CN116725013A - Use of antibacterial compounds for inhibiting vibrio, antibacterial and detergent compositions - Google Patents

Use of antibacterial compounds for inhibiting vibrio, antibacterial and detergent compositions Download PDF

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Publication number
CN116725013A
CN116725013A CN202310701950.6A CN202310701950A CN116725013A CN 116725013 A CN116725013 A CN 116725013A CN 202310701950 A CN202310701950 A CN 202310701950A CN 116725013 A CN116725013 A CN 116725013A
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citrate
formula
vibrio
composition
bacteriostatic
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张迷敏
张利萍
黄亮
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Guangzhou Liby Enterprise Group Co Ltd
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Guangzhou Liby Enterprise Group Co Ltd
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00Disinfectants; Antimicrobial compounds or mixtures thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2075Carboxylic acids-salts thereof
    • C11D3/2079Monocarboxylic acids-salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2075Carboxylic acids-salts thereof
    • C11D3/2086Hydroxy carboxylic acids-salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2093Esters; Carbonates
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Detergent Compositions (AREA)

Abstract

The invention provides an application of a bacteriostatic compound in vibrio inhibition, a bacteriostatic and washing composition, and relates to the technical field of bacteriostatic compounds. The compound used for inhibiting the vibrio is natural in source, is a non-antibiotic, and has very effective inhibition effect on the vibrio. The composition for inhibiting vibrio contains 0.005-0.1% of the antibacterial compound and 0.005-0.5% of citrate, and the antibacterial effect of the antibacterial compound is further enhanced by the citrate, so that the technical blank of the fruit and vegetable tableware detergent and the hand cleaner in the aspect of inhibiting the growth of vibrio is filled.

Description

Use of antibacterial compounds for inhibiting vibrio, antibacterial and detergent compositions
Technical Field
The invention relates to the technical field of antibacterial compounds, in particular to an application of an antibacterial compound in inhibiting vibrio, and an antibacterial and washing composition.
Background
Vibrio (Vibrio bacteria) widely inhabits aquatic and marine environments, and can cause seafood fish pollution and cause the occurrence of human infectious diseases. Internationally recognized pathogenic vibrio includes 11 human pathogens such as vibrio cholerae (v.cholerae), vibrio meyenikovii (v.metschnikovii), vibrio parahaemolyticus (v.parahaemeolyticus), and vibrio vulnificus (v.vulnificus). Due to the problem of overuse of antibiotics in recent years, the presence of a variety of microbial non-degradable antibiotics has been found in aquatic environments, which can lead to the development of vibrio resistance in humans and aquatic organisms.
The appearance of antibiotic drug-resistant pathogenic vibrio can seriously threaten human health, and serious symptoms such as abdominal pain, diarrhea, hemolysis and the like can be caused even death by carelessly using tableware polluted by the bacteria or eating polluted foods such as fish, seafood, vegetables and fruits and the like. However, the current fruit and vegetable tableware washing industry and food industry pay attention to the aspects of sterilization and bacteriostasis mainly including escherichia coli, staphylococcus aureus, salmonella and the like, and lack of sufficient importance and effective preventive measures for pathogenic vibrio infection and health problems caused by the pathogenic vibrio infection.
In recent years, the reports of vibrio infection caused by eating foods polluted by pathogenic vibrio and causing serious gastrointestinal diseases, hemolysis and other symptoms are increasing year by year, so that development of a novel antibacterial agent which is superior to broad-spectrum antibiotics and can be safely and effectively applied to the fruit and vegetable tableware washing industry and the food seasoning industry is needed to inhibit the growth and reproduction of pathogenic vibrio, thereby reducing the risk of vibrio oral infection. And the compound/compound composition which is not antibiotics and has the characteristic of biodegradability and is natural trend of development of degerming and bacteriostasis products, and has wide market application prospect.
In view of this, the present invention has been made.
Disclosure of Invention
The first object of the invention is to provide an application of antibacterial compounds in inhibiting vibrio, wherein the antibacterial compounds are natural in source and are non-antibiotics, and have an effective inhibiting effect on the vibrio.
A second object of the present invention is to provide a composition for inhibiting vibrio, which further enhances the bacteriostatic action of bacteriostatic compounds by citrate.
A third object of the present invention is to provide a detergent composition which alleviates the problem of the prior art of lacking a detergent product having an inhibitory effect on vibrio.
A fourth object of the present invention is to provide the use of the above antibacterial compound, the above vibrio-inhibiting composition or the above washing composition.
In order to solve the technical problems, the invention adopts the following technical scheme:
according to one aspect of the present invention there is provided the use of a bacteriostatic compound of formula (I) for the inhibition of Vibrio;
wherein R is 1 Is OH or OCH 3 ,R 2 Is H or OH, R 3 H or OH.
