CN101491240A - Method for increasing natamycin action efficiency - Google Patents
Method for increasing natamycin action efficiency Download PDFInfo
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- CN101491240A CN101491240A CNA2008100521605A CN200810052160A CN101491240A CN 101491240 A CN101491240 A CN 101491240A CN A2008100521605 A CNA2008100521605 A CN A2008100521605A CN 200810052160 A CN200810052160 A CN 200810052160A CN 101491240 A CN101491240 A CN 101491240A
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- natamycin
- cyclodextrin
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Abstract
The invention relates to a method for improving the natamycin action efficiency. The method comprises the following steps: taking cyclodextrin and derivatives as the supermolecule host compounds to prepare a natamycin/cyclodextrin supermolecule clathrate; and keeping the bacteriostatic activity of natamycin and improving the water solubility and stability of natamycin. The preparation method for the natamycin/cyclodextrin supermolecule clathrate comprises the following steps: preparing an aqueous solution of the cyclodextrin and the derivatives through ultra pure water to reach certain solubility; adding a certain amount of natamycin into the aqueous solution of the cyclodextrin and the derivatives, and carrying out ultrasonic treatment for 5 minutes to improve the complexation efficiency; and covering a layer of aluminum-foil paper on the container of the suspension, placing the container on a shaking table at a room temperature for reaction, and obtaining the homogenous solution of the natamycin/cyclodextrin supermolecule clathrate after reaching the balance. The method has the advantages of improving the solubility and stability of natamycin in the aqueous solution, improving the natamycin bioavailability, solving the problem of poor water solubility of natamycin, and improving the action efficiency of the biological bacteriocide natamycin.
Description
Technical field
The present invention relates to the method for antibiotic as the anti-corrosive fresh-keeping of natural biological antiseptic agent, particularly a kind of method that improves natamycin action efficiency increases solvability and the stability of natamycin in the aqueous solution.
Background technology
Natamycin is a kind of antimycotic polyene macrolide antibiotics of wide spectrum, and natamycin is extremely people's concern with its safe, natural, healthy characteristic.It has following characteristics as the natural biological antiseptic antistaling agent: low dosage, high efficiency, do not influence flavours in food products, compare with other antibacterial agents, the toxicity of natamycin is extremely low, no carcinogenic, teratogenesis, mutagenesis.Natamycin has gone through to be applied in the numerous food product industry such as dairy products, meat, fruit, beverage, and most suspension that adopt soak or spray.
The antibiotic mechanism of natamycin be it can with the reaction of sterol compound on cell wall and the cell membrane, especially ergosterol forms a kind of compound, the trigger cell membrane structure changes thus, causes the seepage of cellular content to make cell death.In use, the dissolving of natamycin part must be diffused into action site and and target fungi combination.When having only the water-soluble solution of natamycin, it is maximum that its bioavilability just reaches.Very low (30～50mg/L), the dissolubility in many organic solvents is also relatively poor, and the stability of natamycin is subject to the influence of extreme pH environment, temperature, intensity of illumination and oxidant and heavy metal but natamycin is water-soluble.Natamycin low-solubility and lability become the restricted factor of its bioavilability.Natamycin has better water solubility under strong acid or highly basic condition, but its easy degraded.When the pH of environment hanged down very much, the glycosidic bond hydrolysis produced mycosamine.Under high pH condition, the quick saponification of lactone forms the not bioactive natamycin acid of tool.Research increases the water miscible method of natamycin and just seems particularly important.In recent years, by introduce can solubilising chemical functional group carry out chemical modification, natamycin after the modification such as natamycin cholate, N-(the amino succinimide of 3-N-dimethyl propylene) natamycin etc., although solvability increases, but, demonstrate lower biologically active owing to changed the part-structure of natamycin.The SS-natamycin is a kind of Water Soluble Compound body by the modification of polysaccharides be combined into of 66% natamycin and 34%, but its biologically active is low and toxicity strengthens.Perhaps this original structure of natamycin is best, and any chemical modification all can reduce its activity.
