IL46912A - Method and animal feed compositions containing certain amino-sugar derivatives for improving the quality of the mea - Google Patents

Abstract

1492454 Hexose substituted amino-polyols BAYER AG 20 March 1975 [21 March 1974] 11668/75 Heading C2C [Also in Division A5] Compounds of formula wherein R is a chain of 1-40 hexose units are prepared by aerobic fermentation of a microorganism of the genus Actinoplanes on a nutrient medium including carbohydrates, e.g. starch, glucose or malt extract. The product may be purified on an ion-exchange column followed by chromatography on a polyacrylamide gel column or thin-layer chromatography on silica gel. [GB1492454A]

Description

The present invention relates to the use of amino-sugar derivatives in animal nutrition, for influencing thVv" meat : fat . ratio in favour of the proportion of meat.

It has been found in accordance with the present invention that the amino-sugar derivatives of the formula in which R represents an oligosaccharide chain with 1 to 40 hexose units display the property of preventing undesired formation of fat in animals, and instead favouring increased formation of e meat, because of increased lipoge ^sis and/or lipolysis.

This finding is to be regarded as extremely surprisin since it was not previously known that compounds of the type of the amino-sugar derivatives of the. formula I can influence the meat-fat ratio in animals in favour of an increased proportion of meat. In the production of processed animal products (including fatstock raising) it is of very great economic importance to produce animal^ carcases distinguished by the lowest possible proportion of fat and the highest possible, proportion of lean meat (a high proportion of protein). Furthermore, it is of considerable advantage if the proportion ' of valuable proteins in the animal feed stuff can be reduced without having an adverse influence on the feedin results.

These objectives can be achieved to a high degree with the aid of the compounds of the formula I. Hitherto, no active compounds have been disclosed which, when employed in anima nutrition, make it possible to produce carcases of low pro- ·._'''' portion of fat or to avoid undesired adiposity in animals in as much as this adiposit is undesirable in certain species of animals, for example dogs, and over, certain periods in the life of the animals.

The invention therefore provides a method of improving the leaness of meat comprising administering to a living animal an amino sugar of the formula (I).

The invention also provides a method of treating a noni-human animal in order to reduce the formation offatty tissue in the animal comprising the step of administering to the living animal an aaino sugar of the formula (I).

The compounds of the formula I can be used as active compounds either individually or as mixtures with pne another. The compounds of the formula I can be employed in the pure form, but particularly advantageously in a crude form, such as is obtained from their microbiological production. The crude products do not contain any by-products which have an adverse influence on the desired result and, because of dispensing with a costly fine purification, are substantially more simply obtainable and hence less expensive than the pure active compounds of the formula I.

The oligosaccharide chain R can contain identical or different hexoses which can be in the D-form and/or the L-form , preferably in the D-form. Galactose, mannose and glucose may be mentioned as hexoses which can be present in R,. Preferably, the radical R contains glucose (especially D-glucose) .

The following structural formulae are suggested for the lower members (l and 2 hexose residues) of the compounds of the formula I, there these contain glucose radicals as h Analogous or similar structures can also be assumed for the higher members of the compounds of the formula I.

According to an earlier, as yet unpublished, proposaJ-of this company, the compounds of the formula I which can be used according to the invention can be prepared mlcrobiol-ogically as follows: To prepare the compounds of the formula I which ca be used according to the invention, micro-organisms of he family of the Actinoplanaoeae. belonging to the order Actino-mycetalea. especially strains of the genus Actinoplanes. are employed. Examples which may be mentioned are the strains Actinoplanes species SE 50. (CBS 961.70), SB 18 (CBS 957.70) and SE 82 (CBS 615.71). These micro-organisms have already been described in South African Patent No. 71/8,677 and have been deposited, under the numbers shown in parentheses, in the Centralbureau vor Schimmelcultures in Baarn/Netherlands.

To carry out the preparation process i is furthej strains. The strains SE 50/13 (CBS 614.71) and SE 50/110 (CBS 674.73) prove to be particularly suitable with regard to the total yield of the amino-rsugar derivatives usable according to the invention and/or with regard to the size of the radical R in the mixture of the amino-sugar derivatives formed during the fermentation. The description of both strains corresponds extensively to that of the parent strain SE 50. These strains' have, been obtained without the use of mutagens, by natural ÷ selection from strain SE 50.

To carry out the process', solid and liquid, especially liquid, aqueous nutrient media are used, which in. addition to . carbon sources contain nitrogen sources, salts and anti-foaming agents in the customary concentrations. The concentrations a vary within wide limits.

The carbon sources used are predominantly carbohydrates, especially starch, maltose, glucose and mixtures of two [or three] of the substances, but also complex mixtures such as, for example malt extract, and also polyalcohols such as glycerol and sorbitol.

Nitrogen sources which can be used are the complex mixtures customary in microbiology such as, for example, casein hydrolysate, yeast extract, peptone, fishmeal, fish solubles, corn steep liquor, meat extract and also mixtures, as well as aminoacids and/or ammonium salts.

The process of preparation is in general carried out aerobically in aerated shaken, cultures or in container, cultures, the nature and concentration of the carbon source, in combination with the particular^ strain used for the fermentation, determines the nature of the end product with regard excess of glucose and the duration of fermentation is prolonged, the longer-chain amino-sugar derivatives are also formed. This can be prevented within certain limits if, during the fermentation, the exhaustion of the nitrogen sources coincides in time with the exhaustion of the glucose.

If glucose is entirely dispensed with in the nutrient solutions and maltose is added as the source of carbon, the amino- sugar derivative with 2 hexose units is obtained predominantly. For this purpose, the pure maltose can also be replaced by cheaper mixtures such as, for example, by a natural malt extract. Corresponding to the content of maltotriose, the next higher homologue is then also formed simultaneously. The strain SE 50/110 proves to be particularly N suitable for the preparation of the lower homologues; in r optimum nutrient solutions it gives about twice the yield of lower homologues than that given by the strain SE 5 /13.

In carrying out the fermentations, the composition of the remaining nutrient solution, especially the concentration of the nitrogen sources and the composition of the salt, can vary within wide ranges.

The nutrient media sve sterilised in the usual manner. The pH values of the nutrient solution are between 5.0 and 8.5» preferably between 6.0 and 7.8. The incubation temperatures are between 15 and 45°C» preferably between 24 and 32°C. To prepare higher homologues with the strains SE 0 and SE 50/13, a higher temperature, for example 28°C, is more advantageous, whilst to prepare the lower homologues with the strains SE 50 and SE 50/110 a lower temperature, for example. 24°C, is more favourable. The culture time is ,1-8 days, preferably 2-6 days. Longer culture times, particularly with an excess of carbohydrate, favour the formation of the higher homologues. The end point of the fermentation is determined by determining the composition by thin layer chromatography. Since the compounds of the formula I can also inhibit the enzymes amylase and saccharase, the degree of inhibition is also outstandingly, suitable for use in determ- . ining the end point and altogether for determining the concentrations.

