CN103665074A - Extraction and purification method for natamycin in fermentation broth - Google Patents
Extraction and purification method for natamycin in fermentation broth Download PDFInfo
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- 229960003255 natamycin Drugs 0.000 title claims abstract description 71
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims abstract description 39
- 239000004311 natamycin Substances 0.000 title claims abstract description 17
- 235000010298 natamycin Nutrition 0.000 title claims abstract description 17
- 238000000855 fermentation Methods 0.000 title claims abstract description 15
- 230000004151 fermentation Effects 0.000 title claims abstract description 15
- 238000000605 extraction Methods 0.000 title claims abstract description 11
- 238000000746 purification Methods 0.000 title abstract 3
- 239000007788 liquid Substances 0.000 claims abstract description 36
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 23
- 238000001914 filtration Methods 0.000 claims abstract description 14
- 230000010355 oscillation Effects 0.000 claims abstract description 11
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 10
- 239000006228 supernatant Substances 0.000 claims abstract description 8
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 230000008025 crystallization Effects 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 4
- 230000008014 freezing Effects 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 abstract description 15
- 239000000284 extract Substances 0.000 abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 6
- 238000005406 washing Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 3
- 238000004108 freeze drying Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000005119 centrifugation Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241001655322 Streptomycetales Species 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000007613 environmental effect Effects 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- NCXMLFZGDNKEPB-UHFFFAOYSA-N Pimaricin Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCC(C)OC(=O)C=CC2OC2CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 NCXMLFZGDNKEPB-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- -1 dimethylbenzene acid amides Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000005452 food preservative Substances 0.000 description 2
- 235000019249 food preservative Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000001728 nano-filtration Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241001478240 Coccus Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000970906 Streptomyces natalensis Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
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Abstract
The invention discloses an extraction and purification method for natamycin in fermentation broth, and relates to natamycin. The extraction and purification method for the natamycin in the fermentation broth is high in yield and purity, low in cost, environment-friendly and suitable for industrial production, a process is convenient, the use of an organic solvent is avoided, and requirements on characteristics of the fermentation broth and equipment are low. The method comprises the following steps of a, adjusting the pH value of natamycin fermentation broth to 5.0 to 6.5, filtering the natamycin fermentation broth to remove moisture, and collecting solids; b, washing the solids collected in the step a, and centrifugally collecting the solids after standing; c, adding a sodium carbonate solution into the solids collected in the step b to obtain extract liquor, performing ultrasonic oscillation treatment, performing solid-liquid separation on the extract liquor, and collecting supernatant; d, adjusting the pH value of the supernatant obtained in the step c to 5.0 to 6.0 by using hydrochloric acid, performing filtration after standing and crystallization, and collecting, washing and freeze-drying the solids to obtain natamycin finished products.
Description
Technical field
The present invention relates to tennecetin, especially relate to the extracting and purifying method of tennecetin in a kind of fermented liquid.
Background technology
Tennecetin (Natamycin) claims again pimaricin (Pimaricin) or tennecetin (Tenecetin), and molecular formula is C
33h
47nO
13, molecular weight is 665.75 dalton, its appearance white or cream color are colourless crystallization powder, contain crystal water more than three molecules.Tennecetin is a kind of amphiprotic substance, has a basic group and an acidic-group in molecule, and iso-electric point is pH6.5, and fusing point is 280 ℃.Tennecetin is slightly soluble in water, methyl alcohol, is dissolved in diluted acid, Glacial acetic acid and dimethylbenzene acid amides, is insoluble in majority of organic solvent, has two kinds of typical configurations: enol-type structure and ketone form structure in its structure.At ambient temperature, the solubleness of tennecetin in water is 30～100mg/L, at water with in compared with lower alcohols, under neutral pH, solubleness is minimum, and along with rising and the reduction of pH value, the solvability of tennecetin increases, and at pH lower than 3 or higher than 9 o'clock, solubleness enlarges markedly.
