CN109369769B - Method for extracting and separating hecolone monomer from stems and leaves of tribulus terrestris - Google Patents
Method for extracting and separating hecolone monomer from stems and leaves of tribulus terrestris Download PDFInfo
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- CN109369769B CN109369769B CN201811246837.9A CN201811246837A CN109369769B CN 109369769 B CN109369769 B CN 109369769B CN 201811246837 A CN201811246837 A CN 201811246837A CN 109369769 B CN109369769 B CN 109369769B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
Abstract
The invention discloses a method for extracting and separating hecolone monomers from stems and leaves of tribulus terrestris, belonging to the field of natural medicinal chemistry research. The invention takes the stems and leaves of tribulus terrestris as raw materials, the stems and leaves of tribulus terrestris are extracted by organic solvent, filtered, concentrated, the concentrated solution is diluted by water and then is absorbed by a macroporous absorption resin column, the water solution of low-concentration organic solvent is firstly used for elution, then the water solution of high-concentration organic solvent is used for elution, the spirost total saponin containing hecinone monomers is obtained, the spirost total saponin is taken for silica gel column chromatography separation, and the hecinone monomers are obtained. The preparation method has high extraction efficiency and simple operation, is suitable for industrial production, and the obtained hecolone monomer has high purity and can be used for preparing pharmaceutical compositions and other products.
Description
Technical Field
The invention relates to a method for extracting and separating hecolone monomers from stems and leaves of tribulus terrestris, belonging to the field of natural medicinal chemistry research.
Background
Tribulus terrestris L is a plant of Tribulus of Zygophyllaceae, and is an annual or perennial herb. The stem is branched from the base, the stem is spread on the ground, the branch length can reach 30-60cm, the leaf is a pinnate compound leaf, the shape is small and sharp, the fruit is composed of 5 branch fruit lobes which are arranged in a radial shape, and the diameter is 7-12 mm. It is a traditional Chinese medicine, also named as Tribulus terrestris, Tribulus terrestris seed, Tribulus terrestris. Has pungent, bitter, mild and mild natured taste, has little toxicity, enters liver and lung channels, has the effects of calming liver, resolving depression, promoting blood circulation, improving eyesight, relieving itching and the like, and is mainly used for treating symptoms such as headache, dizziness, breast obstruction, breast pain, rubella, pruritus and the like. Pharmacological research shows that the caltrop has the functions of antibiosis, anticancer, diuresis and the like, and has a more prominent curative effect on preventing and treating cardiovascular and cerebrovascular diseases.
Until now, people can obtain various steroid saponins from caltrops, including furosteroid saponins and spirosteroid saponins, which are the main effective components of caltrops. Modern researches find that the content and the variety of steroid saponin in stems and leaves of the caltrops are similar to those of fruits, and the extracts of the stems and leaves of the caltrops also have the effects of improving cardiovascular and cerebrovascular diseases, reducing blood fat, resisting fungi and the like. Hecolone (Hecogenone) is a spirosteroid saponin contained in stems and leaves of Tribulus terrestris, and has effects of scavenging hydroxy free radicals, inhibiting tyrosinase, and resisting fungi.
Disclosure of Invention
The invention provides a method for extracting and separating hecolone monomers from stems and leaves of tribulus terrestris.
In order to achieve the purpose, the invention adopts the following technical scheme:
extracting, filtering and concentrating stems and leaves of tribulus terrestris serving as a raw material by using an aqueous solution of an organic solvent, diluting a concentrated solution by using water, adsorbing the diluted concentrated solution by using a macroporous adsorption resin column, eluting by using an aqueous solution of a low-concentration organic solvent, then eluting by using an aqueous solution of a high-concentration organic solvent, tracking and monitoring by TLC (thin layer chromatography) to obtain spirost total saponins, and performing silica gel column chromatography separation on the spirost total saponins to finally obtain a hecinone monomer.
The extraction method of the caltrop stems and leaves comprises the following steps: pulverizing dried stems and leaves of fructus Tribuli, reflux-extracting with organic solvent water solution for three times, mixing the three extractive solutions, and recovering solvent. The water solution of the organic solvent is acetone water, methanol water or ethanol water, preferably 70-85% of acetone water, methanol water or ethanol water.