Preferably, the vibrio comprises at least one of vibrio vulnificus and vibrio alginolyticus;
preferably, in formula (I), R 1 Is OH, R 2 Is H, R 3 The antibacterial compound of the formula (I) is H, and the antibacterial compound of the formula (I) is cinnamic acid;
preferably, in said application, the working concentration of said bacteriostatic compound of formula (i) is between 0.005% and 0.1%, preferably between 0.01% and 0.1%, even more preferably 0.05%.
Preferably, in said application the bacteriostatic compound of formula (i) is used in combination with citrate;
preferably, the citrate salt comprises one or more of sodium citrate, sodium dihydrogen citrate, potassium citrate and ammonium citrate;
preferably, in said application, the working concentration of said citrate is between 0.005% and 0.5%, preferably between 0.01% and 0.5%, further preferably 0.1%.
According to one aspect of the present invention, there is also provided a composition for inhibiting vibrio comprising a bacteriostatic compound of formula (i) and citrate;
wherein R is 1 Is OH or OCH 3 ,R 2 Is H or OH, R 3 Is H or OH;
the working concentration of the antibacterial compound in the formula (I) in the composition is 0.005-0.1%, and the working concentration of citrate is 0.005-0.5%.
According to one aspect of the present invention there is also provided a cleaning composition comprising (a) or (b), and a cleaning component;
(a) Antibacterial compounds of formula (i):
wherein R is 1 Is OH or OCH 3 ,R 2 Is H or OH, R 3 H or OH.
(b) The above composition for inhibiting vibrio.
According to an aspect of the present invention, there is also provided the above vibrio-inhibiting composition, or the use of the above detergent composition, in at least one of:
preparing a bacteriostatic agent; (ii) preparing a cleaning agent; (iii) preparing a bacteriostatic drug; (iv) inhibiting vibrio for non-diagnostic and therapeutic purposes; (v) at least one of fruit and vegetable cleaning, dish cleaning, and hand cleaning.
According to an aspect of the present invention, there is also provided a bacteriostatic product comprising a bacteriostatic agent, a detergent or a bacteriostatic drug, the bacteriostatic product comprising the above composition for inhibiting vibrio or the above washing composition.
Compared with the prior art, the invention has the following beneficial effects:
the antibacterial compound shown in the formula (I) is derived from a plant extract, is a non-antibiotic antibacterial compound, can effectively inhibit the growth of vibrio under a lower concentration through practical verification, and has the effect of further enhancing the effect of inhibiting the vibrio after being combined with citrate. Based on the discovery that the composition and the washing composition for inhibiting the vibrio have the effect of inhibiting the vibrio, the antibacterial compound, the composition for inhibiting the vibrio and the washing composition are applied to antibacterial agents and cleaning agents, and the technical blank of the fruit and vegetable tableware cleaning agent and the hand cleaning agent in the aspect of inhibiting the growth of the vibrio is filled.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are needed in the description of the embodiments or the prior art will be briefly described, and it is obvious that the drawings in the description below are some embodiments of the present invention, and other drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
FIG. 1 shows the inhibitory effect of the washing composition with/without cinnamon extract of effect example 1 of the present invention on the growth of Vibrio vulnificus;
FIG. 2 shows the inhibitory effect of the washing composition with/without cinnamon extract of effect example 1 of the present invention on the growth of Vibrio alginolyticus;
FIG. 3 shows the inhibitory effect of the detergent for cinnamon extract-citrate complex with/without addition of the detergent for cinnamon extract-citrate complex in effect example 2 of the present invention on the growth of Vibrio vulnificus;
FIG. 4 shows the inhibitory effect of the detergent for cinnamon extract-citrate complex with/without addition of the detergent for cinnamon extract-citrate complex on the growth of Vibrio alginolyticus in effect example 2 of the present invention;
FIG. 5 shows the inhibitory effects of cinnamic acid and rosemary extract, respectively, on growth of Vibrio alginolyticus in effect example 3 of the invention.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in connection with the embodiments, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
It should be understood that the terms "comprises" and "comprising," when used in this specification and the appended claims, specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof.
It is also to be understood that the terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used in this specification and the appended claims, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It should be further understood that the term "and/or" as used in the present specification and the appended claims refers to any and all possible combinations of one or more of the associated listed items, and includes such combinations.
All percentages, fractions and ratios are by weight of the total composition of the present invention, unless otherwise specified.
All weights as they pertain to listed ingredients are to the active level and, therefore, do not include solvents or by-products that may be included in commercially available materials, unless otherwise specified. Herein, "%" means weight percent.