The lower homologues of the amino-sugar derivatives of the formula I can also be obtained by splitting off hexose units from the higher homologues. This is done either with aqueous acids, especially with 1-5-normal mineral acids at temperatures of 50 to 100°C, especially at temperatures of 90 to 100°C, in about 10 to 180 minutes, or by incubation with enzymes (hydrolases), especially with β-amylases or non-inhibitable oc-amylases or amyloglucosidases of microbial origin, such as, for example, a-amylases from Bacterium subtilis, or by incubation with micro-organisms which, as, for example . Aspergillus niger ' (ATCO 11,394) are able to grow in nutrient solutions which contain the higher homologues of the amino-sugar derivatives in amounts of 1 to 10$, preferably 2 to 5 preferably as the sole source of carbon.

The isolation and purification of the amino-sugar derivatives starts either from microbiological culture broths or from acid hydrolysis products or from incubation mixtures in which the enzymatic and/or microbiological conversion or degradation of the higher homologues of the amino-sugar derivatives has been carried out.

Different methods of working up prove suitable depending on the molecular weight range under which the substances to be isolated are to be classified. For example, in the case of the higher homologues isolation is effected by direct precipitation after prior decolourising and concentrating of the solutions.

In contrast, the low molecular homologues are preferably isolated by adsorption, for example on active charcoal at a neutral pH, followed by desorption with aqueous alcohols or acetone, preferably 50-80$ strength acetone.. Desorption-can be carried out particularly completely at acid pH values in the range of pH 1.5 - 4, preferably pH 2 - 3.

If the starting solutions are very dark in colour, they are decolourised, before adsorption, by means of active charcoal at acid pH values (pHl-3) or with any desired nonspecific adsorbent resin in the range of pH 2 - 7, preferably at H 2 - 3. The active charcoal preferentiall binds dye-stuffs in the acid range only whilst the resin does not ad^ . sorb the amino-sugar derivatives in either the neutral or the acid range..

To separate the amino-sugar derivatives from inactive saccharides and other by-products, the weakly basic character of these components is utilised. Under suitable conditions (pH 1-8, preferably pH 2-4; at low ionic strength, corresponding to a conductivity 10 m3, preferably <£_ 2 mS) the homologous amino-sugar derivatives are bonded by strongly acid cation exchangers in the H+ form. The amino-sugar derivatives can be bound to cation exchangers particularly successfully from acetone solution (50 to 80$ of acetone, pH 1 to 5, preferably pH 2 to 4); these exchangers have an appreciably higher capacity for the substances under the said conditions. Provided the solution contains more than 50% of acetone, the amino-sugar derivatives can be bound successfully even to weakly acid exchangers. · Aqueous ammonia solutions are best used for the de-sorption of the amino-sugar derivatives of the formula I from the cation exchangers. The ammonia is stripped from the desprbates ia vacuo and the amino-sugar derivatives are isolated, after concentrating the solution, by lyophilisation or precipitation with organic solvents, preferably with 10-20 volumes of acetone.

In order to prepare the individual members of the homologous series of the amino-sugar derivatives of the., formula I, preferably those in which R contains 1 to 7 hexose units, in the pure form, the pre«purified preparations are chromatographed on a suitable molecular sieve, for example a polyacrylamide resin, and the fractions of the eluate are examined by thin layer chromatography. Fractions which con-tain the amino-sugar derivatives in- a pure form are combined, re-chromatographed and finally lyophilised after concentration or precipitated by means of organic solvents, as described above. In this method, the higher homologues, in which ft contains 7 to 40 hexoses, remain in the excluded volume. Prom this solution, it is possible, if desired, to obtain individual members of the homologues or certain mixtures of these homologous compounds optionally by multiple chromatography.

All amino-sugar derivatives of the formula I share the property that on acid total hydrolysis they give the compounds of. the formula IV [C^E^O^N] , for which the structural formula shown below is proposed,, as well as the corresponding monosaccharide.

As h oncentration and purity of th easily be determined with the. aid of their properties of inhibiting amylase and saccharase. Suitable units of measurement to be employed which may be mentioned are the amylase inhibitor unit, hereafter also referred to as AIU, and the · saccharase inhibitor unit, hereafter also referred to as SIU. The definition and determination of these units can be seen from the following amylase test and saccharase test: ^g inhibitor. + ½jjr- AU ++ + based on solids ++ AU in the non-inhibited batch of the same series and the 50 inhibition point is read off from the curve and converted to AlU/mg of inhibitor. 2. Saccharase test A saccharase inhibitor unit (SIU) is defined as the amount of inhibitor which inhibits two saccharase units to the extent of 0 . A saccharase unit (SU) is the amount of enzyme which in one minute, under the test conditions indicated below, splits 1 umol of sucrose to glucose and fructose. The umol of glucose formed are determined quantitatively, with the aid of the glucose oxidase reaction, under conditions under which a further splitting of sucrose by the sa.ccharase no longer takes place. To carry out the test, 0.05 ml of a saccharase solution^ which has been adjusted to 0.12 SU is mixed with 0-20 ig of inhibitor or 0-20 μΐ of the siution to be tested and made up to 0.1 ml with 0.1 M sodium maleate buffer of pH 6.0. The mixture is equilibrated for 10 minutes at 35°C and 0.1 ml of an 0.05 M sucrose solution in 0.1 M sodium maleate buffer of pH 6.0, prewarmed to 35°C, is then added. The mixture is incubated for 20 minutes at 35°C, the saccharase reaction is stopped by adding 1 ml. of glucose oxidase reagent 2') and incubatipn " is continued for a further 50 minutes at 35°C 1 ml of 50% strength I^SO^ is then added and a reading is take,n at 545 nm against a corresponding blank. For evaluation, the percentage inhibition of the saccharase employed is calculated and converted to SlU/g or SlU/litre from the 50 inhibition point, with the aid of a glucose calibration curve.

' Solubilised saccharase from the mucous membrane of tie small intestine of pigs, accordin to B. Borgstrbm and A.1 Dahlquist, Acta- Chem. Scand. 12, (1958), page 1,997, diluted to an. appropriate SU content with 0.1 M sodium maleate buffer of pH 6.0. 2) The glucose oxidase reagent is prepared by dissolving 2 mg of glucose oxidase (for example from Messrs. Boehringer, No.15, 23) in 100 ml of 0.56 M tris-HCl buffer of pH 7.0 and subsequently adding 1 ml of detergent solution (2 g of a non-ionic surface-active substance produced by reaction of. t ,-octylphenol with ethylene oxide + 8. g of 9 strength very pure ethanol), 1 ml of dianisidine solution (260 m of o-dianisidine.2 HC1 in 20 ml of H20) and 0.5 ml of 0.1 strength aqueous peroxidase solution (for example from Messrs. Boehringer, No.15, 302) .

