CN108690110A - The preparation method of one boar mixed feeding scutelloside copper complex - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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Abstract
The invention discloses the preparation methods of a boar mixed feeding scutelloside copper complex, are related to veterinary drug synthesis field, this method is using the synthesis for carrying out complex in acetic acid-ammonium acetate buffer solution medium;For the pH value of the acetic acid-ammonium acetate buffer solution 5~6, the optimum molar proportion that feeds intake of the scutelloside and copper salt solution is 1:1.41~1.85.The compound activity is stablized, and has stronger bacteria resistance function, and medicinal effects are more preferable, can be used as feed addictive use.The present invention also provides the preparation methods of the substance, and this method is simple, and easy to control, so as to the large-scale preparation method as above-mentioned scutelloside copper complex, and have higher yield, final product purity is high.
Description
Technical field
The present invention relates to the synthesis fields of veterinary drug complex, and in particular to the system of a boar mixed feeding scutelloside copper complex
Preparation Method.
Background technology
Scutelloside is the main function ingredient of baikal skullcap root, is a kind of flavone compound, is had antibacterial, anti-inflammatory, disease-resistant
The effects that poison, diuresis, scavenging activated oxygen, and there is certain antitumor response physiological potency.Application study show scutelloside with
The complex that metal ion-chelant generates can increase its biological effect and antioxidant activity, and better than scutelloside antibacterial activity,
Development and application values are had more in husbandry sector.When metal ion forms complex with scutelloside, other coordination bodily forms are introduced
The multicomponent complex of Cheng Xin can more increase its activity, and more conducively human body or animal absorb, this is because the different coordination bodily forms
At scutelloside complex drug effect improved.
In realizing process of the present invention, inventor has found that at least there are the following problems in the prior art:Existing metal-Huang
It is molten to be typically dissolved in the alkalinity such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate by the synthesis of a kind of reed mentioned in ancient books glycosides complex for scutelloside
In liquid, or be dissolved in one or more of mixed solutions of nonaqueous solvents such as methanol, ethyl alcohol, ethyl acetate and petroleum ether, compared with
When the metal salt solution of copper and scutelloside being carried out chelatropic reaction under weak basic condition, often has Kocide SD and copper carbonate is heavy
It forms sediment and generates, these precipitations can come out with obtained complex coprecipitation, it is difficult to which washing removes, and often leads to product purity not
Height, existing impurity on the drug effect of product influence very big therefore current scutelloside copper complex synthesis and purifying there is
Problem.
Invention content
In order to overcome the shortcomings of that Related product in the prior art, the present invention propose boar mixed feeding scutelloside copper cooperation
The preparation method of object, scutelloside copper complex product purity and high income, the good drug efficacy prepared, no Kocide SD and copper carbonate
Precipitation generates, and solves the problems, such as that the preparation process moderate purity of current scutelloside copper complex is not high, Product Activity is poor.In addition originally
The new configuration scutelloside copper complex prepared is invented, satisfied result is also achieved for treating grice diarrhoea.Through experiment in vitro
Show that there is stronger bacteriostatic activity in treating grice diarrhoea, compared with scutelloside, medicinal effects are more preferable.
In order to achieve the above object, the present invention is achieved by the following technical programs, preparation method includes following step
Suddenly:.
S1:Prepare acetic acid-ammonium acetate buffer solution:Ammonium acetate is weighed in 2000 mL distilled water, is dissolved by heating, is added
50% acetic acid solution adjusts pH5~6, spare.
S2:Prepare scutelloside solution:The buffer solution 100mL of S1 is measured in there-necked flask, scutelloside powder, heating is added
Stirring and dissolving obtains yellow-green soln.
S3:Copper salt solution is prepared, mantoquita is dissolved in the buffer solution of 100mL S1, obtains blue solution.
S4:S3 is obtained copper salt solution to be slowly dropped in middle S2 scutellosides solution by separatory funnel, and heats and stirs
It mixes, obtained brown color sediment is filtered, absolute ethyl alcohol washs, dry, obtains yellow-brown solid scutelloside copper complex.
Preferably, in the acetic acid-ammonium acetate buffer solution of pH5~6, the volumetric concentration of 50% acetic acid solution is 0.50%~
1.2%, the molar concentration of ammonium acetate is 0.62~0.85mol/L.
