CN108486181B - High-purity allicin and preparation method thereof - Google Patents
High-purity allicin and preparation method thereof Download PDFInfo
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- CN108486181B CN108486181B CN201810055190.5A CN201810055190A CN108486181B CN 108486181 B CN108486181 B CN 108486181B CN 201810055190 A CN201810055190 A CN 201810055190A CN 108486181 B CN108486181 B CN 108486181B
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- C12P11/00—Preparation of sulfur-containing organic compounds
Abstract
The invention relates to the technical field of allicin preparation, in particular to high-purity allicin, which is obtained according to the following steps: in-vitro biosynthesis of allicin water solution by using alliin and allinase as raw materials; extracting the allicin aqueous solution by using a water-soluble organic solvent, and concentrating in a reduced pressure distillation mode to obtain an allicin organic concentrated solution; separating the components of the allicin concentrated solution by using a molecular distillation technology to obtain the high-purity allicin. The preparation process is simple, the raw materials are obtained by natural extraction, and the obtained high-purity allicin serving as a natural medicine has small toxic and side effects and no residue in organisms; the stability and purity of the high-purity allicin are greatly improved, the purity is more than or equal to 95.0 percent, and the safety, high efficiency and quality controllability of the product are realized.
Description
Technical Field
The invention relates to the technical field of biological medicines, and discloses high-purity allicin and a preparation method thereof.
Background
Garlic (Allium sativumL.) and its preparation are listed in United states and European Union pharmacopoeia, Allicin (Allicin, dipropenyl thiosulfinate, CAS: 539-86-6) is the main effective component, and has wide biological activity. When garlic tissue is crushed, the non-protein amino acid Alliin (Alliin, S-allyl cysteine sulfoxide, CAS: 556-27-4) is catalyzed by allinase and then reacts to generate allicin. As thiosulfinate, allicin performs its biological activity mainly in the form of active sulfur compound (RSS) participating in the oxidation-reduction reaction of glutathione and biologically functional proteins. The compound can inhibit and kill bacteria, fungi (the effect is comparable to broad spectrum antifungal fluconazole) and viruses in a dose-dependent manner, comprises a drug-resistant strain methicillin-resistant staphylococcus aureus (MRSA), and can also inhibit the proliferation of mammalian cells (comprising cancer cells) and even induce the death of the mammalian cells; allicin can also inhibit through regulation of activity or metabolism of various target proteins to produce endogenous transmitters: cholesterol synthesis, platelet aggregation, proliferation and transfer of vascular smooth muscle cells and inflammatory reaction, and has remarkable treatment and health care effects on the cardiovascular and cerebrovascular diseases with the highest death rate at present.
There are currently three main ways to obtain allicin: chemical synthesis, in vitro biosynthesis, and natural extraction, separation and purification. The three methods can obtain a certain amount of allicin, but the problems of complex operation, residual toxic substances, poor reproducibility and the like generally exist, and the key points are extremely low purity and yield. In addition, the allicin has active chemical properties, is easy to be oxidized and degraded and is sensitive to heat, so that no high-purity allicin product is released at home and abroad at present.
Disclosure of Invention
The invention provides high-purity allicin and a preparation method thereof, overcomes the defects of the prior art, and can effectively solve the problems of complex process operation, great toxic and side effects as natural medicines, residual toxic substances in organisms and low stability and purity of allicin in the existing preparation method of allicin.
One of the technical schemes of the invention is realized by the following measures: a high-purity allicin is obtained by the following steps: step one, synthesizing 1 mg/ml to 10 mg/ml allicin water solution in vitro according to the mass ratio of 1:0.1 to 2 by alliin and allinase under the environment isolated from air at the temperature of 0 ℃ to 10 ℃; secondly, adding a water-soluble organic solvent into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the water-soluble organic solvent of 1: 0.5-2, incubating for 5-20 min at the temperature of 15-40 ℃, centrifuging at a high speed for 5-30 min to obtain an allicin water-soluble organic solvent layer, and decompressing, rotary steaming and concentrating the allicin water-soluble organic solvent layer to obtain an allicin organic solution; thirdly, adding a fat-soluble organic solvent into the allicin organic solution for extraction, collecting an allicin fat-soluble organic solvent layer, and performing reduced pressure, rotary evaporation and concentration to obtain an allicin organic concentrated solution; and fourthly, performing molecular distillation and collection on the allicin organic concentrated solution to obtain the high-purity allicin.
