EP3709820A1 - Mélanges à activité antimicrobienne - Google Patents

Mélanges à activité antimicrobienne

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Publication number
EP3709820A1
EP3709820A1 EP17808019.8A EP17808019A EP3709820A1 EP 3709820 A1 EP3709820 A1 EP 3709820A1 EP 17808019 A EP17808019 A EP 17808019A EP 3709820 A1 EP3709820 A1 EP 3709820A1
Authority
EP
European Patent Office
Prior art keywords
mixture
acid
antimicrobial
component
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP17808019.8A
Other languages
German (de)
English (en)
Inventor
Kathrin Langer
Margit LIEBIG
Johannes KIEFL
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Symrise AG
Original Assignee
Symrise AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Symrise AG filed Critical Symrise AG
Publication of EP3709820A1 publication Critical patent/EP3709820A1/fr
Pending legal-status Critical Current

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Classifications

    • 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
    • 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
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2028—Carboxy compounds
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/84—Flavour masking or reducing agents
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/86—Addition of bitterness inhibitors
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/88—Taste or flavour enhancing agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/45—Ericaceae or Vacciniaceae (Heath or Blueberry family), e.g. blueberry, cranberry or bilberry
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine

Definitions

  • the present invention is in the field of antimicrobial agents.
  • the present invention also relates to preparations containing such mixtures, in particular nutrition or pleasure or pharmaceutical preparations, and to processes for producing such preparations and processes for the antimicrobial treatment of nutrition or pleasure or pharmaceutical preparations , Further aspects of the present invention will become apparent from the following statements and in particular the appended claims.
  • Foods particularly those of animal origin (such as mayonnaise, minced meat and sausage products) and sugary foods (such as sweetened beverages, syrups, ketchup and dressing) are susceptible to microbial spoilage due to their nutrient richness and high water activity coefficient (aw).
  • animal origin such as mayonnaise, minced meat and sausage products
  • sugary foods such as sweetened beverages, syrups, ketchup and dressing
  • yeasts and fungi can grow even at pH values below 3 and lead to spoilage.
  • Special yeasts such as Zygosaccharomyces baili, Zygosaccharomyces lentus and Saccharomyces cerevisiae also display tolerance to preservatives such as sorbic acid and benzoic acid [Steels, H., James, S.A., Roberts, I.N. and Stratford, M. (1999).
  • Antibiotic-resistant bacteria prevalence in food and inactivation by food-compatible compounds and plant extracts. J Agric Food Chem 63 (15): 3805-3822].
  • herbs, spices and the essential oils and extracts derived from them have a proven action against bacteria [Weber, H. (2010). Microbiology of Foods - Basics. Hamburg, Behrs Verlag], but these change the taste in an unacceptable way with their own characteristics in many products.
  • Plant extracts with antimicrobial activity against yeasts and fungi are only a few known, and their use in foods is often limited because of their strong intrinsic aromatics, strong coloring properties and poor solubility.
  • formulations to be provided should preferably also be toxicologically safe, well tolerated, stable (in particular in customary formulations) and / or inexpensive to produce.
  • the primary object is achieved by the use of a mixture comprising or consisting of
  • A one or more antimicrobially active plant extract (s) and / or one or more antimicrobially active fraction (s) thereof, selected from the group consisting of extracts from plants of the following families: Asparagaceae, Cannabaceae, Ericaceae, Lythraceae, Krameriaceae, Rosaceae , and Vitaceae, preferably from the following plants: Humulus lupulus, Fragaria x anapassa, Krameria lappacea, Punica granatum, Vaccinium angustifolium, Vaccinium macrocarpon, Vaccinium myrtillus, Vaccinium vitis-idaea, Vitis vinifera, and fractions thereof,
  • Flavoring agent selected from the group consisting of abrusosides and balansines (preferably as described in WO 2012 164,062), malic acid, benzaldehyde, gamma-decalactone, delta-decalactone, 3,7'-dihydroxy-4'-methoxyflavane isomers ( preferably as described in EP 2,253,226), eriodictyol, ethyl 2-methylbutyrate, ethyl butyrate, ethylcapronate, geranial, hesperetin (preferably as described in WO 2007/014879, EP 2,368,442-B1 or EP 1,909,599-B1), or extract
  • the one or more antimicrobially active plant extract (s) according to (A) and / or the one or more fraction (s) thereof according to one embodiment of the present invention preferably the root and / or the fruiting organs of the plant or parts thereof used, preferably endo-, meso-, Exokarp and / or parts of the inflorescence.
