US20140178444A1 - Long chain glycolipids useful to avoid perishing or microbial contamination of materials - Google Patents

Long chain glycolipids useful to avoid perishing or microbial contamination of materials Download PDF

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US20140178444A1
US20140178444A1 US14/124,429 US201214124429A US2014178444A1 US 20140178444 A1 US20140178444 A1 US 20140178444A1 US 201214124429 A US201214124429 A US 201214124429A US 2014178444 A1 US2014178444 A1 US 2014178444A1
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compounds
formula
acid
compound
beverages
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Marc Stadler
Jens Bitzer
Bärbel Köpcke
Kathrin REINHARDT
Jana Moldenhauer
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IMD Natural Solutions GmbH
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/30—Microbial fungi; Substances produced thereby or obtained therefrom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B4/00—General methods for preserving meat, sausages, fish or fish products
    • A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
    • A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
    • A23B4/20—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B5/00—Preservation of eggs or egg products
    • A23B5/08—Preserving with chemicals
    • A23B5/12—Preserving with chemicals in the form of liquids or solids
    • A23B5/14—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B7/00—Preservation or chemical ripening of fruit or vegetables
    • A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
    • A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
    • A23B7/154—Organic compounds; Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
    • A23B9/00—Preservation of edible seeds, e.g. cereals
    • A23B9/16—Preserving with chemicals
    • A23B9/24—Preserving with chemicals in the form of liquids or solids
    • A23B9/26—Organic compounds; Microorganisms; Enzymes
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/42—Preservation of non-alcoholic beverages
    • A23L2/44—Preservation of non-alcoholic beverages by adding preservatives
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9728—Fungi, e.g. yeasts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • 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

Definitions

  • the invention relates to the use of, and methods of use employing, certain glycolipid compounds as defined in detail below and having preservative or antimicrobial properties, novel compounds of the glycolipid class, and related invention embodiments.
  • numerous efforts have been made to reduce the deleterious effects of microbial contaminants in food and beverage products, cosmetics, dressing material and other materials, e.g. medical devices such as implants.
  • preservatives such as salt, sugar and vinegar have been used for generations and while relatively safe to use, their preservative effect is limited in both duration of effect and the types of food and beverages for which they can be used.
  • preservatives such as salt and vinegar can affect the taste of the product.
  • preservatives for cosmetics include antimicrobial agents such as quaternary ammonium compounds, alcohols, chlorinated phenols, parabens and paraben salts, imidazolidinyl urea, phenoxyethanol, p-hydroxybenzoate, small carboxylic acids like benzoic acid, sorbic acid, salicylic acid, formic acid, proponic acid or corresponding salts.
  • antimicrobial agents such as quaternary ammonium compounds, alcohols, chlorinated phenols, parabens and paraben salts, imidazolidinyl urea, phenoxyethanol, p-hydroxybenzoate, small carboxylic acids like benzoic acid, sorbic acid, salicylic acid, formic acid, proponic acid or corresponding salts.
  • Formaldehyde-releasers and isothiazolinones may also be used.
  • Another preservative e.g. used in food and especially beverages is sulfuric acid, while in meat products, e.g. sausages, preserved meat and meat, stabilizers which decrease water activity such as potassium and/or sodium nitrites and nitrates are often added. Also smoke is often used for preserving meat products, with the undesirable side effect of formation of polycyclic aromatic hydrocarbons which have carcinogenic properties.
  • Food and beverages have varying degrees of sensitivity to microbiological spoilage depending on intrinsic factors of the food or beverage such as pH, nutrient content (e.g., juice, vitamin, or micronutrient content), carbonation level, Brix (an indicator of sugar content), water quality (e.g., alkalinity and/or hardness), and preservatives.
  • microorganisms are able to overcome the product's intrinsic protection factors and grow.
  • the microorganisms' ability to overcome these hurdles can be influenced by, among other things, initial contamination level, temperature, water content, e.g. water activity, and package integrity. Of special importance are also recurrent contaminations of cosmetics, e.g. by hand contact during normal use.
  • Microbial growth in or on these products depends on several instrinsic factors such as water activity of the formulation (minimum water activity requirements for growth or proliferation range from 0.99 for Acinetobacter species down to 0.61 for some fungal species), formulation composition, pH value (e.g., optimum pH for the growth of most yeasts and molds is between 4.0 and 6.0), and processing conditions such as temperature. While high temperatures, e.g. 80° C. for 20 minutes, may reduce microbial contaminations during processing, it is important to prevent inactivation or degradation of the preservatives in the formulation. Furthermore, product packaging, solubility of the preservative and its antimicrobial susceptibility profile will influence preserving efficacy and, consequently, the shelf life of the products.
  • water activity of the formulation minimum water activity requirements for growth or proliferation range from 0.99 for Acinetobacter species down to 0.61 for some fungal species
  • formulation composition e.g., optimum pH for the growth of most yeasts and molds is between 4.0 and 6.0
  • processing conditions such as temperature
  • this same beverage may be processed using non-preserved techniques such as hot filling, tunnel pasteurization, pasteurization followed by aseptic filling, or requiring the beverage to be chilled, i.e., under refrigeration following the pasteurization step.
  • Beverages having a pH 2-4.6 must be processed such that spores are destroyed using ultra-high temperatures followed by aseptic filling into packages or by using a retort.
  • the preservation properties of weak acids may be enhanced by the addition of preservative enhancers, such as chelating compounds, to the material to be preserved, e.g. a food, beverage or cosmetic preparation.
  • preservative enhancers such as chelating compounds
  • chelating compounds include calcium disodium ethylenediaminetetraacetic acid (EDTA) or one or more of the polyphosphates such as sodium hexametaphosphate (SHMP).
  • weak acids are more likely to exert inhibition if used in conjunction with preservative enhancers.
  • weak acid preservation systems have limitations:
  • low acid beverages i.e., pH 4.6
  • Such low acid beverages should be thermally-treated sufficiently to destroy spores of Clostridium botulinum and Bacillus species ( B. cereus, B. subtilis and others). Examples of such processes include UHT and retort. Even after such processing, the beverage products should be handled in a way to prevent post-processing contamination. Research, however, suggests that there may still be various strains of microorganisms that can survive those different processing techniques. To that end, those processing techniques may not eliminate the potential for spoilage.
  • preservatives can likewise cause adverse side effects when consumed.
  • many existing preservatives must be regulated and have legally imposed upper limits on usage.
  • many preservatives such as sodium benzoate, proprionates, aromatic benzenes, organic acids, propylene glycol and glycerol, for example, when used at levels sufficient for antimicrobial effects, impart an unpleasant taste on the beverage or food, masking or altering to some degree the taste expected by the consumer.
  • Weak acids can impart throat or mouth burn when used at high levels. Although there are certain shelf-stable beverages where this attribute may be acceptable, this sensory perception is often considered negative.
  • polyphosphates used in weak acid preservation systems can have some limitations. For example, polyphosphates can impart off-flavors to a beverage.
  • JP 2006-176438 A and J. Antibiot. 2007, 60, 633-639 disclose F-19848 A, a glyocolipid obtained from the fermentation broth of the fungus strain Dacrymyces sp. SANK 20204, as inhibitor of hyaluronic acid binding receptor CD44 and as being useful for treating or preventing degenerative arthritis or a disease caused by the degenerative arthritis.
  • Biosurfactants are produced extracellularly or as a part of the cellular membrane by various organisms such as bacteria and fungi. Their structures usually contain a hydrophobic non-polar moiety that consists of unsaturated, saturated, and/or oxidized lipids or fatty acids, and a hydrophilic component, which may be composed of amino acids, carbohydrates, phosphates or cyclic peptides. They are generally classified into glycolipids, lipopeptides, phospholipids, fatty acids and polymeric compounds according to their chemical structures. Biosurfactants are produced by a wide range of microorganisms and therefore differ in their chemical structure. Some biosurfactants have antimicrobial activity against bacteria, yeasts, molds or viruses. Moreover, they can prevent microbial colonization of surfaces such as those of implanted medical devices through their ability to disrurpt biofilms on these surfaces.
  • Sophorolipids, rhamnolipids and mannosyl-erythritol lipids are the most widely used glycolipid biosurfactants in cosmetics.
  • Rhamnolipids are known for their efficiency in remove of nosocomial microbes in biofilms.
  • a biofilm is characterized by a strong adherence activity of the engaged microorganisms.
  • biosurfactants with anti-adhesive or biofilm disrupting activity are produced by Lactobacillus acidophilus, L. fermentum, Lactococcus lactis, Streptococcus thermophilus, Bacillus subtilis, B. licheniformis, Brevibacterium aureum, Pseudomonas aeruginosa , and P. putida.
  • preservative does not provide a standard time period for how long the matter to be preserved is kept from spoilage, decomposition, or discoloration.
  • the time period for “preservation” can vary greatly, depending on the subject matter. Without a stated time period, it can be difficult or impossible to infer the time period required for a composition to act as a “preservative”.
  • an extract of Dacryopinax according to the present invention can show a broader activity spectrum than the corresponding single components of the produced glycolipid complex (glycolipid mixture) that have been isolated to purity.
  • Such multi-component mixtures exhibit a remarkable long term activity against numerous important spoilage microbes, including e.g. Zygosaccharomyces and Bacillus species.
  • microorganisms used in the present invention allow producing large amounts of the compounds of formula I in a cost effective production process.
  • microbial contaminants such as bacteria, yeasts, molds and other microorganisms and their spores, especially those which are temperature resistant e.g. thermophilic or heat resistant, or acidophilic e.g. microorganisms which tolerate a lower pH value that cause spoilage of food, beverages, cosmetics and other materials.
  • glycolipids do not exhibit a distinctive taste or unpleasant mouth feeling and therefore this application relates to the use of glycolipids in materials which get in contact with the oral cavity of a human.
  • This application also relates to synergistic combinations of antimicrobial ingredients that can be used in orally consumable compositions, such as food and beverages, without imparting off-flavors.
  • glycolipids of the present invention can be shown to demonstrate a broad antimicrobial spectrum and can be incorporated as additives into various materials as a preservative or an agent with preserving activity, especially as cosmetic additive and/or food additive and/or beverage additive based on this antimicrobial activity.
  • glycolipids Although the mechanism of action for the glycolipids is unknown, these compounds can, without that this is intended to mean a comprehensive and concluding definition of their properties, be considered as biosurfactants and, additionally, might influence the cell membranes of microorganisms.
  • Other known biosurfactants are rhamnolipids, sophorolipids, lipopeptides like chlamydocin, surfactin, lichenysin G, etc. as cited by Mukherjee (in “Biosurfactins”, R Sen ed., Springer, 2010, chapter 4, “Microbial Surfactants and Their Potential Applications”).
  • Mukherjee in “Biosurfactins”, R Sen ed., Springer, 2010, chapter 4, “Microbial Surfactants and Their Potential Applications”.
  • the cited biosurfactants differ from the compounds of formula I of the present invention.
  • Mukherjee listed compounds named as glycolipids the structures of these compounds differ significantly from those of the present invention:
  • the invention relates to the use of a compound of the formula I, or a mixture of two or more such compounds of the formula I,
  • R is a carbohydrate moiety bound via one of its carbon atoms to the binding oxygen, and/or a physiologically, especially pharmaceutically or nutraceutically or cosmetically, acceptable salt thereof, or an ester thereof, as such or in the form of a composition, where the compound may be present in open chain form and/or in the form of a lactone, as agent with preservative or antimicrobial properties, comprising adding the agent to a material, where said material is preferably selected from the group consisting of a cosmetic, a food, a beverage, a pharmaceutical, a medical device, a home care, and an active packaging material.
  • rings A, B and C are monosaccharide moieties each independently from the others with 5 or 6 ring members, wherein one or more of the hydroxyl groups may be acylated.
  • a compound for use according to the invention is especially a linear carboxylic acid with at least 20 carbon atoms, preferably 22 to 28, 24 to 26, in particular 26, substituted at position 2, that means the alpha position, with a hydroxyl group; substituted with a second hydroxyl group at the omega-5, omega-6 or omega-7 position which is itself substituted by a carbohydrate, e.g. as defined below, and one additional (a third) hydroxyl group between the omega and the alpha substituents which is separated from the second one by two to five methylene groups, where optionally this third hydroxyl group has a vicinal hydroxyl group, in the direction of the acidic end.
  • the compound or compounds of the formula I, a physiologically acceptable salt thereof, and/or an ester thereof is added in the form of an extract from a natural source or obtained from such an extract.
  • Dacryopinax spathularia strain MUCL 53181 to be the best strain for identified so far for producing the compounds of formula I and mixtures of two or more compounds of formula I, in particular those described in detail hereinafter, particularly the compounds of formula I exhibiting the strongest antimicrobial activity against yeasts and molds.
  • the present invention also relates to Dacryopinax spathularia strain MUCL 53181 as such.
  • Another embodiment relates to the use as described above or below of one or more compounds of the formula I, where the material to which such compound(s) are applied is subjected to a heat treatment before, during or after addition of the compound(s) of the formula I, a physiologically acceptable salt thereof and/or an ester thereof.
  • the invention relates to a novel compound of the formula I, or a mixture of two or more compounds of the formula I including a novel compound of the formula I, where the compound or compounds may be present in open chain form and/or in the form of a lactone, and/or a pharmaceutically or nutraceutically or cosmetically acceptable salt thereof, as such.
  • Another embodiment of the invention relates to a compound or a mixture of compounds of the formula I shown above or as defined above or below, where the moiety R carries at least one hydroxyl group esterified with an acid with 3 or more carbon atoms, a physiologically acceptable salt, and/or an ester thereof, especially wherein the acid is a C 3 -C 10 -alkanoic acid, especially isovaleric acid; a physiologically acceptable salt, and/or an ester thereof, more especially a compound selected from the group of compounds represented by the following formulae:
  • the present invention relates to a preservative or antimicrobial composition, comprising as active agent a compound or a mixture of compounds of the formula I, a physiologically acceptable salt thereof, and/or an ester thereof, as shown or defined in any one of claims 1 , 3 , 4 and 8 to 15 , alone or with another additive, such as a carrier material, where the preservative composition is especially for use in a cosmetic, a food, a beverage, a pharmaceutical, a medical device, or an active packaging material, especially in the form of a powder or a liquid, e.g. a composition which is a coating or film.
  • the composition in a more specific embodiment of the invention, may be a precursor of a beverage, especially a concentrate, a syrup or a powder.
  • composition defined in the preceding paragraph is an antimicrobial composition for enhancing the stability against microorganisms, especially where at least one microorganism is selected from the group consisting of mold, yeast and bacteria.
  • composition according to any one of the two preceding paragraphs is a preservative or antimicrobial composition for a pharmaceutical, a medical device, a food container, a beverage container, or especially a food, a beverage, a cosmetic, or a home care product.
  • composition according to any one of the two preceding paragraphs is a biofilm inhibiting agent and used as such by administering, or in methods comprising administering, one or more compounds of the formula I, or a composition comprising it, to surfaces or materials coming into contact with surfaces.
  • biofilms on various materials including medical devices, teeth, containers, home care products, pipes or mains or other liquid conducting or containing devices and the like can be avoided.
  • composition according to any one of the preceding four paragraphs comprises an additional preservative.
  • the invention in yet another embodiment, also relates to an extract comprising one or more compounds of the formula I, a physiologically acceptable salt thereof, and/or an ester thereof, as shown or defined above or below.
  • a further invention embodiment relates to a method of enhancing microbial stability of a material, comprising adding to said material one or more compounds of the formula I, a physiologically acceptable salt thereof, and/or an ester thereof, as shown or defined above or below, preferably a material selected from the group consisting of a cosmetic, a food, a beverage, a pharmaceutical, a home care, a medical device, and an active packaging material, especially a beverage, or a food, or a cosmetic.
  • Another embodiment of the invention relates to a material comprising, as or within a coating and/or as admixture, an additive in the form of a compound or a mixture of compounds of the formula I, a physiologically acceptable salt thereof and/or an ester thereof, as defined above or below.
  • This material must be other than the fungus from which the compound or compounds of the formula I are extracted.
  • the material is a cosmetic, a food, a beverage, a pharmaceutical, a home care, a medical device, or an active packaging material, especially a beverage, a beverage precursor, especially a concentrate, syrup or powder, a food or a cosmetic.
  • such material comprises an additional preservative.
  • Another invention embodiment relates to a material according to the preceding paragraph, which is obtained after heat treatment.
  • the invention also relates to a method of extracting and/or isolating one or more compounds of the formula I, especially as described below and/or in the Examples.
  • the invention also relates to the embodiments in the claims and especially the dependent claims which are herewith incorporated by reference into the description.
  • Dacryopinax elegans The currently accepted type species of Dacryopinax is Dacryopinax elegans .
  • Dacryopinax spathularia G. W. Martin. This species was first described from South Carolina, USA, and had been treated under different names (i.e., Merulius spathularius, Guepinia spathularia ) before Martin proposed the genus Dacryopinax .
  • Dacryopinax spathularia is one of the species in the family and order which is capable of producing comparably large basidiocarps. It was reported to be used as “edible mushroom” by the indigenous population of Cameroon (Van Dyck et al., Ambio 32 (2003): 19-23). The entire fungal family Dacrymycetaceae does not contain any poisonous species, even though the basidiocarps of most species are rather inconspicuous and/or have a tough, rubbery consistence that prevents their culinary use. Interestingly, the cultures of certain Dacrymyces species, which can be regarded as closely related to Dacryopinax , have been patented for their utility in production of carotene pigments (U.S. Pat.
  • Carotenoids are also apparently the only secondary metabolites that were so far reported from a species of Dacryopinax , and their production in the cultures of D. spathularia have been studied in detail by Vail & Lilly (Mycologia 60 (1968): 902-907).
  • the fungal strains that produce the compounds of the present invention were characterised by morphological methodology, using phase contrast microscopy of cultures grown on solid YMG medium, and by molecular phylogenetic methods. Since the LSU or 28S/5.8S nuc-rDNA had recently been reported to be informative for the phylogenetic assessments of the Dacrymycetes by Shirouzu et al (Persoonia 23, 16-34, 2009), and the authors of the latter paper published numerous reliable reference sequence data, this region of the DNA was chosen for comparison upon characterisation of the strains of Dacrymycetes that are the subject of the present invention.
  • DNA for PCR was isolated from YMG cultures.
  • the 28S/5.8S nuc-rDNA regions were then amplified using primers LR7 and 5.8SR (Vilgalys Lab, Duke University, Durham, USA, http://www.biology.duke.edu/fungi/mycolab/primers.htm), using the PCR Taq PCR Core Kit (Qiagen, Hilden), and applying a standard thermal profile with an annealing temperature of 53° C.
  • Amplification products were purified using SigmaSpin Post-Reaction Clean-Up columns (Sigma-Aldrich), using the protocol supplied by the manufacturer.
  • Nucleotide sequences were obtained by cycle sequencing using a DNA Cycle Sequencing Kit (Jena Bioscience, Jena, Germany) and 5′ IRD700-labelled primer LROR (Vilgalys Lab). Labelled primers were custom synthesized by Eurofins MWG Operon, Ebersberg, Germany). The cycle sequencing products were then analysed using a LI-COR 4200 (Li-Cor Bioscience, Lincoln, NB) genetic analyser. In the following the characteristics of five strains that were identified of producers of the glycolipids that are subject of the current invention are briefly summarised.
  • Strain FU50088 was isolated from the sporocarp of an unidentified basidiomycete growing on wood in French Guiana by Sergej Buchet in 2002, provided to Bayer Healthcare AG, and selected for fermentation in order to provide extracts that are suitable for natural products screening.
  • YMG agar at 23° C. the culture attained about 10 mm diameter after 10 days of incubation.
  • the mycelium at first appeared velvety and white, but soon attained a strong yellowish color.
  • strain FU50088 was identified to belong to the species Dacryopinax spathularia by morphological, molecular phylogenetic and chemotaxonomic methodology and is referred herein as this species.