The compounds of the formula Ϊ which can be used according to the invention have the properties of influencing the ratio of the amount of undesired fat to the amount of desired low-fat meat (lean meat) to a high degree in favour of the lean meat. This is of particular importance in raising and keeping fatstock, for example pigs, but also of considerable importance in raising and keeping other livestock and pets. The use of the compounds of the formula I can furthermore lead to considerable rationalisation in feedin the animals. Since the compounds cause some delay in digestion, the residence time of the nutrients in the digestive tract is lengthened, tfiich in man cases permits ad libitum feeding associated with little expense. Furthermore, the use of the compounds of the formula I in many cases results in a considerable saving of valuable proteins in the feedstuff. ^ The active compounds of the formula I can thus be used in practically all domains of animal nutrition, as agents for reducing the deposition of fat and for savin . feedstuff protein.

The present invention therefore includes a veterinary composition containing as active ingredient a compound of the invention in admixture with a solid or liquefied gaseous diluent, or in admixture with a liquid diluent other than a solvent of a molecular' eight less than 200 (preferably less ·■ than 350) except in the presence of a surface active agent.

The invention also includes a composition in dosage unit form comprising a compound of the invention either alone or in admixture with a diluent. .

The invention also includes a composition in the for of tablets (including lozenges and granules), dragees, capsules and pills comprising a compound of the invention eith alone or in admixture with the diluent.! I "Composition in dosage unit form" as used in this Specification means physically- discrete coherent portions suitable for oral administration each containin a daily dose or a multiple (up to four times) or sub-multiple (down to a fortieth) of a daily dose of the compound of the Le A 15 475 - 14 - invention. Whether the composition contains a daily dose or, for example, a half, a third, or a quarter of a daily dose will depend on whether the composition is to be administered once or, for example, twice, three times or four times a day respectively.

The veterinary compositions according to the . invention may, for example, take the form of gels, pastes, 1 suspensions, solutions and emulsions of the active ingredient in aqueous or non-aqueous diluents, syrups, granules or powders.

The diluents to be used in veterinary compositions (e.g. granulates) adapted to be formed into tablets, dragees, capsules and pills include the following: (a) fillers and extenders, e,g. starch, sugars, mannitol, and silicic acid; (b) binding agents, e.g. carboxymethyl cellulose and other cellulose derivatives, alginates, gelatine and polyvinyl pyrrolidone; (c) moisturizing agents, β·δ· glycerol; (d) disintegrating agents, e.g. agar-agar, calcium carbonate and sodium bicarbonate; (e) surface active agents, e.g. cetyl alcohol, glycerol monostearate; (f) adsorptive carriers, e.g. kaolin and bentonite; (S) lubricants, e.g. talc, calcium and magnesium stearate and solid polyethylene glycols.

The tablets, dragees, capsules and pills formed from the veterinary compositions of the invention can have the customary coatings, envelopes and protective matrices, which may . contain opacifiers. They can be so constituted that they release the active ingredient; only or preferably in a particular part of the intestinal tract, possibly pver a Le A 15 475 - 15 - period of time. The coatings, envelopes and protective matrices may be made, for example, of polymeric substances'or waxes.

The ingredient can also be made up in microencapsulated form together with one or several of the above-mentioned diluents.

The veterinary compositions which are pastes, creams and gels can, for example, contain the usual diluents, e.g. animal and vegetable fats, waxes, paraffins, starch, tragacanth, cellulose, derivatives, polyethylene glycols, silicones, bentonites, silicic acid and talc or i mixtures of these substances.

The veterinary compositions which are powders can, for example, contain the usual diluents, e.g. lactose, talc, silicic, acid aluminium hydroxide, calcium silicate, and polyamide powder or mixtures of these substances.

The veterinary compositions which are solutions and emulsions can, for example, contain the customary diluents (with the above-mebtioned exclusion of solvents having a molecular weight below 200 except in the presence of a surface-active agent), such as solvents, dissolving agents and emulsifiers; specific examples of such diluents are water, ethyl alcohol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1,3-butylene glycol, dimethylformamide, oils [for example ground nut oil], glycerol, tetrahydrofurfuryl alcohol, polyethylene glycols and fatty acid esters of sorbitol or mixtures thereof.

Le A 15· 75 - 16 - The veterinary compositions which are suspensions can contain the. usual diluents, such as liquid diluents, e.g. """ water, ethyl alcohol, propylene glycol, surface-active agents (e.g. ethoxylated isostearyl alcohols, polyoxyethylene sorbite and sorbitane esters), macrocrystalline cellulose, aluminium metahydroxide , bentonite, agar-agar and tragacanth or mixtures thereof.

All the veterinary compositions according to the invention can also contain colouring agents and preservatives as well as perfumes and flavouring additions (e.g. peppermint oil and eucalyptus oil) and sweetening agents (e.g. saccharin) .

The veterinary compositions according to the invention preferably contain about 0.1 to 99.5, more preferably from about 0.5 to 9 $ of the active ingredient by weight of the total composition.

In addition to a compound of the Invention, the veterinary compositions according to the invention may also contain a plurality of compounds of the invention.

The production of the above-mentioned veterinary compositions is carried out by any method known in the art, for example, by mixing the active ingredient(s) with the diluent( s) .

It is envisaged that these active compounds will be administered perorally.

The effectiveness of the active compounds of the formula I is largely independent of the species and gender of the animals. The active compounds of the formula Γ prove particularly valuable in the case of species of animals which have a general tendency for greater deposition of fat, or The following livestock and pets may he mentioned as examples of animals in which the active compounds of thi^" formula I can be employed for reducing the deposition of fat and/or for saving feedstuff protein: warm-bioded animals such as cattle, pigs, horses, sheep, goats, cats, dogs, rabbits, animals raised for fur, for example mink and chincilla, other pets, for example guineapigs and hamsters, laboratory animals and zoo animals,- for example, rats, mice, monkeys and the like, poultry, for example chickens, geese, ducks, turkeys, pigeons, parrots and canaries, and cold-blooded animals, such as fish, for example carp, and reptiles, for example snakes.

The amount of the active compounds administered to the animals to achieve the desired effect can be varied extensively because of the advantageous properties of the active compounds. It is preferably approximately 0.5 mg to 2.5 g and especially 10 to 100 mg/kg of body weight per day. The period of administration can range from a few hours or days up to several years. The suitable amount of active compound and the suitable duration of, administration are clpsely related to the feeding objective. They depend in particular oh the species, the age, the gender, the state of health. and the manner of keeping the animals and are easily determined by anyone skilled in the art.

The active compounds accordin to the invention are administered to the animals in accordance with the customary methods. The nature of the administration depends in particular on the species, behaviour and general cpndltion of the animals. Thus the compounds can be administered orally, once or several times daily* in regular or irregular intervals. For reasons of convenience, an oral administratio: especially in accordance with the rhythm in which the animals take food and/or drink, is to be preferred in. most cases. L The active compounds of the formula I can be administered as pure substances or in a compounded form; the compounded form is to be understood either. as a pre ix, that . is to say a mixture with non-toxic inert excipients of any , desired kind, or as a part of a total ration, in the form of a supplementary feedstuff, or as a mixture component of a singe mixed feedstuff. The administration of suitable preparations in the drinkin water is also included.

