WO2015194772A2 - 항균 및 방부 활성을 갖는 녹농균 배양액 추출물을 포함하는 조성물 및 이의 용도 - Google Patents
항균 및 방부 활성을 갖는 녹농균 배양액 추출물을 포함하는 조성물 및 이의 용도 Download PDFInfo
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- WO2015194772A2 WO2015194772A2 PCT/KR2015/005535 KR2015005535W WO2015194772A2 WO 2015194772 A2 WO2015194772 A2 WO 2015194772A2 KR 2015005535 W KR2015005535 W KR 2015005535W WO 2015194772 A2 WO2015194772 A2 WO 2015194772A2
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- pseudomonas aeruginosa
- extract
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- aeruginosa culture
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Definitions
- composition comprising Pseudomonas aeruginosa culture extract with antibacterial and antiseptic activity and use thereof
- the present invention relates to a composition
- a composition comprising the extract of Pseudomonas aeruginosa culture having antibacterial and antiseptic activity and its use.
- Paraben is a bactericidal preservative mainly used to suppress microbial growth and increase shelf life in cosmetics, foods and medicines. It has been used for five quarters since it was first used in medicine in the mid 1920s. . While the use of parabens is widespread and prolonged in a variety of products, studies of parabens' estrogens have been reported to raise the issue of parabens safety in humans.
- Biosurfactant is a surfactant obtained from biological materials such as microorganisms, animals, and plants, and is attracting attention because of its low toxicity and easy degradation by ecosystems. Biosurfactant's advantages over chemically synthesized surfactants are firstly non-toxic and easy to biodegrade, so they are not secondary pollution sources. Secondly, they can be used for special purposes because of the complex chemical structures that are difficult to synthesize by conventional methods. Third, in terms of the physical and chemical performance of surfactants such as surface tension lowering ability, stability against temperature and pH, the results are almost the same as those of conventional chemical synthetic surfactants.
- biosurfactants are used in most of the various industries where chemical synthetic surfactants are used, including pharmaceuticals, food, cosmetics, detergents, secondary recovery of crude oil, the filter and paper industry, the cleanup of oil pollution on land and sea, and the breakdown of milk fat in treatment tanks. It has also been reported that the lamnolipid-biological surfactants produced from Pseudomonas sp. Can be used as a new field of biomedical medicine because they alter cell surface morphology and exert inhibitory effects on pathogens. Therefore, studies on biological surfactants having such advantages have been actively conducted worldwide, and many kinds of biological surfactants have been reported.
- Pseudomonas sp Extracting common biological surfactant compounds status, including alarm Norris feed from the culture broth by measured the inhibitory effect on various pathogenic bacteria in a result certain pathogens: conventional antibiotics against (acne causing bacteria ⁇ Propionibacter ium acnes, Staphylococcus aureus) and It was confirmed that it has an excellent inhibitory effect when compared. In addition, it has been confirmed that it has a bactericidal effect at low concentrations against various pathogens and based on these results, it is environmentally friendly and bio-friendly to cope with methyl paraben, which has been used as a cosmetic preservative but is reported to be dangerous to humans.
- the present inventors have tried to develop a preservative composition derived from natural substances that can effectively inhibit the growth of microorganisms to increase the shelf life of cosmetics or food.
- a preservative composition derived from natural substances that can effectively inhibit the growth of microorganisms to increase the shelf life of cosmetics or food.
- Pseudomonas aeruginosa culture extract exhibits an antimicrobial effect on various bacteria and that the Pseudomonas aeruginosa extract of the present invention can be used as a cosmetic preservative and food preservative by replacing cosmetic preservatives of synthetic parabens.
- the invention was completed.
- an object of the present invention to provide an antiseptic composition comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- Another object of the present invention to provide an antibiotic composition comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- Another object of the present invention is to provide a composition for preventing or treating acne comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- Still another object of the present invention is to provide an antioxidant composition comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- Another object of the present invention is to identify the active ingredient causing the antimicrobial effect of Pseudomonas aeruginosa culture extract.
