CN111888273A - Plant-derived natural bacteriostatic agent or preservative and application thereof - Google Patents
Plant-derived natural bacteriostatic agent or preservative and application thereof Download PDFInfo
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- CN111888273A CN111888273A CN202010789787.XA CN202010789787A CN111888273A CN 111888273 A CN111888273 A CN 111888273A CN 202010789787 A CN202010789787 A CN 202010789787A CN 111888273 A CN111888273 A CN 111888273A
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- preservative
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- 239000003755 preservative agent Substances 0.000 title claims abstract description 55
- 230000002335 preservative effect Effects 0.000 title claims abstract description 47
- 239000000022 bacteriostatic agent Substances 0.000 title claims abstract description 8
- 239000000284 extract Substances 0.000 claims abstract description 49
- 240000005125 Myrtus communis Species 0.000 claims abstract description 30
- 235000013418 Myrtus communis Nutrition 0.000 claims abstract description 29
- 241000196324 Embryophyta Species 0.000 claims abstract description 21
- 229940125904 compound 1 Drugs 0.000 claims abstract description 21
- 229940125782 compound 2 Drugs 0.000 claims abstract description 21
- 239000002537 cosmetic Substances 0.000 claims abstract description 18
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 17
- 241001018563 Nekemias grossedentata Species 0.000 claims abstract description 8
- 230000003385 bacteriostatic effect Effects 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 18
- 241000588724 Escherichia coli Species 0.000 claims description 17
- 241000222122 Candida albicans Species 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 229940095731 candida albicans Drugs 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 241000191967 Staphylococcus aureus Species 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 239000000469 ethanolic extract Substances 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
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- 229940079593 drug Drugs 0.000 claims description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 claims description 4
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- 150000001875 compounds Chemical class 0.000 abstract description 17
- KJXSIXMJHKAJOD-LSDHHAIUSA-N (+)-dihydromyricetin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC(O)=C(O)C(O)=C1 KJXSIXMJHKAJOD-LSDHHAIUSA-N 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 13
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
- 150000002576 ketones Chemical class 0.000 abstract description 8
- KQILIWXGGKGKNX-UHFFFAOYSA-N dihydromyricetin Natural products OC1C(=C(Oc2cc(O)cc(O)c12)c3cc(O)c(O)c(O)c3)O KQILIWXGGKGKNX-UHFFFAOYSA-N 0.000 abstract description 7
- 238000002474 experimental method Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 7
- 238000011161 development Methods 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 241000894006 Bacteria Species 0.000 description 11
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 3
- 241000219926 Myrtaceae Species 0.000 description 3
- PLXBWHJQWKZRKG-UHFFFAOYSA-N Resazurin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3[N+]([O-])=C21 PLXBWHJQWKZRKG-UHFFFAOYSA-N 0.000 description 3
- 229940124350 antibacterial drug Drugs 0.000 description 3
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- -1 ketone compounds Chemical class 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YEDFEBOUHSBQBT-UHFFFAOYSA-N 2,3-dihydroflavon-3-ol Chemical compound O1C2=CC=CC=C2C(=O)C(O)C1C1=CC=CC=C1 YEDFEBOUHSBQBT-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- 235000003840 Amygdalus nana Nutrition 0.000 description 2
- 244000296825 Amygdalus nana Species 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 235000011432 Prunus Nutrition 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
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- 241000563984 Ampelopsis Species 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 235000009388 Parthenocissus quinquefolia Nutrition 0.000 description 1
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- 235000007234 Rhodomyrtus tomentosa Nutrition 0.000 description 1
- 240000007994 Rhodomyrtus tomentosa Species 0.000 description 1
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- 238000009395 breeding Methods 0.000 description 1
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- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
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- HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3499—Organic compounds containing oxygen with doubly-bound oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/592—Mixtures of compounds complementing their respective functions
- A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18
-
- 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
Abstract
The invention discloses a plant source natural bacteriostatic agent or preservative and application thereof. It comprises compound 1 and compound 2, or extract 1 and extract 2; the structural formula of the compound 1 is shown as a formula 1, and the structural formula of the compound 2 is shown as a formula 2. The compound 1 (myrtle ketone) obtained from edible myrtle fruits and the compound 2 (dihydromyricetin) obtained from Ampelopsis grossedentata leaves have synergistic antibacterial effect. The mixture of compounds 1 and 2 (weight: 40:60) was added as natural preservative 1 at 0.02%, the mixture of extracts 1 and 2 (weight: 50) was added as natural preservative 2 at 0.4%,the preservative is added into cosmetics respectively, can pass preservative challenge experiments with excellent preservative capability basically equivalent to that of chemical preservatives, and has good application prospect and development value.
