Anticorrosion method

Abstract

Provide a new and highly effective preservative that can fight microorganisms. 【Solution】Proposed is a method for improving the antimicrobial stability of a composition containing or consisting of glycolipids. The glycolipid is selected from ustilagic acid or compounds 1 to 6 according to at least one of formula (I) to formula (III).

Description

Technical Field

[0001] The present invention relates to the field of glycolipids and relates to a novel and effective method for preserving preparations using a naturally derived antimicrobial agent.

Background Art

[0002] The increase in resistant microorganisms indicates a further need for compounds that can prevent microbial infections and contaminations while showing low toxicity to humans. Some glycolipids, such as ustilagic acid, exhibit antimicrobial properties. For example, glycolipids have been shown to interact with the lipid bilayer of microorganisms, causing deformation and disruption of the membrane skeleton. Glycolipid treatment also increases the generation of reactive oxygen species (ROS) in bacteria and fungi. The accumulation of reactive oxygen occurs due to insufficient cell detoxification. The accumulation of reactive oxygen is commonly observed in microorganisms after treatment with membrane-disrupting agents and antibiotics and leads to apoptosis of the cells. Therefore, since glycolipids show high biological activity against microorganisms but low toxicity, their application as antimicrobial agents is expected.

[0003] Glycolipids are particularly useful as food preservatives but are also useful in other daily life products, such as pet food and cosmetics. Preservation methods such as pasteurization and the addition of chemical preservatives such as sorbic acid and benzoic acid can have a significant impact on the sensory properties of the product. However, the sensory changes associated with preservation are undesirable because customers value natural flavors. Furthermore, the precursor compounds used in industrial production have high environmental costs, and there is a need for alternatives to synthetically produced preservatives. Glycolipids, due to their antimicrobial properties, low toxicity, and more environmentally friendly production, are a suitable alternative to the widely used preservation methods.

[0004] Glycolipids containing cellobiose glycolipids (such as ustilagic acid) are well known as surfactants and have shown moderate antimicrobial activity by disrupting the cell walls of microorganisms, particularly yeasts and Gram-positive bacteria. (Non-Patent Document 1, Non-Patent Document 2)

[0005] Patent Document 1 discloses usnic acid and its esters for combating specific bacteria such as Alicyclobacillus acidoterrestris, Penicillium expansum, Gluconacetobacter liquefaciens, Lactiplantibacillus plantarum, Zygosaccharomyces rouxii, Aspergillus brasiliensis, Brettanomyces nardensis, Weissella confusa, etc. in non-alcoholic beverages.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Non-Patent Documents

[0007]

Non-Patent Document 1

Non-Patent Document 2

Summary of the Invention

Means for Solving the Problems

[0008] The resistance of specific microorganisms, particularly bacteria such as the following, has increased. - Asaia siamensis - Bacillus licheniformis - Bacillus subtilis - Byssochlamys fulva - Byssochlamys nivea - Candida parapsilosis - Clostridium perfringens - Clostridium sporogenes - Corynebacterium xerosis - Enterococcus faecalis - Lactobacillus paracasei ssp. paracasei - Leuconostoc lactis - Leuconostoc mesenteroides - Malassezia furfur - Neosartorya fischeri - Penicillium paneum - Saccharomyces cerevisiae - Yarrowia lipolytica - Zygosaccharomyces rouxii

[0009] There is a need for new and highly effective preservatives that can combat microorganisms found in many products of daily life, especially those obtained from natural sources and that can fight these microorganisms at very low application levels, if possible.

[0010] The preservative composition of the present invention is preferably applied to foods excluding beverages.

Mode for Carrying Out the Invention

[0011] The first object of the present invention relates to a method for improving the antimicrobial stability of a composition, such as a cosmetic, a detergent or a food preparation, against at least one of the following microorganisms. - Asaia siamensis - Bacillus licheniformis - Bacillus subtilis - Bisoclamys fulva - Bisoclamys nivea - Candida parapsilosis - Clostridium perfringens - Clostridium sporogenes - Corynebacterium xerosis - Enterococcus faecalis - Lactobacillus paracasei ssp. paracasei - Leuconostoc lactis - Leuconostoc mesenteroides - Malassezia furfur - Neosartorya fischeri - Penicillium paneum - Saccharomyces cerevisiae - Yarrowia lipolytica - Zygosaccharomyces bailii This method comprises, (a) providing a composition in need of improved antimicrobial stability; (b) providing at least one glycolipid and optionally at least one other antimicrobial agent; (c) adding to the composition the amounts of said at least one glycolipid and optionally said at least one other antimicrobial agent; (d) optionally, providing to the composition at least one other compound that affects the solubility of the compounds added in steps (b) and (c); and consists of or consists only of, (e) The glycolipid represents an ester of ustilagic acid or an ester of ustilagic acid esterified with a linear C1-C4 aliphatic alcohol. In some embodiments, the method may further comprise, optionally in step (e), adjusting the pH of the composition thus obtained to about 1 to about 4.

[0012] Glycolipid A glycolipid is a molecule having at least one glycosidic bond between a monosaccharide or oligosaccharide and a lipid molecule. Several classes of glycolipids have been identified, such as rhamnolipids, trehalose lipids, cellobiose lipids, mannosylerythritol lipids, etc. Ustilagic acid has the formula C 36 H 64 O 18 It is an organic compound represented by. This acid is a cellobiose lipid produced by the corn smut fungus Ustilago Maydis under nitrogen-deficient conditions. This acid was discovered in 1950 and has been proven to be an amphiphilic glycolipid with surfactant properties. The name is derived from the Latin USTUS, meaning burnt, and is derived from the burnt appearance of the smut fungus. Yeasts of the genus Pseudozyma are known to produce ustilagic acid. For example, Pseudozyma Fusiformata and Pseudozyma Graminicola secrete 2-O-3-hydroxyhexanoyl-β-D-glucopyranosyl-(1→4)-6-O-acetyl-β-D-glucopyranosyl-(1→16)-2,15,16-trihydroxyhexadecanoic acid. As a similar compound, there is the extracellular cellobiose lipid of the yeasts Cryptococcus Humicola and Trichosporon Porosum: 2,3,4-O-triacetyl-β-D-glucopyranosyl-(1→4)-6-O-acetyl-β-D-glucopyranosyl-(1→16)-2,16-dihydroxyhexadecanoic acid. Among glycolipids, there are those that can be used as natural preservatives without changing the sensory properties of the product. Ustilagic acid has been shown to have properties as an antibiotic (US2698843). The biosynthesis of ustilagic acid and its use as a compound for controlling the plant pathogen Botrytis Cinerea have also been reported previously. (http: / / archiv.ub.uni-marburg.de / opus / frontdoor.php?source gpus=234 2&la=de).

[0013] Surprisingly, the glycolipids of the present invention are active against a wide range of microorganisms including bacteria, fungi, and yeasts, and are particularly active against the following microorganisms. - Acacia siamensis - Bacillus licheniformis - Bacillus subtilis - Bisoclamys fulva - Bisoclamys nivea - Candida parapsilosis - Clostridium perfringens - Clostridium sporogenes - Corynebacterium xerosis - Enterococcus faecalis - Lactobacillus paracasei ssp. paracasei - Leuconostoc lactis - Leuconostoc mesenteroides - Malassezia furfur - Neosartorya fischeri - Penicillium paneum - Saccharomyces cerevisiae - Yarrowia lipolytica - Zygosaccharomyces bailii Considering that each composition is adjusted to a low pH value of from about 1 to about 4, preferably from about 1 to about 3, more preferably from about 2 to about 2.5, it is already used at a very low working level. The product is usually obtained or obtainable by extraction from natural sources.

