WO2023280891A1 - Novel use of natural phenolic substances - Google Patents
Novel use of natural phenolic substances Download PDFInfo
- Publication number
- WO2023280891A1 WO2023280891A1 PCT/EP2022/068660 EP2022068660W WO2023280891A1 WO 2023280891 A1 WO2023280891 A1 WO 2023280891A1 EP 2022068660 W EP2022068660 W EP 2022068660W WO 2023280891 A1 WO2023280891 A1 WO 2023280891A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenolic substances
- animals
- nitrogen
- natural phenolic
- group
- Prior art date
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- 239000000126 substance Substances 0.000 title claims abstract description 51
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 129
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 67
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- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
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Classifications
-
- 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
- A23K10/00—Animal feeding-stuffs
- A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
-
- 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
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
Definitions
- the present invention relates to a novel use of one or more natural phenolic substances in animals, such as ruminants.
- phenolic substances such as essential oils have been proved as alternatives to antibiotics because they have antimicrobial, anti-inflammatory, antioxidative and coccidiostatic properties. They enhance digestibility and immunity, promote gut health by minimizing the effect of the pathogenic bacteria, and control odor and ammonia emission.
- examples of the commonly used natural phenolic substances in animals are carvacrol, thymol and eugenol. (F.A. Omonijo et oL, Animal Nutrition 4 (2016) 126-136)
- At least one natural phenolic substance has the advantage of being able to improve nitrogen use efficiency (NUE), increase nitrogen retention, decrease nitrogen excretion in manure, and/or increase microbial protein production in animals.
- NUE nitrogen use efficiency
- the NUE as used herein represents the individual efficiency of dairy animals such as cows in transforming feed nitrogen into milk nitrogen, which is defined as the ratio of grams of nitrogen in milk to grams of nitrogen intake.
- a low NUE is basically due to the incapacity of animals to build significant amounts of protein reserves, being necessary to adjust protein supply according to protein requirements. The most efficient strategy to improve NUE under these conditions seems to be to reduce dietary crude protein content through supplementation with low-protein concentrate feeds.
- Nitrogen retention as used herein means animals' ability to retain nitrogen from the diet as body mass. A negative nitrogen balance occurs when the excretion of nitrogen exceeds the daily intake and is often seen when the muscle is being lost. A positive nitrogen balance is often associated with muscle growth, particularly in growing animals. Nitrogen retention may be measured as the difference between the intake of nitrogen and the excreted nitrogen by means of the total collection of milk, faeces and urine during a period of time. It is understood that an animal should have increased nitrogen retention if it has less excreted nitrogen in milk, faeces and urine compared to the control animal which has same nitrogen intake.
- Nitrogen excretion in manure as used herein can be represented by the total excreted nitrogen in faeces and urine. Reducing the amount of nitrogen excretion in manure is positive on reducing environmental pollution.
- Microbial proteins are very beneficial to animals, especially ruminants.
- Dietary protein includes nitrogen (N) occurring in true protein and non-protein.
- N nitrogen
- the true protein is degraded into amino acid and ammonia and then utilized by ruminal microorganisms to synthesize microbial protein.
- rumen microbial protein provides all of the amino acids needed for milk protein synthesis. Because of the high digestibility and good amino acid composition of microbial protein, increasing the microbial protein yield in the rumen is of important significance for the promotion of animal performance.
- Microbial protein production in the rumen can be estimated according to manual provided by IAEA-TECDOC-945 (Estimation of rumen microbial protein production from purine derivatives in urine, published in 1999). Accordingly, the present invention provides use of one or more natural phenolic substances, such as essential oils, for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals, such as ruminants.
- NUE nitrogen use efficiency
- the present invention also provides a method for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals, comprising administering to the animals one or more natural phenolic substances, such as essential oils.
- NUE nitrogen use efficiency
- the natural phenolic substances according to the present invention are a well-known group of compounds found in nature (i.e. naturally occurring phenolic compounds) which are characterized by their structures comprising at least one phenol unit.
- R 3 is selected from the group consisting of H, -OH, Ci-salkyl, C2-salkenyl and Ci-salkoxy, preferably selected from H, -OH, methyl, isopropyl, methoxy, isoamyl and allyl; and
- R 4 is selected from the group consisting of Ci-salkyl and Ci-salkylphenyl, preferably from benzyl, B-methyl-2-butanyl and isoamyl, as well as tannic acid.
- 'Ci-salkyl' refers to monovalent straight chain or branched, saturated, acyclic hydrocarbyl groups having up to 5 carbon atoms.
- Preferred alkyl residues in the present invention are methyl, ethyl, n-propyl, i-propyl, isoamyl or i-, n-, secondary or t-butyl groups.
- C2-salkenyl refers to monovalent straight or branched alkyl chains having from 2 to 5 carbon atoms and which have at least one carbon-carbon double bond, which may be (independently from each other) in (E) or (Z)-configuration.
- the C2-salkenyl group is selected from the group of linear (straight chain) alkenyl groups, such as in particular linear C2-4alkenyl groups, most preferably the C2-salkenyl group is allyl.
- alkoxy' is used herein to refer an -O-alkyl group with all the definitions for alkyl as given above, such as in particular methoxy (-OMe) or ethoxy (-OEt), most preferably methoxy.
- 'Ci-salkylphenyl' is used herein to refer to a -(G-l 2 )i- 5 phenyl residue such as preferably benzyl (i.e., -(G-l 2 )phenyl).
- At least one of R 1 , R 2 and R 3 is not H.
- the natural phenolic substances according to the present invention are selected from the group consisting of 3-hydroxyphenol (CAS No.: 108-46-3), 2- methoxyphenol (CAS No.: 90-05-1), 3-methylphenol (CAS No.: 108-39-4), 2-(l- methylethyl)-5-methyl-phenol (CAS No.: 89-83-8), 4-allyl-2-methoxyphenol (CAS No.: 97- 53-0), 4-hydroxy-3-methoxybenzaldehyde (CAS No.: 121-33-5), 5-isopropyl-2- methylphenol (CAS No.: 499-75-2), 2-hydroxybenzoates (salicylates) and tannic acid (CAS No.: 1401-55-4).
