• 专利附录
  • 专利说明
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  • 类似技术
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    • 专利摘要:
    Composite with antimicrobial activity comprising two self-assembled components of natural origin and, optionally, a component (c) of nanometric size. A composite material formed by an oligomer component (a) and a component (b) with phenolic compounds, where both components are of natural origin, exhibit antimicrobial activity and anti-adhesive properties against microorganisms, are biocompatible and do not present cytotoxicity to the cells of the mammals. Optionally, the composite material may comprise a nanometer-sized component (c). Preferably, a composite material formed by oligomers of propyl chitosan and, optionally, nano-sized silver. Method of synthesis of a composite material comprising at least two of the components (a), (b) and (c) by sonication processes. Use of the composite material to prevent, reduce, control or eliminate any type of microorganism or pathogen. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2568698A1
    申请号:ES201431591
    申请日:2014-10-30
    公开日:2016-05-03
    发明作者:Jesús Martín Gil；Mercedes SÁNCHEZ BASCONES；Salvador Hernández Navarro；Eduardo Pérez Lebeña；Pablo Martín Ramos；Cassyo DE ARAÚJO RUFINO；Petruta Mihaela MATEI
    申请人:Universidad de Valladolid；
    IPC主号:
    专利说明:

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    It is especially preferred that component (B) be a propolis extract with a 10% by weight concentration of polyphenols and flavonoids, propolis preferably from Burgos, Cuenca del Duero, Spain. In particular, the propolis extract obtained as described in the examples section of this application. Thus, the composite of the invention can be obtained by mixing the extract described in this application with the chitosan solution in the ratio 1: 1, or 1 mg / L of propolis with a 1mg / L of chitosan
    As mentioned above, the composite material of the invention may also comprise aloe vera as component (B), a product generally comprising a content of 1% by weight in polyphenols and flavonoids. In this case, the composite of the invention preferably comprises an aloe vera / chitosan ratio of 10: 1, or 10 mg / L of aloe vera with 1 mg / L of chitosan.
    It is also possible to use pure extracts of commercially available polyphenols or flavonoids and mix them directly with the oligomeric component (A), in particular chitosan oligomers, preferably in the proportion 10% in w / v of polyphenol or flavonoid and 90% in p / v of the oligomer. For example, the pure product or active component isolated from the propolis or phenethyl ester of caffeic acid (CAPE) can be purchased, although other active ingredients derived from phenolic acids, polyphenols can also be used
    or of flavonoids and used by mixing in the proportions recommended above with the oligomer, preferably chitosan. However, and preferably, it is recommended in the present invention to operate with natural products, above all for the cost savings that this represents.
    In especially preferred embodiments of the present invention, the composite or composite material comprises a component (A) formed by chitosan oligomers with a maximum molecular weight 6000 g / ml, and propolis as component (B), preferably propolis extract with a content of polyphenols and flavonoids between 5 and 15% by weight. This composite material has an antifungal activity superior to its components separately. Additionally, it is soluble in water, and can also be manufactured as a coating or film and thus offer greater protection.
    In other further preferred embodiments, the composite material described in this patent application comprises a component (C) of nanometric size, that is, particle size between 1 to 150 nm. Preferably, between 40 and 150 nm, since below 40 nm the chemical element or species has a very high activity and can be toxic to the cell. This component (C), whether chemical element or species, can be of inorganic origin such as oxide, metal or fluoride, but it can also be of organic origin, for example, a synthetic nanopesticide.
    In even more perferred embodiments, the nano-sized component (C) is inorganic. Preferably, it is selected from the group consisting of silver, copper, arsenic, titanium oxide, silica and graphene material.
    In especially preferred embodiments, the composite or composite material of the present invention comprises a component (A) formed by chitosan oligomers with a maximum molecular weight 6000 g / ml, a component (B) that is propolis, preferably propolis extract with a content of polyphenols and flavonoids between 5 and 15% by weight, and silver of nanometric size, preferably with a particle size between 40 and 150 nm, as component (C). This composite material has a greater antifungal or antimicrobial activity due to the incorporation or integration of the nanomaterial, and also has a greater bactericidal power than the separate or associated components of two
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    a) obtaining a solution of a component (A) formed by oligomers of maximum molecular weight 6000 g / mol, preferably between 2000 g / mol and 6000 g / mol;
    b) obtaining a component (B) comprising one or more phenolic compounds, preferably flavonoids or polyphenols; Y
    c) mix the oligomer solution of step a) with the phenolic compounds of step b) and sonicate for at least one minute.