- Other objects and advantages of the present invention are as follows.
- the present invention provides an antiseptic composition comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- the present invention provides an antibiotic composition comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- the present invention provides a composition for preventing or treating acne comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- the present invention provides an antioxidant composition comprising the Pseudomonas aeruginosa culture extract as an active ingredient.
- the present inventors have tried to develop a preservative composition derived from natural substances that can effectively inhibit the growth of microorganisms to increase the shelf life of cosmetics or food.
- Pseudomonas aerugi nosa culture extract exhibits antibacterial effect on various bacteria including skin flora and acne-inducing bacteria, and the extract of Pseudomonas aerugi nosa replaces the cosmetic preservatives of synthetic parabens. It has been confirmed that it can be used as a preservative and food preservative.
- composition of the present invention comprises Pseudomonas aeruginosa culture extract as an active ingredient.
- Pseudomonas aeruginosa culture extract means that it is obtained by extracting from a culture medium that cultured P. aeruginosa.
- the Pseudomonas aeruginosa culture extract of the present invention comprises a rhamnol ipid, which is a biosurfactant (bi osurfactant).
- the rhamno lipids included in the composition of the present invention are di-rhamno lipids represented by the following Chemical Formula 1 or mono-rhamno lipids represented by Chemical Formula 2:
- the Pseudomonas aeruginosa culture extract has a different structure of rhamnolipid, among which the Rhamnolipid of Formula 1 or 2 has a significantly higher antimicrobial activity as compared to other Rhamno lipids extracted from the Pseudomonas aeruginosa culture extract.
- the Pseudomonas aeruginosa culture extract of the present invention is inoculated with Pseudomonas aeruginosa and cultured to obtain a supernatant by centrifugation of the culture medium and precipitated by adding hydrochloric acid solution to the supernatant, followed by centrifugation again. Only a precipitate is obtained, which is obtained by adding ethyl ether to the precipitate and then separating and concentrating only the ethyl ether layer.
- the extract of the present invention includes not only those obtained by using the solvent described above, but also those obtained by additionally applying a purification process thereto. For example, fractions obtained by passing the extract through an ultrafiltration membrane having a constant molecular weight cut-off value, separation column by various chromatography (manufactured for separation according to size, charge, hydrophobicity or affinity), and various additionally performed The fraction obtained through the purification method is also included in the extract of the present invention.
- the extract of the present invention may be prepared in powder form by an additional process such as distillation under reduced pressure and freeze drying or spray drying.
- the content of the Pseudomonas aeruginosa culture extract in the composition of the present invention is 0.01 part by weight based on 100 parts by weight of the total composition.
- the content of the Pseudomonas aeruginosa culture extract in the composition of the present invention is 0.01-0.5 parts by weight based on 100 parts by weight of the total composition.
- the content of the Pseudomonas aeruginosa culture extract in the composition of the present invention is 0.02-0.1 part by weight based on 100 parts by weight of the total composition.
- the composition of the invention has antibacterial and / or antifungal activity.
- the compositions of the present invention exhibit a wide range of antibiotic activity against a variety of microorganisms, in particular bacteria, fungi and yeast.
- the composition of the present invention is a genus Staphyl ococcus, Bacillus (Bac i 1 lus) genus, Genus Pseudomonas, Candida genus, Propionibacterium genus, Streptococcus genus, Proteus genus, Corynebacterium genus, Enterococcus genus It exhibits antibiotic activity against at least one bacterium selected from the group consisting of the genus Klebsi el la and Escherichia coli.
- the composition of the present invention has a high antioxidant effect, such as ascorbic acid (AA), a representative component having an antioxidant effect at a concentration of 0.53 ⁇ 4 or more.
- AA ascorbic acid
- the antiseptic / antibiotic composition of the present invention having a broad spectrum of antibiotics and an antioxidant effect is widely used to achieve the purpose of antimicrobial, sterilization, disinfection, antiseptic, etc. in cosmetics as well as food, household goods, pesticides and medicines. Can be.
