CN102742581A - Preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex - Google Patents
Preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex Download PDFInfo
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- CN102742581A CN102742581A CN2012102525999A CN201210252599A CN102742581A CN 102742581 A CN102742581 A CN 102742581A CN 2012102525999 A CN2012102525999 A CN 2012102525999A CN 201210252599 A CN201210252599 A CN 201210252599A CN 102742581 A CN102742581 A CN 102742581A
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Abstract
The invention relates to a preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex. Natamycin exists in an enol structure and a keto structure typically, has low solubility to many solvents, and accordingly has popularization limitations. The preparation method includes: dissolving the natamycin in alkali; adding hydroxypropyl-beta-cyclodextrin, allowing inclusion of the hydroxypropyl-beta-cyclodextrin with the natamycin at the temperature of 15 DEG C to 40 DEG C; adding acid solution in an inclusion system for neutralizing after inclusion, and drying to obtain power of the natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex, wherein mole ratio of the natamycin to the hydroxypropyl-beta-cyclodextrin is 1:4.5-6. The preparation method using no organic solvent is simple in process, short in cycle and low in cost. The natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex prepared by the preparation method is powder, the powder has solubility improved by more than 1000 times and high stability, bioavailability of the natamycin-hydroxypropyl-beta-cyclodextrin inclusion complex is more effective, and the natamycin can be given to fuller play in the antifungal use in the fields of food, agriculture, medicine and the like.
Description
Technical field
The present invention relates to a kind of preparation method of bacteriostatic agent, be specifically related to a kind of preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion.
Background technology
Natamycin is mainly produced by Natal streptomycete (Streptomyces natalensis), also claims trip streptomycin (Pimaricin), is that a kind of polyene macrolide is antifungal agents based, and mould, saccharomycete are had extremely strong inhibitory action.Its antibiotic mechanism 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.Research shows that most moulds are suppressed under the natamycin concentration of 0.5-6ppm, extremely other kind is suppressed under the natamycin concentration of 10-25ppm; Most yeast are suppressed under the natamycin concentration of 1.0-5.0ppm.Therefore, natamycin is very responsive to fungi, and micro-use can be worked, and is merely the 1/50-1/100 of potassium sorbate as the consumption of preservative.Natamycin is used for food antiseptic not only can solve food spoilage; Can also reduce the murder by poisoning of mycotoxin to the mankind, compare with other antimicrobial components, natamycin is extremely low to the toxicity of mammalian cell; No carcinogenic, teratogenesis, mutagenesis can be widely used in fungus-caused disease.At present, natamycin by the approval of more than 50 countries and regions be applied to dairy products, meat, fruit, beverage, medicine and other can antimycotic field in.
Because have two kinds of typical configurations on the natamycin structure: enol-type structure and ketone form structure, this has just determined it in many solvents, to have the defective of low-solubility.The solvability of natamycin in water is 30-50mg/L under the room temperature.Be mainly used in as food preservative at present the surface of food is handled; Because having only, the natamycin of dissolving combines the competence exertion effect with object; The low aqueous solubility of natamycin is unfavorable for its bioavilability; This has had a strong impact on the result of use of natamycin, has also limited the scope of application of natamycin.Natamycin is to temperature simultaneously; Ultraviolet light, the factors such as oxidant and heavy metal are relatively more responsive, and be especially responsive to illumination; Its photostability is poor; The biocidal property of natamycin weakens rapidly along with the increase of UV-irradiation time, and (10W, 30cm) treatment with irradiation loses activity behind 60min ultraviolet basically.As as biopesticide because light is stable poor, its availability is greatly reduction just.Experiment confirms that also natamycin also can prolong in time and reduce the antiseptic effect of food.Though natamycin is active higher, its solvability in water is very low relatively poor with photostability, thereby has limited applying of its.
Summary of the invention
The purpose of this invention is to provide the preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion that a kind of mild condition, technology are simple, the inclusion productive rate is high, prepare the new bacteriostatic agent that biocidal property is strong, solvability is high.
The technical scheme that the present invention adopted is:
The preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion is characterized in that:
Realize by following steps:
Step 1: natamycin is dissolved in the aqueous slkali, and the pH value is 11.5-13;
Step 2: add HP-, under 15 ℃ of-40 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:4.5-6;
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis.
