CN114349696B - Preparation and purification method of lotus nut total alkali perchlorate - Google Patents
Preparation and purification method of lotus nut total alkali perchlorate Download PDFInfo
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- CN114349696B CN114349696B CN202210018743.6A CN202210018743A CN114349696B CN 114349696 B CN114349696 B CN 114349696B CN 202210018743 A CN202210018743 A CN 202210018743A CN 114349696 B CN114349696 B CN 114349696B
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Abstract
The invention relates to a method for preparing and purifying lotus nut total alkali perchlorate from lotus nut total alkali. The specific operation steps are as follows: taking 1 part of lotus plumule alkali powder, adding a proper amount of commercial perchloric acid, completely dissolving, adding a proper amount of purified water to dilute to the perchloric acid with the mass concentration of 1-40%, adding a proper amount of water-saturated dichloromethane to extract for 1-3 times, combining the dichloromethane, recovering, concentrating and drying to obtain the lotus plumule total alkali perchlorate. The existing alkaloid salification process usually adopts a method of salifying in an organic solvent and crystallizing, but has long crystallization time and low yield. Compared with the prior art, the method for preparing and purifying the lotus nut total alkali perchlorate is simpler and more efficient, and is suitable for industrial mass production.
Description
Technical Field
The invention belongs to a traditional Chinese medicine alkaloid salifying preparation technology, and particularly relates to a method for preparing and purifying lotus plumule total alkaloids (hereinafter referred to as lotus plumule total alkaloids).
Background
The lotus plumule is the dried young leaves and radicle of the mature seed of lotus (Nelumbo nucifera Gaertn) which is the species received in the Chinese pharmacopoeia of calendar, has bitter and cold nature, enters heart, lung and kidney channels, and has the effects of clearing heart and removing heat, securing essence and stopping bleeding. The Chinese medicine is used for treating the symptoms of heat entering the pericardium, heart-kidney disharmony, insomnia, spermatorrhea, blood heat hematemesis and the like.
The plumula Nelumbinis total alkaloids are main active ingredients in plumula Nelumbinis, including plumula Nelumbinis alkali, isoliensinine, plumula Nelumbinis alkali, etc., and have wide biological activities of lowering blood pressure, resisting arrhythmia, resisting platelet aggregation, resisting cancer, etc. However, these alkaloid components are insoluble in water and limit their exertion of biological activity. Because of poor water solubility and low bioavailability, the effective concentration can not be achieved, and the cell experiment, animal experiment and even clinical curative effect can be influenced.
The alkaloid reacts with acid to form salt, which can improve the water solubility. Patent (CN 200510032062.1) discloses a macleaya cordata total alkaloid salt and a preparation method thereof: dissolving macleaya cordata total alkali in polar or medium polar solvents such as methanol, ethanol, acetone, ethyl acetate, chloroform and the like, dissolving organic acid in corresponding polar or medium polar solvents such as methanol, ethanol, acetone, ethyl acetate, chloroform and the like, mixing the solvents under stirring, and carrying out thin-layer monitoring on the complete reaction of sanguinarine and chelerythrine, wherein the organic acid involved in the method comprises salicylic acid, benzoic acid, tartaric acid and maleic acid (see claim 4); preparing macleaya cordata total alkali borate, dissolving macleaya cordata total alkaloids in methanol or ethanol, adding quantitative saturated boric acid solution into the solution, and collecting precipitate to obtain macleaya cordata total alkali borate (see claim 6). Patent (CN 200810209548.1) discloses a preparation method of total alkaloid salt of rhizoma corydalis: adding 1-5 times of water into the total alkaloids of rhizoma corydalis, stirring uniformly, adding 5-30% acid (acetic acid, nitric acid or hydrochloric acid, see claim 7) for salifying, heating to 60-90 ℃ for 30-60 min, cooling to room temperature, filtering and concentrating the reaction solution, and drying to obtain the total alkaloids salt of rhizoma corydalis (see claim 1). Also patent (CN 98121706.0) discloses the preparation of salt intermediates by the methods of caustic soda conditioning, hydrochloric acid conditioning, chloroform, diethyl ether extraction, recrystallization, etc. when isoliensinine and liensinine are extracted and purified from plumula Nelumbinis. The alkaloid salification process is summarized as follows: dissolving alkaloid in organic solvent such as methanol, adding acid to react with the alkaloid to form salt, and crystallizing to separate out salt or recovering solvent to obtain salt directly.