Tennecetin is a kind of polyene macrolide antibiotics of efficient, wide spectrum, can suppress in specific manner nearly all yeast and mold, and some protozoon and some algae.As far back as June nineteen eighty-two, U.S. FDA can be used as food preservatives with regard to official approval tennecetin.From Food Additives Used in China technical committee for standardization (TCST) official approval tennecetin in 1996 can be used as food preservatives, China foodstuff additive council has just carried out tracking and the evaluation of application aspect to tennecetin, within 2011, formally put into effect < < foodstuff additive and used hygienic standard > >, using it as antimildew agent for food, for the course of processing of the food such as cheese, cake, meat soup, its trade name is Natamycin (NatamaxinTM).
Tennecetin is also having good application as anti-fungal infection medicine aspect medical science.Recently tennecetin is medically particularly emerging in an endless stream in the research aspect cornea fungi infestation and report, and the infection that it reads coccus to oral cavity has the result for the treatment of of highly significant.In addition, be also applied to the treatment that lung and Vaginal Fungi infect.
Tennecetin is standby by streptomycete fermentation legal system, and conventional streptomycete comprises Natal streptomycete (Streptomyces natalensis), brown yellow streptomycete (Streptomyces chattanoganis).Tennecetin is water insoluble under usual conditions, and more conventional organic solvents extract, as patent US3, and 892,850, WO92/07998, WO92/1058, CN10130729A, CN1891709A all take the method for organic solvent extraction.These methods need to be used inflammable, the volatile organic solvents such as methyl alcohol, Virahol, certainly will cause that higher solvent loss, recovery cost and higher safety features require, high expenses of environmental protection.Meanwhile, the use of methyl alcohol, easily causes the generation of this by product of tennecetin methyl esters, thereby affects the purity of product.
Patent WO97/29207 announces a kind of method that does not need organic solvent to extract tennecetin.The method is first used the method for physics or chemistry to make mycelial cell fragmentation, degraded in fermented liquid, tennecetin solid particulate in fermented liquid is suspended in water, then by applying neutral gradient centrifugation technology, makes tennecetin solid obtain product separated with cell debris.The method has advantages of that processing line is short out, but this technique is to the content requirement of tennecetin in fermented liquid higher (being greater than 7g/L), simultaneously to the tennecetin crystallographic dimension in fermented liquid and all once there had been strict requirement.In addition, from microbiotic, extract purifying specialty angle, utilize gravity gradient centrifugation technique to come the particle of thorough different grain size size to propose high requirement to separating device, also need the equipment maintenance cost of great number simultaneously.From above 2 application that can find out this extracting method, there is certain limitation.
Patent CN101062934A discloses a kind of method of with an organic solvent not extracting tennecetin from fermented liquid, and the method is to utilize the character of tennecetin different solubility in the aqueous solution under condition of different pH, realizes the extraction of tennecetin.In its alkalization process, the pH value of fermented liquid all requires more than 11, certainly will regulate with a large amount of alkali lye so originally aobvious acid fermented liquid.Although the method has been avoided organic solvent use, the use of a large amount of soda acids can bring consumption, the recovery problem of unpredictable environmental issue and soda acid equally.In addition, because the content of tennecetin in fermented liquid is lower, these methods all need to carry out the concentration of fermented liquid before extracting, and to improve, extract yield and purity, certainly will increase the energy consumption in production like this.
Patent CN102863492A announces a kind of method of with an organic solvent not extracting tennecetin from fermented liquid, the method is that to utilize oxalic acid to regulate fermented liquid pH be 2.8-3.0, add yellow prussiate of potash and zinc sulfate, add again sodium polyacrylate, after Chamber Type Diaphragm Filter Press filtration, Ultrafiltration Purifying, after nanofiltration purifying, crystallization, vacuum-drying, make tennecetin.Although the method has been avoided the use of organic solvent, its separating technology is had relatively high expectations to equipment and mould material, and processing step is many, also will concentrate to improve yield and purity in the end nanofiltration desalination, certainly will increase the cost in production like this.
Summary of the invention
The object of this invention is to provide simple process, yield is high, purity is high, do not use organic solvent, cost is low, environmental protection, low to the characteristic requirements of fermented liquid and equipment, and is applicable to the extracting and purifying method of tennecetin in a kind of fermented liquid that industrialization produces.
The present invention includes following steps:
A. regulate pH value to 5.0～6.5 of natamycin fermentation liquor, filter, remove moisture content, collect solid;
B. the solid of step a being collected cleans, standing after, centrifugal collection solid;
C. in the solid of collecting at step b, add sodium carbonate solution, obtain extraction liquid, then sonic oscillation processing, then extraction liquid is carried out to solid-liquid separation, collect supernatant liquor;
D. supernatant liquor step c being obtained is with salt acid for adjusting pH value to 5.0～6.0, standing, and crystallization and filtration is collected solid, cleans, freezing, after being dried, obtains tennecetin sterling.
In step a, described filtration can adopt centrifugal or Plate Filtration.
In step b, described cleaning can adopt by the clean water of 2 times of volumes of solid of collecting and clean; The described standing time can be 3～6h.
In step c, described in 5～50 times of the solid that adds the amount of sodium carbonate solution to can be by volume to collect, the volumetric molar concentration of described sodium carbonate solution can be 0.1～0.15mol/L; The condition that described sonic oscillation is processed can be under the temperature condition of 10～30 ℃, and sonic oscillation is processed 0.5～1h.
In steps d, described standing condition can be standing under the temperature condition of 5～25 ℃, and the time of described crystallization can be 10～15h; Described filtration can adopt centrifugal or Plate Filtration; The clean water of 1 times of volume of the available solid of described cleaning cleans 2 times.
The present invention be take sodium carbonate buffer salt solution and from fermented liquid, is extracted tennecetin and without regulating pH, be feature in extraction link as non-organic solvent; having solved organic solvent method extracts the tennecetin that tennecetin causes and extracts organic solvent solvent waste production cost high, that operation length causes higher problem in purifying engineering; also avoided regulating the link of extraction pH of mixed simultaneously; simplified extraction process; saved the consumption of soda acid; protected the stability of tennecetin; economy, environmental protection, technique are simple, and are applicable to industrialization and produce.The present invention has simple process, yield is high, purity is high (>=95%), do not use organic solvent, cost is low, environmental protection, to advantages such as the characteristic requirements of fermented liquid and equipment are low.
Accompanying drawing explanation
Fig. 1 is tennecetin standard substance HPLC figure.
Fig. 2 is tennecetin sterling HPLC figure.
Embodiment
Embodiment 1
Get 20L natamycin fermentation liquor, described natamycin fermentation liquor is the natamycin fermentation liquor that brown yellow spore streptomycete is got after cultivation, fermentating metabolism, tennecetin content is 10.31g/L, using hydrochloric acid to regulate fermented liquid pH is 6.0, uses Plate Filtration, obtains 2.72kg filter cake, use 3L clean water to clean one time filter cake, standing 5h, then centrifugation, obtain precipitation.To precipitation, adding volume is the sodium carbonate solution of the 0.15mol/L of 30L.Under the temperature condition of 20 ℃, sonic oscillation 0.5h, reaches after duration of oscillation, centrifugation, collects supernatant liquor, and regulating pH is 5.5, at the temperature of 25 ℃, standing 10h, centrifugal must precipitation, is used clean water washing and precipitating 2 times, centrifugation must precipitate again, lyophilize obtains tennecetin sterling 142.72g, and yield is 69%, and purity is greater than 95%.
Get 1.5L natamycin fermentation liquor, described natamycin fermentation liquor is the natamycin fermentation liquor that brown yellow spore streptomycete is got after cultivation, fermentating metabolism, tennecetin content is 6.34g/L, using hydrochloric acid to regulate fermented liquid pH is 5.5, uses centrifugation, obtains 192g precipitation, to precipitate and use 0.2L clean water to clean one time, standing 6h, then centrifugation, obtain precipitation.To precipitation, adding volume is the sodium carbonate solution of the 0.1mol/L of 2L.Under the temperature condition of 15 ℃, sonic oscillation 1h.Reach after duration of oscillation, centrifugation, collects supernatant liquor, regulating pH is 6.0, at the temperature of 15 ℃, standing 15h, reaches after time of repose, centrifugation must precipitate, use clean water washing and precipitating 2 times, in centrifugation, must precipitate, lyophilize obtains tennecetin sterling 6.18g, yield is 65%, and purity is greater than 95%.
Claims (10)
1. an extracting and purifying method for tennecetin in fermented liquid, is characterized in that comprising the following steps:
A. regulate pH value to 5.0～6.5 of natamycin fermentation liquor, filter, remove moisture content, collect solid;
B. the solid of step a being collected cleans, standing after, centrifugal collection solid;
C. in the solid of collecting at step b, add sodium carbonate solution, obtain extraction liquid, then sonic oscillation processing, then extraction liquid is carried out to solid-liquid separation, collect supernatant liquor;
D. supernatant liquor step c being obtained is with salt acid for adjusting pH value to 5.0～6.0, standing, and crystallization and filtration is collected solid, cleans, freezing, after being dried, obtains tennecetin sterling.
2. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in step a, and described filtration adopts centrifugal or Plate Filtration.
3. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in step b, and described cleaning adopts by the clean water of 2 times of volumes of solid of collecting and cleans.
4. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in step b, and the described standing time is 3～6h.
5. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, it is characterized in that in step c, the described amount that adds sodium carbonate solution is 5～50 times of the solid collected by volume, and the volumetric molar concentration of described sodium carbonate solution can be 0.1～0.15mol/L.
6. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in step c, and the condition that described sonic oscillation is processed be under the temperature condition of 10～30 ℃, sonic oscillation processing 0.5～1h.
7. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in steps d, and described standing condition is standing under the temperature condition of 5～25 ℃.
8. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in steps d, and the time of described crystallization is 10～15h.
9. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in steps d, and described filtration adopts centrifugal or Plate Filtration.
10. the extracting and purifying method of tennecetin in a kind of fermented liquid as claimed in claim 1, is characterized in that in steps d, and described cleaning is to clean 2 times with the clean water of 1 times of volume of solid.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108659075A (en) * | 2018-06-19 | 2018-10-16 | 苏州汉德瑞生物工程有限公司 | A kind of preparation method of novel polymolecularity Natamycin |
| CN110790801A (en) * | 2019-11-19 | 2020-02-14 | 浙江新银象生物工程有限公司 | Preparation method of high-purity white natamycin |
| CN112535645A (en) * | 2020-12-01 | 2021-03-23 | 成都医学院 | Application of natamycin in preparing shampoo and hair care product for removing dandruff and relieving itching |
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| CN108659075A (en) * | 2018-06-19 | 2018-10-16 | 苏州汉德瑞生物工程有限公司 | A kind of preparation method of novel polymolecularity Natamycin |
| CN110790801A (en) * | 2019-11-19 | 2020-02-14 | 浙江新银象生物工程有限公司 | Preparation method of high-purity white natamycin |
| CN110790801B (en) * | 2019-11-19 | 2021-05-04 | 浙江新银象生物工程有限公司 | Preparation method of high-purity white natamycin |
| CN112535645A (en) * | 2020-12-01 | 2021-03-23 | 成都医学院 | Application of natamycin in preparing shampoo and hair care product for removing dandruff and relieving itching |
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