- Preferred salicylates in the present invention are methyl, ethyl, isoamyl and benzyl salicylates. More preferred salicylates in the present invention are benzyl salicylate (CAS No.: 118-58-1) and/ or isoamyl salicylate (CAS No.: 87-20-7) such as in particular a mixture of both.
- the one or more natural phenolic substances according to the present invention are a mixture of at least six, preferably all phenolic substances selected from the group consisting of 3-hydroxyphenol, 2-methoxyphenol, 3-methylphenol, 2-(l- methylethyl)-5-methyl-phenol, 4-allyl-2-methoxyphenol, 4-hydroxy-3- methoxybenzaldehyde, tannic acid and at least one 2-hydroxybenzoates (salicylates) such as preferably benzyl and/ or isoamyl salicylate, more preferably benzyl and isoamyl salicylate.
- salicylates such as preferably benzyl and/ or isoamyl salicylate, more preferably benzyl and isoamyl salicylate.
- the natural phenolic substances according to the present invention can be in highly purified forms or in the form of (e.g. comprised in) natural available plant extracts or extract-mixtures.
- extract as used in this context of the present invention includes compositions obtained by solvent extraction (which are also known as “extracted oils”), steam distillation or other methods known to the skilled person.
- Suitable extraction solvents include alcohols such as ethanol or supercritical carbon dioxide.
- natural in this context of the present invention is to be understood to refer to a substance or a composition (mixture) of substances which are occurring in nature and which are obtained from natural products or through synthesis.
- the natural phenolic substances according to the present invention are commercially available or can be prepared by a skilled person using processes and methods well-known in the art.
- An example of the natural phenolic substances is the commercial product name Crina ® Ruminants (available from DSM Nutritional Products AG, Switzerland).
- Crina ® Ruminants is a blend of essential oil compounds for animal nutrition.
- the one or more natural phenolic substances according to the present invention may be administered admixed together (i.e. premixed) or separately to the animal, while in the latter case it is well understood that the administration of the natural phenolic substances (separately or, preferably, admixed) occurs within a limited time window, i.e. within at most 6 h, preferably within S h, more preferably within 1 h , such as within 0.5 h. Most preferably, if administered separately, all ingredients are concomitantly administered to the animal e.g. by concomitant addition thereof into the animal's feed/ diet or into the feed rack.
- the one or more natural substances according to the present invention are administered in the absence of (i.e. not concomitantly with) any antibiotic such as preferably monensin, one or more p- nitroaniline derivative such as p-nitroaniline, and/ or one or more fatty acid derivative containing at least 5 carbon atoms such as lauric acid.
- any antibiotic such as preferably monensin, one or more p- nitroaniline derivative such as p-nitroaniline, and/ or one or more fatty acid derivative containing at least 5 carbon atoms such as lauric acid.
- the one or more natural phenolic substances are administered to animals such as ruminants in an effective amount.
- an effective amount refers to an amount necessary to achieve at least one of the effects of improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and increasing microbial protein production, preferably by at least 1 %, more preferably of at least 2 %, most preferably of at least 3 %, such as even of at least 4 %, in the animals supplemented with the natural phenolic substances according to the present invention, when compared to control, i.e. to animals not supplemented with the natural phenolic substances.
- NUE nitrogen use efficiency
- the effective amount (total amount) of the one or more natural phenolic substances according to the present invention is selected in the range of from 0.1 to 150 mg/kg body weight per day, preferably 1 to 150 mg/ kg body weight per day, more preferably 50 to 150 mg per kg body weight per day, such as 70 mg to 120 mg per kg body weight per day.
- the one or more natural phenolic substances according to the invention may be formulated in the form of a feed composition or a feed additive (premix) for administering to animals.
- feed composition or feed additive as used herein means any preparation, mixture, or composition suitable for, or intended for oral intake by an animal.
- the present invention also provides a feed composition or a feed additive comprising one or more natural phenolic substances as defined above for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals, such as ruminants
- the natural phenolic substances may be contained in a total amount of from 10 wt% to 80 wt%, preferably from 20 wt% to 60 wt%, more preferably from 30 wt% to 50 wt%, and the most preferably from 38 wt% to 42 wt%, based on the weight of the feed composition or the feed additive of the present invention.
- 2-hydroxybenzoates preferably a mixture of benzyl salicylate and isoamyl salicylate, between 1 wt% and 5 wt%, preferably 2 wt% and 4 wt%; and/or
- the feed composition or the feed additive according to the present invention may also contain, preferably in minor amounts, other natural (fragrance) substances, preferably selected from the following group, and in amounts as indicated based on the weight of the composition or the feed additive of the present invention:
- the feed composition or the feed additive according to the present invention contains up to about 5 wt%, preferably up to 3 wt% of limonene, anethol, and/or linalool.
- the feed composition or the feed additive of the present invention may further contain at least one carrier and an antioxidant.
- Suitable carriers to be used in the feed composition or the feed additive of the present invention encompass silicon dioxide (silica), proteins as well as plant fibres and middlings without being limited thereto. Said carriers are generally present in amounts of 40 wt% to 60 wt%, based on the total weight of the composition of the present invention.
- Suitable antioxidants to be used in the feed composition or the feed additive of the present invention encompass BHT (Butylated hydroxytoluene), BHA (butylated hydroxyanisode), tocopherol or derivatives thereof as well as vitamin C or derivatives thereof.
- BHT Butylated hydroxytoluene
- BHA butylated hydroxyanisode
- tocopherol or derivatives thereof as well as vitamin C or derivatives thereof.
- the antioxidants are generally used in amounts up to 2 wt%, based on the total weight of the composition of the present invention.