    In the method described in this patent application, obtaining the oligomeric component (A) and the component (B) comprising one or more phenolic compounds is carried out independently. Therefore, steps a) and b) can be carried out in any order or simultaneously.
    In even more preferred embodiments, when the composite material of the invention comprises a chitosan and propolis oligomer, the synthesis method of the present invention comprises:
    a) obtaining a solution of a component (A) formed by oligomers of maximum molecular weight 6000 g / mol, preferably between 2000 g / mol and 6000 g / mol;
    b) obtain a phenolic extract of propolis, preferably with a content between 5 and 15% of flavonoids and polyphenols; Y
    c) mix the oligomer solution of step a) with the phenolic extract of step b) and sonicate for at least one minute.
    Chitosan oligomers can be produced by oxidative degradation of commercial chitosan. For this, microwave radiation methods can be used, for example [Sun T., Zhou D., Xie J., Mao F. 2007. Preparation of chitosan oligomers and their antioxidant activity. Eu. Food. Res. Technol. 225: 451-456].
    However, in the method of the present invention, in order to decrease degradation times, oligomers are produced by sonication. In particular, chitosan oligomers can be obtained by acid hydrolysis from a chitosan solution in the presence of a clean and affordable oxidizing agent such as, for example, hydrogen peroxide. The hydrolysis is carried out with stirring with an ultrasonic equipment that operates at a frequency of 20 kHz. The sonication can be performed for 3-6 periods of 5 minutes each, depending on the quality of the starting chitosan, not allowing the solution to heat above 60 ° C. As sonication periods increase from 3 to 6, temperatures from 30 to 60 ° C and H2O2 concentrations from 0.3 to
    0.6 M, it is possible to reduce the PM of the oligomers from 6000 to 2000 g / mol, being optimal to obtain oligomers of 2000 g / mol.
    After heating or sonicating for 30 minutes, it is removed, for example, by centrifugation.
    or decanting, any water insoluble material. The pH is subsequently adjusted to 8-9, for example, using a 25% solution of potassium methoxide in methanol. Then, the material can be isolated from the solution and dried, preferably under vacuum at 20 ° C. The quality of the oligomers obtained can be determined by Fourier transform infrared spectrometry (FTIR). In this way oligomers with a molecular weight between 2000-6000 g / mol can be obtained. Size that can be reduced in the sonication process of the later stages of the synthesis method, preferably reaching a maximum size of 2000 g / mol in the composite of the invention.
    Aqueous solutions of chitosan oligomers, preferably of concentration 0.005 0.01 M or solutions of 1.25-2.5% w / v can be prepared from a solution of chitosan oligomers of PM 6000-2000 g / mol in 0.5% AcOH and pH 4-6. The chitosan / acetic acid / water mixture is sonicated for at least one minute and allowed to stir for at least 12 hours, so that the solution is stabilized and a clear solution of chitosan is obtained. The solutions are stable in an inert atmosphere and cold at 4-10 ° C, at pH between 4-6.
    In preferred embodiments of the present invention, the propolis is used as an ethanol extract of propolis. This extract can be obtained by crushing the starting propolis to fine powder and subsequent extraction, for example, using a 7: 3 hydroalcoholic solution. Other stages of the extraction procedure may be dynamic maceration, percolation, filtration and concentration of the resulting solution.
    In the method described in this patent application, the obtaining of the chitosan oligomers and the ethanol propolis extract is carried out independently. Therefore, these stages can be done in any order or simultaneously.
    Once the solution of chitosan oligomers of step a) and the ethanol extract of propolis of step c) is obtained, the mixing of both solutions is preferably carried out by adding the alcoholic extract of propolis on a solution of chitosan in water.
    As mentioned above, the composite of the present invention can be a coating or film that can be used to treat, for example, crops, seeds, wood, stone, etc. In these preferred embodiments, firstly an adhesive material or film of the oligomer, preferably chitosan oligomer, is obtained, which is subsequently incorporated into the rest of the components of the composite.
    When the composite material described in this patent application is in the form of a coating or film, the synthesis method of the invention comprises cross-linking the oligomers in situ in the presence of a cross-linking agent, preferably glycerin or glyoxal, prior to its mixing with component (B) comprising phenolic compounds, or with component (C) of nanometric size.
    In even more preferred embodiments, this cross-linking step takes place in the presence of a surfactant, in particular Tween 20, to improve the adhesion properties of the oligomer solutions.