[0014] The glycolipids according to the invention are known to have excellent emulsifying and surfactant properties. Thus, in a preferred embodiment, the glycolipids according to the invention replace or supplement the emulsifiers and surfactants present in the compositions according to the invention.

[0015] Preferred glycolipids In a preferred embodiment, the glycolipids according to the invention conform to formula (I).

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0016] In a preferred embodiment, the glycolipid according to the present invention follows formula (II). [Chemical formula] Formula (II) Here, independently of each other R1 represents hydrogen or -COCH3, R2 represents hydrogen or the following formula, [Chemical formula] m = 1, 2 or 3; R3 represents hydrogen or -OH, R4 represents -OH or -OCH3, or represents a salt of the glycolipid.

[0017] In a preferred embodiment, the glycolipid according to the present invention follows formula (III). [Chemical formula] Formula (III) Here, independently of each other R1 represents hydrogen or -CH, R2 represents hydrogen or the following formula, [Chemical formula] or [Chemical formula] m = 1, 2 or 3; or represents a salt of the glycolipid.

[0018] Surprisingly, all antimicrobial compounds of the present invention are active against most of the above microorganisms, but certain compounds show exceptionally high and broad activity. In particular, compounds following the general structure of formula (III) can inhibit the growth and viability of microorganisms at even lower working concentrations compared to other glycolipids.

[0019] Compounds 1 to 6 according to the general formula of formula (III) exhibit excellent antimicrobial properties, especially at low concentrations. In a preferred embodiment, the glycolipids according to the present invention are selected from the following formulas of compounds 1 to 6: [Table A1] [Table A2] Or a salt of said glycolipid.

[0020] In a preferred embodiment, the salts according to the present invention represent alkali salts, alkaline salts, alkaline earth salts, ammonium salts, alkanolammonium salts, glucammonium salts or mixtures thereof.

[0021] In a preferred embodiment, at least one glycolipid according to the present invention is added in an amount of 1 to 1,000 ppm, calculated on the composition.

[0022] In a preferred embodiment, at least one glycolipid according to the present invention is added in an amount of 10 to 200 ppm, calculated on the composition.

[0023] In a preferred embodiment of the method, the pH value of the composition is adjusted by inorganic or organic salts.

[0024] Secondary additional antimicrobial compounds In a preferred embodiment, the anti-corrosion method according to the present invention may include a blend of said glycolipid, additional antimicrobial compounds different from said glycolipid (e.g., those described in the European Parliament and Council Regulation (EC) No 1333 / 2008 of 16 December 2008 on food additives or the European Parliament and Council Regulation (EC) No 1223 / 2009 of 30 November 2009 on cosmetics), and further compounds such as saponins that affect the solubility of said glycolipid and emulsifiers described in EU 1333 / 2008 or EU 1223 / 2009.

[0025] A suitable species may be selected from the group consisting of preservatives selected from the group consisting of the following. Benzoic acid and p-hydroxybenzoic acid, their esters and salts, benzyl benzoate, propionic acid and its salts, salicylic acid and its salts, 2,4-hexadienoic acid (sorbic acid) and its salts, levulinic acid and its salts, anisic acid and its salts, perillic acid and its salts, cinnamic acid and its salts, formaldehyde and paraformaldehyde, 4-hydroxybenzaldehyde, ortho-, meta-, and para-anisaldehyde, cinnamaldehyde, cinnamic alcohol, 2-hydroxybiphenyl ether and its salts, 2-zinc sulfide pyridine N-oxide, inorganic sulfites and bisulfites, sodium iodate, chlorobutanol, 4-ethylmercury-(II)-5-amino-1,3-bis(2-hydroxybenzoic acid), its salts and esters, dehydroacetic acid, formic acid, 1,6-bis(4-amidino-2-bromophenoxy)-n-hexane and its salts, sodium ethylmercury(II)-thiosalicylate, phenylmercury and its salts, 10-undecenoic acid and its salts, 5-amino-1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine, 5-bromo-5-nitro-1,3-dioxane, 2-bromo-2-nitro-1,3-propanediol, 2,4-dichlorobenzyl alcohol, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 4-chloro-m-cresol, 2,4,4'-trichloro-2'-hydroxy-diphenyl ether, 4-chloro-3,5-dimethylphenol, 1,1'-methylenebis(3-(1-hydroxymethyl-2,4-dioxymidazolidin-5-yl)urea), poly(hexamethylenediguanidine) hydrochloride, (benzyloxymethoxy)methanol hexamethylenetetramine, 1-(3-chloroallyl)-3,5,7-triaza-1-azonia-adamantane chloride, 1-(4-chlorophenoxy)-1-(1H-imidazol-1-yl)-3,3-dimethyl-2-butanone, 1,3-bis-(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione, 1,2-dibromo-2,4-dicyanobutane, 2,2'-Methylenebis(6-bromo-4-chlorophenol), bromochlorophenol, 5-chloro-2-methyl-3(2H)-isothiazolinone, 2-methyl-3(2H)-isothiazolinone and a mixture of magnesium chloride and magnesium nitrate, 2-octyl-2H-isothiazol-3-one, 1,2-benzisothiazol-3(2H)-one, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-1,2-propanediol (chlorphenesin), 2-chloroacetamide, chlorhexidine, chlorhexidine acetate, chlorhexidine gluconate, chlorhexidine hydrochloride, N-alkyl(C, 12 -C 22 ) trimethylammonium bromide and chloride, 4,4-dimethyl-1,3-oxazolidine, N-hydroxymethyl-N-(1,3-di(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)-N'-hydroxymethylurea, 1,6-bis(4-amidinophenoxy)-n-hexane and its salts, glutaraldehyde, 5-ethyl-1-aza-3,7-dioxabicyclo(3.3.0)octane, 3-(4-chlorophenoxy)-1,2-propanediol, hyamine, alkyl-(C8-C 18 )-dimethyl-benzyl-ammonium chloride, alkyl-(C8-C 18 )-dimethyl-benzyl-ammonium bromide, alkyl-(C8-C 18)-Dimethyl-benzyl-ammonium saccharinate, benzyl hemiformal, 3-iodo-2-propynyl butylcarbamate, sodium hydroxymethylaminoacetate or hydroxymethylaminoacetic acid sodium salt, imidazolidinyl urea, diazolidinyl urea, sodium hydroxymethylglycinate, DMDM hydantoin, tropolone, (ethylenedioxy)dimethanol, 2-bromo-2-(bromomethyl)pentanedinitrile, N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine, α,α‘,α“-trimethyl-1,3,5-triazine-1,3,5(2H,4H,6H)-triethanol, pyridine-2-thiol-1-oxide, sodium salt, tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 1,3-bis(hydroxymethyl)-1-(1,3,4-tris(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)urea (diazolidinyl urea), 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione, 3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one, cetylpyridinium chloride, caprylic hydroxamic acid, sorbohydroxamic acid and mixtures thereof; 1,3-propanediol, methylpropanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, 1,2-decanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,2-decanediol, ethylhexyl glycerin, hexoxypropane-1,2-diol, heptoxypropane-1,2-diol, octoxypropane-1,2-diol, 3-phenoxypropane-1,2-diol, 3-benzyloxypropane-1,2-diol, 3-phenylethyloxypropane-1,2-diol, 3-phenylpropoxypropane-1,2-diol, 3-methylbenzyloxypropane-1,2-diol, sorbitan caprylate, triclosan, clotrimazole, octopirox (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone, 2-Aminoethanol), chitosan, farnesol, 2-butyl octanoic acid, 2-benzyl heptan-1-ol, glycerol monolaurate, bis(2-pyridylthio)zinc 1,1’ -dioxide, N,N’ -(decane-1,10-diyl dipyridine-1-yl-4-ylidene)-dioctane-1-amine dihydrochloride (octenidine dihydrochloride), thymol, eugenol, benzyl alcohol, 2-phenylethyl alcohol, 3-phenylpropanol, 2-phenoxyethanol, 1-phenoxypropan-2-ol, 3-phenoxypropanol, benzyloxymethanol, 4-hydroxyacetophenone, lactic acid, ethanol, pHB (ester) and mixtures thereof.