- the feed composition or the feed additive of the present invention may contain an emulsifying surfactant, which can be selected advantageously from those of a rather hydrophilic nature, for example among polyglycerol esters of fatty acids such as esterified ricinoleic acid or propylene glycol esters of fatty acids, saccharo-esters or saccharo-glycerides, polyethylene glycol, lecithins etc.
- an emulsifying surfactant which can be selected advantageously from those of a rather hydrophilic nature, for example among polyglycerol esters of fatty acids such as esterified ricinoleic acid or propylene glycol esters of fatty acids, saccharo-esters or saccharo-glycerides, polyethylene glycol, lecithins etc.
- the feed composition or the feed additive of the present invention may also contain at least one fat-soluble vitamin, and/or at least one water soluble vitamin, and/or at least one trace mineral, and/or at least one macro mineral.
- fat-soluble vitamins are vitamin A, vitamin D3, vitamin E, and vitamin K.
- water-soluble vitamins are vitamin B12, biotin and choline, vitamin Bi, vitamin B2, vitamin Be, niacin, folic acid and panthothenate, e.g. Ca-D-panthothenate.
- trace minerals are manganese, zinc, iron, copper, iodine, selenium, manganese, and cobalt.
- macro minerals are calcium, phosphorus, potassium, magnesium and sodium.
- the feed composition or the feed additive of the present invention may comprise 0.5 to 10% by weight of the active ingredients (i.e. the one or more natural phenolic substances of the present invention) and 10 to 95% by weight of other conventional additives, such as flavorings, vitamins, mineral salts and any conventional absorbing support.
- the one or more natural phenolic substances and the feed composition or the feed additive according to the present invention may be finally incorporated into an animal feed.
- the present invention further provides an animal feed which comprises the one or more natural phenolic substances according to the invention, the feed composition or the feed additive as defined above for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
- NUE nitrogen use efficiency
- the animal feed according to the present invention is a ruminant feed (often also referred to as ruminant diet) where all the dietary components, e.g. macro and micro ingredients, forage, silage and concentrate feed and additives including the one or more natural phenolic substances are included.
- ruminant feed or diet is also often referred to as total mixed ration (TMR) or partial mixed ration (PMR) or nutritional supplement for grazing animals.
- the total amount of the one or more natural phenolic substances is selected in the range from 10 mg to about 500 mg per kg dry matter feed, preferably from about 10 mg to about 250 mg per Kg dry matter feed, more preferably from 10 mg to 100 mg per Kg of dry matter feed. Further particular suitable ranges are from 10 mg to 75 mg per Kg of dry matter feed or 20 mg to 50 mg per Kg of dry matter feed.
- the animals may be fed with a normal protein diet or a low protein diet.
- the animals are feed with a low protein diet.
- the term "normal protein diet” means a diet or feed containing all necessary ingredients including proteins in a sufficient or surplus amount for the health and growth of animals.
- the term “low protein diet” means a diet or feed containing all necessary ingredients for the health and growth of animals, wherein proteins are contained in a insufficient amount or in a less amount compared to the normal protein diet for the health and growth of animals.
- diets for nursing calves should contain at least 16wt% crude protein, so a diet containing less than 16wt% crude protein should be a low protein diet.
- the low protein diet for ruminant such as cattle contains less than 16.5wt%, preferably less than 16wt%, more preferably less than 15.5wt% crude protein.
- the present invention provides use of the one or more natural phenolic substances as defined above in a low protein diet for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
- NUE nitrogen use efficiency
- the present invention provides use of the one or more natural phenolic substances as defined above in a normal protein diet or in a low protein diet for improving nitrogen use efficiency (NUE) in animals.
- NUE nitrogen use efficiency
- animal in this context of the present invention includes all animals, and preferably ruminants, which include but are not limited to sheep, goat, cattle, e.g. cow such as beef cattle and dairy cows, giraffes, American Bison, European bison, yaks, water buffalo, deer, camels, alpacas, llamas, wildebeest, antelope, pronghorn, and Nilgai.
- the animal is a ruminant animal such as domestic cattle, sheep and goat. More preferably, the animal is cattle such as dairy cows and beef cattle. It is well understood that the term dairy cows and beef cattle encompasses animals in all ages and physiological stage of life and production systems such as confined, semi-confined and grazing.
- the trial consisted of a randomized arrangement of 90-95 lactating cows in two stages. In stage 1, all the cows were fed with the same diet for the first four weeks, considered as "control normal protein" (CNP). In stage 2 of a second four weeks, the 90-95 cows from stage 1 were split into 3 groups of 22-23 cows as: 22-23 cows with usual protein diet plus EO blend (Crina ® Ruminants: Normal Protein Crina, NPC); 22-23 cows low protein diet (Control low protein, CLP); 22-23 cows low protein diet plus essential oils (EO) blend (Crina ® Ruminants: Low Protein Crina, LPC). Treatments were offered though 2 kg of robot feed containing Crina ® Ruminants at 0.5 g/kg, and control was fed with the same feed without Crina ® Ruminants. The basal diets for the four groups are indicated in Tables 1.
- Urinary purine derivatives including xanthine, hypoxanthine, uric acid and allantoin
- creatinine were determined following the procedure described by Balcells et ai., J. Chromatogr. 1992, 575:153-157), using HPLC analysis. PD and creatinine were quantified by peak integration using the Waters HPLC systems Empower2 software using Allopurinol as internal standard (with known concentration).
- a subsample from the thawed urine was taken to measure the nitrogen (N) content using an elemental Leco TruSpec CN analyzer.
- creatinine concentration in urine samples is used to estimate total urine volume produced per animal and day.
- the model used assumes urinary excretion of 29 mg Creatinine/kg BW (body weight) when there is no change in body weight (Valadares et al., J. Dairy Sci. 1999, 82: 2686-2696;
- Nitrogen excretion Table 3 shows the effect of the different treatments on N excretion in urine, faeces and milk.
