CN116195586A - Composition of myricetin and phloretin, preparation method thereof and application of composition in corrosion prevention - Google Patents
Composition of myricetin and phloretin, preparation method thereof and application of composition in corrosion prevention Download PDFInfo
- Publication number
- CN116195586A CN116195586A CN202210212543.4A CN202210212543A CN116195586A CN 116195586 A CN116195586 A CN 116195586A CN 202210212543 A CN202210212543 A CN 202210212543A CN 116195586 A CN116195586 A CN 116195586A
- Authority
- CN
- China
- Prior art keywords
- myricetin
- phloretin
- concentration
- molar concentration
- bacteriostatic
- 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.)
- Granted
Links
- VGEREEWJJVICBM-UHFFFAOYSA-N phloretin Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=C(O)C=C(O)C=C1O VGEREEWJJVICBM-UHFFFAOYSA-N 0.000 title claims abstract description 162
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical group C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 title claims abstract description 109
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 title claims abstract description 109
- 229940116852 myricetin Drugs 0.000 title claims abstract description 109
- 235000007743 myricetin Nutrition 0.000 title claims abstract description 109
- ZWTDXYUDJYDHJR-UHFFFAOYSA-N (E)-1-(2,4-dihydroxyphenyl)-3-(2,4-dihydroxyphenyl)-2-propen-1-one Natural products OC1=CC(O)=CC=C1C=CC(=O)C1=CC=C(O)C=C1O ZWTDXYUDJYDHJR-UHFFFAOYSA-N 0.000 title claims abstract description 81
- YQHMWTPYORBCMF-UHFFFAOYSA-N Naringenin chalcone Natural products C1=CC(O)=CC=C1C=CC(=O)C1=C(O)C=C(O)C=C1O YQHMWTPYORBCMF-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000005536 corrosion prevention Methods 0.000 title abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 108
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000002904 solvent Substances 0.000 claims abstract description 53
- 239000003814 drug Substances 0.000 claims abstract description 34
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 27
- 230000003385 bacteriostatic effect Effects 0.000 claims abstract description 21
- 235000013305 food Nutrition 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229940079593 drug Drugs 0.000 claims abstract description 14
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 14
- 239000003755 preservative agent Substances 0.000 claims abstract description 13
- 230000002335 preservative effect Effects 0.000 claims abstract description 13
- 241000894006 Bacteria Species 0.000 claims abstract description 12
- 229940123457 Free radical scavenger Drugs 0.000 claims abstract description 3
- 239000000022 bacteriostatic agent Substances 0.000 claims abstract description 3
- 239000002516 radical scavenger Substances 0.000 claims abstract description 3
- 241000588724 Escherichia coli Species 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 13
- 241000191967 Staphylococcus aureus Species 0.000 claims description 10
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 7
- -1 ABTS radicals Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 description 25
- 230000005764 inhibitory process Effects 0.000 description 22
- 230000002195 synergetic effect Effects 0.000 description 18
- 230000001580 bacterial effect Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 7
- 235000010241 potassium sorbate Nutrition 0.000 description 7
- 239000004302 potassium sorbate Substances 0.000 description 7
- 229940069338 potassium sorbate Drugs 0.000 description 7
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241001025319 Etheostoma collis Species 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 235000012055 fruits and vegetables Nutrition 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 230000002000 scavenging effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000003064 anti-oxidating effect Effects 0.000 description 2
- 230000002225 anti-radical effect Effects 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000009631 Broth culture Methods 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000366676 Justicia pectoralis Species 0.000 description 1
- 229940126902 Phlorizin Drugs 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010611 checkerboard assay Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000010794 food waste Substances 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000012803 optimization experiment Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- IOUVKUPGCMBWBT-UHFFFAOYSA-N phloridzosid Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-UHFFFAOYSA-N 0.000 description 1
- IOUVKUPGCMBWBT-GHRYLNIYSA-N phlorizin Chemical compound O[C@@H]1[C@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-GHRYLNIYSA-N 0.000 description 1
- 235000019139 phlorizin Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Images
Classifications
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- 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
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention relates to a composition of myricetin and phloretin, a preparation method thereof and application in corrosion prevention. Specifically discloses a bacteriostatic composition with a preservative effect, which comprises myricetin and phloretin. The composition further comprises at least one solvent selected from DMSO, absolute ethanol, or propylene glycol. In addition, the invention also proves the application of the antibacterial composition in preparing a preservative, and the preservative can be applied to medicines and foods; and bacteriostatic agents for inhibiting bacteria and use as free radical scavengers.
Description
Technical field:
the invention belongs to the field of preservatives, and particularly relates to a composition of myricetin and phloretin, a preparation method thereof and application of the composition in the aspect of preservation.