The active compounds of the formula I can, i -a compounded form, op-fcionally also be administered together with other active compounds, for example min ral salts, trace elements, vitamins, proteins, energy sources (for example starch, sugar and fats), dyestuffs and/or flavouring substances, in a suitable form. The active compounds of the formula I can be given to the animals before, during or af1;er their consumption cf food. It is advisable to administer them orally together with the feedstuff and/oi* drinking water and in that case, depending on requirements, the active compounds are added to the total amount, or only to parts, pf tjhe feedstuff and/or drinking water.

The active compounds of the formula I can be added to the feedstuff and/or the drinking water by customary. methods, by simple mixing, as pure compounds,, preferably in a finely divided form, or in a ccmppunded form, as a mixture with edible non-toxic expipients, and optionally also in the form of a premix or of a feedstuff concentrate.

. B way of example, the feedstuff and/or the drinking water can contain the active compounds according to the invention in a concentration of about 0.001 to 5.0 , especially0.02 to 2.0% (by weight). The optimum level of concentration of the active compound in the feedstuff ahd/^r drinking water depends, in particular, on the amount of feedstuff and/or drinking water taken by the animals and can' easily be determined by anyone skilled in the art.

The nature of the feedstuff and its composition is immaterial to the above remarks. All customary, commercially available or special feedstuff compositions can be used, which preferably contain the customary balance of energy sources and proteins, also including vitamins and mineral substances, required for balanced nutrition. The feedstuff can be composed, for example, of vegetable substances, for. example shredded oilcakes, shredded cereals and cereal by-products, but -Lso of hay, silage, beet and other forage plants, of animal matter, for example meat products and fish products, bonemeal, fats, vitamins, for example A, D, E, K and B' complex as well as special sources of protein, for example yeasts · and certain aminoacids and mineral substances and trace' elements such as, for example, phosphorus and iron, zinc, manganese, copper, cobalt, iodine and the like.

Premixes can preferably contain about 0.1 to 50$, especially 0.5 to 5.0$ (by weight) of the active compounds of the formula I in addition to an desired edible, excipients and/or mineral salts, for example carbonated feedgtuff lime, and are produced by the customary mixing methods.

Mixed feedstuffs preferably contain 0.001 to 5.0 , especially 0.02 to 2.0 (by weight) of the active compounds of the formula I in addition to the customary raw material components of a mixed feedstuff, for example shredded cereals or cereal by-products, shredded oilcakes, animal protein, minerals, trace elements and vitamins. They can.be produced by the customary mixing methods.

Preferably in premixes and mixed feedstuffs, the active compounds can optionally also be protected against air, light and/or moisture by suitable agents which cover . the surface of the active compounds, for example by non-toxic waxes or gelatine.

The following Examples illustrate animal feedstuffs in accordance with this invention.

Example I An example of the composition of a ready-mixed feed- . stuff for poultry, which contains an active compound of the formula I: 200 g of wheat, 340 g of maize, 360.3 g of shredded soya, 60 g of beef tallow, 15 g of dicalcium phosphate, 10 g ofcalcium carbonate, 4 g of iodised sodium chloride, 7.5 g of vitamin-mineral mixture and 3.2 g of active compound premix after careful mixing give 1 kg of feedstuff.

The vitamin-mineral mixture consists of: 6,000 I.U of vitamin A, 1,000 I.U of vitamin D^, 10 m of vitamin E, 1 mg of vitamin K^, 3 mg of riboflavin, 2 mg of pyridoxin, 20 meg of vitamin B12, 5 mg of calcium pantothenate, 30 mg of nicotinic acid, 200 mg of choline chloride, 200 mg of MnSO^ x H20, 140 mg of ZnS04 x 7H20, 100 mg of PeS04 x 7H20 and 20 m of CuSO^ x 5H20.

The active compound premix contains the active compound of the firmula I in the desired amount, for example 1,600 mg corresponding to 5 x 10^ AIU and additionally 1 g of DL-methionine and sufficient soya bean flour to give 3.2 g of premix.

Example II .

An example of the composition of a mixed feedstuff for pigs, which contains an active compound of the formula I: 630 g of shredded feedstuff cereal (compose*} of 200^ of shredded maize, 150 g of shredded barley, 150 g of shredded oats and 130 g of shredded wheat) , 80 g of fishmeal, 60 g of shredded soya, 58.8 g of tapioca meal, 38 g of brewer's yeast, 50 g of vitamin-mineral mixture for pigs (composition, for example, as for the chick feedstuff), 30 g of linseed oil cake meal, 30 g of maize gluten feedstuff, 10 g of soya oil, 10 g of sugar cane molasses and 2 g of active compound pre-mix (composition, for example, as for the chick feedstuff) after careful mixing give 1 kg of feedstuff.

The above feedstuff mixtures are preferentially intended for raising and fattening chicks and pigs respects ively but can also be used, in an identical or similar composition, for raising and fattening other animals.

As already mentioned, the active compounds of the formula I can be used individually or in any desired mixtures with one another, and both the pure active compounds and the crude active compounds obtained from their process of preparation, optionally after a coarse purification, are employed. Examples of mixtures which can be used are mixtures of compounds of the formula I which contain, for example, about 7 to 40, preferably 7 to 25, and especially 7 to 20, hexoses in the radical R. However, it is also possible to use compounds, individually or as mixtures with one another, which contain 1 to 7, preferably 1 to 3, hexoses in the radical R. Mixtures of the lower and the higher homol-ogues can also be employed. In the case of feedstuff preparations (for example sugar beets) of particularly high dextrin content, it can be advisable to use compounds of the formula I in which R consists of a small number, for example 1 to 7, preferably 1 to 3, hexose residues, or to use mixtures of compounds of the formula I which- contain a major proportion of the low homologues. In the case of feedstuff preparations of particularly high starch content it can "be advisable to use compounds of the formula I in which R consists of a higher number, for example 5 to 35, preferably 7 to 20, hexose residues, or. to use mixtures which contain a major proportion of higher homologues. The composition of active compound mixtures can be varied very extensively and is not to be regarded as critical^ The activity of the compounds of the formula I which can be used according to the invention can be demonstrated by the following animal experiments: Experiment a) The influence of active compounds from Examples 1 and 4 on the development of depot fats in rats.

In Experiment a.^, rats fed at set times were supplied with the active compound from Example' 1 together with the feedstuff for 27 days. The epididymal and retroperitoneal (perirenal) fatty tissue weighed after this time showed that the active compound produces a decrease in, or reduced formation of, the epididymal and retroperitoneal fatty tissue, the effect bein 15-40 per cent, depending on the dose (compare Table l). The faecal excretion of starch was the same for all groups.