- the reduction in N intake as a result of lowering the protein level in the diet promoted significantly lower N content in urine and as % of the total N intake and therefore the overall N excretion (CNP1 vs CLP).
- the addition of Crina ® Ruminants in low protein treatment significantly decreases faeces N, and increased nitrogen retention, decreased excretion of N in manure (CLP vs LPC).
- Crina ® Ruminants to the normal protein diet (NPC) also promoted a significant reduction on both the urinary N content and the N excretion in manure in relation to total N intake.
- Crina ® Ruminants in the diet of dairy cows substantially improved the nitrogen use efficiency, increased nitrogen retention, decreased nitrogen excretion in manure, and increased microbial protein production.
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Abstract
The present invention relates to a novel use of one or more natural phenolic substances for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
Description
Novel use of natural phenolic substances
The present invention relates to a novel use of one or more natural phenolic substances in animals, such as ruminants.
Nature phenolic substances such as essential oils have been proved as alternatives to antibiotics because they have antimicrobial, anti-inflammatory, antioxidative and coccidiostatic properties. They enhance digestibility and immunity, promote gut health by minimizing the effect of the pathogenic bacteria, and control odor and ammonia emission. Examples of the commonly used natural phenolic substances in animals are carvacrol, thymol and eugenol. (F.A. Omonijo et oL, Animal Nutrition 4 (2018) 126-136)
The effects of dietary supplementation containing a mixture of thymol and carvacrol has been evaluated. It is concluded that feed supplementation with thymol and carvacrol enhanced performance, increased antioxidant enzyme activities, retarded lipid oxidation, enhanced digestive enzyme activities and improved immune response of broilers (see: H. Hashemipour, et at., Poultry Science 2013, 92 :2059-2069).
It has now been found surprisingly that in addition to the above functions, at least one natural phenolic substance has the advantage of being able to improve nitrogen use efficiency (NUE), increase nitrogen retention, decrease nitrogen excretion in manure, and/or increase microbial protein production in animals.
The NUE as used herein represents the individual efficiency of dairy animals such as cows in transforming feed nitrogen into milk nitrogen, which is defined as the ratio of grams of nitrogen in milk to grams of nitrogen intake. A low NUE is basically due to the incapacity of animals to build significant amounts of protein reserves, being necessary to adjust protein supply according to protein requirements. The most efficient strategy to improve NUE under these conditions seems to be to reduce dietary crude protein content through supplementation with low-protein concentrate feeds.
Nitrogen retention as used herein means animals' ability to retain nitrogen from the diet as body mass. A negative nitrogen balance occurs when the excretion of nitrogen exceeds the daily intake and is often seen when the muscle is being lost. A positive nitrogen balance is often associated with muscle growth, particularly in growing animals. Nitrogen retention may be measured as the difference between the intake of nitrogen and the excreted nitrogen by means of the total collection of milk, faeces and urine during a period of time. It is understood that an animal should have increased nitrogen retention if it has less excreted nitrogen in milk, faeces and urine compared to the control animal which has same nitrogen intake.
Nitrogen excretion in manure as used herein can be represented by the total excreted nitrogen in faeces and urine. Reducing the amount of nitrogen excretion in manure is positive on reducing environmental pollution.
Microbial proteins are very beneficial to animals, especially ruminants. Dietary protein includes nitrogen (N) occurring in true protein and non-protein. In the rumen, the true
protein is degraded into amino acid and ammonia and then utilized by ruminal microorganisms to synthesize microbial protein. In the small intestine, more than 80% of rumen microbial protein is digested, accounting for 50-80% of the total absorbable protein contained there. In dairy cows, rumen microbial protein provides all of the amino acids needed for milk protein synthesis. Because of the high digestibility and good amino acid composition of microbial protein, increasing the microbial protein yield in the rumen is of important significance for the promotion of animal performance. Moreover, increasing the microbial protein yield is the most effective strategy to reduce the protein feed waste in livestock, since the dietary protein that exceeds the requirement of ruminal microorganisms is degraded to ammonia in the rumen, metabolized to urea in the liver, and lost in the urine. Microbial protein production in the rumen can be estimated according to manual provided by IAEA-TECDOC-945 (Estimation of rumen microbial protein production from purine derivatives in urine, published in 1999). Accordingly, the present invention provides use of one or more natural phenolic substances, such as essential oils, for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals, such as ruminants. The present invention also provides a method for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals, comprising administering to the animals one or more natural phenolic substances, such as essential oils. The natural phenolic substances according to the present invention are a well-known group of compounds found in nature (i.e. naturally occurring phenolic compounds) which are characterized by their structures comprising at least one phenol unit.
Preferably the natural phenolic substances according to the present invention are compounds of formula (I)
formula (I) wherein R1 is selected from the group consisting of H, Ci-salkyl, Ci-salkoxy and -C(=0)0R4, preferably selected from H, methyl, isopropyl, isoamyl, methoxy, -C(=0)0-benzyl and -C(=0)0-isoamyl;
R2 is selected from the group consisting of H, Ci-salkyl, C2-salkenyl and -C(=0)H, preferably selected from H, methyl, allyl and -C(=0)H; R3 is selected from the group consisting of H, -OH, Ci-salkyl, C2-salkenyl and Ci-salkoxy, preferably selected from H, -OH, methyl, isopropyl, methoxy, isoamyl and allyl; and
R4 is selected from the group consisting of Ci-salkyl and Ci-salkylphenyl, preferably from benzyl, B-methyl-2-butanyl and isoamyl,
as well as tannic acid.
The term 'Ci-salkyl' as used herein refers to monovalent straight chain or branched, saturated, acyclic hydrocarbyl groups having up to 5 carbon atoms. Preferred alkyl residues in the present invention are methyl, ethyl, n-propyl, i-propyl, isoamyl or i-, n-, secondary or t-butyl groups.