[0026] In a preferred embodiment, the secondary additional antimicrobial compound is selected from the group consisting of benzoic acid and 2,4-hexadienoic acid (sorbic acid), lactic acid, ethanol and para-hydroxybenzoic acid (pHB), their esters and salts.

[0027] Solubilizer (dissolving agent) A further object of the present invention is to improve the solubility of the selected glycolipids and other compounds, and of the glycolipids and their mixtures in aqueous solution, depending on the desired pH value. Therefore, it is beneficial for the present invention to further add compounds that enhance the solubility for different combinations of glycolipids at various pH values. For example, the solubility of ustilagic acid decreases at low pH values. Surprisingly, when adding plant-derived saponins, the solubility at low pH values increases significantly and additional antimicrobial properties are obtained.

[0028] In a preferred embodiment, the preservation method according to the present invention consists of the group of saponins obtained from plant genera, - Quiallaja, - Yucca, - Dioscorea, - Paris, - Hosta, - Agave, - Asparagus, - Allium, - Sapindus, - Aesculus, - Hedera, - Blighia, - Dipsacus, - Aralia and / or - Anemone or mixtures thereof Emulsifiers E400 to 499, or mixtures thereof, which are approved as food preparations in the EU, Lecithin; polyglycerol esters (PGE), polysorbates, stearoyl lactylates, propylene glycol esters (PGMS), sucrose esters; polyglycerol polyricinoleates (PGPR); ammonium phosphatides (AMP); synthetic food-grade emulsifiers selected from the group consisting of mono- and diglycerides of C6-C22 saturated or unsaturated fatty acids, and mixtures thereof, It may contain a compound that increases the solubility of glycolipids selected from

[0029] Food preparation The food composition according to the present invention is any preparation or composition containing the composition according to the present invention, which is suitable for ingestion and is used for nutritional or enjoyable purposes, and generally is a product intended to be introduced into the oral cavity of a human or animal, remain there for a certain period of time, and then be eaten (e.g., cooked food or feed, see also below) or removed from the oral cavity again (e.g., chewing gum). Such products include any substance or product that a human or animal ingests in a processed, partially processed, or unprocessed state. Also included are substances added to products that are orally ingestible during manufacture, preparation, or processing and are intended to be introduced into the oral cavity of a human or animal.

[0030] The food compositions according to the present invention also include substances that are ingested by humans or animals in an unchanged, processed or prepared state and then digested. In this regard, the orally ingestible products according to the present invention also include casings, coatings, or other encapsulations that are ingested simultaneously or are expected to be ingested. The expression "orally ingestible product" encompasses foods and feeds that can be eaten as such, i.e., foods or feeds that are already complete with respect to substances important for taste. The expressions "foods that can be eaten as such" and "feeds that can be eaten as such" also include solid or semi-solid foods or feeds that can be eaten as such. Examples include frozen products that need to be thawed before eating and heated to a temperature at which they can be eaten. Products such as yogurt, ice cream, chewing gum, and hard caramel are also included in foods and feeds that can be eaten as such.

[0031] Preferred food compositions according to the present invention also include "semi-finished products". As used herein, a semi-finished product is understood to be an orally ingestible product (in particular, a food or feed) that is not suitable for immediate use as an orally ingestible product that can be eaten because of its very high content of flavor and taste substances. The semi-finished product is converted into an orally ingestible product (in particular a food or feed) that can be eaten immediately only by mixing with at least one further component (for example, reducing the concentration of the flavor and taste substances) and optionally by further steps (for example, heating, freezing). Examples of semi-finished products that can be mentioned here are as follows.

[0032] The food composition according to the invention preferably comprises one or more preparations for nutritional or sensory purposes. These include, in particular, (low-calorie) baked goods (such as bread, dry biscuits, cakes and other baked goods), confectionery (such as chocolate, chocolate bars and other bar-shaped products, fruit gums, dragees, hard and soft caramels, chewing gums, etc.), meat products (such as ham, raw sausage or raw sausage preparations, spiced or marinated raw or salted meat products, etc.), eggs or egg products (such as dried eggs, egg whites, egg yolks), cereal products (such as breakfast cereals, muesli bars, cooked ready-to-eat rice products, etc.), dairy products (such as rice pudding, yogurt, kefir, cream cheese, soft cheese, hard cheese, powdered milk, whey, butter, buttermilk, products containing partially or fully hydrolyzed milk proteins, etc.), products made from soy protein or other soy components (such as soy milk and soy milk products, preparations containing soy lecithin, fermented products such as tofu or tempeh or products manufactured therefrom, as well as fruit preparations and optionally mixtures with flavors), fruit preparations (such as jams, sorbets, fruit sauces, fruit fillings), vegetable preparations (such as ketchup, sauces, dried vegetables, frozen vegetables, cooked vegetables, stewed vegetables), snacks (such as baked or fried potato chips or potato-based products, corn or peanut-based extrusions), fat- and oil-based products or their emulsions (such as mayonnaise, remoulade, dressings, in all cases full-fat or low-fat), other cooked dishes and soups (such as dried soups, instant soups, cooked soups), spices, spice mixtures, in particular seasonings used in the field of snacks, for example, sweetening preparations, tablets or sachets, and other preparations for sweetening or whitening food are included. The preparations within the scope of the invention can also be used in the form of semi-finished products for the production of further preparations for nutritional or sensory purposes. Preparations within the scope of the present invention may be in the form of capsules, tablets (uncoated tablets and coated tablets, for example enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in the liquid phase, emulsions, powders, solutions, pastes, or other preparations that can be swallowed or chewed, and in the form of dietary supplements.

[0033] The preparations may also be in the form of capsules, tablets (uncoated tablets and coated tablets, for example enteric coatings), dragees, granules, pellets, mixtures of solids, dispersions in the liquid phase, emulsions, powders, solutions, pastes, or other preparations that can be swallowed or chewed, for example in the form of food supplements.

[0034] The semi-finished products are generally used for the production of preparations for nutritional or recreational purposes that are ready to use or ready to eat.