Description
The technical field is as follows:
the invention belongs to the field of sterilization and corrosion prevention, and particularly relates to a plant-derived natural bacteriostatic agent or preservative and application thereof.
Background art:
the preservative is an indispensable part for preserving cosmetics and foods, and has the function of inhibiting the breeding and propagation of microorganisms. However, the addition of pure chemical preservatives often has certain safety or irritation problems, for example, the skin aging is accelerated by using cosmetics containing the chemical preservatives for a long time, and skin allergic reactions are easily generated by people with special skin types. With the improvement of the safety requirements of consumers on cosmetics and foods, the application of chemically synthesized preservatives in the cosmetics and the foods is reduced, and the search for novel, effective and safe natural preservatives becomes a new development direction of the research on the cosmetics and the foods.
The myrtle fruit is the fruit of myrtle (Rhodomyrtus tomentosa) belonging to Myrtaceae and Myrtle, and has an egg-shaped pot shape and purple black color when ripe. Blossom in summer, 4-5 months in flowering period, and bearing the fruit with laces. The mature fruit is edible and can be used for brewing wine. At present, documents and patents report that myrtle ketone compounds and derivatives thereof in myrtle leaves have the effect of resisting gram-positive bacteria (patent application number: CN 104761565A myrtle ketone compound and application thereof in preparing antibacterial drugs; CN 108752305A ring-closed myrtle ketone analogue and application thereof in antibacterial drugs; CN 105859537A ring-opened myrtle ketone analogue and preparation method thereof and application thereof in antibacterial drugs). At present, no document or patent reports the broad-spectrum bacteriostatic action and bacteriostatic component of the edible myrtle fruit, and no related report reports the synergistic action of the bacteriostatic component and the application of the synergistic action to replace a preservative.
The invention content is as follows:
the invention aims to overcome the defects of the prior art, obtains the bacteriostatic part and the bacteriostatic component in the edible myrtle fruit through research, clearly researches the antibacterial spectrum of the edible myrtle fruit, finds the synergistic effect of the bacteriostatic component in another edible plant and completely replaces or partially replaces a chemical preservative to be used in cosmetics or food.
The invention discovers that the synergistic bacteriostasis effect of the compound 1 (myrtle ketone) and the compound 2 (dihydromyricetin) is 0.08 of the synergistic bacteriostasis effect on escherichia coli, 0.03 of the synergistic bacteriostasis effect on staphylococcus aureus and 0.07 of the synergistic bacteriostasis effect on candida albicans. The myrtle fruit ethanol extract (extract 1) containing myrtle ketone and the prunus dentata leaf ethanol extract (extract 2) containing dihydromyricetin also have synergistic antibacterial effect.
The first purpose of the invention is to provide a plant-derived natural bacteriostatic agent or preservative, which comprises a compound 1 and a compound 2, or an extract 1 and an extract 2;
the structural formula of the compound 1 is shown as a formula 1, and the structural formula of the compound 2 is shown as a formula 2:
the extract 1 is prepared by pulverizing myrtle fruit, extracting with ethanol or ethanol water solution, concentrating to obtain ethanol extract, suspending in water, extracting with n-hexane, and spin drying the extract with solvent to obtain extract 1;
the extract 2 is obtained by adding dry leaves of the bud of the Ampelopsis grossedentata into ethanol or ethanol water solution for reflux extraction, concentrating, standing, filtering crystals after light yellow granular crystals are separated out, and drying.
Preferably, the extract 1 is prepared by crushing dried myrtle fruits, extracting with 95% ethanol aqueous solution by volume fraction, performing rotary evaporation under reduced pressure to obtain an ethanol extract, suspending the ethanol extract in water according to the mass ratio of 1:1, extracting with n-hexane, and performing rotary drying on the extracted part with a solvent to obtain the extract 1.