Preferably, in S2 steps scutelloside 100 mL acetic acid-ammonium acetate buffer solutions input mass concentration be 2.5%
~3.5%.
Preferably, heating temperature is 30~70 DEG C, preferably 58 DEG C in step S2 reactions.
Preferably, the copper salt solution in S3 is derived from one kind or two kinds of copper acetate, copper sulphate, copper chloride or copper nitrate,
It is preferred that copper acetate.
Preferably, the rate of addition of copper salt solution is 1~2.5 mL/min.
Preferably, the optimum proportioning that feeds intake of scutelloside and copper salt solution by molar amount is 1 in S4 steps:1.41~
1.85。
Preferably, the reaction time is 30~85 min in step S4;Preferably 70~78 min.
Product obtained above is carried out structural characterization by the present invention with UV, Infra-red, MS etc. respectively, is determined as radix scutellariae
Glycosides copper complex.
The complex is daily 50~100mg/kg.bw for treating grice diarrhoea, dosage, is used in conjunction 3~5.
The above technical scheme of the present invention provides a kind of scutelloside copper complex, which stablizes, for resistance to
Types of Medicine and the extracorporeal extracorporeal suppression of sensitive swine Escherichia coli are substantially better than scutelloside.At the same time, the substance is provided
Preparation method, so as to the large-scale preparation method as above-mentioned scutelloside copper complex;In addition, this method is simple for process,
It is easily controllable, and there is higher content and yield.
Description of the drawings
Fig. 1 scutelloside copper complex preparation flow figures of the present invention;
Fig. 2 scutelloside copper complex structure charts of the present invention;
Fig. 3 scutelloside infrared spectrograms of the present invention;
Fig. 4 scutelloside copper complex infrared spectrograms of the present invention;
Fig. 5 scutelloside copper complex mass spectrograms of the present invention.
Specific implementation mode
Embodiment 1:
The acetic acid-ammonium acetate buffer solution that 100 mL pH are 6 is added in there-necked flask, it is 92% radix scutellariae to weigh 3g purity
For glycosides in there-necked flask, heating stirring dissolves to obtain yellow-green soln, and 5% copper acetate solution is then added dropwise by separatory funnel(Acetic acid
Copper is previously dissolved in the buffer solution for acetic acid-ammonium acetate that pH is 6), rate of addition is 1.0 mL, is stirred to react under the conditions of 50 DEG C
85min obtains brown color precipitation, filters, and washing is dry to obtain yellow-brown solid to constant weight, analyzes and identifies as scutelloside copper complex,
Its yield 95.17%, purity 99.52%.
Embodiment 2:
The acetic acid-ammonium acetate buffer solution that 100 mL pH are 5.5 is added in there-necked flask, it is 92% to weigh 2.5g purity
For scutelloside in there-necked flask, heating stirring dissolves to obtain yellow-green soln, and 4% copper acetate solution is then added dropwise by separatory funnel
(Copper acetate is previously dissolved in the buffer solution for acetic acid-ammonium acetate that pH is 5), rate of addition is 2.5 mL, is stirred under the conditions of 55 DEG C
It mixes 65 min of reaction and obtains brown color precipitation, filter, washing is dry to obtain yellow-brown solid to constant weight, analyzes and identifies as scutelloside copper
Complex, yield 96.78%, purity 99.43%.
Embodiment 3:
The acetic acid-ammonium acetate buffer solution that 100 mL pH are 5 is added in there-necked flask, weighs the Huang that 3.5g purity is 92%
For a kind of reed mentioned in ancient books glycosides in there-necked flask, heating stirring dissolves to obtain yellow-green soln, and 2% copper acetate solution is then added dropwise by separatory funnel(Second
Sour copper is previously dissolved in the buffer solution for acetic acid-ammonium acetate that pH is 5), rate of addition is 2.0 mL, is stirred under the conditions of 50 DEG C anti-
It answers 75 min to obtain brown color precipitation, filters, washing is dry to obtain yellow-brown solid to constant weight, analyzes and identifies and coordinates for scutelloside copper
Object, yield 96.36%, purity 99.17%.