However, none of the above methods are suitable for the preparation and purification of lotus plumule total alkali perchlorate. Because the lotus plumule total alkali is very easy to dissolve in the reaction liquid and is difficult to crystallize after being salified by the reaction with perchloric acid, no crystallization is separated out even if the lotus plumule total alkali is placed in a refrigerator at the temperature of 4 ℃ for a plurality of days; if the concentration and drying are carried out under reduced pressure, the perchloric acid with the boiling point as high as 203 ℃ is difficult to recycle, and the residual reactants and byproducts are difficult to remove.
Disclosure of Invention
The invention provides a simple and efficient method for preparing and purifying lotus plumule total alkali perchlorate based on the preparation of total alkaloids from lotus plumule by the pre-invention (ZL 201310344643.3), which is realized by the following technical scheme.
A process for preparing and purifying the perchlorate of lotus seed total alkali includes such steps as preparing 1 part of lotus seed total alkali powder, adding commercial perchloric acid, dissolving, diluting with purified water to 1-40% of perchloric acid, extracting with water-saturated dichloromethane for 1-3 times, mixing dichloromethane, recovering, concentrating and drying.
The lotus plumule total alkali powder is characterized in that the total alkali content is not less than 50% calculated by the sum of lotus plumule alkali, isoliensinine and methyl lotus plumule alkali, and is obtained by extraction and separation from lotus plumule or purchased in the market.
The method is characterized in that the dissolution speed and the dissolution degree of the lotus plumule total alkali powder are increased by adopting methods such as ultrasonic, stirring, vortex, heating and the like.
The complete dissolution described above is characterized in that the following salification reactions occur:
⑴ C 37 H 42 N 2 O 6 (liensinine) +HClO 4 ＝C 37 H 42 N 2 O 6 ·HClO 4 (lotus plumule alkali perchlorate)
⑵ C 37 H 42 N 2 O 6 (isoliensinine) +HClO 4 ＝C 37 H 42 N 2 O 6 ·HClO 4 (Isomelanin perchlorate)
⑶ C 38 H 44 N 2 O 6 (methyl lotus plumule) +HClO 4 ＝C 38 H 44 N 2 O 6 ·HClO 4 (methyl lotus plumule perchlorate).
The concentration of the perchloric acid diluted to 1-40% by mass is characterized in that the optimal concentration is 5-30% and the optimal concentration is 10%.
The above-mentioned proper quantity of dichloromethane is characterized by that its total volume is 0.25-3 times of proper quantity (see figure 3), preferably 1-2 times of volume and most preferably 1.5 times of volume after dilution by adding water.
The lotus plumule total alkali perchlorate is characterized in that the lotus plumule total alkali perchlorate is prepared by an electrospray mass spectrum ESI-MS%m/z) At least 611, 625[ M+H ]] + And 711, 725[ M+HClO 4 ] + Ion peaks (m=610, 610, 625) (see fig. 4 for details).
Advantageous effects
The present invention has at least, but not limited to, the following advantages over prior art solutions.
1. The invention provides a novel method for preparing lotus nut total alkali perchlorate from lotus nut total alkali, and fills the blank of the lotus nut total alkali perchlorate product.
2. The solubility of the lotus plumule total alkali perchlorate prepared by the method in water at 25 ℃ is 2.433 mg/mL, which is 8.72 times of the solubility of the lotus plumule total alkali at 0.279 mg/mL, and the solubility is greatly improved.
3. The invention selects dichloromethane to extract lotus plumule total alkali perchlorate because the extraction effect of dichloromethane is far higher than that of trichloromethane and tetrachloromethane, and the results are shown in table 1.
TABLE 1 extraction Effect of different solvents
| Solvent species | Dichloromethane (dichloromethane) | Trichloromethane | Tetrachloromethane |
| Peak area | 574.2 | 81.3 | 0 |
4. After the lotus plumule total alkali reacts with commercial perchloric acid to form salt, if dichloromethane is directly used for extraction, the lotus plumule total alkali perchlorate is hardly extracted; before extraction, the invention adds a proper amount of purified water to dilute to 1% -40% of perchloric acid mass concentration, and then uses dichloromethane to extract, thus greatly improving the extraction effect (see figure 1 for details).