Therefore improve the functioning efficiency of natamycin, increasing the solvability of biological bactericide natamycin in the aqueous solution and stability is to improve the best approach of its biological utilisation, and this has solved the difficult problem of natamycin poorly water-soluble on commerce is used to a certain extent.
Summary of the invention
The purpose of this invention is to provide the method that improves natamycin action efficiency, solve the difficult problem of natamycin poorly water-soluble on commerce is used, proposed a kind of biological bactericide natamycin solvability and stable method in the aqueous solution of increasing.
The present invention is by the following technical solutions:
Adopt cyclodextrin and derivative thereof as the supermolecule main block compound, prepare natamycin/cyclodextrin super molecule inclusion compound.It has kept the bacteriostatic activity of natamycin, and the water-soluble and stability of natamycin is increased greatly.
The preparation method of natamycin/cyclodextrin super molecule inclusion compound is as follows:
A. with the aqueous solution of ultra-pure water preparation cyclodextrin and derivative thereof, reach the solvability that needs.
B. add the different natamycins of measuring in the aqueous solution of cyclodextrin and derivative thereof according to desired concn, ultrasonic 5min is to increase Complexation Efficiency.
C. with above-mentioned suspension at container outsourcing layer of aluminum foil paper, at room temperature place on the shaking table and react, shaking table revolution 200rpm can obtain the uniform solution of natamycin/cyclodextrin super molecule inclusion compound after reaching balance in 12～48 hours.
Cyclodextrin in a step and derivative thereof are beta-schardinger dextrin-, gamma-cyclodextrin, HP-, DM-, sulfobutyl ether-beta-cyclodextrin, G 2-CD etc., and wherein beta-schardinger dextrin-, gamma-cyclodextrin, HP-are preferred.
The solvability of natamycin is relevant with the kind of cyclodextrin and derivative thereof in the b step, and becomes positive correlation with the concentration of cyclodextrin and derivative thereof, and the maxima solubility of natamycin can reach 2～5g/L.
In the c step on shaking table 20～28 hours balanced reaction time be preferred.
Advantage of the present invention:
Adopt cyclodextrin and derivative thereof as the supermolecule main block compound, prepare natamycin/cyclodextrin super molecule inclusion compound.It has kept the bacteriostatic activity of natamycin, and the water-soluble and stability of natamycin is increased greatly.Adopt the method can improve the functioning efficiency of natamycin, increase the solvability of biological bactericide natamycin in the aqueous solution and its bioavilability of stability raising, this has solved the difficult problem of natamycin poorly water-soluble on commerce is used to a certain extent.
Embodiment:
Example one: with ultra-pure water preparation gamma-cyclodextrin solution 500mL, make its concentration reach 70mM, the 1.7g natamycin joins in the gamma-cyclodextrin aqueous solution, ultrasonic 5min.Above-mentioned suspension at container outsourcing layer of aluminum foil paper, is at room temperature placed on the shaking table and reacts, and shaking table revolution 200rpm reached balance in 24 hours, can obtain the uniform solution of natamycin/gamma-cyclodextrin super molecule inclusion compound.Get a certain amount of this solution 0.45 μ m ultrafiltration membrance filter, high-performance liquid chromatogram determination, the concentration of whole solution is 3.3g/L.
Example two: with ultra-pure water preparation beta-schardinger dextrin-solution 500mL, make its concentration reach 16mM, the 1.1g natamycin joins in the beta-schardinger dextrin-aqueous solution, ultrasonic 5min.Above-mentioned suspension at container outsourcing layer of aluminum foil paper, is at room temperature placed on the shaking table and reacts, and shaking table revolution 200rpm reached balance in 28 hours, can obtain the uniform solution of natamycin/beta-schardinger dextrin-super molecule inclusion compound.Get a certain amount of this solution 0.45 μ m ultrafiltration membrance filter, high-performance liquid chromatogram determination, the concentration of whole solution is 2.0g/L.
