WO2001079241A1 - Esters de glycoside, leur preparation et leur utilisation comme agents cosmetiques, pharmaceutiques et comme produits alimentaires et substances fourrageres - Google Patents

Esters de glycoside, leur preparation et leur utilisation comme agents cosmetiques, pharmaceutiques et comme produits alimentaires et substances fourrageres Download PDF

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Publication number
WO2001079241A1
WO2001079241A1 PCT/EP2001/004153 EP0104153W WO0179241A1 WO 2001079241 A1 WO2001079241 A1 WO 2001079241A1 EP 0104153 W EP0104153 W EP 0104153W WO 0179241 A1 WO0179241 A1 WO 0179241A1
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compounds
eis
sugar
group
radical
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PCT/EP2001/004153
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German (de)
English (en)
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Albrecht Weiss
Ralf Otto
Bernadette Geers
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Henkel Kommanditgesellschaft Auf Aktien
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Priority to AU73939/01A priority Critical patent/AU7393901A/en
Publication of WO2001079241A1 publication Critical patent/WO2001079241A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • Glycoside esters and their production and use in cosmetics, pharmaceuticals and food or feed
  • the present invention relates to new, biologically active glycoside esters, processes for their preparation, cosmetic and / or pharmaceutical preparations containing these compounds, and food and feed containing these compounds.
  • active ingredients are becoming increasingly important in cosmetics.
  • the active ingredients that are already used in cosmetics are not always natural substances.
  • the optimization of known active ingredients and the production of new active ingredients are the subject of much research.
  • active substances are substances that - occurring or supplied in relatively small amounts - can have a great physiological effect.
  • active substances are substances that - occurring or supplied in relatively small amounts - can have a great physiological effect.
  • hormones vitamins, enzymes, trace elements etc.
  • pharmaceuticals medicinal substances
  • feed additives fertilizers
  • Glvkoside and arylaliphatic Glvkosidester The derivatizations carried out according to the invention achieve an improved effect as well as an increased bioavailability, as was shown earlier with the example of salicin derivatives.
  • salicin a glycosidic active ingredient from willow bark
  • NSAIA non-steroidal anti-inflammatory agent
  • esters such as phenylacetoyl salicin or phenylbutyroyl salicin
  • extracts of the plants of the species Ericaceae e.g. from the bearberry (Arctostaphylos uva ursi), which isolates the glycoside arbutin, which shows skin-lightening effects.
  • This glycoside has a certain biotechnological interest, because in Japan it is used in cosmetics in considerable quantities (1-2 t per year) due to its brightening effect due to the inhibition of melanin biosynthesis (inhibition of the key enzyme tyrosinase). While in the European market the preparations are used more against age spots, liver spots or freckles, in the Asian market the beauty ideal of light, flawless skin is to be achieved through full-body treatment.
  • Alkyl polyglycosides APG
  • Alkyl polyglucosides are used as phosphate-free neutraltenes Detergents and cosmetics added (based on renewable raw materials). 1-7 glucose units are glycosidically linked to a fatty alcohol (mostly 12 carbon atoms):
  • Natural oils e.g. from sunflower oil, linseed oil, olive tree oil
  • PUFAs polyunsaturated fatty acids
  • the PUFAs are part of the diet the group of essential fatty acids and also show a positive effect when used in the prophylaxis of arteriosclerosis.
  • pharmaceutical effects are also important: they can have anti-inflammatory effects (inhibition of prostaglandin or leukotriene synthesis), but also thrombolytic and hypotensive effects.
  • PUFA is defined as a polyunsaturated fatty acid with 16 to 26 carbon atoms, the fatty acid having at least four isolated and / or at least two conjugated double bonds.
  • PUFAs are the twelve octadecadienoic acids (which occur in nature) which are isomeric to linoleic acid (ice, ice, 9,12-octadecadienoic acid) and which have conjugated double bonds on the C atoms 9 and 11, 10 and 12, or 11 and 13 have.
  • linoleic acid e.g. ice, trans, 9,11-octadecadienoic acid, trans, ice, 10,12-octadecadienoic acid, ice, ice, 9,11-octadecadienoic acid, trans, ice, 9,11-octadecadienoic acid, trans, trans, 9,11-octadecadienoic acid, ice, ice, 10,12-octadecadienoic acid, ice, trans, 10,12-octadecadienoic acid, trans, trans, 10,12-octadecadienoic acid
  • CLA mixtures eg Edenor UKD 6010, Henkel KGaA
  • conjugated double bonds are also referred to as "conjugated linoleic aids" (CLAs). They are naturally obtained as a mixture mainly from milk and meat from ruminants (5 mg / g fat), in which they are synthesized by the rumen bacterium Butyrivibrio fibrisolvens.
  • CLAs conjugated linoleic aids
  • CLAs The effect of the CLAs is very versatile. They show inhibitory effects in carcinogenesis and in artherogenesis. They also show an antioxidant effect through furan formation, which plays an important role in the prevention of cancer and coronary heart diseases (CHDs).
  • CHDs cancer and coronary heart diseases
  • CLAs as a mixture of isomers follows from their competent action as anti-inflammatory agents, since, due to their structural relationship to arachidonic acid, the precursor of the inflammation mediator prostaglandin, they can competitively inhibit the desaturases required for the biosynthesis of prostaglandins. They also displace the precursors arachidonic and eicosanoic acid from the phospholipids and inhibit the conversion of arachidonic acid to eicosanoic acid and thus the conversion to prostaglandins.