  • the reference strain Dacryopinax spathularia CBS 197.63 collected from Bangui, Central African Republic, isolated by J. Boidin and deposited with CBS in April 1963, resembled Dacryopinax spathularia strain FU50088 in its growth and morphological characteristics. However, its pigmentation was not as intense, and even in aged cultures, the mycelia only turned pale yellow. The conidia were subglobose to ovoid, measuring 3-6.5 ( ⁇ 8) ⁇ 2.5-4 ⁇ m.
  • the LSU nucrDNA sequence of this reference strain CBS 197.63 is included here as sequence ⁇ SEQ ID NO: 2>.
  • Ditiola nuda strain CBS 173.60 was isolated in Shirokane, Tokyo, Japan, from a petiole of the plant Shiia sieboldii according to the information provided in the CBS catalogue and deposited with CBS by K. Tubaki in 1960. The strain showed similar growth characteristics to Dacryopinax spathularia FU50088 and like those of the latter strain; its conidia measured 6-5 ⁇ 2.5-3 ⁇ m.
  • the LSU nucrDNA sequence of Ditiola nuda strain CBS 173.60 is included here as sequence ⁇ SEQ ID NO: 3>.
  • Ditiola radicata strain CBS 126.84 was isolated from sporocarps growing on gymnosperm wood collected in August 1982 in Canada, Alberta, Banff National Park, C Level Cirque Trail, by Keith A. Seifert and deposited with CBS in 1984. The strain showed similar growth and morphological characteristics to Dacryopinax spathularia FU50088, but had smaller conidia (4-5 ⁇ 1.5-2 ⁇ m).
  • the LSU nucrDNA sequence of Ditiola radicata strain CBS 126.84 is included here as sequence ⁇ SEQ ID NO: 4>.
  • Ditiola pezizaeformis strain ATCC13299 was originally deposited with ATCC as Femsjonia luteo - alba .
  • the strain had been used in an U.S. Pat. No. 2,974,044 and claimed to be a producer of carotenoids.
  • Femsjonia luteo - alba is a synonym of the valid, internationally accepted name, Ditiola pezizaeformis , as reported by Reid (A monograph of the British Dacrymycetales. Transactions of the British Mycological Society 62 (1974): 433-494) and in accordance with current entries in Mycobank and other taxonomic databases and monographs of Basidiomycetes .
  • the strain ATCC13299 also showed similar growth and morphological characteristics to strain FU50088, and its conidia were elongate-ellipsoid to subglobose, 5-6.5 ⁇ 1.5-2 ⁇ m.
  • the LSU nucrDNA sequence of Ditiola pezizaeformis strain ATCC13299 is included here as sequence ⁇ SEQ ID NO: 5>.
  • Dacryopinax spathularia strain FU50088 has been deposited under the Budapest Treaty at BCCM/MUCL, Myco receptor de l'liable catholique de Louvain, Place Croix du Sud 3, B-1348 Louvain-la-Neuve, Belgium, under the designation number MUCL 53181 on Oct. 11, 2010.
  • the compounds of the invention e.g. compounds of the formula I exhibit a strong, long term inhibitory activity against organisms involved in spoilage of pharmaceutical nutraceutical, nutritional, cosmeceutical, and/or cosmetic preparations or compositions. Said compounds are especially useful against acidophilic spoilage yeasts, which are involved in spoiling or deterioration of beverages. Even more surprisingly these compounds are able to inhibit the growth of thermophilic molds, which are difficult to control with standard sterilizing and/or pasteurizing processes.
  • FIG. 2 Typical HPLC-MS of an extract of FU50088 (MUCL 53181) produced following the example 1B Fermentation c) 200 l fermentation; C Preparation of extracts c) Preparation of a sedimentation product. Adjustment of signals according the “Adapted method” of Example 3. The numbers in brackets “[.]” represent the corresponding compound in Table 1.
  • FIG. 3 Typical HPLC-ELSD chromatogram of an extract of Ditiola pezizaeformis strain ATCC13299 (MUCL 53500), peak annotation according to Table 16 below.
  • FIG. 4 Typical HPLC-MS of an extract [X8] obtained from Dacryopinax spathularia strain FU50088 (MUCL 53181) following example 8D), annotation of signals according the “Improved method” of Example 8C), for details see Table 24A below.
  • the compounds of the formula I are natural compounds, that is, compounds that are present in and can be isolated or extracted from natural sources (especially those mentioned in detail above and below) without chemical synthesis steps (though they may also be prepared or modified by chemical synthesis, e.g. acylated or the like), or be modified by certain downstream processing procedures (e.g. permethylated under influence of acidic methanol) and are thus present as extracts or purified components of extracts, and not derivatives only obtainable by chemical synthesis.
  • natural compounds that is, compounds that are present in and can be isolated or extracted from natural sources (especially those mentioned in detail above and below) without chemical synthesis steps (though they may also be prepared or modified by chemical synthesis, e.g. acylated or the like), or be modified by certain downstream processing procedures (e.g. permethylated under influence of acidic methanol) and are thus present as extracts or purified components of extracts, and not derivatives only obtainable by chemical synthesis.
  • “Substantially” means preferably that the corresponding impurities are present only in trace amounts, e.g. in less than 5% by weight, less than 4% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight or less than 0.2% by weight, in relation to the complete weight of the corresponding dry extract or compound of the formula I or mixture of compounds of the formula I.
  • the terms “essentially consists of” or “essentially consisting of” mean that the total weight share is 90 wt. % or more, preferably 95 wt. % or more, more preferably 98 wt. % or more, most preferably 99 wt. % or more, in each case based on the total amount used.
  • a “mixture essentially consisting of” means that the total amount of the constituents as defined in the respective case is 90 wt. % or more, preferably 95 wt. % or more, more preferably 98 wt. % or more, most preferably 99 wt. % or more, in each case based on the total weight of the mixture
  • glycolipid can be replaced with “glycosylated fatty acid” as well, where it is used with regard to the compounds of the formula I.
  • a compound of the formula I” or “compound(s) of the formula I” can refer to one or more compounds of the formula I, that is one compound or a mixture of compounds of the formula I, or to the USE of a compound of the formula I, where reference to compound(s) of the formula I always includes the compound(s) as such or in the form of a salt (especially a physiologically, that is, e.g., pharmaceutically, nutraceutically or cosmetically) acceptable salt, a solvate and/or a tautomer thereof, or in the lactone form.
  • a salt especially a physiologically, that is, e.g., pharmaceutically, nutraceutically or cosmetically
  • the compounds of the formula I may also be esterified at their free carboxyl group shown in formula I on the right hand side with alcohols, e.g. alcohols with 1 to 10 carbon atoms, such as alkanols, e.g. C 1 -C 7 alkanols, such as methanol or ethanol, phenyl-C 1 -C 4 alkanols, such as benzyl alcohol, or the like.
  • alcohols e.g. alcohols with 1 to 10 carbon atoms
  • alkanols e.g. C 1 -C 7 alkanols, such as methanol or ethanol, phenyl-C 1 -C 4 alkanols, such as benzyl alcohol, or the like.
  • carbohydrate is used in conformity with the IUPAC recommendations (Pure and Applied Chemistry, 1995, 67, 1307).
  • carbohydrate having 3 to 30 (preferably 6 to 18) carbon atoms bound via one of its oxygen atoms” especially refers to mono, oligo- or polysaccharidyl moieties bound via one of their oxygen atoms.
  • the carbohydrates forming the basis for such moieties include, but are not limited to, monosaccharides, disaccharides, further oligosaccharides, or polysaccharides.
  • Disaccharides for example include, but are not limited to, trehalose, sucrose, kojibiose, sophorose, nigerose, laminaribiose, maltose, cellobiose, isomaltose, gentiobiose, lactose, melibiose, neohsperidose, rutinose, primeverose, sambubiose, xylobiose, lathyrose and mannobiose.
  • Oligosaccharides for example include, but are not limited to, raffinose, nystose, panose, cellotriose, maltotriose, maltotetraose, xylobiose, galactotetraose, isopanose, cyclodextrin (alpha-CD) or cyclomaltohexaose, beta-cyclodextrin (beta-CD) or cyclomaltoheptaose and gamma-cyclodextrin (gamma-CD) or cyclomaltooctaose.
  • alpha-CD cyclodextrin
  • beta-CD beta-cyclodextrin
  • gamma-CD gamma-cyclodextrin
  • trisaccharide carbohydrate moieties especially of the formula
  • rings A, B and C are monosaccharide moieties each independently from the others with 5 or 6 ring members, wherein one or more of the hydroxyl groups may be acylated or etherified.
  • the carbohydrate moieties without substitutents resulting from acylation or etherification have 15 to 18 carbon atoms and they are especially selected from the hexapyranosyl-pentapyranosyl-pentapyranosid type such as beta-D-glucopyranosyl-(1 ⁇ 2)-beta-D-xylopyranosyl-(1 ⁇ 2)-beta-D-xylopyranosid or the hexapyranosyl-pentapyranosyl-hexapyranosid type such as beta-D-glucopyranosyl-(1 ⁇ 2)-beta-D-xylopyranosyl-(1 ⁇ 2)-beta-D-glucopyranosid.
  • the hexapyranosyl-pentapyranosyl-pentapyranosid type such as beta-D-glucopyranosyl-(1 ⁇ 2)-
  • the carbohydrates may carry one, more or all hydroxyl groups in modified form, e.g. as etherified hydroxyl or especially esterified hydroxyl as defined below, respectively, for example in a form acylated by a C 2 -C 10 -alkanoic acid, e.g. acetylated, e.g. mono- or di or tri- or tetra-acetylated, form.
  • a particularly preferred modified form is represented by those compounds of the formula I which have one or more hydroxyl groups in the carbohydrate moiety that is or are acylated by an isovaleryl (3-methyl-butanoyl) moiety—these compounds are novel and thus also as such form an invention embodiment.
  • Individual compounds of formula I with an acyl substituent with more than 2 carbon atoms, such as (and preferably) an isovaleryl substituent (and preferably one single isovaleryl substituent), in the carbohydrate moiety R typically exhibit a stronger antimicrobial activity, particularly against yeasts and molds, especially against yeasts and molds of relevance regarding food, beverage and/or cosmetic spoilage, and/or a broader activity spectrum than the corresponding compounds with an acetyl substituent in the carbohydrate moiety R.
  • esters may be acetates; propionates; butyrates; isobyturates; valerates such as n-pentanoate) or 2-methyl butyrate, or the unsaturated derivatives such as but not limited to 2-methyl-2-butenoate (e.g.
  • angeloate or tiglate 3-methyl-2-butenoate or 3-methyl-3-butenoate (senecioate), or hydroxylated derivatives such as 2-methyl-3-hydroxy butyrate or 2-hydroxymethyl butyrate; or hexenoates such as n-hexanoate (caproate), isohexanoates such as but not limited to 2-methylvalerate, 3-methylvalerate, 4-methylvalerate, 2,3-dimethyl butyrate, or the unsaturated derivatives e.g. 2-ethyl-2-butyrate, 2-methyl-2-pentenoate, 4-methyl-2-pentenoate; or aminoacyl, e.g.
  • acylated forms may preferably be natural products, but they can also be products of chemical or enzymatic acylation, e.g. using active forms of the acids and, where required to avoid reaction of other functional groups, introduction and, especially to obtain the final product, removal of protecting groups (“Pg”).
  • the chemical acylation can take place with the corresponding acid as such or preferably in the form of a reactive derivative.
  • Reactive (or active) derivatives used as such include the halogenides, e.g. chlorides, or nitrophenyl esters, e.g. the 2,4-dinitrophenyl esters, or acid anhydrides (symmetric or e.g. with acetic acid) of the carboxy groups of the acids to be reacted.
  • Triazoles uronium or hexafluorophosphonium derivatives, e.g. 1-hydroxy-benzotriazole (HOBt), Carbodiimides, e.g. dicyclohexylcarbodiimide, active ester forming agents, e.g. 2-mercaptobenzothiazole (2-MBT), azide forming agents, e.g. diphenyl phosphoryl azide, acid anhydrides, such as propane phosphonic acid anhydride, acid halogenation agents, e.g. 1-chloro-N,N,2-trimethyl-1-propenylamine, or the like, or mixtures of two or more such agents.
  • HOBt 1-hydroxy-benzotriazole
  • Carbodiimides e.g. dicyclohexylcarbodiimide
  • active ester forming agents e.g. 2-mercaptobenzothiazole (2-MBT)
  • azide forming agents e.g. diphenyl phospho
  • the compounds of the formula I are preferably obtained by extraction in the form of extracts from natural sources or in further enriched or purified from such extracts (see below), they can also be obtained by chemical synthesis methods.
  • the compounds may be synthesized chemically e.g. by a convergent strategies.
  • the glycoside part and the unbranched long-chain ⁇ -hydroxy carboxylic acid part of the molecules are build up separately, with the hydroxyl groups and the carboxylic acid moieties being protected by suitable protecting groups. Afterwards, both building blocks are connected via building a glycosidic linkage using methods described in the scientific literature. Finally, removal of the protecting groups will lead to the desired compounds.
  • the present glycolipid compounds of the formula I comprise all stereoisomers, such as those which may exist due to asymmetric carbons on the various substituents, including enantiomeric forms and diastereomeric forms.
  • Individual stereoisomers of the glycolipid derivatives of the present invention may, for example, be substantially free of other isomers, or may be admixed, for example, as racemates or with all other, more than one other, or two to less than all other selected stereoisomers, e.g. diastereomers.
  • vicinal dihydroxy group in the fatty acid part is in one embodiment of the invention to be understood as syn and/or anti configurated.
  • the final carboxyl group of the carboxylic acid chain may also form a lactone with one of the hydroxyl groups present on the rest of a molecule of the formula I
  • compounds of the formula I may also be present in the lactone form, either purely or in admixture with the open chain form.
  • the salts of compound(s) of the formula I are especially physiologically acceptable salts, that is, salts that have no disturbing toxical, allergenic and/or mutagenic properties on human or animal cells.
  • physiologically acceptable salts that is, salts that have no disturbing toxical, allergenic and/or mutagenic properties on human or animal cells.
  • Such salts can be selected from those known in the art, e.g. using calcium, sodium, magnesium, or ammonium as counterions of the carboxylic group or the salts mentioned below.
  • salt-forming groups e.g. acidic groups, such as carboxylic acid groups, or basic groups, such as amino or imino groups
  • the glycolipid compounds of the formula I may be in the free form or in the form of salts.
  • salt(s) denotes acidic and/or basic salts formed with inorganic and/or organic acids and bases.
  • inner salts may be formed and are included within the term “salt(s)” as used herein.
  • Salts of compounds of the formula I may be formed, for example, by reacting a compound of the formula I with an amount of acid or base, such as an equivalent amount, in a medium such as one in which the salt precipitates or in an aqueous medium followed by lyophilisation or followed by the addition of a water miscible organic solvent.
  • ion exchangers can be used to form salts from free forms or free forms from salts of a compound of the formula I.
  • Free form refers to “form without salt-forming counterions”, e.g. in non-salt form.
  • the compounds of the formula I which contain an acidic moiety may form salts with a variety of organic and inorganic bases.
  • exemplary basic salts include ammonium salts, non-toxic metal salts derived from metals of groups Ia, Ib, IIa and IIb of the Periodic Table of Elements, e.g.
  • alkali metal salts such as sodium, lithium, or potassium salts
  • alkaline earth metal salts such as calcium or magnesium salts
  • salts with other metals such as zinc
  • salts with organic bases for example, organic amines
  • organic bases for example, organic amines
  • t-butyl amine N-methyl-N-ethylamine, diethylamine, triethylamine, mono-, bis- or tris-(2-hydroxy-lower alkyl)amines, such as mono-, bis- or tris-(2-hydroxyethyl)amine, 2-hydroxy-tert-butylamine or tris(hydroxymethyl)methylamine, N,N-di-lower alkyl-N-(hydroxy-lower alkyl)-amines, such as N,N-dimethyl-N-(2-hydroxyethyl)-amine or tri-(2-hydroxyethyl)-amine, or N-methyl-D-glucamine; or cyclic amines such as piperidine, N-lower alkyl piperidine e.g.
  • N-methyl-piperidine, piperazine, or quaternary ammonium salts formed via common processes out of the above define amines, such as tetrabutylammonium salts, or with benzathines, dicyclohexylamines, N-methyl-D-glucamines, N-methyl-D-glucamides, purines, caffeine, theobromine, hydrabamine, choline, betaine, or salts with amino acids such as arginine, lysine, histidine and the like. Also salts with salt-forming pharmaceutical and/or nutraceutical carrier materials are possible and encompassed by the invention.
  • the desired substances of the formula I are isolated from natural sources, either with subsequent chemical modification (e.g. acylation) or preferably without such chemical modification.
  • Desired substances in the present context are any substances that directly or indirectly contribute to the preservative properties of the composition, with the proviso that one or more compounds of the formula I are also included.
  • the isolation can be performed by isolating or separating the one or more compounds of the formula I according to chemical and/or physical properties. Examples of chemical properties include affinity for one or more compounds and chemical stability. Examples of physical properties include mass or size, charge, solubility, polarity, distribution, absorption to surfaces, melting point, and the like.
  • Natural compounds of the formula I, or extracts comprising one or more thereof, for USE in or according to the present invention are isolated from one or more cultures, especially liquid cultures, of mushrooms of the genera listed above or below, e.g. with the genetic characteristics provided in detail below.
  • extract either a direct extract (in liquid or preferably dried form), e.g. obtained as described below, or preferably a further enriched extract (obtainable e.g. by one or more further purification steps after extraction, e.g. chromatography, for example as described below) containing one or more, preferably two or more compounds of the formula I is meant.
  • the compound(s) of the formula I in the form of an extract and extracts according to the invention can be obtained especially preferably by extraction of liquid cultures, especially liquid or solid mycelial cultures, of mushrooms of the genus Dacryopinax , e.g. mushrooms or parts thereof of the species Dacryopinax , mushrooms of the genus Ditiola , e.g. mushrooms or parts thereof, and/or mushrooms of the genus Femsjonia luteo - alba , e.g. mushrooms or parts thereof, especially the species and more especially the deposited strains as defined above.
  • Extracts according to the invention or useful according to the invention may be manufactured according to any suitable process, preferably comprising extraction of one or more compounds of the formula I.
  • extract wherever used also includes precipitates, e.g. manufactured as described below.
  • Extraction thus may take place with a non polar or weakly polar (meaning less polar than water) solvent or solvent mixture, meaning that the preferred obtainable or obtained extracts according to the invention are lipophilic extracts.
  • the polarity is defined by an E T (30) value of 56 kcal/mol or lower (at 25° C. and 1 bar), e.g. of 52 kcal/mol or lower (water has an E T (30) of 63.1).
  • the E T (30) method is based on a method published by Reichart et al. and makes use of the stabilisation of the ground state of the betaine dye 2,6-diphenyl-4-(2,4,6-triphenyl-1-pyridinio)phenolate, CAS No 10081-39-7, in apolar solvents leading to a higher energy for the transition from the ground state (HOMO) to the first excited state (LUMO) of the molecule (see K. Dimroth, J Lieb Ann d Chemie (1963) 661(1): 1-37, DOI 10.1002/jlac.19636610102).
  • the extract may be obtained by bringing a culture supernatant to a slightly alkaline pH, e.g. by adding an alkalimetal hydroxide, such as sodium or potassium hydroxide, separating of any solid material, e.g. the mycelia or other solid components, e.g. by microfiltration, acidifying the filtrate by addition of an acid, e.g. an organic or inorganic acid, such as a hydrohalogenide, such as hydrochloride, to an appropriate pH, e.g. lower than the pKa (which may, for compounds of the formula I, be assumed to lie in the range of about 4.0 to 5.0, e.g.
  • an alkalimetal hydroxide such as sodium or potassium hydroxide
  • the addition according to the use or method of the invention preferably takes place by mixing the resulting extract or isolated compound(s) of the formula I into such a material or by impregnating or coating it with the compound(s) of the formula as such or in an appropriate (e.g. liquid) composition.