Example three: with ultra-pure water preparation HP-solution 500mL, make its concentration reach 70mM, the 2.5g natamycin joins in the HP-aqueous solution, ultrasonic 5min.Above-mentioned suspension at container outsourcing layer of aluminum foil paper, is at room temperature placed on the shaking table and reacts, and shaking table revolution 200rpm reached balance in 24 hours, can obtain the uniform solution of natamycin/HP-super molecule inclusion compound.Get a certain amount of this solution 0.45 μ m ultrafiltration membrance filter, high-performance liquid chromatogram determination, the concentration of whole solution is 4.8g/L.
Example four: with ultra-pure water preparation G 2-CD solution 500mL, make its concentration reach 70mM, the 1.25g natamycin joins in the G 2-CD aqueous solution, ultrasonic 5min.Above-mentioned suspension at container outsourcing layer of aluminum foil paper, is at room temperature placed on the shaking table and reacts, and shaking table revolution 200rpm reached balance in 16 hours, can obtain the uniform solution of natamycin/gamma-cyclodextrin super molecule inclusion compound.Get a certain amount of this solution 0.45 μ m ultrafiltration membrance filter, high-performance liquid chromatogram determination, the concentration of whole solution is 2.4g/L.
Cyclodextrin in the above step and derivative gamma-cyclodextrin thereof, also available: beta-schardinger dextrin-,, HP-, DM-, sulfobutyl ether-beta-cyclodextrin, G 2-CD, wherein beta-schardinger dextrin-, gamma-cyclodextrin, HP-are preferred;
The solvability of natamycin is relevant with the kind of cyclodextrin and derivative thereof in the step, and becomes positive correlation with the concentration of cyclodextrin and derivative thereof, and the maxima solubility of natamycin can reach 2～5g/L.
In the step on shaking table the balanced reaction time be 12～48 hours, generally use between 20～28 hours.
Claims (3)
1, a kind of method that improves natamycin action efficiency:
Adopt cyclodextrin and derivative thereof as the supermolecule main block compound, prepare natamycin/cyclodextrin super molecule inclusion compound; It has kept the bacteriostatic activity of natamycin, and the water-soluble and stability of natamycin is increased greatly;
The preparation method of natamycin/cyclodextrin super molecule inclusion compound is as follows:
A. with the aqueous solution of ultra-pure water preparation cyclodextrin and derivative thereof, reach the solvability that needs;
B. add the different natamycins of measuring in the aqueous solution of cyclodextrin and derivative thereof according to desired concn, ultrasonic 5min is to increase Complexation Efficiency;
C. with above-mentioned suspension at container outsourcing layer of aluminum foil paper, at room temperature place on the shaking table and react, shaking table revolution 200rpm can obtain the uniform solution of natamycin/cyclodextrin super molecule inclusion compound after reaching balance in 12～48 hours;
Cyclodextrin in a step and derivative thereof are beta-schardinger dextrin-, gamma-cyclodextrin, HP-, DM-, sulfobutyl ether-beta-cyclodextrin, G 2-CD, and wherein beta-schardinger dextrin-, gamma-cyclodextrin, HP-are preferred;
The solvability of natamycin is relevant with the kind of cyclodextrin and derivative thereof in the b step, and becomes positive correlation with the concentration of cyclodextrin and derivative thereof, and the maxima solubility of natamycin can reach 2～5g/L.
2, want the method for 1 described raising natamycin action efficiency according to right: cyclodextrin in a step and derivative thereof are beta-schardinger dextrin-, gamma-cyclodextrin, HP-..