The macroporous adsorption resin is one or two or more mixed resins selected from AB-8, D103, D101 and HP 20.
The organic solvent is selected from ethanol, methanol, acetone or a mixed solvent of two or more of the ethanol, the methanol and the acetone.
The aqueous solution of the low-concentration organic solvent is an aqueous solution with the volume percentage concentration of less than or equal to 40 percent.
The high-concentration organic solvent aqueous solution is an aqueous solution with the volume percentage concentration of more than 40 percent.
After the extract of the stems and leaves of the tribulus terrestris is adsorbed by macroporous adsorption resin, the extract is eluted by aqueous solution of organic solvent with volume percentage concentration of less than 15 percent, then eluted by aqueous solution of organic solvent with volume percentage concentration of more than 15 percent to less than 40 percent to obtain furostanol type steroid saponin, and finally eluted by aqueous solution of organic solvent with volume percentage concentration of more than 40 percent to obtain spirostanol total saponin containing hecolone monomer.
The spirostan total saponin column chromatography is carried out by using ethyl acetate: ethanol: water is used as eluent, and the volume ratio is preferably 5: 3: 1 ethyl acetate: ethanol: separating with silica gel column chromatography with water as mobile phase to obtain component B containing hecolone monomer; mixing component B with petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography again with water as mobile phase to obtain hecolone monomer, preferably 6: 1: 1: 0.1. the preparation method has the advantages of reasonable process, high extraction efficiency, simple operation and high hecogenone purity, and is suitable for industrial production.
The hecolone monomer obtained by the invention can be used for preparing pharmaceutical compositions and other products.
Detailed Description
Preferred embodiments of the present invention are explained below. It should be understood that the preferred embodiments described herein are for purposes of illustration and explanation only and are not intended to limit the present invention.
Example 1
Pulverizing 5Kg of dried stems and leaves of fructus Tribuli, reflux-extracting with 70% ethanol water solution for three times (W/V) for 3h, 2h and 1h, respectively, mixing the three extractive solutions, and recovering solvent until no ethanol smell is detected. Diluting the concentrated solution with water, adsorbing the diluted solution with AB-8 macroporous adsorbent resin, washing with deionized water to colorless, eluting with 35% ethanol solution 8 times the column volume, concentrating the eluate, performing thin layer chromatography with chloroform-methanol-water (8: 4: 0.9) as developing agent, dissolving 0.5ml anisaldehyde with A reagent (50ml acetic acid, adding 1ml sulfuric acid) and E reagent (1% p-dimethylaminobenzaldehyde ethanol solution: concentrated hydrochloric acid (4; 1)) for color development, and collecting the eluate containing furosteroid saponin, eluting with 80% ethanol solution, recovering solvent under reduced pressure, and drying to obtain spirosteroid total saponin.
Taking 30g of spirostan total saponin, and mixing the spirostan total saponin with ethyl acetate: ethanol: water 5: 3: 1 (volume ratio) is used as a mobile phase to carry out silica gel column chromatography separation, and 10.1g of a component B containing hecolone monomers is obtained; mixing component B with petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography with water (6: 1: 1: 0.1, volume ratio) as mobile phase to obtain hecolone monomer.
The resulting hecolone monomer was structurally characterized by NMR and was 99.5% pure by HPLC-ELSD.
Nuclear magnetic data for hecolone are as follows
13C NMR(C5D5N，150MHz)c：38.12(C-1)，38.02(C-2)，209.72(C-3)，44.7(C-4)，46.37(C-5)，28.75(C-6)，31.43(C-7)，34.31(C-8)，54.96(C-9)，36.37(C-10)，38.12(C-11)，212.44(C-12)，55.47(C-13)，55.77(C-14)，31.53(C-15)，79.75(C-16)，54.42(C-17)，16.19(C-18)，10.88(C-19)，42.74(C-20)，14.01(C-21)，109.41(C-22)，31.89(C-23)，29.31(C-24)，30.63(C-25)，67.04(C-26)，17.40(C-27)。
1H NMR(C5D5N，600MHz)H：4.37(1H，m H-16)，3.48(1H，dd J＝10.7Hz H-26)，3.35(1H，t J＝10.8Hz H-26)，2.66-1.06(25H，m)，0.82(3H，s H-18)，1.00(3H，s H-19)，1.24(3H，d J＝6.1Hz H-21)，0.57(3H，d J＝6.3Hz H-27)。
HPLC-ELSD chromatographic conditions are as follows
A chromatographic column: agilent Eclipse XDB-C18(ODS, 4.6X 250nm, 5 μm)
Mobile phase: acetonitrile-water (45: 55); flow rate: 1L/min; column temperature: 30 deg.C
Sample introduction amount: 20 mu L of the solution; the temperature of a drift tube of an ELSD detector is 98 ℃; the state of the impactor: and closing.