  • drying e.g. freeze-drying, spray-drying, fluid bed or spouted bed or evaporation
  • granulation e.g. to syrups, formed via concentration and/or with the aid of thickeners
  • concentrating e.g. to syrups, formed via concentration and/or with the aid of thickeners
  • pasteurizing sterilizing, freezing, dissolving, dispersing, filtering, centrifuging, confectioning, and the like.
  • the compounds of the formula I have surprisingly been found to show especially preservative or antimicrobial purposes (the term “antimicrobial” especially referring to treated materials which are not treated to avoid perishing of themselves but are to be used in a form not contaminated by microbes, e.g. implants or the like, while the term “preservative activity” also includes antimicrobial activity, but also other stabilizing activity, e.g. by emulsification or acidification due to addition of the compound(s) of the formula Ito perishable goods).
  • the term “enhance the stability against microorganisms” refers to inhibiting the growth or killing microorganisms, thus providing a material equipped according to the invention with one or more compounds of the formula I with protection against microbial damage, films or degradation.
  • liquids for human or animal consumption those can be mentioned which are labelled as juice, drink (including soft drink, such as lemonade), non-alcoholic or alcoholic beverage, and/or cocktail.
  • the use as an agent with preservative properties of a compound or compounds of the formula I includes also the use in precursor products of beverages, e.g. concentrates, syrups and/or powders will reconstitute to a beverage in the sense of the invention by the addition of water.
  • infant formula means a food which purports to be or is represented for special dietary use solely as a food for infants by reason of its simulation of human milk or its suitability as a complete or partial substitute for human milk.
  • Beverages can be alcoholic and/or non alcoholic, carbonated and/or non carbonated
  • Beverages include non-dairy milks, and the like.
  • Beverages may include water, flavoured water, fortified waters, flavoured beverages, carbonated water, e.g. flavoured seltzer or soda waters, juices, cola, lemon-lime, ginger ale, and root beer beverages which are carbonated in the manner of soft drinks, as well as beverages that provide health or wellness benefits from the presence of metabolically active substances, such as vitamins, amino acids, proteins, carbohydrates, lipids, or polymers thereof, where such products may also be formulated to contain milk, coffee, or tea (e.g. green tea) or other botanical solids, syrup, diet beverages, carbonated soft drinks, fruit juices, e.g.
  • nutritionalally active substances such as vitamins, amino acids, proteins, carbohydrates, lipids, or polymers thereof, where such products may also be formulated to contain milk, coffee, or tea (e.g. green tea) or other botanical solids, syrup, diet beverages, carbonated soft drinks, fruit juices, e.g.
  • fruit drinks which provide the flavor of any of the e.g. aforementioned fruit juices and contain greater than 0% fruit juice but less than 100% fruit juice, fruit flavored beverages, vegetable juices, e.g. tomato juice, beet juice, carrot juice, celery juice, vegetable containing beverages, which provide the flavor of any of the aforementioned vegetable juices and contain greater than 0% vegetable juice but less than 100% vegetable juice, isotonic beverages, non-isotonic beverages, soft drinks containing a fruit juice, coffee, tea, tea beverages prepared from tea concentrate. extracts, or powders, drinkable dairy products, e.g.
  • drinkable yogurts (drink yoghurt), kefir or buttermilk, hot chocolate, chocolate powders/mixes, drinkable soy products, non-diary milks, e.g. coconut milk, alcoholic beverages, e.g. malt beverages, wine, beer, distilled liquors, spirits, sparkling wine, champagne or liqueurs, fruit smoothies, horchata (vegetable and/or rice components made into a beverage), sport drinks, energy drinks, health drinks, shakes, protein drinks (e.g. dairy, soy, rice or other), drinkable soy yogurts, low acid beverages as defined in US 21 C.F.R. Part 113. Acidified beverages as defined in US 21 C.F.R. Part 114, nectars, tonics, frozen carbonated beverages, frozen uncarbonated beverages, liquid meal replacements, infant formulations, and combinations or mixtures thereof.
  • non-diary milks e.g. coconut milk
  • alcoholic beverages e.g. malt beverages, wine, beer, distilled liquors,
  • nutraceutical is a substance that has been shown to possess, minimally, either a general or specific health benefit or sense of wellness as documented in professional journals or texts. Nutraceuticals, however, do not necessarily act to either cure or prevent specific types of medical conditions.
  • the foods or beverages may comprise further customary additives for food and/or beverages.
  • additives in the sense of “sweeteners” are substances used to impart a sweet taste to foods (this term in the present paragraph also including beverages) or in table-top sweeteners; “antioxidants” are substances that hinder the oxidation of components, e.g. avoiding that the material becomes rancid; “colors” are substances which add or restore color in a food, and include natural constituents of foods and natural sources which are normally not consumed as foods as such and not normally used as characteristic ingredients of food.
  • Preparations obtained from foods and other edible natural source materials obtained by physical and/or chemical extraction resulting in a selective extraction of the pigments relative to the nutritive or aromatic constituents are colors within the meaning of this Regulation; “preservatives” are substances which prolong the shelf-life of foods by protecting them against deterioration caused by micro-organisms and/or which protect against growth of pathogenic micro-organisms; “antioxidants” are substances which prolong the shelf-life of foods by protecting them against deterioration caused by oxidation, such as fat rancidity and color changes; “carriers” are substances used to dissolve, dilute, disperse or otherwise physically modify a food additive or a flavouring, food enzyme, nutrient and/or other substance added for nutritional or physiological purposes to a food without altering its function (and without exerting any technological effect themselves) in order to facilitate its handling, application or use; “acids” are substances which increase the acidity of a foodstuff and/or impart a sour taste to it; “acidity regulators”
  • preservatives for food and beverages also named additional (chemical) preservatives herein
  • benzoic acid benzoic acid sodium salt, benzoic acid potassium salt, benzoic acid calcium salt, propionic acid, salicylic acid, sorbic acid, sorbic acid sodium salt, sorbic acid potassium salt, sorbic acid calcium salt, ethyl para-hydroxybenzoate, sodium ethyl para-hydroxybenzoate, propyl para-hydroxybenzoate, sodium propyl para-hydroxybenzoate, methyl para-hydroxybenzoate, sodium methyl para-hydroxybenzoate, sulphur dioxide, sodium sulphite, sodium hydrogen sulphite, sodium metabisulphite, potassium metabisulphite, calcium sulphite, calcium hydrogen sulphite, biphenyl or diphenyl, orthophenyl phenol, sodium orthophenyl phenol, thiabendazole, nisin, natamycin or
  • the consumables of the present invention may have a pH ranging from 1.5 to 10, e.g. from about 1.5 to about 4.6 It is known in the art that the pH of a beverage may be a factor in maintaining a shelf-stable beverage, as the growth of some microorganisms may be hindered under acidic conditions. This, however, is not the case for acidophilic microorganisms such as Lactobacillus, Saccharomyces and Candida which thrive in such an acidic environment. Utilizing the present invention allows the composition to maintain microbial stability even in view of these acidophilic microorganisms.
  • the acidity of the beverage can be adjusted to and maintained within the recited range by known and conventional methods in the art.
  • the pH can be adjusted using one or more acidulant(s), also named acidity regulator(s), e.g. as defined below.
  • the amounts of the acidity regulator(s), which may be present in the composition according to the present disclosure are those conventionally used in beverage compositions.
  • at least one acidulant may be present in an amount ranging from about 0.01% to about 1% by weight relative to the composition.
  • An aspect of the invention is directed to preserving a broad range of beverage products that possess a pH of less than 7.5, in particular less than about 4.6, such as 2.5 to 4.6 against spoilage by yeast, mold and a range of acid tolerant bacteria.
  • Preservation of product can be accomplished merely through the addition of the chemical agents described herein, but it is also possible to supplement the action of the chemicals with purely physical forms of preservation such as alteration of product temperature, various wavelengths of irradiation, pressure or combinations thereof.
  • the pH of the beverage product comprising the preservative system is e.g., about 4.6 or less, about 2.5 to about 4.4, about 2.6 to about 4.5.
  • the acidity regulator(s) may be in an undissociated form or in their respective salt form such as potassium, sodium, or hydrochloride salts, or be a mixture, thus forming a kind of buffer for an intended pH.
  • acidity regulators pH regulators
  • organic and inorganic acids to be used in adjusting the pH of a composition of the present invention such as a beverage may be mentioned, e.g. acetic acid, sodium acetates, e.g. sodium hydrogen acetate, potassium acetate, calcium acetate, ascorbic acid, sodium ascorbate, potassium ascorbate, carbon dioxide, sodium carbonates incl.
  • sodium hydrogen carbonate (bicarbonate of soda) and sodium sesquicarbonate, potassium carbonates e.g.
  • the compounds of the formula I due to their acid/base properties, can also be used to regulate the pH of a composition comprising them.
  • lecithins metatartaric acid, calcium tartrate; alginic acid and the sodium, potassium, ammonium and calcium salts, propane-1,2-diol alginate; agar; Carrageenan; processed Vietnameseeuma seaweed; locust bean gum; carob gum; guar gum; tragacanth; acacia gum; gum arabic; xanthan gum; Karaya gum; Tara gum; Gellan gum; glycerol; Konjac, konjac gum, konjac glucomannane; soybean emicellulose; Cassia gum; polyoxyethylene (8) stearate; polyoxyethylene sorbitan monolaurate, polysorbate 20; polyoxyethylene sorbitan monooleate, polysorbate 80; polyoxyethylene sorbitan monopalmitate, polysorbate 40; polyoxyethylene sorbitan monostearate, polysorbate 60; polyoxyethylene sorbitan tristearate, polysorbate 65; pectins and amidated pect
  • Such additives may be present in relative amounts, considering the complete composition of the food or beverage product concerned, in amounts summing up to from 0.01% up to 90% by weight, e.g. from 0.05% to 50% by weight, e.g. from 0.1% to 5% by weight or from 0.2% to 20% by weight.
  • the compounds of the formula I in view of their preservative properties, are also useful in supporting or providing preservation of cosmetics.
  • an article e.g. a mixture or substance or product, intended to be placed in contact with the various external parts of the human body or animal body (epidermis, hair system, nails, lips and external genital organs), e.g. which can be rubbed, poured, sprinkled, or sprayed on, or otherwise applied to the human body or any part thereof, including the oral cavity and the teeth, skin and hair, with a view exclusively or mainly to cleaning them, perfuming them, changing their appearance and/or correcting body odors, and/or protecting them or keeping them in good condition.; and (2) articles intended for use as a component of any such articles; explicitly including soap.
  • cosmetics as used here also includes “personal care products” and “personal hygiene products”, such as menstrual care products, handkerchief tissues and the like.
  • cosmetic products include but are not limited to:
  • gargles, mouthwash or toothpastes products for nail care and make-up; products for external intimate hygiene; sunbathing products; products for tanning without sun; skin-whitening products; anti-wrinkle products, tampons, sanitary towels, wet wipes, diapers or handkerchiefs.
  • certain above mentioned cosmetic products may also be used in the medical filed, in particular certain washing products are suitable as disinfecting products, such as hand disinfecting products or instrument disinfecting products.
  • the antimicrobial properties of the compounds of the formula I may provide, as additional benefit in the sense of a bonus effect, their antimicrobial efficiency to the cosmetic properties of the formulations, although the purely cosmetic use of the corresponding cosmetics is preferably predominant.
  • the cosmetics may comprise, in relationship to their intended use, various active and inactive ingredients, named “cosmetic additives” in the following.
  • hair or nails e.g. dyes or pigments, e.g. lactoflavin, caramel capsanthin, capsorubin, beetroot red, anthocyanins, bromothymol blue, bromocresol green, acid red, aluminium, magnesium, calcium and zinc stearates
  • denaturants are substances which render cosmetics unpalatable, mostly added to cosmetics containing ethyl alcohol
  • deodorants are substances which reduce or mask unpleasant body odors
  • depilatories are substances which remove unwanted body hair
  • detanglings are substances which reduce or eliminate hair intertwining due to hair surface alteration or damage and, thus, helps combing
  • emollients are substances which soften and smooth the skin
  • emulsifiers are substances which promote the formation of intimate mixtures of non-miscible liquids by altering the interfacial tension
  • emulsion stabilizers are substances which help the process of emulsification and improves emulsion stability
  • oxidizers are substances which change the chemical nature of another substance by adding oxygen or removing hydrogen
  • pearlescents are substances which impart a nacreous appearance to cosmetics
  • plasticizers are substances which soften and make supple another substance that otherwise could not be easily deformed, spread or worked out
  • preservatives are substances which inhibit primarily the development of micro-organisms in cosmetics
  • propellants are substances which generate pressure in an aerosol pack, expelling contents when the valve is opened, some liquefied propellants can act as solvents
  • propellants are substances which change the chemical nature of another substance by adding hydrogen or removing oxygen
  • refatters are substances which replenish the lipids of the hair or of the top layers of the skin
  • refreshers are substances which impart a pleasant freshness to the skin
  • skin conditioners are substances which maintain the skin in good condition
  • skin protectors are substances which help to avoid harmful effects
  • citric acid, malic acid, L-, D- or DL-lactic acid skin colorants
  • skin colorants e.g. walnut extracts or dihydroxyacetone
  • active ingredients for promoting hair growth e.g. minoxidil, diphencyprone, hormones, caffeine, finasteride, phytosterols such as beta-sitosterol, biotin, or extracts of Cimicifuga racemosa, Eugenia caryophyllata or Hibiscus rosa - sinensis , barley, hops, or rice or wheat hydrolysates
  • skin care products e.g. cholesterol, ceramides, pseudoceramides
  • softening moisturizing and/or moisture-retaining substances
  • preservatives for cosmetic preparations, the following may be mentioned: benzoic acid, formic acid and their sodium salt; propionic acid, salicylic acid, sorbic acid, other weak acids, e.g. free fatty acids, esters and derivatives thereof, undec-10-enoic acid and their salts; formaldehyde incl.
  • the invention also comprises cosmetics, especially their use, comprising beyond one or more of the compounds of the formula I also “other natural antimicrobially active agents”, e.g. proteins, corresponding peptides alone or in combination, natural essential oils or derivatives thereof, such as oil from anis, lemon, orange, grapefruit, rosemary, thyme, lavender, tee tree, citron, wheat, lemon grass, cedar, cinnamon, eucalyptus, peppermint, basil, fennel, menthol, Ocmea origanum, Hydastis carradensis, Krameria lappacea, Podophyllum spp., Curcuma longa , or mixtures of two or more such oils.
  • other natural antimicrobially active agents e.g. proteins, corresponding peptides alone or in combination, natural essential oils or derivatives thereof, such as oil from anis, lemon, orange, grapefruit, rosemary, thyme, lavender, tee tree, citron, wheat, lemon
  • Botanicals such as camphor and cinnamon may also be used.
  • Individual constituents (“ICs”) of essential oils may be natural or entirely or partially synthetic, and include, but are not limited to, l-citronellol, alpha-amylcinnamaldehyde, lyral, geraniol, famesol, hydroxycitronellal, isoeugenol, eugenol, eucalyptol, linalool, citral, thymol, limonene and menthol.
  • sesquiterpenoids such as nerolidol, farnesol, bisabolol and apritone may also be used in the present invention.
  • Mixtures of one or more EO, one or more IC, and one or more EO as well as one or more IC are encompassed by the present invention.
  • UV filters include but are not limited to: phenylen-1,4-bis-(2-benzimidazyl)-3,3′-5,5′-tetrasulfonic acids; 2-phenylbenzimidazol-5-sulfonic acid and corresponding salts; 1,4-di(2-oxo-10-sulfo-3-bornylidenmethyl)-benzene and corresponding salts; 4-(2-oxo-3-bornylidenmethyl)benzenesulfonic acid and its salts; 2-methyl-5-(2-oxo-3-bornylidenmethyl)sulfonic acid and its salts; 2,2′-methylen-bis-(6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)-phenol); 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxany
  • the cosmetics may be solid, e.g. of a waxy appearance or the like, or liquid or in the form of pastes or creams, e.g. as emulsions, solutions or suspensions, e.g. oil in water or water in oil (O/W or W/O) mixtures. They can thus form e.g. a solution, an emulsion of the water-in-oil (W/O) type or oil-in-water (O/W) type, or a multiple emulsion, for example of the water-in-oil-in-water (W/O/W) type, a gel, a hydrodispersion, a solid stick or else an aerosol.
  • emulsions e.g. oil in water or water in oil (O/W or W/O) mixtures.
  • They can thus form e.g. a solution, an emulsion of the water-in-oil (W/O) type or oil-in-water (O/W) type, or
  • the possible surfactants include but are not limited to customary ones, e.g. anionic, non-ionic, amphoteric tensides, such as soaps or sodium dodecylsulfate, or the substances disclosed in WO 2011/023582.
  • the compounds of the formula I can also contribute surfactant properties to a composition according to the invention, so that this use is a preferred embodiment of the invention.
  • composition comprising one or more compounds of the formula I according to the invention can be applied to the skin or lips or other body surfaces, e.g. hair, nails or teeth, according to the use for which it is intended. It can thus be used in a method for the cosmetic treatment of said body surfaces, e.g. the skin, comprising the application of the composition according to the invention to said body surface, e.g. the skin, for example for the purpose of toning it up, of regenerating it or of smoothing out its e.g. wrinkles in skin and/or for combating ageing, e.g. of the skin, or the damaging effects of UV radiation and/or for strengthening skin tissues, teeth, hair and/or nails against attacks from the surroundings.
  • composition according to the invention can be used for the manufacture of a dermatological preparation.
  • laundry detergents dishwashing detergents, fabric softeners, hard surface cleaner or bleach compositions
  • surface, laundry and/or dish cleaners laundry soaps, air fresheners and odor eliminators, insect repellents, laundry detergents, fabric softeners, bleaching agents, organic cleaners, degreasers, stain removers, window and glass cleaners, bathroom and toilet bowl cleaners, floor cleaners, carpet cleaners, pet odor removers, cat litter deodorizers, car refresheners, furniture polishes, waterless hand cleaners, disinfectants, spray deodorizers, food processing plant cleaners, coloring matters or other like home care applications may be mentioned.
  • the home care products have customary compositions, For example, in addition to surfactants, conventional solvents, dyes, preservatives, emulsifying agents, perfumes, antibacterial agents, thickeners, conditioners, antistatic agents, silicone surfactants, and other like ingredients that are typically present in conventional home care formulations may be comprised. Mixtures and/or combinations of the aforementioned additional formulating agents may also be employed in the present invention. The amounts of the additional formulating agents that may be employed in the present invention are within ranges that are well known to those skilled in the art and further formulating is performed using processes that are also well known in the art.
  • Pharmaceuticals comprise one or more pharmaceutically active agents and a pharmaceutically acceptable carrier material.
  • compositions examples include solid (tablet, capsule, powder, medical chewing gum, lozenge, suppository) or liquid formulations (e.g. injection solution, infusion solution, syrup, drinkable solution), a spray, or a pasty material, e.g. a gel or a cream.
  • bronchodilators antipyretics, analgetics, antiphlogistics, antiarrhythmics, blood-pressure reducing agents, vasodilators, anticholinergics, antiarteriosclerotics, enzymes, antibodies, secretolytics, ulcer preparations, antiproliferative agents, vasoconstrictors, expectorants, antitussiva, mucolytics, or secretomotorics; in particular, free of antiallergics (including those referred to hereinbefore), such as ⁇ -sympathicometics (in particular Phenylephrin, Ephedrin, Tetryzolin, Naphazolin, Oxymetozolin, Xylometazolin or Tramazolin), antihistamines, non-steroidal or steroidal anti-inflammatory active substances (in particular Triamcinolone acet
  • benzodiazepines including mitochondrial benzodiazepine-ligands MAO inhibitors, SSRI's, SNRI's, NK receptor antagonists, CRF-receptor antagonists, 5HT7 receptor-antagonists, mGlu receptor agonists/antagonist/modulators, GABA-A or GABA-A/B receptor agonist/antagonists or modulators, vasopressin receptor antagonists, herbal medicine such as St. John's Wort, 5-HT1A receptor agonists, vasopressin receptor-antagonists, acetylcholine-esterase inhibitors, such as rivastigmine or donepezil, mixed acetylcholine/butyrylcholine esterase-inhibitors.