  • the substance (s) according to (B) or constituents thereof according to one embodiment of the present invention may likewise be in the form of an extract / in an extract or in the form of a fraction thereof / in a fraction thereof, preferably selected from the group consisting of extracts ( or fractions thereof) from the following plants: Artemisia xanthochroa, Artemisia dracunculus, Bauhinia manca, Chenopodium album, Chysothamnus ssp., Citrus ssp.
  • component (B) enhances the antimicrobial efficacy of component (A) (synergistic antimicrobial effect; ie, the antimicrobial efficacy of the mixture exceeds the sum of the antimicrobial efficacy (s) of the mixture contained antimicrobially active substances), which advantageously allows to manage with low (re) n amounts of antimicrobial substances in the mixture, and / or reduces, disguises or modifies an unpleasant taste impression of ingredient (A), and / or enhances or modifies a pleasing taste impression of ingredient (A).
  • component (B) is contained in a total amount in a mixture to be used according to the invention, which is sufficient to enhance the antimicrobial activity of the component (A) and / or to reduce an unpleasant taste impression of the component (A) to mask or modify and / or enhance or modify a pleasing flavor impression of ingredient (A).
  • the taste impressions to be reduced, masked or modified are preferably selected from the group consisting of astringent, bitter, herbaceous, metallic, acidic.
  • the flavor impressions to be enhanced or modified are preferably selected from the group consisting of sweet, juicy and full-bodied.
  • the mixtures to be used according to the invention are outstandingly suitable as antimicrobial active ingredient mixtures for prolonging the shelf life of perishable preparations.
  • mixtures to be used according to the invention also allow the initially mentioned specifications to be met.
  • the invention is based on the surprising finding that the mixtures according to the invention have a particularly advantageous antimicrobial effect, in particular against on fungi or yeasts, show, in particular against one or more germs selected from the group consisting of
  • Aureobasidium sp. Alternaria alternata, Aspergillus brasiliensis, Aspergillus fumigatus, Cladosporium sp., Fusarium sp. Rhodotorula sp., Sporidiobolus sp., Sporobolomyces sp., Paecilomyces sp. and Penicillium sp.
  • Particularly preferred - and advantageous - is therefore a use according to the invention against fungi or yeasts, preferably against one, several or all germs selected from the group consisting of S. cerevisiae, Z. bailii, C. albicans, A. pullulans and A. brasiliensis ,
  • the extract (s) of the component (A) is / are selected from the group consisting of berry extracts, preferably extracts of red berries, pomegranate extracts and herbal extracts.
  • the extracts for component (A) can be prepared from whole plants, parts of plants, biotechnologically modified or unchanged plant materials, with customary methods known to the person skilled in the art can be used, preferably solid-liquid extractions. Furthermore, enrichment / concentration of selected substances can also take place after extraction, if necessary.
  • Moist plant parts can be extracted with the assistance of microwave radiation, ultrasound and pulsed electric field.
  • Fractionation of the extracts is preferably carried out by separation of undesired minor components and / or concentration of selected substances, for example by adsorption, distillation, chromatographic separation, fermentation, filtration, liquid-liquid extraction, membrane filtration and / or centrifugation, preferably by chromatographic separation, liquid-liquid extraction and / or membrane filtration.
  • the constituents of the respective fractions can be determined if necessary by known methods.
  • component (A) comprises at least one, two, three or more compound (s) selected from the group consisting of catechins, chlorogenic acid, p-coumaric acid, epicatechins, ellagic acid, gallic acid, caffeic acid, sinapinic acid and cinnamic acid.
  • compound (s) selected from the group consisting of catechins, chlorogenic acid, p-coumaric acid, epicatechins, ellagic acid, gallic acid, caffeic acid, sinapinic acid and cinnamic acid.
  • the concentration ratios in particular of the substances catechins, chlorogenic acid, p-coumaric acid, epicatechins, ellagic acid, gallic acid, caffeic acid, sinapinic acid and / or cinnamic acid, can be deliberately changed to the other constituents by the fractionation.
  • a change is preferably carried out in a manner improving the antimicrobial effect.
  • constituent (B) comprises at least one, two, three or more flavoring agents selected from the group consisting of eriodictyol, hesperetin, homoeriodictyol, naringenin, pellitorin and vanillic acid, or consists thereof.
  • the ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1000: 1 to 1:10, preferably 100: 1 to 1:10, preferably in the range of 100: 1 to 1: 1, preferably 10: 1 to 1: 1, is located.
  • the amount (s) of any components attributable to both component (A) and component (B) be assigned to the total amount of component (A).
  • the mixtures described herein are particularly well suited for use in a nutrition or pleasure preparation or pharmaceutical preparation.