Embodiment 4:
The acetic acid-ammonium acetate buffer solution that 100 mL pH are 6 is added in there-necked flask, weighs the radix scutellariae that 3g purity is 92%
For glycosides in there-necked flask, heating stirring dissolves to obtain yellow-green soln, and 3% copper-bath is then added dropwise by separatory funnel(Sulfuric acid
Copper is previously dissolved in the buffer solution for acetic acid-ammonium acetate that pH is 6), rate of addition is 1.5 ml, is stirred under the conditions of 60 DEG C anti-
It answers 70min to obtain brown color precipitation, filters, washing is dry to obtain yellow-brown solid to constant weight, analyzes and identifies and coordinates for scutelloside copper
Object, yield 95.31%, purity 99.62%.
Embodiment 5:
The acetic acid-ammonium acetate buffer solution that 150 mL pH are 5.8 is added in there-necked flask, weighs the Huang that 5g purity is 92%
For a kind of reed mentioned in ancient books glycosides in there-necked flask, heating stirring dissolves to obtain yellow-green soln, and 6% copper chloride solution is then added dropwise by separatory funnel(Chlorine
Change the buffer solution that copper is previously dissolved in acetic acid-ammonium acetate that pH is 5.8), rate of addition is 1.8 mL, is stirred under the conditions of 63 DEG C
Reaction 57min obtains brown color precipitation, filters, and washing is dry to obtain yellow-brown solid to constant weight, analyzes and identifies and coordinates for scutelloside copper
Object, yield 96.37%, purity 99.32%.
In certain embodiments, with a kind of instead of copper acetate in copper sulphate, copper chloride or copper nitrate.
In certain embodiments, in 100 mL acetic acid-ammonium acetate buffer solutions, the amount of weighing of 92% scutelloside be 1g,
1.5g, 2g, 2.5g, 3g or 3.5g etc., preferably 2.5g.
In certain embodiments, mantoquita is dissolved in 100 mL acetic acid-ammonium acetate buffer solutions, mantoquita a concentration of 3%,
4%, 4.5%, 5%, 5.5% or 6%, preferably 5%.
In certain embodiments, the pH of the buffer solution of acetic acid-ammonium acetate is 5,5.5 or 6, preferably 6.
Embodiment 6:
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 is measured using 96 orifice plate coubling dilutions(MIC), 21 plants of scutelloside and scutelloside copper pair
The external minimal inhibitory concentration value of swine Escherichia coli is as shown in table 1.
The MIC value (μ g/mL) of 1 scutelloside of table and scutelloside copper to Escherichia coli
Show that scutelloside copper is bright for the In Vitro Bacteriostasis effect of drug-resistant type and sensitive swine Escherichia coli from 1 test result of table
It is aobvious to be better than scutelloside.As a kind of new efficient, less toxic drug, there is great meaning in treatment early-weaned piglets diarrhea
Justice.
A. in scutelloside copper complex copper content analysis:
0.1000g scutelloside copper complexes are weighed, with aqua regia dissolution, constant volume is inhaled after 250mL volumetric flasks, appropriate dilution with atom
The content that spectrometer measures copper is received, it is as a result as follows:
Theoretical value Cu:10.88
Test value Cu:10.95
Compared by the actual measured value of above-mentioned copper content, content is close to theoretical value, it may be determined that the coordination of the compound
Only it is complexed with a scutelloside ligand.
B. ultraviolet spectral analysis
2 scutelloside of table and UV absorption wavelength of the complex in DMSO- methanol solutions
| Maximum absorption wavelength (nm) | Wavelength (nm) | |
| Scutelloside | 275 | 309.9 |
| Scutelloside copper | 290 |
As known from Table 2, the scutelloside and each substance maximum absorption wavelength measured in DMSO- methanol, scutelloside in 275nm and
309.9nm has absorption maximum at two;It is 290nm that scutelloside copper complex, which only has UV absorption at one, and ultraviolet suction at 309.9nm
It receives and disappears.Show that scutelloside is really reacted with metal ion.The reason of UV absorption generation red shift, is coordinated due to being formed
The increase of delocalization degree and metal ion for making electronics in entire molecule after object have certain electron-withdrawing ability, are conjugated member ring systems
Electron cloud is moved to the metal of planar central, and the excitation needed for electron transition is enable to reduce, so red shift occurs for absorption peak.