  • nicotinic-alpha7-receptor agonists typical or atypical antipsychotics, such as clozapine or haloperidol, nicotinic-alpha7-receptor agonists, antimanic agents (e.g. lithium, Carbamazepine, Valproate) or any atypical or typical antipsychotic; or the like; pharmaceutically acceptable salts thereof, if salt-forming groups are present; or combinations of two or more of the aforementioned active substances or their pharmaceutically acceptable salts.
  • antimanic agents e.g. lithium, Carbamazepine, Valproate
  • compositions comprising one or more active ingredients and one or more compounds of the formula I in association with at least one pharmaceutical acceptable carrier or diluent may be manufactured in conventional manner by mixing with a pharmaceutically acceptable carrier or diluent.
  • the invention relates also to pharmaceutical compositions comprising an antimicrobially effective amount, especially an amount effective in the treatment of one of the above-mentioned disorders, of one or more compounds of the formula I, a pharmaceutically acceptable salt thereof, and/or an ester thereof, together with one or more pharmaceutically acceptable carriers that are suitable for topical, enteral, for example oral or rectal, or parenteral administration and that may be inorganic or organic, solid or liquid.
  • pharmaceutically acceptable carriers that are suitable for topical, enteral, for example oral or rectal, or parenteral administration and that may be inorganic or organic, solid or liquid.
  • diluents for example lactose, dextrose, mannitol, and/or glycerol, and/or lubricants and/or polyethylene glycol.
  • Tablets may also comprise binders, for example magnesium aluminum silicate, starches, such as corn, wheat or rice starch, gelatin, methylcellulose, sodium carboxymethylcellulose and/or polyvinylpyrrolidone, and, if desired, disintegrators, for example starches, agar, alginic acid or a salt thereof, such as sodium alginate, and/or effervescent mixtures, or adsorbents, dyes, flavorings and sweeteners. It is also possible to use the pharmacologically active compounds of the present invention in the form of parenterally administrable compositions or in the form of infusion solutions.
  • binders for example magnesium aluminum silicate, starches, such as corn, wheat or rice starch, gelatin, methylcellulose, sodium carboxymethylcellulose and/or polyvinylpyrrolidone
  • disintegrators for example starches, agar, alginic acid or a salt thereof, such as sodium alginate, and/or effervescent mixtures, or
  • compositions may be sterilized and/or may comprise excipients, for example preservatives, stabilizers, wetting compounds and/or emulsifiers, solubilizers, salts for regulating the osmotic pressure and/or buffers.
  • excipients for example preservatives, stabilizers, wetting compounds and/or emulsifiers, solubilizers, salts for regulating the osmotic pressure and/or buffers.
  • compositions which may, if desired, comprise other pharmacologically active substances are prepared in a manner known per se, for example by means of conventional mixing, granulating, confectioning, dissolving or lyophilizing processes, and comprise approximately from 1% to 99% by weight, especially from approximately 1% to approximately 60%, active ingredient(s) and 0.001 to 10, 0.01 to 8, 0.02 to 6 or 0.03 to 5 weight percent of the compound(s) of the formula I, a pharmaceutically acceptable salt thereof and/or an ester thereof. Also the use of their preservative or antimicrobial properties in said pharmaceutical compositions by the addition of one or more compounds of the formula I is included.
  • additives both in the case of foods and of cosmetics, as well as in the case of pharmaceuticals (the term pharmaceuticals also including nutraceuticals), may exhibit more than one property as selected from the above lists or other not cited properties, e.g. preservatives may also act as acidity regulators and vice versa, or e.g. antioxidants may act as preservatives as well as acidity regulators, or other thinkable multi functional uses.
  • preservatives may also act as acidity regulators and vice versa
  • antioxidants may act as preservatives as well as acidity regulators, or other thinkable multi functional uses.
  • Medical devices are especially devices intended for use in the diagnosis of disease or other conditions, or in the cure, mitigation, treatment, or prevention of disease, in man or other animals, and mean e.g. any instrument, apparatus, appliance, material or other article, whether used alone or in combination, including the software necessary for its proper application intended by the manufacturer to be used for human beings for the purpose of:
  • Possible implants include but are not limited to:
  • Surgical meshes or other 2-dimensionally extended or extendable materials such as membranes
  • polypropylene meshes e.g. BARD MESH® from Bard Inc., SURGIPRO® from US Surgical, Inc., TRELEX® from Boston Scientific, PROLENE® or MERSILENE® from Ethicon, Inc.
  • polyester meshes e.g. MERSILENE® from Ethicon
  • expanded polytetrafluoroethylen meshes e.g. SOFT TISSUE PATCH® from W.L. Gore & Associates, Inc
  • polyamide materials or the like e.g.
  • PRECLUDE® Pericardial Membrane PRECLUDE® Peritoneal Membrane and PRECLUDE® Dura Substitute Membrane each from W.L. Gore & Associates, silicone elastomers, such as SILASTIC Rx® Medical Grade Sheeting from Dow Corning or mikroporous Polypropylen from Celgard, Inc., for example where the implant is used to seal compartmenting tissues or structures in the body, such as peritoneum, pleura, diaphragma, lung, pericard or the like; b) electrode coatings, e.g. for electrodes of pacemakers or neural or muscular stimulation or the like, e.g.
  • orthopaedic implants such as hard tissue, bone or joint replacing implants, for example for hip or knee or other joint repair, e.g. implants made from stainless steel, cobalt-chromium alloys, titanium or titanium alloys, pure titanium, tantalum, plastics materials such as polyethylene, polypropylene, polylactate, carbon fibre, ceramics or compounds of two or more such materials; e) screws, nails, threads, plates or other hard fixation materials for hard tissues, e.g. from the materials mentioned under d); f) oral, such as dental implants, e.g.
  • Bone fillers such as bone cement composites, hydroxyl apatite composites or polycaprolactone (Blurr plug); h) implants coming into contact with blood, such as vascular grafts, e.g. from biocompatible plastics materials, such as extended polytetrafluoroethylene or poly[ethylene terephthalate], stents (e.g. from metals or metal alloys, such as (e.g. 316L) stainless steel, cobalt-chromium-nickel-molybdenum-iron alloy, Tantalum, shape memory alloys, e.g. nitinol, or (e.g.
  • shape memory polymer materials such as polyethylene or polyurethane
  • heart or venous valves e.g. from polymer or metal or natural materials or combinations thereof, e.g. pyrolytic carbon, titanium coated with pyrolytic carbon, and the sewing ring cuff is e.g. teflon, polyester or dacron
  • stent/valve combinations or continuous accesses e.g. to veins, or to the peritoneum e.g. for peritoneal dialysis or the like
  • implants for delivery of signals or chemical substances e.g. drugs, coming into contact with tissue and/or body fluids, e.g.
  • organs or tissues for transplantation e.g. to decrease the expression of antigens evoking transplant rejection, especially autografts, allografts, heterografts or xenografts
  • skin substitutes or wound coating materials such as natural (e.g. keratinocytes in combination with human fibroblasts in bovine type I collagen or other ECM proteins and cytokines, such as Apligraf® (Organogenisis Inc.), or from synthetics, or combinations with natural materials e.g. synthetic polysiloxanes with bovine type I collagen and chondroitin-6-sulphate (e.g.
  • Integra® Johnson & Johnson Medica Care Life
  • synthetics alone or combined with human dermal tissue (e.g. Tanscyte® (Advanced Tissue Sciences Inc.)), allografts, collagen (e.g. in reconstituted form) or the like; l) suturing materials (especially for internal sutures not accessible from the outside), e.g. from absorbable or non-absorbable synthetics or natural materials (e.g. cat gut).
  • human dermal tissue e.g. Tanscyte® (Advanced Tissue Sciences Inc.)
  • allografts e.g. in reconstituted form
  • collagen e.g. in reconstituted form
  • suturing materials especially for internal sutures not accessible from the outside
  • absorbable or non-absorbable synthetics or natural materials e.g. cat gut
  • the implants may be for permanent (e.g. in the case of joint replacement) or transitory (e.g. in the case of fixing devices or skin replacements) insertion or other administration.
  • biofilm inhibiting usefulness of the compound(s) of formula I and of compositions comprising them is of advantage.
  • active packaging materials e.g. food or beverage or pharmaceutical or surgical packaging material having a spoilage preventing/preservative effect e.g. against colonialisation by bacterial or other microorganismic films or against spoiling of materials coming into contact with other perishable products
  • active packaging materials e.g. food or beverage or pharmaceutical or surgical packaging material having a spoilage preventing/preservative effect e.g. against colonialisation by bacterial or other microorganismic films or against spoiling of materials coming into contact with other perishable products
  • cans, wraps, foils, bottles, mugs, cartons, tubs, bags, cartridges, tubes, sachets, ampoules, sacks, or the like e.g. cans, wraps, foils, bottles, mugs, cartons, tubs, bags, cartridges, tubes, sachets, ampoules, sacks, or the like.
  • the application of compound(s) of the formula I is especially by coating e.g. on surfaces coming into contact with perishable products or a human or an animal, or bulk integration (e.g. by mixing of starting materials and/or impregnation of final products) into the material.
  • the compound(s) of the formula I to medical devices and active packaging materials can especially be applied (alone or in combination with appropriate carrier materials) on surfaces coming into contact with perishable products or a human or an animal, e.g. in the form of a coating, or applied by bulk integration into the material.
  • the materials equipped (which form an embodiment of the invention) or to be equipped with one or more compounds of the formula I may comprise the compound(s) of the formula I, a physiologically acceptable salt thereof and/or an ester thereof, either in admixture to the bulk of the material, or (in the case of products with a stable surface) by covalent and/or non-covalent attachment to (parts or the whole of) said surface.
  • the surface must either expose or be chemically modified to expose functional groups which would allow for covalent bonding of the compound of the formula I either directly or via a spacer molecule.
  • covalently bound (at least bivalent) linker molecules these may allow covalent or non-covalent binding of the compounds of the formula I.
  • the linker in the covalent attachment method can be any linker.
  • Covalent binding of the compounds of the formula I with or without linkers can take place directly by reacting their precursors with the surfaces without activation or to activated surfaces on the implants or other products. Examples are
  • linker precursors are organic compounds which are furnished terminally with a thiol group, they can be bound e.g. via gold-plated surfaces or maleinimide-layered surfaces.
  • Linker precursors which, during the process of manufacture, are furnished terminally with a carboxyl or phosphate group, can be activated to active esters or the like, e.g. with EDC, so that an OH—, SH— or amino-reactive on the surface can be bound.
  • Precursors for homo- or preferably hetero-bifunctional cross-linker which can be bound to reactive groups at the surface, such as carboxyl, epoxy, OH, SH, aldehyde or amino groups; or other known methods.
  • Other directly functionalized surfaces e.g. especially polymers with plasma-coated aldehydes.
  • the material can be any substrate.
  • This substrate could be a synthetic polymer (i.e. polyacrylate, polylactide-co-glycolide, polyethylene, or polypropylene), carbon fibre, glass, boranes, metal (i.e. titanium or stainless steel), natural polymer (i.e. collagen or alginate), or any other surface that is capable of supporting a coating, e.g. in solid or fibre form, respectively.
  • Composites of two or more such materials are also included.
  • the non-covalent can, for example, be via adsorption, integration into a coating matrix or the like.
  • the compounds of the formula I in the embodiments of the invention in a further embodiment, can be used also where the materials (products) with which they are associated (e.g. by mixing in) require a heat treatment, e.g. to achieve pasteurization sterilization or the like.
  • the one or more compounds of the formula I is/are heat stable.
  • the compound(s) of the formula I fully or partially retain(s) structure and activity e.g. regarding its preservative properties after heating.
  • Heating of the antimicrobial composition can be performed at 60-130° C., such as in the range of 60-65° C., 65-70° C., 70-75° C., 75-80° C., 80-85° C., 85-90° C., 90-95° C., 95-100° C., 100-105° C., 105-110° C., 110-115° C., 115-120° C., 120-125° C., 125-130° C.
  • heating is performed at about 65-75° C., more preferred at about 70° C. In one embodiment heating is performed at about 90-110° C., more preferred at about 100° C.
  • heating is performed at about 120-125° C., more preferred at about 121° C.
  • heating can be performed for shorter or longer periods of time, such as from a minute to several hours. Heating can for example be performed for a few minutes such as in the range of about 1-5 minutes, 5-10 minutes, 10-15 minutes, 15-20 minutes, 20-25 minutes, 25-30 minutes, 30 minutes-to 1 hour.
  • preserving agents or known preservatives may be added to the pharmaceutical incl. nutraceutical and cosmeceutical, nutritive or cosmetic product as well as to the composition.
  • Preferred combinations of the compounds of the invention for use in food and beverages are with weak organic acids, especially preferred are combinations with sorbic acid and/or benzoic acid and their appropriate salts, or with natural preservatives.
  • C 1 -C 4 alkyl para-hydroxybenzoate or its salts e.g. methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben and their appropriate salts, benzylparaben, benzoic acid or its salts, e.g.
  • N-(3-chloroallyl)hexaminium chloride alcohols or polyols, such as ethanol, propylene glycol, benzyl alcohol or 2-phenoxyethanol, benzalkonium chloride, chloroacetamide, thimerosal, benzalkonium chloride, cetylpyridinium chloride, N-(3-chloroallyl)hexaminium chloride, formaldehyde donors, such as imidazolidinyl urea, diazolidinyl urea, or DMDM hydantoin, isothiazolinones, such as KATHON® CG, available commercially from Rohm & Haas, Philadelphia, Pa., which contains a chloro-substituted isothiazolinone (methylchloroisothiazolinone), other chlorinated aromatic compounds, such as chlorphenesin, phenoxyethanol, vicinal diols, such as a 1,2-alkan
  • the compound(s) of the formula I can also be used as emulsifiers, in addition to use of their preservative properties.
  • the compound or compounds of the formula I are preferably comprised, taking the weight or the material to which it is added and the compound(s) of formula I as 100 weight %, in a relative weight share of 0.00001 to 10 weight percent.
  • the compound or compounds of the formula I are preferably added/comprised in a concentration e.g. in the range from 50 to 20000 ppm, e.g. from 100 to 1000 ppm, for example from 10 to 120 ppm, such as from 30 to 60 ppm, or e.g. from 0.1-150 ppm, where ppm refers to weight parts per million.
  • MIC Minimum inhibitory concentration
  • an MIC value developed over a period of 24 hours incubation may not be the same value developed after 48 hours or longer.
  • a substance may exhibit an observable MIC during the first 24 hours of an experiment, but exhibit no measurable MIC relative to the positive control after 48 hours.
  • the preserving properties of the compounds of the invention e.g. compounds of the formula I can be evaluated according methods cited in the art such as WO 2010/062548. For example, they can be determined for beverages using the method described in Example 3 in WO 2010/062548 which is incorporated herein by reference.
  • a single preparation of base beverage is employed to prepare each of five tests and consists of 4% apple juice, 68 g/l sucrose, 52 g/l glucose, 2 g/l fructose in batch water which is formulated to 90 ppm hardness with clalcium chloride and magnesium chloride.
  • a pH of 3.4 is achieved through combinations of malic acid and sodium malate for all preparations regardless of the presence or absence of compounds of the formula I.
  • the total combined quantity of sodium malate and malic acid is near constant, but the ratio of malic acid and malate may vary slightly given the presence of compound of the formula I. It is relevant that the beverage employed for testing does not naturally contain any substance with measurable antimicrobial activity such as in essential oils. Where required, compound of the formula I is supplemented from separately prepared stock solutions. Dimethyl dicarbonate is delivered by means of a hypodermic needle (Hamilton syringe) through septum that seals the test vessel against loss of moisture. Dimethyl dicarbonate stock solution consists of 1 ml dimethyl dicarbonate (1.25 g) in 49 ml of 100% ethanol (25 mg/ml). Hence, a microliter of stock contains 25 microgram of dimethyl dicarbonate.
  • the first embodiment of the invention is that defined in claim 1 , or a method comprising the use mentioned therein.
  • Another invention embodiment relates to the use or method according to any one of paragraphs A) to D) above, wherein the compound or compounds of the formula I, or a physiologically acceptable salt, or a physiologically acceptable ester thereof, is added to enhance the stability against microorganisms.
  • F) Another invention embodiment relates to the use or method according to paragraph E) above, where the microorganism is at least one microorganism selected from the group consisting of mold, yeast and bacteria of a beverage or a food or a cosmetic.
  • Another invention embodiment relates to the use or method according to any one of paragraphs A) to F) above, where at least one additional preservative is added.
  • Another invention embodiment relates to the use or method according to any one of paragraphs A) to K), where the material is subjected to a heat treatment before, during or after addition of the compound(s) of the formula I, a physiologically acceptable salt thereof and/or an ester thereof, as defined in any one of paragraphs A), C), D) or H) to K), especially heating the material to a temperature from 60 to 130° C.
  • Another invention embodiment relates to a compound or a mixture of compounds of the formula I shown in paragraph A) or as defined in any one of paragraphs C), D) or H) to L), where the moiety R carries at least one hydroxyl group esterified with an acid with 3 or more carbon atoms, a physiologically acceptable salt, and/or an ester thereof.
  • Another invention embodiment relates to the compound or compound mixture of paragraph M), wherein the acid is a C 3 -C 10 -alkanoic acid, especially isovaleric acid; a physiologically acceptable salt, and/or an ester thereof.
  • Another invention embodiment relates to a compound of the formula I shown in claim 1 , selected from the group of compounds represented in Table 1 with the following compound numbers: [1], [12], [13], [14], [17] and [18], and in a broader aspect from compound [4], a physiologically acceptable salt, and/or an ester thereof.
  • a further embodiment of the invention relates to a preservative or antimicrobial composition, comprising as active agent a compound or a mixture of compounds of the formula I, a physiologically acceptable salt thereof, and/or an ester thereof, as shown or defined in any one of paragraphs A), C), D) and H) to O), alone or with another additive, such as a carrier material, where the preservative composition is especially for use in a cosmetic, a food, a beverage, a pharmaceutical, a medical device, or an active packaging material.
  • Another invention embodiment relates to the composition according to paragraph P) which is a powder.
  • Another invention embodiment relates to the composition according to paragraph P) which is a liquid.
  • composition according to paragraph P) which is a coating or film.
  • T) Another invention embodiment relates to the composition according to any one of paragraphs P) to S), wherein the preservative or antimicrobial composition is for enhancing the stability against microorganisms.
  • U) Another invention embodiment relates to the composition according to paragraph T), wherein the microorganisms are at least one microorganism selected from the group consisting of mold, yeast and bacteria.
  • V) Another invention embodiment relates to the composition according to any one of paragraphs P) to U), being a preservative or antimicrobial composition for a pharmaceutical, a medical device, a food container, a beverage container, or especially a food, a beverage or a cosmetic or a home care product.
  • Another invention embodiment relates to a method of enhancing microbial stability of a material, comprising adding one or more compounds of the formula I, a physiologically acceptable salt thereof, and/or an ester thereof, as shown or defined in any one of paragraphs A), C), D) or H) to O) to a material, preferably a material selected from the group consisting of a cosmetic, a food, a beverage, a pharmaceutical, a medical device, and an active packaging material.
  • BA Another invention embodiment relates to the method of paragraph AA), wherein the material is a beverage or a food.
  • CA Another invention embodiment relates to the method of paragraph AA), wherein the material is a cosmetic.