In Experiment a2, conventionally fed rats were supplied with the active compound from Example 4 together with the feedstuff for 28 days. The parametrial fatty tissue, weighed after this time, showed that the active compound produces a decrease in, or reduced formation of, the parametrial fatty tissue, the effect being 10-48 per cent, depending on the dose (compare Table 2). Φ Table 1 Η Fatty tissue weights in mg i Is ¾^ of rat, per 100 g of Tissue Groups of experiments -J 1 I II Retroperitoneal fat/rat 662 - 86 484 - 2 Retroperitoneal fat/100 g of rat . 361 (= 100$) 271 (= Epididymal fat/rat 1473 - 344. 1213_Jj_ Epididymal fat/100 g of rat 805 (= 100$) 685 (= 8 Group IV = 0.500 M " Each group contained 12 animals Tables 1 and 2 show clearly that the animals which ^ received active compound from Examples 1 and 4 deposit sub-^ stantially less fat than the control animals which did not receive an active compound.

Material and methods for Experiments a-j^ and a^) Animal material in Experiment a-^: male Wistar rats/Winkelmann, SPF, 150-200 g Animal material in Experiment a2: female Wistar rats/Hagemann, SPF, 190-215' g Feedstuff in Experiment --'a^ and a2: full ration feedstuff with 50% of starch, tap water ad libitum Animal accommodation in Experiment and a2: 6 rats/cage with wire bottoms and faeces tray Feeding times in Experiment a-^: 800 to 8^° and 1600 to 16^ Before the beginning of the experiment, the animals were rendered accustomed to this mode of feeding over 4 weeks.

Feeding times in Experiment a2: ad libitum Weighing the organs in Experiment a1 and a2: after bleeding the rats from the orbital vein plexus, stunning them by a blow on the head and cutting their throat, the epididymal, retroperitoneal arid para- metrial fatty tissue was prepared and weighed (accuracy: + 0.2 mg).

Experiment b) Reducing the deposition of fat and improving the deposition of protein by the use of the active compounds, usable according to the invention, as a feedstuff additive in pig feeding In the course of fattening pigs, fed at set times, from approx. 60 to 150 kg live weight (requiring approx. 20 weeks), 5.0 mega-AIU of the active compound from Example 1/kg . of feedstuff (= ex erimental rou ) or no active com ound (= control) were administered. After reaching a unifori^ final slaughtering weight of approx. 150 kg, all animals were killed and a series of data determined for assessing the quality of the carcases.

After covariance-analytical correction of initial weight and final weight, and duration of the study, the following differences in the butchery criteria of the two groups were found : Table 2 Points of measurement with active without active compound compound Formation of fat Thickness of fat, withers, in cm 5.43 - 0.14 6.71 - 0.12 Thickness of fat, centre of back, in cm 3.52 ± 0.08 4.15 - 0.06 Thickness of fat, loin, in cm 4.71 - 0.11 5.11 i 0.09 Ham, fat layer in kg 5.03 - 0.10 5.49 - 0.09 Formation of meat Chop: fat-free centre portion of meat, in cm2 50.4 - 1.01 45.4 - 0.84 The slaughtering results have shown that as a result of the use of the active compounds usable according to the invention, the deposition of fat is reduced and the formation of meat (lean meat) is improved, for example by an increase in the proportion of meat over the area of the chop.

Material and methods of experiment b) Animal material;.

From 5 litters, of equal age, of the white Belgian breed, 4 animals of equal strength (2 castrated males (= castrated boars) and 2 females) were selected in each case, and were in each case divided, in pairs, between the two. experi.ental groups. * Accommodation: Individual sties: Feedstuff: Commercially available pig fattening feedstuff with all nutrients and active compounds for optimum growth (in this context, see the mixed feedstuff recipe for pigs given earlier). Where the animals received the active compound, the latter was given as a mixture with the feedstuff.

Feeding: The feeding was carried out in accordance with the Rationstabelle der Deutschen Landwirtschafts-Gesellschaft (DLG) (Rations Table of the German Agricultural Association) , that is to say the increase in the daily allocation of feedstuff was matched to the particular weight development of the average of the group. The feeding times were 8.00 a.m. and 8.00 p.m.

Experimental procedure: a) Feeding experiment: The experiment starts with approximately 60 kg live weight. Feeding corresponding to the weekly progress in weight. Weighing once weekly, always on the same day of the week, in the morning, before feeding. 3 animals (2 male, 1 female) of the experimental group were removed from the experiment in the 6th, 7th and 13th week, and 1 animal (female) of the control group was removed from the experiment, also in the 7t week of the experiment, in each case because of refusal of. food. Dissection showed chronic pneumonia or a pneumonic infection. Taking the animals out of the experiment was therefore in no way related to their being fed the active compound. ^ b) Slaughtering experiment: On reaching the predetermined final. slaughtering weight of approximately 150 kg, all animals were killed by . electrocution. The animals were gutted and both sides were weighted warm and then placed in a cold store for 24 hours. When they were cold, the sides were again weighed and the measurements summarised in the results were carried out.

The measurements of the thickness of fat at the accurately defined points of measurement were carried out by means of a slide. caliper and the layer of fat on the ham was carefully cut off and weighed. The area of meat of the chops was determined for all the animals in accordance with a standard method for assessing carcases, developed for this purpose,' by cutting a chop between the 13th and 14th rib. The chop surface was photographed to scale and the proportions of fat surface and meat surface were measured with a planimeter.

Evaluation: ¾ The covariance-analytical correction of all the individual results was made with regard to the initial and final weight of the animals and the duration of the study.

The preparation of the active compounds of the formula I usable according to the invention can be illustrated by the following examples: .

Example 1 A preparation which is produced as. follows is used as a starting material in some of the examples which follow: A glass fermenter containing 8 litres of nutrient solution comprising 5.0$ of starch, 1.0$ of yeast extract and 0.2$ of 2HP04 is inoculated with a 3 day old shaken flask culture of the strain SE 50/13 (CBS 614.71), the mixture is incubated for 3 days at 28°C with intensive stirring and aeration, and a culture broth containing 105,000 AlU/ml is obtained.

After cooling to 20°C, 6 litres of this fermentation broth are adjusted to pH 2.5 with half-concentrated HNO^, 30 g of active charcoal are added and the mixture is stirred for 10 minutes. It is then centrifuged for 15 minutes at 10,000 rpm and the clear, light yellow supernatant liquor is neutralised with NH^ and then concentrated to 500 ml. The 500 ml of concentrate were stirred for 45 minutes with 200 g of an anion exchanger (Cl~), filtered off, and 4/5 volume = 400 ml of methanol were added to precipitate the bulk of the high molecular starch degradation products. The mixture is centrifuged for 5 minutes at 5,000 rpm. The 850 ml of supernatant liquor are added dropwise to 4 litres of ethanol, with intensive stirring. The white flocculent precipitate is filtered off, washed 3 times with ethanol and twice with ether and dried in vacuo at 50°C. Yield: 36 g of a white powder containing 10 x 10^ AlU/g. The product thus obtained corresponds to the formula I, wherein R contains 7 to 40 hexose residues. The distribution of homologues can vary depending on how the experiment is carried out. In many cases, a product is obtained which contains about 30 of constituents in which the radical R consists of 20 to 40 hexoses, and which contains about 70 of constituents in which the radical R contains 7 to 20 hexose residues (the % constituents is to be understood as proportion by weight).