In the step 1, aqueous slkali is selected from sodium hydroxide solution, potassium hydroxide solution, aqua calcis, and molar concentration is 0.02-0.2mol/L.
In the step 3, acid solution is selected from hydrochloric acid solution, oxalic acid solution, acetum, and molar concentration is 0.5-1.5mol/L.
In the step 2, inclusion method is selected to organize at a high speed smashs method, magnetic agitation method, ultrasonic method, electronic paddling process to pieces.
In the step 3, the drying means of inclusion product is selected from hypobaric drying method, freeze-drying, spray drying process.
The present invention has the following advantages:
Preparation method of the present invention does not use any organic reagent, and technology is simple, and reaction time is short; Cost is low, can be mass-produced, and utilizes HP-and natamycin to prepare natamycin-hydroxypropyl-beta-cyclodextrin inclusion; The inclusion compound steady quality that generates helps improving the solvability of natamycin in water, and experiment shows; Natamycin-hydroxypropyl-beta-cyclodextrin inclusion the pulvis that utilizes preparation method of the present invention to obtain is solid powder, and is easy to use; Water-soluble maximum >=the 60g/L of natamycin (dissolving 30-50mg/L in the former natamycin water) wherein; Be equivalent to solvability and improve more than 1000 times, bioavailability is more effective, and natamycin antimycotic utilization in food, agricultural, medicine and other fields is played a greater role.
Description of drawings
Fig. 1 is natamycin differential scanning calorimetric analysis (DSC) collection of illustrative plates;
Fig. 2 is HP-differential scanning calorimetric analysis (DSC) collection of illustrative plates;
Fig. 3 is natamycin-HP-physical mixture differential scanning calorimetric analysis (DSC) collection of illustrative plates;
Fig. 4 is natamycin-hydroxypropyl-beta-cyclodextrin inclusion differential scanning calorimetric analysis (DSC) figure.
Embodiment
Below in conjunction with embodiment the present invention is carried out detailed explanation.
The present invention to the dissolubility change of natamycin, increases solvability and the stability of natamycin in the aqueous solution under the prerequisite of the molecular structure that does not influence natamycin, improve the bioavailability of natamycin.
Concrete preparation process is following:
Step 1: natamycin-HP-is dissolved in the aqueous slkali, and the pH value is 11.5-13; Aqueous slkali is selected from sodium hydroxide solution, potassium hydroxide solution, aqua calcis, and molar concentration is 0.02-0.2mol/L.
Step 2: add HP-, under 15 ℃ of-40 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:4.5-6;
Inclusion method is selected to organize at a high speed smashs method, magnetic agitation method, ultrasonic method, electronic paddling process to pieces.
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis; Acid solution is selected from hydrochloric acid solution, oxalic acid solution, acetum, and molar concentration is 0.5-1.5mol/L.
The drying means of inclusion product is selected from hypobaric drying method, freeze-drying, spray drying process.
Entire reaction period is 2-3 hour.
Embodiment one:
Step 1: natamycin is dissolved in the aqueous slkali, and system pH is 11.5; Aqueous slkali is a sodium hydroxide solution, and molar concentration is 0.02mol/L.
Step 2: add HP-, under 15 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:4.5.
Inclusion method is for organizing the method for smashing to pieces at a high speed.
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis; Acid solution is a hydrochloric acid solution, and molar concentration is 0.5mol/L.
The drying means of inclusion product is a hypobaric drying method.
Embodiment two:
Step 1: natamycin is dissolved in the aqueous slkali, and system pH is 11.5; Aqueous slkali is a sodium hydroxide solution, and molar concentration is 0.05mol/L.
Step 2: add hydroxy propyl-Beta-ring and stick with paste, under 25 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:5;
Inclusion method is for organizing the method for smashing to pieces at a high speed.
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis; Acid solution is a hydrochloric acid solution, and molar concentration is 0.5mol/L.
The drying means of inclusion product is a hypobaric drying method.
Embodiment three:
Step 1: natamycin is dissolved in the aqueous slkali, and system pH is 12; Aqueous slkali is a potassium hydroxide solution, and molar concentration is 0.1mol/L.