The following is a further optimization or/and improvement of one of the above-mentioned technical solutions of the invention:
the purity of the alliin is more than or equal to 50 percent, and the activity of alliinase is more than or equal to 1000U/g.
The water-soluble organic solvent is one of methanol and ethanol; or/and the fat-soluble organic solvent is one of acetone and diethyl ether.
The conditions of decompression, rotary evaporation and concentration are that the temperature is 10 ℃ to 50 ℃, the pressure is 0bar to 0.05bar, and the rotating speed is 50rpm to 150 rpm; or/and the temperature during high-speed centrifugation is 4-15 ℃, and the centrifugation speed is 3000-12000 rpm.
Conditions of the above molecular distillation: the sample injection speed is 0.5 ml/min to 5 ml/min, the scraper speed is 5 rpm/min to 50 rpm/min, the external circulation temperature is 10 ℃ to-30 ℃, and the vacuum degree is 1torr to 100 torr.
The second technical scheme of the invention is realized by the following measures: a preparation method of high-purity allicin comprises the following steps: step one, synthesizing 1 mg/ml to 10 mg/ml allicin water solution in vitro according to the mass ratio of 1:0.1 to 2 by alliin and allinase under the environment isolated from air at the temperature of 0 ℃ to 10 ℃; secondly, adding a water-soluble organic solvent into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the water-soluble organic solvent of 1: 0.5-2, incubating for 5-20 min at the temperature of 15-40 ℃, centrifuging at a high speed for 5-30 min to obtain an allicin water-soluble organic solvent layer, and decompressing, rotary steaming and concentrating the allicin water-soluble organic solvent layer to obtain an allicin organic solution; thirdly, adding a fat-soluble organic solvent into the allicin organic solution for extraction, collecting an allicin fat-soluble organic solvent layer, and performing reduced pressure, rotary evaporation and concentration to obtain an allicin organic concentrated solution; and fourthly, performing molecular distillation and collection on the allicin organic concentrated solution to obtain the high-purity allicin.
The following is further optimization or/and improvement of the second technical scheme of the invention:
the purity of the alliin is more than or equal to 50 percent, and the activity of alliinase is more than or equal to 1000U/g.
The water-soluble organic solvent is one of methanol and ethanol; or/and the fat-soluble organic solvent is one of acetone and diethyl ether.
The conditions of decompression, rotary evaporation and concentration are that the temperature is 10 ℃ to 50 ℃, the pressure is 0bar to 0.05bar, and the rotating speed is 50rpm to 150 rpm; or/and the temperature during high-speed centrifugation is 4-15 ℃, and the centrifugation speed is 3000-12000 rpm.
Conditions of the above molecular distillation: the sample injection speed is 0.5 ml/min to 5 ml/min, the scraper speed is 5 rpm/min to 50 rpm/min, the external circulation temperature is 10 ℃ to-30 ℃, and the vacuum degree is 1torr to 100 torr.
The preparation process is simple, the raw materials are obtained by natural extraction, the obtained high-purity allicin is used as a natural medicine, the toxic and side effects are small, no residue exists in a living body, the purity of the obtained high-purity allicin is more than or equal to 95.0 percent, the stability and the purity are greatly improved, and the safety, the high efficiency and the quality controllability of the product are realized.
Detailed Description
The present invention is not limited by the following examples, and specific embodiments may be determined according to the technical solutions and practical situations of the present invention. The various chemical reagents and chemical articles mentioned in the invention are all the chemical reagents and chemical articles which are well known and commonly used in the prior art, unless otherwise specified; the percentages in the invention are mass percentages unless otherwise specified; the solution in the present invention is an aqueous solution in which the solvent is water, for example, a hydrochloric acid solution is an aqueous hydrochloric acid solution, unless otherwise specified; the normal temperature and room temperature in the present invention generally mean a temperature of 15 ℃ to 25 ℃, and are generally defined as 25 ℃.