Carrier gas pressure: 0.45Mpa atomizer flow rate: 2.6L/min magnification: 1.0 times of
Example 2
Pulverizing 5Kg of dried stems and leaves of fructus Tribuli, reflux-extracting with 70% methanol water solution for three times (W/V) for 3h, 2h and 1h, respectively, mixing the three extractive solutions, and recovering solvent until no alcohol smell is detected. Diluting the concentrated solution with water, passing the diluted solution through D101 macroporous adsorbent resin for adsorption, washing with deionized water until colorless, eluting with 30% methanol solution 8 times the column volume, concentrating the eluate, performing thin layer chromatography with chloroform-methanol-water (8: 4: 0.9) as developing agent, dissolving 0.5ml anisaldehyde with A reagent (50ml acetic acid, adding 1ml sulfuric acid) and E reagent (1% p-dimethylaminobenzaldehyde ethanol solution: concentrated hydrochloric acid (4; 1)) for color development, and eluting with furosteroid saponin completely, eluting with 80% methanol solution, recovering solvent under reduced pressure, and drying to obtain spirosteroid total saponin.
Taking 30g of spirostan total saponin, and mixing the spirostan total saponin with ethyl acetate: ethanol: separating with silica gel column chromatography with water (5: 3: 1, volume ratio) as mobile phase to obtain component B9.2g containing hecolone monomer; mixing component B with petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography with water (6: 1: 1: 0.1, volume ratio) as mobile phase to obtain hecolone monomer.
The purity of the product is 99.2% by HPLC-ELSD detection.
Example 3
Pulverizing 5Kg of dried stems and leaves of fructus Tribuli, extracting with 85% acetone solution for three times under reflux for 3h, 2h, and 1h, respectively, at an amount of 10, 8, and 6 times (W/V), mixing the three extractive solutions, and recovering solvent. Diluting the concentrated solution with water, passing the diluted solution through D4020 macroporous adsorbent resin for adsorption, washing with deionized water until colorless, eluting with 25% acetone solution 8 times the column volume, concentrating the eluate, performing thin layer chromatography with chloroform-methanol-water (8: 4: 0.9) as developing agent, dissolving 0.5ml anisaldehyde with A reagent (50ml acetic acid, adding 1ml sulfuric acid) and E reagent (1% p-dimethylaminobenzaldehyde ethanol solution: concentrated hydrochloric acid (4; 1)) for color development, and eluting with furosteroid saponin completely, eluting with 85% acetone solution, recovering solvent under reduced pressure, and drying to obtain spirosteroid total saponin.
Taking 30g of spirostan total saponin, and mixing the spirostan total saponin with ethyl acetate: ethanol: performing silica gel column chromatography with water (5: 3: 1, volume ratio) as mobile phase to obtain component B9.5g containing hecolone monomer; mixing component B with petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography with water (6: 1: 1: 0.1, volume ratio) as mobile phase to obtain hecolone monomer.
The purity of the product is 98.0% by HPLC-ELSD detection.