[0035] As further constituents of preparations or semi-finished products for immediate consumption for nutritional or sensory purposes, there are conventional base substances, adjuncts and additives for food or foodstuffs, such as water, fresh or processed vegetable or animal base substances or mixtures of raw materials (e.g., raw, roasted, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, herbs, nuts, vegetable pastes or mixtures thereof), digestible or indigestible carbohydrates (e.g., sucrose, maltose, fructose, glucose, dextrin, amylose, amylopectin, inulin, xylan, cellulose, tagatose), sugar alcohols (e.g., sorbitol, erythritol), natural or hardened fats (e.g., beef tallow, lard, palm fat, cocoa butter, hardened vegetable fats), oils (e.g., sunflower oil, peanut oil, corn germ oil, olive oil, fish oil, soybean oil, sesame oil, etc.), fatty acids or their salts (e.g., potassium stearate), proteinaceous or non-proteinaceous amino acids and related compounds (e.g., γ-aminobutyric acid, taurine), peptides(Examples: glutathione), natural or processed proteins (such as gelatin), enzymes (such as peptidase), nucleic acids, nucleotides, taste correctors for unpleasant taste impressions, additional taste regulators for additional taste impressions that are generally not unpleasant, other taste regulating substances (such as nucleotides such as inositol phosphate, guanosine monophosphate, adenosine monophosphate, or other substances such as sodium glutamate and 2-phenoxypropionic acid), emulsifiers (such as lecithin, diacylglycerol, gum arabic), stabilizers (such as carrageenan, alginates), preservatives (such as benzoic acid and its salts, sorbic acid and its salts), antioxidants (such as tocopherol, ascorbic acid), chelating agents (such as citric acid), organic or inorganic acidifying agents (e.g., acetic acid, phosphoric acid). Flavors include additives other than spices (such as flavors, sweeteners, glycyrrhizic acid, phosphoric acid), other bitter substances (such as quinine, caffeine, limonene, amalogentin, humulone, lupron, catechol, tannin), substances that prevent enzymatic browning (such as sulfites, ascorbic acid), essential oils, plant extracts, natural or synthetic colorants or coloring pigments (such as carotenoids, flavonoids, anthocyanins, chlorophyll and its derivatives), spices, trigeminal nerve active substances or plant extracts containing such trigeminal nerve active substances, synthetic, natural or natural-equivalent flavors or odorants, and odor correctors.

[0036] Food compositions according to the invention, for example in the form of preparations or semi-finished products, preferably contain a flavor composition in order to complete and refine the taste and / or aroma. The preparation can contain a solid carrier and a flavor composition as components. Suitable flavor compositions include, for example, synthetic, natural or nature-identical flavors, flavoring agents and flavoring substances, reaction flavors, smoke flavors or other flavor-imparting preparations (for example protein (partial) hydrolysates, preferably protein (partial) hydrolysates with a high arginine content, barbecue flavors, plant extracts, spices, spice preparations, vegetables and / or vegetable preparations) as well as suitable auxiliary substances and carriers. Particularly suitable here are those that produce a roasted, meat-like (especially chicken, fish, seafood, beef, pork, lamb, mutton, goat), vegetable-like (especially tomato, onion, garlic, celery, leek, mushroom, eggplant, seaweed), spicy (especially black pepper, white pepper, cardamom, nutmeg, pimento, mustard, mustard products), fried, yeast-like, boiled, fatty, salty, and / or pungent flavor impression and, accordingly, can enhance the spicy impression, or components thereof. The flavor composition generally contains one or more of the aforementioned components.

[0037] The food composition of the invention is preferably selected from the group consisting of the following. - Confectionery, preferably low-calorie or calorie-free confectionery, preferably selected from the group consisting of muesli bars, fruit gums, dragées, hard caramels and chewing gums, - Cereal products, preferably selected from the group consisting of low-sugar / sugar-free breakfast cereals and muesli bars, - Dairy products, preferably selected from the group consisting of low-fat and fat-free yogurts, kefir, whey, buttermilk and ice cream, - Products made from soy protein or other soy components, preferably soy milk, products manufactured from soy milk, preparations containing soy lecithin, products manufactured from preparations containing soy lecithin, and fruit preparations and optionally mixtures with flavorings, selected from the group consisting of - Sweetener preparations, tablets and sachets, - Dragées without using sugar - Ice cream, whether or not containing milk-derived components, preferably sugar-free.

[0038] Food-grade emulsifier Preferred food-grade emulsifiers include the following groups. - Lecithin; - Fatty acid derivatives, such as polyglycerol esters (PGE), polysorbates ("TWEEN"), stearoyl lactylate, propylene glycol esters (PGMS), and sucrose esters; - Polyglycerol polyricinoleate (PGPR); - Ammonium phosphatide (AMP); - C6-C 22 Mono and diglycerides of saturated or unsaturated fatty acids; - Saponin or extracts prepared from saponin-containing plants, such as quillaja extract (E999); and mixtures thereof.

[0039] Aroma or flavor compound Aroma compounds and flavoring agents are well known in the art and can be selected from synthetic flavoring liquids and / or oils obtained from plant leaves, flowers, fruits, etc., and combinations thereof. Representative flavor liquids include artificial, natural or synthetic fruit flavors such as eucalyptus, lemon, orange, banana, grape, lime, apricot and grapefruit oil, as well as fruit essences such as apple, strawberry, cherry, orange, pineapple, flavors derived from beans and nuts such as coffee, cocoa, cola, peanut, almond, and flavors derived from roots such as licorice or ginger.

[0040] Suitable aroma or flavor compounds are described in the Rules of the European Parliament and of the Council (EC) No 1334 / 2008 of 16 December 2008 on flavorings and certain food ingredients with flavoring properties used in or on foods, as well as in Council Regulation (EEC) No 1601 / 91, Regulation (EC) No 2232 / 96, (EC) No 110 / 2008, and the amendment of Directive 2000 / 13 / EC.

[0041] Sweetener Here, the term "sweetener" means a substance having a relative sweetness of at least 25, based on the sweetness of sucrose (thus, the sweetness of sucrose is 1). The sweeteners used in the orally ingestible products (especially foods, feeds or pharmaceuticals) according to the present invention (a) are preferably non-corrosive and / or have an energy content of 5 kcal or less per gram of the orally ingestible product.

[0042] Preferred sweeteners in the orally ingestible products (especially foods, feeds or pharmaceuticals) according to the present invention are selected from the following group. (a) Natural sweeteners. Preferably, it is selected from the group consisting of miraculin, monellin, mabinlin, thaumatin, curculin, brazzein, pentadin, D-phenylalanine, D-tryptophan, and extracts or fractions obtained from natural sources, these amino acids and / or proteins, and physiologically acceptable salts of these amino acids and / or proteins. In particular, sodium, potassium, calcium or ammonium salts, neohesperidin dihydrochalcone, naringin dihydrochalcone, stevioside, steviolbioside, rebaudioside, particularly rebaudioside A, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, rebaudioside G, rebaudioside H, dulcoside and rubusoside, suaibioside A, suaibioside B, suaibioside G, suaibioside H, suaibioside I, suaibioside J, baiyunoside 1, baiyunoside 2, fromisoside 1, fromisoside 2, fromisoside 3 and fromisoside 4, abrusoside A, abrusoside B, abrusoside C, abrusoside D, cyclocarioside A and cyclocarioside I, osthenol, polypodoside A, strogin 1, strogin 2, strogin 4, seriguain A, dihydroquercetin 3-acetate, perillartine, telosmoside A15, periandrin I-V, pterocarioside, cyclocarioside, mukurojidoside, trans-anethole, trans-cinnamaldehyde, brioside, brionoside, brionozylcoside, carnosifloside, scandenoside, dipenoside, trilobatin, phloridzin, dihydroflavanol, hematoxylin, cyanine, chlorogenic acid, albizia saponin, telosmoside, gaudicaucoside, mogroside, mogroside V, hernanzulcin, monatin, philozulcin, glycyrrhetinic acid and its derivatives, particularly glycosides such as glycyrrhizin, and physiologically acceptable salts of these compounds. Furthermore, particularly sodium, potassium, calcium or ammonium salts.And an extract or a concentrated fraction of an extract, which is selected from the group consisting of a Taumatococcus extract (katumfe plant), an extract of the genus Stevia (especially Stevia rebaudiana), a lavender extract (Momordica or Siraitia grosvenorii, Luo Han Guo), an extract of the genus Glycerrhiza (especially Glycerrhiza glabra), an extract of the genus Fragaria (especially Fragaria suavissima), a citrus extract, and a Lippia dulcis extract; (b) Synthetic sweeteners. Preferably, it is selected from the group consisting of magap, sodium cyclamate or other physiologically acceptable salts of cyclamic acid, acesulfame K or other physiologically acceptable salts of acesulfame, neohesperidin dihydrochalcone, naringin dihydrochalcone, saccharin, sodium saccharin salt, aspartame, super aspartame, neotame, alitame, advantame, perillartine, sucralose, lugduname, calelerame, sucrononate, and sucrooctate.