    In preferred embodiments, to produce a composite coating or film comprising chitosan / nanoplate, chitosan / propolis or chitosan / propolis / nanoplate, the chitosan oligomer solutions obtained as described above can be used, preferably with a concentration 1.25 -2.5% w / v and pH 4-6. These solutions can be treated with a 2-2.5% w / v glycerin (C3H803) solution or 4% v / v glyoxal. Additionally, Tween 20, preferably 0.050.1% (v / v), can be added in order to improve the adhesion properties of chitosan solutions.
    When glyoxal is used, the cross-linking process is immediate (less than 1 hour), while when glycerin is used, it takes several hours (or even days) to take. The cross-linking can depend on multiple factors, such as temperature, pH, sonication and / or stirring time and concentration of the solutions. In the synthesis method of the present invention sonication processes are used as activators of the cross-linking process, in this way the activation takes place in a maximum period of 1 minute, thus reducing the formation times of the films or coatings. Once the rest of the materials are incorporated into the composite, it can be applied by letting it rest on the surface to be treated between 1 minute and 1 hour in a dry atmosphere, to obtain optimum thicknesses of 0.3 to 0.6 mm.
    In other preferred embodiments, when the composite material comprises components (A), (B) and (C) as described in this patent application, the synthesis method comprises:
    a) obtaining a solution of a component (A) formed by oligomers of maximum molecular weight 6000 g / mol, preferably between 2000 g / mol and 6000 g / mol;
    b) obtaining a component (B) comprising one or more phenolic compounds;
    c) mixing the oligomer solution of step a) with the phenolic compounds of step b) and sonicating for at least one minute;
    d) obtain a stabilized solution of a component (C) of nanometric size; Y
    e) mixing the solution of the bicomposite material obtained in step c) with the solution of the nano-sized component (C) of step d) and sonicating for at least one minute.
    In even more preferred embodiments, when the composite material of the invention comprises chitosan, propolis and silver oligomers of nanometric size, the synthesis method of the present invention comprises:
    a) obtaining a solution comprising chitosan oligomers of maximum molecular weight 6000 g / mol, preferably between 2000 g / mol and 6000 g / mol;
    b) obtain a phenolic extract of propolis, preferably with a content between 5 and 15% of flavonoids and polyphenols;
    c) mixing the oligomer solution of step a) with the phenolic extract of step b) and sonicating for at least one minute;
    d) preparing a stabilizing solution of silver of nanometric size, preferably between 40 and 150 nm; Y
    e) mix the chitosan and propolis solution obtained in step c) with the nanometer-sized silver solution of step d) and sonicate for at least one minute.
    To obtain the composite material comprising the components (A), (B) and (C), in particular chitosan, propolis and silver of nanometric size, the three components are prepared separately. Next, the composite material comprising oligomers and phenolic compounds is obtained as described above. And then component (C) is incorporated.
    Step d) comprises the preparation of a stabilized silver solution of nanometric size, preferably 40 and 150 nm. In accordance with the synthesis method of the present invention, nanoplate stabilization is performed exclusively by sonication. However, there are other methods that allow obtaining silver nanoparticles by stabilizing the solutions with a 30 W UV lamp for 3 hours [Montazer,
    M. Shamei, A., Alimohammadi F. 2012. Synthesizing and stabilizing silver nanoparticles on polyamide fabric using silver-ammonia / PVP / UVC. Progress in Organic Coatings, 75 (4), 379385].
    The nanoplate preparation in the present invention can be carried out by first preparing an aqueous solution of AgNO3 and a reducing agent such as sodium citrate or ascorbic acid. Subsequently, the above solution is cooled and stirred at a temperature between 5 and 10 ° C. It is then deoxygenated with an inert gas, preferably abundant N2 for at least 30 minutes. The most delicate stage is the addition of a NaBH4 solution (hydrazine can also be used). This addition has been carried out in an inert medium, preferably under an N2 atmosphere, at a temperature between 5-10 ° C, at a very low rate of addition, preferably with a micropipette, and with a strong stirring of the solution. The first micro drop causes the colorless to yellow solution to turn and the increase in NaBH4, or successive drops, produces an intensification of the yellow to brown color, which can turn to light yellow by the addition of 10% H2O2 micro drops. The yellow color of the silver solution can be stabilized with polyvinylpyrrolidone (PVP) to prevent the addition of silver nanoparticles or any other chemical species present, and the application of ultrasound for 3-5 minutes with an ultrasound equipment of 20 kHz Finally, the pH is adjusted between 7-8, for example by adding 25% potassium methoxide in methanol. The solution should be left stabilizing for 24 hours in a refrigerator between 5 and 10 ° C.