  • Another invention embodiment relates to the material in the form of a compound or a mixture of compounds of the formula I, a physiologically acceptable salt thereof and/or an ester thereof, according to paragraph FA), where the beverage is selected from the group consisting of water, flavoured water, fortified water, a flavoured beverage, carbonated water, a juice, cola, lemon-lime, ginger ale, root beer beverages which are carbonated in the manner of soft drinks, a syrup, a diet beverages, a carbonated soft drink, a fruit juice, other fruit containing beverages which provide the flavor of fruit juices and contain greater than 0% fruit juice but less than 100% fruit juice, fruit flavored beverages, vegetable juices, vegetable containing beverages, which provide the flavor of any of the aforementioned vegetable juices and contain greater than 0% vegetable juice but less than 100% vegetable juice, isotonic beverages, non-isotonic beverages, soft drinks containing a fruit juice, coffee, tea, tea beverages prepared from tea concentrate, extracts, or powders, drinkable dairy products, hot chocolate, chocolate powders,
  • HA Another invention embodiment relates to the material according to paragraph DA) which is a beverage precursor, especially a concentrate, syrup or powder.
  • IA Another invention embodiment relates to the material according to paragraph DA) which is a food.
  • JA Another invention embodiment relates to the material according to paragraph DA) which is a cosmetic.
  • KA Another invention embodiment relates to the material in the form of a cosmetic according to paragraph JA) which is cream, emulsion, lotion, gel or oil for the skin; a face masks, a tinted base, a make-up powder, an after-bath powder, a hygienic powder, a toilet soap, a deodorant soap, a perfumes, a toilet water, an eau de Cologne, a bath or shower preparation; a depilatory; a deodorant, an anti-perspirant, a hair care product; a setting product; a cleansing product; a conditioning product; a hairdressing product; a shaving products; a product for making up and removing make-up from the face and the eyes, a product intended for application to the lips, a products for care of the teeth and/or the mouth; a product for nail care and/or make-up, a product for external intimate hygiene, a sunbathing product, a product for tanning without sun, a skin-whitening product,
  • LA Another invention embodiment relates to the cosmetic material according to any one of paragraphs JA) and LA), which comprises one or more additives selected from the group consisting of abrasives, absorbents, anti-cakings, anti-corrosives, anti-dandruffs, anti-foamings, anti-microbials, anti-oxidants, anti-perspirants, anti-plaques, anti-seborrhoeics, anti-statics, astringents, bindings, bleachings, bufferings, bulkings, chelatings, cleansings, cosmetic colorants, denaturants, deodorants, depilatories, detanglings, emollients, emulsifiers, emulsion stabilizers, film formings, foamings, foam boosters, gel formers, hair conditioners, hair dyes, hair fixers, hair waving or straighteners, humectants, hydrotropers, keratolytics, masking agents, moisturing, nail conditioners
  • the formulations can be or comprise or contain cosmetic additives selected from sunscreens, preservatives, bactericides, fungicides, virucides, cooling substances, insect repellents, plant extracts, antiinflammatory substances, wound healing accelerators, film-forming substances, customary antioxidants, vitamins, 2-hydroxycarboxylic acids, skin colorants, active ingredients for promoting hair growth, skin care products, softening, moisturizing and/or moisture-retaining substances, fats, oils, saturated fatty acids, monounsaturated or polyunsaturated fatty acids, alfa-hydroxy acids, polyhydroxy fatty acids or their derivatives, waxes, alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives or chelating agents, antidandruff substances, hair care products, perfumes, antifoams, dyestuffs, pigments with a coloring action, thickeners, surface-active substances
  • cosmetic additives selected from sunscreens, preservatives, bactericides, fungicides
  • NA) Another invention embodiment relates to the material according to any one of paragraphs DA) to MA) comprising an additional preservative.
  • PA) Another invention embodiment relates to the material according to any one of paragraphs DA) to NA) which is obtained after heat treatment, especially at 60 to 130° C.
  • QA) Another invention embodiment relates to a compound of the formula I or a mixture of such compounds, according to any one of paragraphs A), B) and H) to O) or a composition comprising them, especially according to any one of paragraphs P) to S) mentioned above, as a biofilm inhibiting agent and its corresponding use, e.g. by administering, or in methods comprising administering, one or more compounds of the formula I, or a composition comprising them, to surfaces or materials coming into contact with surfaces.
  • the invention relates to (the use of) one or more compounds of the above formula I, one or more physiologically acceptable salts of a compound of the above formula I, or a mixture thereof,
  • the invention relates to (the use of) one or more compounds of the above formula I, one or more physiologically acceptable salts of a compound of the above formula I, or a mixture thereof,
  • ring A is a xylopyranoside moiety
  • ring B is a xylopyranosyl moiety
  • ring C is glucopyranosyl moiety
  • one or more of the hydroxyl groups of said rings are esterified with a C 2 -C 10 -alkanoic acid, preferably a C 3 -C 10 -alkanoic acid, more preferably a C 3 -C 6 -alkanoic acid, as agent with preservative properties against (i) Gram-positive bacteria and/or (ii) fungi, as indicated above, preferably comprising adding the agent to a material, where said material is preferably selected from the group consisting of a cosmetic product, a food product, a beverage, a pharmaceutical product, a medical device, a medical hygiene product, a home care product, and an active packaging material.
  • preferred compounds or mixtures of compounds of the formula I shown above are defined by a trisaccharide carbohydrate moiety R carrying at least one hydroxyl group esterified with an acid with 3 or more carbon atoms, particularly wherein the acid is a C 3 -C 10 -alkanoic acid, especially wherein the acid is a C 3 -C 6 -alkanoic acid, and/or a physiologically acceptable salt thereof.
  • the invention relates to (the use of) one or more compounds of the above formula I, one or more physiologically acceptable salts of a compound of the above formula I, or a mixture thereof (preferably as defined in one of the preferred or particularly preferred embodiments herein) as agent with preservative properties against
  • the terms “for oral consumption”, “orally consumable” or “food product” and the like in particular refer to materials which are intended to be swallowed by a human being in an unchanged (i.e. by direct oral consumption, “ready-to-eat”, “ready-to-drink”) or processed state and then to be digested.
  • Yeasts are able to grow in orally consumable compositions, such as foods and beverages, with a low pH values (generally pH 5.0 or lower), and in the presence of sugars, organic acids or other easily metabolized carbon sources. During their growth, yeasts metabolize some food components and produce metabolic products. This causes the physical, chemical, and sensory properties of an orally consumable composition to change, and the composition is spoiled. The growth of yeast within orally consumable compositions is often seen on their surface, as in cheeses or meats, or by the fermentation of sugars in beverages, such as juices, and semi-liquid products, such as syrups and jams.
  • compositions Of particular relevance in the context of orally consumable compositions are Aspergillus niger, Brettanomyces bruxellensis, Brettanomyces naardenensis, Dekkera bruxellensis, Dekkera naardenensis, Saccharomyces cerevisiae, Zygosaccharomyces bailii, Zygosaccharomyces bisporus, Zygosaccharomyces florentinus , and Zygosaccharomyces rouxii.
  • the yeasts of the Zygosaccharomyces genus have had a long history as spoilage yeasts within the food industry. This is due mainly to the fact that these species can grow in the presence of high sucrose, ethanol, acetic acid, sorbic acid, benzoic acid, and sulphur dioxide concentrations (which are some of the commonly used preservatives in orally consumable compositions).
  • Clostridium botulinum is a Gram-positive bacterium that produces several toxins, inter alia neurotoxins that cause the flaccid muscular paralysis seen in botulism. Botulism poisoning can occur due to improperly preserved food or canned food that was not processed using correct preservation times and/or pressure. Mainly slightly acidic or neutral food is at risk which was stored under anaerobic conditions (generally pH>4.6) and storage temperatures above 10° C. The latter is generally given for canned foods, such as meat and fish preserves, mayonnaise, but also slightly acidic fruit or vegetables.
  • Bacillus subtilis is known to cause disease in severely immunocompromised patients, and it may cause food poisoning. Bacillus subtilis spores can survive the extreme heat during cooking. Bacillus subtilis strains are responsible for causing ropiness in spoiled bread dough.
  • Micrococcus luteus is found in soil, dust, water and air, and is part of the normal flora of the mammalian skin and mucosae. It is further a food spoiling bacterium and often found on spoiled meat. In immunocompromised patients, Micrococcus luteus may cause infections.
  • Propionibacterium acnes is largely commensal and part of the healthy adult human skin flora. It lives primarily on fatty acids in sebum secreted by sebaceous glands in the follicles and is linked to the skin condition acne. Propionibacterium acnes can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery.
  • Dental plaque is a biofilm formed by colonizing bacteria trying to attach themselves to a smooth tooth surface.
  • a microorganism significantly contributing dental plaque and tooth decay is Streptococcus mutans.
  • the rice blast fungus Magnaporthe grisea (syn.: Pyricularia olyzae ; conidial stage/anamorph: Pyricularia grisea) attacks leaves, grains, and other parts of rice plants.
  • Athlete's foot (tinea pedis) is a communicable disease caused by parasitic molds in the genus Trichophyton , predominantly Trichophyton rubrum and/or Trichophyton mentagrophytes . These can also cause skin infections on other areas of the body, most often under toenails (onychomycosis) or on the groin (tinea cruris).
  • Mucor species are often involved in the composting of plants and plant residues and are found on foods such as milk, butter, cheese and tomatoes.
  • Mucor plumbeus has a worldwide distribution in soil. As spoilage germ, Mucor plumbeus is mainly found on fermented foods (such as bread, beer, wine, cheese, yoghurt, kefir, salami), and on grain.
  • Mucormycosis (sometimes also referred to as Zygomycosis) is the term used to describe fungal infections caused by fungi in the order Mucorales, inter alia by species in the Mucor genus. These rare yet serious and potentially life-threatening fungal infections usually affect the face, oropharyngeal (nose/mouth) cavity, gastrointestinal tract or the skin. Individuals with immune disorders (immunocompromised) are more prone to this type of fungal infection.
  • Rhizopus is a genus of fungi found on plants and on various other organic substrates, including mature fruits and vegetables, jellies, syrups, bread, peanuts and tobacco. Some Rhizopus species are opportunistic agents of human zygomycosis (fungal infection) and can be fatal. Rhizopus infections are also an associated complication of diabetic ketoacidosis.
  • Rhizopus arrhizus is the most common cause of mucormycosis in humans and occasionally infects other animals.
  • Rhizopus nigricans is a fungus commonly known as bread mold and is the most common species of Rhizopus . It is found on old food. The spores, dispersed in hot dry weather, contain allergenic proteins, which can produce respiratory and nasal symptoms. Food handling workers are particularly at risk if they are mold allergic.
  • Rhizopus stolonifer black bread mold
  • Rhizopus stolonifer is a widely distributed mold and is most commonly found growing on bread and soft fruits such as bananas and grapes, and causes damage to the surface where it lives. It is capable of causing opportunistic infections of humans.
  • Staphylococcus aureus is the most common species to cause staphylococcal infections. Staphylococcus aureus can cause a range of illnesses, from minor skin infections to life-threatening diseases such as pneumonia, meningitis, osteomyelitis, endocarditis, toxic shock syndrome, bacteremia, and sepsis. Staphylococcus aureus strains are also responsible for food poisoning through the production of an enterotoxin, particularly in meat, meat products (e.g. luncheon meats, cold meats, sausages), milk, milk products, such as cheese).
  • meat, meat products e.g. luncheon meats, cold meats, sausages
  • milk milk products, such as cheese
  • Clostridium perfringens is widely present in nature and can be found as a normal component of decaying vegetation, but also in the intestinal tract of humans. Clostridium perfringens bacteria often cause of foodborne illness, particularly in poorly prepared meat and poultry. Often, meat is well prepared, but too far in advance of consumption. Since Clostridium perfringens forms spores that can withstand cooking temperatures, upon standing or storage germination ensues and infective bacterial colonies develop. Clostridium perfringens causes a wide range of symptoms: it is a very common cause of food poisoning and the most common bacterial agent for gas gangrene, which is necrosis, putrefaction of tissues, and gas production.
  • Fungi of the genus Aspergillus may cause infections causing a variety of diseases called aspergillosis (common forms are allergic bronchopulmonary aspergillosis, pulmonary aspergilloma and invasive aspergillosis).
  • Aspergillus flavus is a common mold in the environment, and can cause storage problems in stored grains. It can also be a human pathogen, associated with aspergillosis and other infections.
  • Aspergillus fumigatus is one of the most common Aspergillus species to cause disease in individuals with an immunodeficiency. In immunocompromised individuals, such patients receiving immunosuppressive therapy for autoimmune or neoplastic disease, organ transplant recipient, and people with AIDS or leukemia, the fungus is more likely to become pathogenic and cause aspergillosis. Aspergillus fumigatus primarily causes invasive infection in the lung (e.g. chronic pulmonary infections) and represents a major cause of morbidity and mortality in these individuals.
  • Aspergillus niger causes black mold on certain fruits and vegetables such as grapes, onions, and peanuts, and is a common contaminant of food. For example, Aspergillus niger causes a common postharvest disease of onions. Aspergillus niger is less likely to cause human disease than some other Aspergillus species, but, if large amounts of spores are inhaled, a serious lung disease (aspergillosis can occur). Aspergillus niger is one of the most common causes of otomycosis (fungal ear infections).
  • Chlamydia infection is one of the most common sexually transmitted infections in humans, and caused by the bacterium Chlamydia trachomatis. Chlamydia is a major infectious cause of human genital and eye disease. Chlamydia conjunctivitis or trachoma is a common cause of blindness worldwide. Both sexes can display urethritis, proctitis, trachoma, and infertility. If untreated, chlamydial infections can cause serious health problems. Chlamydia trachomatis is also an important neonatal pathogen, where it can lead to infections of the eye (trachoma) and pulmonary complications.
  • Enterococcus faecalis inhabits the gastrointestinal tracts of humans and other mammals. It may cause endocarditis and bacteremia, urinary tract infections, meningitis, and other infections in humans (e.g. in root canal-treated teeth). It can even cause life-threatening infections in humans, especially in hospital environment.
  • Listeria may be been found in uncooked meats, uncooked vegetables, fruit, pasteurized or unpasteurized milk, foods made from milk, and processed foods. Pasteurization and sufficient cooking kill Listeria ; however, contamination may occur after cooking and before packaging. For example, processing plants producing ready-to-eat foods, such as hot dogs, deli meats, fish products, cheeses, milk, and deli salads, follow extensive sanitation policies and procedures to prevent Listeria contamination.
  • the major human pathogen in the Listeria genus is Listeria monocytogenes . It is usually the causative agent of listeriosis, a serious bacterial infection caused by eating food contaminated with Listeria monocytogenes.
  • Yeasts of the Candida genus are a group of opportunistic pathogens that causes oral and vaginal infections in humans, known as candidiasis.
  • the pathogenic yeasts of candidiasis are Candida albicans, Candida tropicalis, Candida stellatoidea, Candida glabrata, Candida krusei, Candida parapsilosis, Candida guilliermondii, Candida viswanathii , and Candida lusitaniae , of these Candida albicans being the most important and most relevant.
  • Candida glabrata is the second most common Candida pathogen after Candida albicans , also causing infections of the urogenital tract, and of the bloodstream (candidemia).
  • Candida glabrata has been shown to be a highly opportunistic pathogen and is especially prevalent in immunocompromised individuals and elderly.
  • Candida glabrata can also adhere to biotic and abiotic surfaces, thereby forming microbial “biofilms” on e.g. urinary catheters or indwelling intravenous catheters. It may also cause problems with dental devices, such as dentures.
  • Staphylococcus aureus Candida albicans, Aspergillus brasiliensis and Aspergillus niger are likely microbiological contaminants of cosmetic formulations.
  • Species of certain bacteria such as Staphylococcus epidermidis, Corynebacterium xerosis, Corynebacterium minutissimum and Brevibacterium epidermidis are largely responsible for the formation of underarm and/or foot odor, or body odor in general. Brevibacterium linens inter alia causes foot odor.
  • the present invention relates to one or more compounds of formula I and/or the physiologically acceptable salts thereof, particularly one or more compounds selected from the group consisting of [1], [2], [3], [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14], [18], [19], [20], [21] and the physiologically acceptable salts thereof, for use in the prophylactic and/or therapeutic treatment of a disorder, disease or condition selected from the group consisting of
  • mycoses fungal infections
  • Aspergillus preferably Aspergillus, Candida or Mucor associated mycoses, particularly Candida associated mycoses.
  • mycoses selected from the group consisting of candidiasis [in particular oral (thrush) Candida infections, infections of the urogenital (e.g. vaginal) tract by Candida bacteria (in particular by Candida albicans and/or Candida glabrata ), diaper candidiasis ( Candida associated diaper dermatitis, diaper rash)], invasive candidiasis (particularly candidemia (infections of the bloodstream)), aspergillosis and mucormycosis.
  • candidiasis in particular oral (thrush) Candida infections, infections of the urogenital (e.g. vaginal) tract by Candida bacteria (in particular by Candida albicans and/or Candida glabrata ), diaper candidiasis ( Candida associated diaper dermatitis, diaper rash)], invasive candidiasis (particularly candidemia (infections of the bloodstream)), aspergillosis and mucormycosis.
  • the compounds of formula I and/or the physiologically acceptable salts thereof are particularly beneficial for use in the prophylactic treatment of a disorder, disease or condition mentioned above.
  • the term “effective amount” or “effective dose” refers to the (preferably oral) administration of an effective dose of one or more compounds of formula I and/or the physiologically acceptable salts thereof that produces the effects for which it is administered.
  • the term “therapeutical” or “therapeutically” refers to the (in particular oral) administration of a therapeutically effective dose of one or more compounds of formula I and/or the physiologically acceptable salts thereof (preferably in form of a mixture, a composition or a material as defined in the context of the present invention) that produces the effects for which it is administered, i.e. that will elicit the biological or medical response (in vitro or in vivo, preferably in vivo in a mammal, particularly in vivo in human being) that is being sought, in particular the amelioration and/or alleviation of the symptoms of the disorder, disease or condition being treated up to and including complete cure.
  • prophylactic refers to the (in particular oral) administration of a prophylactically effective dose of one or more compounds of formula I (preferably in form of a mixture, a composition or a material as defined in the context of the present invention) that produces the effects for which it is administered, i.e. that will elicit the biological or medical response (in vitro or in vivo, preferably in vivo in a mammal, particularly in vivo in a human being) that is being sought, in particular the prevention of the onset of a disorder, disease or condition in individuals at risk for such disorder, disease or condition as mentioned herein.
  • the present invention also relates to a method of reducing the activity and/or number of pathogenic Gram-positive bacteria and/or pathogenic fungi in an immunocompromised individual, comprising the following step:
  • administering preferably orally or topically to a mammal, particularly an immunocompromised mammal, particularly an immunosuppressed human being, an effective total amount of
  • the pathogenic Gram-positive bacteria are selected from the group consisting of the genera Bacillus, Clostridium, Listeria, Micrococcus and Staphylococcus , more preferably selected from the group consisting of Bacillus cereus, Clostridium sporogenes, Clostridium perfringens, Listeria monocytogenes, Micrococcus luteus, Staphylococcus aureus, Staphylococcus epidermidis.
  • the pathogenic fungi are selected from the group consisting of the genera Aspergillus and Candida , more preferably selected from the group consisting of Aspergillus flavus, Aspergillus fumigatus, Candida albicans, Candida glabrata, Candida lusitaniae , and Candida tropicalis.
  • the present invention also relates to a method for the prophylactic and/or therapeutic treatment of a disease, disorder or condition, comprising the following step:
  • administering preferably orally or topically to a mammal, particularly an immunocompromised mammal, particularly an immunosuppressed human being, an effective total amount of
  • the compounds of formula I (for use) according to the present invention and/or the physiologically acceptable salts thereof show a comparatively weak activity against Gram-negative bacteria, such as Escherichia coli, Pseudomonas aeruginosa, Pseudomonas putida or Salmonella typhimurium .
  • Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Pseudomonas putida or Salmonella typhimurium .
  • Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, Pseudomonas putida or Salmonella typhimurium .
  • MIC values >100 ppm were observed, typically in the range of 200-500 ppm.