Preferably, the extract 2 is obtained by adding the dry leaves of the bud of the Ampelopsis grossedentata into an ethanol aqueous solution with the volume fraction of 90%, soaking, then carrying out reflux extraction at 55 ℃, filtering while hot, concentrating under reduced pressure to remove the solvent ethanol after filtering, standing until light yellow particles are crystallized and separated out, carrying out suction filtration on the crystals, and drying.
Preferably, the compound 1 and the compound 2 are mixed according to a mass ratio of 40: 30 to 60, preferably 40: 31.5.
Preferably, the extract 1 and the extract 2 are mixed according to the mass ratio of 50: 50.
Preferably, the bacteriostatic agent or preservative is a drug for inhibiting staphylococcus aureus, bacillus cereus, escherichia coli, salmonella typhi or candida albicans, and further a drug for inhibiting escherichia coli or candida albicans.
The second purpose of the invention is to provide the application of the bacteriostatic agent or the preservative in bacteriostasis or preservation, such as application in cosmetics and foods.
The compound 1 (myrtle ketone) obtained from edible myrtle fruits and the compound 2 (dihydromyricetin) obtained from the Ampelopsis grossedentata have synergistic bacteriostasis, the synergistic effect (S) on escherichia coli is 0.08, the synergistic effect (S) on staphylococcus aureus is 0.03, and the synergistic effect on candida albicans is 0.07. The myrtle fruit ethanol extract (extract 1) containing myrtle ketone and the prunus dentata leaf ethanol extract (extract 2) containing dihydromyricetin also have synergistic antibacterial effect. The compound 1 and 2 mixture (weight: 40:60) is added as natural preservative 1 by 0.02%, and the extract 1 and 2 mixture (weight: 50) is added as natural preservative 2 by 0.4%, and the natural preservative and the extract are respectively added into cosmetics, so that the preservative effect of the cosmetic can be excellent through preservative challenge experiments, the preservative capability of the cosmetic is basically equivalent to that of a chemical preservative, and the cosmetic has good application prospect and development value.
The specific implementation mode is as follows:
the following examples are further illustrative of the present invention and are not intended to be limiting thereof.
The invention is illustrated below with reference to specific examples. It will be understood by those skilled in the art that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention in any way.
The experimental procedures in the following examples are conventional unless otherwise specified. The raw materials and reagents used in the following examples are all commercially available products unless otherwise specified.
Example 1: myrtacone compound separated from Myrtaceae plant
1.1 plant Material
The plant Myrtus communis of Myrtaceae Myrtus is used as an experimental raw material, and the plant is widely distributed in the south of China, especially in the south of Lingnan. The plant material of the experiment is collected from Nankang county (district) of Ganzhou city in Jiangxi province, and is identified as myrtle (R.tominosa) of myrtle in Myrtaceae by the researchers of Wangwang plant Garden in south China, China academy of sciences. Plant specimens are currently available in the laboratories for natural products and chemical and biological research in the plantations of south China, academy of sciences.
1.2 laboratory instruments and reagents
The optical rotation data was measured using a Perkin-Elmer 341polar imeter (Perkin-Elmer Co., U.S.A.). The UV spectrum was measured by a Perkin-Elmer Lambda 35UV-vis spectrophotometer (Perkin-Elmer Co., U.S.A.) using methanol or chloroform as a solvent. The IR spectrum was measured by a Bruker Vertex 33infrared spectrophotometer (Bruker, Germany) which requires tabletting before measurement. The NMR spectra were measured by Bruker AVIII500 superconducting NMR from Bruker, TMS being an internal standard, in ppm and J in Hz, for hydrogen, carbon, DEPT-135 and two-dimensional spectra. The preparative HPLC is L3000 type HPLC (Beijing Innovation technology Co., Ltd.), and the chromatographic column is C18 column (ALLTIMAC1810U, 250nm × 10nm, 3mL/min), and is equipped with single wavelength ultraviolet detector. High resolution mass spectra were determined by a Bruker BioTOFIIIQ mass spectrometer from Bruker. 100-200, 200-300 and 300-400 mesh silica gel and thin-layer chromatography plates are produced by Qingdao spectral separation materials, Inc. MCI gel (CHP20P,75-150mm) was manufactured by Mitsubishi chemical corporation of Japan. Sephadex LH-20 gel was produced by Amersham biosciences, Sweden. The organic solvent is from Shanghai chemical materials, Inc. The thin-layer chromatography developer is 5% concentrated sulfuric acid-ethanol solution, and compounds with ultraviolet absorption need to be observed under an ultraviolet lamp. The proportion of the mixed solvent used in the experimental process is volume ratio.