Background
Food is susceptible to spoilage by microbial infection during processing, storage, transportation and other steps, and food waste caused by food spoilage is immeasurable worldwide each year. The chemically synthesized food preservative has low toxicity to human bodies and risk of causing bacterial drug resistance, and the potassium sorbate and the like widely applied in the market at present have health hidden trouble to human bodies. Searching for safer natural alternatives is becoming a new trend.
Myrican is derived from cortex Myricae Rubrae, and phlorizin is derived from apple peel residue. Both have the characteristics of small toxic and side effect on human bodies and broad-spectrum antibacterial property, and have the possibility of being developed into food antistaling agents. Furthermore, phloretin has been added to foods as a food additive (flavor) and is not used in limited amounts, with certain advantages in the field of preservation.
Disclosure of Invention
The invention provides a formula with synergistic antibacterial effect, which is applied to food fresh-keeping. The research aims to optimize the synergistic antibacterial concentration ratio through the design of a mixing experiment, apply the preservative solution to fresh-cut fruits and vegetables for preserving, and aim to prepare a novel, safe and efficient preservative.
In one aspect, the invention provides a bacteriostatic composition with preservative and anti-free radical activity, which comprises myricetin and phloretin.
Further, the composition further comprises at least one solvent selected from DMSO, absolute ethanol, or propylene glycol.
Further, in the composition, the molar concentration of myricetin and phloretin is 1.3:1-6:1; preferably 1.434:1 to 5.74:1.
In some specific embodiments, in an e.coli bacteriostasis application, the molar concentration of myricetin to phloretin in the composition is from 5.5:1 to 6:1, preferably from 5.7:1 to 5.8:1, e.g., 5.74:1.
In some specific embodiments, in the s.aureus antibacterial application, the molar concentration of myricetin to phloretin in the composition is 1.3:1 to 1.5:1, preferably 1.41:1 to 1.43:1, e.g., 1.434:1.
Further, in the composition, the molar concentration of myricetin is 0.00384mmol/L-39.3mmol/L, and the molar concentration of root Pi Suma is 0.00268mmol/L-6.85mmol/L. Preferably, the molar concentration of myricetin is 0.2456mmol/L-39.3mmol/L and the molar concentration of root Pi Suma is 0.17125mmol/L-6.85mmol/L.
In some specific embodiments, in the antibacterial application against E.coli, the myricetin is in a molar concentration of 3.93mmol/L-39.3mmol/L and the root Pi Suma is in a molar concentration of 0.685mmol-6.85mmol.
In some specific embodiments, in the antibacterial application against E.coli, the myricetin is in a molar concentration of 23.58mmol/L-39.3mmol/L and a root Pi Suma molar concentration of 4.11mmol-6.85mmol in the composition.
In some specific embodiments, in the anti-radical application, the myricetin is present in the composition at a molar concentration of 3.93mmol/L and a root Pi Suma molar concentration of 0.685mmol.
In some specific embodiments, in the bacteriostatic application against S.aureus, the composition has a molar concentration of myricetin of 0.2456mmol/L-2.456mmol/L and a root Pi Suma molar concentration of 0.17125mmol/L-1.7125mmol/L.
In some specific embodiments, in the antibacterial application against S.aureus, the myricetin is present in the composition at a molar concentration of 1.476mmol/L to 2.456mmol/L and a root Pi Suma molar concentration of 1.026mmol/L to 1.7125mmol/L.
In some specific embodiments, in the anti-radical application, the myricetin is present in the composition at a molar concentration of 0.2456mmol/L and at a root Pi Suma molar concentration of 0.17125mmol/L.
Further, the anti-free radical activity and the antibacterial active ingredients in the antibacterial combination consist of myricetin and phloretin.
In another aspect, the present invention provides a method for preparing the antibacterial composition, which comprises the following steps:
the myricetin and phloretin are dispersed in a solvent according to the proportion.
In a further aspect the present invention provides the use of the above-described bacteriostatic composition in the preparation of a preservative.
Further, the preservative is applied to medicines and foods.
Further, the preservative is applied to the fields of non-medicines and non-foods.
In a further aspect, the invention provides the use of a bacteriostatic composition as described above for the preparation of a bacteriostatic agent for inhibiting bacteria.
Further, the bacteria are staphylococcus aureus and escherichia coli.
In a further aspect the present invention provides the use of the above bacteriostatic composition for the preparation of a free radical scavenger.
Further, the radicals are selected from DPPH and ABTS radicals.