  • a material according to the present invention preferably a cosmetic or a pharmaceutical, comprises (i) one or more compounds of formula I (for use) according to the present invention and/or the physiologically acceptable salts thereof, and (ii) one or more agents exhibiting an antimicrobial activity against Gram-negative bacteria, preferably selected from the group consisting of Triclosan® (2,4,4′-trichloro-2′-hydroxydiphenyl ether), chlorhexidine, chlorhexidine salts (preferably chlorhexidine diacetate, chlorhexidine dichloride, chlorhexidine digluconate), octenidine, octenidine dihydrochloride, 2-bromo-2-nitropropane-1,3-diol, polyaminopropyl biguanide, imidazolidinyl urea, diazolidinyl urea, chlorphenesin, DMDM hydantoin, sodium hydroxymethylglycinate, phenoxyethanol, isothi
  • a material according to the present invention preferably a cosmetic or a pharmaceutical, comprises (i) one or more compounds of formula I (for use) according to the present invention and/or the physiologically acceptable salts thereof, and (ii) one or more parabens (para-hydroxybenzoic acid esters) and/or the salts thereof, preferably one, two or more parabens selected from the group consisting of methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, benzylparaben and the physiologically acceptable salts (preferably the sodium salts) thereof.
  • parabens para-hydroxybenzoic acid esters
  • R z denotes H or C 2 -C 6 -alkanoyl, preferably H, acetyl or C 5 -alkanoyl, more preferably H, acetyl or isovaleryl, most preferably isovaleryl
  • R y denotes H or C 2 -C 6 -alkanoyl, preferably H or acetyl
  • R x independent of each other, each denote H or C 2 -C 6 -alkanoyl, preferably H or acetyl, with the proviso that at least one of R x , R y and R z is not hydrogen.
  • R z denotes H, acetyl or isovaleryl, most preferably isovaleryl
  • R y denotes H or C 2 -C 6 -alkanoyl, preferably H or acetyl
  • R x independent of each other, each denote H or C 2 -C 6 -alkanoyl, preferably H or acetyl, with the proviso that at least one of R y and R z is not hydrogen, preferably R z is not hydrogen.
  • mixtures comprising (i) two, three, four, five, six or more compounds of the above preferred formula I, (ii) two, three, four, five, six or more physiologically acceptable salts of a compound of the above preferred formula I, or a mixture thereof, or (iii) one, two, three or more compounds of the above preferred formula I and one, two, three or more physiologically acceptable salts of a compound of the above preferred formula I typically showed a broader activity spectrum and/or stronger long term inhibitory activity, particularly against yeasts and molds, especially against yeasts and molds of relevance regarding food, beverage and/or cosmetic spoilage, in comparison to individual compounds of (preferred) formula I or a physiologically acceptable salt thereof.
  • These mixtures according to the present invention are particularly able to inhibit the growth of thermophilic molds, which are difficult to control with standard sterilizing and/or pasteurizing processes.
  • the average degree of acylation is as follows:
  • the average degree of acylation preferably is determined via 1 H-NMR quantification using an average molecular weight for the glycolipids of 985 g/mol.
  • 1 H-NMR signal used for said quantification was that of the hydrogen atom bound to the carbon atom in position C-2 (i.e. (C H )OH, the carbon atom bearing the alpha-hydroxy group relative to the carboxylic acid group at C-1).
  • a mixture according to the present invention, an extract according to the present invention, a material according to the present invention, and/or a composition according to the present invention preferably comprises less than 25 wt. % of Glykenin IVA ((2S,16R,17S,21R)-2,16,17-trihydroxy-21-[[2-O-[2-O-(6-O-acetyl- ⁇ -D-glucopyranosyl)- ⁇ -D-xylopyranosyl]-4-O-acetyl- ⁇ -D-xylopyranosyl]oxy]hexacosanoic acid), more preferably less than 20 wt. % of Glykenin IVA, particularly preferably less than 15 wt. % of Glykenin IVA, in each case based on the total amount of compounds of formula I and the physiologically acceptable salts thereof.
  • Glykenin IVA ((2S,16R,17S,21R)-2,16,17-trihydroxy-21
  • a mixture comprises compounds [1] and [7], and the physiologically acceptable salts thereof, wherein more preferably the total amount of
  • compound [1] and the physiologically acceptable salts thereof is 1 wt. % or more, more preferably 2 wt. % or more, more preferably 3 wt. % or more, and/or compound [7] and the physiologically acceptable salts thereof is 1 wt. % or more, more preferably 2 wt. % or more, more preferably 3 wt. % or more, and/or the compounds [1] and [7], and the physiologically acceptable salts thereof is 5 wt. % or more, more preferably 8 wt. % or more, even more preferably 12 wt. % or more, the weight percentages in each case relating to the total weight of the mixture,
  • a mixture according to the present invention comprises
  • a total amount of 1-20 wt. %, preferably 2-15 wt. %, of compound [1] and the physiologically acceptable salts thereof a total amount of 0-10 wt. %, preferably 0.5-5 wt. %, of compound [5] and the physiologically acceptable salts thereof, a total amount of 0-10 wt. %, preferably 0.5-5 wt. %, of compound [6] and the physiologically acceptable salts thereof, a total amount of 2-75 wt. %, preferably 5-50 wt. %, of compound [7] and the physiologically acceptable salts thereof, a total amount of 0-12 wt. %, preferably 1-8 wt.
  • a mixture according to the present invention comprises
  • Such a particularly preferred mixture according to the present invention had the following average degree of acylation:
  • n 3, 4 or 5
  • p 11 to 14 (preferably p is 12 or 13)
  • R is a moiety of formula
  • R y denotes H or C 2 -C 6 -alkanoyl, preferably H or acetyl
  • R x independent of each other, each denote H or C 2 -C 6 -alkanoyl, preferably H or acetyl.
  • R y denotes H or C 2 -C 6 -alkanoyl, preferably H or acetyl
  • each R x independently of the other R x , denotes H or C 2 -C 6 -alkanoyl, preferably H or acetyl.
  • the present invention relates to a composition
  • a composition comprising or consisting of three, four, five, six, seven, eight, nine, ten, eleven, twelve or more compounds of formula I,
  • the total amount of said compounds of formula I is greater than 75 wt. %, preferably greater than 80 wt. %, more preferably greater than 85 wt. %, particularly preferably greater than 90 wt. %, in each case based on the total weight the composition, and preferably
  • the total amount of said physiologically acceptable salts of the compounds of formula I is greater than 70 wt. %, preferably greater than 80 wt. %, more preferably greater than 90 wt. %, particularly preferably greater than 95 wt. %, in each case based on the total amount of compounds of formula I and the physiologically acceptable salts thereof, and preferably
  • the present invention relates to a composition
  • a composition comprising or consisting of three, four, five, six, seven, eight, nine, ten, eleven, twelve or more physiologically acceptable salts of one or more, preferably two, three, four, five, six, seven, eight, nine, ten, eleven, twelve or more compounds of formula I,
  • compositions according to the present invention comprising one or more physiologically acceptable salts of one or more compounds of formula I show improved, in particular longer, storage stability in comparison to the corresponding compounds of formula I in free acid form. It was also found in our own investigations that such compositions have a superior, i.e. higher, solubility in aqueous-alcoholic solvents or water in comparison to the corresponding compounds of formula I in free acid form. For example, while it is not possible to obtain a stable 1 wt. % solution of a mixture of compounds of formula I in free acid form in water, it is easily possible to produce a 10 wt. % solution of a mixture of compounds of formula I in their salt form.
  • the trisaccharide carbohydrate moiety R in the compounds of formula I—without including any substituents resulting from acylation of hydroxyl groups of said trisaccharide carbohydrate moiety R— is a beta-D-glucopyranosyl-(1 ⁇ 2)-beta-D-xylopyranosyl-(1 ⁇ 2)-beta-D-xylopyranoside moiety.
  • said trisaccharide carbohydrate moiety R preferably one, two, three or four hydroxyl groups are esterified by a C 2 -C 10 -alkanoic acid, i.e.
  • acylated hydroxyl groups in the trisaccharide carbohydrate moiety R, said acyl moiety preferably being a C 3 -C 6 -alkanoic acid, more preferably an isovaleryl (3-methyl-butanoyl) moiety.
  • such a mixture comprises, essentially consists of or consists of alkali and/or alkaline earth salts of two or more compounds of formula I, more preferably of sodium and/or potassium and/or calcium and/or magnesium salts thereof, in particular the sodium and/or potassium and/or calcium and/or magnesium salts of one, two, three, four, five, six, seven, eight, nine or more of the compounds selected from the group consisting of compounds [1], [4], [5], [6], [7], [8], [9], [10], [12], [13], [14], and [18], wherein the total amount of water preferably is less than 5 wt. %, more preferably less than 3 wt. %, and particularly preferably less than 1 wt. %, in each case based on the total weight of the mixture.
  • such a mixture comprises the sodium and/or potassium and/or calcium and/or magnesium salts of one, two, three, four, five, six, seven, eight or more of the compounds selected from the group consisting of [1], [4], [5], [6], [7], [8], [9], [10], [12], [13], [14], and [18], wherein the total amount of salts of the compounds of formula I is greater than 70 wt. %, preferably greater than 75 wt. %, more preferably greater than 80 wt. %, particularly preferably greater than 85 wt. %, in each case based on the total weight of the mixture.
  • such a mixture comprises the sodium and/or potassium and/or calcium and/or magnesium salts of one, two, three, four or all of the compounds selected from the group consisting of compounds [1], [7], [12], [13], and [18], wherein the total amount of said salts of the compounds [1], [7], [12], [13], and [18] is greater than 10 wt. %, preferably greater than 15 wt. %, more preferably greater than 20 wt. %, in each case based on the total weight of the mixture.
  • a mixture according to the present invention, and in particular of a composition comprising or consisting of one or more physiologically acceptable salts of one or more compounds of formula I (as defined above) may be further purified according to methods and materials described in U.S. Pat. No.
  • sorbent absorbent or adsorbent materials selected from the group consisting of activated carbons, charcoal, ion exchange resins (preferably a weakly basic or weakly acidic ion exchange resin, macroporous ion exchange resins in turn being preferred), silica, alumina, kieselgur (diatomaceous earth, e.g.
  • zeolites such as zeolite A, zeolite X, zeolite Y
  • silicates and aluminosilicates preferably clays and clay minerals like bentonite, kaolinite, montmorillonite, smectite, illite, chlorite.
  • a material according to the present invention comprising an above defined (preferred or particularly preferred) total amount of water are selected from the group consisting of an O/W-emulsion, a hydrodispersion, a suspension, a solution, or a hydrogel.
  • a material according to the present invention comprises a high proportion of water, preferably water in a total amount of 50 wt. % or more, more preferably of 60 wt. % or more, even more preferably 65 wt. % or more, particularly preferably 70 wt. % or more, and most preferably 75 wt. % or more, in each case based on the total weight of the material.
  • the total amount of water of an orally consumable material according to the present invention, in particular of a ready-to-drink composition according to the present invention, is 60 wt. % or more, preferably 70 wt. % or more, more preferably 75 wt. % or more, even more preferably 80 wt. % or more, in each case based on the total weight of the orally consumable material.
  • a material according to the present invention comprising an above defined (preferred or particularly preferred) total amount of water has a pH-value at 25° C. of 6.8 or less, preferably in the range of 1.5 to 6.5, more preferably in the range of 2.0 to 6.0, even more preferably in the range of 2.1 to 5.8, particularly preferably in the range of 2.2 to 5.0, and most preferably in the range of 2.3 to 4.5.
  • the one or more compounds of formula I and/or the physiologically acceptable salts thereof allow the prevention of spoilage of materials with such a high proportion of water (and preferably a pH-value at 25° C. in the range of 2.2 to 4.6) by microorganisms, within a sealed container for a period of at least 12 weeks, preferably at least 16 weeks at 25° C.
  • a reduction or substitution of conventional preservatives that may pose health and/or environmental concerns
  • the one or more compounds of formula I and/or the physiologically acceptable salts thereof allow to be used together in other known beverage preserving agents in an additive or synergistic manner to reduce the amount of preservative required and so improve the inventive beverage's sensory impact over beverages having conventional preservatives.
  • the total amount of ethyl-N-alpha-lauroyl-L-arginate and its hydrochloride preferably is in the range of 1 to 25 ppm, more preferably 2 to 12 ppm, based on the total weight of the beverage.
  • the total amount of dimethyl dicarbonate preferably is in the range of 20 to 500 ppm, more preferably 50 to 250 ppm, based on the total weight of the beverage.
  • the total amount of EDTA (ethylene diamine tetraacetic acid) and its physiologically acceptable salts is in the range of 0.5 to 50 ppm, more preferably 1 to 30 ppm, based on the total weight of the beverage.
  • the total amount of EDDS (ethylene diamine-N,N′-disuccinic acid) and its physiologically acceptable salts is in the range of 1 to 500 ppm, more preferably 20 to 450 ppm, based on the total weight of the beverage.
  • the total amount of polyphosphoric acid and its physiologically acceptable salts is in the range of 10 to 1500 ppm, based on the total weight of the beverage.
  • the total amount of the compounds of formula I preferably of the compounds [1], [2], [3], [4], [5], [6], [7], [8], [9], [10], [11], [12], [13], [14], [18], [19], [20], [21] and the physiologically acceptable salts thereof, more preferably of the compounds [1], [4], [5], [6], [7], [8], [9], [10], [12], [13], [14], [18], and the physiologically acceptable salts thereof, preferably is in the range of 0.1 to 1000 ppm, more preferably of 0.5 to 500 ppm, particularly preferably of 1 to 250 ppm, and most preferably of 2 to 150 ppm, in each case based on the total weight of the orally consumable material according to the present invention, particularly a food or beverage according to the present invention.
  • the compounds of formula I and the physiologically acceptable salts thereof are preferably used in orally consumable materials, particularly foods or beverages, according to the invention, in combination with one or more flavouring agents, preferably having a molecular weight in the range of 120 to 300 g/mol, more preferably in the range of 130 to 280 g/mol.
  • one, two, three or more of said flavouring agents are fresh, sweet, fruity, spicy and/or herbal flavouring agents, preferably selected from the group consisting of menthol (preferably L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol), isomenthone, menthone, peppermint oil, L-carvone, D-carvone, spearmint oil, cineol, eucalyptus oil, cinnamaldehyde (preferably trans-cinnamaldehyde), cinnamic alcohol, cinnamon bark oil, cinnamon leaf oil, methyl cinnamate, benzaldehyde, furfural, furfuryl alcohol, methyl salicylate, wintergreen oil, thyme oil, thymol, carvacrol, clove oil, camphene, p-cymene, alpha-terpinene, borneol, eugenol, anis
  • one, two, three or more of said flavouring agents are sweet, fruity and/or spicy flavouring agents, preferably selected from the group consisting of trans-cinnamaldehyde, cinnamic alcohol, methyl cinnamate, benzaldehyde, furfural, furfuryl alcohol, camphene, p-cymene, alpha-terpinene, borneol, eugenol, trans-anethole, anisole, cis-3-hexenol, cis-3-hexenyl acetate, D-limonene, L-limonene, linalool, citral, geraniol, geranyl acetate, nerol, citronellol, citronellal, alpha-phellandrene, beta-phellandrene, alpha-pinene, beta-pinene, vanilla extract, vanillin, ethylvanillin, 2-hydroxy-4-
  • the present invention also relates to foods, such as meat, meat products, fish and seafood products, with an increased shelf life stability and an increased resistance against the growth of Gram-positive bacteria.
  • the preparation process for manufacturing foodstuffs using the compounds of formula I and/or the physiologically acceptable salts thereof according to the invention comprises, for example, combining an uncooked meat, meat products, fish or seafood product with one or more phosphates, one or more lactates, lactic acid, and preferably further and/or a flavouring agent, followed by further processing such as packing or cooking.
  • the present invention makes use of phosphates which are functional in protein activation of meat, meat products, fish or seafood and have also properties to absorb lactates and flavouring agents.
  • the present invention relates to a foodstuff treatment composition, particularly for the treatment of meat, meat products, fish and seafood products, said composition comprising (i) one or more compounds of formula I and/or the physiologically acceptable salts thereof, (ii) lactic acid and/or lactates, and (iii) one or more phosphates.
  • % more preferably in a total amount of 1 to 20 wt. %, even more preferably in a total amount of 1.5 to 15 wt. %, (iii) one or more sodium and/or potassium phosphates selected from the group consisting of sodium and/or potassium orthophosphates, pyrophosphates (diphosphates), metaphosphates, and polyphosphates (hexametaphosphates), preferably in a total amount of 1 to 45 wt. %, more preferably in a total amount of 2 to 30 wt. %, even more preferably in a total amount of 3 to 25 wt. %, (iv) preferably water, more preferably water in a total amount of 50 wt.
  • the one or more sodium and/or potassium phosphate salts of constituent (iii) are selected from trisodium phosphate (Na 3 PO 4 ), tetrasodium pyrophosphate (Na 4 P 2 O 7 ), sodium tripolyphosphate (Na 5 P 3 O 10 ), tripotassium phosphate (K 3 PO 4 ), tetrapotassium pyrophosphate (K 4 P 2 O 7 ), potassium tripolyphosphate (K 5 P 3 O 10 ), and sodium hexametaphosphate (NaPO 3 ) 6 .
  • These foodstuff treatment compositions are particularly useful for the treatment of meat, meat products, fish and seafood products, to increase the resistance of the foodstuff against the growth of bacteria, in particular of the genera Listeria (particularly Listeria monocytogenes ), Lactobacillus, Clostridia, Micrococcus (particularly Micrococcus luteus ), and/or Bacillus (particularly Bacillus cereus ), whereby the foodstuff treatment composition is applied to the food in an amount to achieve a total amount of 0.25 to 6 wt %, preferably of 0.5 to 4 wt. %, of constituents (ii) lactic acid and lactates and (iii) phosphates in the final treated foodstuff.
  • a material according to the present invention is a cosmetic product suitable for topical application onto the mucous membrane (mucosa) and/or the epidermis of a mammal, preferably in the form of an O/W-lotion, a milk, a (hydro)gel, a body care and/or hair care product (such as preferably a shower gel and/or a shampoo, a hair conditioning product, or a deodorant), comprises
  • one, several or all mono-, di- or triols having 2 to 14 carbon atoms are selected from the group consisting of ethanol, 1-propanol, 2-propanol, ethylene glycol, 1,2-propylene glycol, glycerol (glycerin), 1,3-propandiol, 2-methyl-1,3-propandiol, trimethylolpropane, 1,2-butandiol, 1,3-butandiol, 1,4-butandiol, 1,2,3-butantriol, 1,2,4-butantriol, 1-pentanol, 2-pentanol, 3-pentanol, 1,2-pentandiol, 1,3-pentandiol, 1,5-pentandiol, 1-hexanol, 2-hexanol, 3-hexanol, 1,2-hexandiol, 1,3-hexandiol, dipropylene glycol, 1-octanol, 2-octanol,
  • a cosmetic deodorant composition according to the present invention preferably comprises
  • one or more of the further surfactants are selected from the group consisting of anionic tensides, cationic tensides, non-ionic tensides, or amphoteric tensides explicitly mentioned above.
  • the one or more compounds of formula I and/or the physiologically acceptable salts thereof (for use) according to the present invention, the extracts according to the present invention are combined with one or more ingredients selected from the group consisting of lactic acid, lactose, sucrose, calcium salts (preferably calcium phosphate, calcium gluconate, calcium lactate, and calcium chloride), calcium oxide, magnesium salts, magnesium oxide, iron salts (preferably ferrous fumarate, ferrous succinate, iron sucrate-malate, iron fructate-malate, iron sucrate-citrate, iron fructatecitrate, iron sucrate-ascorbate, iron fructate-ascorbate, and mixtures thereof), vitamin A (particularly retinol (vitamin A1)), vitamin B6, vitamin B12, vitamin C, vitamin D, vitamin E, thiamine, niacin, biotin, riboflavin, pantothenic acid, phytic acid, daidzein, genistein, proteins (preferably casein, caseinates
  • a material according to the present invention (preferably comprising an above defined preferred or particularly preferred total amount of water and having a pH-value in a preferred or particularly preferred range indicated above) suitable for oral consumption comprises a total amount of glutamic acid and sodium glutamate of less than 0.2 wt. %, preferably of less than 0.15 wt. %, more preferably of less than 0.1 wt. %, particularly preferably of less than 0.05 wt. %, and most preferably is free of glutamic acid and sodium glutamate.