Example 2 If 1 litre Erlenmeyer flasks containing 120 ml of a nutrient solution, consisting of 4% of starch, 2.4 of glucose, 0.9 of casein hydrolysate and 0.9% of yeast ex- tract, pH adjusted to 7.6 with NaOH, 0.4% of CaCO^ having been added and the nutrient solution having been sterilised for 30. minutes at 121°C, are inoculated with 3 ml of a pre-culture of the strain SE 82, grown in a nutrient solution consisting of 2$ of starch, 1% of glucose, 0.5% of casein hydrolysate and 1% of yeast extract, pH adjusted to 7.2 with NaOH, 0.4 of CaCO^ having been added and the nutrient solution having been sterilised for 30 minutes at 12l°C, and if the inoculated mixture is incubated for 5 days at 28°C on a rotary shaking machine, a culture solution containing 122,000 AlU/ml is obtained. For working up, the mycelium is separated from the combined culture solutions by centrifuging at 12,000 rpm, 300 ml of the culture filtrate are adjusted to pH 2.5 with half-coneentrated HNO^, and the mixture is stirred for 10 minutes with 2.5 g of active charcoal. After separating off the charcoal at 12,000 rpm, 300 ml of methanol are added to the solution which has been neutralised to pH 6 with 10 N KOH, and the mixture is left to stand briefly and is freed from the precipitate at 12,000 rpm. If now the supernatant liquor is dripped into 3 litres of ethanol and the precipitate is isolated, after brief standing, by centrifuging at 12,000 rpm and is washed twice with absolute ehtanol and once with ether and dried in vacuo, 2.23 g of a product containing 7.45 x 10^ AlU/g are obtained; this product contains more than 95 of higher homologues of the amino-sugar derivatives, in which R in the formula I consists, of 4 to 40 hexose residues. Example 3 If a 1 litre Erlenmeyer flask containing 120 ml of nutrient solution comprising 3% of glucose, 0.6 of casein hydrolysate, 1.6% of yeast extract, 0.3% of CaCO^, 0.3% of KgHPO^, pH before sterilisation adjusted to 7.8 with KOH, sterilisation for 30'/l21oC,- is inoculated with 6 ml of a pre-culture of the strain SE 50/110 in a nutrient solution consisting of y/o of soya flour, 3% of glycerol and 0.2$ of CaCO^, and the mixture is incubated for 3 to 4 days on a rotary shaking machine at 24°C, a culture broth with 10,800 SlU/litre is obtained, which predominantly contains the amino-susjar derivative of the formula I, in which R represents a hexose residue. 5 litres of culture filtrate, separated from the mycelium at 13,000 rpm, are adjusted to pH 2.5 with half-concentrated H O-j and stirred for 15 minutes with 5 g of active charcoal and 200 g of a filtration auxiliary. After removing the solids by filtration, the mixture is neutralised to pH 7 with concentrated ammonia and the solution is concentrated to 1.5 litres and precipitated with a 5-fold quantity of ethanol. The resulting flocculent precipitate is separated off by means of a continuous flow rotor at 12,000 rpm and the yellowish supernatant liquor is concentrated to 150 ml and centrifuged at low speed to separate off small proportions of undissolved material. 50 ml of this solution are charged onto a column (30 x 300 mm; 30 ml of R^O per hour) filled with a strongly acid ion exchanger (H+ form). After a total of 300 ml of eluate, which contains inert saccharides and a proportion of non-adsorbed active compounds according to the invention, have been collected, the exchanger is transferred into a beaker by means of approximately 400 ml of ^O and concentrated ammonia is added, whilst stirring, until the pH reaches a value of 11. . After stirring for a further 30 minutes, the exchanger is separated off and the solution is concentrated to l/20 of its volume and filtered through a column (20 x 150 mm) containing an anion exchanger (HCO-.' form), and approximately 500 ml of eluate are collec^gd at a flow speed of 30 ml/hour; the eluate is concentrated and after lyophilisation gives 1.3 g of crude product.

A further purification of the crude product can be carried out as follows: For further purification, the crude preparation is fractionated on a polyacrylamide gel of 100-200 mesh. This is done using, for example, a column of 50 mm t> and 450 mm length, which is operated with R^O at a flow speed of 40 ml/ hour, collecting fractions of 10 m^L each. All fractions are tested for carbohydrates by means of the anthrone test and for active components by means of the saccharase inhibition test. The fractions containing active compounds according to the invention are furthermore examined by thin layer chromatography for their content of individual components.

Those fractions which contain the amino-sugar derivative of the formula I with R = a hexose residue are combined* concentrated and lyophilised. 35 mg of the amino-sugar derivative with R = 1 hexose residue and with 0.3 x 10 AlU/g and 30,000 SlU/g are obtained.

Example 4 If a fermenter containing 100 L of nutrient solution comprising 3.5 of glucose, 2.5% of malt extract, 0.5% of casein hydrolysat'e , 1.3% of yeast extract, 0.3% of CaCO^, 0.3% of K^PO^ and 0.1% of anti-foaming agent is inoculated with 5 1 of a pre-culture according to Example 3 and incubated for 5 days at 24°C whilst stirring and aerating, a culture solution with 73,000 SIU/L is obtained,which predominantly contains the amino-sugar derivative of the formula I, in which R denotes 2 hexose residues. 90 litres of fermentation batch, together with mycelium, were adjusted to pH 2.5 with concentrated HNO^, using a pH meter, and 900 g (= io) of active charcoal were added, whilst stirring, to adsorb the bulk of the dyestuffs formed. The mixture is stirred for 15 minutes, the mycelium and the bulk of the carbon are separated off on a centrifuge at 3,000 rpm, and the supernatant liquid is finally filtered through a pressure filter, 3 kg of a filtration auxiliary being added. 65 litres of yellow-brown clear filtrate containing 60,000 SlU/litre are obtained.

The filtrate is adjusted to pH 7 with concentrated NH^ and stirred with 1,300 g (2$) of. active charcoal for 30 minutes to adsorb the active compound. The mixture is filtered through a pressure filter and the active charcoal sediment is washed three times with 10 litres of distilled water. The charcoal is then pressed out thoroughly until dry and is stirred in 3 x 4 litres of 50 (per cent by volume) of acetone at pH 2.5» in each case for 15 minutes, in order to desorb the active compounds from the charcoal. The acetone desorbates are combined after separation from the charcoal by filtration. The combined desorbate is concentrated to 250 ml on a rotary evaporator, ah equal volume (25Ο ml) of methanol is added and the mixture is filtered through a folded filter. The filtrate (480 ml) is added dropwise to 5 litres of acetone, with vigorous stirring. The precipitate which separates out is filtered off and washed three times with acetone and ether. It is then dried in vacuo at 35°C. Yield: 230 g containing 8,500 SlU/g. 25 g of the above crude product are dissolved in 1 litre of H20 and stirred for 30 minutes with 300 g of a strongly acid cation exchanger. The resin is filtered off and rinsed three times with 2 litres of 0.001 N HC1. The washed resin is then suspended in 500 ml of I^O and the ^ suspension is. adjusted to pH 9.0, using a pH meter, by addition of 25$ NH^. Thereafter a further two desorptions are carried out, in each case With 500 ml of 0.6$ NH.-.,. and the desorbates are combined and concentrated to 100 ml on a rotary evaporator. To decolourise this concentrate, it is stirred for 5 minutes with 2 g of a cellulose-based anion exchanger ( 0.6 milliequivalent/g) for 5 minutes and then centrifuged. The light yellow supernatant liquid is mixed with an equal volume (100 ml of methanol) and then added dropwise to 2 litres of acetone, with intensive stirring.