  • the present invention also relates to a nutrition or pleasure preparation or pharmaceutical preparation comprising a mixture as described herein, wherein the mixture is contained in an amount sufficient to provide an antimicrobial effect, preferably a synergistic antimicrobial effect to achieve.
  • the mixture be contained in an amount sufficient to provide an antimicrobial effect, preferably a synergistic antimicrobial activity, against one or more of the germs selected from the group consisting of
  • Aureobasidium sp. Alternaria alternata, Aspergillus brasiliensis, Aspergillus fumigatus, Cladosporium sp., Fusarium sp. Rhodotorula sp., Sporidiobolus sp., Sporobolomyces sp., Paecilomyces sp. and Penicillium sp.
  • the mixture is contained in an amount sufficient to provide an antimicrobial effect, preferably a synergistic antimicrobial effect, against one, several or all of the germs selected from the group consisting of S. cerevisiae, Z. bailii, C. albicans, A. pullulans and A. brasiliensis.
  • Preparations according to the invention are particularly preferably foods, in particular those with ingredients of animal origin (such as mayonnaise, minced meat preparations and sausages) and also sugary foods (such as sweetened beverages, syrups, ketchup and dressings).
  • ingredients of animal origin such as mayonnaise, minced meat preparations and sausages
  • sugary foods such as sweetened beverages, syrups, ketchup and dressings
  • a mixture to be used according to the invention is used in a preparation which is selected from the group consisting of foods, preferably foods with ingredients of animal origin, for example mayonnaise, minced meat preparations and sausages, sugar-containing foods, for example sweetened drinks, syrups, seasoning sauces, for example ketchup, salad creams and dressings.
  • foods preferably foods with ingredients of animal origin, for example mayonnaise, minced meat preparations and sausages, sugar-containing foods, for example sweetened drinks, syrups, seasoning sauces, for example ketchup, salad creams and dressings.
  • a mixture to be used in accordance with the invention may be used herein as e.g. in a total amount of 3 to 0.001, preferably from 0.5 to 0.01, particularly preferably from 0.1 to 0.01 wt .-%, based on the total weight of the preparation, be contained.
  • a mixture to be used according to the invention may be used for these purposes e.g. in the form of a liquid preparation or powder or spray-dried product in such preparations.
  • components (A) and (B) are mixed and dissolved, added in liquid or spray-dried form, but components (A) and (B) can also be used separately and in a different form.
  • the preparations according to the invention moreover preferably consist of constituents customary for such preparations. For example, solvents or carriers may be included.
  • the solvents may be, for example, water, ethanol, 1, 2-propanediol, triacetin, diacetin, triethyl citrate and / or glycerol.
  • Advantageous carriers are, for example, silicon dioxide (silica, silica gel), carbohydrates and / or carbohydrate polymers (polysaccharides), cyclodextrins, starches, degraded starches (starch hydrolysates), chemically or physically modified starches, modified celluloses, gum arabic, ghatti gum, tragacanth, karaya, Carrageenan, guar gum, locust bean gum, alginates, pectin, inulin or xanthan gum; Preferred starch hydrolysates are maltodextrins and dextrins, with maltodextrins having DE values in the range from 5 to 20 being particularly preferred.
  • starch hydrolysates It is irrelevant which plant originally supplied the starch for the preparation of the starch hydrolysates. Suitable and readily available are corn-based starches and starches from tapioca, rice, wheat or potatoes.
  • the carriers can also act as flow aids, such as silica.
  • One aspect of the present invention also relates to a method for producing a preparation according to the invention, comprising or consisting of the following steps:
  • a method according to the invention for the antimicrobial treatment of a preparation for nutrition or pleasure preferably as described above, or a pharmaceutical preparation comprising or consisting of the following steps:
  • Aureobasidium sp. Alternaria alternata, Aspergillus brasiliensis, Aspergillus fumigatus, Cladosporium sp., Fusarium sp. Rhodotorula sp., Sporidiobolus sp., Sporobolomyces sp., Paecilomyces sp. and penicillium sp., more preferably an antimicrobial action, preferably a synergistic antimicrobial activity against one, several or all of the germs selected from the group consisting of S. cerevisiae, Z. bailii, C. albicans, A pullulans and A. brasiliensis.
  • a pomegranate peel extract is made by halving and squeezing pomegranates and then homogenizing the remainder of the peel with 50 ° C water. The mash is then squeezed. The resulting extract (filtrate) is then concentrated by distillation.
  • the resulting concentrated extract contains i.a. following components:
  • a membrane filtration For a subsequent production of individual fractions of the concentrated extract, for example, a membrane filtration can be used.
  • a flat membrane based on polyethylene glycol with a membrane area of 26 cm 2 and a cutoff of 2500 Da was rinsed twice with ultrapure water at 30 bar for 20 minutes.
  • a 1% extract solution 200 g was introduced, heated to 30 ° C and applied with 30 bar pressure.