Infrared spectrum analysis
Scutelloside, scutelloside copper infrared results be analyzed as follows:
The absorption peak of C=O(It is flexible)In 1850-1600 cm-1Between.In the infared spectrum of scutelloside, 4 C=O of scutelloside
Absorption peak(Stretching vibration peak)For 1660.4 cm-1, and the red shift of C=O absorption peaks is to 1629.5cm in scutelloside copper complex-1,
The reason of leading to absorption peak red shift is that the lone pair electrons of oxygen and the unoccupied orbital of metal ion form coordinate bond and metal ion and make electricity
Sub- delocalization and cause the cloud density of C=O bond to reduce, so that force constant is become smaller, so as to cause Red Shift Phenomena.Thus illustrate,
The binding site of scutelloside and metal ion may be 4 carbonyls.
Alcohol, phenol free O-H keys absorption peak in 3650-3580cm-1Between, association O-H key absorption peaks are in 3400-
3200cm-1Between, and the free O-H keys 3540-3350cm of carboxylic acid-1Between.5 hydroxyls of scutelloside can occur with 4 carbonyls
Intramolecular hydrogen bond associates, then peak is located at 3400-3200cm-1Between, dissociate the hydroxyl position in scutelloside on carboxylic acid O-H keys, then peak
Positioned at 3540-3350cm-1Between.Since these 0-H absorption peaks are very wide, and many hydroxyls also in other positions, cause this
A little O-H absorption peaks are in 3600-3lOOcm-1Between formed a big broad peak, it is difficult to differentiate the position corresponding to each O-H.Radix scutellariae
In glycosides infared spectrum, the big broad peak that these 0-H keys are formed is in 3289.9cm-1There is absorption peak at place.And in the infrared figure of scutelloside copper
In spectrum, the peak is from 3289.9cm-1It is moved to 3405.6cm-1, i.e. blue shift has occurred in absorption peak, illustrates intramolecular hydrogen bond by broken
It is bad, it can be seen that may be that 5 hydroxyls are coordinated with metal ion.
By ultraviolet and infrared results it is found that the ultraviolet and infrared absorption of product relative raw material (scutelloside) has occurred significantly
Variation illustrates that complex reaction has occurred with copper ion in scutelloside, and coordination site may be 4 carbonyls, 5 hydroxyls.
The mass spectral analysis of scutelloside copper
The intensity of fragment peak 890.5 is larger, according to 2446.35-2=890.7, it may be possible to two scutelloside molecules(446.35)
Association loses 2 hydrogen(1).The intensity of fragment peak 602.7 is larger, according to 579+23=602, it may be possible to due to molecular ion
(579), obtain an ammonium ion(23).The intensity of fragment peak 580.8 is larger, according to 579+2=581, it may be possible to due to molecule from
Son(579), obtain two hydrogen ions(2).The intensity of fragment peak 558.8 is larger, according to 579-23+2=558, it may be possible to due to dividing
Daughter ion(579), lose an ammonium ion(23), obtain two hydrogen ions(2).The intensity of fragment peak 524.8 is larger, according to
579-23-31=525, it may be possible to due to molecular ion(579), lose an ammonium ion(23)With a coordination methoxy group
(31).The intensity of fragment peak 466.9 is larger, according to 468-1=467, it may be possible to scutelloside ammonium(468), lose a hydrogen ion
(1).The intensity of fragment peak 444.9 is larger, according to 446.36-1=445.36, it may be possible to scutelloside(446.36), lose a hydrogen
Ion(1).
In second order spectrum, the cracking of fragment peak 602.7 has obtained 508.8 and 466.8 two fragment peaks.Fragment peak 508.8
Intensity it is larger, according to 602.7-223-18-31+1=508.7, it may be possible to which 602.7 structure of fragment peak loses two ammonium ions
(223=46), lose coordination hydrone (18), lose coordination methoxy group(31), obtain 1 hydrogen ion(1).