The invention is further described below with reference to the following examples:
example 1: the high-purity allicin is obtained according to the following steps: step one, synthesizing 1 mg/ml to 10 mg/ml allicin water solution in vitro according to the mass ratio of 1:0.1 to 2 by alliin and allinase under the environment isolated from air at the temperature of 0 ℃ to 10 ℃; secondly, adding a water-soluble organic solvent into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the water-soluble organic solvent of 1: 0.5-2, incubating for 5-20 min at the temperature of 15-40 ℃, centrifuging at a high speed for 5-30 min to obtain an allicin water-soluble organic solvent layer, and decompressing, rotary steaming and concentrating the allicin water-soluble organic solvent layer to obtain an allicin organic solution; thirdly, adding a fat-soluble organic solvent into the allicin organic solution for extraction, collecting an allicin fat-soluble organic solvent layer, and performing reduced pressure, rotary evaporation and concentration to obtain an allicin organic concentrated solution; and fourthly, performing molecular distillation and collection on the allicin organic concentrated solution to obtain the high-purity allicin.
In vitro biosynthesis methods known in the art.
Example 2: the high-purity allicin is obtained according to the following steps: step one, synthesizing 1 mg/ml or 10 mg/ml allicin water solution in vitro according to the mass ratio of 1:0.1 or 2 and under the environment that the temperature is 0 ℃ or 10 ℃ and the air is isolated; secondly, adding a water-soluble organic solvent into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the water-soluble organic solvent of 1:0.5 or 2, incubating for 5 min or 20 min at the temperature of 15 ℃ or 40 ℃, centrifuging at a high speed for 5 min or 30 min to obtain an allicin water-soluble organic solvent layer, and decompressing, rotary steaming and concentrating the allicin water-soluble organic solvent layer to obtain an allicin organic solution; thirdly, adding a fat-soluble organic solvent into the allicin organic solution for extraction, collecting an allicin fat-soluble organic solvent layer, and performing reduced pressure, rotary evaporation and concentration to obtain an allicin organic concentrated solution; and fourthly, performing molecular distillation and collection on the allicin organic concentrated solution to obtain the high-purity allicin.
Example 3: as further optimization of the embodiment, the purity of the alliin is more than or equal to 50 percent, and the activity of the alliinase is more than or equal to 1000U/g.
Example 4: as a further optimization of the above embodiment, the water-soluble organic solvent is one of methanol and ethanol; or/and the fat-soluble organic solvent is one of acetone and diethyl ether.
Example 5: as a further optimization of the above embodiment, the conditions of decompression, rotary evaporation and concentration are that the temperature is 10 ℃ to 50 ℃, the pressure is 0bar to 0.05bar, and the rotating speed is 50rpm to 150 rpm; or/and the temperature during high-speed centrifugation is 4-15 ℃, and the centrifugation speed is 3000-12000 rpm.
Example 6: as a further optimization of the above example, the conditions of the molecular distillation: the sample injection speed is 0.5 ml/min to 5 ml/min, the scraper speed is 5 rpm/min to 50 rpm/min, the external circulation temperature is 10 ℃ to-30 ℃, and the vacuum degree is 1torr to 100 torr.
Example 7: the high-purity allicin is obtained according to the following steps: step one, synthesizing allicin water solution of 4 mg/ml in vitro according to the mass ratio of 1:1.2, at the temperature of 0-10 ℃ and under the environment isolated from air, wherein the purity of alliin is 52.4%, and the activity of allinase is 1200U/g; secondly, adding 95 volume percent ethanol solution into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the ethanol solution of 1:0.8, incubating for 5 min at the temperature of 20 ℃, and then centrifuging at a high speed for 5 min to obtain an allicin ethanol solvent layer, and decompressing, rotatably steaming and concentrating the allicin ethanol solvent layer at the temperature of 40 ℃, the pressure of 0.02bar and the rotation speed of 50rpm to obtain an allicin organic solution, wherein the temperature during high-speed centrifugation is 10 ℃, and the centrifugation rotation speed is 5000 rpm; thirdly, adding an acetone solution into the allicin organic solution according to the volume ratio of the allicin aqueous solution to the acetone solution of 1:0.3 for extraction, collecting an allicin acetone solution layer, and performing reduced pressure, rotary evaporation and concentration under the conditions of the temperature of 40 ℃, the pressure of 0.02bar and the rotating speed of 50rpm to obtain an allicin organic concentrated solution; and fourthly, performing molecular distillation on the allicin organic concentrated solution, and collecting distilled heavy components according to corresponding molecular weights, namely the high-purity allicin, wherein the conditions of the molecular distillation are as follows: the sample introduction speed is 0.5 ml/min, the scraper speed is 12 rpm/min, the external circulation temperature is 10 ℃, and the vacuum degree is 20 torr. The obtained allicin solution had a purity of 95.5%.
