CN108440617B - Method for extracting glucoside compound from coptis chinensis - Google Patents
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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Abstract
The invention discloses a method for extracting glucoside compounds from coptis chinensis, which comprises the following steps: step A, taking the root of the coptis chinensis, adding water for leaching to obtain coptis chinensis extract; b, taking the coptis chinensis extract, adjusting the pH value of the coptis chinensis extract, acidifying to separate out alkaloid, filtering, adjusting the pH value of the filtrate back, and collecting liquid for later use; and C, separating and purifying the liquid collected in the step B to obtain the compound shown in the formula (I). In the whole process, only a small amount of highly safe ethanol and completely harmless water are used as solvents, so that the glucoside compound shown in the formula (I) with higher medicinal value of reducing blood sugar and higher purity of more than 95 percent can be extracted, and berberine alkaloids can be obtained as byproducts.
Description
Technical Field
The invention relates to the field of medical chemistry, in particular to a method for extracting glucoside compounds from coptis chinensis.
Background
Coptis chinensis Franch belonging to Ranunculaceae and Coptis perennial herbaceous plant. It is recorded in Shen nong Ben Cao Jing (Shen nong's herbal classic) for the earliest time, and its rhizome is in the shape of a pearl and yellow, so it is called "Huang Lian", which is a traditional Chinese herbal medicine in China. Huang Lian is cold and bitter in nature, and enters heart, liver and large intestine meridians. It has the actions of clearing heat and drying dampness, purging fire and removing toxicity, and is indicated for high fever, recklessly blood flow, dysphoria with heart fire, vomiting due to stomach heat, dysentery due to damp-heat, sore and ulcer with swelling and pain. Wild or cultivated in a valley cool and wet shading dense forest with elevation of 1000-1900m, which is mainly distributed in Sichuan province, Chongqing province, Hubei province, Hunan province, Shaanxi province, Gansu province and the like. The chemical components mainly comprise alkaloids and lignans 2, and also comprise phenolic acid, volatile oil, flavonoids, coumarin, terpenes, steroids, polysaccharides and the like. Modern pharmacological studies prove that the coptis extract has the effects of resisting bacteria, diminishing inflammation, resisting diarrhea, calming, hypnotizing, resisting ulcer, reducing blood pressure, blood fat and blood sugar, resisting arrhythmia, resisting tumors and the like.
The compound 15 reported in the existing document "separation and identification of chemical components of coptis water extract" (li xue modification et al, shenyang pharmaceutical science university, vol. 29, No. 3, p. 193-198) is separated from coptis plants for the first time, but has the problems of complicated extraction steps, high cost and low yield and purity.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: aiming at the problems that the method for extracting the glucoside compound shown in the formula (1) in the prior art is complex and has low yield and purity, the invention provides a method for extracting the glucoside compound from coptis chinensis.
The invention is realized by the following technical scheme:
a method for extracting glycoside compounds from Coptidis rhizoma, the structural formula of the compounds is shown as formula (I),
the extraction method comprises the following steps:
step A, taking the root of the coptis chinensis, adding water or ethanol for leaching or reflux extraction to obtain coptis chinensis extract;
b, taking the coptis chinensis extract, controlling the pH value to precipitate alkaloid, filtering and collecting liquid for later use;
and C, separating and purifying the liquid collected in the step B to obtain the compound shown in the formula (I).
Preferably, in the step A, the root powder of the coptis chinensis is soaked for 20-30 min, wherein the mass ratio of the root of the coptis chinensis to water or 0-100% ethanol water is 1: 2-1: 20.
Preferably, in the step A, after soaking, soaking at normal temperature for 8-30 h; or heating water to 30-100 ℃ for leaching for 0.5-4 h; or reflux extraction for 0.5-4 h.
Preferably, in the step B, the pH value is controlled to be 3-7, and standing treatment is carried out for 0.5-30 hours; and controlling the pH value of the filtered filtrate within the range of 3-7.
Preferably, in the step B, the coptis chinensis extracting solution is concentrated to 1/20-1/2 of the volume of the original extracting solution, and then alkaloid precipitation treatment is performed.
Preferably, in the step C, the collected liquid is sequentially separated and purified by a macroporous resin column and a reversed phase column.
Preferably, before the macroporous resin column is adopted for separation and purification, the pH value of a sample to be subjected to column separation is controlled to be 6-10.
Preferably, pure water, 5% v/v ethanol and 15% v/v ethanol are sequentially used for elution in the process of separating and purifying by adopting a macroporous resin column; or sequentially eluting with pure water and alkaline water with the pH of 8-13, and finally combining and collecting the eluent containing the compound shown in the formula (I).
