CN114349696A - 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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- CN114349696A CN114349696A CN202210018743.6A CN202210018743A CN114349696A CN 114349696 A CN114349696 A CN 114349696A CN 202210018743 A CN202210018743 A CN 202210018743A CN 114349696 A CN114349696 A CN 114349696A
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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 commercially available perchloric acid, completely dissolving the lotus plumule alkali powder, adding a proper amount of purified water to dilute the lotus plumule alkali powder to reach the mass concentration of 1-40% of perchloric acid, adding a proper amount of water-saturated dichloromethane to extract the lotus plumule alkali powder for 1-3 times, combining the dichloromethane, and recovering, concentrating and drying the mixture to obtain the lotus plumule total alkali perchlorate. The existing alkaloid salt forming process adopts a method of firstly forming salt in an organic solvent and then crystallizing, but the crystallization time is long and the yield is low. 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 preparation technology of salifying traditional Chinese medicine alkaloids, and particularly relates to a method for preparing and purifying lotus plumule total alkaloid perchlorate from lotus plumule total alkaloids (hereinafter referred to as lotus plumule total alkaloid).
Background
The lotus plumule is dry young leaves and radicles of mature seeds of a lotus (Nelumbo nucifera Gaertn) belonging to Nymphaeaceae, is a variety collected in the Chinese pharmacopoeia of the calendar edition, has bitter and cold properties, enters heart, lung and kidney meridians, and has the effects of clearing away heart-fire, removing heat, securing essence and stopping bleeding. The traditional Chinese medicine is used for treating syndromes of heat entering pericardium, disharmony between heart and kidney, insomnia, spermatorrhea, hematemesis and the like.
The plumula Nelumbinis total alkaloid is the main active ingredient of plumula Nelumbinis, including liensinine, isoliensinine and neferine, and has wide biological activities of lowering blood pressure, resisting arrhythmia, resisting platelet aggregation, resisting cancer, etc. However, these alkaloid components are insoluble in water and thus limit the biological activity. Because of poor water solubility and low bioavailability, the effective concentration can not be reached, and the cell experiment, animal experiment and clinical curative effect are influenced.
The alkaloid reacts with acid to generate salt, which can improve the water solubility. Patent (CN 200510032062.1) discloses macleaya cordata total alkaloid salt and a preparation method thereof: dissolving macleaya cordata total alkali in a polar or medium polar solvent such as methanol, ethanol, acetone, ethyl acetate, chloroform and the like, dissolving an organic acid in a corresponding polar or medium polar solvent such as methanol, ethanol, acetone, ethyl acetate, chloroform and the like, mixing the two solvents under stirring, and monitoring the complete reaction of sanguinarine and chelerythrine by a thin layer, wherein the organic acid involved in the method comprises salicylic acid, benzoic acid, tartaric acid and maleic acid (see claim 4); the preparation method of macleaya cordata total alkali borate comprises 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). The patent (CN 200810209548.1) discloses a preparation method of total alkaloid salt of corydalis tuber: adding 1-5 times of water into the corydalis tuber total alkaloids, stirring uniformly, adding 5-30% of acid (acetic acid, nitric acid or hydrochloric acid, see claim 7) in weight percentage concentration, carrying out salt forming reaction, heating the salt forming reaction solution to the pH value of 1-4, heating to the temperature of 60-90 ℃, preserving heat for 30-60 min, cooling to room temperature, filtering and concentrating the reaction solution, and drying to obtain the corydalis tuber total alkaloids salt (see claim 1). Also, patent (CN 98121706.0) discloses a salt intermediate obtained by extracting and purifying isoliensinine and liensinine from plumula Nelumbinis, adjusting alkali with sodium hydroxide, adjusting acid with hydrochloric acid, extracting with chloroform and diethyl ether, and recrystallizing. The salifying process of the alkaloid is summarized as follows: the alkaloid is firstly dissolved in organic solvents such as methanol and the like, then acid is added to react with the alkaloid to form salt, and then salt is separated out by a crystallization method, or the solvent is recycled to directly obtain the salt.