According to one aspect of the present invention, there is provided the use of a bacteriostatic compound for inhibiting vibrio, said bacteriostatic compound being of formula (i);
wherein R is 1 Is OH or OCH 3 ,R 2 Is H or OH, R 3 H or OH.
In the application provided by the invention, the antibacterial compound is derived from a plant extract and is a non-antibiotic antibacterial compound. In practical application, the invention is not limited to the source of the compound shown in the formula (I), and the compound can be a compound extracted from plants, a compound which is obtained through chemical synthesis and is in accordance with the formula (I), or a compound which is obtained through plant extraction and further manual processing.
In an alternative embodiment, in formula (I), R 1 Is OH, R 2 Is H, R 3 And H is H, and the antibacterial compound of the formula (I) is cinnamic acid.
In an alternative embodiment, the vibrio comprises at least one of vibrio vulnificus and vibrio alginolyticus. Experiments prove that the vibrio including vibrio vulnificus and vibrio alginolyticus can be effectively inhibited as shown in the formula (I).
In alternative embodiments, the working concentration of the bacteriostatic compound of formula (i) in the application is 0.005% to 0.1%, such as but not limited to 0.005%, 0.01%, 0.02%, 0.03%, 0.04%, 0.05%, 0.06%, 0.07%, 0.08%, 0.09% or 0.1%, or a range between any two of the above, preferably 0.01% to 0.1%, more preferably 0.05%.
In an alternative embodiment, the antibacterial compound of formula (i) and the citrate are used in combination, and experiments show that the citrate has a synergistic effect on inhibiting vibrio by the antibacterial compound of formula (i), and the inhibition effect of the antibacterial compound of formula (i) and the citrate on the vibrio by the combination is superior to that of the antibacterial compound of formula (i) alone.
The citrate salt used in combination with the bacteriostatic compound of formula (i) may be selected from citrate salts conventional in the art, including, but not limited to, one or more of sodium citrate, sodium dihydrogen citrate, potassium citrate and ammonium citrate. In alternative embodiments, the working concentration of citrate in the application may be, for example, but not limited to, 0.005%, 0.01%, 0.05%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%, or a range between any two of the above, preferably 0.01% to 0.5%, and more preferably 0.1%.
Based on the foregoing, the antibacterial compound of formula (I) and citric acidThe present invention also provides a vibrio-inhibiting composition comprising the antibacterial compound of formula (I) and a citrate salt. In an alternative embodiment, in formula (I), R 1 Is OH, R 2 Is H, R 3 And H is H, and the antibacterial compound of the formula (I) is cinnamic acid. The citrate salt may be selected from citrate salts conventional in the art including, but not limited to, one or more of sodium citrate, sodium dihydrogen citrate, potassium citrate, and ammonium citrate. In an alternative embodiment, the citrate salt comprises sodium citrate.
In the antibacterial composition provided by the invention, the working concentration of the antibacterial compound of the formula (I) is 0.005% -0.1%, for example, but not limited to, 0.005%, 0.01%, 0.02%, 0.03%, 0.04%, 0.05%, 0.06%, 0.07%, 0.08%, 0.09% or 0.1%, or a range between any two points. The working concentration of citrate is 0.005% to 0.5%, for example but not limited to 0.005%, 0.01%, 0.05%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5% or a range between any two of the above.
In an alternative embodiment, the working concentration of the antibacterial compound of formula (I) in the vibrio-inhibiting composition is 0.01% to 0.1%, and the working concentration of citrate is 0.01% to 0.5%.
In an alternative embodiment, the working concentration of the bacteriostatic compound of formula (I) in the vibrio-inhibiting composition is 0.05% and the working concentration of citrate is 0.1%.
According to one aspect of the present invention there is provided a cleaning composition comprising (a) or (b), and a cleaning component;
(a) Antibacterial compounds of formula (I) above:
(b) The vibrio-inhibiting composition of the foregoing embodiment.
In alternative embodiments, the cleaning component includes components conventional in the art for cleaning, which the present invention is not limited to, including but not limited to at least one of surfactants, solvents, enzymes, polymers, and adjuvants; in the following embodiments, 0% means that the component is not contained.
In alternative embodiments, the polymer may be present in an amount of 0% to 5%, such as, but not limited to, 0.1%, 0.5%, 1%, 2%, 3%, 4% or 5%, or in a range between any two of the foregoing. The polymer is acceptable in the washing field, optionally a polymer such as, but not limited to, a polymer for rheology modifiers, anti-redeposition agents, optical brighteners or phosphorus-substituted adjuvants. Specific examples of the polymer include, but are not limited to, hydroxyethyl cellulose, carboxymethyl cellulose, polyacrylate, polyurethane, polyacrylate, methylcellulose ether, polycarboxylate, sodium tripolyphosphate, or methyl maleate-methacrylate copolymer, etc., to which the present invention is not limited.