The precipitate is filtered off, washed with acetone and ether and dried _in vacuo at 35°C. Yield: 4.2 g containing 26,000 SIU/g.

For further fine purification, the 4.0 g of inhibitor, in 0.5 g portions, are gel-iLltered over a polyacrylamide gel. For this purpose, 0.5 g of the preparation is dissolved in 10 ml of H20 and applied to a gel-filled column (200-400 mesh) of diameter 5 cm and length 95 cm. The column is developed in water at a flow rate of 80 ml/hour. 12 ml fractions are collected. The otal carbohydrate content (in the fprm of the anthrone test, as the extinction at Eg2Q) and the content of saccharase inhibitor and amylase inhibitor is determined for all fractions. In addition, the fractions are examined by thin layer chromatography.

The fractions in which the amino-sugar derivatives of the formula I with R = 4 to 6 hexose residues are detected are combined, concentrated in vacuo to 10 ml and precipitated by dropwise addition to 200 ml of ethanol. The precipitate is centrifuged off, washed with acetone and ether and dried in vacuo; yield from 4.0 g of crude inhibitor: 0.2 g of amino-sugar derivative (R = 4 to 6 hexose residues) with 17.5 x 10 AlU/g and 8,500 SlU/g. The fractions containing the amino-sugar derivative with R = 3 hexose residues are worked up' in the same manner, the precipitation being carried out with 200 ml of acetone; yield from 4.0 g crude inhibitor: 0.1 g of amino-sugar derivative with R = 3 hexose residues with 1.4 x 106 AlU/g and 21,000 SlU/g. 0.9 g of amino-sugar derivative with R = 2 hexose residues, and with 0.3 x 10^ AlU/g and 68,000 SlU/g is isolated from the fractions containing the amino-sugar derivative with R = 2 hexose residues (precipitation with acetone).

Example 5 To obtain the amino-sugar derivatives of the formula I in which R represents 5 to 7 hexose residues, the starting material is, for example, a preparation as described in Example 1. ^or this purpose, 30 g of the preparation according to Example 1 are dissolved in 250 ml of H20. The conductivity of this solution is 10 mS and the pH is 5.5. To desalinate the solution, it is mixed with 60 g of a weakly acid cation exchanger, which only binds traces of the amino- sugar derivatives from aqueous solution, and 20 g of a strongly basic ion exchanger, and the mixture is stirred for 20 minutes. The filtrate (conductivity 0.5 mS, pH 3.5) is adjusted to pH 3.0 with 1 N HC1 (conductivity 0.6 mS). This solution is pumped at 42 ml/hour through a column filled with a strongly acid ion exchanger (diameter 2.5 cm, height 40 cm, equilibrated in 0.001 N HGl) and the colutan is then rinsed with 2 litres of 0.001 N HC1. After washing the column, elution is carried out with 1.2$ aqueous ammonia and 10 ml fractions are collected. The fractions which are active according to the amylase and saccharase tests are combined, the ammonia is stripped off in vacuo and the solution is tken concentrated to 30 ml in vacuo. Precipitation is carried out by dropwise addition of the concentrate to 600 ml of ethanol and the precipitate is filtered off, washed with ethanol and ether, and dried in vacuo . Yield: 4.4 g containing 26.5 x 106 AlU/g. 0.5 g portions are subjected to a fine purification by applying them to a preparative column filled wi†h a polyr acrylamide gel, as described in Example 4, and developing the column. The fractions which contain amino-sugar derivatives of the formula I with R = 5 to 7 hexose residues, as determined by a thin layer chromatogram, are combined, concentrated in vacuo and precipitated' with ethanol as described above. Yield from 0.5 g of crude product: 0.2 g of amino-sugar derivatives of the formula I, wherein R represents 5 to 7 hexose residues, with 30 x 106 AlU/g and 2,500 SlU/g. The individual homologous amino-sugar derivatives with R = 5, 6 and 7 hexose residues can be obtained by several-fold rechromatography.

In the above exaiiples, # denotes per cent by weight, unless stated otherwise.

Notes on some reagents and auxiliaries used: As ion exchangers it is possible to use, for example, the commercially available products Amberlite IRA 410 Cl~ (anion exchanger); Amberlite IRC 120 (H+ form) (strongly acid cation exchanger); Amberlite (HCO-j1 form) (anion exchanger); Amberlite IRA 410 0H~ (strongly basic anion exchanger); Amberlite IRC 50 H+ (weakly acid cation exchanger) [tradenames of Messrs. Rohm and Haas Company ] and Dowex 50 WX 4H+ (strongly acid cation exchanger) [tradename of Messrs. Dow Chemical Co. Midland, Michigan, USA] .

As a cellulose-based anion exchanger it is ossible to use, for example DE AE-cellulose of Messrs. Schleicher nnd SehVU.

As a pol yacrylamide p;el i t is possible to use, for example, Biqgel-P-2 (tradename of Messrs. Bio Rad Laboratories, Richmond, California, USA).

The abovementioned strains were deposited as follows SE 50: CBS 961.70 ATCC 31 , 042 FRI 1,266 SB 18: CBS 957.70 ATCC 31,041 FRI 1,257 SE 82: CBS 615.71 ATCC 31,045 FRI 1,268 SE 50/13: CBS 614.71 ATCC 31,043 FRI 1,976 SE 50 /110: CBS 674.73 ATCC 31,044 FRI 2,610 Aspergillus niger ATCC 11,394 is readily available and is described in: "ATCC Catalogue of Strains", 8th edition, 1968, on page 77.

CBS = Centraalbureau voor Schimmelkultures, Netherlands ATCC = American Type Culture Collection, U.S.A.

FRI Fermentation Research Institute, Tokyo, Japan.

In the text which follows there is given, by way of example, a closer characterisation, by physico-chemical data, of the lower homologous amino-sugar derivatives of the formula I, in which R represents 1 to 7 glucose residues: 1. R = 1 glucose residue (hereafter referred to as "A").