Preferably, in the process of separating and purifying by adopting a reverse phase column, gradient elution is carried out for 0.5-3 h by using 0 → 50% ethanol water solution; or eluting with methanol water solution 0 → 50% gradient for 0.5-3 h, and collecting eluate containing compound of formula (I).
Preferably, after the separation and purification by adopting a macroporous resin column and a reverse phase column, the target fractions are determined by thin layer chromatography tracking and HPLC detection, and finally, the eluent containing the compound of the formula (I) is combined and collected.
Preferably, the macroporous resin column is filled with D101 macroporous resin, AB-8 macroporous resin, D3520 macroporous resin or X-5 macroporous resin as a filler, and the temperature of the column is room temperature, and the pressure is atmospheric pressure, wherein a 4X 40cm glass chromatographic column is used, or a 5X 30cm glass chromatographic column is used, or a 10X 150cm glass chromatographic column is used, or a 3X 30cm glass chromatographic column is used; the reverse column was either a 37X 300mm ODS-SM-50C glass column packed with Cosmosil 75C18-PREP or a Flash pre-packed column packed with AQ-C18, specification 120g or 300 g.
The invention has the following advantages and beneficial effects:
1. the invention provides a method for extracting compounds from coptis roots, which comprises the steps of carrying out water extraction and acidification on the coptis roots to obtain an extracting solution containing glucoside compounds (I) to the maximum extent, removing most alkaloid substances, and finally carrying out corresponding improvement, optimized separation and purification operations to obtain the glucoside compounds with the formula (I) and higher yield and purity of more than 95%, wherein the overall operation steps are simple and convenient, and the consumed time is short;
2. the compound shown in the formula (I) obtained by the preparation method has good blood sugar reduction effect and higher application value in the aspect of treating diabetes and diabetic complications;
3. in the step B, after acidification treatment, filter residue obtained by filtering can be treated by the means of the prior art to obtain the berberine alkaloids, so the method provided by the invention is green and environment-friendly, does not cause resource waste, and is beneficial to realizing comprehensive extraction and utilization of effective components in coptis chinensis.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail below with reference to examples, and the exemplary embodiments and descriptions thereof are only used for explaining the present invention and are not used as limitations of the present invention.
Example 1
The embodiment provides a method for extracting a compound shown as a formula I from coptis chinensis, which comprises the following specific operation steps:
1) cleaning root of Coptidis rhizoma, removing impurities, drying, pulverizing to obtain Coptidis rhizoma powder, weighing 100g Coptidis rhizoma powder, soaking in 8 times of water for 20min, and extracting in 30 deg.C water bath for 4 hr; filtering, extracting the residue with the above method once more, and mixing the two filtrates to obtain Coptidis rhizoma extractive solution;
2) decompressing and concentrating the coptis chinensis medicinal material extract to 1/6 of the original extract, adjusting the pH value of the concentrated solution to 4 by using concentrated hydrochloric acid with the concentration of 35-37%, standing and acidifying for 1h to fully salify and separate out alkaloid, filtering, and adjusting the pH value of the filtrate back to 6 by using 10% sodium hydroxide aqueous solution;
3) concentrating the filtrate, separating with macroporous resin column, eluting with 2 times of pure water, sequentially eluting with 1 times of 5% ethanol and 2 times of 15% ethanol, detecting eluate fractions, and collecting the concentrate containing compound of formula (I). Wherein the macroporous resin column adopts a 4 × 40cm glass chromatographic column, D101 macroporous resin is used as a filler to fill the column, the temperature of the column is room temperature, and the pressure is atmospheric pressure; the detection method of fractions is thin-layer chromatography tracking and chromogenic detection by using a sugar color developing agent.
Loading the concentrated solution containing glycoside substance separated and purified by macroporous resin to a reverse phase column, performing automatic gradient elution with ethanol water solution of 0 → 25% for 2h, wherein the gradient of the automatic elution is shown in Table 1, detecting fractions, combining, and collecting the eluted fractions to obtain the substance component containing the compound of formula (I). Wherein, the reverse column is a 37X 300mm ODS-SM-50C glass column, and the packing is Cosmosil 75C 18-PREP. The instrument is an MP200 medium-pressure preparation chromatograph of Agela Technologies; the detection method of the fractions is the same as that of macroporous resin fractions, thin-layer tracking is used, the fractions containing the target products are preliminarily determined, and HPLC (high performance liquid chromatography) detection is selectively carried out to determine the final target fractions.