The beneficial effects are that:compared with the prior art, the invention has the following remarkable characteristics:
1. the invention discovers that myricetin He Genpi has a synergistic effect in bacteriostasis, can synergistically improve the antioxidation capability, and has potential capability of serving as a preservative for the first time.
2. Aiming at the problem that DMSO has certain toxicity and cannot be used for food or medicine bacteriostasis, the invention specifically screens the solvents which can be used in the food or medicine field, and surprisingly, different solvents can influence the bacteriostasis effect.
Drawings
FIG. 1 is a comparison result of theoretical addition value and actual value of diameters of S.aureus and E.coli inhibition zone of myricetin with different concentrations and phloretin under optimal ratio by using DMSO as solvent in the example.
Wherein A is the result of comparing the theoretical addition value of the diameter of the S.aureus inhibition zone with the actual value under the conditions of 6MIC concentration, 8MIC concentration and 10MIC concentration by taking DMSO as a solvent. Namely, the myricetin concentration is 1.476mmol/L and the phloretin concentration is 1.026mmol/L, the myricetin concentration is 1.968mmol/L and the phloretin concentration is 1.368mmol/L, and the myricetin concentration is 2.46mmol/L and the phloretin concentration is 1.71 mmol/L.
And B is a result of comparing a theoretical addition value of the diameter of the E.coli inhibition zone with an actual value under the conditions of 6MIC concentration, 8MIC concentration and 10MIC concentration by taking DMSO as a solvent. Namely, when the myricetin concentration is compounded with 23.58mmol/L and the phloretin concentration is 4.11mmol/L, and when the myricetin concentration is 31.44mmol/L and the phloretin concentration is 5.48mmol/L, and the myricetin concentration is 39.3mmol/L and the phloretin concentration is 6.85mmol/L, the myricetin is compounded.
Fig. 2 is a comparison result of theoretical addition value and actual value of the diameters of the inhibition zones of S.aureus and E.coli under the optimal ratio of myricetin and phloretin with different concentrations by using propylene glycol as a solvent in example 4.
Wherein A is the result of comparing the theoretical addition value of the diameter of the S.aureus inhibition zone with the actual value under the conditions of 6MIC concentration, 8MIC concentration and 10MIC concentration by taking propylene glycol as a solvent. Namely, the myricetin concentration is 1.476mmol/L and the phloretin concentration is 1.026mmol/L, the myricetin concentration is 1.968mmol/L and the phloretin concentration is 1.368mmol/L, and the myricetin concentration is 2.46mmol/L and the phloretin concentration is 1.71 mmol/L.
And B is a result of comparing a theoretical addition value of the diameter of the E.coli inhibition zone with an actual value under the conditions of 6MIC concentration, 8MIC concentration and 10MIC concentration by taking propylene glycol as a solvent. Namely, when the myricetin concentration is compounded with 23.58mmol/L and the phloretin concentration is 4.11mmol/L, and when the myricetin concentration is 31.44mmol/L and the phloretin concentration is 5.48mmol/L, and the myricetin concentration is 39.3mmol/L and the phloretin concentration is 6.85mmol/L, the myricetin is compounded.
Fig. 3 is a comparison result of theoretical addition value and actual value of the diameters of the inhibition zones of S.aureus and E.colli under the optimal ratio of myricetin and phloretin with different concentrations by using absolute ethyl alcohol as a solvent in example 4.
Wherein A is the result of comparing the theoretical addition value of the diameter of the S.aureus inhibition zone with the actual value under the conditions of 6MIC concentration, 8MIC concentration and 10MIC concentration by taking absolute ethyl alcohol as a solvent. Namely, the myricetin concentration is 1.476mmol/L and the phloretin concentration is 1.026mmol/L, the myricetin concentration is 1.968mmol/L and the phloretin concentration is 1.368mmol/L, and the myricetin concentration is 2.46mmol/L and the phloretin concentration is 1.71 mmol/L.
And B is a result of comparing a theoretical addition value of the diameter of the E.coli inhibition zone with an actual value under the conditions of 6MIC concentration, 8MIC concentration and 10MIC concentration by taking absolute ethyl alcohol as a solvent. Namely, when the myricetin concentration is compounded with 23.58mmol/L and the phloretin concentration is 4.11mmol/L, and when the myricetin concentration is 31.44mmol/L and the phloretin concentration is 5.48mmol/L, and the myricetin concentration is 39.3mmol/L and the phloretin concentration is 6.85mmol/L, the myricetin is compounded.
Fig. 4 is a comparison result of theoretical addition value and actual value of the diameters of the inhibition zones of S.aureus and E.colli under the optimal ratio of myricetin and phloretin with different concentrations by using propylene glycol, DMSO and absolute ethyl alcohol as solvents in example 4.