In alternative embodiments, the surfactant comprises one or a mixture of cationic, nonionic and anionic surfactants, preferably cationic and/or nonionic surfactants. In alternative embodiments, the anionic surfactant includes, but is not limited to, one or a combination of carboxylate, sulfonate, sulfate, and phosphate; in alternative embodiments, the cationic surfactant comprises one or a combination of several of quaternary ammonium surfactants, heterocyclic surfactants, polymeric cationic surfactants; in alternative embodiments, the nonionic surfactant includes, but is not limited to, one or a combination of fatty alcohol alkoxylates, fatty acid methyl ester ethoxylates, alkyl polyglycosides, fatty acid alkyl alcohol amides, and ethoxylated sorbitan esters.
In alternative embodiments, the surfactant may be present in the cleaning composition in an amount of from 0% to 15%, for example but not limited to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14% or 15%, or in a range between any two of the foregoing.
In alternative embodiments, when the cationic surfactant is included in the cleaning composition, the concentration of cationic surfactant is not more than 10%, such as, but not limited to, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9% or 10%, or a range between any two of the foregoing.
In alternative embodiments, the solvent includes, but is not limited to, monopropylene glycol and/or methylpropanediol;
in alternative embodiments, the solvent may be present in an amount of 0% to 15%, such as, but not limited to, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14% or 15%, or a range between any two of the foregoing.
In alternative embodiments, the enzymes include, but are not limited to, one or a combination of proteases, amylases, cellulases, lipases, mannanases, pectinases, pectin lyases, and xanthanases.
In alternative embodiments, the enzyme may be present in an amount of 0% to 0.5%, such as, but not limited to, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%, or in a range between any two of the foregoing.
In alternative embodiments, the adjuvant comprises one or a combination of a plurality of cosolvents, pH stabilizers and fragrances.
In an alternative embodiment, the detergent composition is as shown in table 1 and comprises a surfactant, a solvent and other components, wherein 0% means no corresponding components, but it is noted that the detergent composition described in table 1 comprises at least one surfactant, at least one solvent and at least one other component. The substrate may be selected from substrates conventional in the art for use in washing components, such as water.
TABLE 1
In an alternative embodiment, the wash component comprises 8% fatty alcohol polyoxyethylene ether, 2% sodium alkylbenzenesulfonate, 2% alkyl glucoside, 2% propylene glycol, 0.01% sodium chloride, and 0.1% perfume.
In an alternative embodiment, the wash composition is water-based.
In an alternative embodiment, the above-described cleaning composition is prepared as follows: dissolving or dispersing the antibacterial compound of formula (I) or the antibacterial compound of formula (I) and citrate in a proper amount of water respectively to obtain mother solution with higher concentration; the surfactant is dissolved in water, then the rest of components are added, then the antibacterial compound of the formula (I) or the antibacterial compound of the formula (I) and citrate mother liquor are added, and then a proper amount of water is added for uniform dispersion.
In alternative embodiments, the cleaning composition comprises 0.005% to 0.1% of the antibacterial compound of formula (i) above, for example but not limited to 0.005%, 0.01%, 0.02%, 0.03%, 0.04%, 0.05%, 0.06%, 0.07%, 0.08%, 0.09% or 0.1%, or a range between any two of the above; or, including the antibacterial compound of formula (i) above, for example, but not limited to, 0.005%, 0.01%, 0.02%, 0.03%, 0.04%, 0.05%, 0.06%, 0.07%, 0.08%, 0.09% or 0.1%, or a range between any two of the above, and citrate 0.005% to 0.5%, for example, but not limited to, 0.005%, 0.01%, 0.05%, 0.1%, 0.2%, 0.3%, 0.4% or 0.5%, or a range between any two of the above.
In alternative embodiments, the cleaning composition comprises 0.01% to 0.1% of the antibacterial compound of formula (I) above, or comprises 0.01% to 0.1% of the antibacterial compound of formula (I) above and 0.01% to 0.5% of citrate.
In alternative embodiments, the cleaning composition comprises 0.05% of the antibacterial compound of formula (I) above, or comprises 0.01% to 0.1% of the antibacterial compound of formula (I) above and 0.1% of citrate.
In an alternative embodiment, the bacteriostatic compound of formula (i) is cinnamic acid.
In an alternative embodiment, the citrate is sodium citrate.
According to another aspect of the present invention, there is also provided the above vibrio-inhibiting composition, or the use of the above detergent composition, in at least one of:
preparing a bacteriostatic agent; (ii) preparing a cleaning agent; (iii) preparing a bacteriostatic drug; (iv) inhibiting vibrio for non-diagnostic and therapeutic purposes; (v) at least one of fruit and vegetable cleaning, dish cleaning, and hand cleaning.