- the antiseptic composition of the present invention may be prepared as a cosmetic composition.
- the composition of the present invention is prepared with a cosmetic composition
- Pseudomonas aeruginosa culture extract can be used in place of cosmetic preservatives because it prevents the cosmetic composition from being altered by bacteria.
- the composition of the present invention is made of a cosmetic composition
- the composition of the present invention may include the components commonly used in cosmetic compositions, as well as the Pseudomonas aeruginosa culture extract, salts thereof, or solvates or hydrates thereof.
- conventional adjuvants such as antioxidants, stabilizers, solubilizers, vitamins, pigments and flavors, and carriers.
- the antiseptic composition of the present invention may be prepared as a food composition.
- Pseudomonas aeruginosa culture extract may be used in place of a food preservative because it prevents food from being altered by bacteria.
- the composition of the present invention is made of a food composition, as an active ingredient, as well as extracts of Pseudomonas aeruginosa culture medium, the components commonly added during food production, for example, protein carbohydrates, fats, nutrients, seasonings and flavoring agents It includes.
- the above carbohydrates include monosaccharides such as glucose, fructose and the like; Disaccharides such as maltose, sucrose, oligosaccharides and the like; And conventional sugars such as polysaccharides, for example, textulin, cyclotextin and xyl, and sugar alcohols such as sorbitol and erythritol.
- natural flavoring agents [tauumatin, stevia extract (for example, rebaudioside A, glycyrrhizin, etc.) and synthetic flavoring agents (saccharin, aspartame, etc.) can be used.
- synthetic flavoring agents sacharin, aspartame, etc.
- citric acid, liquid fructose, sugar, glucose, acetic acid, malic acid, fruit juice, bilayer extract, jujube extract, licorice extract, etc. may be further included. have.
- antibiotic composition refers to a composition containing antibiotics that kill or inhibit growth of microorganisms, including viruses, fungi, protozoa, and bacteria. Means.
- the antibiotic substance has antibiotic activity, that is, antibacterial activity, antifungal activity or antiviral activity.
- composition of the present invention has a significant effect on the prevention and treatment of skin infections or acne caused by the bacteria.
- the composition of the present invention is a well known propionibacterium acne and gram-positive bacteria Staphylococcus aureus Bacillus cereus, Gram-negative bacteria Pseudomonas aerozinosa, Significantly inhibit the growth of several bacteria, such as Candida albicans.
- composition for preventing or treating acne of the present invention may be prepared including a cosmetically effective amount of the Pseudomonas aeruginosa culture extract, which is the above-mentioned effective ingredient of the present invention, and a cosmetically acceptable carrier.
- the term “cosmetic effective amount” means an amount sufficient to achieve antibiotic efficacy against the microorganism of the composition of the present invention described above.
- the external preparation composition for skin of the present invention may be prepared in any formulation commonly prepared in the art, for example, solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing It may be formulated as a cleansing, oil, powder foundation, emulsion foundation, wax foundation, spray, and the like, but is not limited thereto. More specifically, flexible It can be prepared in the form of a lotion, nourishing lotion, nourishing cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
- the carrier components include animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide. Can be used.
- lactose When the formulation of the present invention is a powder or spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, and in particular, in the case of spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.
- a solvent, solubilizer or emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 , 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan and fatty acid ester.
- liquid carrier diluents such as water, ethanol or propylene glycol, sucrose isostearyl alcohol, suspending agents such as polyoxyethylene sorbitan esters and polyoxyethylene sorbitan esters, Microcrystalline cellulose, aluminum metahydroxy, bentonite agar, tracant and the like can be used.
- the formulation of the present invention surface-active agent-containing cleansing the case of an aliphatic alcohol sulfate as carrier components, aliphatic alcohol ether sulfate, sulfosuccinate monoesters. Isetionates, imidazolinium derivatives, methyltaurates, sarcosinates, fatty acid amide ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acids Esters and the like can be used.