1.3 obtaining the extract
Sufficiently crushing (20KG) the dried myrtle fruits, extracting 3 times (30L multiplied by 3) with a 95% ethanol aqueous solution with volume fraction, carrying out rotary evaporation on the combined solvents under reduced pressure to obtain a brown syrupy residue which is an ethanol extract 1(2.5KG), suspending the brown syrupy residue in water (1:1, weight ratio), extracting with n-hexane (3L multiplied by 3), and carrying out rotary drying on the extracted part by using the solvent to obtain an n-hexane part (extract 1); extracting the residual water solution with ethyl acetate (3L × 3), and spin-drying the extracted part with solvent to obtain ethyl acetate part and the residual water part to obtain water part.
1.4 isolation to obtain monomeric Compounds
In the experiment, chloroform with a small amount of n-hexane part (or ethyl acetate part) of myrtle fruits is completely dissolved in a sample mixing pot, then 500g of silica gel (80-100 meshes) is used for mixing samples, the mixture is uniformly stirred, after the solvent is completely volatilized, the samples are loaded by a dry method, gradient elution is carried out by using an n-hexane-ethyl acetate system 10:1, 5:1, 2:1, 1:1 and 0:1v/v, finally, a methanol column is flushed, fractions with the same main point are combined after TLC thin-layer chromatography detection, and TLC detection (a developing solvent n-hexane: ethyl acetate is 5:1v/v) is collected to show blue fluorescence under an ultraviolet lamp; performing MCI column chromatography to remove pigment, performing Sephadex LH-20 gel column chromatography, performing gradient elution with n-hexane-ethyl acetate system (8:1 → 1:1v/v), and collecting blue fluorescence under ultraviolet lamp by TLC detection (developing solvent n-hexane: ethyl acetate 5:1 v/v); c2, orange part under the action of sulfuric acid-ethanol color developing agent. And Fr, performing Sephadex LH-20 gel column chromatography on the C2, and eluting with chloroform and methanol (1:1v/v) to obtain a compound 1. TLC detection (developing solvent n-hexane: ethyl acetate: 4:1v/v) gave compound 1 Rf of 0.4.
The compound 1 is myrtle ketone, is a light yellow needle crystal, and is easily dissolved in chloroform; nuclear magnetic data:1HNMR(CDCl3,500MHz):H6.12(1H,s,H-5),4.27(1H,t,J＝5.6Hz,H-9),2.99(3H,m,H-1”,H-2”),2.28(1H,dp,J＝13.3,6.6Hz,H-3'),1.55,1.43,1.41,1.37(each 3H,s,H-11,H-12,H-13,H-14),0.98(6H,d,J＝6.7,Hz,H-4',H-5'),0.87,0.83(each 3H,d,J＝6.0Hz,H-3”,H-4”)；13CNMR(CDCl3125MHz) 212.2(C-3),206.7(C-1'),198.3(C-1),167.5(C-4a),162.8(C-8),158.7(C-6),155.7(C-10a),114.3(C-9a),107.7(C-7),106.4(C-8a),94.7(C-5),56.1(C-2),53.2(C-2'),46.4(C-4),45.8(C-1 "), 25.5(C-9),25.5 (C-2"), 25.2,25.1(C-13, C-14),24.7,24.6(C-11, C-12),24.2(C-3'),23.5,23.2(C-3 ', C-4', 22.8, 22.8(C-4', C-5 '). The structural formula of compound 1 is shown below:
example 2: dihydromyricetin compound separated from Vitaceae plant
2.1 plant Material
The plant material was collected from Dayun county of Ganzhou city, Jiangxi province, and was identified as Ampelopsis grossedentata (hand. -Mazz.) W.T.Wang in Vitaceae, Ampelopsis, by researchers in the south China plant Garden of China academy of sciences. Plant specimens are currently available in the laboratories for natural products and chemical and biological research in the plantations of south China, academy of sciences.
2.2 laboratory instruments and reagents
Same as example 1 in 1.2.
2.3 obtaining the extract
Weighing 250g of dry sprout leaves of Ampelopsis grossedentata, adding into 90% ethanol water solution by volume fraction, soaking for half an hour, and refluxing at 55 deg.C for 2 times, each time for 40 min; filtering while hot, concentrating under reduced pressure to remove ethanol, standing for 1d, filtering, and drying to obtain extract 2.