Example 4
Pulverizing 5Kg of dried stems and leaves of fructus Tribuli, reflux-extracting with 90% ethanol water solution for three times (W/V) for 3h, 2h and 1h, respectively, mixing the three extractive solutions, and recovering solvent until no ethanol smell is detected. Diluting the concentrated solution with water, adsorbing the diluted solution with HP20 macroporous adsorbent resin, washing with deionized water to colorless, eluting with 40% ethanol solution 8 times the column volume, concentrating the eluate, performing thin layer chromatography with chloroform-methanol-water (8: 4: 0.9) as developing agent, dissolving 0.5ml anisaldehyde with A reagent (50ml acetic acid, adding 1ml sulfuric acid) and E reagent (1% p-dimethylaminobenzaldehyde ethanol solution: concentrated hydrochloric acid (4; 1)) for color development, and eluting with furosteroid saponin, eluting with 95% ethanol solution, recovering solvent under reduced pressure, and drying to obtain spirosteroid total saponin.
Taking 30g of spirostan total saponin, and mixing the spirostan total saponin with ethyl acetate: ethanol: separating with silica gel column chromatography with water (5: 3: 1, volume ratio) as mobile phase to obtain component B8.5g containing hecolone monomer; mixing component B with petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography with water (6: 1: 1: 0.1, volume ratio) as mobile phase to obtain hecolone monomer.
The purity of the product was 97.5% by HPLC-ELSD.
Although the present invention has been described in detail in the foregoing embodiments, it will be apparent to those skilled in the art that modifications and equivalents may be made in the embodiments described above, or some features may be substituted for those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (4)
1. A method for extracting and separating hecolone monomers from stems and leaves of tribulus terrestris is characterized by comprising the following steps: pulverizing 5Kg of dried stems and leaves of fructus Tribuli, reflux-extracting with 70% ethanol water solution for three times (W/V) for 3h, 2h and 1h, respectively, mixing the three extractive solutions, and recovering solvent until no ethanol smell exists; diluting the concentrated solution with water, adsorbing the diluted solution by AB-8 macroporous adsorption resin, washing the diluted solution to be colorless by deionized water, eluting the diluted solution by 35 percent ethanol solution with 8 times of column volume, concentrating the eluent and then performing column chromatography by using a column chromatography column with the volume ratio of 8: 4: 0.9 chloroform-methanol-water as developing agent, dissolving 0.5ml anisaldehyde with 50ml acetic acid, adding 1ml A reagent with volume ratio of 4: 1, developing the color of a 1% p-dimethylaminobenzaldehyde ethanol solution and a concentrated hydrochloric acid E reagent, wherein the result shows that the eluted component is furostanol type steroid saponin, completely eluting the furostanol type steroid saponin, then eluting spirostanol type steroid saponin by using an 80% ethanol solution, recovering a solvent under reduced pressure, and drying to obtain spirostanol total saponin; taking 30g of spirostan total saponin, and mixing the spirostan total saponin with a volume ratio of 5: 3: 1 ethyl acetate: ethanol: separating with silica gel column chromatography with water as mobile phase to obtain component B containing hecolone monomer 10.1 g; and (3) mixing the component B in a volume ratio of 6: 1: 1: 0.1 of petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography again with water as mobile phase to obtain hecolone monomer.
2. A method for extracting and separating hecolone monomers from stems and leaves of tribulus terrestris is characterized by comprising the following steps: pulverizing 5Kg of dried stems and leaves of fructus Tribuli, reflux-extracting with 70% methanol aqueous solution for three times (W/V) for 3h, 2h and 1h, respectively, mixing the three extractive solutions, and recovering solvent until no alcohol smell is detected; diluting the concentrated solution with water, adsorbing the diluted solution by using D101 macroporous adsorption resin, washing the diluted solution to be colorless by using deionized water, eluting the diluted solution by using 30 percent methanol solution with 8 times of column volume, concentrating the eluent, and then using the mixed solution with the volume ratio of 8: 4: 0.9 chloroform-methanol-water as developing agent, dissolving 0.5ml anisaldehyde with 50ml acetic acid, adding 1ml A reagent with volume ratio of 4: 1, developing the color of a 1% p-dimethylaminobenzaldehyde ethanol solution and a concentrated hydrochloric acid reagent E, wherein the result shows that the component eluted at the time is furostanol type steroid saponin, completely eluting the furostanol type steroid saponin, then eluting the spirostanol type steroid saponin by using an 80% methanol solution, recovering a solvent under reduced pressure, and drying to obtain spirostanol total saponin; taking 30g of spirostan total saponin, and mixing the spirostan total saponin with a volume ratio of 5: 3: 1 ethyl acetate: ethanol: separating with silica gel column chromatography with water as mobile phase to obtain component B containing hecolone monomer 9.2 g; and (3) mixing the component B in a volume ratio of 6: 1: 1: 0.1 of petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography again with water as mobile phase to obtain hecolone monomer.