- ingredients included in the external preparation composition for skin of the present invention in addition to the active ingredient and the carrier component, the components commonly used in the external preparation composition for skin And conventional adjuvants such as, for example, antioxidants, stabilizers, solubilizers, vitamins, pigments and flavorings.
- the present invention provides an antiseptic and antibiotic composition comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- the present invention provides a composition for preventing or treating acne comprising Pseudomonas aeruginosa culture extract as an active ingredient.
- composition comprising the Pseudomonas aeruginosa culture extract of the present invention exhibits a broad antimicrobial spectrum and a high antioxidant effect against a variety of bacteria, and the composition is applicable to cosmetic compositions such as cosmetics, as well as food, pharmaceuticals, pesticides and household goods. It can be usefully used for antibacterial, antiseptic and antiseptic purposes in various fields such as.
- the active ingredient causing the high antimicrobial effect of the Pseudomonas aeruginosa culture extract of the present invention was found to be the rhamnolipid of a specific structure (Rha CIO CIO, Rha Rha CIO CIO) among various lamnolipids, through which Increased efficiency for industrial applications.
- Figure 2 is a graph showing cfu as a result of the challenge test (challenge test) for the product of the toner formulation containing Pseudomonas aeruginosa culture extract.
- Figure 3 is a photograph showing the appearance after plate plating when the antiseptic test for the product of the toner formulation containing Pseudomonas aeruginosa culture extract.
- Figure 4 is a result of measuring the acne-related trouble improvement rate depending on the concentration of Pseudomonas aeruginosa culture extract (red bar means balm formulation, purple bar means cream formulation).
- 5 is a result of acne-related problems after applying the composition of the present invention containing Pseudomonas aeruginosa culture extract on the skin of the subject through photographing.
- 6 is a view showing the structure of rhamnose and rhamnolipid.
- Figure 7 shows the results of the analysis of the rhamno lipid through the ID 1H-NMR spectrum.
- 8 shows the results of rhamnose proton analysis.
- 15 is a structural analysis result of the active ingredient peak 1, peak 2 using LC-MS, LOMS / MS.
- strain Prior to the experiment strain (CJM01) was selected. As a result, it was found that it was Pseudomonas aeruginosa, and the strain was identified as M9 medium (CaCI 2 .015 g / L, Na 2 HP0 4 6 g / L, KH2PO4 3 g / L, NaCl 0.5 g / L, NH 4 C1 1 g / L). , MgS0 4 0.0625 g / L, Glucocose 20 g / L) was incubated for 72 hours at 37 ° C. After the culture, the culture solution was centrifuged to obtain a culture medium in which cells were completely removed.
- M9 medium CaCI 2 .015 g / L, Na 2 HP0 4 6 g / L, KH2PO4 3 g / L, NaCl 0.5 g / L, NH 4 C1 1 g / L.
- the culture medium from which the cells were removed was lowered to pH 2 using HCL and then precipitated at 4 ° C. for one day.
- the precipitate was centrifuged again to remove the supernatant and only the precipitate was obtained.
- the precipitate was extracted with ethyl ether, and only the ethyl ether layer was separated, concentrated with a rotary evaporator, and the extract (biosurfactants crude) obtained by evaporating all ethyl ethers was named R1.
- Bertani Bertani
- Bertani tryptone 10 g / L, NaCl 10 g / L, yeast extract 5 g / L
- each bacterial culture 200 y 1 was plated on LB agar plates.
- R1 extracted from the microbial aeruginosa culture was dissolved in methanol at a concentration of 2 mg / ml, and Methyl Paraben, Phenoxy Ethanol, and Naturot ics were used as a control. In a concentration of 10 mg / ml.