2.4 isolation of monomeric Compounds
Weighing 2100g of 2.3 extract, adding 1000ml of acetone, refluxing at 45 deg.C for 60min, concentrating the extractive solution, adding 4000ml of hot water to dissolve, standing for 1h, filtering after white crystal is separated out, repeating the step for 5 times, and vacuum filtering and drying to obtain compound 2.
The compound 2 is dihydromyricetin, yellow white powdery crystalline substance, is easily dissolved in organic solvent such as acetone, methanol, ethanol, etc., and has strong ultraviolet absorption and yellow color when heated by concentrated sulfuric acid. Nuclear magnetic data:1H NMR(Methanol-d4500MHz) 6.57(2H, s, H-2 ', H-6'), proton signal of symmetrically substituted aromatic rings; 5.95(1H, d, J ═ 2.1Hz, H-8),5.90(1H, d, J ═ 2.1Hz, H-6), meta-coupled aromatic ring proton signals; 4.85(1H, d, J ═ 11.4Hz, H-3),4.49(1H, d, J ═ 11.4Hz, H-2), typical flavanonol C ring proton signal.13C NMR(Methanol-d4125MHz) 196.9(C-4),83.8(C-2),72.3(C-3), a typical flavanonol C-ring carbon signal; 145.5(C-3 ', C-5'), 133.5(C-4 '), 127.7 (C-1'), 106.8(C-2 ', C-6'), symmetrically substituted aromatic rings, the substituent being hydroxyl; contains a total of 15 carbon signals. The structural formula of compound 2 is shown below:
example 3: detection of bacteriostatic activity
The invention selects a microdilution method which has higher sensitivity and can quantitatively detect the in-vitro antibacterial activity of the medicament, namely, the antibacterial activity of the extract, the compound 1 and the compound 2 is evaluated by using the Minimum Inhibitory Concentration (MIC). The Minimal Inhibitory Concentration (MIC) of the compound was determined using resazurin color development. Resazurin is a blue non-fluorescent dye that can be reduced to a pink fluorescent dye by a variety of reductases in living cells, while inactive cells do not have the metabolic capacity to reduce it. The method reflects the bacteriostatic ability of the extract through the change of the color of the bacterial liquid, namely after the indicator, the extract and the bacterial liquid are co-cultured for a certain time, if the bacterial liquid turns red, the compound has no bacteriostatic activity, and if the bacterial liquid maintains blue, the compound has bacteriostatic activity. The experiments will use a 96-well plate dilution gradient method to simultaneously determine the MIC of various compounds.
Staphylococcus aureus (ATCC 29213), Bacillus cereus (ATCC 10876), Escherichia coli (ATCC8739), Salmonella typhi (CMCC 44102), Candida albicans (ATCC 10231) were obtained from the institute of microbiology, Guangdong, China center for culture collection.
Inoculating bacteria such as Escherichia coli and Staphylococcus aureus in MH broth culture medium, and culturing at 37 deg.C for 12 hr; candida albicans was inoculated in Martin medium and cultured at 30 ℃ for 3 d. The above microbial cultures were diluted to a concentration of 10 with MH broth medium, respectively6-107CFU/mL of bacterial suspension. 7.5mL of indicator solution (100. mu.g/mL of resazurin aqueous solution) was mixed with 5mL of the suspension of the test bacteria, the first row was 180. mu.L of the mixture, and the other rows were 100. mu.L.
Diluting the extract and the compound to be detected to proper concentrations by DMSO, adding 20 mu L of sample in the first row of a 96-well plate, and respectively making three controls in each example; and after uniformly mixing the first row, taking 100 mu L of the solution, transferring the solution to the second row, uniformly mixing the solution, sequentially diluting the solution by 2 times to form a certain concentration gradient in the operation of other rows, putting the solution into a constant-temperature incubator at 37 ℃ for culturing for 8-12 h, observing and determining an MIC value based on the color change and the turbidity degree of the pore plate solution.
