CN112341515A - Method for extracting taraxasterol from sow thistle - Google Patents
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Abstract
The invention provides a method for extracting taraxasterol from sow thistle, which comprises the steps of cleaning and drying sow thistle leaves, then crushing the sow thistle leaves, adding methanol to obtain a mixed system A, carrying out reflux heating treatment on the mixed system A at 80-85 ℃, carrying out rotary evaporation on a filtrate obtained after filtering, carrying out heat treatment on an obtained concentrate at 80-85 ℃, adding purified water or a sodium hydroxide solution with the mass fraction of 1-5%, then extracting with diethyl ether to obtain an extract, removing the diethyl ether in the extract, and drying to obtain crude taraxasterol; the crude taraxasterol is sequentially purified by acetone and ethanol, and then dried to obtain the taraxasterol, the extraction time is short, the extraction efficiency is high, the extracted taraxasterol can be applied to food and medicines, the sow thistle can be reasonably utilized, and the processing of the taraxasterol also promotes the development of local economy; the bitter herbs are collected and extracted for deep processing, so that the waste is changed into valuable, and the resources of the bitter herbs can be reasonably utilized.
Description
Technical Field
The invention belongs to the technical field of natural product extraction, and particularly relates to a method for extracting taraxasterol from sow thistle.
Background
The taraxasterol is a natural product which is extracted from taraxacum and has strong physiological activity, pharmacological activity and biological activity. Taraxasterol is a triterpenoid monomer, has various pharmacological activities such as anti-inflammatory activity, oxidation resistance, cancer resistance and the like, and has been reported in various documents at present, particularly the pharmacological activity and the pharmacological action mechanism of the compound. In the research, an anti-HBV replication inhibition experiment is carried out on taraxasterol at a cell level, whether viruses are inhibited or not is detected, the taraxasterol is found to be capable of inhibiting HBV surface antigen (HBsAg) and E antigen (HBeAg) from being secreted into a supernatant and inhibiting replication of HBVDNA, and then the taraxasterol is detected to be capable of reducing PTB expression. The result shows that the taraxasterol can be used as a lead compound for further structure optimization to prepare a preparation or a medicine with anti-HBV activity. The taraxasterol has strong antiviral activity, can inhibit cell from secreting HBsAg and HBeAg and can inhibit replication of HBVDNA, and has the function of targeting PTB protein.
The sow thistle is widely available in most areas, and the sow thistle contains taraxasterol, but the value of the sow thistle only reflects the edible value of the sow thistle at present, and the medicinal value and the economic value of the sow thistle are rarely developed.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a method for extracting taraxasterol from sow thistle, the extraction time is short, the extraction efficiency is high, and the extracted taraxasterol can be applied to foods and medicines.
The invention is realized by the following technical scheme:
a method for extracting taraxasterol from sow thistle comprises the following steps:
step 1, cleaning and drying sow thistle leaves, then crushing the sow thistle leaves, adding methanol to obtain a mixed system A, and carrying out reflux heating treatment on the mixed system A at the temperature of 80-85 ℃ to obtain a reaction solution;
step 2, filtering the reaction solution to obtain filtrate, performing rotary evaporation on the filtrate, and performing heat treatment on the obtained concentrate at the temperature of 80-85 ℃ to obtain sow thistle extractum;
step 3, adding purified water or a sodium hydroxide solution with the mass fraction of 1-5% into the sow thistle extract, extracting with diethyl ether to obtain an extract, removing the diethyl ether in the extract, and drying to obtain crude taraxasterol;
and 4, sequentially purifying the crude taraxasterol by using acetone and ethanol, and drying to obtain the taraxasterol.
Preferably, in the step 1, the cleaned bitter leaves are dried at 40-60 ℃ for 4-8 h, and the stirring is carried out once every 0.5-1 h during the drying period.
Preferably, in the step 1, the crushed sow thistle leaves are screened by a 40-60-mesh screen and then added with methanol.