- Dissolved R 1, methylparaben, phenoxyethanol, and netotics solutions were each 20 ⁇ 1 on a paper disc (diameter: 6 mm), and then the paper disc was sufficiently dried. Paper discs were then placed on agar plates smeared with aureus, B. cereus, P. aeroginosa and E. coli. Each agar fulate was incubated for 18 hours at 37 ° C aerobic conditions. After 18 hours the clear zone created around the paper disc was observed.
- R1 dissolved in methanol was added to the prepared toner formulation so that the final concentration of R1 was 0%, 0.01%, 0.05%, and 0.1%, and each container was inoculated with 5.
- aureus and B. cereus cultures also had to be by the addition of methyl paraben is dissolved in methanol in the toner formulation has a final concentration of methyl paraben 0%, 0.1%, 0.5%, 1% to 61 respectively of the container.
- aureus, B. cereus cultures were inoculated. The number of inoculum was 10 6 -10 7 cfu (colony forming unit) / ml.
- each toner was diluted 1, 3, 5, and 7 days immediately after inoculation, and 200 ⁇ 1 smeared on an LB agar plate to calculate the number of cells. Comparison was made to determine whether death occurred. As a control, only methanol was added to the toner formulation and inoculated with the culture medium, followed by repeated experiments.
- R1 and methylparaben dissolved in methanol were added to the prepared toner formulation, respectively, so that the final concentration was 0%, 0.1%, 0.5%, and each container was inoculated with P. aeruginosa and C. albicans cultures.
- the number of inoculum was 10 6 -10 7 cfu (colony forming unit) / ml.
- the toner inoculated with P. aeruginosa was stored on the LB agar plate after 1 to 3 days, 5 days and 7 days after inoculation. Toner was counted by 200 ⁇ 1 smears on YPD agar plates and counted The mortality was checked by comparison with the initial inoculation. As a control, only methanol was added to the toner formulation and inoculated with the culture medium, followed by repeated experiments.
- R1 and methylparaben dissolved in methanol were added to the prepared lotion formulation so that the final concentration was 0% and 0.5%, respectively.
- the lotion inoculated with S. aureus, B. cereus, and P. aeruginosa was stored at room temperature and stored at room temperature immediately after inoculation, 1, 3, 5, 7 days. Lotions inoculated with C.
- albicans were plated on 200 ⁇ l plates of YPD agar plates to calculate the number of cells.
- composition of cream formulation product containing 0.02% of R1 mixture Ingredients g% Witch Hazel Water 18.49 36.98 Golden Jojoba Oil 3 6 Evening Primrose Oil 2.5 5 Rib Emulsion Wax 2.5 5 Aloe Vera Leaf Extract
- Centella asiatica Extract 6 6 Tocopheryl Acetate 1 2 Tea Tree Essential Oil 0.5 1 Grapefruit Essential Oil 0.5 1 Natural Herbal Preservative 0.5 1
- Centella asiatica Extract 6 6 Tocopheryl Acetate 1 2 Tea Tree Essential Oil 0.5 1 Grapefruit Essential Oil 0.5 1 Natural Herbal Preservative 0.5 1
- the purpose of this study was to evaluate the efficacy and safety of the acne-related problems such as improving symptoms when applying the product to subjects with acne-related problems.
- the primary end point is the symptom improvement rate of acne-related problems after 2 weeks after the use of the product, and evaluated whether the symptom improvement rate of acne-related problems before and after the test differs. Based on past clinical trials, the total number of subjects was 30 in consideration of the dropout rate of about 10%. Three individuals who did not sign a clinical trial consent for personal reasons did not participate in the trial, and the total participants participated in the trial. There were 27 subjects with a median dropout rate of 0%. The final number of subjects was 27.
- test product Use 5 g of the test product every two weeks, and apply cream or chestnut product to the skin lesions designated by the investigator at least twice a day (morning, evening and regular) for two weeks.
- Subjects who met the selection criteria and those who used the product provided for 2 weeks were selected as the subjects of the evaluation, and a visual assessment was performed on acne-related problems, such as identifying the number of acne in progress and taking images at weeks 0, 1, and 2 weeks.