The term 'C2-salkenyl' as used herein refers to monovalent straight or branched alkyl chains having from 2 to 5 carbon atoms and which have at least one carbon-carbon double bond, which may be (independently from each other) in (E) or (Z)-configuration. Preferably, in the present invention, the C2-salkenyl group is selected from the group of linear (straight chain) alkenyl groups, such as in particular linear C2-4alkenyl groups, most preferably the C2-salkenyl group is allyl. The term 'alkoxy' is used herein to refer an -O-alkyl group with all the definitions for alkyl as given above, such as in particular methoxy (-OMe) or ethoxy (-OEt), most preferably methoxy.
The term 'Ci-salkylphenyl' is used herein to refer to a -(G-l2)i-5phenyl residue such as preferably benzyl (i.e., -(G-l2)phenyl).
It is furthermore preferred, in the present invention, at least one of R1, R2 and R3 is not H.
More preferably, the natural phenolic substances according to the present invention are selected from the group consisting of 3-hydroxyphenol (CAS No.: 108-46-3), 2- methoxyphenol (CAS No.: 90-05-1), 3-methylphenol (CAS No.: 108-39-4), 2-(l- methylethyl)-5-methyl-phenol (CAS No.: 89-83-8), 4-allyl-2-methoxyphenol (CAS No.: 97- 53-0), 4-hydroxy-3-methoxybenzaldehyde (CAS No.: 121-33-5), 5-isopropyl-2- methylphenol (CAS No.: 499-75-2), 2-hydroxybenzoates (salicylates) and tannic acid (CAS No.: 1401-55-4). Preferred salicylates in the present invention are methyl, ethyl, isoamyl and benzyl salicylates. More preferred salicylates in the present invention are benzyl salicylate (CAS No.: 118-58-1) and/ or isoamyl salicylate (CAS No.: 87-20-7) such as in particular a mixture of both. Most preferably, the one or more natural phenolic substances according to the present invention are a mixture of at least six, preferably all phenolic substances selected from the group consisting of 3-hydroxyphenol, 2-methoxyphenol, 3-methylphenol, 2-(l- methylethyl)-5-methyl-phenol, 4-allyl-2-methoxyphenol, 4-hydroxy-3- methoxybenzaldehyde, tannic acid and at least one 2-hydroxybenzoates (salicylates) such as preferably benzyl and/ or isoamyl salicylate, more preferably benzyl and isoamyl salicylate.
The natural phenolic substances according to the present invention can be in highly purified forms or in the form of (e.g. comprised in) natural available plant extracts or extract-mixtures.
The term "extract" as used in this context of the present invention includes compositions obtained by solvent extraction (which are also known as "extracted oils"), steam
distillation or other methods known to the skilled person. Suitable extraction solvents include alcohols such as ethanol or supercritical carbon dioxide.
The term "natural" in this context of the present invention is to be understood to refer to a substance or a composition (mixture) of substances which are occurring in nature and which are obtained from natural products or through synthesis.
The natural phenolic substances according to the present invention are commercially available or can be prepared by a skilled person using processes and methods well-known in the art. An example of the natural phenolic substances is the commercial product name Crina® Ruminants (available from DSM Nutritional Products AG, Switzerland). Crina® Ruminants is a blend of essential oil compounds for animal nutrition.
It is well understood that the one or more natural phenolic substances according to the present invention may be administered admixed together (i.e. premixed) or separately to the animal, while in the latter case it is well understood that the administration of the natural phenolic substances (separately or, preferably, admixed) occurs within a limited time window, i.e. within at most 6 h, preferably within S h, more preferably within 1 h , such as within 0.5 h. Most preferably, if administered separately, all ingredients are concomitantly administered to the animal e.g. by concomitant addition thereof into the animal's feed/ diet or into the feed rack.
In the present invention it is particularly preferred that the one or more natural substances according to the present invention are administered in the absence of (i.e. not concomitantly with) any antibiotic such as preferably monensin, one or more p- nitroaniline derivative such as p-nitroaniline, and/ or one or more fatty acid derivative containing at least 5 carbon atoms such as lauric acid.
It is well understood that in the present invention the one or more natural phenolic substances are administered to animals such as ruminants in an effective amount.
The term "an effective amount" as used herein refers to an amount necessary to achieve at least one of the effects of improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and increasing microbial protein production, preferably by at least 1 %, more preferably of at least 2 %, most preferably of at least 3 %, such as even of at least 4 %, in the animals supplemented with the natural phenolic substances according to the present invention, when compared to control, i.e. to animals not supplemented with the natural phenolic substances. Preferably, the effective amount (total amount) of the one or more natural phenolic substances according to the present invention is selected in the range of from 0.1 to 150 mg/kg body weight per day, preferably 1 to 150 mg/ kg body weight per day, more preferably 50 to 150 mg per kg body weight per day, such as 70 mg to 120 mg per kg body weight per day.
As anticipated by any person skilled in the art, the one or more natural phenolic substances according to the invention may be formulated in the form of a feed composition or a feed additive (premix) for administering to animals.
The term feed composition or feed additive as used herein means any preparation, mixture, or composition suitable for, or intended for oral intake by an animal. Accordingly, the present invention also provides a feed composition or a feed additive comprising one or more natural phenolic substances as defined above for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals, such as ruminants
In the feed composition or the feed additive of the present invention, the natural phenolic substances may be contained in a total amount of from 10 wt% to 80 wt%, preferably from 20 wt% to 60 wt%, more preferably from 30 wt% to 50 wt%, and the most preferably from 38 wt% to 42 wt%, based on the weight of the feed composition or the feed additive of the present invention.