Preferably, the mass of the methanol added in the step 1 is 10 times of that of the crushed bitter leaves.
Preferably, in the step 1, the mixed system A is refluxed and heated at the temperature for 4-5 hours to obtain a reaction solution.
Preferably, in the step 1, the crushed sow thistle leaves are divided into 2-3 parts and subjected to the reflux heating treatment, and then the corresponding obtained liquids are combined to obtain a reaction solution.
Preferably, in the step 2, the concentrate is subjected to heat treatment at the temperature for 5-10 min to obtain the sow thistle extract.
Preferably, the ether in the extraction liquid is removed in the step 3, and then the extraction liquid is dried in vacuum at the temperature of-8-0 ℃.
Preferably, in the step 4, acetone is added into the crude taraxasterol, the mixture is heated and dissolved, then the temperature is naturally reduced for crystallization, the mixture is filtered and collected, and then the mixture is recrystallized for 3 to 5 times by using ethanol, and finally the drying is carried out.
Preferably, in the step 4, the purified crude taraxasterol is subjected to vacuum drying at-8 to 0 ℃ to obtain the taraxasterol.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention relates to a method for extracting taraxasterol from sow thistle, which comprises the steps of cleaning, drying and crushing sow thistle leaves, carrying out reflux heating treatment by using methanol to transfer the taraxasterol in the sow thistle into the methanol, removing the methanol, sequentially extracting by using purified water or sodium hydroxide solution with the mass fraction of 1-5% and diethyl ether to obtain crude taraxasterol, purifying by using acetone and ethanol, and finally drying to obtain the taraxasterol. The method not only develops the medicinal value and the economic value of the sow thistle, but also enriches the extraction method of taraxasterol, and the extraction method is applied to the northern area of Shaanxi province in China with more sow thistle, so that the local sow thistle can be reasonably utilized, and the processing of the local sow thistle also promotes the development of local economy; the bitter herbs are collected and extracted for deep processing, so that the waste is changed into valuable, and the resources of the bitter herbs can be reasonably utilized.
Drawings
FIG. 1 is a flow chart of the method of the present invention.
FIG. 2 is a structural formula of taraxasterol.
Detailed Description
The present invention will now be described in further detail with reference to specific examples, which are intended to be illustrative, but not limiting, of the invention.
The invention relates to a method for extracting taraxasterol from sow thistle, which comprises the following steps as shown in figure 1:
firstly, crude extraction, namely reflux extraction;
(1) cleaning and drying fresh sow thistle leaves, weighing 1000g of crushed samples, screening by a 40-60-mesh sieve, and placing in a round-bottom flask;
specifically, the bitter herb leaves are washed by deionized water for 3-4 times, and the washed bitter herb leaves are dried by a constant-temperature air-blowing drying oven at the drying temperature of 40-60 ℃ for 4-8 hours while being stirred every 0.5-1 hour during drying; preventing the bitter herbs from being scorched due to uneven heating;
(2) adding 10 times of methanol by mass for soaking, carrying out reflux heating on a water bath at the temperature of 80-85 ℃ for 4-5 h, dividing the sample into 2-3 parts and carrying out reflux heating at the same time during actual operation, combining reaction liquid and filtering to obtain filtrate;
(3) recycling most of methanol from the filtrate by a rotary evaporator to obtain a concentrate;
(4) treating the concentrate in a water bath at 80-85 ℃ for 5-10 min to volatilize residual methanol to obtain sow thistle extract;
(5) adding 1000mL of purified water or 1000mL of sodium hydroxide solution with the mass fraction of 1% -5% into the sow thistle extract to dilute the sow thistle extract, and transferring the sow thistle extract into a separating funnel;
(6) adding 1000mL of ether for extraction, vibrating for 5-6 minutes, standing for layering, removing ether insoluble substances, continuously extracting for 5-6 times, and combining ether extract;
(7) and (3) placing the extract liquor on a rotary evaporator, recovering all ether, and drying the residue at a low temperature of-8-0 ℃ in vacuum to obtain a yellow paste, namely the crude taraxasterol.