- a questionnaire containing subjective opinions was conducted. Results summary and analysis of the test were analyzed by statistical estimation.
- SIGMA containing 90% of R2, R3 and rhamnolipid obtained by changing the culture and extraction methods of P. aeruginosa, such as biological surfactant R1 extracted from a microorganism (.aeruginosa) culture medium.
- R90 purchased from ALDRICH was analyzed.
- the structure of the rhamnolipid consists of a lipid moiety comprising one or two rhamnose (sugar) moieties (left of FIG. 6) and two aliphatic chains (al iphat i c chains) (right of FIG. 7).
- the diversity of the rhamnolipid structure is due to the number of one or two rhamnose rings and the structure (length and saturation) of the two aliphatic chains of the lipid moiety.
- Antioxidant effect was tested for the application of Pseudor nas aeruginosa culture extract as a preservative.
- DPPH radicals are purple, which is yellow when reacted with antioxidants.
- the change in color of DPPH radicals becomes more pronounced.
- R1 ascorbic acid (Ascorbi c acid, AA) and methyl paraben (MTP) were dissolved in methanol at different concentrations. So obtained Samples (100 ⁇ ) were mixed with 100 ⁇ 1 of DPPH radical solution dissolved in methanol at a concentration of 0.006% each to make a total of 200 ⁇ and reacted for 30 minutes in a light-blocked space. After reaction was completed, the absorbance value of each mixture was measured at 517 nm to determine the antioxidant capacity of each sample.
- Pseudomonas aeruginosa culture extract is a mixture of several components, not a single component.
- An experiment was conducted to find out the active ingredient causing the antimicrobial effect among the various components included in the extract of P. eudonionas aeruginosa culture and to identify its structure. Isolation of R1 in a Mixture Extracted from P. aeruginosa Cultures
- Microorganism 0 °. 1 mg of mixed Rl extracted from aeruginosa) culture was dissolved in methanol and injected into a sep-Pak vac lcc tcl8 cartridge column. The column was then washed with solvent A and solvent B, the developing solvent, was injected. The solvent B was injected into the column differently, and the fractions passed through the column were collected and named as fraction 1, fraction 2, fraction 3, fraction 4, fraction 5, and fraction 6. The concentrations of solvent B were 50%, 55%, 60%, 65%, 70%, 75%, respectively, injected into the column, and the composition of solvent A and solvent B is shown in Table 11. Table 111
- the obtained fractions were dried and dissolved in methanol at a concentration of 10 mg / ml. 20 ⁇ of each fraction dissolved in methanol is removed. After dropping onto the plated agar plate was incubated at 37 ° C. for 18 hours and the resulting clear zone on the agar plate was observed after 18 hours.
- the scanning mass range was prepared at 75-1000 m / z. MS / MS was carried out for specific components causing the antimicrobial effect.
- the mixed biological surfactant extracted from the culture medium of microorganism was named R1 and Gram-positive pathogenic bacteria (Ya3 ⁇ 43 ⁇ 4F 7 «? CaAS aureus, Bacillus cereus), 3 ⁇ 4 " ⁇ 3 ⁇ 43 ⁇ 4 ⁇ 5 " (Pseudomonas Antifungal test was performed on aeroginosa and Escherichia co //).
- Rl produced significantly larger clear zones at concentrations five times less than methyl parabens, phenoxyethanol, and naturotics used as cosmetic preservatives. (FIG. 1).
- R1 killed 99.9% of the inoculated bacteria in 7 days for all the inoculated bacteria in toner formulations.
- R1 was Gram-positive pathogenic bacteria Staphylococcus aureus, Bacillus at 0.01%, 10 times less than methyl paraben.
- 99.9% of the inoculated bacteria were killed in one day.
- Gram Negative pathogenic bacteria (/! Sez / obwo / s aeroginosa) ⁇ fungi ( ⁇ /? ⁇ albicans killed 99.9% of the inoculated bacteria in 5 days at 0.5%, the same concentration as methylparaben (Fig. 2-3).