[0043] Thickener Advantageous thickeners in the orally ingestible products (especially foods, feeds or pharmaceuticals) according to the present invention are selected from the group consisting of crosslinked polyacrylic acid and its derivatives, polysaccharides and their derivatives, such as xanthan gum, agar, alginate or tylose, cellulose derivatives, such as carboxymethyl cellulose or hydroxycarboxymethyl cellulose, fatty alcohols, monoglycerides and fatty acids, polyvinyl alcohol and polyvinyl pyrrolidone.

[0044] According to the present invention, orally ingestible products (especially foods or feeds) containing milk thickened with lactic acid bacteria and / or cream thickened with lactic acid bacteria, preferably selected from the group consisting of yogurt, kefir and quark, are preferred.

[0045] A food composition according to the invention, comprising milk thickened with lactic acid bacteria and / or cream thickened with lactic acid bacteria, is preferably an orally ingestible product containing probiotics, which are preferably selected from the group comprising Bifidobacterium animalis subsp. lactis BB-12, Bifidobacterium animalis subsp. lactis DN-173 010, Bifidobacterium animalis subsp. lactis DN-173 010, lactis HN019, Lactobacillus acidophilus LA5, Lactobacillus acidophilus NCFM, Lactobacillus johnsonii LA1, Lactobacillus casei Immunitas / Defensis, Lactobacillus casei Shirota (DSM20312), Lactobacillus casei CRL431, Lactobacillus reuteri (ATCC55730), Lactobacillus rhamnosus (ATCC53013).

[0046] Additive for chewing gum An orally ingestible product according to the invention (in particular a food, a feed or a pharmaceutical) is chewing gum, and it is particularly preferred that it contains a chewing gum base. The chewing gum base is preferably selected from the group comprising a chewing gum base or a bubble gum base. The latter is softer and can also form gum bubbles. Preferred chewing gum bases according to the present invention include, in addition to conventionally used natural resins or natural latex chicles, polyvinyl acetate (PVA), polyethylene, (low or medium molecular weight) polyisobutene (PIB), polybutadiene, isobutene-isoprene copolymer (butyl rubber), polyvinyl ethyl ether (PVE), polyvinyl butyl ether, copolymer of vinyl ester and vinyl ether, styrene-butadiene copolymer (styrene-butadiene rubber, SBR), or vinyl elastomers (e.g., elastomers based on vinyl acetate / vinyl laurate, vinyl acetate / vinyl stearate, or ethylene / vinyl acetate), and mixtures of the aforementioned elastomers (e.g., as described in EP 0 242 325, US 4,518,615, US 5,093,136, US 5,266,336, US 5,601,858, or US 6,986,709). Furthermore, the chewing gum bases preferably used according to the present invention preferably contain additional constituents such as, for example, (mineral) fillers, plasticizers, emulsifiers, antioxidants, waxes, fats or fatty oils, such as hardened (hydrogenated) vegetable or animal fats, mono-, di- or tri-glycerides. Suitable (mineral) fillers are, for example, calcium carbonate, titanium dioxide, silicon dioxide, talcum, aluminum oxide, dicalcium phosphate, tricalcium phosphate, magnesium hydroxide and mixtures thereof. Suitable plasticizers, or detackifiers, are, for example, lanolin, stearic acid, sodium stearate, ethyl acetate, diacetin (glycerol diacetate), triacetin (glycerol triacetate), triethyl citrate. Suitable waxes are, for example, paraffin wax, candelilla wax, carnauba wax, microcrystalline wax, polyethylene wax and the like. Suitable emulsifiers are, for example, phosphatides such as lecithin, mono- and di-glycerides of fatty acids, such as glycerol monostearate.

[0047] The chewing gum according to the present invention (in particular those disclosed above) preferably contains different types of sugars, sugar substitutes, other sweetening substances, sugar alcohols (in particular sorbitol, xylitol, mannitol), components having a cooling effect, taste correctors for unpleasant taste impressions, further taste modifiers (for example nucleotides such as inositol phosphates, guanosine monophosphate, adenosine monophosphate, or other substances such as sodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, stabilizers, odor correctors and flavors (for example, eucalyptol, cherry, strawberry, grapefruit, vanilla, banana, citrus fruits, peach, blackcurrant, tropical fruits, ginger, coffee, cinnamon, combinations with the aforementioned flavors such as mint flavors, and spearmint and peppermint alone). In particular, it is particularly important to combine flavors with other substances having cooling, warming, or appetite-enhancing properties.

[0048] Cosmetic preparation

[0049] The preparations according to the present invention include, as anti-dandruff agents, anti-irritation agents, irritation inhibitors, antioxidants, astringents, antiperspirants, preservatives, antistatic agents, binders, buffers, carrier materials, chelating agents, cell stimulants, detergents, care agents, deodorants, antiperspirants, softeners, emulsifiers, enzymes, essential oils, fibers, film-forming agents, fixatives, foam-forming agents, foam stabilizers, foam suppressants, foam boosters, gelling agents, gel-forming agents, hair care agents, hair setting agents, hair straightening agents, moisturizing agents, moisturizing substances, moisture-maintaining substances, bleaching agents, strengthening agents, stain removers, optical brighteners, impregnating agents, antifouling agents, friction reducers, additional auxiliaries and additives such as lubricants, moisturizing creams, ointments, milky agents, plasticizers, coating agents, brightening agents, gloss agents, polymers, powders, proteins, re-oiling agents, abrasives, silicones, hair growth agents, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, ultraviolet absorbers, ultraviolet filters, detergents, thickeners, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, monounsaturated or polyunsaturated fatty acids, Α-hydroxy acids, polyhydroxy fatty acids, liquefiers, dyes, color protectants, pigments, flavoring agents, polyols, surfactants, electrolytes, organic solvents or silicone derivatives, etc. can be used as additional auxiliaries and additives.