  • Preferred physiologically acceptable salts of phosphoric acid are for example sodium acetate, monosodium phosphate, disodium phosphate, monopotassium phosphate, dipotassium phosphate, sodium hexametaphosphate, and sodium bis-phosphonates.
  • a more preferred orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, comprises
  • an orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, comprises one or more further constituents suitable for oral consumption, particularly
  • An orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, preferably comprises 200 ppm or more hydrogen carbonate (HCO 3 ⁇ ), more preferably 250 ppm or more hydrogen carbonate, even more preferably 300 ppm or more hydrogen carbonate, and particularly preferably 400 ppm or more hydrogen carbonate, in each case based on the total weight of the orally consumable material.
  • HCO 3 ⁇ hydrogen carbonate
  • An orally consumable material according to the present invention preferably comprises 200 ppm or more hydrogen carbonate (HCO 3 ⁇ ), more preferably 250 ppm or more hydrogen carbonate, even more preferably 300 ppm or more hydrogen carbonate, and particularly preferably 400 ppm or more hydrogen carbonate, in each case based on the total weight of the orally consumable material.
  • the total amount of carbon dioxide (CO 2 ) preferably is in the range of from 0.02 to 5.0 wt. %, more preferably in the range of from 0.05 to 3 wt. %, even more preferably in the range of from 0.1 to 2.5 wt. %, particularly preferably in the range of from 0.2 to 2.0 wt. %, most preferably in the range of from 0.25 to 1.5 wt. %, in each case based on the total weight of the orally consumable material.
  • An orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, preferably comprises one or more high potency sweeteners, preferably selected from the group indicated above, more preferably selected from the group consisting of aspartame, neotame, superaspartame, advantame, saccharin, sucralose, cyclamate, acesulfam, tagatose, monellin, stevioside, rebaudioside A, rebaudioside C, rebaudioside D, rubusosid, phyllodulcin, hernandulcin, thaumatin, brazzein, miraculin, glycyrrhizin, glycyrrhetinic acid, the physiologically acceptable salts (preferably the sodium, potassium or calcium salts) of the these compounds.
  • high potency sweeteners preferably selected from the group indicated above, more preferably selected from the group consisting of aspartam
  • An orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, preferably comprises a total amount of less than 4.5 wt. % fats and fatty oils (i.e. triglycerides), more preferably less than 3.5 wt. % fats and fatty oils, even more preferably less than 2.0 wt. % fats and fatty oils, particularly preferably less than 1.0 wt. % fats and fatty oils, and most preferably less than 0.5 wt. % fats and fatty oils, in each case based on the total weight of the orally consumable material.
  • fatty oils i.e. triglycerides
  • an orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, has a turbidity of less than 12 FNU, more preferably of less than 6 FNU, preferably measured with a Hach Turbidimeter 2100N IS.
  • Fruit juices or fruit juice concentrates that can be used are preferably derived from citrus fruits such as orange, lemon, grapefruit and tangerine, and other fruits such as apple, pear, grape, apricot and pineapple. Furthermore, fruit juices and fruit juice concentrates may be derived from soft fruits like blackberry, gooseberry, currant, blueberry, elderberry, strawberry and raspberry.
  • an orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, is an emulsion.
  • Densities of the disperse phase which are preferred for an adequate stabilization and avoidance of ringing, preferably lie in the range of from 0.92 to 1.06 g/ml, more preferably in the range of from 0.94 to 1.03 g/ml. “Ringing” is the formation of a ring around the neck of a (beverage) container which is sought to be avoided.
  • an orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, comprises one or more weighting agents, these are preferably selected from the group consisting of sucrose acetate isobutyrate (SAIB, E 444), estergum (E 445), dammar gum, and brominated vegetable oils in an amount not exceeding the respective legally authorized concentrations.
  • weighting agents these are preferably selected from the group consisting of sucrose acetate isobutyrate (SAIB, E 444), estergum (E 445), dammar gum, and brominated vegetable oils in an amount not exceeding the respective legally authorized concentrations.
  • an orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, is a cloudy (turbid) emulsion, preferably comprising one or more clouding agents, such as titanium dioxide, palm oil, or terpene oils like limonene.
  • cloudy (turbid) emulsion preferably comprising one or more clouding agents, such as titanium dioxide, palm oil, or terpene oils like limonene.
  • an orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, is an emulsion, e.g. prepared as described in U.S. Pat. No. 5,616,358, EP 2 025 250 or EP 1 151 677.
  • an orally consumable material according to the present invention in particular a ready-to-drink composition according to the present invention, is a cloudy (turbid) emulsion
  • the D90 particle (droplet) size of the disperse phase is in the range of from 0.15 to 1.0 ⁇ m (microns), in some preferred embodiments in the range of from 0.35 to 0.5 ⁇ m, in some other preferred embodiments in the range of from 0.6 to 0.75 ⁇ m.
  • a beverage according to the present invention comprises a terpene oil, more preferably a terpene citrus oil.
  • Preferred terpene oils in the context of the present invention comprise or consist of orange, lemon and/or grapefruit oils and fractions thereof, preferably limonene (especially D-limonene) and/or orange oil terpenes.
  • a material according to the present invention may additionally comprise one or more physiological cooling agents, preferably selected from the group consisting of menthone derivatives (preferably L-menthone glycerol ketal), p-menthane-3,8-diol, cubebol, isopulegol and its esters (preferably L-( ⁇ )-isopulegol, L-( ⁇ )-isopulegol acetate), menthyl ethers (preferably (L-menthoxy)-1,2-propanediol, (L-menthoxy)-2-methyl-1,2-propanediol, L-menthyl-methyl ether), menthyl esters (preferably menthyl formate, menthyl acetate, menthyl isobutyrate, menthyl lactate, L-menthyl-L-lactate, L-menthyl-D-lactate, L-menthyl-(2-methoxy)
  • physiological cooling agents preferably selected from the group consisting of
  • preferred cosmetic products of the invention are oral hygiene products (oral care products).
  • Preferred oral hygiene products are creams, gels, pastes, foams, emulsions, suspensions, aerosols, sprays or chewing gums. Such formulations serve to clean and care for the tooth substance and oral cavity and to freshen the breath.
  • More preferred oral hygiene products are toothpastes, tooth gels, 2-in-1 tooth gels, mouthwashes, mouth rinses, gargles and mouth or breath sprays.
  • a cosmetic, in particular an oral hygiene oral product according to the invention can contain further auxiliary substances such as are conventionally used in such preparations, for example further preservatives, abrasives, antibacterial agents, anti-inflammatory agents, irritation-preventing agents, irritation-inhibiting agents, further antimicrobial agents, antioxidants, astringents, antiseptic agents, antistatics, binders, buffers, support materials, chelating agents, cell stimulants, cleansing agents, conditioning agents, further surface-active substances, deodorising agents, softeners, emulsifiers, enzymes, essential oils, film formers, foaming agents, foam stabilisers, substances to prevent foaming, gelling agents, moisturizing substances, moisture-retaining substances, bleaching agents, optical brighteners, dirt-repelling agents, lubricants, opacifiers, brighteners, polymers, powders, proteins, silicones, skin-calming agents, skin-cleansing agents, skin care agents, skin-healing agents, skin-cooling agents, skin-warming agents, stabili
  • Aroma substances which preferably are part of an oral hygiene product according to the invention are preferably selected from the group consisting of aniseed oil, basil oil, bitter almond oil, camphor oil, citronella oil, citrus oils, eucalyptus citriodora oil, eucalyptus oil, camomile oil, spearmint oil, limette oil, mandarin oil, clove oil, orange oil, peppermint oil, sage oil, thyme oil, wintergreen oil, cinnamon oil, cinnamon bark oil, l-menthol, menthone, isomenthone, 1,8-cineol (eucalyptol), carvone, alpha-terpineol, methyl salicylate, 2′-hydroxpropiophenone, and menthyl methyl ether.
  • sanitary articles preferably selected from the group consisting of wet wipes, sanitary towels, diapers, tampons, handkerchiefs and refreshing tissues containing one or more compounds of formula I (to be used) according to the invention and/or one or more physiologically acceptable salts thereof.
  • Said sanitary articles according to the invention preferably contain a material according to the present invention, in particular in one of the preferred variants described herein.
  • At least one layer comprises an absorbent non-woven fabric or a porous polymer which is impregnated with a solution or suspension comprising one or more compounds of formula I (to be used) according to the invention and/or one or more physiologically acceptable salts thereof, and preferably comprises one or more additional other active substances (such as skin-soothing and/or skin-moisturizing agents).
  • HPLC analysis of crude extracts prepared from 20 ml samples taken under sterile conditions and extracted with equal amounts of ethyl acetate served as a means of detection and estimation of glycolipids.
  • the ethyl acetate extracts are dried over anhydrous sodium sulfate, evaporated to dryness, re-dissolved in 2-propanol and analyzed using the HPLC systems described below in HPLC-MS methods “fermentation control”.
  • Dacryopinax spathularia was propagated in a series of 500 ml shake flask batches containing each 200 ml of culture media as described above (Example 1B) under “a) Shake flask cultures (including “Seed cultures). During fermentation, samples were taken, and pH, mycelial dry weight, amount of extractable material and biological activities of crude ethyl acetate extracts of the culture broth against Bacillus subtilis and Zygosaccharomyces bailii in the agar diffusion assay were determined.
  • the fermentation was performed in a 3001 fermentor (Bioengineering Type P, equipped with four Ekato Intermig® impellers) containing 200 l of GM2 medium, sterilized under steam for 45 min at 121° C., inoculated with the above described 20 l seed culture.
  • a 3001 fermentor Bioengineering Type P, equipped with four Ekato Intermig® impellers
  • GM2 medium 200 l of GM2 medium
  • 0.03 ml/l of Clarol FBA 3003K (Cognis, Monheim, Germany) as anti-foam agent were added; no additional supply of antifoam was necessary during fermentation.
  • the fermentation was performed at ca. 33° C., under agitation (75 rpm) and aeration (0.2 vvm). The fermentation was stopped after 300 h when the free glucose had almost been consumed and the oxygen partial pressure had dropped to 20%.
  • the cultures from 10 shake flasks were harvested.
  • the culture fluid was separated by filtration from the mycelia.
  • the wet mycelia were extracted two times with equal volumes of acetone for each 30 min in an ultrasonic bath. This acetone was evaporated in vacuo at 40° C. and the remaining aqueous phase was diluted to 700 ml with water. This phase was extracted three times with equal volumes of ethyl acetate (EtOAc).
  • EtOAc ethyl acetate
  • the culture broth resulting from a 2001 fermentation was alkalized from an initial pH value of 4.5 to pH 8 with 1 N sodium hydroxide solution to allow the glycolipids that partially stick to the cells under acidic conditions to become largely released from the mycelia.
  • the mycelia were separated using a Westfalia KA1-06-525 separator, and in addition the culture broth was filtrated through a Pall (Dreieich Germany) 0.1 ⁇ m polysulfone membrane filter casettes, diameter of fibers 1.4 mm, total area 24 m 2 ) microfiltration system to completely retain the mycelia.
  • the product was sedimented (precipitated) by acidifying the filtrate with 2 N hydrochloric acid to pH 3 and incubating for 16 h under cooling to 11° C.
  • the fluid was removed by decantation and subsequent centrifugation (4500 rpm, 15 min, Typ Jouan SA LR 5.22 (Jouan, Paris France), resulting in a whitish-grey gel.
  • This crude product was washed immediately with water (pH 7), centrifuged again at (4500 rpm for 15 min) and freeze-dried. This process yielded 380 g dry glycolipid which was further characterized by HPLC-MS (see e.g. HPLC chromatogram in FIG. 2 ).
  • the column was equilibrated with ACN/water (1:5) and then eluted using the following conditions at a flow of 20 ml/min: 3:30 min, ACN/water (1:5) isocratic; 9 min, ACN/water (1:1) gradient; 19:00 min, ACN/water (1:1) isocratic; 29:00 min ACN/water (2:1) gradient; 49:00 min ACN/water (2:1) isocratic; 59:00 min pure ACN gradient.
  • the separations were monitored by a diode array detector at 200 and 210 nm. Five ml fractions were taken using an automatic fraction collector and finally combined according to UV absorption (200 and 210 nm), concentrated in vacuo and subjected to HPLC-MS, to assess their purity.
  • Extracts containing compounds of the formula I are defined with their preparation procedures, e.g. the use of the above explained processes.
  • the numbering of the atoms is shown in FIG. 1 .
  • LC-MS/UVELSD analyses were performed using an Agilent HP1100 (Agilent, Waldbronn, Germany) liquid chromatograph coupled with a LCT mass spectrometer (Waters Corporation, Milford, Mass., USA) in the positive and negative electrospray ionization (ESI) mode and a Sedex 75 Evaporative Light Scattering Detector (Sedere, Alfortville Cedex, France).
  • ESI electrospray ionization
  • Sedex 75 Evaporative Light Scattering Detector Sedex 75 Evaporative Light Scattering Detector (Sedere, Alfortville Cedex, France).
  • a Waters symmetry column Waters Symmetry® (Trademark by Waters) C18, 3.5 ⁇ m, 2.1 mm ⁇ 150 mm, Waters GmbH, Eschborn, Germany) was used as stationary phase with a flow rate of 0.4 ml/min at 40° C.
  • Mobile phase A 0.1% formic acid in water
  • mobile phase B 0.1% formic acid in acetonitrile
  • gradient 0-1 min. 98% A, from 1-21 min. to 100% B, from 21-27 min 100% B.
  • the UVN is spectra were recorded between 200-500 nm
  • the LC-MS (Liquid Chromatography-Mass Spectrometry coupling) spectra were recorded in the range of molecular weights between 160 and 1.600 Da.
  • LC-MS/UVELSD analyses were performed using an Agilent HP1100 (Agilent, Waldbronn, Germany) liquid chromatograph coupled with a LCT mass spectrometer (Waters Corporation, Milford, Mass., USA) in the positive and negative electrospray ionization (ESI) mode and a Sedex 75 Evaporative Light Scattering Detector (Sedere, Alfortville Cedex, France).
  • ESI electrospray ionization
  • Sedex 75 Evaporative Light Scattering Detector Sedex 75 Evaporative Light Scattering Detector (Sedere, Alfortville Cedex, France).
  • a Waters symmetry column Waters Symmetry® (Trademark by Waters) C18, 3.5 ⁇ m, 2.1 mm ⁇ 150 mm, Waters GmbH, Eschborn, Germany) was used as stationary phase with a flow rate of 0.4 ml/min at 40° C.
  • Mobile phase A 0.1% formic acid in water
  • mobile phase B 0.1% formic acid in acetonitrile
  • the UV/Vis spectra were recorded between 200-500 nm
  • the LC-MS (Liquid Chromatography-Mass Spectrometry coupling) spectra were recorded in the range of molecular weights between 160 and 1.600 Da.
  • HPLC system Agilent 1100 analytical HPLC system including pumps and autosampler, DAD (200-500 nm) and ELSD detectors; column oven at 40° C.; column: Waters Symmetry® C18 3.5 ⁇ m (2.1 ⁇ 150 mm); solvents: deionised water (A) and acetonitrile (B) with 0.1% formic acid each. The flow was adjusted to 0.4 ml/min by using a temperature of 40° C. The gradient applied was optimized for separation and resolution of the glycolipid pattern: 0 to 14 min: from 45% to 100% (B); 14 to 16 min: 100% (B); 16 to 16.1 min: from 100% to 45% (B); 16.1 to 20 min: 45% (B).
  • samples were dissolved in 2-propanol.
  • Saccharomyces cerevisiae strain HT10 and Mucor plumbeus were originally taken from the culture collection of InterMed Discovery GmbH but deposited with MUCL as reference strains for antimicrobial susceptibility testing. These strains were maintained under liquid nitrogen and, prior to the screening, on YMG agar.
  • the yeast and bacterial strains Prior to the screening the yeast and bacterial strains were grown over night on SDB (medium 1), except for Bacillus subtilis , which was grown on YMG agar (medium 2) for 1 week to prepare spore suspensions. Likewise, the filamentous fungi were pre-incubated on YMG agar for 2-3 weeks to create inoculum for spore suspensions. The spores were then rinsed from the surface of the flasks using 0.9% saline, checked for viability by microscopic control and by plating on agar plates, and diluted to the desired concentration of spores. For all experiments, freshly prepared spore suspensions were used. The initial concentrations for the bioassays were adjusted to 1 ⁇ 10 5 CFU (i.e. cells or spores, respectively) per ml. Standards (preservative agents benzoic acid and sorbic acid; antibiotics: penicillin G, streptomycin sulphate, amphopthericin B) served as
  • the CFU per ml was determined under the microscope using a counting chamber type “Brand Neubauer improved”; BRAND GmbH & Co KG, Wertheim, Germany). This microscopic control also served as means for assessment of the viability of the cells.
  • each microtiter plate vial was filled with 200 ⁇ l of the cell suspensions and the test plates were incubated in an incubator (Heraeus HERA cell) at 28° C. an absolute humidity of 95%, to prevent evaporation of the solvent. Under such conditions, no notable evaporation of the microtiter plates was observed for up to several weeks.
  • MICs were generally determined in a traditional manner, by checking the MTP optically and determining the dilution of each individual compound where no visible growth had occurred.
  • the OD 630 was also determined using a plate reader, in those cases where it appeared difficult to observe the MIC with the naked eye. In some instances, the OD 630 of the plates could be monitored and determined using the plate reader for up to four weeks. However, in general, the long term experiments were run for at least 168 hours.
  • OD 630 For determination of OD 630 , the microtiter plates were scanned using a SPECTROstar Omega (BMG LABTECH, Offenburg, Germany) plate reader, except for the filamentous fungi, where a PHERAstar plus (BMG LABTECH, Offenburg, Germany) plate reader was used in “Wellscan” mode (orbital averaging at 4 mm), since this instrument provided more reliable data if mycelial colonies had arisen from the initial spore suspensions. MIC in the optical readout was determined using the following formula:
  • the MIC values reported relate to the concentration causing at least 80% inhibition as compared to the positive control.
  • plumbeus 25 50 12.5 25 >100 25 12.5 50 50 100 25 25 >100 >100 50 >100 Yeast
  • D. bruxellensis (DSM70726) 2 12.5 12.5 6.3 25 >100 3.1 3.1 7 25 25 12.5 25 >100 12.5 6.3 16 25 25 12.5 50 >100 100 6.3 28 25 25 25 50 >100 100 6.3
  • D. naardenensis 2 (DSM70743) 12.5 100 12.5 25 50 3.1 3.1 25 7 25 12.5 25 >100 50 6.3 100 1 25 50 12.5 25 >100 >100 6.3 28 25 >100 12.5 25 >100 >100 6.3 B.
  • plumbeus 2 7.8 7.8 7.8 15.6 62.5 7.8 (MUCL49355) 7 15.6 15.6 15.6 31.3 125 15.6 16 15.6 31.3 31.3 31.3 >500 31.3 28 62.5 31.3 62.5 125 >500 250 Yeast D. naardenensis 2 7.8 ⁇ 3.9 7.8 7.8 125 7.8 (DSM70743) 7 7.8 7.8 15.6 15.6 500 15.6 16 7.8 7.8 15.6 15.6 >500 31.3 28 7.8 15.6 15.6 15.6 >500 15.6 B.
  • bailii (DSM70492) 2 6.3 3.1 3.1 3.1 ⁇ 3.9 ⁇ 3.9 >500 ⁇ 3.9 31.3 ⁇ 3.9 apple juice 7 6.3 3.1 6.3 ⁇ 3.9 ⁇ 3.9 >500 ⁇ 3.9 31.3 ⁇ 3.9 16 6.3 3.1 3.1 3.1 ⁇ 3.9 ⁇ 3.9 ⁇ 3.9 31.3 ⁇ 3.9 28 6.3 3.1 3.1 3.1 ⁇ 3.9 ⁇ 3.9 ⁇ 3.9 31.3 ⁇ 3.9 D.