The above technical scheme of the present invention provides firstly a kind of scutelloside copper complex, which stablizes, right
It is with obvious effects better than scutelloside in the In Vitro Bacteriostasis of drug-resistant type and sensitive swine Escherichia coli.At the same time, the object is provided
The preparation method of matter, so as to the large-scale preparation method as above-mentioned scutelloside copper complex;In addition, this method technique letter
It is single, it is easily controllable, and there is higher content and yield.
Comparative example 1:.
Scutelloside is dissolved in 5% sal volatile and obtains a brown-red solution(A liquid), by copper acetate or copper sulphate point
It is not dissolved in nonaqueous solvents ethyl acetate(B liquid), A liquid and B liquid are pressed into different mol ratio(2:1,1:1,1:1.5)Ratio 50
It is stirred to react at a temperature of DEG C 3 hours, obtains brown color precipitation, washed repeatedly with absolute ethyl alcohol, dried;Yield 78.71%, purity
It is 87.3%.
Comparative example 2:.
Scutelloside is dissolved in 60% ethanol solution and obtains a brown-red solution(A liquid), copper acetate or copper sulphate distinguished
It is dissolved in 60% ethyl alcohol of nonaqueous solvents(B liquid), A liquid and B liquid are pressed into different mol ratio(2:1,1:1,1:1.5)Ratio at 60 DEG C
At a temperature of be stirred to react 4 hours, obtain brown color precipitation, wash repeatedly with absolute ethyl alcohol, drying.Yield 82.81%, purity are
89.3%。
Claims (7)
1. the preparation method of a boar mixed feeding scutelloside copper complex, it is characterised in that:Include the following steps,
(1) scutelloside, mantoquita are dissolved in the acetic acid-ammonium acetate buffer solution of pH5~6 respectively;
(2) copper salt solution being slowly dropped in scutelloside solution, rate of addition is 1~2.5 ml, in a heated condition, into
Row stirring, fully reacts, and the mole ratio of mantoquita and scutelloside substance is 1 in the reaction solution:1.41~1.85;
(3) brown color of gained is precipitated, filtering is washed with ethanol solution, dried to get the scutelloside copper complex.
2. the preparation method of boar mixed feeding scutelloside copper complex according to claim 1, it is characterised in that:It is described
The molar feed ratio of reaction be scutelloside, mantoquita amount ratio be 1:1~2, preferably 1:1.41~1.85.
3. the preparation method of boar mixed feeding scutelloside copper complex according to claim 2, it is characterised in that:Second
Acid-ammonium acetate buffer solution pH5~6.
4. the preparation method of boar mixed feeding scutelloside copper complex according to claim 2, it is characterised in that:It is described
Mantoquita be copper formate, copper acetate, copper sulphate, one or both of copper chloride, preferably copper acetate.
5. a kind of preparation method for treating grice diarrhoea scutelloside copper complex according to claim 2, feature
It is:The rate of addition of the copper salt solution is 1~2.5 mL, preferably 2 mL.
6. the preparation method of boar mixed feeding scutelloside copper complex according to claim 2, it is characterised in that:It is described
Reaction temperature be 30~85 DEG C, preferably 58 DEG C.
7. the preparation method of boar mixed feeding scutelloside copper complex according to claim 2, it is characterised in that:It is described
Reaction time be 30~85 min, preferably 70-78min.
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| CN110003294A (en) * | 2019-04-30 | 2019-07-12 | 武汉轻工大学 | A kind of preparation method of copper cobalt nickel-scutelloside complex |
| CN110003296A (en) * | 2019-04-29 | 2019-07-12 | 武汉轻工大学 | A kind of preparation method and application of zinc-scutelloside complex |
| CN110169511A (en) * | 2019-06-25 | 2019-08-27 | 武汉轻工大学 | One boar food and preparation method thereof |
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| CN110003296A (en) * | 2019-04-29 | 2019-07-12 | 武汉轻工大学 | A kind of preparation method and application of zinc-scutelloside complex |
| CN110003294A (en) * | 2019-04-30 | 2019-07-12 | 武汉轻工大学 | A kind of preparation method of copper cobalt nickel-scutelloside complex |
| CN110169511A (en) * | 2019-06-25 | 2019-08-27 | 武汉轻工大学 | One boar food and preparation method thereof |
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