Example 8: the high-purity allicin is obtained according to the following steps: step one, synthesizing a 5.5 mg/ml allicin aqueous solution in vitro according to the mass ratio of 1:1 and under the environment of 0-10 ℃ and air isolation, wherein the purity of alliin is 64.3 percent and the activity of alliinase is 5000U/g; secondly, adding a methanol solution into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the methanol solution of 1:1, incubating for 15 min at the temperature of 20 ℃, and then centrifuging at a high speed for 20 min to obtain an allicin methanol solvent layer, and decompressing, rotatably steaming and concentrating the allicin methanol solvent layer under the conditions of the temperature of 30 ℃, the pressure of 0.01bar and the rotation speed of 80rpm to obtain an allicin organic solution, wherein the temperature during high-speed centrifugation is 8 ℃, and the centrifugation rotation speed is 11000 rpm; thirdly, adding an acetone solution into the allicin organic solution according to the volume ratio of the allicin aqueous solution to the ether solution of 1:1 for extraction, collecting an allicin acetone solution layer, and performing reduced pressure, rotary evaporation and concentration under the conditions of the temperature of 30 ℃, the pressure of 0.01bar and the rotating speed of 80rpm to obtain an allicin organic concentrated solution; and fourthly, performing molecular distillation on the allicin organic concentrated solution, and collecting distilled heavy components according to corresponding molecular weights, namely the high-purity allicin, wherein the conditions of the molecular distillation are as follows: the sample introduction speed is 1.2 ml/min, the scraper speed is 15 rpm/min, the external circulation temperature is 5 ℃, and the vacuum degree is 30 torr. The obtained allicin solution had a purity of 95.1%.
Properties of allicin solutions obtained in examples 7 and 8 of the present invention were measured and analyzed
The four-spectrum analysis comprises ultraviolet spectrum, infrared spectrum, mass spectrum and nuclear magnetic resonance spectrum.
The ultraviolet spectrum measuring method comprises the following steps: taking a proper amount of the allicin liquid (allicin) obtained in the embodiments 7 and 8, adding a proper amount of 50-95% ethanol as a solvent to prepare a solution of 5-10 ug/ml, and measuring the solution in the wavelength range of 200-400 nm by 0401 ultraviolet-visible spectrophotometry according to the fourth general rule of Chinese pharmacopoeia (2015 edition). The allicin obtained in example 7 and example 8 showed terminal absorption in the wavelength range of 200-250 nm.
The infrared spectrum determination method comprises the following steps: according to 0402 infrared spectrophotometry in the fourth part of the pharmacopoeia of China (2015 edition), the allicin solution obtained in examples 7 and 8 is scanned by an infrared spectrometer to obtain an infrared absorption spectrum.
The mass spectrometry method comprises the following steps: mass spectrum information of allicin obtained in examples 7 and 8 was collected according to "5. electrospray ionization (ESI)" in 0431 Mass Spectrometry in the fourth Proc. of China (2015 edition) to determine the molecular weight of allicin. The molecular weight of allicin obtained in example 7 and example 8 was 162.78, which is consistent with the value 162.23 reported in the literature.
Nuclear magnetic resonance spectroscopy: according to 0441 NMR spectrometer of the fourth pharmacopoeia of China (2015 edition), a proper amount of the allicin solution obtained in example 7 and example 8 was dissolved in DMSO for co-testing, and the solutions were measured1H-NMR、13C-NMR spectra. The molecular structures of the allicin obtained in example 7 and example 8 are taken to be consistent with the reports in the literature.
The stability of the allicin solution obtained in example 7 and example 8 can be seen through the four-spectrum analysis.
The purity of the allicin solution obtained in example 7 and example 8 was measured by high performance liquid chromatography: referring to the content determination method of allicin in "Galic Powder" collected in European pharmacopoeia 6.0, oxybutylene is used as an internal standard substance, a C18 column (4 x 250 mm, 5 um) and methanol-1% formic acid (60: 40) are used as mobile phases, a detector UV2487 is adopted, the detection wavelength is 254 nm, the flow rate is 0.8 ml/min, the sample injection amount is 20 ul, and the column temperature is 25 ℃. The allicin obtained in example 7 and example 8 has a purity of 95.0% or more.