Examples of particularly preferred dosages of the individual respectively natural phenolic substances in the feed composition or the feed additive according to the present invention are selected in the following ranges:
• 2-(l-methylethyl)-5-methyl-phenol between 7.5 wt% and 15 wt%, preferably 8 wt% and 12 wt%; and/or
• 4-allyl-2-methoxyphenol between 2 wt% and 6 wt%, preferably 2.5 wt% and 5 wt%; and/or
• 3-methylphenol between 7.5 wt% and 15 wt%, preferably 8 wt% and 12 wt%; and/or
• 4-hydroxy-3-methoxybenzaldehyde between 3 wt% and 7 wt%, preferably 4 wt% and 6 wt%; and/or
• 2-methoxyphenol between 2 wt% and 5 wt%, preferably 2.5 wt% and 4 wt%; and/or
• 2-hydroxybenzoates, preferably a mixture of benzyl salicylate and isoamyl salicylate, between 1 wt% and 5 wt%, preferably 2 wt% and 4 wt%; and/or
• 3-hydroxyphenol between 1 wt% and 3 wt%, preferably 1 wt% and 2 wt%; and/or
• tannic acid between 0.5 wt% to 15 wt%, preferably 0.75 wt% and 3 wt%, with all wt% being based on the weight of the composition or the feed additive of the present invention.
The feed composition or the feed additive according to the present invention may also contain, preferably in minor amounts, other natural (fragrance) substances, preferably selected from the following group, and in amounts as indicated based on the weight of the composition or the feed additive of the present invention:
• up to about 1 wt%, preferably up to 0.5 wt% of propylidene- and/ or butylidenephtalides, isophorones, gingerol and/ or lavender oil; and/or
• up to about 2 wt%, preferably up to about 1 wt% of deca-, undeca- and/or dodecalactones, ionones, irone, eucalyptol, menthol, peppermint oil and/ or alpha- pinene; and/or
• up to about 5 wt%, preferably up to 3 wt% of limonene, anethol, linalool and/ or methyl dihydrojasmonate; and/or
• up to about 4 wt%, preferably up to 2 wt% of propionic, acetic or butyric acid, rosemary oil, clove oil, geraniol, terpineol and/ or citronellol; and/or
• up to about 3 wt%, preferably up to 2 wt% of cinnamaldehyde and/ or a plant polyphenol (tannin); and/or
• and up to about 5 wt%, preferably up to 2 wt% of a powder of turmeric and/ or of an extract of curcuma.
Preferably, the feed composition or the feed additive according to the present invention contains up to about 5 wt%, preferably up to 3 wt% of limonene, anethol, and/or linalool.
The feed composition or the feed additive of the present invention may further contain at least one carrier and an antioxidant.
Suitable carriers to be used in the feed composition or the feed additive of the present invention encompass silicon dioxide (silica), proteins as well as plant fibres and middlings without being limited thereto. Said carriers are generally present in amounts of 40 wt% to 60 wt%, based on the total weight of the composition of the present invention.
Suitable antioxidants to be used in the feed composition or the feed additive of the present invention encompass BHT (Butylated hydroxytoluene), BHA (butylated hydroxyanisode), tocopherol or derivatives thereof as well as vitamin C or derivatives thereof. The antioxidants are generally used in amounts up to 2 wt%, based on the total weight of the composition of the present invention.
Optionally, the feed composition or the feed additive of the present invention may contain an emulsifying surfactant, which can be selected advantageously from those of a rather hydrophilic nature, for example among polyglycerol esters of fatty acids such as esterified ricinoleic acid or propylene glycol esters of fatty acids, saccharo-esters or saccharo-glycerides, polyethylene glycol, lecithins etc.
Optionally, the feed composition or the feed additive of the present invention may also contain at least one fat-soluble vitamin, and/or at least one water soluble vitamin, and/or at least one trace mineral, and/or at least one macro mineral.
Examples of fat-soluble vitamins are vitamin A, vitamin D3, vitamin E, and vitamin K.
Examples of water-soluble vitamins are vitamin B12, biotin and choline, vitamin Bi, vitamin B2, vitamin Be, niacin, folic acid and panthothenate, e.g. Ca-D-panthothenate.
Examples of trace minerals are manganese, zinc, iron, copper, iodine, selenium, manganese, and cobalt.
Examples of macro minerals are calcium, phosphorus, potassium, magnesium and sodium.
The feed composition or the feed additive of the present invention may comprise 0.5 to 10% by weight of the active ingredients (i.e. the one or more natural phenolic substances of the present invention) and 10 to 95% by weight of other conventional additives, such as flavorings, vitamins, mineral salts and any conventional absorbing support.
Any person skilled in the art should understand that, the one or more natural phenolic substances and the feed composition or the feed additive according to the present invention may be finally incorporated into an animal feed. Accordingly, the present invention further provides an animal feed which comprises the one or more natural phenolic substances according to the invention, the feed composition or the feed additive as defined above for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
In a particular embodiment the animal feed according to the present invention is a ruminant feed (often also referred to as ruminant diet) where all the dietary components, e.g. macro and micro ingredients, forage, silage and concentrate feed and additives including the one or more natural phenolic substances are included. Such ruminant feed or diet is also often referred to as total mixed ration (TMR) or partial mixed ration (PMR) or nutritional supplement for grazing animals.
Preferably, in said ruminant feed, the total amount of the one or more natural phenolic substances is selected in the range from 10 mg to about 500 mg per kg dry matter feed, preferably from about 10 mg to about 250 mg per Kg dry matter feed, more preferably from 10 mg to 100 mg per Kg of dry matter feed. Further particular suitable ranges are from 10 mg to 75 mg per Kg of dry matter feed or 20 mg to 50 mg per Kg of dry matter feed.
Any person skilled in the art are familiar with the particular recipes for making the feed for particular types of animals and can be prepared in similar formulations when adding an effective amount of the composition or the animal feed additive according to the present invention.
In the present invention, the animals may be fed with a normal protein diet or a low protein diet. Preferably, the animals are feed with a low protein diet.
In the present invention, the term "normal protein diet" means a diet or feed containing all necessary ingredients including proteins in a sufficient or surplus amount for the health and growth of animals. In contrast, the term "low protein diet" means a diet or feed containing all necessary ingredients for the health and growth of animals, wherein proteins are contained in a insufficient amount or in a less amount compared to the normal protein diet for the health and growth of animals. For example, diets for nursing calves should contain at least 16wt% crude protein, so a diet containing less than 16wt% crude protein should be a low protein diet.