  • the object on which the present invention is based was therefore to provide such substances which have few side effects, have a good action and are easy to process and apply.
  • glycosides and certain glycoside esters are e.g. known from nature.
  • esters described here, in particular PUFA and CLA esters, of unsaturated fatty acids with sugars or glycosides in which at least one of the hydroxyl groups of the sugar contains an (unsaturated one) are not known (neither from plants, microorganisms or animal cells nor synthetically produced) ) Carbon or Fatty acid is esterified.
  • esters in particular esters of unsaturated fatty acids with sugars or glycosides, have improved bioavailability, increased activity and / or a broader spectrum of activity than the known individual components (fatty acid or sugar / glycoside).
  • the ester is preferably formed by means of the primary Hydroxyl group of sugar / glycoside; however, the other OH groups on the sugar or any OH groups present in the aglycone (eg hydroxyl radical in the case of arbutin) can also be used for the esterification.
  • R is a hydrogen, a branched or straight-chain C 8 -C 2 o-alkyl bonded to the sugar via an ether bridge, an arylalkyl or a substituted or unsubstituted C ⁇ -Cio-aryl radical, in which Z (sugar) is a mono-, disaccharide or polysaccharide which is substituted n-times with ester and with Ac and if R is not hydrogen, acetal to the
  • the radical R is bound, where Ac is a polyunsaturated C 15 -C 25 acyl radical with at least 4 isolated and / or at least two conjugated double bonds or an arylaliphatic one
  • Residue with 1-4 methylene groups between ester group and aromatic ring in which m is an integer (1, 2, 3, ...) including 0, in which n is an integer (1, 2, 3, ... ), but not 0, with the proviso that Z-0-R m is not salicin, which is 2-hydroxymethylphenyl) -ß-glucopyranoside.
  • Preferred fatty acids are CLAs and stearidonic acid, particularly preferred are the octadecadienoic acids which have conjugated double bonds on the C atoms 9 and 11, 10 and 12 or 11 and 13, in particular the eis, trans, 9, 11 and the eis, eis , 9, 11-octadecadienoic acid.
  • Suitable sugars are mono-, di- and oligosaccharides, especially D-glucose, D-galactose, D-xylose, D-apiose, L-rhamnose, L-arabinose and rutinose, with D-glucose being particularly preferred.
  • glycosides (Z-0-R m ) are monosaccharides (such as those mentioned in the preceding paragraph) containing compounds, in particular arbutin, fragilin and populin, but also glycosides containing oligo- or polysaccharides, such as alkyl polyglucosides, especially APG (Henkel KGaA ).
  • esters 1 to 30 are the following esters 1 to 30, in which both m and n are 1, in which Ac, Z and R have the following meanings and in which the ester group is formed via the primary alcohol group of the sugar / glycoside (if several glucose or sugar units are present, there is esterification at the primary OH of the glucose unit, which is also glycosidically linked to, for example CH 3 - (CH 2 ) ⁇ o-CH 2 OH):
  • esters 31 to 60 which differ from the esters 1 to 30 only in that the sugar unit (s) does not consist of D-glucose, but instead of the corresponding number of D-galactose units.
  • esters 121 to 180 in analogy to the esters 61 to 120, which differ from the latter in that the second Ac residue is not on the 4-OH but on the 1-OH of the glucose or galactose Unit sits.
  • esters 181 to 240 in analogy to the esters 121 to 180, which differ from the latter in that the second Ac residue is not on the 1-OH but on the 2-OH of the glucose or galactose Unit sits.
  • esters 301 to 360 are the following esters 301 to 360 in analogy to esters 241 to 300, which differ from the latter in that the three Ac residues on the primary and the 2-OH and the 4-OH group of the Sugar are bound.
  • the modification of the fatty acids according to the invention ie the derivatization of the fatty acids in the form of the compounds of the present invention described above, improves the tolerance and the bioavailability and effect of such fatty acids for use in cosmetics, pharmacy and / or nutrition.
  • aspects of the present invention relate to the use of the compounds of the general formula (I) for the production of cosmetic and pharmaceutical preparations, their use as additives to food, nutritional supplements and animal feed. Further aspects of the present invention relate to pharmaceutical and cosmetic preparations and to food, nutritional supplements and animal feeds which contain at least one compound of the general formula (I).
  • the invention accordingly furthermore relates to a process for the preparation of the compounds of the formula (I) according to the invention, which is characterized in that a sugar Z or a glycoside Z-0-R m with an unsaturated fatty acid AcOH or with an ester, preferably a methyl or ethyl ester, this fatty acid AcOH is esterified in the presence of a lipase.
  • Suitable enzymatic catalysts for the esterification (by transesterification) of the acids and alcohol components mentioned include the hydrolases, especially the lipases such as the lipases from Candida antarctica, Candida rugosa (formerly Candida cylandracea), Geotrichum candidum, Aspergillus niger, Penicillium roqueforti, Rhizopus arrhizus and Mucor miehei.
  • a preferred lipase is the lipase (isoenzyme B) from Candida antarctica, for which there are two reasons. First, it shows a particularly high selectivity in the esterification of the acetals with the unsaturated fatty acids, although these are not among their typical substrates. Furthermore, it shows no interface activation (a crucial feature for the classification of hydrolases in the group of lipases), since it lacks an important lipase structural feature, a movable peptide chain at the active center (so-called lid).