  • Apple juice medium per se shows already limited growth which is based mainly on the low concentration of nitrogen compounds available and needed for growth.
  • Bacillus subtilis Clostridium perfringens (ATCC13124) Corynebacterium variabile (DSM20132) Corynebacterium variabile (ATCC15753) Escherichia coli (ATCC9637) Lactobacillus plantarum (DSM12028) Pseudomonas putida (ATCC17484) Staphylococcus aureus (ATCC 6538P)
  • Aspergillus fumigatus Aspergillus fumigatus (ATCC1028) Aspergillus niger (ATCC16404) Byssochlamys fulva (DSM62097) Mucor plumbeus (MUCL49355)
  • DSM70726 Dekkera bruxellensis (DSM70726) Dekkera naardenensis (DSM70743) Saccharomyces cerevisiae (HT10) Zygosaccharomyces bailii (DSM70492) Zygosaccharomyces bailii (ATCC60484) Zygosaccharomyces bisporus (DSM70415) Zygosaccharomyces florentinus (DSM70506) Zygosaccharomyces rouxii (NCYC381)
  • the average mol weight was set to 1000 g/mol, the presented data in the following table 22 are given in mg/ml (ppm).
  • the extract [X2] was dissolved in water to final concentrations of 10 ppm and 100 ppm. These two test samples were presented together with a pure water sample (as negative control) to two test persons. The three samples were blinded prior to the taste evaluation.
  • test persons were able to discriminate between pure water and the sample containing 10 ppm of the test compound.
  • the sample containing 100 ppm of the test compound was described with a diffuse taste comparable with water which was stored for a longer time in an open PET bottle. No bitter, spicy or otherwise unpleasant taste was observed.
  • a 2% fruit juice based non-carbonated beverage of pH 3.4 and about 12 Brix is formed by combining the following ingredients.
  • a pH of 3.4 is achieved through combinations of malic acid and sodium malate.
  • the total combined quantity of sodium malate and malic acid is near constant, but the ratio of malic acid and malate varied slightly depending on the content of compound extract [X2].
  • the culture broth resulting from the 301 fermentation of Example 8A) b) was alkalized from an initial pH value of 4.5 to a pH value of 8 with 5 N sodium hydroxide solution to allow the glycolipids that partially stick to the cells under acidic conditions to become largely released from the mycelia. After 1 h the mycelia were separated from the culture broth by centrifugation, and then the culture broth was filtrated additionally through a Pall T1000 depth filter (Dreieich, Germany) to remove cell clusters and filamentous material. The product was sedimented (precipitated) by acidifying the filtrate with 6 N hydrochloric acid to pH 2.2 and subsequent storing for 20 h at 4° C.
  • the fluid was removed by decantation, subsequent centrifugation (4500 rpm, 15 min, Type Jouan SA LR 5.22 (Jouan, Paris, France) and then discarded, resulting in a whitish-grey gel.
  • This crude product was washed immediately with 11 of slightly basic demineralized water (set to a pH-value of 8 with sodium hydroxide) and centrifuged at (4500 rpm for 15 min). The supernatant was removed and the remaining pellet suspended in 0.5 l demineralized water.
  • the culture broth resulting from the 301 fermentation of Example 8A) b) was alkalized from an initial pH value of 4.5 to a pH value of 8 with 5 N sodium hydroxide solution to allow the glycolipids that partially stick to the cells under acidic conditions to become largely released from the mycelia. After 1 h the mycelia were separated from the culture broth in a separator, and then the culture broth was pumped through a combined filter assembly: first though a depth filter with a pore size of 0.65 ⁇ m and then through a membrane filter with a pore size of 0.45 ⁇ m to remove not only filamentous material and cell clusters but also cells.
  • the product was sedimented (precipitated) by acidifying the filtrate with 6 N hydrochloric acid to pH 2 and then stored for 16 h at 4° C.
  • the fluid was removed by decantation, subsequent centrifugation (4500 rpm, 15 min, Type Jouan SA LR 5.22 (Jouan, Paris, France) and then discarded, resulting in a whitish-grey gel.
  • This crude product was washed immediately with 1 l demineralized water and centrifuged at (4500 rpm for 15 min). The supernatant was removed, the remainder suspended in 0.5 l demineralized water and the pH adjusted to a pH value of about 6 with 5 N sodium hydroxide solution.
  • HPLC-MS analyses were performed using a Dionex Ultimate® 3000 RSLC (Thermo Fisher GmbH, Idstein; Germany) liquid chromatograph coupled with a amaZon SL ion trap mass spectrometer (Bruker Daltonik GmbH, Bremen, Germany) in the negative electrospray ionization (ESI) mode and a Sedex 85 ELSD (Sedere, Alfortville Cedex, France).
  • ESI electrospray ionization
  • Sedex 85 ELSD Sedex 85 ELSD
  • a Nucleoshell RP18 column (2.7 ⁇ m, 2 mm ⁇ 150 mm, Macherey-Nagel GmbH & Co. KG, Düren, Germany) was used as stationary phase with a flow rate of 0.4 ml/min at 40° C.
  • Mobile phase A 0.1% formic acid in water
  • mobile phase B 0.1% formic acid in acetonitrile
  • the LC-MS (Liquid Chromatography-Mass Spectrometry coupling) spectra were recorded in the range of molecular weights between 700 and 1.200 Da.
  • a 1 l Erlenmeyer flask containing 400 ml of sterilized medium (2.0% D-glucose, 0.5% malt extract) was inoculated with 2 ml of the secondary seed culture from Example 8A a).
  • the production culture was grown on a rotary shaker at (200 rpm) at 32° C. for 360 h.
  • a 1 l Erlenmeyer flask containing 400 ml of sterilized medium (4.0% D-glucose, 0.2% yeast extract) was inoculated with 6 ml of the secondary seed culture from Example 8A a).
  • the production culture was grown on a rotary shaker at (200 rpm) at 32° C. for 240 h.
  • Tables 25-27 represent the corresponding MIC values of several pure compounds after 48 h against various microorganisms.
  • beverage compositions A and C each were carbonated with 3.8 volumes of carbon dioxide after filling into bottles.
  • beverage compositions B and D each were carbonated with 3.0 volumes of carbon dioxide after filling into bottles.
  • the beverage compositions A and C each were carbonated with 4 volumes of carbon dioxide after filling into bottles.
  • the beverage composition B was carbonated with 2 volumes of carbon dioxide after filling into bottles.
  • Skimmed milk and whole milk were mixed in proportions to give milk with 1.1% fat, then 5 wt. % of sucrose were added thereto, and heated to 82° C. for 30 minutes. After cooling to 42° C., 0.7% of a commercially available starter culture of Bifidobacterium bifidum and 0.5% of a starter culture of Streptococcus thermophilus culture were added, and the mixture cultured at 39° C. until the pH-value of the mixture reached 4.4. The resulting firm yoghurt curd was then broken by stirring, and split in two portions (portion A and portion B).
  • LiqYog A To stirred portion A were added 0.4 wt. % (based on the mass of firm yoghurt) of high methoxyl citrus pectin as 5 wt. % solution in water and the mixture cooled with stirring to 5° C. This product was then passed through a sterilized homogenizer at 40 bar to give a liquid yoghurt having a dynamic viscosity of 380 mPas at 10° C. Thereto were first added with stirring 45 ppm of the extract [X7] of Example 8B-1), and then 9.0 wt. % of a pasteurized peach pulp, in both cases based on the total weight of the liquid yoghurt. The resulting mixture was homogenized giving LiqYog A which was transferred into a glass container, and stored at 7° C. for 10 days.
  • LiqYog B To stirred portion B were added 0.6 wt. % (based on the mass of firm yoghurt) of high methoxyl apple pectin as 5 wt. % solution in water and the mixture cooled with stirring to 5° C. This product was then passed through a sterilized homogenizer at 15 bar to give a liquid yoghurt having a dynamic viscosity of 600 mPas at 10° C. Thereto were first added with stirring 95 ppm of the extract [X8] of Example 8D), and then 7.5 wt. % of a pasteurized strawberry-blueberry puree, in both cases based on the total weight of the liquid yoghurt. The resulting mixture was homogenized giving LiqYog B which was stored at 8° C. before further processing.
  • a B C Ingredient in wt. % in wt. % in wt. % in wt. % Ethanol (96% in water) 8.00 5.00 — Glycerin 8.00 10.00 12.00 1,2-Propylene Glycol — — 2.00 Sodium Fluoride 0.05 0.13 0.10 Poloxamer 407 (Pluronic F-127 ®, 1.40 — 0.60 BASF) PEG-40 hydrogenated castor oil and — 1.00 0.50 propylene glycol (Cremophor ® CO 40, BASF) Sodium Phosphate buffer (pH 7.0) 1.10 — 1.00 Blue colorant (1% in water) 0.10 0.05 — Red colorant (1% in water) — 0.05 0.08 Sorbic acid 0.025 — — Benzoic acid 0.025 — — 4-Hydroxybenzoic acid methylester — — 0.06 Na Salt Sodium Saccharinate 0.10 — 0.12 Sorbitol (70%
  • Perfume oil P1 Perfume oil P2 Ingredient parts by weight parts by weight Acetophenone, 10% in DPG 10.00 — n-Undecanal 15.00 5.00 Allylamylglycolate, 20.00 — 10% in DPG Amylsalicylate 25.00 15.00 Benzyl acetate 60.00 40.00 Citronellol 80.00 50.00 D-Limonen 60.00 10.00 Dihydromyrcenol 60.00 15.00 Eucalyptus oil 10.00 — Geraniol 40.00 60.00 Nerol 20.00 20.00 Geranium oil 15.00 15.00 Hexenol cis-3, 10% in DPG 5.00 15.00 Hexenyl salicylate cis-3 20.00 — Indole, 10% in DPG 10.00 — Alpha-Ionone 15.00 15.00 Vanillin 5.00 — Lilial (2-methyl-3-(4-tert- 60.00 — butyl-phenyl)propanal) Linalool 40.00 60.00 Methylphenyl a
  • a B C Ingredient in wt. % in wt. % in wt. % PEG-40 Stearate 5.00 4.00 5.50 Ethylhexylglycerin 1.00 1.20 — (Octoxyglycerin) Cetyl Alcohol 2.00 1.00 1.70 Stearyl Alcohol — 1.00 0.50 Mineral oil 2.00 2.00 2.00 Aluminum Hydrochlorate powder — 8.00 15.00 Polysorbate 80 0.80 1.00 1.20 Glycerin 2.50 1.50 1.50 Mg-Aluminium Silicate 0.80 0.80 0.80 Talc 1.50 — — 1,2-Pentandiol — — 0.60 1,2-Octandiol — 0.75 0.20 2-Benzyl heptanol — 0.10 — 2-Methyl-4-phenyl-2-butanol — 0.10 0.30 4-Methoxybenzyl alcohol 0.10 — — 4-Methyl-4-phenyl-2-pentanol 0.05 — 0.10 Extract [
  • a B C Ingredient in wt. % in wt. % in wt. % Glycerin Isostearate 1.80 2.00 1.80 Octoxyglycerin — 0.80 0.90 Ceteareth-15 5.25 5.50 5.00 Isotridecyl Isononanoate 3.30 3.50 3.80 Cyclomethicon 6.80 6.40 6.00 L-Menthyl-L-Lactate — 0.20 0.10 Octyldodecanol — 0.40 — Aluminium Chlorohydrate — 5.00 9.00 Triclosan ® — — 0.25 Extract [X7] of 0.0012 — 0.0004
  • a B C Ingredient in wt. % in wt. % in wt. % C 10-30 Alkyl acrylate crosspolymer 0.60 0.60 0.60 Sodium Hydroxide, 15% in water 0.10 0.12 0.10 Disodium EDTA 0.10 0.10 0.10 1,2-Decandiol 1.00 0.50 1.00 1,2-Dodecandiol — 0.70 — 1-Tetradecanol — — 0.50 Glycol Distearate, Laureth-4, 3.00 3.00 3.00 3.00 Cocamidopropyl Betaine Sodium Laureth Sulfate (SLES), 12.00 14.00 10.00 53% in water Sodium Cocamphoacetate 5.00 5.00 7.00 Ammonium Cocoyl Isethionate 10.00 8.00 9.00 Acetamide MEA 1.00 1.50 0.50 Palmitamide MEA 0.50 — 0.50 Phenoxyethanol — 0.70 0.30 Extract [X7] of 0.0015 — 0.0003 Example 8 B-1) Extract [X8] of
  • a B C Ingredient in wt. % in wt. % in wt. % Polyquaternium-7 0.50 0.50 0.65 Disodium Phenyl Dibenzimidazole 0.50 — — Tetrasulfonate Butyl Methoxydibenzoylmethane (Avobenzone) 0.25 — 0.80 Phenylbenzimidazole Sulfonic Acid, Sodium 0.80 1.00 1.20 Salt Amino Methyl Propanol 0.50 0.60 0.40 Sodium Laureth Sulfate (SLES), 28% in water 30.00 25.00 20.00 Cocoamidopropyl Betaine 5.00 6.00 7.50 Propylene Glycol, PEG-55 Propylene Glycol 0.80 0.80 0.80 Dioleate Panthenol 1.00 0.40 — Allantoin — 0.25 0.50 Methylparaben, Ethylparaben, — 0.30 0.55 Butylparaben, Propylparaben, Iso
  • a B C D Ingredient in wt. % in wt. % in wt. % in wt. % in wt. % Ceterayl isononanoate, Ceterareth-20, Stearyl 3.00 — — 2.50 alcohol, Glyceryl stearate, Glycerin, Ceterareth-21, Cetyl palmitate Mineral oil 3.00 — 3.00 — Paraffinum liquidum — — 4.00 — Ethylhexyl ethylhexanoate — — 5.00 — Cetearyl ethylhexanoate — — 3.50 — PEG-40 Hydrogenated castor oil, Trideceth-9, — 2.00 — — Propylene glycol, water Citric acid, anhydrous — 0.01 — — Vitamin E Acetate (Tocopheryl Acetate) 0.10 — — 0.08 Phenoxyethanol 0.40 — — 0.10 Imidazolinyl urea
  • a B C D Ingredient in wt. % in wt. % in wt. % in wt. % in wt. % Sodium chloride 1.25 2.10 2.60 1.50 Zinc chloride 0.50 0.50 — 0.25 Glycerin 1.00 1.30 0.50 1.50 1,2-Butylene glycol — 0.40 0.80 — DMDM Hydantoin — 0.10 — 0.10 Phenoxyethanol — — 0.40 — Imidazolinyl urea 0.10 — — 0.05 Cyclodextrins — 0.15 — 0.20 Acyl Glutamate 1.00 — 0.90 1.10 (surfactant) Dimethiconol and TEA 0.70 0.50 0.60 0.80 Dodecylbenzene sulfonate PEG-75 Lanolin 0.25 0.75 0.50 0.60 Polysorbate 20 0.22 0.40 0.30 0.50 Malic acid 0.05 0.07 0.10 0.10 Extract [X7] of 0.0008 — 0.0002
  • a B C D Ingredient in wt. % in wt. % in wt. % in wt. % in wt. % Paraffin oil 5.00 5.00 5.00 Isopropyl palmitate 5.00 5.00 5.00 Cetyl alcohol 2.00 — 1.00 2.00 Stearyl alcohol — 2.00 1.00 — Beeswax 2.00 2.00 1.00 2.00 Ceteareth-20 2.00 2.00 2.00 2.00 PEG-20-glyceryl stearate 1.50 1.50 1.50 1.50 Glycerine 3.00 3.00 4.00 2.00 1,2-Butylene glycol/ — 0.50 — 1.50 1,2-Propylene glycol (1:1) Phenoxyethanol — 0.25 — 0.15 Extract [X7] of 0.001 — 0.0004 0.0007 Example 8 B-1) Extract [X8] of — 0.0005 0.0006 — Example 8 D) Perfume oil P1 according 0.75 0.10 0.45 — to Example 14 Perfume oil P2 according
  • a B C Ingredient in wt. % in wt. % in wt. % Glyceryl Oleate Citrate, Caprylic/Capric Triglyceride 2.00 — 2.00 Potassium Cetyl Phosphate — 1.50 — Cetearyl alcohol — 1.00 — C12-15 - Alkyl Benzoate — 2.50 — Homosalate 5.00 2.00 5.00 Butyl Methoxydibenzoylmethane (Avobenzone) 3.00 3.00 3.00 3.00 Ethylhexyl Salicylate 3.00 4.00 3.00 Octocrylene — 5.50 — Isoamyl p-Methoxycinnamate — 3.00 — Diisopropyl Adipate 6.00 — 6.00 Ethylhexyl Isononanoate — 2.00 — Diethylhexyl 2,6 Naphthalate 1.50 — 2.00 Disodium EDTA 0.10 0.10 0.10 Vitamin
  • compositions A and C are sunsprays
  • composition B is a sunscreen softcream.
  • a clear liquid composition having a pH-value of 5.6 was prepared consisting of 2-propanol (45 wt. %), 1-propanol (30 wt. %), lactic acid (0.3 wt. %), 1-tetradecanol, medium chain triglycerides, glycerol, sodium lactate, extract [X7] of Example 8B-1) (25 ppm), and water.
  • a clear liquid composition having a pH-value of 5.3 was prepared consisting of 1-propanol (40 wt. %), 2-propanol (28 wt. %), citric acid (0.2 wt. %), lactic acid (0.15 wt. %), 1-dodecanol, medium chain triglycerides, glycerol, 1,2-propylene glycol, extract [X8] of Example 8D) (45 ppm), and water.
  • a composition was prepared consisting of ethanol (55 wt. %), 1-propanol (10 wt. %), 1,2-propylene glycol (6 wt. %), 1,3-butylene glycol, lactic acid, extract [X8] of Example 8D) (15 ppm), and water.
  • a B C D Ingredient in wt. % in wt. % in wt. % in wt. % in wt. % Benzalkonium chloride 2.00 2.50 0.10 0.15 Cocopropylenediamine guanidinium acetate 14.00 14.00 0.25 — Phenoxypropanol 35.00 30.00 0.50 — Tetrakis-(2-hydroxypropyl)-N,N,N′,N′- 5.00 — 0.08 — ethylenediamine Disodium EDTA — 1.00 0.10 0.05 Laurylpropylenediamine — 4.50 — 0.10 Maleic acid 0.45 0.15 0.02 0.01 Citric acid — 0.25 — 0.01 Tridecyl ethoxylate-12EO 15.00 — 0.15 0.05 Tridecyl ethoxylate-5EO — 10.00 0.10 0.20 Ethanol 8.00 10.00 0.25 0.20 1-Propanol 1.00 — — 0.10 Extract [X7] of 0.10
  • a B C D Ingredient in wt. % in wt. % in wt. % in wt. % in wt. % Benzalkonium chloride 0.20 0.05 — — Ethylhexylglycerin (Octoxyglycerin) 0.25 0.20 0.25 — Octenidine dihydrochloride — 0.07 — 0.10 Laureth-35 0.02 — 0.01 — Sodium gluconate — 0.40 — 0.30 Glycerol 2.10 2.50 1.50 3.00 Mecetroniumetilsulfate — — 0.15 — Phenoxypropanol — — — 1.00 Cocoamidopropyl betaine — 0.30 0.25 — 2-Propanol 0.50 — — 0.45 Extract [X7] of 0.002 — 0.0006 0.0007

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US10758460B2 (en) 2016-09-14 2020-09-01 Kaneka Corporation Gel-like composition, and external-use agent for skin and cosmetic material in which said gel-like composition is used
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US20220232837A1 (en) * 2021-01-27 2022-07-28 Christopher Francais Ruvalcaba Composition for Sterilization of Tree Cutting Devices and a Method of Use Thereof
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US11975084B2 (en) 2022-02-17 2024-05-07 Kao Usa Inc. Composition for application to a surface of skin of a user
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