However, the above methods are not suitable for the preparation and purification of the lotus nut total alkali perchlorate. After the lotus nut total alkali reacts with perchloric acid to form salt, the lotus nut total alkali is very soluble in reaction liquid and difficult to crystallize, and no crystal is separated out even if the lotus nut total alkali is placed in a refrigerator at 4 ℃ for several days; if reduced pressure concentration and drying are adopted, perchloric acid with the boiling point as high as 203 ℃ is difficult to recover, and residual reactants and byproducts are difficult to remove.
Disclosure of Invention
The invention provides a simple and efficient method for preparing and purifying the perchlorate of the lotus plumule total alkaloid on the basis of preparing the total alkaloid from the lotus plumule in the earlier invention (ZL 201310344643.3), and the method is realized by the following technical scheme.
A preparation and purification method of lotus nut total alkali perchlorate is characterized by taking 1 part of lotus nut total alkali powder, adding a proper amount of commercially available perchloric acid, completely dissolving the lotus nut total alkali powder, adding a proper amount of purified water to dilute the lotus nut total alkali powder until the mass concentration of the perchloric acid is 1-40% (detailed in an attached drawing 1), adding a proper amount of water-saturated dichloromethane to extract the lotus nut total alkali perchlorate 1-3 times (detailed in an attached drawing 2), combining the dichloromethane, recovering, concentrating and drying the dichloromethane to obtain the lotus nut total alkali perchlorate.
The lotus nut total alkaloid powder is characterized in that the lotus nut total alkaloid powder is obtained by extracting and separating lotus nuts or purchased in the market, and the total alkaloid content is not less than 50 percent calculated by the sum of liensinine, isoliensinine and neferine.
The method is characterized in that the dissolving speed and the dissolving degree of the lotus nut total alkali powder are increased by adopting methods such as ultrasound, stirring, vortex, heating and the like.
The complete dissolution described above, characterized in that the following salification reactions occur:
⑴ C37H42N2O6 (liensinine) + HClO4＝C37H42N2O6·HClO4 (Lotus plumule alkali perchlorate)
⑵ C37H42N2O6(isoliensinine) + HClO4＝C37H42N2O6·HClO4(Isoliensinine perchlorate)
⑶ C38H44N2O6(Meliensinine) + HClO4＝C38H44N2O6·HClO4 (Methylenterine perchlorate).
The mass concentration of the diluted perchloric acid is 1-40%, and the diluted perchloric acid is characterized in that the preferable concentration is 5-30%, and the optimal concentration is 10%.
The dichloromethane with proper amount is characterized in that the dichloromethane with proper amount is 0.25-3 times of the total volume after being diluted by water (see figure 3 in detail), the preferable volume is 1-2 times, and the optimal volume is 1.5 times.
The lotus nut total alkali perchlorate is characterized in that an electrospray mass spectrogram ESI-MS (ESI-MS)m/z) At least 611, 625[ M + H ]]+And 711, 725[ M + HClO4]+(M610, 625) (see figure 4 for details).
Advantageous effects
The present invention has at least the following advantages over the prior art solutions, but not limited to the following.
1. The invention provides a novel method for preparing lotus nut total alkali perchlorate from lotus nut total alkali, and fills the blank of products of the lotus nut total alkali perchlorate.
2. The solubility of the lotus nut total alkali perchlorate prepared by the invention in water at 25 ℃ is 2.433 mg/mL, which is 8.72 times of the lotus nut total alkali solubility of 0.279 mg/mL, and the solubility is greatly improved.
3. The invention selects dichloromethane to extract the lotus nut total alkali perchlorate, because the extraction effect of the dichloromethane is far higher than that of trichloromethane and tetrachloromethane, and the result is shown in table 1.
TABLE 1 extraction Effect of different solvents
| Kind of solvent | Methylene dichloride | Trichloromethane | Tetrachloromethane |
| Peak area | 574.2 | 81.3 | 0 |
4. After reacting the lotus nut total alkali with commercially available perchloric acid to form salt, if dichloromethane is directly used for extraction, the perchlorate of the lotus nut total alkali can hardly be extracted; before extraction, a proper amount of purified water is added to dilute the perchloric acid until the mass concentration of the perchloric acid is 1-40%, and then dichloromethane is used for extraction, so that the extraction effect is greatly improved (see the attached figure 1 for details).
Chromatographic conditions
Agilent 1260 high performance liquid chromatograph (Agilent Corp., USA).