According to another aspect of the present invention, there is also provided a bacteriostatic product comprising a bacteriostatic agent, a detergent or a bacteriostatic drug, which comprises the above composition for inhibiting vibrio or the above washing composition. The antibacterial product also comprises optional auxiliary materials acceptable in the corresponding field according to the specific type, for example, when the antibacterial product is a cleaning agent or a antibacterial agent, the antibacterial product also comprises the auxiliary materials acceptable in the field of daily chemicals. In alternative embodiments, the cleaning agent is a fruit and vegetable cleaning agent or a hand cleaning agent. When the bacteriostatic product is a bacteriostatic drug, it may optionally include optional excipients acceptable in the pharmaceutical arts, including but not limited to one or more of excipients, solvents, diluents, pH modifying agents, preservatives, humectants, and pro-solvents, etc.
The invention is further illustrated by the following specific examples, however, it should be understood that these examples are for the purpose of illustration only in greater detail and are not to be construed as limiting the invention in any way.
The pathogenic vibrio in the following embodiments are vibrio alginolyticus (Vibrio alginolyticus) and vibrio vulnificus (Vibrio vulnificus).
Example 1
This example provides a detergent composition comprising a model detergent composition and Cinnamic Acid (CA). The composition of the model washing composition is shown in Table 2, and the cinnamic acid content is 0.05%.
TABLE 2
Material name Content/%
Fatty alcohol polyoxyethylene ether 8
Sodium alkylbenzenesulfonate 2
Alkyl glucosides 2
Propylene glycol 2
Sodium chloride 0.01
Essence 0.1
Substrate Supplement to 100
Example 2
The present example provides a detergent composition comprising a model detergent composition, cinnamic Acid (CA) and sodium citrate. The composition of the model washing composition is shown in Table 2, and the cinnamic acid content is 0.05% and the citrate content is 0.1%.
Example 3
The present example provides a detergent composition comprising a model detergent composition, cinnamic Acid (CA) and sodium citrate. The composition of the model washing composition is shown in Table 2, and the cinnamic acid content is 0.005% and the citrate content is 0.5%.
Example 4
The present example provides a detergent composition comprising a model detergent composition, cinnamic Acid (CA) and sodium citrate. The composition of the model washing composition is shown in Table 2, and the cinnamic acid content is 0.1% and the citrate content is 0.005%.
Example 5
This example provides a detergent composition comprising a pattern detergent composition having a composition as shown in table 2 and Rosmarinic Acid (RA) at a level of 0.05%. Rosmarinic acid is shown as formula (II):
wherein R is 1 Is C 9 O 5 H 8 ,R 2 Is OH, R 3 Is OH.
Comparative example 1:
this comparative example provides a detergent composition comprising only a pattern detergent composition having the composition shown in table 2.
Comparative example 2
This comparative example provides a detergent composition comprising a model detergent composition having a citrate content of 0.1% and sodium citrate, the composition of which is shown in table 2.
Effect example
The method for evaluating the effect of inhibiting the growth of Vibrio in the following effect examples is as follows:
1. respectively inoculating vibrio vulnificus and vibrio alginolyticus into Marine broth medium (MB culture medium) liquid culture medium, culturing at 37 ℃ until OD600 = 0.6-0.8, adding glycerol (glycerol final concentration 50%) according to a volume ratio of 1:1, packaging every 10 mu L into a freezing tube, packaging, and rapidly freezing in liquid nitrogen to obtain the vibrio vulnificus frozen stock solution capable of being stored and used for a long time.
2. Evaluation experiment of Vibrio inhibition growth effect: taking 10 mu L of the frozen stock solution, re-dissolving in water bath at 30 ℃, adding the re-dissolved solution into 5ml of MB liquid culture medium containing 0.2-0.5% DMSO, and culturing at 30 ℃ until the OD600 = 0.6-0.8.
3. 10. Mu.L of the culture medium in 2 was inoculated into 5ml of a test sample, and the sample was subjected to shaking treatment at 30℃for 2 hours.
4. 2. Mu.L of the treatment solution in 3 was inoculated to 200. Mu.L of MB medium, and incubated at 30℃to measure the OD600 of the bacteria solution every hour, and each experiment was repeated 3 times.
Calculating the bacteriostasis rate of the object to be detected according to the OD600 value when the microorganism growth reaches the growth stationary phase, wherein the calculation formula is as follows:
exp represents the test group and Con represents the control group.
The MB culture medium comprises the following components: 3.0g/L meat extract, 5.0g/L meat peptone, 10.0g/L sodium chloride, phosphate buffer adjusted to pH 7.0.