When the A is propylene glycol, DMSO and absolute ethyl alcohol are used as solvents, the actual values of the diameters of the S.aureus inhibition zone are compared, the concentration of myricetin and phloretin compounded is the same as that of the above (the DMSO, the propylene glycol and the absolute ethyl alcohol are used as solvents), and the actual values of the diameters of the inhibition zone which are used as solvents are put together for comparison, so that the solvent which can replace the DMSO and can be used in foods and has no influence on the antibacterial effect is searched.
And B is the actual value comparison of the diameter of the E.coli inhibition zone when propylene glycol, DMSO and absolute ethyl alcohol are used as solvents.
FIG. 5 shows the clearance of the free radicals DPPH and ABTS from the myricetin and phloretin compositions. Wherein A is the result of comparing the theoretical addition value of the clearance rate of the myricetin to the free radical DPPH with the actual value when the myricetin and the root Pi Sufu, and the Combination1 in the figure represents the Combination of the concentration of the myricetin of 0.2456mmol/L and the concentration of the phloretin of 0.17125mmol/L (the minimum inhibitory concentration MIC of the myricetin and the phloretin to staphylococcus aureus is selected as the concentration); in the graph, the concentration of myricetin is 3.93mmol/L, the concentration of phloretin is 0.685mmol (the minimum inhibitory concentration MIC of the myricetin and the phloretin for escherichia coli is selected as the concentration) and the concentration of the myricetin and the phloretin are compounded, wherein the volume ratio of B is 7.729:2.271, comparing the theoretical addition value of the ABTS free radical clearance with the actual value, wherein the Combination1 represents the Combination of the concentration of myricetin of 0.2456mmol/L and the concentration of phloretin of 0.17125 mmol/L; combination2 shows that myricetin concentration is 3.93mmol/L and phloretin concentration is 0.685mmol.
Detailed Description
The invention is further illustrated by the following examples, which should not be taken to limit the scope of the invention.
Example 1 detection of minimum inhibitory concentration of myricetin and phloretin
The Minimum Inhibitory Concentrations (MIC) of myricetin and phloretin were measured separately, and were measured in 96-well plates by a microdilution method, and the specific procedures were as follows:
(1) the method comprises the following steps 100 μl of blank broth (sterilized) was added to each well of a 96-well plate;
(2) the method comprises the following steps 100 mu L of myricetin liquid medicine is added to the first hole of three rows 1/2/3, and then double dilution is carried out on the myricetin liquid medicine.
Namely, after adding the liquid medicine into the first hole, fully blowing (at least three times) the liquid medicine and the broth by using a pipetting gun to fully mix the liquid medicine and the broth, then sucking 100 mu L of the liquid medicine into the second hole, fully blowing the liquid medicine into the second hole to fully mix the liquid medicine and the broth, repeating until the last hole is reached, and sucking 100 mu L of the liquid medicine and discarding the liquid medicine;
(3) the method comprises the following steps Then 100. Mu.L (about 10) of diluted bacterial liquid was added to each well 4 CFU/mL), thus forming three replicates (1/2/3 of three rows of samples) for determining one MIC value. At this time, the final concentration of myricetin in each hole is as follows from top to bottom: 31.44, 15.72, 7.86, 3.93, 1.965, 0.9825, 0.49125, 0.245625 (unit: mmol/L).
(4) The method comprises the following steps Adding the prepared phloretin in three columns of 4/5/6 on the same plate in the same method in the steps (2) - (3), so that the final concentration of each Kong Genpi element is as follows: 43.84, 21.92, 10.96, 5.48, 2.74, 1.37, 0.685, 0.3425 (unit: mmol/L). 7/8/9 was potassium sorbate as positive control and final concentrations of 106.4, 53.2, 26.6, 13.3, 6.65, 3.325, 0.83125 (in mmol/L) per well were made, 10/11/12 column was sterile water as negative control, and double dilution was performed except for the negative control in the same manner as in the second and third steps.
(5) The method comprises the following steps After placing the 96-well plates in a 37℃incubator for 24 hours, 50. Mu.L of 0.2mg/mL INT developer was added to each well, and then the wells were incubated in the 37℃incubator for half an hour, and the experimental results were recorded after color development.
And (3) preparation of a reagent:
the myricetin liquid medicine and the phloretin liquid medicine are respectively prepared by taking DMSO as a solvent;
the potassium sorbate is prepared by taking sterile water as a solvent.
The bacterial liquid is bacterial liquid of E.coli and S.aureus.