The final product was obtained in 66% yield and 95.67% purity by HPLC.
TABLE 1 reversed phase elution gradient chart
The product purity detection method comprises the following steps:
the prepared product is detected by using an LC-16 Shimadzu high performance liquid chromatograph, 5mg of the final product is precisely weighed and placed in a 5mL volumetric flask for dissolving and constant volume, and then the purity of the product is detected under the following chromatographic conditions.
A chromatographic column: diamosil C18(2) (250X 4.6mm,5 μm)
Detection wavelength: 220nm
Flow rate: 1.0mL/min
Column temperature: 30 deg.C
Sample introduction amount: 20 μ L
Mobile phase: acetonitrile-0.1% trifluoroacetic acid in water (gradient see Table 2)
TABLE 2 HPLC elution gradient
Example 2
The embodiment provides a method for extracting a compound shown as a formula I from coptis chinensis, which comprises the following specific operation steps:
1) cleaning root of Coptidis rhizoma, removing impurities, drying, pulverizing to obtain Coptidis rhizoma powder, weighing 300g Coptidis rhizoma powder, soaking in 10 times of water for 25min, and extracting in 100 deg.C water bath for 0.5 h; filtering, extracting the residue with the above method once more, and mixing the two filtrates to obtain Coptidis rhizoma extractive solution;
2) decompressing and concentrating the coptis chinensis medicinal material extract to 1/8 of the original extract, adjusting the pH value of the concentrated solution to 3.5 by using concentrated hydrochloric acid with the concentration of 35-37%, standing and acidifying for 1.2h to fully salify and separate out alkaloid, filtering, and adjusting the pH value of the filtrate back to 6.5 by using 10% sodium hydroxide aqueous solution;
3) concentrating the filtrate, separating with macroporous resin column, eluting with 2 times of pure water, sequentially eluting with 1 times of 5% ethanol and 2 times of 15% ethanol, detecting eluate fractions, and collecting the concentrate containing compound of formula (I). Wherein the macroporous resin column adopts a 4 × 40cm glass chromatographic column, and AB-8 macroporous resin is used as a filler to fill the column, the temperature of the column is room temperature, and the pressure is atmospheric pressure; the detection method of fractions is thin-layer chromatography tracking and chromogenic detection by using a sugar color developing agent.
Loading the concentrated solution containing glycoside substance separated and purified by macroporous resin to a reverse phase column, performing gradient elution with ethanol water solution of 0 → 30% for 2h, detecting fractions with automatic elution gradient table shown in Table 3, mixing, and collecting eluate to obtain substance component containing compound of formula (I). Wherein, the reverse column is a 37X 300mm ODS-SM-50C glass column, and the packing is Cosmosil 75C 18-PREP. The instrument is an MP200 medium-pressure preparation chromatograph of Agela Technologies; the flow detection method is the same as that of macroporous resin, thin-layer tracking is used, the flow containing the target product is preliminarily determined, and the final target flow is determined after selective HPLC detection.
The final product was obtained in 65% yield and 97.03% purity by HPLC. The purity was measured in the same manner as in "example 1".
TABLE 3 inverse elution gradient
Example 3
The embodiment provides a method for extracting a compound shown as a formula I from coptis chinensis, which comprises the following specific operation steps:
1) cleaning root of Coptidis rhizoma, removing impurities, drying, pulverizing to obtain Coptidis rhizoma powder, weighing 220g Coptidis rhizoma powder, soaking in 6 times of water for 30min, and extracting in 80 deg.C water bath for 1.5 hr; filtering, extracting the residue with the above method once more, and mixing the two filtrates to obtain Coptidis rhizoma extractive solution;
2) decompressing and concentrating the coptis chinensis medicinal material extract to 1/10 of the original extract, adjusting the pH value of the concentrated solution to 4.5 by using concentrated hydrochloric acid with the concentration of 35-37%, standing and acidifying for 1.5h to fully salify and separate out alkaloid, filtering, and adjusting the pH value of the filtrate back to 5.6 by using 10% sodium hydroxide aqueous solution;
3) concentrating the filtrate, separating with macroporous resin column, eluting with 2 times of pure water, sequentially eluting with 1 times of 5% ethanol and 2 times of 15% ethanol, detecting eluate fractions, and collecting the concentrate containing compound of formula (I). Wherein the macroporous resin column adopts a 4 × 40cm glass chromatographic column, D101 macroporous resin is used as a filler to fill the column, the temperature of the column is room temperature, and the pressure is atmospheric pressure; the detection method of fractions is thin-layer chromatography tracking and chromogenic detection by using a sugar color developing agent.