3. A method for extracting and separating hecolone monomers from stems and leaves of tribulus terrestris is characterized by comprising the following steps: pulverizing 5Kg of dried stems and leaves of fructus Tribuli, extracting with 85% acetone solution for three times under reflux for 3h, 2h and 1h, respectively, wherein the amount of acetone solution is 10, 8 and 6 times (W/V), mixing the three extractive solutions, and recovering solvent; diluting the concentrated solution with water, passing the diluted solution through D4020 macroporous adsorbent resin for adsorption, washing with deionized water until colorless, eluting with 25% acetone solution 8 times the column volume, concentrating the eluate, and purifying with a volume ratio of 8: 4: 0.9 chloroform-methanol-water as developing agent, dissolving 0.5ml anisaldehyde with 50ml acetic acid, adding 1ml A reagent with volume ratio of 4: 1, developing the color of a 1% p-dimethylaminobenzaldehyde ethanol solution and a concentrated hydrochloric acid reagent E, wherein the result shows that the eluted component is furosteroid saponin, completely eluting the furosteroid saponin, then eluting the spirosteroid saponin by using an 85% acetone solution, recovering the solvent under reduced pressure, and drying to obtain spirosteroid total saponin; taking 30g of spirostan total saponin, and mixing the spirostan total saponin with a volume ratio of 5: 3: 1 ethyl acetate: ethanol: separating with silica gel column chromatography with water as mobile phase to obtain component B containing hecolone monomer 9.5 g; and (3) mixing the component B in a volume ratio of 6: 1: 1: 0.1 of petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography again with water as mobile phase to obtain hecolone monomer.
4. A method for extracting and separating hecolone monomers from stems and leaves of tribulus terrestris is characterized by comprising the following steps: pulverizing 5Kg of dried stems and leaves of fructus Tribuli, reflux-extracting with 90% ethanol water solution for three times (W/V) for 3h, 2h and 1h, respectively, mixing the three extractive solutions, and recovering solvent until no ethanol smell exists; diluting the concentrated solution with water, adsorbing the diluted solution by HP20 macroporous adsorption resin, washing the diluted solution to be colorless by using deionized water, eluting the diluted solution by using 40 percent ethanol solution with 8 times of column volume, concentrating the eluent, and then using the eluent with the volume ratio of 8: 4: 0.9 chloroform-methanol-water as developing agent, dissolving 0.5ml anisaldehyde with 50ml acetic acid, adding 1ml A reagent with volume ratio of 4: 1, developing the color of a 1% p-dimethylaminobenzaldehyde ethanol solution and an E reagent of concentrated hydrochloric acid, wherein the result shows that the eluted component is furosteroid saponin, completely eluting the furosteroid saponin, then eluting the spirosteroid saponin by using a 95% ethanol solution, recovering a solvent under reduced pressure, and drying to obtain spirosteroid total saponin; taking 30g of spirostan total saponin, and mixing the spirostan total saponin with a volume ratio of 5: 3: 1 ethyl acetate: ethanol: separating with silica gel column chromatography with water as mobile phase to obtain component B8.5g containing hecolone monomer; and (3) mixing the component B in a volume ratio of 6: 1: 1: 0.1 of petroleum ether: ethyl acetate: ethanol: separating with silica gel column chromatography again with water as mobile phase to obtain hecolone monomer.
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| US2408834A (en) * | 1944-05-15 | 1946-10-08 | Parke Davis & Co | Steroidal compounds and methods for obtaining the same |
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| CN107296877A (en) * | 2017-06-09 | 2017-10-27 | 吉林瑞诺科技有限公司 | A kind of preparation method of Longstamen Onion Bulb group saponine |
| CN107296818A (en) * | 2017-06-15 | 2017-10-27 | 吉林大学 | A kind of method that total furostanol saponin and total spirostanol saponin are prepared from puncture vine |
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