The results are shown in Table 1, and the results in Table 1 show that the minimum inhibitory concentration of myricetin and phloretin is far lower than that of potassium sorbate, which indicates that the antibacterial effect of myricetin He Genpi is stronger than that of potassium sorbate.
Table 1 minimum inhibitory concentrations MIC (mmol/L) of myricetin, phloretin and potassium sorbate against E.coli and Staphylococcus aureus.
The results show that the antibacterial effect of myricetin and phloretin is stronger than that of potassium sorbate, and the inhibition effect of myricetin and phloretin on staphylococcus aureus is stronger than that of escherichia coli.
Example 2 detection of synergistic antibacterial index of myricetin and phloretin
The synergistic antibacterial index FIC of myricetin and phloretin was determined by a checkerboard assay, and the results are shown in Table 2.
The measurement steps are as follows:
according to the single-drug bacteriostasis test result, the test is carried out by slightly modifying the chessboard test method (cheker-board). Taking 96-hole polystyrene micro-hole plates, sequentially adding 25 mu L of myricetin liquid medicine into each row of holes of the 1 st to 8 th rows along the X-axis direction (left to right) by using a micropipette, so that the final hole concentration of myricetin is respectively 2MIC, 1/2MIC, 1/4MIC, 1/8MIC, 1/16MIC, 1/32MIC and 1/64MIC after bacterial liquid and culture medium are added into each hole; in the same way, 25 mu L of phloretin liquid medicine is sequentially added into each row of holes of the A-F rows along the Y-axis direction (from top to bottom) so that the final hole concentration is respectively 2MIC, 1/2MIC, 1/4MIC, 1/8MIC, 1/16MIC, 1/32MIC and 1/64MIC. Wherein nMIC represents n-fold MIC concentrations, the MIC values were from the results of example 1, and were different MIC values for different species. This example 2 uses the same two bacteria as example 1, namely E.coli and Staphylococcus aureus. Mixing the two materials. Sequentially adding 50 mu L of the prepared bacterial liquid, and finally adding 50 mu L of nutrient broth culture medium. After the liquid adding is completed, the upper plate is covered, the mixture is mixed by slight shaking, and the mixture is placed in a constant temperature incubator for culturing at 37 ℃ for 24 hours, and then the result is observed.
When the MIC of the two bacteria is detected, the same concentration, such as the concentration of myricetin, is selected, the maximum concentration of the two bacteria is 31.44mmol/L, and the concentration of the two bacteria is diluted and reduced according to multiple in sequence, so that the phloretin is the same. There are two cases for 64 th well: (1) when the bacterial liquid is Escherichia coli, the well contains myricetin with a concentration of 0.0614mmol/L and phloretin with a concentration of 0.0107 mmol/L. (2) When the bacterial liquid is staphylococcus aureus, the holes contain myricetin with the concentration of 0.0038mmol/L and phloretin with the concentration of 0.0026 mmol/L.
The graded inhibitory concentration index (fractional inhibitory concentration index, FIC) is one of the pharmacodynamic parameters of the antibacterial agent, and is an index of the combined efficacy of two antibacterial agents (four conditions of synergy, partial synergy or additive effect, independence and antagonism can occur when the two antibacterial agents are used simultaneously).
The FIC index was calculated as follows:
MIC at MIC/a drug alone at mic=a drug combination, MIC at mic+b drug alone at MIC/B drug alone at mic=a drug combination, FIC <0.5, is synergistic; FIC is less than or equal to 1 and is a partial synergistic or additive effect; FIC is 1 and is less than or equal to 2, and is irrelevant; FIC >2 is antagonism.
The experimental results show that the myricetin and the phloretin have a synergistic effect at low concentrations for two bacteria (escherichia coli and staphylococcus aureus), specifically, the myricetin and the phloretin have a synergistic effect at the concentration of less than 1/4MIC, and the myricetin or the phloretin have no synergistic effect at the concentration of either one of more than 1/4 MIC.
Table 2 when the concentrations of myricetin and phloretin are 1/64MIC, the compound volume ratio is 1: FIC value at 1.
Note that: "+" indicates synergistic effect
For example, table 2 shows that when the solvents are DMSO and the concentration is 1/64MIC, the volume ratio of the combination is 1:1, the FIC is less than 0.5 (when the FIC is more than 0.5 and less than 1, it is judged that the partial or independent action is performed, and when the FIC is less than 0.5, it is judged that the two substances are synergistic, and the synergistic action is performed on both Escherichia coli and Staphylococcus aureus.