Secondly, purifying crude taraxasterol
Adding 500mL of acetone into crude taraxasterol, heating for dissolving, naturally cooling for crystallization, separating out white crystals which are further purified taraxasterol crude products, filtering while the crude products are cold, collecting, recrystallizing for 3-5 times by using 500mL of ethanol, drying in vacuum at the low temperature of-8-0 ℃ to obtain white or colorless powdery substances which are taraxasterol, weighing by using an electronic balance, and calculating the extraction rate of the taraxasterol, wherein the calculation formula is as follows:
the sterol extraction rate is (taraxasterol mass/dried sow thistle mass) × 100%.
Dissolving taraxasterol in physiological saline to obtain taraxasterol solution with concentration of 0.150g/mL, and refrigerating in dark for use.
The structural formula of the taraxasterol obtained by the invention is shown in figure 2.
Example 1
The invention relates to a method for extracting taraxasterol from sow thistle, which comprises the following steps:
firstly, refluxing and extracting;
(1) cleaning fresh sow thistle leaves, drying, weighing 1000g of crushed sow thistle leaves, screening by a 60-mesh sieve, and placing in a round-bottom flask;
specifically, washing the bitter herb leaves with deionized water for 4 times, and drying the washed bitter herb leaves with a constant-temperature air-blast drying oven at 60 ℃ for 4 hours while stirring once per hour during drying;
(2) dividing the sample into 2 parts, respectively adding 10 times of methanol by mass, heating under reflux in a water bath at 80 ℃ for 5h, simultaneously heating under reflux, combining the reaction liquid, and filtering to obtain a filtrate;
(3) recycling most of methanol from the filtrate by a rotary evaporator to obtain a concentrate;
(4) treating the concentrate in 80 deg.C water bath for 10min to obtain herba Sonchi Oleracei extract;
(5) adding 1000ml of 1% sodium hydroxide solution into the sow thistle extract to dilute the sow thistle, and transferring the sow thistle into a separating funnel;
in this embodiment, the above steps are performed simultaneously, so as to obtain a mixed solution of sow thistle diluted with a sodium hydroxide solution with a mass fraction of 1%, and the mixed solution is analyzed by using a Varian INOVA-400MHz nuclear magnetic resonance spectrometer, so as to obtain data in table 1;
TABLE 1 carbon Spectroscopy (C- -NMR) data (CDCl) of Compounds I to VIII3,100MHz,δ,TMS)
R1＝CO(CH2)14CH3
According to the found literature, the compound I in the table 1 is the data of taraxasterol, taraxasterol does exist in the mixed solution of the sow thistle diluted by the sodium hydroxide solution, and the rest compounds are other impurities;
(6) adding 1000mL of ether for extraction, vibrating for 6 minutes, standing for layering, removing ether insoluble substances, continuously extracting for 5 times, and mixing ether extract;
(7) placing the extract on a rotary evaporator, recovering all ether, and vacuum drying the residue at-8 deg.C to obtain yellow paste, i.e. crude taraxasterol.
Secondly, purifying crude taraxasterol
Adding 500mL of acetone into the crude taraxasterol, heating for dissolving, naturally cooling for crystallization, separating out white crystals which are further purified taraxasterol crude products, filtering while the crude products are cold, collecting, recrystallizing for 3 times by using 500mL of ethanol, drying in vacuum at-8 ℃ to obtain white powdery substances, namely taraxasterol, treating the white powdery substances by using a vanillin sulfate solution to show red color, weighing by using an electronic balance, and calculating the taraxasterol extraction rate.
In this example, 1.06g of taraxasterol can be extracted from 1000g of herba Sonchi Oleracei, and the extraction rate of taraxasterol is 0.106%.