TABLE 1 bacteriostatic activity of different samples (unit: ug/mL)
The experimental results shown in table 1 show that the extract 1 and the compound 1 have certain bacteriostatic effects on gram-negative bacteria represented by escherichia coli and salmonella, gram-positive bacteria represented by staphylococcus aureus and bacillus cereus and fungi represented by candida albicans, particularly on gram-positive bacteria represented by staphylococcus aureus and bacillus cereus, and the bacteriostatic activity of the compound 1 is improved by about 12.5-200 times compared with that of the extract 1. The extract 2 and the compound 2 also have certain bacteriostatic effect on detected microbial strains, the bacteriostatic action is relatively balanced, and the bacteriostatic activity of the compound 2 is improved by about 16-32 times compared with that of the extract 2.
Example 4: research on synergistic antibacterial effect
Staphylococcus aureus (ATCC 29213), Escherichia coli (ATCC8739), Candida albicans (ATCC 10231) obtained from the institute for microorganisms, Guangdong province, culture Collection (Guangzhou, China)
In the reference (Thangamani et al, reproducing celecoxib as a topologic microbiological agent 2015), extracts 1 and 2, compounds 1 and 2, respectively, were studied in vitro for synergistic effects on E.coli, S.aureus, and C.albicans using a Bliss independent model. Using compounds 1 and 2 as examples of synergistic anti-E.coli, E.coli was inoculated in MH broth and cultured at 37 ℃ for 12 h. The above E.coli culture was diluted to a concentration of 10 using MH broth medium6-107CFU/mL of bacterial suspension. mu.L of the above bacterial suspension was added to each well of a 96-well plate, and Compound 1 at a sub-inhibitory concentration (0.5 MIC: 40. mu.g/mL), Compound 2 at a sub-inhibitory concentration (0.5 MIC: 31.25. mu.g/mL), Compound 1 at a sub-inhibitory concentration and Compound 2 were added to each well, and incubated overnight for 12h to measure the OD value.
The synergy (S) was calculated using the formula: (OD1/OD0) (OD2/OD0) - (OD12/OD 0). The parameter OD12 refers to the optical density value of the bacteria in the presence of both 1 and 2; the parameters OD1 and OD2 refer to the optical density values of the bacteria in the presence of only 1 compound, respectively; the parameter OD0 refers to the optical density value of the bacteria in the absence of the drug. The degree of synergy (S) values correspond to the following cutoff values: zero indicates neutrality, above zero (positive values) indicates synergy, and below zero (negative values) indicates antagonism. Drug combinations with higher positive values represent a high degree of synergy.
TABLE 2 synergistic antibacterial study (unit: μ g/mL)
| Bacterial strains | Synergistic effect of compounds 1 and 2(S) | Extracts 1 and 2 |
| Escherichia coli | 0.09 | 0.08 |
| Staphylococcus aureus | 0.03 | 0.02 |
| Candida albicans | 0.07 | 0.06 |
The results in table 2 show that the compounds 1 and 2 and the extracts 1 and 2 have certain synergistic bacteriostatic action, particularly the S value of the synergistic bacteriostatic action on escherichia coli is 0.08-0.09, and the S value on candida albicans is 0.06-0.07, which indicates that the synergistic bacteriostatic effect is excellent.
Example 5: application of substituting preservative
Staphylococcus aureus (ATCC 29213), Salmonella typhi (CMCC 44102), Escherichia coli (ATCC8739), Candida albicans (ATCC 10231) obtained from the institute of microbiology, Guangdong, culture Collection (Guangzhou, China)
According to the results of the Minimal Inhibitory Concentration (MIC) and the synergy studied in the above examples, which indicate that the compounds 1 and 2, and the extracts 1 and 2 can synergistically exert a better bacteriostatic effect, the above compounds 1 and 2 were mixed (weight ratio 40:60) as the natural preservative 1, and the extracts 1 and 2 were mixed (weight 50:50) as the natural preservative 2, respectively, and added to the cosmetic, the toiletry and perfume association (CTFA), and the united states pharmacopeia, to perform a preservation challenge test with reference to the well-known microbial challenge test methods of cosmetics, toiletry and perfume associations (CTFA), and the united states pharmacopeia.