Example 3 test of the solvent ratio of the control composition
To meet the requirements of foods, medicines and health products, different solvents are further screened to find preservatives suitable for foods, medicines and health products. Although DMSO may have some antibacterial effect itself, the amount of DMSO used is severely limited in the food and pharmaceutical fields. Therefore, this example further verifies whether the synergistic bacteriostatic effect of myricetin and phloretin would be affected with reduced DMSO usage.
The solvents used in this example are different from examples 1 and 2, and the solvents in this example are aqueous solutions containing DMSO in a volume ratio of one thousandth. The solvent was used for testing, and different myricetin He Genpi element ratios were further tested.
The two bacteria are synergistic, so the subsequent experiment is carried out by selecting the ratio.
The purpose of this experiment was to find the optimal volume ratio of myricetin to phloretin, and the relationship with fig. 4 was that fig. 4 was also performed with this ratio, except for the solvent type. In the literature, other flavonoid compounds are all studied for antibacterial effect by using DMSO as a solvent, but are not applied. The influence of the solvent on bacteriostasis is only taken into consideration in the subsequent application.
In example 4, the effect of solvent on bacteriostasis was performed, and in the experiments before example 4, DMSO was used as a solvent, in this experiment, DMSO itself had an inhibitory effect on bacteria, so that the effect of DMSO on bacteriostasis was eliminated after adjusting its volume ratio to one thousandth, and in the ratio optimization experiment, experiments were performed with the addition amount of one thousandth of DMSO, not DMSO of a specific ratio, but the effect of DMSO on bacteriostasis was eliminated.
Some antibacterial effect can be produced by adopting one thousandth of DMSO solvent, and the embodiment proves that DMSO has an influence on the antibacterial effect, but DMSO cannot be used as the solvent due to the specificity of the food and medicine fields. How to select a proper solvent, realizing application in the fields of food and medicine, while ensuring excellent antibacterial effect will be verified in the next example.
EXAMPLE 4 Effect of solvents on bacteriostasis
FIGS. 1A and B are graphs showing the comparison of theoretical addition values and actual values of diameters of S.aureus and E.coli inhibition zone of myricetin with different concentrations and phloretin under the optimal ratio by using DMSO as a solvent. Two solvents of propylene glycol and absolute ethyl alcohol are selected, and the antibacterial effect of the three solvents and whether the three solvents have synergistic effect are compared through an antibacterial zone experiment. At a concentration of 6MIC (=3.93 mmol/l×6=23.58 mmol/L), 8MIC (3.93 mmol/l×8=31.44 mmol/L), 10MIC (3.93 mmol/l×10=39.3 mmol/L), the actual value of both the complex is higher than the theoretical addition value, which is statistically significant at 8MIC and 10 MIC. 6MIC (=0.685 mmol/LX6=4.11 mmol/L), 8MIC (5.48 mmol/L) and 10MIC (6.85 mmol/L) have been described in the drawing-example 4 is described with DMSO as solvent.
The experimental method is as follows:
In fig. 2A and B, propylene glycol is used as a solvent, and the theoretical addition value and the actual value of the diameters of the inhibition zones of s.aureus and e.colli are compared under the optimal ratio of myricetin and phloretin with different concentrations, and the actual values of the two compounds are higher than the theoretical addition value when the concentrations are 6MIC, 8MIC and 10 MIC.
Fig. 3A and B compare actual values of diameters of s.aureus and e.coll inhibition zone of myricetin with different concentrations with phloretin at optimal ratio using absolute ethanol as solvent, and at concentrations of 6MIC, 8MIC, and 10MIC, the actual values of both complexes are higher than theoretical addition value, and have statistical significance at 8MIC and 10 MIC.
Figures 4A and B compare actual values of diameters of s.aureus, e.coli inhibition zone for different concentrations of myricetin and phloretin at optimal ratios using propylene glycol, DMSO and absolute ethanol as solvents.
By exploring the influence of the solvents on the antibacterial effect, the influence of different solvents on the antibacterial effect is found to be larger, and the optimal antibacterial combination and the optimal food combination can be obtained by screening. From the results, after the concentration of myricetin and phloretin is adjusted, the diameters of the inhibition zones of DMSO and propylene glycol are close, and the diameters of the inhibition zones of absolute ethyl alcohol are far greater than those of DMSO and propylene glycol. Absolute ethyl alcohol can be used as a solvent for bacteriostasis of foods and medicines.
In a specific fruit and vegetable fresh-keeping experiment, it is further found that absolute ethyl alcohol has high volatility and strong dehydration, and propylene glycol can be used as a solvent for replacing DMSO for some fruits and vegetables with higher moisture content.
Example 5 measurement of antioxidant index
The free radical scavenging rate of myricetin He Genpi complex was further measured using methods conventional in the art.