Eclipe XDB C-18 column (4.5 mm. times.150 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 amount of 10 uL, column temperature of 30 ℃. The HPLC chromatogram is shown in figure 5.
Conditions of Mass Spectrometry
A micOTOF-QII mass spectrometer (Bruker, Germany).
Electrospray ion source (ESI), positive ion mode, capillary voltage 4000V, taper hole voltage-500V, atomization gas pressure 2 bar, drying gas flow rate 4L/min, drying gas temperature 180 ℃, scanning range m/z: 50 to 2000. ESI-MS mass spectrum is shown in figure 4.
Drawings
FIG. 1 shows the relationship between the mass concentration of perchloric acid and the extraction yield.
FIG. 2 shows the relationship between the number of extractions and the extraction rate.
FIG. 3 shows the relationship between the volume multiple of methylene chloride and the extraction rate.
FIG. 4 shows the ESI-MS mass spectrum of lotus nut total alkali perchlorate.
FIG. 5 HPLC chromatogram of total alkali perchlorate of plumula Nelumbinis.
Detailed Description
The technical solutions of the present invention are described in detail below by way of examples, and the following examples are only for explaining and illustrating the technical solutions of the present invention, and are not intended to limit the technical solutions 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 commercially available perchloric acid is added to be completely dissolved, a proper amount of purified water is added to be diluted until the mass concentration of the perchloric acid is 10%, 1.5 times of water-saturated dichloromethane is added to extract for 2 times, the 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 commercially available perchloric acid is added to be completely dissolved, a proper amount of purified water is added to be diluted until the mass concentration of the perchloric acid is 1%, dichloromethane saturated by 3 times of water is added for extraction for 1 time, the 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 commercially available perchloric acid is added to be completely dissolved, a proper amount of purified water is added to be diluted until the mass concentration of the perchloric acid is 40%, dichloromethane saturated by 0.25 volume of water is added to be extracted for 3 times, the dichloromethane is combined, and the lotus plumule total alkali perchlorate 3 is obtained after recovery, concentration and drying.
Claims (7)
1. A preparation and purification method of lotus plumule total alkali perchlorate is characterized by taking 1 part of lotus plumule total alkali powder, adding a proper amount of commercially available perchloric acid to completely dissolve the lotus plumule total alkali perchlorate, then adding a proper amount of purified water to dilute the lotus plumule total alkali powder until the mass concentration of the perchloric acid is 1% -40%, adding a proper amount of water-saturated dichloromethane to extract the lotus plumule total alkali perchlorate for 1-3 times, combining the dichloromethane, recovering, concentrating and drying the mixture to obtain the lotus plumule total alkali perchlorate.
2. The lotus nut total alkaloid powder according to claim 1, wherein the total alkaloid content of the lotus nut total alkaloid powder obtained by extraction and separation from lotus nut or purchased from the market is not less than 50% in terms of the sum of lotus nut alkaloid, isoliensinine and neferine.
3. The method for dissolving lotus plumule total alkali powder completely as set forth in claim 1, wherein the dissolving speed and degree of lotus plumule total alkali powder are increased by ultrasonic, stirring, vortex, heating, etc.
4. Complete dissolution according to claim 1, characterised in that the following salification reactions occur:
⑴ C37H42N2O6 (liensinine) + HClO4＝C37H42N2O6·HClO4 (Lotus plumule alkali perchlorate)
⑵ C37H42N2O6(isoliensinine) + HClO4＝C37H42N2O6·HClO4(Isoliensinine perchlorate)
⑶ C38H44N2O6(Meliensinine) + HClO4＝C38H44N2O6·HClO4 (Methylenterine perchlorate).
5. The diluted perchloric acid as claimed in claim 1, having a mass concentration of 1% to 40%, is characterized by a concentration of 5% to 30%, preferably 10%.
6. The method of claim 1, wherein the amount of dichloromethane added is 0.25-3 times, preferably 1-2 times, and most preferably 1.5 times the total volume of the diluted solution.
7. The lotus nut total alkali perchlorate as in claim 1, which is characterized in that an electrospray mass spectrum ESI-MS (ESI-MS)m/z) At least 611, 625[ M + H ]]+And 711, 725[ M + HClO4]+Ion peaks of (M ═ 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 |
-
2022
- 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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