Analysis of taraxasterol using a Varian INOVA-400MHz NMR instrument gave the following C, H data for the carbon spectrum:
mp 190～193℃，1H-NMR(400MHz)，W.4.61(2H，m，H-30)，3.20(1H，dd，m，J＝2.4，10.2Hz，H-3)，1.63(3H，s，H-29)，1.04(3H，s，H-26)，0.90(3H，s，H-27)，1.02(3H，s，H-23)，0.93(3H，s，H-28)，0.83(3H，s，H-25)，0.77(3H，s，H-24)；
the data are consistent with the literature reports and the table 1, and are determined as taraxasterol.
Dissolving taraxasterol in physiological saline to obtain taraxasterol herba Taraxaci with concentration of 0.150g/mL, and refrigerating in dark place.
Example 2
The invention relates to a method for extracting taraxasterol from sow thistle, which comprises the following steps:
firstly, refluxing and extracting;
(1) cleaning fresh sow thistle leaves, drying, weighing 1000g of crushed sow thistle leaves, screening by a 60-mesh sieve, and placing in a round-bottom flask;
specifically, the bitter herb leaves are washed by deionized water for 3 times, and the washed bitter herb leaves are dried by a constant-temperature air-blowing drying oven, wherein the drying temperature is 40 ℃, the drying time is 8 hours, and the stirring is carried out once every 0.5 hour during the drying period;
(2) dividing the sample into 3 parts, respectively adding 10 times of methanol by mass, heating under reflux in a water bath at 85 ℃ for 4h, simultaneously heating under reflux, combining the reaction liquid, and filtering to obtain a filtrate;
(3) recycling most of methanol from the filtrate by a rotary evaporator to obtain a concentrate;
(4) treating the concentrate in 85 deg.C water bath for 5min to obtain herba Sonchi Oleracei extract;
(5) adding 1000ml of sodium hydroxide solution with the mass fraction of 5% into the sow thistle extract to dilute the sow thistle, and transferring the sow thistle into a separating funnel;
(6) adding 1000mL of ether for extraction, vibrating for 5 minutes, standing for layering, removing ether insoluble substances, continuously extracting for 6 times, and mixing ether extract;
(7) placing the extract on a rotary evaporator, recovering all the ether, and vacuum drying the residue at 0 deg.C to obtain yellow paste, i.e. crude taraxasterol.
Secondly, purifying crude taraxasterol
Adding 500mL of acetone into the crude taraxasterol, heating for dissolving, naturally cooling for crystallization, separating out white crystals which are further purified taraxasterol crude products, filtering while the crude products are cold, collecting, recrystallizing for 5 times by using 500mL of ethanol, drying in vacuum at 0 ℃ to obtain white powdery substances which are taraxasterol, weighing by using an electronic balance, and calculating the extraction rate of the taraxasterol.
Dissolving taraxasterol in physiological saline to obtain taraxasterol herba Taraxaci with concentration of 0.150g/mL, and refrigerating in dark place.
Example 3
The invention relates to a method for extracting taraxasterol from sow thistle, which comprises the following steps:
firstly, refluxing and extracting;
(1) cleaning fresh sow thistle leaves, drying, weighing 1000g of crushed sow thistle leaves, screening by a 50-mesh sieve, and placing in a round-bottom flask;
specifically, the bitter herb leaves are washed by deionized water for 3 times, and the washed bitter herb leaves are dried by a constant-temperature air-blowing drying oven, wherein the drying temperature is 50 ℃, the drying time is 6 hours, and the stirring is carried out once every 0.5 hour during the drying period;
(2) dividing the sample into 3 parts, respectively adding 10 times of methanol by mass, heating under reflux in 82 ℃ water bath for 4h, simultaneously heating under reflux, combining the reaction solution, and filtering to obtain a filtrate;
(3) recycling most of methanol from the filtrate by a rotary evaporator to obtain a concentrate;
(4) treating the concentrate in 83 deg.C water bath for 7min to obtain herba Sonchi Oleracei extract;
(5) adding 1000ml of purified water into the sow thistle extract to dilute the sow thistle, and transferring the sow thistle into a separating funnel;
(6) adding 1000mL of ether for extraction, vibrating for 5 minutes, standing for layering, removing ether insoluble substances, continuously extracting for 6 times, and mixing ether extract;
(7) placing the extract on a rotary evaporator, recovering all the diethyl ether, and vacuum drying the residue at-5 deg.C to obtain yellow paste, i.e. crude taraxasterol.