TABLE 5 IC50 values for DPPH scavenging by myricetin, phloretin and BHT
From the IC50, the DPPH clearance of myricetin is high Yu Genpi element and BHT, and the myricetin has better antioxidation effect.
Figures 5A and B compare the actual values of DPPH and ABTS radical scavenging rates of myricetin and phloretin in combination with theoretical addition values at the optimal ratio. It was determined whether the scavenging ability of two free radicals DPPH and ABTS was synergistic or not at the optimum ratio. By theoretical addition. In the graph, the Combination1 represents the Combination of the concentration of myricetin of 0.2456mmol/L and the concentration of phloretin of 0.17125mmol/L (the minimum inhibitory concentration MIC of the myricetin and the phloretin on staphylococcus aureus is selected as the concentration); in the figure, combination2 indicates that myricetin concentration is 3.93mmol/L and phloretin concentration is 0.685mmol. The actual value of the compound solution on the scavenging ability of DPPH and ABTS free radicals is higher than the theoretical addition value, and the compound solution has synergistic effect. (synergy is indicated if the actual value is higher than the theoretical sum and has statistical significance).
Claims (10)
1. A bacteriostatic composition with a preservative effect, which is characterized by comprising myricetin and phloretin.
2. The bacteriostatic composition according to claim 1, wherein said composition further comprises at least one solvent selected from DMSO, absolute ethanol or propylene glycol.
3. A bacteriostatic composition according to any one of claims 1-2, characterized in that the molar concentration ratio of myricetin to phloretin is 1.3:1-6:1;
preferably 1.434:1 to 5.74:1.
4. A bacteriostatic composition according to any one of claims 1-3, wherein the molar concentration of myricetin in said bacteriostatic composition is 0.00384mmol/L-39.3mmol/L and the molar concentration of myricetin Pi Suma is 0.00268mmol/L-6.85mmol/L;
preferably, the molar concentration of myricetin is 0.2456mmol/L-39.3mmol/L and the molar concentration of root Pi Suma is 0.17125mmol/L-6.85mmol/L.
5. A bacteriostatic composition according to any one of claims 1-3, wherein in bacteriostatic application against e.coli, the molar concentration of myricetin to phloretin is 5.5:1-6:1; preferably 5.7:1 to 5.8:1; more preferably, the molar concentration of myricetin is 3.93mmol/L-39.3mmol/L and the molar concentration of root Pi Suma is 0.685mmol-6.85mmol;
in an s.aureus-directed bacteriostatic application, the molar concentration of myricetin to phloretin in the bacteriostatic composition is 1.3:1-1.5:1, preferably 1.41:1-1.43:1; more preferably, the molar concentration of myricetin is 0.2456mmol/L-2.456mmol/L and the root Pi Suma molar concentration is 0.17125mmol/L-1.7125mmol/;
in the application of resisting free radicals, the molar concentration of myricetin and phloretin in the antibacterial composition is 5.5:1-6:1; preferably 5.7:1 to 5.8:1; more preferably, the molar concentration of myricetin is 3.93mmol/L and the molar concentration of root Pi Suma is 0.685mmol; or alternatively
The molar concentration of myricetin and phloretin is 1.3:1-1.5:1, preferably 1.41:1-1.43:1; more preferably, the molar concentration of myricetin is 0.2456mmol/L and the root Pi Suma molar concentration is 0.17125mmol/L.
6. A method of preparing a bacteriostatic composition according to any one of claims 1-5, characterized in that it comprises the steps of:
the myricetin and phloretin are dispersed in a solvent to prepare a bacteriostatic composition solution.
7. The method of claim 6, wherein the solvent is selected from DMSO, absolute ethanol, and propylene glycol.
8. Use of the bacteriostatic composition according to any one of claims 1-5 for the preparation of a preservative;
preferably, the preservative is applied to medicines and foods.
9. Use of a bacteriostatic composition according to any one of claims 1-5 for the preparation of a bacteriostatic agent for inhibiting bacteria;
preferably, the bacteria are staphylococcus aureus, escherichia coli;
preferably, the bacteriostat is applied to medicines and foods.