3, want the method for 1 described raising natamycin action efficiency according to right: in the c step on shaking table 20～28 hours balanced reaction time.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100521605A CN101491240A (en) | 2008-01-25 | 2008-01-25 | Method for increasing natamycin action efficiency |
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| CNA2008100521605A CN101491240A (en) | 2008-01-25 | 2008-01-25 | Method for increasing natamycin action efficiency |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102326619A (en) * | 2011-10-19 | 2012-01-25 | 陕西省微生物研究所 | Vegetable and fruit coating preservative and preparation method thereof |
| WO2012101256A1 (en) | 2011-01-28 | 2012-08-02 | Danisco A/S | Natamycin-cyclodextrin complexes for use in foodstuff, process for their manufacture and use thereof |
| CN102742581A (en) * | 2012-07-20 | 2012-10-24 | 陕西省微生物研究所 | Preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex |
| CN104188049A (en) * | 2014-07-18 | 2014-12-10 | 洛阳奇泓生物科技有限公司 | Preparation method of stable natamycin suspension liquid, and application thereof |
| CN106983674A (en) * | 2016-11-24 | 2017-07-28 | 北京桑普生物化学技术有限公司 | A kind of water-soluble myprozine composition and preparation method and application |
| CN107280992A (en) * | 2017-06-26 | 2017-10-24 | 北京桑普生物化学技术有限公司 | Waterborne-type preservation composition containing natamycin and preparation method and application |
| CN104968219B (en) * | 2013-01-31 | 2018-03-02 | 百事可乐公司 | Beverage preservation system based on pimaricin and headspace gas |
| CN107858387A (en) * | 2017-12-12 | 2018-03-30 | 山东福瑞达生物科技有限公司 | A kind of preparation method of high-dissolvability natamycin |
| CN108813609A (en) * | 2018-06-22 | 2018-11-16 | 广东药科大学 | A kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound |
| CN110312511A (en) * | 2017-02-15 | 2019-10-08 | 大鹏药品工业株式会社 | Medical composition |
| CN112167334A (en) * | 2020-09-10 | 2021-01-05 | 长沙沃霖农副产品开发有限公司 | Preparation method of frozen fresh walnuts |
-
2008
- 2008-01-25 CN CNA2008100521605A patent/CN101491240A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012101256A1 (en) | 2011-01-28 | 2012-08-02 | Danisco A/S | Natamycin-cyclodextrin complexes for use in foodstuff, process for their manufacture and use thereof |
| CN103491807A (en) * | 2011-01-28 | 2014-01-01 | 杜邦营养生物科学有限公司 | Natamycin-cyclodextrin complexes for use in foodstuff, process for their manufacture and use thereof |
| AU2012210484B2 (en) * | 2011-01-28 | 2015-05-28 | Dupont Nutrition Biosciences Aps | Natamycin-cyclodextrin complexes for use in foodstuff, process for their manufacture and use thereof |
| CN102326619A (en) * | 2011-10-19 | 2012-01-25 | 陕西省微生物研究所 | Vegetable and fruit coating preservative and preparation method thereof |
| CN102742581A (en) * | 2012-07-20 | 2012-10-24 | 陕西省微生物研究所 | Preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex |
| CN104968219B (en) * | 2013-01-31 | 2018-03-02 | 百事可乐公司 | Beverage preservation system based on pimaricin and headspace gas |
| CN104188049A (en) * | 2014-07-18 | 2014-12-10 | 洛阳奇泓生物科技有限公司 | Preparation method of stable natamycin suspension liquid, and application thereof |
| CN106983674A (en) * | 2016-11-24 | 2017-07-28 | 北京桑普生物化学技术有限公司 | A kind of water-soluble myprozine composition and preparation method and application |
| CN106983674B (en) * | 2016-11-24 | 2022-02-18 | 北京桑普生物化学技术有限公司 | Water-soluble natamycin composition and preparation method and application thereof |
| CN110312511A (en) * | 2017-02-15 | 2019-10-08 | 大鹏药品工业株式会社 | Medical composition |
| CN110312511B (en) * | 2017-02-15 | 2023-10-27 | 大鹏药品工业株式会社 | Pharmaceutical composition |
| CN107280992A (en) * | 2017-06-26 | 2017-10-24 | 北京桑普生物化学技术有限公司 | Waterborne-type preservation composition containing natamycin and preparation method and application |
| CN107858387A (en) * | 2017-12-12 | 2018-03-30 | 山东福瑞达生物科技有限公司 | A kind of preparation method of high-dissolvability natamycin |
| CN108813609A (en) * | 2018-06-22 | 2018-11-16 | 广东药科大学 | A kind of preparation method of grape seed extract sulfobutyl ether-beta-cyclodextrin inclusion compound |
| CN112167334A (en) * | 2020-09-10 | 2021-01-05 | 长沙沃霖农副产品开发有限公司 | Preparation method of frozen fresh walnuts |
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