Firstly, 3 parts of a certain amount of cream without preservative in a basic formula are taken, wherein 1 part of cream is added with the natural preservative of the patent1, the content of a final preservative in a sample is 0.02 percent by mass, 1 part of a natural preservative 2 is added to ensure that the content of the final preservative in the sample is 0.4 percent by mass, 1 part of a chemical preservative p-hydroxyacetophenone is added to ensure that the content of the chemical preservative is 0.5 percent by mass, and then mixed bacteria (staphylococcus aureus bacteria liquid, salmonella bacteria liquid and escherichia coli bacteria liquid in logarithmic phase are mixed according to the volume ratio of 1: 1: 1) and fungus (candida albicans) suspension are respectively added to ensure that the final bacteria content of each tested sample is 1-5 multiplied by 106cfu/g bacteria and 1-5X 105cfu/g fungi. Then, the mixture was mixed well and cultured at 28 ℃. The total number of bacteria and the total number of fungi were measured according to the experimental methods recommended by the society for cosmetics and fragrance and flavor (CTFA) at 0, 7, 14 and 28 days of inoculation to judge the preservative efficacy of the cosmetics. The judgment standard is as follows: when each sample was inoculated once, the amount of viable bacteria was reduced to not more than 0.1% of the initial concentration on day 14, and then gradually decreased, and aseptically grown on day 28. The preservative is effective and passes the test; otherwise, the preservative was not effective, but was not tested.
TABLE 3 Corrosion protection challenge test results
According to the data in the table 3, the natural preservatives 1 and 2 can pass through the antiseptic challenge when being added into the cream cosmetics, the antiseptic capability of the natural preservatives is basically equivalent to that of a pure chemical preservative, and the natural preservatives have good application prospect and development value.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other modifications, equivalent substitutions, improvements and the like which do not depart from the spirit and principle of the present invention are all equivalent substitutions and are included in the protection scope of the present invention.
Claims (10)
1. A plant-derived natural bacteriostatic or preservative, which is characterized by comprising a compound 1 and a compound 2, or an extract 1 and an extract 2;
the structural formula of the compound 1 is shown as a formula 1, and the structural formula of the compound 2 is shown as a formula 2:
the extract 1 is prepared by pulverizing myrtle fruit, extracting with ethanol or ethanol water solution, concentrating to obtain ethanol extract, suspending in water, extracting with n-hexane, and spin drying the extract with solvent to obtain extract 1;
the extract 2 is obtained by adding dry leaves of the bud of the Ampelopsis grossedentata into ethanol or ethanol water solution for reflux extraction, concentrating, standing, filtering crystals after light yellow granular crystals are separated out, and drying.
2. The plant-derived natural bacteriostatic or preservative according to claim 1, wherein the extract 1 is prepared by pulverizing dried myrtle fruits, extracting with 95% ethanol aqueous solution by volume fraction, performing rotary evaporation under reduced pressure to obtain an ethanol extract, suspending the ethanol extract in water at a mass ratio of 1:1, extracting with n-hexane, and performing rotary drying on the extracted part with a solvent to obtain the extract 1.
3. The plant-derived natural bacteriostatic or preservative according to claim 1, wherein the extract 2 is prepared by adding dry leaves of sprout heads of Ampelopsis grossedentata into an ethanol aqueous solution with a volume fraction of 90%, soaking, extracting under reflux at 55 ℃, filtering while hot, concentrating under reduced pressure to remove ethanol as a solvent after filtering, standing until pale yellow particles are crystallized, filtering the crystals by suction, and drying.
4. The plant-derived natural bacteriostatic or preservative according to claim 1, wherein the ratio of compound 1 to compound 2 is 40: 30-60 mixing.
5. The plant-derived natural bacteriostatic or preservative according to claim 4, wherein the compound 1 and the compound 2 are mixed according to the mass ratio of 40: 31.5.
6. The plant-derived natural bacteriostatic or preservative according to claim 1, wherein the extract 1 and the extract 2 are mixed according to a mass ratio of 50: 50.
7. The plant-derived natural bacteriostatic or preservative according to claim 1, wherein the bacteriostatic or preservative is a drug inhibiting staphylococcus aureus, bacillus cereus, escherichia coli, salmonella typhi or candida albicans.
8. The plant-derived natural bacteriostatic or preservative according to claim 7, wherein the bacteriostatic or preservative is a drug for inhibiting escherichia coli or candida albicans.
9. Use of a bacteriostatic or preservative agent according to claim 1 for bacteriostatic or preservative purposes.
10. Use according to claim 9, in cosmetics and foodstuffs.
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| CN115626906A (en) * | 2022-10-25 | 2023-01-20 | 中国科学院华南植物园 | Industrial extraction method of high-purity myrtle ketone |
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