Effect example 1
Inhibition effect of detergent with/without cinnamon extract on growth of Vibrio vulnificus and Vibrio alginolyticus:
the test sample formulations were as follows:
example 1 a test sample of the cleaning composition was formulated as follows: cinnamic acid was first prepared as a 0.5% stock solution and 0.5ml of cinnamic acid stock was added to 5ml of MB medium with the remaining components of the detergent composition according to the recipe described in example 1.
Comparative example 1 a test sample of the cleaning composition was formulated as follows: each of the washing composition components of comparative example 1 was added to 5ml of MB medium in the amount of the formulation described in comparative example 1.
And a blank control was set, and the experimental groups were as follows:
TABLE 3 grouping of experiments
Group of MB medium Mode detergent 0.05%CA
Blank control group + - -
Comparative example 1 + + -
Example 1 + + +
Experimental results:
(1) Vibrio vulnificus:
the results show that the washing composition (example 1) added with 0.05% Cinnamic Acid (CA) has a significant inhibitory effect on growth of Vibrio vulnificus. After the treatment with the washing composition of example 1, the growth of Vibrio vulnificus was stably inhibited even after the culture for up to 10 hours. The bacteriostasis rate of the different test samples at 10h incubation time is shown in table 4:
TABLE 4 antibacterial ratio against Vibrio vulnificus after 10h of culture time
Bacteriostasis rate (%)
Blank control group ——
Comparative example 1 ——
Example 1 77.7
The results show that the treatment of comparative example 1 (model washing composition) has no remarkable inhibitory effect on the growth of Vibrio vulnificus, and the inhibition rate on the growth of Vibrio vulnificus is still as high as 77.7% after the treatment of example 1 for 10 hours of culture time.
(2) Vibrio alginolyticus:
the results show that the washing composition (example 1) added with 0.05% Cinnamic Acid (CA) has a remarkable inhibitory effect on growth of Vibrio alginolyticus. After the treatment with the washing composition of example 1, the cultivation time was 0 to 10 hours, and the growth of Vibrio alginolyticus was stably inhibited. The bacteriostasis rates of the different test samples are shown in Table 5 when the incubation time is 10 hours:
TABLE 5 antibacterial ratio against Vibrio alginolyticus after 10h of culture time
Bacteriostasis rate (%)
Blank control group ——
Comparative example 1 ——
Example 1 88.1
The treatment of comparative example 1 (model detergent) had no inhibitory effect on the growth of Vibrio alginolyticus, and after the treatment of example 1, the inhibition rate on the growth of Vibrio alginolyticus was still as high as 88.1% even after 10 hours of cultivation.
Effect example 2
Test samples for inhibition effect of the cinnamon extract-citrate complex on the growth of Vibrio vulnificus and Vibrio alginolyticus were formulated as follows:
the preparation method of comparative example 1 was as described in effect example 1.
Example 2 a test sample of the cleaning composition was formulated as follows: cinnamic acid and sodium citrate were formulated together to give stock concentrations of 0.5% and 1%, respectively, and 0.5ml stock was added to 5ml MB medium with the remainder of the detergent composition in the amounts described in example 2.
Comparative example 2 a test sample of the cleaning composition was formulated as follows: sodium citrate was formulated as a 1% strength stock and 0.5ml stock was added to 5ml MB medium with the remainder of the detergent composition in the amount described in comparative example 2.
And a blank control was set, and the experimental groups were as follows:
TABLE 6 Effect example 2 experimental grouping
Experimental results:
(1) Vibrio vulnificus: the inhibitory effect and inhibition rate of different test samples on the growth of Vibrio vulnificus are shown in FIG. 3 and Table 7, respectively.
The results show that comparative example 2 (mode detergent added with 0.1% of SC) has a certain inhibition effect on Vibrio vulnificus when cultured for 0-6 hours, but after 7 hours, the inhibition effect on Vibrio vulnificus growth is no longer obvious, namely, the inhibition effect of 0.1% of SC on Vibrio vulnificus is not obvious. After the treatment of example 2 (model washing composition added with 0.05% CA-0.1% SC complex), the incubation time was 0 to 10 hours, and the growth of Vibrio vulnificus was stably inhibited. The bacteriostasis rates of the different test samples are shown in Table 7 when the incubation time is 10 hours:
TABLE 7 antibacterial ratio of different test samples to Vibrio vulnificus after 10h of incubation time
Bacteriostasis rate (%)
Blank control group ——
Comparative example 1 ——
Comparative example 2 ——
Example 2 82.5
After the treatment of example 2 (mode detergent added with 0.05% CA-0.1% SC complex), the inhibition rate of the growth of Vibrio vulnificus is 82.5% after 10 hours of culture, which is slightly higher than that of example 1 (77.7%), which shows that the SC has a certain synergistic effect on CA on the antibacterial effect of Vibrio vulnificus.