- R1 killed 99.9% of the number of cells inoculated within 7 days at 0.5%, the same concentration as methyl paraben (Table 12), for all bacteria inoculated in the route formulation (Table 12). .
- the number of advanced acne present in the lesion area determined by the investigator before the product was applied at the 0th day of the clinical trial was set as the starting point, and the degree of improvement by the eyes after 2 weeks after the examination was quantified. Higher rates of improvement were seen in subjects using products containing microbial culture extracts as compared to products containing no culture extract. In particular, the highest rate of improvement was found in the subjects who used cream products containing 0,02% of microbial culture extracts, followed by high rates of improvement in subjects who used cream products containing 0.01% of microbial culture extracts. This was confirmed (FIG. 4). Based on this, natural cosmetics containing the microbial culture extract prepared by the present inventors can be judged to help to improve acne. The imaging results of the subjects are as shown in FIGS. 5A-5I.
- the portion corresponding to rhamno lipid in the ID 1 H-NMR spectrum for sample 1 is shown in FIG. 7.
- the integral s is shown below the spectrum.
- All signal intensities were normalized to methyl peaks at 0.82 ppm, corresponding to six protons (two methyl groups). Thus, the proton peak seems to have a signal intensity of about 100 units.
- the peaks in the two groups at 1.4-1.5 ppm and 2.4-2.6 ppm show signal intensities of ⁇ 400 and four protons in the C 2 3 ⁇ 4 IC 5 H 2 and C 7 H 2 I CioH 2 groups, respectively. Matches the signal.
- the mass ratio of mono and di-rhamnolipids can be measured by comparing the intensities of the signals obtained from the lipid and rhamnose groups.
- HI and H4 lipid protons represent the same type of signals, the sum of their intensities being approximately 100, which means that each of the rhamnolipid molecules in the complex is exactly of this type. It means having one proton.
- the sum of signal intensities obtained from HI '/', H272 ", H373", H575 "rhamnose protons is higher than expected in the mono-rhamnolipid complex.
- One HI 'proton per molecule in the rhamnolide complex should have a signal of 100.
- Three protons of H2' H3 'and H5' should have a signal of 300. These signal intensities were measured to be approximately 150-480. From these signal intensities, it can be estimated that about 60% of the die-rhamno lipid is present in sample 1. Similar analysis shows that sample poles 0, 2, 3 and 90 are 1D. Performed via 1 H-NMR spectra.
- the systems were pre-assigned to the type of rhamnose moiety (the first (') or the second (") single ring structure of the di-rhamnose) and the position of the hydroxyl fatty acid (directly or indirectly associated with the rhamnose, 6) is Based on known chemical shifts (Part 3, 2D-NMR analysis, illustration of FIG. 9).
- Systems 1 and 2 were assigned to the second rhamnose ring structure of the di-rhamnose, and systems 3 and 4 were assigned to the first rhamnose ring structure of the di-rhamnose.
- Systems 5 and 6 correspond to the rhamnose ring structure of the genus mono-rhamnolipid.
- ID 1 H-NMR spectra clearly shows the relative density of rhamnose in the sample poles (FIG. 11). The same results were observed for fatty acid systems. Relative density of ⁇ - ⁇ molecules by using signal strength The signal intensity was measured by ID 1H MR spectra to obtain well separated signals assigned to H1 / H1 "and H2 / H2" rhamnose protons, Hi and H4 fatty acid protons. A summary of the analysis is presented in Table 16.
- fraction 1, fraction 2 and fraction 3 showed antimicrobial activity comparable to that of R1, fraction 4 and fraction 5 showed relatively weaker antimicrobial activity than fraction R1. Did not show antimicrobial activity (FIG. 13). All samples were subjected to LC analysis. As a result, two common peaks were found in fraction 1, fraction 5 and fraction 5 which were high in fraction 1, fraction 2 and fraction 3, which showed antimicrobial activity. 2 was designated (FIG. 14). In connection with the antimicrobial activity test, the presence of peak 1 and peak 2 was determined to determine the antimicrobial activity.