  • region-specific means that only a certain OH group of a polyol is esterified.
  • regioselective means that a particular OH group of a polyol is preferably, but not exclusively, esterified.
  • the purification can also be carried out by a chromatographic process on silica gel, preferably with ethyl acetate / methanol or dichloromethane / methanol mixtures with small proportions of acetic acid and / or water, which can also be carried out in addition to an aqueous two-phase extraction process with organic solvents.
  • esters of formula (I) according to the invention have good bioavailability and activity, they can be used in cosmetic and pharmaceutical preparations and / or as food additives, with the result that the quality of these products is significantly improved.
  • the esters of conjugated linoleic acids (CLAs) according to the invention have an anti-inflammatory, antipyretic, anti-inflammatory and / or analgesic effect and also have antioxidative, skin-lightening or antibacterial / antiviral effects.
  • the fat depot-reducing effect of the CLAs is also evident in the compounds according to the invention.
  • the compounds of formula (I) have good bioavailability and activity, they can be used in cosmetic and pharmaceutical preparations and / or as food additives, with the result that the quality of these products is significantly improved.
  • the compounds according to the invention can be incorporated particularly well into lipophilic base formulations and can be easily formulated as stable emulsions.
  • the compounds of formula (I) according to the invention are used for the production of cosmetic and / or pharmaceutical preparations and / or food or feed.
  • the invention further relates to the use of the compounds of the formula (I) for the production of cosmetic and / or pharmaceutical preparations; the use as food supplements or additives in food preparations and in feed (e.g. for animal breeding); cosmetic and pharmaceutical preparations as well as food preparations and animal feeds containing (a) compound (s) of the formula (I).
  • the cosmetic preparations obtainable using the compounds (I) according to the invention such as hair shampoos, hair lotions, foam baths, shower baths, creams, gels, lotion, alcoholic and aqueous / alcoholic solutions, emulsions, wax / fat masses, stick preparations, powder or Ointments can also be used as further auxiliaries and additives, mild surfactants, oil bodies, emulators, superfatting agents, pearlescent waxes, consistency agents, thickeners, polymers, silicone compounds, fats, waxes, stabilizers, biogenic active substances, deodorant substances, Contain antidandruff agents, film formers, swelling agents, UV light protection factors, antioxidants, hydrotropes, preservatives, insect repellents, self-tanners, solubilizers, perfume oils, dyes, germ-inhibiting agents and the like.
  • the amount of the compounds according to the invention used in the cosmetic preparations is usually in the range from 0.01 to 5% by weight, but preferably from 0.1 to 1% by weight, based on the total amount of the preparations.
  • the compounds of the general formula (I) according to the invention optionally in combination with other active substances, together with one or more inert customary carriers and / or diluents, for.
  • B. with corn starch, milk sugar, cane sugar, microcrystalline cellulose, magnesium stearate, polyvinylpyrrolidone, citric acid, tartaric acid, water, water / ethanol, water / glycerin, water / sorbitol, water / polyethylene glycol, propylene glycol, carboxymethyl cellulose or fatty substances such as hard fat or the like suitable mixtures, work into conventional galenical preparations such as tablets, dragees, capsules, powders, suspensions, drops, ampoules, juices or suppositories.
  • the daily dosage required to achieve a corresponding effect in pharmaceutical applications is advantageously 0.1 to 10 mg / kg body weight, preferably 0.5 to 2 mg / kg body weight.
  • the nutritional substitutes and additives, such as sports drinks, obtainable using the compounds of the formula (I) according to the invention suitably contain the compounds (s) of the formula (I) in an amount which, with a normal need for fluid intake of 1 up to 5 liters per day leads to a dosage of these compounds of 0.1 to 10 mg, preferably 0.5 to 5 mg, per kg of body weight.
  • An example of use in the food industry is for the compounds of the formula (I) as colorings and / or spices. Examples
  • reaction was carried out by means of thin layer chromatography (silica gel 60 plates with fluorescent indicator; eluent: ethyl acetate / methanol 10: 1, v / v and dichloromethane / methanol / acetic acid 95: 5: 0.1, v / v / v; visualization: UV detection as well as by means of an acetic acid /
  • ⁇ (cis-cis isomer) 14.4 (C-18), 23.8 (C-17), 25.6 (C-3) 30.1-30.7 (C-4, C-5, C-6, C-7, C- 14, C-15, C-16), 32.6 (C-13), 33.6 (C-8), 34.4 (C-2), 64.8 (C-6 '), 70.4 (C-4'), 71.8 ( C- 5 '), 73.8 (C-2'), 74.9 (C-3 '), 93.8 (C-1'), 126.8 (C-11) 129.7 (C-10), 130.2 (C-9), 131.6 (C-12), 174.8 (C-1).
  • Example 2 CLA + alkyl polyglycoside (APG) 6-0-cis-9, trans-11-octadecadienoyl-alkylglucoside 2 g APG (Henkel KGaA), 15 g Edenor UKD6010, 4.5 g molecular sieve, 10 ml t-butanol and 4.5 g immobilized lipase B from Candida antarctica were incubated for 48 hours at 60 ° C with 100 rpm using a magnetic stirrer in a 250 ml Erlenmeyer flask.
  • APG alkyl polyglycoside
  • the reaction was carried out by means of thin layer chromatography (silica gel 60 plates with fluorescence indicator; eluent: ethyl acetate 100%, visualization: UV detection and using acetic acid / sulfuric acid / anisaldehyde immersion reagent (100: 2: 1 v / v / v)).
  • the product was enriched in the hexane phase by means of an aqueous two-phase extraction, concentrated in a rotary evaporator and purified by column chromatography (silica gel F60; mobile phase: ethyl acetate / methanol (10: 1, v / v)).