[0050] Industrial use The present invention also encompasses the use of glycolipids as antimicrobial agents against at least one of the following microorganisms. - Acacia siamensis - Bacillus licheniformis - Bacillus subtilis - Bisoclamis fulva - Bisoclamis nivea - Candida parapsilosis - Clostridium perfringens - Clostridium sporogenes - Corynebacterium xerosis - Enterococcus faecalis - Lactobacillus paracasei ssp. paracasei - Leuconostoc lactis - Leuconostoc mesenteroides - Malassezia furfur - Neosartorya fischeri - Penicillium paneum - Saccharomyces cerevisiae - Yarrowia lipolytica - Zygosaccharomyces bailii The composition is for preserving at a pH of about 1 to about 4, The glycolipid represents ustilagic acid or an ester of ustilagic acid esterified with a linear C1-C4 aliphatic alcohol.

[0051] In a preferred embodiment, the at least one ustilagic acid or its ester is added in an amount of about 1 to about 1000 ppm, calculated on the composition.

[0052] In a preferred embodiment, the composition is a food preparation excluding cosmetics, detergents or beverages.

[0053] For the sake of good order, it is emphasized that all preferred embodiments described above, especially with regard to combinations, ratios and amounts, also apply to the claimed methods and uses. Therefore, their repetition is not necessary.

Examples

[0054] Manufacturing example Fermentation The Ustilago maydis strain 04507fxxx000001 was stored at -80°C and then revived on a 2% malt extract agar medium. As a seed flask, a 500 ml Erlenmeyer flask equipped with two baffles and closed with a PU foam stopper was used. Each flask containing 100 ml of seed medium (3% malt extract, 0.2% Tween 85, 0.1% agar, pH adjusted to 7.0) was inoculated with 3 to 4 agar pieces from the revival plate. The flasks were cultured at 25°C for 48 hours on an orbital shaker with a 50 mm shaking orbit. The main culture was inoculated at a ratio of 4% of the seed. In the main culture, 9 L of production medium containing 5% dextrose, 0.13% ammonium sulfate, 0.25‰ potassium dihydrogen phosphate, 0.13‰ magnesium sulfate heptahydrate, 0.1‰ sodium chloride, 0.1‰ calcium chloride dihydrate, 1 ml / l of vitamin solution RPMI 1640 (Sigma-Aldrich), and a trace element solution in tap water with the pH value adjusted to pH 6.5 was placed in a 12 L capacity fermenter. The trace element solution contained 5.4 μM iron sulfate, 3.1 μM zinc sulfate, 2.4 μM manganese sulfate, 2.2 μM copper(II) sulfate, 2.1 μM cobalt nitrate, 4.0 μM boric acid, and 0.8 μM sodium molybdate. The fermentation conditions were culturing at 25°C, stirring at 350 rpm with two Rushton-type stirrers, aerating at 0.7 vvm, and controlling the foam with a silicon-based antifoaming agent. After 120 hours of fermentation, the culture was harvested by centrifugation. After centrifugation at 10,000 rcf for 25 minutes, the biomass and ustilagic acid precipitated.

[0055] Extraction and separation of glycolipids Preparation of the extract of the raw material After harvesting, ustilagic acid was contained in the centrifugation precipitate together with the biomass from the fermentation. This precipitate was freeze-dried and extracted with warm ethanol. After evaporating the solvent, an extract of the raw material was obtained.

[0056] Pre-fractionation (fraction) by reverse-phase chromatography The raw material extract was subjected to medium-pressure reverse-phase chromatography to concentrate the target compound. Reverse-phase MPLC can very efficiently remove secondary metabolites such as sugars, lipids, and flavonoids and reach the concentrated fraction of the target compound. For example, it would be reasonable to combine different MPLC pre-fractionation methods to more specifically concentrate the selected saponins by combining RP18 and RP4.

[0057] Second purification step by reverse-phase chromatography The pure compound was isolated by reverse-phase chromatography using different fractions from the first separation step by MPLC. In some cases, several repeated separations by HPLC were required to reach a purity of over 90% per compound. Promising fractions from preparative HPLC runs detected by evaporative light scattering detection (ELSD) were analyzed by LCMS. The solvent of all fractions containing the target compound was removed in vacuo, followed by a lyophilization step. The isolated compounds were characterized by LCMS and 1D and 2D NMR spectroscopy. Isolated compound Table 1 Isolated compounds

Table 1A

Table 1B

Table 1C

Table 1D

[0058] Antimicrobial activity The compound is dissolved at a concentration of 20 mg / mL using 100% DMSO. · Pre-culture: Yeast and bacteria were plated on potato dextrose agar, resuspended in potato dextrose broth, and CFU was determined by OD measurement. Adjust the CFU of the strain in PDB to pH 3.8 Preculture: Spores of mycelium-forming fungi were used directly after thawing frozen stocks of known titers. Final titer used in the assay: 5 x 10 yeast strains 3 CFU / ml, bacteria 1*10 6 CFU / ml, fungus (spores) 5*10 4 CFU / ml Potato dextrose broth pH 3.8 was used as the assay matrix. 500 ppm (0.05%) of the compound was screened (final DMSO 2.5% (v / v)) Volume: 100µl in 96-well format Positive controls: potassium sorbate, sodium benzoate, triclosan 28°C to 30°C, static incubation Incubation time is 2 to 8 days depending on the type of spoilage bacteria. Visual assessment (one eye at a time, with binoculars for fungi) Table 2. List of strains [Table 2A] [Table 2B] Table 3: Antimicrobial activity of test compounds (Minimum inhibitory concentration (MIC) μg / ml) (Color-coded columns: Blue: Compounds specifically claimed in claim 6) [Table 3A] [Table 3B] [Table 3C]

[0059] The examples clearly show that the glycolipids according to the invention exhibit significant activity against a wide range of microorganisms that can generally be found in everyday products such as food, pet food or cosmetics. The performance of the glycolipids according to the invention is comparable to that of sorbic acid and benzoic acid, which are common natural preservatives, and can be synergistically enhanced by blending two or more of the glycolipids according to the invention or by using a blend of the glycolipids with secondary preservatives such as sorbic acid, benzoic acid, lactic acid, ethanol or pHB (ester).

[0060] Formulation example Formulation example Food The following Examples F1 to F2 show various formulations for food preparations. The glycolipid represents one or more glycolipids according to claim 4. Example F1 The formulation of Italian salad dressing is prepared as follows: Component Parts Part I Water 70.0 Vinegar 7.0 Sodium chloride 2.0 Sweetener 4.0 Gum 0.4 Flavor 0.9 Part II Vegetable oil 5.3 Part III Water 6.2 Vinegar 4.2 Spices and flavors 1.8 Mix Part 1 and Part 2 and homogenize. Then add Part 3 and mix well to form a homogeneous mixture. Add 400 ppm of the glycolipid to the dressing. Example F2 Ketchup Aqueous phase Ground tomato 25.9 Apple vinegar 20.7 Water 44.3 Dried tomato 2.1 Sodium chloride 1.8 Minced dehydrated garlic 1.1 Frozen oregano 0.4 Basil 0.5 Xanthan gum 0.2 White onion powder 2.5 Sucrose 7.0 EDTA 0.0007 Glycolipid 0.05 Oil phase Soybean oil 53.3 Olive oil 46.7