- the peak 1 has a molecular weight of 650 and R a- Di-rhamnol ipids with the structure of Rha-C10-C10 were analyzed, and peak 2 was mono-rhamnol with the molecular weight of 504, R a-C10-C10. ipid) (FIG. 15A-D).
- R1 there is a lamnolipid having various structures (FIG. 16, Table 18), among which Rha-Rha-C10-C10 and Rha-C10-C10 are identified as active ingredients having antimicrobial activity. It was.
- Z 3 purchased from Sigma Aldrich Korea.
- the antimicrobial activity of rhamnolipids (R90, R95) extracted from aeruginosa culture against aureus was significantly lower than that of R1 (Fig. 17).
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Abstract
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EP15809320.3A EP3192519A4 (en) | 2014-06-20 | 2015-06-02 | Composition containing pseudomonas aeruginosa culture solution extract having antibiotic and antiseptic activities, and use thereof |
US15/320,252 US20170143771A1 (en) | 2014-06-20 | 2015-06-02 | Composition containing pseudomonas aeruginosa culture solution extract having antibiotic and antiseptic activities, and use thereof |
CN201580033165.1A CN106794200A (zh) | 2014-06-20 | 2015-06-02 | 包含具有抗菌及防腐活性的绿脓杆菌培养液提取物的组合物及其的用途 |
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BE1005704A4 (nl) * | 1992-02-04 | 1993-12-21 | Piljac Goran & Piljac Visnja | Farmaceutisch preparaat op basis van rhamnolipide. |
KR20010038285A (ko) * | 1999-10-23 | 2001-05-15 | 채문식 | 신규의 항진균성 활성을 갖는 슈도모나스 에루지노사 비5 및 이 균주로부터 생산되는 항생물질의 제조방법 |
KR20080108886A (ko) * | 2007-06-11 | 2008-12-16 | 아사히 프리텍 가부시키가이샤 | 금속 회수장치 |
US8106370B2 (en) * | 2009-05-05 | 2012-01-31 | General Electric Company | Isotope production system and cyclotron having a magnet yoke with a pump acceptance cavity |
CN103202295B (zh) * | 2010-03-30 | 2015-01-07 | 湖州紫金生物科技有限公司 | 一种鼠李糖脂作为生物农药和生物杀虫剂的应用 |
CN101845468B (zh) * | 2010-03-30 | 2012-11-14 | 湖州紫金生物科技有限公司 | 一种鼠李糖脂的制备方法及其应用 |
KR20120110292A (ko) * | 2011-03-29 | 2012-10-10 | 창원대학교 산학협력단 | 메티실린 내성 황색포도상구균에 대해 유효한 항생물질을 생산하는 슈도모나스 애루기노사 kacc91592p 균주 |
KR101339907B1 (ko) * | 2011-09-14 | 2013-12-10 | 보은군 | 대추 재배를 위해 사용될 수 있는 계면활성제의 생산능이 있는 슈도모나스 에루지노사 Ab7 및 이를 이용한 계면활성제의 생산방법 |
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2015
- 2015-06-02 US US15/320,252 patent/US20170143771A1/en not_active Abandoned
- 2015-06-02 EP EP15809320.3A patent/EP3192519A4/en not_active Withdrawn
- 2015-06-02 CN CN201580033165.1A patent/CN106794200A/zh active Pending
- 2015-06-02 WO PCT/KR2015/005535 patent/WO2015194772A2/ko active Application Filing
Also Published As
Publication number | Publication date |
---|---|
EP3192519A4 (en) | 2018-03-14 |
CN106794200A (zh) | 2017-05-31 |
EP3192519A2 (en) | 2017-07-19 |
US20170143771A1 (en) | 2017-05-25 |
WO2015194772A3 (ko) | 2016-02-11 |
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