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Abstract

L'invention concerne des composés de formule générale (I) Acn-O-Z-O-Rm (I), dans laquelle R désigne un reste hydrogène, un reste alkyle C8-C20 ramifié ou linéaire, lié au sucre par l'intermédiaire d'un pont éther, un reste arylalkyle ou un reste aryle C6-C10 substitué ou non substitué ; Z (sucre) désigne un mono-, un di- ou un polysaccharide, substitué n-fois par Ac à la manière d'esters et lié au reste R de manière acétalique, si R ne désigne pas hydrogène ; Ac désigne un reste acyle C15-C25 insaturé plusieurs fois ayant au moins 4 liaisons doubles isolées et/ou au moins deux liaisons doubles conjuguées, ou un reste arylaliphatique ayant entre 1 et 4 groupes méthylène entre le groupe ester et le composé cyclique aromatique ; m désigne un nombre entier (1,2,3, ) 0 compris ; n désigne un nombre entier (1,2,3, ) mais pas 0, sous réserve que Z-O-Rm ne désigne pas salicine, c'est-à-dire 2-(hydroxyméthyl-phényl)-β-glucopyranoside.
PCT/EP2001/004153 2000-04-18 2001-04-11 Esters de glycoside, leur preparation et leur utilisation comme agents cosmetiques, pharmaceutiques et comme produits alimentaires et substances fourrageres WO2001079241A1 (fr)

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DE10019255.6 2000-04-18
DE10019255A DE10019255A1 (de) 2000-04-18 2000-04-18 Glykosid-Ester und ihre Herstellung sowie Verwendung in Kosmetika, Pharmazeutika und Nahrungs- bzw. Futtermitteln

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Cited By (6)

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WO2004033475A1 (fr) * 2002-10-10 2004-04-22 National Institute Of Advanced Industrial Science And Technology Agents de regulation de l'activite de la tyrosinase, procede de production desdits agents et preparations externes contenant lesdits agents
US7547752B2 (en) 2002-10-17 2009-06-16 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Scalp treatment
RU2484826C1 (ru) * 2012-02-17 2013-06-20 Государственное бюджетное образовательное учреждение высшего профессионального образования "Алтайский государственный медицинский университет" Министерства здравоохранения и социального развития Российской Федерации Средство, обладающее мочегонным действием
AU2013202828B2 (en) * 2006-10-26 2013-12-12 Xyleco, Inc. Processing biomass
US9309545B2 (en) 2008-04-30 2016-04-12 Xyleco, Inc. Processing biomass
US9745604B2 (en) 2008-04-30 2017-08-29 Xyleco, Inc. Processing biomass

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