In the present invention, the low protein diet for ruminant such as cattle contains less than 16.5wt%, preferably less than 16wt%, more preferably less than 15.5wt% crude protein.
In one embodiment, the present invention provides use of the one or more natural phenolic substances as defined above in a low protein diet for improving nitrogen use
efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
In another embodiment, the present invention provides use of the one or more natural phenolic substances as defined above in a normal protein diet or in a low protein diet for improving nitrogen use efficiency (NUE) in animals.
The term "animal" in this context of the present invention includes all animals, and preferably ruminants, which include but are not limited to sheep, goat, cattle, e.g. cow such as beef cattle and dairy cows, giraffes, American Bison, European bison, yaks, water buffalo, deer, camels, alpacas, llamas, wildebeest, antelope, pronghorn, and Nilgai. Preferably, the animal is a ruminant animal such as domestic cattle, sheep and goat. More preferably, the animal is cattle such as dairy cows and beef cattle. It is well understood that the term dairy cows and beef cattle encompasses animals in all ages and physiological stage of life and production systems such as confined, semi-confined and grazing.
The present invention is further described by the following examples. Examples Example 1
Experimental Design and Diets
The trial consisted of a randomized arrangement of 90-95 lactating cows in two stages. In stage 1, all the cows were fed with the same diet for the first four weeks, considered as "control normal protein" (CNP). In stage 2 of a second four weeks, the 90-95 cows from stage 1 were split into 3 groups of 22-23 cows as: 22-23 cows with usual protein diet plus EO blend (Crina® Ruminants: Normal Protein Crina, NPC); 22-23 cows low protein diet (Control low protein, CLP); 22-23 cows low protein diet plus essential oils (EO) blend (Crina® Ruminants: Low Protein Crina, LPC). Treatments were offered though 2 kg of robot feed containing Crina® Ruminants at 0.5 g/kg, and control was fed with the same feed without Crina® Ruminants. The basal diets for the four groups are indicated in Tables 1.
Table 1. Ingredient as formulated :or Normal Protein and Low Protein diets
After the adaptation to the diet spot milk, urine and feaces samples were collected over three consecutive days and froze prior testing.
Analytical methodology and calculations
Samples were thawed at 4°C, homogenized, filtrated through 50 urn pore size filter. Urinary purine derivatives (PD, including xanthine, hypoxanthine, uric acid and allantoin) and creatinine were determined following the procedure described by Balcells et ai., J. Chromatogr. 1992, 575:153-157), using HPLC analysis. PD and creatinine were quantified by peak integration using the Waters HPLC systems Empower2 software using Allopurinol as internal standard (with known concentration).
A subsample from the thawed urine was taken to measure the nitrogen (N) content using an elemental Leco TruSpec CN analyzer.
Once the concentration of N, PD and creatinine in urine samples was determined the metadata on individual cows was processed as follows:
- Total urine production: creatinine concentration in urine samples is used to estimate total urine volume produced per animal and day. The model used assumes urinary excretion of 29 mg Creatinine/kg BW (body weight) when there is no change in body weight (Valadares et al., J. Dairy Sci. 1999, 82: 2686-2696;
Tebbe and Weiss, J. Dairy Sci. 2018, 6: 5020-5029): Urine volume then is estimated as = BW x 29/creatinine concentration (mg/L). Once the urine volume was estimated, the total excretion of PD and N could be estimated based on the previously determined concentrations. - Nitrogen excretion was calculated in relation to N intake for urine, faeces and milk.
- Microbial N synthesis in the rumen was estimated from the daily excretion of allantoin + uric acid, which reflects the flow and absorption of microbial purine bases (and therefore microbial protein) in each animal, according to procedures provided by IAEA-TECDOC-945 (Estimation of rumen microbial protein production from purine derivatives in urine, published in 1999). Xanthine and hypoxanthine are not considered in cows as most of them are converted to uric acid. The results were expressed as absolute daily excretion and in relation to DM intake, N intake and animals' metabolic weight. In addition to the calculations for urine excretion, the total faeces output was estimated and therefore faecal N excretion. Having the excretion of N in urine and feaces, together with that in milk, allowed us to determine a total N balance assessment and NUE.
Statistical Analysis
The statistical analyses were run using different one-way ANOVA to assess: the effect of lowering protein level: CNP1 vs CLP (group 1 of cows) the effect of adding Crina® under normal protein: CNP3 vs NPC (group 3 of cows) the effect of Crina® under low protein: CLP vs LPC (groups 1 and 2).
When significant effects were detected, means were compared by Fisher's protected least significant difference test using SPSS software (version 21.0, IBM Corp., New York, NY). Significant effects were declared at P < 0.05 and tendency to difference at P < 0.1.
Results
NUE
As indicated in Table 2, the addition of Crina® Ruminants in the low protein diet and in the normal protein diet both increased the nitrogen use efficiency .
* CNP in stage 2, predicted based on lactation curve change in stage 1 and the milk quality based on stage 1 trends with days in milk
Nitrogen excretion Table 3 shows the effect of the different treatments on N excretion in urine, faeces and milk. As it would expected, the reduction in N intake as a result of lowering the protein level in the diet promoted significantly lower N content in urine and as % of the total N intake and therefore the overall N excretion (CNP1 vs CLP). Interestingly, the addition of Crina® Ruminants in low protein treatment significantly decreases faeces N, and increased nitrogen retention, decreased excretion of N in manure (CLP vs LPC). In addition, the addition of Crina® Ruminants to the normal protein diet (NPC) also promoted a significant reduction on both the urinary N content and the N excretion in manure in relation to total N intake.
Table 3. Effects of the different treatments on M excretion in urine, faeces and milk.