Secondly, purifying crude taraxasterol
Adding 500mL of acetone into the crude taraxasterol, heating for dissolving, naturally cooling for crystallization, separating out white crystals which are further purified taraxasterol crude products, filtering while the crude products are cold, collecting, recrystallizing for 4 times by using 500mL of ethanol, drying in vacuum at-3 ℃ to obtain white powdery substances which are taraxasterol, weighing by using an electronic balance, and calculating the extraction rate of the taraxasterol.
Dissolving taraxasterol in physiological saline to obtain taraxasterol herba Taraxaci with concentration of 0.150g/mL, and refrigerating in dark place.
Claims (10)
1. A method for extracting taraxasterol from sow thistle is characterized by comprising the following steps:
step 1, cleaning and drying sow thistle leaves, then crushing the sow thistle leaves, adding methanol to obtain a mixed system A, and carrying out reflux heating treatment on the mixed system A at the temperature of 80-85 ℃ to obtain a reaction solution;
step 2, filtering the reaction solution to obtain filtrate, performing rotary evaporation on the filtrate, and performing heat treatment on the obtained concentrate at the temperature of 80-85 ℃ to obtain sow thistle extractum;
step 3, adding purified water or a sodium hydroxide solution with the mass fraction of 1-5% into the sow thistle extract, extracting with diethyl ether to obtain an extract, removing the diethyl ether in the extract, and drying to obtain crude taraxasterol;
and 4, sequentially purifying the crude taraxasterol by using acetone and ethanol, and drying to obtain the taraxasterol.
2. The method for extracting taraxasterol from herba Sonchi Oleracei of claim 1, wherein in step 1, the cleaned herba Sonchi Oleracei leaves are dried at 40-60 deg.C for 4-8 h while stirring every 0.5-1 h.
3. The method for extracting taraxasterol from sow thistle according to claim 1, wherein in step 1, the crushed sow thistle leaves are screened by a 40-60-mesh screen and then added with methanol.
4. The method for extracting taraxasterol from herba Sonchi Oleracei of claim 1, wherein the amount of methanol added in step 1 is 10 times of the amount of pulverized herba Sonchi Oleracei leaves.
5. The method for extracting taraxasterol from sow thistle according to claim 1, wherein in the step 1, the mixed system A is refluxed and heated at the temperature for 4-5 hours to obtain a reaction solution.
6. The method for extracting taraxasterol from sow thistle according to claim 1, wherein in step 1, the crushed sow thistle leaves are divided into 2-3 parts and subjected to the reflux heating treatment, and then the obtained liquids are combined to obtain a reaction solution.
7. The method for extracting taraxasterol from sow thistle according to claim 1, wherein the concentrate is subjected to heat treatment at the temperature for 5-10 min in the step 2 to obtain the sow thistle extract.
8. The method for extracting taraxasterol from herba Sonchi Oleracei of claim 1, wherein in step 3, the ether in the extractive solution is removed and vacuum dried at-8-0 deg.C.
9. The method for extracting taraxasterol from herba Sonchi Oleracei of claim 1, wherein in step 4, acetone is added into crude taraxasterol, and then the mixture is dissolved by heating, cooled and crystallized naturally, filtered and collected, and then recrystallized with ethanol for 3-5 times, and then dried.
10. The method for extracting taraxasterol from herba Sonchi Oleracei of claim 1, wherein step 4 is carried out by vacuum drying the purified crude taraxasterol at-8-0 deg.C to obtain taraxasterol.
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