[0061] Formulation example Pet food The following Examples P1 to P4 show various formulations for pet food preparations. The glycolipid represents one or more glycolipids as claimed in claim 4. Example P1 In this example, a microbiologically stable food preparation with 60% moisture, simulating meat chunks, suitable for use as dog food will be described. This food is prepared from the following raw materials: Component parts Wheat gluten 10.0 Soybean oil meal 4.0 Poultry meal 3.0 Meat meal 1.5 Corn meal 1.2 Tallow 5.0 Carrageenan 2.5 Potassium sorbate 0.3 Tween 80 0.25 Span 80 0.75 Glycolipid 0.5 Fructose glucose syrup 15.0 Syrup (80% solids, 90% fructose) Water 56.0 To prepare the food, carrageenan is added to water at 70 °C and stirred until dissolved. Tween 80, polyoxyethylene sorbitan monooleate available from Atlas Chemical, potassium sorbate, benzyl alcohol, high fructose corn syrup (Isomerose 900 available from Clinton Corn Products) are added to the carrageenan solution and stirred vigorously until dissolved. The animal fat is melted and sorbitan monooleate (Span 80) available from Atlas Chemical is added and mixed well. Next, the animal fat and the aqueous solution are mixed vigorously to emulsify. The remaining dry ingredients are added with stirring and blended with the emulsion. The resulting mixture is placed in a pot and autoclaved at 15 pounds gauge pressure for 20 minutes to thermally coagulate the mass. The thermally coagulated product is microbiologically stable with a moisture content of 60%. Without the glycolipid component, this formulation is not microbiologically stable. Example P2 In this example, the production of a microbiologically stable food with 70% moisture, simulating a meat mass, from the following materials will be described: Component parts Wheat gluten 7.48 Soybean oil meal 2.96 Poultry meal 2.23 Meat meal 1.11 Corn meal 0.88 Tallow 3.70 Carrageenan 1.85 Potassium sorbate 0.30 Span 80 0.75 Tween 80 0.25 Glycolipid 0.50 Fructose glucose syrup 10.10 Water 66.90 The process is the same as in Example P1. Example P3 In this example, the preparation of a microbiologically stable gravy with a moisture content of 60% will be described. The formulation is as follows: Component parts Meat and bone meal 9.45 Yeast 1.35 Corn flour 1.35 Dried whey 1.35 Total egg solids 1.35 Oyster shell powder 9.45 Fructose / glucose syrup 20.23 Tween 80 0.25 Span 80 0.75 Glycolipid 0.50 Kelcosol 0.14 Water 54.0 In the production method according to this example, first, molten animal fat and Span 80 are mixed. Next, a solution containing high fructose corn syrup, water, potassium sorbate / calcium sorbate, Tween 80, Kelcosol, sodium alginate (available from Kelco Co.), and benzyl alcohol is prepared by heating water to 60 °C and mixing. This solution is vigorously stirred with the animal fat to emulsify. Next, the remaining dry materials are added and stirred vigorously. Heating is not required except for the initial mixing of the fat phase and the water phase. Example P4 In this example, a microbiologically stable gravy preparation with a moisture content of 70% will be described. The following raw materials are combined according to the steps of Example 3: Component parts Meat and bone meal 7.0 Corn flour 1.0 Brewer's yeast 1.0 Dried whey 1.0 Total egg solids 1.0 Oyster shell powder 7.0 Fructose / glucose syrup 15.0 Kelcosol 0.1 Span 80 0.75 Tween 80 0.25 Glycolipid 0.50 Water 65.30

[0062] Formulation example Cosmetics and detergents Examples F1 to F56 below show various formulations for the conditioner. The glycolipid represents one or more glycolipids according to claim 4. Table F1 Liquid soap; transparent (unit: weight%)

Table F1

Table F2

Table F3

Table F4

Table F5

Table F6

Table F7

Table F8

Table F9

Table F10

Table F11

Table F12

Table F13

Table F14

Table F15

Table F16

Table F17

Table F18

Table F19

Table F20

Table F21

Table F22

Table F23

Table F24

Table F25

Table F26

Table F27

Table F28

Table F29

Table F30

Table F31

Table F32

Table F33

Table F34

Table F35

Table F36

Table F37

Table F38

Table F39

Table F40

Table F41

Table F42

Table F43

Table F44

Table F45

Table F46

Table F47

Table F48

Table F49

Table F50

Table F51

Table F52

Table F53

Table F54

Table F55

Table F56

Claims

1. A method for improving the antimicrobial stability of a composition against at least one of the following microorganisms: - Asaia siamensis - Bacillus licheniformis - Bacillus subtilis - Bisoclamys fulva - Bisoclamys nivea - Candida parapsilosis - Clostridium perfringens - Clostridium sporogenes - Corynebacterium xerosis - Enterococcus faecalis - Lactobacillus paracasei ssp. paracasei - Leuconostoc lactis - Leuconostoc mesenteroides - Malassezia furfur - Neosartorya fischeri - Penicillium paneum - Saccharomyces cerevisiae - Yarrowia lipolytica - Zygosaccharomyces bailii (a) providing a composition in need of improved antimicrobial stability; (b) providing at least one glycolipid and optionally at least one other antimicrobial agent; (c) adding to the composition the amounts of said at least one glycolipid and optionally said at least one other antimicrobial agent; (d) optionally, providing to the composition at least one other compound that affects the solubility of the compounds added in steps (b) and (c); comprising or consisting only of: Here, the glycolipid is a method of improving, which represents ustilagic acid esterified with a linear C １ -C ４ aliphatic alcohol.

2. The method according to claim 1, wherein the composition is a cosmetic, a detergent or a food preparation.

3. The method according to claim 1, wherein the glycolipid follows formula (I). 【Chemical 1】 Formula (I) wherein, independently of each other n represents 1 or 2, R １ represents hydrogen or -COCH ３ and R ２ represents hydrogen or has the following formula, [Chemical 2] m = 1, 2 or 3; R ３ represents hydrogen or -OH, R ４ represents -OH or -OCH3, R ５ represents hydrogen or has the following formula, [Chemical Formula 3] or [Chemical Formula 4] m = 1, 2 or 3; R ６ represents hydrogen or -OH, R ７ represents hydrogen, -OH or =O, or represents a salt of said glycolipid.

4. The method according to claim 1, wherein the glycolipid follows formula (II). 【Chemical Formula 5】 Formula (II) wherein, independently of each other R １ represents hydrogen or -COCH ３ and R ２ represents hydrogen or the following formula, 【Chemical Formula 6】 m = 1, 2 or 3; R ３ represents hydrogen or -OH, R ４ represents -OH or -OCH3, or represents a salt of said glycolipid.

5. The method according to claim 1, wherein the glycolipid follows formula (III). 【Chemical Formula 7】 Formula (III) wherein, independently of each other R １ represents hydrogen or -CH, R ２ represents hydrogen or has the following formula, [Chemical Formula 8] or 【Chemical Formula 9】 m = 1, 2 or 3; or represents a salt of said glycolipid.

6. The method according to claim 5, wherein the glycolipid follows at least one of the following formulas (1) to (6). 【Table 1】 【Table 1-2】 or represents a salt of said glycolipid.

7. The method according to claim 3, wherein the salt of the glycolipid represents an alkali salt, an alkaline earth salt, an ammonium salt, an alkanolammonium salt, a glucanammonium salt or a mixture thereof.

8. The method according to claim 1, wherein the at least one glycolipid is added in an amount of from about 1 to about 1,000 ppm, calculated relative to the composition.

9. The method according to claim 1, wherein the at least one glycolipid is added in an amount of from about 10 to about 200 ppm, calculated based on the composition.