Loading the concentrated solution containing glycoside substance separated and purified by macroporous resin to a reverse phase column, performing automatic gradient elution with ethanol water solution of 0 → 25% for 2h, wherein the gradient of the automatic elution is shown in Table 1, detecting fractions, combining, and collecting the eluted fractions to obtain the substance component containing the compound of formula (I). Wherein, the reverse column is a 37X 300mm ODS-SM-50C glass column, and the packing is Cosmosil 75C 18-PREP. The instrument is an MP200 medium-pressure preparation chromatograph of Agela Technologies; the flow detection method is the same as that of macroporous resin, thin-layer tracking is used, the flow containing the target product is preliminarily determined, and the final target flow is determined after selective HPLC detection.
The yield of the finally prepared product is 63 percent, the purity is 95 percent by HPLC detection, and the purity detection method is the same as that in the detection of the 'example 1'.
Example 4
The embodiment provides a method for extracting a compound shown as a formula I from coptis chinensis, which comprises the following specific operation steps:
1) cleaning root of Coptidis rhizoma, removing impurities, drying, pulverizing to obtain Coptidis rhizoma powder, weighing 400g Coptidis rhizoma powder, adding 2 times of 15% ethanol water solution, soaking for 30min, and reflux extracting for 2 hr; filtering, extracting the residue with the above method once more, and mixing the two filtrates to obtain Coptidis rhizoma extractive solution;
2) concentrating the Coptidis rhizoma extractive solution under reduced pressure to 1/4 of the original extractive solution, measuring pH to 5.67, standing overnight to fully precipitate alkaloid, and filtering;
3) concentrating the filtrate, adjusting the pH of the concentrated solution to 8.96 by using a 10% sodium hydroxide aqueous solution, separating by using a macroporous resin column, eluting by using 2 times of column volume of pure water, eluting by using 4 times of column volume of alkaline water (pH is 10-12), detecting fractions of the eluate, and collecting the concentrated solution containing the compound substance of the formula (I). Wherein, the macroporous resin column adopts a 5 multiplied by 30cm glass chromatographic column, D101 macroporous resin is used as filler to fill the column, the temperature of the column is room temperature, and the pressure is atmospheric pressure; the detection method of fractions is thin-layer chromatography tracking and chromogenic detection by using a sugar color developing agent.
Loading the concentrated solution of the glycoside-containing substance solution separated and purified by macroporous resin to a reverse phase column, performing gradient elution with ethanol water solution for 1.5h, wherein the elution gradient is shown in Table 4, detecting fractions, combining, and collecting the eluted fractions to obtain the substance component containing the compound of formula (I). Wherein, the reverse column uses a Flash prepacked column of 120g, and the packing is AQ-C18. The instrument is an MP200 medium-pressure preparation chromatograph of Agela technologies; the flow detection method is the same as that of macroporous resin, thin-layer tracking is used, the flow containing the target product is preliminarily determined, and the final target flow is determined after selective HPLC detection.
The yield of the finally prepared product is 63%, the purity of the finally prepared product is 95.97% by HPLC detection, and the purity detection method is the same as that in 'example 1'.
TABLE 4 reverse phase elution gradiometer
Example 5
The embodiment provides a method for extracting a compound shown as a formula I from coptis chinensis, which comprises the following specific operation steps:
1) cleaning the root of the coptis chinensis, removing impurities, drying, crushing to obtain coptis chinensis powder, weighing 500g of coptis chinensis powder, and adding 20 times of water to soak for 24 hours; filtering, extracting the residue with the above method once more, and mixing the two filtrates to obtain Coptidis rhizoma extractive solution;
2) decompressing and concentrating the coptis chinensis medicinal material extract to 1/20 of the original extract, adjusting the pH value of the concentrated solution to 4.9 by using concentrated hydrochloric acid with the concentration of 35-37%, standing and acidifying for 4 hours to fully salify and separate out alkaloid, and filtering;
3) concentrating the filtrate, adjusting the pH of the concentrated solution to 9.31 with 10% sodium hydroxide aqueous solution, separating with macroporous resin column, eluting with 2 times of column volume of pure water, eluting with 5 times of column volume of alkaline water (pH 12-13), collecting eluate, detecting, and collecting the concentrated solution containing compound of formula (I). Wherein the macroporous resin column adopts a 10 × 150cm glass chromatographic column, D101 macroporous resin is used as a filler to fill the column, the temperature of the column is room temperature, and the pressure is atmospheric pressure; the detection method of fractions is thin-layer chromatography tracking and chromogenic detection by using a sugar color developing agent.