Step 2: add HP-, under 30 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:6.
Inclusion method is the magnetic agitation method.
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis; Acid solution is oxalic acid solution, acetum, and molar concentration is 1mol/L.
The drying means of inclusion product is a freeze-drying.
Embodiment four:
Step 1: natamycin is dissolved in the aqueous slkali, and system pH is 12.5; Aqueous slkali is a potassium hydroxide solution, and molar concentration is 0.15mol/L.
Step 2: add HP-, under 35 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:5.5.
Inclusion method is a ultrasonic method.
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis; Acid solution is a hydrochloric acid solution, and molar concentration is 1mol/L.
The drying means of inclusion product is a freeze-drying.
Embodiment five:
Step 1: natamycin is dissolved in the aqueous slkali, and system pH is 13; Aqueous slkali is an aqua calcis, and molar concentration is 0.2mol/L.
Step 2: add HP-, under 40 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:5.
Inclusion method is electronic paddling process.
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis; Acid solution is an oxalic acid solution, and molar concentration is 1.5mol/L, needs after the neutralization to filter, and calcium oxalate can produce deposition.
The drying means of inclusion product is a spray drying process.
The present invention utilizes HP-.Prepare natamycin-hydroxypropyl-beta-cyclodextrin inclusion with natamycin; The inclusion compound steady quality that generates; Help improving the solvability of natamycin in water; Experiment shows, natamycin one hydroxypropyl-beta-cyclodextrin inclusion of the present invention all has significant water-soluble and good stable property as water soluble preparation natamycin commodity preparation on simple natamycin or the market.
1, inclusion compound in-vitro antibacterial result of the test of the present invention:
Test adopts agar dilution to measure the minimum inhibitory concentration (MIC) of test specimen and control sample under the different bacterial concentrations.Through observing the dull and stereotyped growing state of going up test strain; Concentration with asepsis growth is MIC; Test shows that natamycin-hydroxypropyl-beta-cyclodextrin inclusion is suppressing fungi effect identical (seeing table 1) with the natamycin reference substance, and the antibiotic biologically active of natamycin-hydroxypropyl-beta-cyclodextrin inclusion is stable.
Table 1 minimum inhibitory concentration (MIC) (unit: mg/kg)
2, ultraviolet irradiation is to the result of the test that influences of natamycin aqueous stability:
Natamycin reference substance and natamycin-hydroxypropyl-beta-cyclodextrin inclusion handled respectively be mixed with the certain density aqueous solution; Be placed on ultraviolet lighting intensity 20W simultaneously; Apart from the 30cm place, measure 0,15,30,45,60,75 respectively, natamycin relative amount during 90min.
Result of the test shows that natamycin-hydroxypropyl-beta-cyclodextrin inclusion significantly improves (seeing table 2) than the natamycin reference substance to the stability of ultraviolet irradiation.
Table 2 ultraviolet irradiation is to the influence of natamycin aqueous solution relative amount
3, water-soluble natamycin maxima solubility is measured:
Purpose: the solvability (maxima solubility) of verifying water-soluble natamycin; Because the dissolubility of HP-in water is the highest can reach 80g/100ml, thus test adopt add 60g HP-/natamycin bag and preparation measure.
Adopt balancing method: excessive solute is added in the solvent, and the constant temperature jolting is measured concentration after filtering to balance.The HPLC method is measured content; With 60g content is that 10.36% highly-water-soluble natamycin adds entry and is settled to 100ml, is transferred to then in the 300ml triangular flask, at 25 ℃ constant-temperature shaking appearance; 150r/min carries out the balance dissolving; Simultaneously do contrast, whenever no longer increase, be equilibration time at a distance from 24 h sampling and measuring to concentration with the raw material natamycin of 100mg.The result shows highly-water-soluble natamycin maxima solubility >=60g/L.
The solvability of the water-soluble natamycin of table 3
4,
Inclusion compound differential scanning calorimetric analysis (DSC)
Purpose: the phase transition temperature (fusing point) through detecting inclusion compound changes, and whether the formation of judgement inclusion compound.