10. The method according to claim 1, wherein a secondary antimicrobial agent selected from the following group is added. Benzoic acid and para-hydroxybenzoic acid, their esters and salts, benzyl benzoate, propionic acid and its salts, salicylic acid and its salts, 2,4-hexadienoic acid (sorbic acid) and its salts, levulinic acid and its salts, anisic acid and its salts, perillic acid and its salts, cinnamic acid and its salts, formaldehyde and paraformaldehyde, 4-hydroxybenzaldehyde, ortho-, meta-, and para-anisaldehyde, cinnamaldehyde, cinnamic alcohol, 2-hydroxybiphenyl ether and its salts, 2-zinc sulfide pyridine N-oxide, inorganic sulfites and bisulfites, sodium iodate, chlorobutanol, 4-ethylmercury-(II)-5-amino-1,3-bis(2-hydroxybenzoic acid), its salts and esters, dehydroacetic acid, formic acid, 1,6-bis(4-amidino-2-bromophenoxy)-n-hexane and its salts, sodium ethylmercury(II)-thiosalicylate, phenylmercury and its salts, 10-undecenoic acid and its salts, 5-amino-1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine, 5-bromo-5-nitro-1,3-dioxane, 2-bromo-2-nitro-1,3-propanediol, 2,4-dichlorobenzyl alcohol, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 4-chloro-m-cresol, 2,4,4'-trichloro-2'-hydroxy-diphenyl ether, 4-chloro-3,5-dimethylphenol, 1,1'-methylenebis(3-(1-hydroxymethyl-2,4-dioxymidazolidin-5-yl)urea), poly(hexamethylenediguanidine) hydrochloride, (benzyloxymethoxy)methanol hexamethylenetetramine, 1-(3-chloroallyl)-3,5,7-triaza-1-azonia-adamantane chloride, 1-(4-chlorophenoxy)-1-(1H-imidazol-1-yl)-3,3-dimethyl-2-butanone, 1,3-bis-(hydroxymethyl)-5,5-dimethyl-2,4-imidazolidinedione, 1,2-dibromo-2,4-dicyanobutane, 2,2'-Methylenebis(6-bromo-4-chlorophenol), bromochlorophen, 5-chloro-2-methyl-3(2H)-isothiazolinone, a mixture of 2-methyl-3(2H)-isothiazolinone with magnesium chloride and magnesium nitrate, 2-octyl-2H-isothiazol-3-one, 1,2-benzisothiazol-3(2H)-one, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-1,2-propanediol (chlorphenesin), 2-chloroacetamide, chlorhexidine, chlorhexidine acetate, chlorhexidine gluconate, chlorhexidine hydrochloride, N-alkyl(C, １２ -C ２２ ) trimethylammonium bromide and chloride, 4,4-dimethyl-1,3-oxazolidine, N-hydroxymethyl-N-(1,3-di(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)-N'-hydroxymethylurea, 1,6-bis(4-amidinophenoxy)-n-hexane and its salts, glutaraldehyde, 5-ethyl-1-aza-3,7-dioxabicyclo(3.3.0)octane, 3-(4-chlorophenoxy)-1,2-propanediol, hyamine, alkyl-(C ８ -C １８ )-dimethyl-benzyl-ammonium chloride, alkyl-(C ８ -C １８ )-dimethyl-benzyl-ammonium bromide, alkyl-(C ８ -C １８ Dimethyl-benzyl-ammonium saccharinate, benzyl hemiformal, 3-iodo-2-propynyl butylcarbamate, sodium hydroxymethylaminoacetate or hydroxymethylaminoacetic acid sodium, imidazolidinyl urea, diazolidinyl urea, sodium hydroxymethylglycinate, DMDM hydantoin, tropolone, (ethylenedioxy)dimethanol, 2-bromo-2-(bromomethyl)pentanedinitrile, N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine, α,α‘,α"-trimethyl-1,3,5-triazine-1,3,5(2H,4H,6H)-triethanol, pyridine-2-thiol-1-oxide, sodium salt, tetrahydro-1,3,4,6-tetrakis(hydroxymethyl)imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 1,3-bis(hydroxymethyl)-1-(1,3,4-tris(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl)urea (diazolidinyl urea), 1,3-bis(hydroxymethyl)-5,5-dimethylimidazolidine-2,4-dione, 3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one, cetylpyridinium chloride, caprylic hydroxamic acid, sorbohydroxamic acid and mixtures thereof; 1,3-propanediol, methylpropanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, 1,2-decanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,2-decanediol, ethylhexylglycerin, hexoxypropane-1,2-diol, heptoxypropane-1,2-diol, octoxypropane-1,2-diol, 3-phenoxypropane-1,2-diol, 3-benzyloxypropane-1,2-diol, 3-phenylethyloxypropane-1,2-diol, 3-phenylpropoxypropane-1,2-diol, 3-methylbenzyloxypropane-1,2-diol, sorbitan caprylate, triclosan, clotrimazole, octopirox (1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone, 2-aminoethanol), chitosan, farnesol, 2-butyl octanoic acid, 2-benzyl heptan-1-ol, glycerol monolaurate, bis(2-pyridylthio)zinc 1,1'-dioxide, N,N'-(decane-1,10-diyl dipyridine-1-yl-4-ylidene)-dioctan-1-amine dihydrochloride (octenidine dihydrochloride), thymol, eugenol, benzyl alcohol, 2-phenylethyl alcohol, 3-phenylpropanol, 2-phenoxyethanol, 1-phenoxypropan-2-ol, 3-phenoxypropanol, benzyloxymethanol, 4-hydroxyacetophenone and mixtures thereof.

11. The compounds that affect solubility are selected from the following group. * Saponins obtained from plant genera Quillaja Yucca Dioscorea, Paris Hosta Agave Asparagus Allium Sapindus Aesculus Hedera Blighia, Dipsacus Aralia and / or Anemone or mixtures thereof * Emulsifiers E400 to 499 or E999 approved as food modifiers in the EU, or mixtures thereof, * Lecithin; polyglycerol esters (PGE), polysorbates, stearoyl lactylate, propylene glycol esters (PGMS), sucrose esters; polyglycerol polyricinoleate (PGPR); ammonium phosphatide (AMP); C ６ - C ２２ Synthetic food-grade emulsifiers selected from the group consisting of mono- and diglycerides of saturated or unsaturated fatty acids, and mixtures thereof.

12. The method according to claim 1, wherein the pH value of the composition is adjusted to from about 1 to about 4 with an inorganic acid or an organic acid.

13. For preserving the composition at a pH of from about 1 to about 4, use of a glycolipid as an antimicrobial agent against at least one of the following microorganisms. - Acacia siamensis - Bacillus licheniformis - Bacillus subtilis - Bisoclamys fulva - Bisoclamys nivea - Candida parapsilosis - Clostridium perfringens - Clostridium sporogenes - Corynebacterium xerosis - Enterococcus faecalis - Lactobacillus paracasei ssp. paracasei - Leuconostoc lactis - Leuconostoc mesenteroides - Malassezia furfur - Neosartorya fischeri - Penicillium paneum - Saccharomyces cerevisiae - Yarrowia lipolytica - Zygosaccharomyces bailii The glycolipid is ussuric acid or a straight-chain C １ -C ４ ester of ussuric acid esterified with an aliphatic alcohol.

14. The use according to claim 13, wherein the at least one usnic acid or its ester is added in an amount effective of about 1 to about 1,000 ppm, calculated with respect to the composition.

15. The use according to claim 13, wherein the composition is a cosmetic, a detergent or a food preparation.

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