* CNP in stage 2, predicted based on lactation curve change in stage 1 and the milk quality based on stage 1 trends with days in milk
Microbial protein synthesis
As shown in Table 4, lowering protein supply substantially reduced microbial protein synthesis (281 vs 242 g/d). However, when Crina® Ruminants was added to the control low protein diet (LPC) the effect was reversed or compensated (242.7 vs 289.3 g/d),
suggesting that the product promotes a more efficient use of dietary N to synthesis microbial biomass in the rumen.
Table 4. Effects of the different treatments on microbial protein synthesis.
CNP in stage 2, predicted based on lactation curve change in stage 1 and the milk quality based on stage 1 trends with days in milk
If the analysis is done looking at the efficiency of microbial protein synthesis (either per kg DMI or N intake), there is no effect of lowering protein content in the diet (10.5 vs 9.84 g N/kg DMI or 0.40 vs 0.41 g N/ g N intake). However, Crina® Ruminants addition improved the efficiency in the low protein diet 9.8 vs 12.2 g N/kg DMI or 0.41 vs 0.49 g N/ g N intake), which confirms the increased ability of the microbial population to metabolize the available N in the rumen. Conclusions
The addition of Crina® Ruminants in the diet of dairy cows substantially improved the nitrogen use efficiency, increased nitrogen retention, decreased nitrogen excretion in manure, and increased microbial protein production.
Especially, when the protein dietary content is lowered, the microbial protein synthesis in the rumen is reduced; however, the addition of Crina® Ruminants reversed that effect by increasing the efficiency of N utilization. Overall, the results show evidence that in a strategy of lowered protein supply in dairy cows, the addition of one or more natural phenolic substances help to maximize the microbial N metabolism in the rumen and can contribute to reduce N excretion to the environment.
Claims
1. Use of one or more natural phenolic substances for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
2. The use of claim 1, wherein the natural phenolic are selected from the group consisting of tannic acid and compounds of formula (I)
formula (I) wherein
R1 is selected from the group consisting of H, Ci-salkyl, Ci-salkoxy and -C(=0)0R4, preferably selected from H, methyl, isopropyl, isoamyl, methoxy,-C(=0)0-benzyl and -C(=0)0-isoamyl;
R2 is selected from the group consisting of H, Ci-salkyl, C2-salkenyl and -C(=0)H, preferably selected from H, methyl, allyl and -C(=0)H;
R3 is selected from the group consisting of H, -OH, Ci-salkyl, C2-salkenyl and Ci-salkoxy, preferably selected from H, -OH, methyl, isopropyl, methoxy, isoamyl and allyl; and
R4 is selected from the group consisting of Ci-salkyl and Ci-salkylphenyl preferably from benzyl, B-methyl-2-butanyl and isoamyl.
3. The use of claim 1 or 2, wherein the natural phenolic substances are selected from the group consisting of 3-hydroxyphenol, 2-methoxyphenol, 3-methylphenol, 2-(l- methylethyl)-5-methyl-phenol, 4-allyl-2-methoxyphenol, 4-hydroxy-3- methoxybenzaldehyde, 5-isopropyl-2-methylphenol, 2-hydroxybenzoates (salicylates) and tannic acid. 4. The use of claim 1 or 2, wherein the one or more natural phenolic substances are a mixture of at least six, preferably all phenolic substances selected from the group consisting of 3-hydroxyphenol, 2-methoxyphenol, 3-methylphenol, 2-(l-methylethyl)-5- methyl-phenol, 4-allyl-2-methoxyphenol,
4-hydroxy-3-methoxybenzaldehyde, tannic acid, benzyl and isoamyl salicylate.
5. The use of claim 1 or 2, wherein the one or more natural phenolic substances is administered in an amount of in the range of from 0.1 to 150 mg/kg body weight per day, preferably 1 to 150 mg/ kg body weight per day, more preferably 50 to 150 mg per kg body weight per day, such as 70 mg to 120 mg per kg body weight per day.
6. The use of claim 1 or 2, wherein the animals are ruminant animals such as sheep, goat, cattle, e.g. cow such as beef cattle and dairy cows, giraffes, American Bison, European
bison, yaks, water buffalo, deer, camels, alpacas, llamas, wildebeest, antelope, pronghorn, and Nilgai.
7. The use of claim 1 or 2, wherein the animals are feed with a low protein diet.
8. A method for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals, comprising administering to the animals one or more natural phenolic substances.
9. The method of claim 8, wherein the one or more natural phenolic substances are a mixture of at least six, preferably all phenolic substances selected from the group consisting of 3-hydroxyphenol, 2-methoxyphenol, 3-methylphenol, 2-(l-methylethyl)-5- methyl-phenol, 4-allyl-2-methoxyphenol, 4-hydroxy-3-methoxybenzaldehyde, tannic acid, benzyl and isoamyl salicylate.
10. A feed composition or animal feed comprising one or more natural phenolic substances for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
11. The feed composition or animal feed of claim 10, wherein the one or more natural phenolic substances are a mixture of at least six, preferably all phenolic substances selected from the group consisting of 3-hydroxyphenol, 2-methoxyphenol, 3- methylphenol, 2-(l-methylethyl)-5-methyl-phenol, 4-allyl-2-methoxyphenol, 4-hydroxy-3- methoxybenzaldehyde, tannic acid, benzyl and isoamyl salicylate.
12. Use of one or more natural phenolic substances in a low protein diet for improving nitrogen use efficiency (NUE), increasing nitrogen retention, decreasing nitrogen excretion in manure, and/or increasing microbial protein production in animals.
13. Use of the one or more natural phenolic substances in a normal protein diet or in a low protein diet for improving nitrogen use efficiency (NUE) in animals.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4211795A (en) * | 1965-02-03 | 1980-07-08 | Institut National de la Recherche Agronomique and Aussedat-Rey | Animal feeds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4211795A (en) * | 1965-02-03 | 1980-07-08 | Institut National de la Recherche Agronomique and Aussedat-Rey | Animal feeds |
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