Test material:
Differential scanning calorimeter appearance (the anti-company of speeding of DTA 404 PC Germany)
Natamycin (Zhejiang Province's silver resembles biological 95%)
HP-(the Xi'an moral is found biological Co., Ltd 99%)
Natamycin/hydroxypropyl-beta-cyclodextrin inclusion (laboratory self-control 12.3%)
Natamycin/HP-mixture (laboratory self-control 1.2:9)
Method and result:
Respectively samples such as inclusion compound, physical mixture, natamycin and HP-are carried out differential thermal analysis, 10 ℃/min of heating rate, 30-400 ℃ of intensification scope.The result sees accompanying drawing.The collection of illustrative plates of inclusion compound medicine, physical mixture has evident difference, and natamycin fusing point place does not have obvious endothermic peak in Fig. 4, explain HP-basically inclusion natamycin.Fig. 3 is the stack of Fig. 1 and Fig. 2 basically.
It is cited that content of the present invention is not limited to embodiment, and the conversion of any equivalence that those of ordinary skills take technical scheme of the present invention through reading specification of the present invention is claim of the present invention and contains.
Claims (5)
1. the preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion is characterized in that:
Realize by following steps:
Step 1: natamycin is dissolved in the aqueous slkali, and the pH value is 11.5-13;
Step 2: add HP-, under 15 ℃ of-40 ℃ of temperature condition, carry out inclusion reaction with natamycin, the mol ratio of natamycin and HP-is 1:4.5-6;
Step 3: after reaction finishes, in reaction system, add acid solution and neutralize, after drying, obtain natamycin-hydroxypropyl-beta-cyclodextrin inclusion pulvis.
2. the preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion according to claim 1 is characterized in that:
In the step 1, aqueous slkali is selected from sodium hydroxide solution, potassium hydroxide solution, aqua calcis, and molar concentration is 0.02-0.2mol/L.
3. the preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion according to claim 1 and 2 is characterized in that:
In the step 3, acid solution is selected from hydrochloric acid solution, oxalic acid solution, acetum, and molar concentration is 0.5-1.5mol/L.
4. the preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion according to claim 3 is characterized in that:
In the step 2, inclusion method is selected to organize at a high speed smashs method, magnetic agitation method, ultrasonic method, electronic paddling process to pieces.
5. the preparation method of natamycin-hydroxypropyl-beta-cyclodextrin inclusion according to claim 4 is characterized in that:
In the step 3, the drying means of inclusion product is selected from hypobaric drying method, freeze-drying, spray drying process.
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| CN103125497A (en) * | 2012-12-07 | 2013-06-05 | 浙江工业大学 | Fenoxaprop-p-ethyl cyclodextrin inclusion compound and preparation method thereof |
| 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 |
| WO2018060321A1 (en) | 2016-09-28 | 2018-04-05 | Eucaryo Beheer B.V. | Composition comprising a bioactive molecule |
| CN111000112A (en) * | 2020-01-02 | 2020-04-14 | 中国农业科学院农产品加工研究所 | Natamycin composition and application thereof |
| CN111972423A (en) * | 2020-08-04 | 2020-11-24 | 黄山天目薄荷药业有限公司 | Bactericidal agent suitable for menthol and preparation method thereof |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103125497A (en) * | 2012-12-07 | 2013-06-05 | 浙江工业大学 | Fenoxaprop-p-ethyl cyclodextrin inclusion compound and preparation method thereof |
| WO2018060321A1 (en) | 2016-09-28 | 2018-04-05 | Eucaryo Beheer B.V. | Composition comprising a bioactive molecule |
| CN110461150A (en) * | 2016-09-28 | 2019-11-15 | 尤卡优管理公司 | Composition containing bioactive molecule |
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| US11839217B2 (en) * | 2016-09-28 | 2023-12-12 | Eucaryo Beheer B.V. | Composition comprising a bioactive molecule |
| 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 |
| CN111000112A (en) * | 2020-01-02 | 2020-04-14 | 中国农业科学院农产品加工研究所 | Natamycin composition and application thereof |
| CN111972423A (en) * | 2020-08-04 | 2020-11-24 | 黄山天目薄荷药业有限公司 | Bactericidal agent suitable for menthol and preparation method thereof |
| CN111972423B (en) * | 2020-08-04 | 2022-06-17 | 黄山天目薄荷药业有限公司 | Bactericidal agent suitable for menthol and preparation method thereof |
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