Loading the concentrated solution of the glycoside-containing substance solution separated and purified by macroporous resin to a reverse phase column, performing gradient elution with methanol water solution for 1.5h, detecting fractions with an automatic elution gradient table shown in Table 5, mixing, and collecting the eluted fractions to obtain the substance component containing the compound of formula (I). Wherein, the reverse column uses 300g Flash prepacked column, and the packing is AQ-C18. The instrument is an MP200 medium-pressure preparation chromatograph of Agela technologies; the flow detection method is the same as that of macroporous resin, thin-layer tracking is used, the flow containing the target product is preliminarily determined, and the final target flow is determined after selective HPLC detection.
The yield of the finally prepared product is 72 percent, the purity is 95.98 percent by HPLC detection, and the purity detection method is the same as that in the detection of the 'example 1'.
TABLE 5 inverse elution gradient chart
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are merely exemplary embodiments of the present invention, and are not intended to limit the scope of the present invention, and any modifications, equivalent substitutions, improvements and the like made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (5)
1. A method for extracting glucoside compounds from rhizoma Coptidis is characterized in that the structural formula of the compounds is shown in formula (I),
the extraction method comprises the following steps:
step A, taking the root of the coptis chinensis, adding water or ethanol for leaching or reflux extraction to obtain coptis chinensis extract;
b, taking the coptis chinensis extract, controlling the pH value to precipitate alkaloid, filtering and collecting liquid for later use;
step C, separating and purifying the liquid collected in the step B to obtain a compound shown in a formula (I);
in the step B, the pH value is controlled to be 3.5-7, and standing treatment is carried out for 0.5-30 hours; controlling the pH value of the filtered filtrate within the range of 3-7;
in the step C, separating and purifying the collected liquid by a macroporous resin column and a reverse phase column in sequence;
before separation and purification by adopting a macroporous resin column, controlling the pH value of a sample to be subjected to column separation to be 6-10;
eluting with pure water and ethanol in sequence during the separation and purification process by adopting a macroporous resin column; or sequentially eluting with pure water and alkaline water with the pH of 8-13, and finally merging and collecting the eluent containing the compound of the formula (I);
gradient elution is carried out by using ethanol water solution in the process of separating and purifying by adopting a reverse phase column; or eluting with methanol water solution, and collecting eluates containing compound of formula (I);
the macroporous resin column adopts a glass chromatographic column, and D101 macroporous resin is used as filler for filling the column or AB-8 macroporous resin is used as filler for filling the column;
the reverse column adopts an ODS-SM-50C glass column, and the filler is Cosmosil 75C 18-PREP; or a Flash prepacked column is adopted as the reverse column, and AQ-C18 is used as the packing.
2. The method of claim 1, wherein in the step A, the coptis root powder is soaked, wherein the mass ratio of the coptis root to water or 0-100% ethanol water is 1: 2-1: 20.
3. The method for extracting glycoside compounds from coptis chinensis according to claim 2, wherein in the step A, after soaking, filtration is carried out, and filter residues are soaked for 8-30 hours at normal temperature; or heating water to 30-100 ℃ for leaching for 0.5-4 h; or reflux extraction for 0.5-4 h.
4. The method for extracting glycosides compounds from Coptidis rhizoma according to claim 1, wherein in the step B, the Coptidis rhizoma extract is concentrated to 1/20-1/2 of the volume of the original extract, and then alkaloid precipitation is performed.
5. The method as claimed in claim 1, wherein the target fractions are determined by TLC and HPLC after the purification with macroporous resin column and reversed phase column, and the eluates containing the compound of formula (I) are collected.
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| CN1386527A (en) * | 2001-05-23 | 2002-12-25 | 周亚伟 | Chinese medicine composition for treating diabetes and its preparing process |
| CN107519191A (en) * | 2016-06-22 | 2017-12-29 | 成都中创蜀洋生物科技有限公司 | Glucoside compound is preparing the purposes in treating diabetes medicament |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1386527A (en) * | 2001-05-23 | 2002-12-25 | 周亚伟 | Chinese medicine composition for treating diabetes and its preparing process |
| CN107519191A (en) * | 2016-06-22 | 2017-12-29 | 成都中创蜀洋生物科技有限公司 | Glucoside compound is preparing the purposes in treating diabetes medicament |
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| Isolation and characterization of phenolic compounds from coptidis rhizome;Shoji Yahara, 等;《Chemical & Pharmaceutical Bulletin》;19851231;第33卷(第2期);第527-531页 * |
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