(2) Vibrio alginolyticus: the inhibitory effect and inhibition rate of the same test sample on the growth of vibrio alginolyticus are shown in fig. 4 and table 8, respectively:
the results show that comparative example 2 (model detergent with 0.1% of SC added) has no remarkable inhibitory effect on the growth of Vibrio alginolyticus, i.e., 0.1% of SC has no remarkable inhibitory effect on Vibrio alginolyticus. After the treatment of example 2 (model detergent added with 0.05% CA-0.1% SC complex), the cultivation time was 0 to 10 hours, and the growth of Vibrio alginolyticus was stably inhibited. The bacteriostasis rates of the different test samples are shown in Table 8 when the incubation time is 10 hours:
TABLE 8 bacteriostasis of different test samples to Vibrio alginolyticus after 10h of incubation time
Group of Bacteriostasis rate (%)
Blank control group ——
Comparative example 1 ——
Comparative example 2 ——
Example 2 88.9
After the treatment of example 2, the inhibition rate of the growth of vibrio alginolyticus was 88.9% after 10 hours of culture, which was not significantly different from that of example 1 (88.1%). The result shows that the antibacterial effect of SC on CA does not show a synergistic effect on Vibrio alginolyticus, unlike the synergistic effect on the antibacterial effect of Vibrio vulnificus.
Effect example 3
Comparing the inhibition effect of Cinnamic Acid (CA) and Rosmarinic Acid (RA) on the growth of vibrio alginolyticus:
the test sample formulations were as follows:
the preparation method of comparative example 1 and example 1 is described in effect examples 1 and 2.
Example 5 a test sample of the cleaning composition was formulated as follows: rosmarinic acid was formulated into a stock at a concentration of 0.5%, and 0.5ml stock was added to 5ml MB medium with the remainder of the detergent composition in the amount prescribed in example 5, and the final concentration of rosmarinic acid was 0.05%.
And a blank control was set, and the experimental groups were as follows:
TABLE 9 Effect example 3 experimental grouping
Group of MB medium Pattern wash compositions 0.05%CA 0.05%RA
Blank control + - - -
Comparative example 1 + + - -
Example 5 + + - +
Example 1 + + + -
Experimental results: the inhibitory effect and inhibition rate of different test samples on the growth of vibrio alginolyticus are shown in fig. 5 and table 10, respectively:
the results show that both example 5 (mode wash composition with 0.05% RA added) and example 1 (mode wash composition with 0.05% ca added) exhibited significant inhibition of growth of vibrio alginolyticus, the bacteriostatic effect of example 1 was due to example 5, and when the incubation time was greater than 7h, the bacteriostatic effect of example 5 was gradually diminished, but the bacteriostatic effect of example 1 was still relatively stable. After treatment with different test samples, the culture was carried out for 10 hours, and the bacteriostasis rate of the growth of Vibrio alginolyticus was shown in Table 10.
TABLE 10 bacteriostasis of different test samples to Vibrio alginolyticus after 10h of incubation time
Bacteriostasis rate (%)
Blank control ——
Comparative example 1 ——
Example 5 67.8
Example 1 87.8
After the treatment of example 1, the inhibition rate of the growth of the vibrio alginolyticus is 87.8 percent after 10 hours of culture, which is obviously higher than 67.8 percent of that of comparative example 1. The application of the cinnamic acid extract and the composition thereof in inhibiting the growth of pathogenic vibrio is obviously superior to that of rosemary extract.
Effect example 4
Test sample preparation referring to effect example 1, the inhibition rates of different test samples on the growth of vibrio alginolyticus/vibrio vulnificus are shown in table 11:
bacteriostasis rate (%)
Example 3 14.5/15.5
Example 4 90.5/90.2
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the invention.

Claims (10)

1. The use of bacteriostatic compounds of formula (I) in the inhibition of Vibrio;
wherein R is 1 Is OH or OCH 3 ,R 2 Is H or OH, R 3 H or OH.
2. The use according to claim 1, wherein the vibrio comprises at least one of vibrio vulnificus and vibrio alginolyticus;
preferably, in formula (I), R 1 Is OH, R 2 Is H, R 3 The antibacterial compound of the formula (I) is H, and the antibacterial compound of the formula (I) is cinnamic acid;
preferably, in said application, the working concentration of said bacteriostatic compound of formula (i) is between 0.005% and 0.1%, preferably between 0.01% and 0.1%, even more preferably 0.05%.
3. Use according to claim 1 or 2, wherein the bacteriostatic compound of formula (i) is used in combination with citrate;
preferably, the citrate salt comprises one or more of sodium citrate, sodium dihydrogen citrate, potassium citrate and ammonium citrate;
preferably, in said application, the working concentration of said citrate is between 0.005% and 0.5%, preferably between 0.01% and 0.5%, further preferably 0.1%.