10. Use of a bacteriostatic composition according to any one of claims 1-5 for the preparation of a free radical scavenger;
preferably, the radicals are selected from DPPH and ABTS radicals.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210212543.4A CN116195586B (en) | 2022-03-01 | 2022-03-01 | Composition of myricetin and phloretin, preparation method thereof and application of composition in corrosion prevention |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210212543.4A CN116195586B (en) | 2022-03-01 | 2022-03-01 | Composition of myricetin and phloretin, preparation method thereof and application of composition in corrosion prevention |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN116195586A true CN116195586A (en) | 2023-06-02 |
| CN116195586B CN116195586B (en) | 2024-04-02 |
Family
ID=86515213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210212543.4A Active CN116195586B (en) | 2022-03-01 | 2022-03-01 | Composition of myricetin and phloretin, preparation method thereof and application of composition in corrosion prevention |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116195586B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250175A (en) * | 2008-04-01 | 2008-08-27 | 赫玉芳 | Preparation of myricetin, medicinal preparation and new medical usage |
| CN103936606A (en) * | 2014-04-03 | 2014-07-23 | 陕西师范大学 | Water-soluble phloretin derivative and preparation method thereof |
| CN109700819A (en) * | 2017-10-25 | 2019-05-03 | 苏州凯祥生物科技有限公司 | A kind of pharmaceutical composition of Weight-reducing and lipid-lowering and preparation method thereof and purposes |
| CN113533565A (en) * | 2021-07-12 | 2021-10-22 | 新疆医科大学 | Method for detecting concentrations of 8 flavonoid compounds in human urine by UPLC-MS/MS method |
-
2022
- 2022-03-01 CN CN202210212543.4A patent/CN116195586B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101250175A (en) * | 2008-04-01 | 2008-08-27 | 赫玉芳 | Preparation of myricetin, medicinal preparation and new medical usage |
| CN103936606A (en) * | 2014-04-03 | 2014-07-23 | 陕西师范大学 | Water-soluble phloretin derivative and preparation method thereof |
| CN109700819A (en) * | 2017-10-25 | 2019-05-03 | 苏州凯祥生物科技有限公司 | A kind of pharmaceutical composition of Weight-reducing and lipid-lowering and preparation method thereof and purposes |
| CN113533565A (en) * | 2021-07-12 | 2021-10-22 | 新疆医科大学 | Method for detecting concentrations of 8 flavonoid compounds in human urine by UPLC-MS/MS method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN116195586B (en) | 2024-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Frassinetti et al. | Antibacterial and antioxidant activity of essential oils from Citrus spp. | |
| Li et al. | Antifungal properties and mechanisms of three volatile aldehydes (octanal, nonanal and decanal) on Aspergillus flavus | |
| Denardi‐Souza et al. | Antifungal effect of phenolic extract of fermented rice bran with Rhizopus oryzae and its potential use in loaf bread shelf life extension | |
| CN101073435A (en) | Natural-plant food antiseptics | |
| Ahmed et al. | In vitro activity of natural honey alone and in combination with curcuma starch against Rhodotorula mucilaginosa in correlation with bioactive compounds and diastase activity | |
| CN101801182A (en) | New antibacterial agent based on fatty acid esters of hydroxy carboxylic acids | |
| Wang et al. | Benzyl isothiocyanate fumigation inhibits growth, membrane integrity and mycotoxin production in Alternaria alternata | |
| US20120251700A1 (en) | Food additive | |
| CN116195586B (en) | Composition of myricetin and phloretin, preparation method thereof and application of composition in corrosion prevention | |
| CN105454273A (en) | Bactericide composition | |
| KR100783152B1 (en) | Antibacterial composition containing ginko extract | |
| Tsukatani et al. | Combined effects of fumaric, lactic, and ferulic acid against food-borne pathogenic biofilms | |
| Friedman et al. | Antimicrobial activities of red wine-based formulations containing plant extracts against Escherichia coli O157: H7 and Salmonella enterica serovar Hadar | |
| KR19990058672A (en) | Natural antimicrobial composition based on chitosan | |
| Kahraman et al. | Total phenolic content, antiradical, antimicrobial and antibiofilm properties of grape and apple vinegar | |
| Saleh et al. | Vital Value of Coriander and Fennel Volatile Oils on Quality Beef Burger During Cryopreservation | |
| KR20160084050A (en) | Composition for antioxidation and browning inhibition, food composition comprising the same, and method of enhancing anti-oxidant activity and inhibiting browning of food | |
| CN112889913B (en) | Application of eurycolatone F in food preservation | |
| KR100509176B1 (en) | Antibacterial and Antifungal Composition Including Fennel Extract | |
| KR100317482B1 (en) | Nutrient agent of kim-chi containing water-soluble chitosan and using method thereof | |
| Saraya et al. | Sappan wood extract used as preservative in chili paste | |
| JPH0427373A (en) | Preparation of improving shelf stability of food | |
| CN116784446B (en) | Composition for synergistically inhibiting pseudomonas aeruginosa and application thereof | |
| CN114467950B (en) | Sterilization composition for preventing and treating taro epidemic disease | |
| CN112602719B (en) | Antibacterial composition and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |