CN109970800A - A kind of bismuth-scutelloside complex and its preparation method and application - Google Patents
A kind of bismuth-scutelloside complex and its preparation method and application Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- XDQITMCFPPPMBC-TUANDBMESA-N scutelloside Natural products OC[C@H]1O[C@@H](O[C@@H]2O[C@@H]3C[C@H]4[C@H](O)[C@@H](O)[C@@](O)(CO3)[C@@H]24)[C@H](O)[C@@H](O)[C@@H]1O XDQITMCFPPPMBC-TUANDBMESA-N 0.000 claims abstract description 101
- 229910001451 bismuth ion Inorganic materials 0.000 claims abstract description 57
- 239000007788 liquid Substances 0.000 claims abstract description 44
- 239000002243 precursor Substances 0.000 claims abstract description 38
- 150000001621 bismuth Chemical class 0.000 claims abstract description 32
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Chinese gallotannin Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims abstract description 23
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 14
- 239000000243 solution Substances 0.000 claims description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 48
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 33
- 229910052797 bismuth Inorganic materials 0.000 claims description 31
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 229910002651 NO3 Inorganic materials 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000012153 distilled water Substances 0.000 claims description 9
- 239000013049 sediment Substances 0.000 claims description 7
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical group Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 3
- 239000000273 veterinary drug Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 30
- 230000001376 precipitating effect Effects 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 12
- 239000012530 fluid Substances 0.000 description 10
- 241000588724 Escherichia coli Species 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 229930182470 glycoside Natural products 0.000 description 8
- 150000002338 glycosides Chemical class 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- 241000282898 Sus scrofa Species 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- -1 flavone compound Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 235000014676 Phragmites communis Nutrition 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 231100001231 less toxic Toxicity 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 235000019621 digestibility Nutrition 0.000 description 2
- 230000000857 drug effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000305071 Enterobacterales Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- NNLOHLDVJGPUFR-UHFFFAOYSA-L calcium;3,4,5,6-tetrahydroxy-2-oxohexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(=O)C([O-])=O.OCC(O)C(O)C(O)C(=O)C([O-])=O NNLOHLDVJGPUFR-UHFFFAOYSA-L 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/005—Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention discloses a kind of bismuth-scutelloside complex and its preparation method and application, is related to veterinary drug technical field.The bismuth-scutelloside complex general molecular formula is (C21H17O11)(NO3)Bi·4H2O, the bismuth-scutelloside complex have structure shown in structural formula (1).The bismuth-scutelloside complex preparation method obtains bismuth ion precursor liquid the following steps are included: bismuth salt is dissolved in glycerite；The bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, bismuth-scutelloside complex is reacted to obtain.The present invention is directed to prepare a kind of new, with the more high bioactivity than scutelloside metal-scutelloside complex, the metal-scutelloside complex can be used for treating grice diarrhoea.
Description
Technical field
The present invention relates to veterinary drug technical field, in particular to a kind of bismuth-scutelloside complex and its preparation method and application.
Background technique
The treatment most common method of grice diarrhoea is using antibacterials, but the drug resistance of bacterium is strong, and antibacterial is used for a long time
Drug, therapeutic effect are poor.There is the method using Chinese herbal treatment grice diarrhoea at present, for example, scutelloside.
Scutelloside is the main function ingredient of radix scutellariae, is a kind of flavone compound, has preferable antibacterial, anti-inflammatory function
It imitates, toxemic symptoms when can alleviate bacterium infection simultaneously have Conservative restoration effect to internal a variety of organs.The antibacterial examination of inside and outside
Verifying is real, and scutelloside has good bacteriostasis to Escherichia coli, staphylococcus aureus, Pseudomonas aeruginosa.It is controlled using scutelloside
Grice diarrhoea is treated, therapeutic effect is obvious.There is document report scutelloside that synthesis can be coordinated with copper (II), zinc (II), aluminium (III) to match
Object is closed, and after scutelloside and above-mentioned metal ion formation complex, original bioactivity has obtained different degrees of raising.But
Not all metal ions can cooperate with scutelloside to promote its bioactivity.Find the radix scutellariae of new treatment grice diarrhoea
Glycosides drug is of great significance to piglet cultivation.
Summary of the invention
The main object of the present invention is to propose a kind of bismuth-scutelloside complex and its preparation method and application, it is intended to be prepared
A kind of new, with the more high bioactivity than scutelloside metal-scutelloside complex, the metal-scutelloside complex can
For treating grice diarrhoea.
To achieve the above object, the invention proposes a kind of bismuth-scutelloside complex, the bismuth-scutelloside complexs
General molecular formula is (C21H17O11)(NO3)Bi·4H2O, the bismuth-scutelloside complex have structure shown in structural formula (1).
Structural formula (1):
To achieve the above object, above-mentioned for synthesizing the invention proposes a kind of bismuth-scutelloside complex preparation method
Bismuth-scutelloside complex, the bismuth-scutelloside complex preparation method the following steps are included:
Bismuth salt is dissolved in glycerite, bismuth ion precursor liquid is obtained；
The bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, bismuth-scutelloside complex is reacted to obtain.
Optionally, in the step of bismuth salt being dissolved in glycerite, obtaining bismuth ion precursor liquid,
The bismuth salt is bismuth nitrate；And/or
The glycerite is the aqueous solution of glycerol.
Optionally, in the step of bismuth salt being dissolved in glycerite, obtaining bismuth ion precursor liquid, in the bismuth ion precursor liquid
The mass concentration of the bismuth salt is 10~25%.
Optionally, in the step of bismuth salt being dissolved in glycerite, obtaining bismuth ion precursor liquid, the quality of the glycerite
Concentration is 30~60%.
Optionally, the bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, react bismuth-scutelloside is matched
Before the step of closing object further include:
Scutelloside is dissolved in the aqueous solution of triethylamine, obtains the scutelloside solution of pH7~9, wherein the triethylamine
In aqueous solution, the mass concentration of triethylamine is 0.8~1.5%.
Optionally, the bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, react bismuth-scutelloside is matched
In the step of closing object, the molar ratio of scutelloside and bismuth ion is 1:(1.1~1.6).
Optionally, the bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, react bismuth-scutelloside is matched
Close object the step of include:
The bismuth ion precursor liquid is added drop-wise to the scutelloside solution of pH7~9 with the rate of addition of 1.2~2.4mL/min
In, continue 60~120min of stirring, obtains mixed liquor；
After the mixed liquor is stood 2~4h, sediment is filtered to obtain；
It after the sediment is successively used distilled water, 60% ethanol washing, is dried in vacuo at 40~60 DEG C, obtains bismuth-Huang
A kind of reed mentioned in ancient books glycosides complex.
Optionally, the bismuth ion precursor liquid is added drop-wise to the radix scutellariae of pH7~9 with the rate of addition of 1.2~2.4mL/min
In glycosides solution, the step of continuing 60~120min of stirring, obtaining mixed liquor, carries out under the conditions of 25~45 DEG C of temperature.
In addition, the application the invention also provides above-mentioned bismuth-scutelloside complex in treatment grice diarrhoea.
In technical solution of the present invention, pass through space structure to scutelloside, various metals ion and different price bismuths
Coordination ability further investigation, the bismuth-scutelloside complex for proposing trivalent bismuth and scutelloside coordination synthesis have more than scutelloside
Good stability, drug effect more higher than scutelloside and antioxidant activity, and the effect of have both bismuth, it can be preferably by piglet body
It utilizes, good antimicrobial effect has also opened up broader space for bismuth element.In addition, being based on bismuth salt and scutelloside
Dissolution characteristics, select certain density glycerite as dissolution bismuth salt solvent, improve bismuth salt solubility, promoting reaction just
To progress, yield is effectively increased, and glycerol cannot participate in complex reaction, avoids the generation of by-product；And control scutelloside
The pH of solution destroys structure by strong acid or highly basic to avoid scutelloside and effectively increases production so as to avoid the generation of side reaction
Product purity.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technical description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention for those of ordinary skill in the art without creative efforts, can be with
Other relevant attached drawings are obtained according to these attached drawings.
Fig. 1 is the flow diagram of an embodiment of bismuth proposed by the present invention-scutelloside complex preparation method；
Fig. 2 is the infrared absorpting light spectra of scutelloside；
Fig. 3 is bismuth-scutelloside complex infrared spectrogram made from embodiment 1.
The embodiments will be further described with reference to the accompanying drawings for the realization, the function and the advantages of the object of the present invention.
Specific embodiment
It in order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below will be in the embodiment of the present invention
Technical solution be clearly and completely described.The person that is not specified actual conditions in embodiment, according to normal conditions or manufacturer builds
The condition of view carries out.Reagents or instruments used without specified manufacturer is the conventional production that can be obtained by commercially available purchase
Product.
The bacteriostatic test of inside and outside confirms that scutelloside has Escherichia coli, staphylococcus aureus, Pseudomonas aeruginosa good
Bacteriostasis.Grice diarrhoea is treated using scutelloside, therapeutic effect is obvious.Have document report scutelloside and copper (II), zinc (II),
After aluminium (III) can be coordinated synthetic compound, and scutelloside and above-mentioned metal ion form complex, original bioactivity is obtained
Different degrees of raising is arrived.But not all metal ions can cooperate with scutelloside to promote its bioactivity.It finds
The scutelloside drug of new treatment grice diarrhoea is of great significance to piglet cultivation.
Therefore, the invention proposes a kind of bismuth-scutelloside complex, the bismuth-scutelloside complex general molecular formula is
(C21H17O11)(NO3)Bi·4H2O, the bismuth-scutelloside complex have structure shown in structural formula (1).
Structural formula (1):
Bismuth salt is a kind of less toxic or Poisoning substance, has effects that physiological activation, and taking orally can be in stomach after containing bismuth medicine
The mucous membrane surface of a wound forms layer protecting film, mitigates stimulation of the food to stomach lining；Bismuth is in conjunction with hydrogen sulfide in chitling, in intestinal mucosa
It is upper to form undissolved bismuth sulfide, slow down enterocinesia, there is convergence, protection stomach lining and antibacterial action, to prevent piglet
Diarrhea protects growth of animal and production.Inventor passes through space structure, various metals ion and the different prices to scutelloside
The coordination ability of bismuth is furtherd investigate, and under certain condition by test of many times discovery, trivalent bismuth can be coordinated with scutelloside and synthesize
Complex with above structure, and the bismuth with above structure-scutelloside complex property is stablized, and has higher than scutelloside
Drug effect and antioxidant activity, and the effect of have both bismuth, can preferably be utilized by piglet body, improve the nutriment of animal
Digestibility and utilization rate inhibit the growth of pathogenic bacteria, have opened up broader space for bismuth element.
In addition, the synthesis of existing metal-scutelloside complex, is usually dissolved in sodium hydroxide, bicarbonate for scutelloside
The alkaline solutions such as sodium or 60% ethanol solution in, in alkalinity, under heating condition, generate gold with the reactant aqueous solution of metal salt
Category-scutelloside complex.But there is following problems for these synthetic methods: scutelloside is unstable in alkaline solution, structure
Easily occur to go bad, and metal ion is also easy to produce precipitating in alkaline solution, causes the by-product in product more, purity is low；It is yellow
A kind of reed mentioned in ancient books glycosides is not soluble in water, is slightly soluble in alcohol, and when using above-mentioned synthetic method, scutelloside cannot be completely dissolved, and participates in the scutelloside of reaction
It is less, cause product yield lower；Moreover, most of bismuth salt is insoluble in water or is easy hydrolysis, aqueous solution, Jin Erwu cannot be made
Method is used to prepare bismuth-scutelloside complex.
In consideration of it, being used to prepare above-mentioned bismuth-radix scutellariae the invention proposes a kind of bismuth-scutelloside complex preparation method
Glycosides complex, the preparation method simple process, easily controllable, yield is high, good product purity.Bismuth-the scutelloside proposed in conjunction with Fig. 1
The flow diagram of one embodiment of the preparation method of complex, the bismuth-scutelloside complex preparation method includes following
Step:
Step S10, bismuth salt is dissolved in glycerite, obtains bismuth ion precursor liquid.
Most of bismuth salt is insoluble in water or is easy hydrolysis, especially bismuth nitrate, and it is not soluble in water that generation can be hydrolyzed when being dissolved in water
Water basic salt precipitating, such as BiONO3、Bi2O2(OH)NO3And Bi6O4(OH)4(NO3)6·H2O, to be difficult to and scutelloside shape
At complex, and then the preparation of bismuth-scutelloside complex is influenced, and bismuth salt will not precipitate in the solution containing glycerol, favorably
Complex reaction occurs in subsequent bismuth ion and scutelloside molecule, improves reaction yield, moreover, glycerol molecule does not participate in cooperation instead
It answers, by-product will not be generated, influence product purity.Therefore, in the present embodiment, select glycerite as solvent, bismuth salt is molten
Bismuth ion precursor liquid is made in solution, to react with scutelloside solution.The molal weight score of bismuth ion precursor liquid bismuth salt is
10~25%.
In addition, glycerite is the aqueous solution of glycerol in the present embodiment.In glycerite, glycerol and water than regular meeting shadow
It rings and arrives the solubility of bismuth salt in the solution, be based on this, in the present embodiment, controlling mass concentration of the glycerol in glycerite is 30
~60%, with this condition, bismuth salt can sufficiently dissolve, and be conducive to improve reaction yield.
Further, bismuth salt can be any one bismuth salt for dissolving in glycerite, wherein and with the dissolution of bismuth nitrate effect
Fruit is best, is easier to that complex reaction occurs with scutelloside, therefore, in the present embodiment, bismuth salt is preferably bismuth nitrate (Bi (NO3)3·
5H2O)。
Step S20, the bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, reacts to obtain bismuth-scutelloside
Complex.
In the present embodiment, the bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, bismuth ion and radix scutellariae
Complex reaction occurs for glycosides, generates bismuth-scutelloside complex.
Under the conditions of pH7~9, the structure of scutelloside is not susceptible to go bad, and bismuth ion will not generate precipitating, it is easier to match
It closes reaction to carry out, is conducive to improve reaction yield and product purity.
Simultaneously as scutelloside molecule can be polymerize by hydrogen bond when scutelloside excess, colloidal solution is formed, so as to cause
Precipitating is not easy to crystallize out, and not only reduces yield, nor the reaction process that easily follows up, therefore, in the present embodiment, radix scutellariae
The molar ratio of glycosides and bismuth salt metal ion is 1:(1.1~1.6).
When it is implemented, step S20 can be realized by following steps:
Step S210, the bismuth ion precursor liquid is added drop-wise to the Huang of pH7~9 with the rate of addition of 1.2~2.4mL/min
In a kind of reed mentioned in ancient books glycosides solution, continues 60~120min of stirring, obtain mixed liquor.
Wherein, step S210 is carried out under the conditions of 25~45 DEG C of temperature.With this condition, complex reaction speed can be accelerated
Degree, promotes reaction forward to carry out.And since bismuth ion can generate complex precipitating in conjunction with scutelloside, by controlling rate of addition
And be stirred continuously, precipitating formation speed can be made moderate, and distribution is not assembled, and then the progress that reacts fully.
Step S220, after the mixed liquor being stood 2~4h, sediment is filtered to obtain.
Be filtered again after sufficient standing, can make precipitating sufficiently, improve the yield of sediment, wherein filtering be in order to
It is separated by solid-liquid separation, it, can also be using modes such as suction filtration, centrifugations in addition to the mode of filtering.
Step S230, after the sediment successively being used distilled water, 60% ethanol washing, vacuum is dry at 40~60 DEG C
It is dry, obtain bismuth-scutelloside complex.
Further, since different solvents influences whether the dissolubility of scutelloside and the stability of scutelloside, and then influence
The yield and product purity of subsequent complex reaction can also include preparing pH7~9 before step S20 in the present embodiment
The step of scutelloside solution:
Step S100, scutelloside is dissolved in the aqueous solution of triethylamine, obtains the scutelloside solution of pH7~9, wherein institute
It states in the aqueous solution of triethylamine, the mass concentration of triethylamine is 0.8~1.5%.
Compared to strong base solution and 60% ethanol solution, in the aqueous solution for the triethylamine that mass concentration is 0.8~1.5%
In, scutelloside not only stablize by property, is unlikely to deteriorate, reduces the generation of by-product, improves yield, and in scutelloside molecule
Hydroxyl be easy to dissociate, be conducive to the combination of scutelloside and bismuth ion, carry out, effectively increase toward positive direction to promote to react
Yield.
It should be noted that step S100 and step S10 are not present sequencing, step S100 can step S10 it
Before, carry out later or simultaneously.
Preparation method simple process proposed by the present invention, easily controllable, production scutelloside-bismuth complex finished product yield
It can achieve 99.23~99.81%, purity can achieve 99.32~99.89%.
In addition, the application the invention also provides above-mentioned bismuth-scutelloside complex in treatment grice diarrhoea.
The bacteriostatic test of inside and outside confirms that scutelloside has Escherichia coli, staphylococcus aureus, Pseudomonas aeruginosa good
Bacteriostasis.Bismuth salt is a kind of less toxic or Poisoning substance, has effects that physiological activation, and taking orally can be in stomach after containing bismuth medicine
The mucous membrane surface of a wound forms layer protecting film, mitigates stimulation of the food to stomach lining.Bismuth-scutelloside that bismuth salt and scutelloside are formed cooperates
Object, property are stablized, and are substantially better than scutelloside for the extracorporeal extracorporeal suppression of drug-resistant type and sensitive swine Escherichia coli, and have both
The effect of bismuth salt itself, can be used for treating grice diarrhoea, inhibit the growth of pathogenic bacteria, improve the nutritive digestibility of animal
And utilization rate, it is beneficial to piglet growth.Its application mode can be to be taken directly as therapeutic agent, and dosage is daily
50~100mg/kg.bw is used in conjunction 3~5；It can also be used as additive and be used to prepare pig starter feed, veterinary drug or premix etc..
Technical solution of the present invention is described in further detail below in conjunction with specific embodiments and the drawings, it should be understood that
Following embodiment is only used to explain the present invention, is not intended to limit the present invention.
Embodiment 1
By 8.04mmol Bi (NO3)3·5H230% glycerite is added in 100ml small beaker in O (3.9g), stirs molten
Solution, obtains 10% bismuth ion precursor liquid；
6.7mmol scutelloside is placed in 250ml there-necked flask, 0.8% triethylamine solution 100ml is added, is mixed,
Obtain the scutelloside solution that pH is 7；
In 25 DEG C, above-mentioned bismuth ion precursor liquid is slowly dropped to by addition funnel with the speed of 1.2ml/min and is equipped with
In the there-necked flask of scutelloside solution, under stiring, occur complex precipitating immediately after bismuth ion and scutelloside generation complex reaction,
After being added dropwise, continue to stir 60min at 25 DEG C, reacts to obtain precipitating mixed liquor；
After mixed liquor standing 3h will be precipitated, filters to obtain precipitating, precipitating is successively respectively washed with distilled water, 60% ethanol solution
It is 3-5 times, then dry under 40 DEG C of vacuum conditions, orange scutelloside-bismuth complex finished product is made.
With the content of bismuth in inductance Coupled Plasma-Emission spectroscopic methodology (ICP-OES) measurement product, calculating yield is
99.51%, product purity 99.89%.
Embodiment 2
Weigh 10.72mmol Bi (NO3)3·5H2O (5.2g) is added 55% glycerite, stirs in 100ml small beaker
Dissolution is mixed, 20.8% bismuth ion precursor liquid is obtained；
6.7mmol scutelloside is placed in 250ml there-necked flask, 1.5% triethylamine solution 100ml is added, is mixed, obtains
The scutelloside solution that pH is 9；
In 45 DEG C, above-mentioned bismuth ion precursor liquid is slowly dropped to by addition funnel with the speed of 2.4ml/min and is equipped with
In the there-necked flask of scutelloside solution, under stiring, bismuth ion precipitates immediately after complex reaction occurs with scutelloside, drips
Bi Hou continues to stir 120min at 45 DEG C, reacts to obtain fluid,matching；
After fluid,matching is stood 4h, precipitating is filtered to obtain, precipitating is successively respectively washed into 3-5 with distilled water, 60% ethanol solution
It is secondary, it is then dry under 55 DEG C of vacuum conditions, orange bismuth-scutelloside complex finished product is made.
With the content of bismuth in inductance Coupled Plasma-Emission spectroscopic methodology (ICP-OES) measurement product, calculating yield is
99.69%, product purity 99.92%.
Embodiment 3
Weigh 9.38mmol Bi (NO3)3·5H2O (4.55g) is added in 45% glycerite in 100ml small beaker,
Stirring and dissolving obtains 22.75% bismuth ion precursor liquid；
6.7mmol scutelloside is placed in 250ml there-necked flask, 1.0% triethylamine solution of 100ml is added, is mixed,
Obtain the scutelloside solution that pH is 8.3；
In 35 DEG C, above-mentioned bismuth ion precursor liquid is slowly dropped to by addition funnel with the speed of 2.0ml/min and is equipped with
In the there-necked flask of scutelloside solution, under stiring, bismuth ion precipitates immediately after complex reaction occurs with scutelloside, drips
Bi Hou continues to stir 90min at 45 DEG C, reacts to obtain fluid,matching；
After fluid,matching is stood 2h, precipitating is filtered to obtain, will successively respectively be washed 3-5 times with distilled water, 60% ethanol solution, so
It is dry under 60 DEG C of vacuum conditions afterwards, orange bismuth-scutelloside complex finished product is made.
With the content of bismuth in inductance Coupled Plasma-Emission spectroscopic methodology (ICP-OES) measurement product, calculating yield is
99.54%, product purity 99.78%.
Embodiment 4
Weigh 10.05mmolBi (NO3)3·5H2O (4.874g) is added 40% glycerite, stirs in 100ml small beaker
Dissolution is mixed, 25% bismuth ion precursor liquid is obtained；
6.7mmol scutelloside is placed in 250ml there-necked flask, 1.2% triethylamine of 100ml is added, is mixed, obtains pH
For 8.6 scutelloside solution；
In 30 DEG C, above-mentioned bismuth ion precursor liquid is slowly dropped to by addition funnel with the speed of 1.5ml/min and is equipped with
In the there-necked flask of scutelloside solution, under stiring, bismuth ion precipitates immediately after complex reaction occurs with scutelloside, drips
Bi Hou continues to stir 80min at 30 DEG C, reacts to obtain fluid,matching；
After fluid,matching is stood 4h, precipitating is filtered to obtain, precipitating is successively respectively washed into 3-5 with distilled water, 60% ethanol solution
It is secondary, it is then dry under 50 DEG C of vacuum conditions, orange bismuth-scutelloside complex finished product is made.
With the content of bismuth in inductance Coupled Plasma-Emission spectroscopic methodology (ICP-OES) measurement product, calculating yield is
99.78%, product purity 99.86%.
Embodiment 5
Weigh 8.71mmol Bi (NO3)3·5H2O (4.224g) is added 60% glycerite, stirs in 100ml small beaker
Dissolution is mixed, 16.9% bismuth ion precursor liquid is obtained；
6.7mmol scutelloside is placed in 250ml there-necked flask, 1.1% triethylamine of 100ml is added, is mixed, obtains pH
For 8.4 scutelloside solution；
In 40 DEG C, above-mentioned bismuth ion precursor liquid is slowly dropped to by addition funnel with the speed of 1.8ml/min and is equipped with
In the there-necked flask of scutelloside solution, under stiring, bismuth ion precipitates immediately after complex reaction occurs with scutelloside, drips
Bi Hou continues to stir 100min at 40 DEG C, reacts to obtain fluid,matching；
After fluid,matching is stood 2.5h, precipitating is filtered to obtain, precipitating is successively respectively washed into 3- with distilled water, 60% ethanol solution
It is 5 times, then dry under 60 DEG C of vacuum conditions, orange bismuth-scutelloside complex finished product is made.
With the content of bismuth in inductance Coupled Plasma-Emission spectroscopic methodology (ICP-OES) measurement product, calculating yield is
99.63%, product purity 99.72%.
Embodiment 6
By 7.37mmol Bi (NO3)3·5H248% glycerite, stirring is added in 100ml small beaker in O (7.37g)
Dissolution, obtains 24.56% bismuth ion precursor liquid；
6.7mmol scutelloside is placed in 250ml there-necked flask, 0.9% triethylamine solution 30ml is added, is mixed, obtains
The scutelloside solution that pH is 8.1；
In 28 DEG C, above-mentioned bismuth ion precursor liquid is slowly dropped to by addition funnel with the speed of 1.6ml/min and is equipped with
In the there-necked flask of scutelloside solution, under stiring, bismuth ion precipitates immediately after complex reaction occurs with scutelloside, drips
Bi Hou continues to stir 120min at 28 DEG C, reacts to obtain fluid,matching；
After fluid,matching is stood 3.5h, precipitating is filtered to obtain, precipitating is successively respectively washed into 3- with distilled water, 60% ethanol solution
It is 5 times, then dry under 40 DEG C of vacuum conditions, orange cerium-scutelloside complex finished product is made.
With the content of cerium in inductance Coupled Plasma-Emission spectroscopic methodology (ICP-OES) measurement product, calculating yield is
99.54%, product purity 99.87%.
Fungistatic effect detection is carried out to bismuth made from the various embodiments described above-scutelloside complex finished product respectively.
Choose 20 plants of escherichia coli for pigs and Escherichia coli type strain ATCC25922 by Serotype Identification.
The external minimal inhibitory concentration of Escherichia coli (MIC) is measured using 96 orifice plate coubling dilutions, made from scutelloside and each embodiment
Bismuth-scutelloside complex finished product is as shown in table 1 to the external minimal inhibitory concentration value of 21 plants of swine Escherichia colis.
The MIC value (μ g/mL) of 1 scutelloside of table and bismuth-scutelloside to Escherichia coli
As can be seen from the above table, bismuth made from each embodiment-scutelloside complex is big for drug-resistant type and sensitive pig source
The In Vitro Bacteriostasis effect of enterobacteria is substantially better than scutelloside.Illustrate that bismuth prepared by the present invention-scutelloside complex can be used as one
The drug of kind efficiently, less toxic is for treating early-weaned piglets diarrhea.
Infrared spectrum analysis is carried out to product made from scutelloside and embodiment 1 respectively, as shown in Figures 2 and 3.
C=O absorption peak in Fig. 2 on scutelloside 4 is in 1661.9cm-1Locate, the C=O absorption peak red shift in Fig. 3 on 4
To 1617.98cm-1, illustrate that the hydroxyl on C=O and 5 on scutelloside 4 is coordinated with bismuth ion jointly, electron cloud
Density reduces, and illustrates that bismuth ion and scutelloside form stable complex in product prepared by preparation method of the present invention.
The above is only a preferred embodiment of the present invention, is not intended to limit the scope of the invention, for this field
For technical staff, the invention may be variously modified and varied.All within the spirits and principles of the present invention, made any
Modification, equivalent replacement, improvement etc. should all be included within the scope of the present invention.
Claims (10)
1. a kind of bismuth-scutelloside complex, which is characterized in that the bismuth-scutelloside complex general molecular formula is (C21H17O11)
(NO3)Bi·4H2O, the bismuth-scutelloside complex have structure shown in structural formula (1).
Structural formula (1):
2. a kind of preparation method of bismuth as described in claim 1-scutelloside complex, which comprises the following steps:
Bismuth salt is dissolved in glycerite, bismuth ion precursor liquid is obtained；
The bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9, bismuth-scutelloside complex is reacted to obtain.
3. bismuth as claimed in claim 2-scutelloside complex preparation method, which is characterized in that it is molten that bismuth salt is dissolved in glycerol
In liquid, in the step of obtaining bismuth ion precursor liquid,
The bismuth salt is bismuth nitrate；And/or
The glycerite is the aqueous solution of glycerol.
4. bismuth as claimed in claim 2-scutelloside complex preparation method, which is characterized in that it is molten that bismuth salt is dissolved in glycerol
In liquid, in the step of obtaining bismuth ion precursor liquid, the mass concentration of bismuth salt described in the bismuth ion precursor liquid is 10~25%.
5. bismuth as claimed in claim 2-scutelloside complex preparation method, which is characterized in that it is molten that bismuth salt is dissolved in glycerol
In liquid, in the step of obtaining bismuth ion precursor liquid, the mass concentration of the glycerite is 30~60%.
6. bismuth as claimed in claim 2-scutelloside complex preparation method, which is characterized in that by the bismuth ion forerunner
Drop is added in the scutelloside solution of pH7~9, react bismuth-scutelloside complex the step of before further include:
Scutelloside is dissolved in the aqueous solution of triethylamine, the scutelloside solution of pH7~9 is obtained, wherein the triethylamine it is water-soluble
In liquid, the mass concentration of triethylamine is 0.8~1.5%.
7. bismuth as claimed in claim 2-scutelloside complex preparation method, which is characterized in that by the bismuth ion forerunner
Drop is added in the scutelloside solution of pH7~9, react bismuth-scutelloside complex the step of in, scutelloside and bismuth ion rub
You are than being 1:(1.1~1.6).
8. bismuth as claimed in claim 2-scutelloside complex preparation method, which is characterized in that by the bismuth ion forerunner
Drop is added in the scutelloside solution of pH7~9, react bismuth-scutelloside complex the step of include:
The bismuth ion precursor liquid is added drop-wise in the scutelloside solution of pH7~9 with the rate of addition of 1.2~2.4mL/min, after
60~120min of continuous stirring, obtains mixed liquor；
After the mixed liquor is stood 2~4h, sediment is filtered to obtain；
It after the sediment is successively used distilled water, 60% ethanol washing, is dried in vacuo at 40~60 DEG C, obtains bismuth-scutelloside
Complex.
9. bismuth as claimed in claim 8-scutelloside complex preparation method, which is characterized in that by the bismuth ion forerunner
Liquid is added drop-wise in the scutelloside solution of pH7~9 with the rate of addition of 1.2~2.4mL/min, is continued 60~120min of stirring, is obtained
The step of mixed liquor, carries out under the conditions of 25~45 DEG C of temperature.
10. a kind of application of bismuth as described in claim 1-scutelloside complex in treatment grice diarrhoea.
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