4. A composition for inhibiting vibrio comprising a bacteriostatic compound of formula (i) and citrate;
wherein R is 1 Is OH or OCH 3 ,R 2 Is H or OH, R 3 Is H or OH;
the working concentration of the antibacterial compound in the formula (I) in the composition is 0.005-0.1%, and the working concentration of citrate is 0.005-0.5%.
5. The composition of claim 4, wherein the citrate salt comprises one or more of sodium citrate, sodium dihydrogen citrate, potassium citrate, and ammonium citrate;
preferably, in formula (I), R 1 Is OH, R 2 Is H, R 3 The antibacterial compound of the formula (I) is H, and the antibacterial compound of the formula (I) is cinnamic acid;
preferably, the working concentration of the antibacterial compound of formula (I) in the composition is 0.01-0.1%, and the working concentration of citrate is 0.01-0.5%;
preferably, the working concentration of the bacteriostatic compound of formula (i) in the composition is 0.05% and the working concentration of citrate is 0.1%.
6. A cleaning composition comprising (a) or (b), and a cleaning component;
(a) Antibacterial compounds of formula (i):
wherein R is 1 Is OH or OCH 3 ,R 2 Is H or OH, R 3 Is H or OH;
(b) The vibrio inhibiting composition of claim 4 or 5.
7. The cleaning composition of claim 6, wherein the cleaning component comprises at least one of a surfactant, a solvent, an enzyme, a polymer, and an adjunct;
preferably, the content of the polymer is 0% -5%;
preferably, the surfactant comprises one or a combination of several of cationic surfactant, nonionic surfactant and anionic surfactant;
preferably, the surfactant comprises a cationic surfactant and/or a nonionic surfactant;
preferably, the anionic surfactant comprises one or a combination of several of carboxylate, sulfonate, sulfate and phosphate;
preferably, the cationic surfactant comprises one or a combination of a plurality of quaternary ammonium salt surfactants, heterocyclic surfactants and polymer cationic surfactants;
preferably, the nonionic surfactant comprises one or a combination of several of fatty alcohol alkoxylates, fatty acid methyl ester ethoxylates, alkyl polyglycosides, fatty acid alkyl alcohol amides and ethoxylated sorbitan esters;
preferably, the content of the surfactant is 0% -15%;
preferably, the content of the cationic surfactant is 0% -10%;
preferably, the solvent comprises monopropylene glycol and/or methylpropanediol;
preferably, the content of the solvent is 0% -15%;
preferably, the enzyme comprises one or a combination of a protease, an amylase, a cellulase, a lipase, a mannanase, a pectinase, a pectin lyase, and a xanthan enzyme;
preferably, the enzyme content is 0% -0.5%;
preferably, the auxiliary agent comprises one or a combination of more than one of a cosolvent, a pH stabilizer and essence;
preferably, the washing component comprises 8% of fatty alcohol polyoxyethylene ether, 2% of sodium alkylbenzenesulfonate, 2% of alkyl glucoside, 2% of propylene glycol, 0.01% of sodium chloride and 0.1% of essence;
preferably, the washing composition is water-based.
8. The cleaning composition of claim 7, wherein the cleaning composition comprises 0.005% to 0.1% of the antibacterial compound of formula (i), or comprises 0.005% to 0.1% of the antibacterial compound of formula (i) and 0.005% to 0.5% of citrate;
preferably, the cleaning composition comprises 0.01% -0.1% of the antibacterial compound of formula (I), or comprises 0.01% -0.1% of the antibacterial compound of formula (I) and 0.01% -0.5% of citrate;
preferably, the cleaning composition comprises 0.05% of the antibacterial compound of formula (I), or comprises 0.01% -0.1% of the antibacterial compound of formula (I) and 0.1% of citrate;
preferably, the bacteriostatic compound of formula (i) is cinnamic acid;
preferably, the citrate is sodium citrate.
9. Use of the composition of claim 4 or 5, or the cleaning composition of any one of claims 6 to 8, in at least one of:
preparing a bacteriostatic agent;
(ii) preparing a cleaning agent;
(iii) preparing a bacteriostatic drug;
(iv) inhibiting vibrio for non-diagnostic and therapeutic purposes;
(v) at least one of fruit and vegetable cleaning, dish cleaning, and hand cleaning.
10. A bacteriostatic product comprising a bacteriostatic, cleaning or bacteriostatic agent, characterized in that it comprises a composition according to claim 4 or 5, or a washing composition according to any one of claims 6 to 8.
CN202310701950.6A 2023-06-13 2023-06-13 Use of antibacterial compounds for inhibiting vibrio, antibacterial and detergent compositions Pending CN116725013A (en)

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