  • After passage of 138.23 g was rediluted with 100 g of water and filtered again.
  • the membrane filtrates were freeze-dried and a permeate of 16.8% and a retentate of 65.8% yield were obtained.
  • the resulting fractions were then analyzed by mass spectrometry for their constituents.
  • the resulting fractions contain, inter alia, the following nonvolatile constituents:
  • An extract is prepared by macerating fruits of Vaccinium macrocarpon, Vaccinium angustifolium and Fragaria x anapassa, followed by a filtrate Pressing is won. Subsequently, the filtrate (extract) is concentrated by distillation.
  • the resulting concentrated extract contains i.a. following components:
  • An extract is made by first grinding grape seeds. Then it is extracted with water at 50 ° C and filtered to obtain the extract. Subsequently, the extract obtained is concentrated by distillation.
  • the resulting concentrated extract contains i.a. following components:
  • a polyethylene glycol-based flat membrane with a membrane area of 26 cm 2 and a cutoff of 2500 Da was rinsed twice with ultrapure water at 30 bar for 20 minutes.
  • a 1% extract solution 200 g was introduced, heated to 30 ° C and applied with 30 bar pressure. After passage of 138.23 g was rediluted with 100 g of water and filtered again.
  • the membrane filtrates were freeze-dried and a permeate of 7.6% and a retentate of 58.8% yield were obtained.
  • a polar and a nonpolar fraction can be obtained, e.g. by means of chromatographic methods.
  • a solution of 100 mg grape seed extract in 1 mL of deionized water was prepared and pre-conditioned with water / ethanol (90/10) preparative HPLC (PRP-1 column 250x21, 5 mm, 10 pm particle size ) Column at a flow rate of 10 mL / minute.
  • the eluent used was deionized water and ethanol (99.5%) at an oven temperature (60 ° C isotherm). It was first eluted for 25 minutes with water / ethanol (90/10). Thereafter, the ethanol content increased by ten percentage points to 20% within ten minutes and was held constant for ten minutes. The ethanol content was then increased to 100% within five minutes and held for five minutes.
  • the polar fraction was run for 10 to 36 minutes and the nonpolar fraction was trapped for 37 to 55 minutes. The yield of the polar fraction was 48% and the nonpolar fraction 28%.
  • the resulting fractions were then mass spectrometrically examined for their constituents.
  • the resulting fractions contain i.a. the following non-volatile constituents:
  • exemplary extracts were used as described in Examples 1 to 3.
  • the extracts were dissolved in citrate buffer at pH 3 at 500 mg / kg.
  • Samples were inoculated with 5.63 x 10 4 cfu / mL S. cerivisiae, 1.89 x 10 4 Z. bailii, and 3.75 x 10 4 C. albicans. Number of cfu / mL by day
  • A. pullulans could be reduced during the 28 days. For GRA, even a 100% reduction was observed after 28 days.
  • A. brasiliensis could be detected after 28 days with lower numbers of bacteria.
  • the antimicrobial efficacy of the extracts can be improved by combination with a component (B) described herein.
  • exemplary extracts or fractions thereof were used as described in Examples 1 and 4.
  • the extracts or fractions thereof were dissolved in phosphate buffer at pH 5 according to the dosage indicated in the table.
  • the samples were inoculated with 3.8 x 10 4 CFU / mL S. cerevisiae.
  • the negative control did not lead to a significant reduction in the number of bacteria.
  • the antimicrobial efficacy of the extracts can be improved by combination with a component (B) described herein.
  • the content of limonene of lemon oils is between 70% and 1%. 7. Examples of use:
  • mixtures or combinations to be used according to the invention can be used in a large number of formulations.
  • the extract contains 8.3 g / kg ellagic acid and 4.7 g / kg gallic acid
  • the extract contains 8.3 g / kg ellagic acid and 4.7 g / kg gallic acid

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Meat, Egg Or Seafood Products (AREA)
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  • Non-Alcoholic Beverages (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne le domaine des principes actifs antimicrobiens. Outre de nouvelles utilisations selon l'invention de mélanges antimicrobiens déterminés, la présente invention concerne des préparations contenant de tels mélanges, en particulier des préparations destinées à l'alimentation ou au plaisir gustatif ou des préparations pharmaceutiques, ainsi que des procédés pour produire de telles préparations et des procédés de traitement antimicrobien de préparations destinées à l'alimentation ou au plaisir gustatif ou de préparations pharmaceutiques.
EP17808019.8A 2017-11-14 2017-11-14 Mélanges à activité antimicrobienne Pending EP3709820A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2017/079115 WO2019096363A1 (fr) 2017-11-14 2017-11-14 Mélanges à activité antimicrobienne

Publications (1)

Publication Number Publication Date
EP3709820A1 true EP3709820A1 (fr) 2020-09-23

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CN111328261A (zh) 2020-06-23
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US11925194B2 (en) 2024-03-12
US20200397026A1 (en) 2020-12-24

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