory, we believe that this inhibited ⁇ -oxidation will lead to an accumulation of fatty acids in the cell, and this accumulated amount will function as a positive feedback mechanism to increased the ⁇ -oxidation of normal fatty acids.
  • Figure 1 shows a schematic overview of restocking of fish from each of the pens in period 1 to six pens in period 2. All pens in period 2 contained 2x75 fish from each of the four pens in period 1. (Data from example 1 )
  • Figure 2 shows the mean frequency of sexually mature males at the sampling time in September for salmon fed experimental diets for three and six weeks, or twelve weeks after sea transfer. The experimental diets are further described in table I and table II. Significant differences between dietary groups within samplings (mean of three and six weeks, or twelve weeks of feeding) are indicated by different letters on the bars and variation is given as standard error of means (sem). (Data from example 1 )
  • Figure 3 shows the relationship between weeks on experimental diet and relative percent maturation compared to control diet. Closed squares ( ⁇ ) represent the estimated zero point (see text), open circles (o) represent sea cage 1 and closed circles (•) represent sea cage 4, both were fed the TTA-supplemented diet. A curve linear regression line was best fitted to the data with the corresponding equation given in the figure. Statistics evaluating the dietary effect within each sampling time (3, 6 or 12 weeks) are shown in the boxes on the top of the figure. (Data from example 1 )
  • the fish used were Atlantic salmon 1 + smolt hatched in Desember 2004 (Marine Harvest, Sl ⁇ rdal). The fish was individually marked with Pit tag approximately three months prior sea transfer. On 19 May 2006 the fish were transferred to AKVAFORSK seawater research station at Aver ⁇ y on the west coast of Norway. Seawater temperature at transfer was 9.2 0 C and mean body weight was 104 grams. On arrival to the sea site the fish were distributed in four net pens (5x5x5m) with 1100 fish in each. The fish were fed two different diets. The different diets were: a control diet and a diet supplemented with 0.5% TTA (Table I). The fish were fed these diets for three, six or twelve weeks after sea transfer (period 1 ).
  • the 12-weeks group was not included in the overall statistics on absolute growth and sexual maturation presented in the O CJ CN results.
  • the 12 weeks group are comparable to those restocked after 3 or 6 weeks.
  • the different dietary groups within the 12 weeks period are directly coO C O O mparable, since the same procedure was followed during restocking for all pens.
  • TTA was synthesized as described in Moya-Falc ⁇ n et al. (2004) Table Il Chemical content of feed (low- and high-fat diet) given during period 2.
  • the growth period was calculated from the end of period 1 until the sampling in September.
  • the initial weight was therefore measured with a three week difference for the fish fed for 3 or 6 weeks during period 1.
  • For the 12-weeks group the initial weight was measured after six weeks of feeding experimental diets in period 1 , together with the last group restocking.
  • Fat content in muscle measured after three, six, nine or twelve weeks after sea transfer on control diet or on diets supplemented with TTA.
  • TTA reduces body fat reserves in Atlantic salmon, which seems to be important for whether the fish decide to mature or not. Reduced incidence of sexual maturation in the present study may therefore, at least partly, be explained by the effect TTA is found to have on body fat reserves.
  • TTA feeding Duration of TTA feeding was found to reduce the maturity rate in a curve-linear relationship, with the most marked decrease observed as a result of the first weeks of feeding, and then the reduction levels off.
  • the present study was, however, not designed to evaluate whether this is due to the duration or the timing of feeding.
  • Fat content in muscle was found to decrease in both dietary groups until nine weeks after sea transfer (table III), but the decrease was most pronounced in TTA fed smolts. This general decrease in fat content may explain why the proportion of mature fish was low also in the control group.
  • the reduction in muscle fat for the TTA-group was found more extensive when TTA was fed for nine weeks compared with six weeks.
  • TTA a dietary supplementation of TTA resulted in an up to threefold reduction in incidence of sexual mature post-smolt male Atlantic salmon.
  • the relationship between relative reduction in maturation and weeks of feeding TTA was found to be curve-linear with the most pronounced decrease in maturation following the first weeks of feeding.
  • the observed effect on maturation is probably due to a TTA effect on reducing the fish body fat reserves, resulting in too low energy status to start the maturation process.
  • the good growth potential was maintained using TTA as a dietary supplement.

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Abstract

La présente invention concerne un procédé permettant d'inhiber la maturation sexuelle de poissons, ou l'utilisation d'un composé pour la préparation d'une composition nutritionnelle et/ou pharmaceutique permettant l'inhibition de la maturation sexuelle d'un poisson.
PCT/NO2008/000408 2007-11-15 2008-11-17 Maturation sexuelle réduite chez des poissons WO2009064195A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP08848926A EP2219636A2 (fr) 2007-11-15 2008-11-17 Maturation sexuelle réduite chez des poissons
NO20100744A NO20100744L (no) 2007-11-15 2010-05-21 Redusert kjonnsmodning i fisk

Applications Claiming Priority (2)

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NO20075894 2007-11-15
NO20075894A NO20075894L (no) 2007-11-15 2007-11-15 Redusert kjonnsmodning i fisk

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WO2009064195A3 WO2009064195A3 (fr) 2009-08-27

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010062189A1 (fr) * 2008-11-28 2010-06-03 Pronova Biopharma Norge As Composition, avec/sans au moins un composant facilement oxydé, comprenant une huile traitée comestible ou un mélange de graisse, pour favoriser la croissance chez un animal, empêcher le stress oxydatif, éviter qu'un poisson ne développe un foie hypertrophié et composition alimentaire
CN112244178A (zh) * 2020-08-28 2021-01-22 盐城工学院 一种降低异育银鲫越冬减重和繁殖减重的配合饲料

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