Chromatographic conditions
Agilent 1260 high performance liquid chromatograph (Agilent Co., U.S.A.).
Eclipse XDB C-18 column (4.5 mm X150 mm,5 μm), mobile phase: acetonitrile-0.1% triethylamine aqueous solution (55:45), isocratic elution, flow rate of 1 mL/mL, ultraviolet detection wavelength of 282 nm, sample injection amount of 10 μl, and column temperature of 30 ℃. HPLC chromatograms are shown in FIG. 5.
Mass spectrometry conditions
micr-OTOF-QII Mass Spectrometry (Bruker, germany).
Electrospray ion source (ESI), positive ion mode, capillary voltage 4000V, cone voltage-500V, atomizing gas pressure 2 bar, drying gas flow rate 4L/min, drying gas temperature 180 ℃, scanning range m/z: 50-2000. The ESI-MS mass spectrum is shown in figure 4.
Drawings
FIG. 1 shows the relationship between the perchloric acid mass concentration and the extraction rate.
FIG. 2 is a graph showing the relationship between the number of extractions and the extraction rate.
FIG. 3 is a graph showing the relationship between the volume multiple of methylene chloride and the extraction yield.
FIG. 4 shows ESI-MS mass spectrum of total alkali perchlorate of lotus plumule.
FIG. 5 HPLC chromatogram of lotus plumule total alkali perchlorate.
Detailed Description
The following examples are given to illustrate and describe the technical solution of the present invention in detail, but are not to be construed as limiting the technical solution of the present invention.
Example 1
A preparation and purification method of lotus plumule total alkali perchlorate is characterized in that 1 part of lotus plumule total alkali powder is taken, a proper amount of commercial perchloric acid is added to dissolve the lotus plumule total alkali perchlorate completely, then a proper amount of purified water is added to dilute the lotus plumule total alkali perchlorate until the perchloric acid mass concentration is 10%, 1.5 times of water-saturated dichloromethane is added to extract the lotus plumule total alkali perchlorate for 2 times, dichloromethane is combined, and the lotus plumule total alkali perchlorate 1 is obtained after recovery, concentration and drying.
Example 2
A preparation and purification method of lotus plumule total alkali perchlorate is characterized in that 1 part of lotus plumule total alkali powder is taken, a proper amount of commercial perchloric acid is added to dissolve the lotus plumule total alkali perchlorate completely, then a proper amount of purified water is added to dilute the lotus plumule total alkali perchlorate to 1% by mass concentration, 3 times of water-saturated dichloromethane is added to extract for 1 time, dichloromethane is combined, and the lotus plumule total alkali perchlorate 2 is obtained after recovery, concentration and drying.
Example 3
A preparation and purification method of lotus plumule total alkali perchlorate is characterized in that 1 part of lotus plumule total alkali powder is taken, a proper amount of commercial perchloric acid is added to dissolve the lotus plumule total alkali perchlorate completely, then a proper amount of purified water is added to dilute the lotus plumule total alkali perchlorate until the perchloric acid mass concentration is 40%, dichloromethane saturated by 0.25 times of volume of water is added to extract the lotus plumule total alkali perchlorate 3 for 3 times, dichloromethane is combined, and the lotus plumule total alkali perchlorate 3 is obtained after recovery, concentration and drying.
Claims (9)
1. A preparation and purification method of lotus plumule total alkali perchlorate is characterized in that 1 part of lotus plumule total alkali powder is taken, a proper amount of commercial perchloric acid is added to dissolve the lotus plumule total alkali perchlorate completely, then a proper amount of purified water is added to dilute the lotus plumule total alkali perchlorate until the perchloric acid mass concentration is 1-40%, a proper amount of water-saturated dichloromethane is added to extract the lotus plumule total alkali perchlorate for 1-3 times, dichloromethane is combined, and the lotus plumule total alkali perchlorate is obtained after recovery, concentration and drying; wherein the total alkali powder of plumula Nelumbinis is obtained by extracting and separating plumula Nelumbinis or purchased in market, and the total alkali content is not less than 50% based on the sum of plumula Nelumbinis alkali, isoliensinine and methyl plumula Nelumbinis alkali.