In conclusion, the preparation process is simple, the raw materials are obtained by natural extraction, and the obtained high-purity allicin serving as a natural medicine has small toxic and side effects and no residue in organisms; the stability and purity of the high-purity allicin are greatly improved, the purity is more than or equal to 95.0 percent, and the safety, high efficiency and quality controllability of the product are realized.
The technical characteristics form an embodiment of the invention, which has strong adaptability and implementation effect, and unnecessary technical characteristics can be increased or decreased according to actual needs to meet the requirements of different situations.
Claims (2)
1. The high-purity allicin is characterized by being obtained according to the following steps: firstly, the purity of alliin is more than or equal to 50 percent, the activity of alliinase is more than or equal to 1000U/g, and the alliin and the alliinase biologically synthesize 1 mg/ml to 10 mg/ml allicin water solution in vitro according to the mass ratio of 1:0.1 to 2 under the environment that the temperature is 0 ℃ to 10 ℃ and is isolated from the air; secondly, adding a water-soluble organic solvent into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the water-soluble organic solvent of 1: 0.5-2, incubating for 5-20 min at the temperature of 15-40 ℃, centrifuging at a high speed of 4-15 ℃ and at a centrifugal speed of 3000-12000 rpm for 5-30 min to obtain an allicin water-soluble organic solvent layer, and decompressing, rotatably steaming and concentrating the allicin water-soluble organic solvent layer to obtain an allicin organic solution; thirdly, adding a fat-soluble organic solvent into the allicin organic solution for extraction, wherein the fat-soluble organic solvent is one of acetone and diethyl ether, collecting an allicin fat-soluble organic solvent layer, and performing reduced pressure, rotary evaporation and concentration to obtain an allicin organic concentrated solution; fourthly, performing molecular distillation and collection on the allicin organic concentrated solution, wherein the conditions of the molecular distillation are as follows: the sample injection speed is 0.5 ml/min to 5 ml/min, the scraper speed is 5 rpm/min to 50 rpm/min, the external circulation temperature is 10 ℃ to-30 ℃, and the vacuum degree is 1torr to 100 torr, thus obtaining the high-purity allicin; wherein, the conditions of decompression, rotary evaporation and concentration are that the temperature is 10 ℃ to 50 ℃, the pressure is 0bar to 0.05bar, and the rotating speed is 50rpm to 150 rpm.
2. A preparation method of high-purity allicin is characterized by comprising the following steps: firstly, the purity of alliin is more than or equal to 50 percent, the activity of alliinase is more than or equal to 1000U/g, and the alliin and the alliinase biologically synthesize 1 mg/ml to 10 mg/ml allicin water solution in vitro according to the mass ratio of 1:0.1 to 2 under the environment that the temperature is 0 ℃ to 10 ℃ and is isolated from the air; secondly, adding a water-soluble organic solvent into the allicin aqueous solution according to the volume ratio of the allicin aqueous solution to the water-soluble organic solvent of 1: 0.5-2, incubating for 5-20 min at the temperature of 15-40 ℃, centrifuging at a high speed of 4-15 ℃ and at a centrifugal speed of 3000-12000 rpm for 5-30 min to obtain an allicin water-soluble organic solvent layer, and decompressing, rotatably steaming and concentrating the allicin water-soluble organic solvent layer to obtain an allicin organic solution; thirdly, adding a fat-soluble organic solvent into the allicin organic solution for extraction, wherein the fat-soluble organic solvent is one of acetone and diethyl ether, collecting an allicin fat-soluble organic solvent layer, and performing reduced pressure, rotary evaporation and concentration to obtain an allicin organic concentrated solution; fourthly, performing molecular distillation and collection on the allicin organic concentrated solution, wherein the conditions of the molecular distillation are as follows: the sample injection speed is 0.5 ml/min to 5 ml/min, the scraper speed is 5 rpm/min to 50 rpm/min, the external circulation temperature is 10 ℃ to-30 ℃, and the vacuum degree is 1torr to 100 torr, thus obtaining the high-purity allicin; wherein, the conditions of decompression, rotary evaporation and concentration are that the temperature is 10 ℃ to 50 ℃, the pressure is 0bar to 0.05bar, and the rotating speed is 50rpm to 150 rpm.
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