    According to the described procedure, nanoplate solutions with a size of nanoparticles 40 and 150 nm, and a silver content in solution between 100 ppm and 200 ppm can be obtained. These solutions can be characterized by their absorption in a UV-Vis spectrophotometer at 420 nm. The solutions are stable in an inert atmosphere and cold at 4-10 ° C.
    Additionally, the method of the present invention also allows to obtain composite materials comprising components (A) and (C) as described in this patent application. This method comprises:
    a) obtaining a solution of a component (A) formed by oligomers of maximum molecular weight 6000 g / mol, preferably between 2000 g / mol and 6000 g / mol;
    d) obtaining a stabilized solution of a component (C) of nanometric size, preferably of size between 40 and 150 nm; Y
    e) mixing the oligomer solution of step a) with the solution of the nano-sized component (C) of step d) and sonicating for at least one minute.
    In preferred embodiments, the method of the present invention allows to obtain a composite material formed by nanometer-sized chitosan and silver oligomers, where the method comprises:
    a) obtaining a solution of chitosan oligomers of maximum molecular weight 6000 g / mol, preferably between 2000 g / mol and 6000 g / mol;
    d) obtain a stabilized solution of a silver nanometer size, preferably of size between 40 and 150 nm; Y
    e) Mix the chitosan oligomer solution from step a) with the nanometer-sized silver solution from step d) and sonicate for at least one minute.
    In preferred embodiments, the components (A) and (C) of the composite can be defined as described above in this patent application. Likewise, the preferred conditions of steps a), d) and e) are the same as those described above for the other variants of the method of the invention.
    In preferred embodiments of the present invention, once the solutions are obtained separately, binary mixtures in the 1: 1 ratio or ternary in the 1: 1: 1 ratio can be prepared. These can be mixed by always adding the solution containing the nanoplate over the solution containing propolis-chitosan, or chitosan in the case of obtaining the chitosan-nanoplate composite. The samples used to carry out the activity tests were prepared in the range 50 ug / ml to 900 ug / ml. For example it
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    Within the preservation and protection of plants and / or crops, the composite described in this patent application, in particular when it is formed by chitosan / propolis or chitosan / propolis / nanoplate can be used as a pesticide, in dressings and coatings for the protection and conservation of the agricultural and forestry environment as a whole, protection of crops and forest species.
    Within the protection of the industrial environment, the composite described in this patent application, in particular when it is formed by chitosan / propolis or chitosan / propolis / nanoplate, can be used in the protection and preservation of products, food and industrial facilities , preferably when the composite forms coating or film.
    In other preferred embodiments, the composite described in this patent application can be applied in the agro-forestry environment, as new nanopesticidal agents for the antimicrobial protection of plant and crop surfaces, seeds, wood, cellulose, food and agroforestry facilities such as silos, food industries and their facilities, wood and pulp industries and their facilities, etc. In Agriculture, the composite material of the present invention can be applied as nodulation factors, osmoprotective agents and antioxidants that benefit crop growth.
    In especially preferred embodiments, the present invention relates to the use of the composite described in this patent application, in particular when it is formed by chitosan / propolis or chitosan / propolis / nanoplate, as a fungicidal and / or bactericidal agent against:
     Tinder fungi in vines or Diplodia seriata;
     Red rice disease fungus, Bipolaris orizae;
     Bacteria and fungi of clinical interest. Preferably, bacteria selected from the group consisting of Staphylococcus aureus, Eschericia coli, Acinetobacter baumanii and Pseudomonas aeruginosa; u fungi selected from the group consisting of Candida albicans and Candida glabrata.
    Additionally, the present invention also relates to the use of a composite comprising components (A) and (C) as described in this patent application, preferably chitosan oligomers and nanometric silver as described in this patent application. in Agriculture to favor the growth of the seeds. BRIEF DESCRIPTION OF THE FIGURES
    Figure 1 (A) Bar chart of the percentage of fungal growth inhibition (PI) and (B) radial diameter of the mycelium D. seriata (Ø) per chitosan (A50), chitosan + propolis (B100), chitosan + propolis + nAg (3 mL) (C1), chitosan + propolis + nAg (6 mL) (C2), chitosan + propolis + nAg (1.5 mL) (D1), chitosan + nAg (3 mL) (D2), propolis + nAg ( 1.5 mL) (F1), propolis + nAg (3 mL) (F2), nAg (E), propolis (P) and control (T).