The compound is a colourless, amorphous solid of . good solubility in H20, DMF, DMSO and MeOH. It is also soluble in hot ethanol. a) Thin layer chromatography: Flow medium: ethyl acetate/methanol/H20, 10:6 :4 (parts by , volume) I. Thin layer chromatography on silica gel (thin layer chromatography ready-to-use F 1500 silica gel sheets from Messrs. Scheicher and Schuil) Rf values A: 0.46 maltose: 0.50 glucose: 0.65 II. Thin layer chromatography on silica gel (thin layer chrom atography ready-to-use F 254 silica gel plates from Messrs. Merck) Rf values A: 0.47 maltose: 0.54 glucose: 0.66 b) Optical rotation: A non-crystalline sample of A, obtained by concentrating a solution of A in methanol, was dissolved in water and the specific rotation was found to be [a]D =.+134.3 c) IR spectrum: Provides little information, poor structure IR spectrum in Br. Main absorption bands in the region of the O-H and C-0 valency vibrations. d) MMR spectrum in QD^OD at 220 Mc/s: .$ in ppm Multiplicity relative ' intensity Doublet: J=6.5 c/s 3 H "Triplet"; J± and J≥ 8-10 1 H 3.15 "Triplet"; J1 and J≥ 7-9 c 1H 3.3-3.9 Signals cannot be assigned individually 12 H 4.13 AB system; J = 12 c/s 2 H 4.48) Doublet; J■ = 7 c/s ) and 5.1 ) Doublet; J = 2.5 c/s ) 1 H Singlet 11 H protons replaced by deuterium Le A 15 475 - 40 - Sin ppm Multiplicity relative * ■ ■ ; intensity 5.0 Doublet; J = 2-3 c/s (poor resolution) 1 H 5.8 , Doublet; J = 3-4 c/s (poor resolution 1 H 33 H To render the amino-sugar derivative visible on silica gel plates it is best to use the. AgNO^/NaOH spray re-agent. A brown-black colouration is obtained even at room temperature or after slight . arming. 2. R = 2 glucose residues (hereafter referred to as "B") B is a readily water-soluble amorphous solid product.. a) Thin layer chromatography; Plow medium: ethyl acetate/methanol/H^O 10:6:4 (parts by volume) I. Thin layer chromatography on silica gel (thin layer chromatography ready-to-use P 1500 silica gel sheets (Schleicher + Schull): Rf values B: 0.35 maltose : 0.50 II. Thin, layer chromatography on silica gel (thin layer chromatography ready-to-use F 254 silica gel plates (Merck): Rf values B; 0.33 maltose: 0.54 B gives a brown-black colouration with the AgNO^/NaOH spray reagent even at room temperature or on slight warming of the plates. b) IR spectrum: Provides little information, IR spectrum of poor resolution in Br. Main absorption bands in the region of the 0-H and C-0 valency vibrations ( ,700-3 , 100 cm-1 and 1,180-950 cm respectively)., c) ·· Optical rotation: ■ [a]D in H20:. + .147.2° 3. R = 3 glucose residues (hereafter referred to as "0") . The compound C can be split, on acid partial hydrolysis, into the compound A and glucose in the molar ratio 1:2.

Thin layer chromatography : Flow medium: n-butanol/ethanol/water = 50:30:20 (narts by ' volume) ■ Thin layer chromatography on silica gel (F.1500 · silica gel ready-to-use thin layer chromatography plates (Schfeicher + Schull): glucose values C: 0.41 - 0.46 4. , R = 4. 5. 6 and 7 glucose residues (hereafter referred to as "D" . "E" . "F" and "G" ) Thin layer chromatography: Flow medium': n-butanol/ethanol/water = 50:30:20 (parts by volume) Thin layer chromatography on silica gel (F 1500 silica gel ready-to-use thin' layer chromatography- plates (Schleicher + Schull): Hgl-,'„ucose values D: 0.30 - 0.34 E : 0.21- - 0.23 F: 0.14 - 0.16 G: • 0.09 - 0.11 e A 15 475 - 2 -

Claims (27)

What we claim is:

1. .1. A method of improving the leaness of meat comprising administering to a living .animal an amino-sugar of the formula (I) wherei . R represents an oligosaccharide chain with from 1 to 40 hexose residues.

2. A method of treating a non-human animal in order to reduce the formation of fatty tissue in the animal comprising the step of administering to the living animal an amino-sugar of the formula (I).

3. method according to claim 1 or claim 2 wherein R is an. oligosaccharide chain containing hexose units in the D-form.

4. A method according to any one of claims 1 to 3 wherein R is an oligosaccharide chain containing glucose units.

5. A method according to claim 4 wherein the glucose units are D-glucose units.

6. A method according to any one of claims 1 - 5 wherein R is an oligosaccharide chain offrom 1 to 7 hexose units.

7. A method according to claim 1 wherein the amino-sugar is substantially as described in any one of Examples 1 to 5.

8. A method according to claim 7 wherein the amino-sugar is any one of the amino-sugars specifically mentioned herein.

9. A method according to any one of claims 1 to 8 wh^e_r.e in the living animal is an agricultural livestock animal.

10. A method according to claim 9 wherein the livin animal is a pig.

11. A method according to any one of claims 1 to 12 . wherein the amino-sugar is administered in an amount of-from 0.5 rag to 2.5 g per kg of body weight per day.

12. · A method according to any one of claims 1 to 10 wherein' the amino-sugar is administered orally.

13. · A method according to claim 11 wherein the amino-sugar is administered in an animal feedstuff.

14. Meat whenever produced by a method according to claim 1 or any one of claims 3 to 13 when dependent upon claim 1.

15. An animal feedstuff comprising one or more am os sugars as defined in any one of claims 1 to 8 and a nutri Λtous material.

16. An animal feedstuff according to claim 15 wherei the nutritous material is of high dextrin content and the amino-sugar .or sugars are of the formula (I) in which R represents an oligosaccharide chain containing from 1 to 7 dextrose units.

17. An animal feedstuff according to claim 15 wherein the nutrit Ao.us material is of high starch content and the amino sugar or sugars are of the formula (I) in which R represents an oligosaccharide chain containing from 5 to 35 hexose units.

18. An animal feedstuff according to an one of claims 15 to 17 containing from 0.001 to 0$ by weight . of the amino-r sugar or amino-sugars.

19. An animal feedstuff according to any.one of claims « 15 or claim 18. in the form of an animal feed premix. k

20. An animal feedstuff substantially as hereinbefore described in Example I or Example II.

21. A method according to claim 13 wherein the animal feedstuff is in accordance with any one of claims 16 to 20.

22. A veterinary composition containing as an active ingredient an amino-sugar as defined in any one of claims 1 to 8 in admixture with a solid or liquefied gaseous diluent or in admixture with a liquid diluent other than a solvent of a molecular weight less..than 200 except in the presence of a surface-active agent.

23. A veterinary composition containing as an active ingredient a compound as defined in any one of claims 1 to 8 in the form of a sterile or isotonic aqueous solution.

24. A composition according to claim 22 or claim 23 containing from 0.5 to 95?° of the said active ingredient, b weight.

25. A composition in dosage unit form comprising a compound as defined in any of claims 1 to 8 either alone or in admixture with a diluent.

26. A composition in the form of tablets, pills, dragees and capsules, comprising a compound as defined in any of claims 1 to.8 either alone or in admixture with a diluent.

27. A method according to any one of claims 1 to 10 and 13 wherein the amino-sugar is administered either alone or in admixture with a diluent or in the form of a composition according to claim 24 or claim 25. '