2. The method for preparing and purifying the lotus seed total alkali perchlorate as claimed in claim 1, wherein the method for completely dissolving the perchlorate is characterized in that the method for dissolving the perchlorate by ultrasonic, stirring, vortex or heating is adopted to increase the dissolution rate and degree of the lotus seed total alkali powder.
3. The method for preparing and purifying the lotus plumule alkali perchlorate as claimed in claim 1, wherein the following salification reaction occurs in complete dissolution:
⑴ C 37 H 42 N 2 O 6 (liensinine) +HClO 4 ＝C 37 H 42 N 2 O 6 ·HClO 4 (liensinine perchlorate);
⑵ C 37 H 42 N 2 O 6 (isoliensinine) +HClO 4 ＝C 37 H 42 N 2 O 6 ·HClO 4 (isoliensinine perchlorate);
⑶ C 38 H 44 N 2 O 6 (methyl lotus plumule) +HClO 4 ＝C 38 H 44 N 2 O 6 ·HClO 4 (methyl lotus plumule perchlorate).
4. The method for preparing and purifying total alkaloids perchlorate of lotus plumule according to claim 1, which is characterized by dilution to a perchloric acid mass concentration of 5% -30%.
5. The method for preparing and purifying total alkaloids perchlorate of lotus seed according to claim 1, wherein the total alkaloids perchlorate is diluted to a concentration of 10% by mass of perchloric acid.
6. The method for preparing and purifying total alkaloids perchlorate of lotus seed according to claim 1, wherein the volume of saturated dichloromethane added with a proper amount of water is 0.25-3 times.
7. The method for preparing and purifying total alkaloids perchlorate of lotus seed according to claim 1, wherein the volume of saturated dichloromethane added with a proper amount of water is 1-2 times.
8. The method for preparing and purifying total alkaloids perchlorate of lotus seed according to claim 1, wherein the volume of saturated dichloromethane added with a proper amount of water is 1.5 times.
9. The method for preparing and purifying the lotus nut total alkali perchlorate as claimed in claim 1, which is characterized in that the lotus nut total alkali perchlorate electrospray mass spectrum ESI-MS @m/z) At least 611, 625[ M+H ]] + And 711, 725[ M+HClO 4 ] + Ion peaks of (m=610, 610, 624).
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB968042A (en) * | 1962-02-02 | 1964-08-26 | Vsesoiuzny Nii Lekarstvenykh I | An alkaloid (c h o n) and a method of extracting it from plant material |
| GB1172777A (en) * | 1967-08-11 | 1969-12-03 | Vsesjuzny Nii Lekarstvennykh R | A Method of Producing an Alkaloid Preparation. |
| CN1257070A (en) * | 1998-12-14 | 2000-06-21 | 同济医科大学 | Process for extracting purified isoliensinine and liensinine from plumula nelumbinis |
| CN101791335A (en) * | 2010-04-08 | 2010-08-04 | 江西民康制药有限公司 | Total alkaloid mixture sourcing from Chinese medicina plant lotus plumule and extraction and preparation method thereof |
| CN106924258A (en) * | 2017-01-11 | 2017-07-07 | 中南民族大学 | Liensinine, isoliensinine and neferine prepare the purposes of GLUT4 accelerative activators |
-
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- 2022-01-09 CN CN202210018743.6A patent/CN114349696B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB968042A (en) * | 1962-02-02 | 1964-08-26 | Vsesoiuzny Nii Lekarstvenykh I | An alkaloid (c h o n) and a method of extracting it from plant material |
| GB1172777A (en) * | 1967-08-11 | 1969-12-03 | Vsesjuzny Nii Lekarstvennykh R | A Method of Producing an Alkaloid Preparation. |
| CN1257070A (en) * | 1998-12-14 | 2000-06-21 | 同济医科大学 | Process for extracting purified isoliensinine and liensinine from plumula nelumbinis |
| CN101791335A (en) * | 2010-04-08 | 2010-08-04 | 江西民康制药有限公司 | Total alkaloid mixture sourcing from Chinese medicina plant lotus plumule and extraction and preparation method thereof |
| CN106924258A (en) * | 2017-01-11 | 2017-07-07 | 中南民族大学 | Liensinine, isoliensinine and neferine prepare the purposes of GLUT4 accelerative activators |
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