    Figure 2. Growth of the Diplodia seriata fungus in petri dishes and corresponding to mixtures A50, B100, C1, C2, D1, D2, F1, F2, B100, E and G); T = witness. The spots that appear on the petri dishes represent the discs of mycelium.
    Figure 3. Growth of the fungus Biporaris orizae in petri dishes. From left to right: control (maximum diameter Ø = 7.8 cm) and mixture D2 (chitosan + nAg 6 mL) with a radial diameter zero and for concentrations of 300, 600 and 900 µL / mL, respectively.
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    Treatments Concentrations (µl / ml)
    300 600900
    A50B100C1C2D1D2F1F2P 0 0 0 0 0 0 5.7 5.7 6.80 0 0 0 0 0 0 0 00 0 0 0 0 0 0 0 0
    Witness  7.4
    Figure 3 shows a radial diameter image of the control and different concentrations of D2 chitosan / silver samples in petri dishes. The sample to the
    5 left corresponds to the control and occupies practically the entire diameter of the plate, while the three plates on the right, corresponding to D2 mixtures of 300, 600 and 900 µL / mL do not exhibit mycelial growth.
    The combinations of chitosan + propolis + silver products have proven effective for the control of Bipolaris orizae fungi in rice seeds. The
    10 antifungal action on the percentage of healthy seeds, a measure of the efficiency of fungal control for different chitosan / propolis / silver combinations.
    Figure 4 shows that the most active combinations are those of chitosan / propolis / silver (C1, C2), those of chitosan oligomers (A50) and combinations of chitosan / silver (D1, D2), with percentages of maximum inhibition Follow
    15 in effectiveness to these treatments the propolis / silver combinations (F1, F2) that give rise to percentages of healthy seeds above 65% and, with smaller percentages, the chitosan / propolis and propolis mixtures only.
    The phytotoxicity of the different combinations against the control has been evaluated through the results of germination tests (EG) and measurement of stem length and
    20 root (LT), listed in Table 2.
    From the examination of these results it is concluded that, for the germination of rice seeds, the chitosan-silver combination (D2) is the treatment that offers a higher germination rate (90%). For the rest of the treatments it can be established that its antifungal properties are not accompanied by stimulating properties of the
    25 germination or growth of the seedling (root and aerial part).
    Table 2. Germination tests, stem and root diameters in seeds treated with different combinations of chitosan / propolis / silver (CHIPP): A50, B100, C1, C2, D1, D2, F1, F2, P and control.
    Treatments Concentrations (µl)
    TG (%) DT (cm)DR (cm)
    A50B100C1C2D1D2F1F2P Witness  85 65 85 85 82 91 60 80 90 853.36 2.81 2.87 2.71 3.76 3.92 2.86 2.74 4.18 4.148.33 8.75 10.15 9.57 8.89 9.23 9.87 9.31 10.54 10.45 5 Case 3. Bactericidal and fungicidal activity of binary and ternary mixtures of chitosan / propolis / silver on bacterial strains and fungi of hospital interest. Bactericidal activity
    As shown in Figure 5, for concentrations of 50 μg / mL, the samples of
    propolisAg or propolis-chitosan-nAg (samples 2 and 3) hardly inhibit bacterial growth (Staphylococcus aureus) or are resistant (Escherichia coli). But nevertheless,
    for concentrations around 300 μg / mL, chitosan and its combinations with propolis and
    Propolis-nAg are always sensitive, a fact that does not always happen for preparations
    of propolis-nAg. The inhibition of the Staphylococcus aureus strain tested has a high
    clinical interest given its character of methicillin resistance (MRSA). It should be noted that the 15 silver nanoparticles alone (nAg) do not show bactericidal activity per se (perhaps being
    retained in the upper layers of cellulose discs)
    In Figure 6 it can be seen that for concentrations above 300 μg / mL, all
    the preparations studied inhibit the growth of clinical strains of Acinetobacter
    baumanii and Pseudomonas aeruginosa. A comparative study of the inhibition halos and their concentrations allows us to notice that a ternary mixture of chitosan oligomers
    300 ug / ml propolis-nanoplate equals the activity produced by chitosan only at one
    concentration of 500 ug / ml or in other words: 100 ug / ml of chitosan in combination
    with the same amounts of propolis and nanoplate equals the activity they produce
    500 ug / ml chitosan alone. It can therefore be concluded indirectly that the ternary mixture 25 multiplies x5 the activity of chitosan alone.
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    权利要求:
    Claims (1)
    [1]
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    同族专利:
    公开号 | 公开日
    WO2016066876A1|2016-05-06|
    ES2568698B1|2017-02-08|
    引用文献:
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