CN111040008B - Method for preparing high-purity saponin and wensaining II in spina date seeds by adopting HSCCC - Google Patents
Method for preparing high-purity saponin and wensaining II in spina date seeds by adopting HSCCC Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
Abstract
The invention provides a method for preparing high-purity saponin and wensaining II in spina date seeds by adopting HSCCC, which comprises the steps of dissolving the spina date seeds in an alcohol solution, soaking, carrying out ultrasonic extraction, degreasing an extracting solution, concentrating and drying to obtain a crude product of total flavonoids; separating and purifying the crude product of the general flavone by using a HSCCC method and a first set of solution system and a second set of solution system to prepare saponin and wensaining II; the method provided by the invention can prepare the saponin and the wensaining II with high purity.
Description
Technical Field
The invention belongs to the field of preparation of effective components, and particularly relates to a method for preparing high-purity saponin and wensaining II in wild jujube kernels by adopting HSCCC.
Background
The modern society is rapidly developed, the pressure of working and living of people is getting bigger, the symptoms such as anxiety, insomnia and the like which are generated therewith continuously disturb the normal life of people, the insomnia people are very common in adults, and long-term insomnia is one of the main causes of inducing depression, accelerating aging, reducing the immunity of the organism and inducing cancer and the like. At present, barbiturates (phenobarbital and the like), benzodiazepines (diazepam and the like) and pyrrolidone non-benzodiazepines (zopiclone and the like) anti-insomnia medicines are mainly used as sedative and hypnotic medicines for insomnia, but the sedative and hypnotic medicines have obvious adverse reactions on the central nervous system, and not only can generate drug resistance after long-term use, but also can aggravate the state of an illness, so that a patient can generate tolerance and finally cause treatment failure, so that the demands for researching and developing traditional Chinese medicine heart-nourishing tranquilizers to regulate sleep, particularly medicines simulating physiological sleep are increasingly demanded. The study proves that the spina date seed has good effect on insomnia and neurasthenia caused by various causes, is a classic sedative-hypnotic traditional Chinese medicine, and has the advantages of stable curative effect, safety and the like. At present, the most studied preparation is monomer components such as flavone, saponin, alkaloid and the like in the spina date seeds. The preparation research on flavone components such as saponin and Wenxinin II is few, the two components have good antioxidant activity and are active parts for tranquilizing and allaying excitement of the spina date seeds, the health-care food taking the two components as main active components can be developed, and the health-care food has potential application value for improving sleep and delaying senility of sub-health people, particularly middle-aged and old people.
For the separation and purification preparation of the spina date seed monomer, the method mainly comprises a macroporous resin method, an ultrafiltration method, a derivative preparation method, a gel chromatography method, a silica gel column chromatography, a reverse silica gel column chromatography method, a high performance liquid chromatography and the like, and substances prepared by the macroporous resin method, the ultrafiltration method, the derivative preparation method, the gel chromatography method, the silica gel column chromatography and the reverse silica gel column chromatography method have lower purity and can not meet the requirement of a high-purity product; high performance liquid chromatography gives high purity, but high cost, and yields of monomer components are low due to irreversible adsorption on the column.
The High Speed Counter-current Chromatography (High Speed Counter-current Chromatography) technology was developed in the last 80 th century as a liquid-liquid separation technology. Reports of using a solvent system of ethyl acetate-n-butanol-water (3:2:5) to separate the carbon glycoside of the spina date seed flavone are introduced in journal literature, "research progress of using high-speed counter-current chromatography to separate components in natural products", by Shanghan hong et al, the system can not prepare the high-purity saponin and the wensaining II, and reports of using HSCCC to prepare the high-purity saponin and the wensaining II in the spina date seed are not found in the prior art.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a method for preparing high-purity saponin and wensaining II in wild jujube kernel by adopting HSCCC.
One scheme of the invention provides a method for preparing high-purity saponin and wensaining II in spina date seeds by adopting HSCCC, which comprises the following steps:
(1) preparation of the extract: dissolving semen Ziziphi Spinosae in alcohol solution, soaking, extracting with ultrasonic wave, extracting the extractive solution with n-butanol, concentrating n-butanol layer, and drying to obtain total flavone crude product;
(2) HSCCC separation preparation: and (3) separating and purifying the crude product of the general flavone by using a HSCCC method and adopting a first solution system and a second solution system to prepare the saponin and the wensaining II.
In a further improved scheme, the first set of solution system and the second set of solution system are respectively composed of C with the volume ratio of 1-5:1-20:1-5:1-206～C8Alkyl-acetate-organic solvent with polarity of 6.0-6.6-water;
in a further improved scheme, the first set of solution system consists of C with the volume ratio of 1:3-10:1:3-106～C8Alkyl-acetate-organic solvent with polarity of 6.0-6.6-water.
In a further improved scheme, the second set of solution system consists of C with the volume ratio of 1:3-10:1:3-106～C8Alkyl-acetate-organic solvent with polarity of 6.0-6.6-water.
In a further improved scheme, the C6～C8The alkane is selected from one of n-hexane, n-heptane or n-octane; preferably n-heptane or n-hexane.
In a further improvement, the acetate is selected from ethyl acetate or propyl acetate; ethyl acetate is preferred.
In a further improved scheme, the organic solvent with the polarity of 6.0-6.6 is selected from one of methanol or acetonitrile; methanol is preferred.
In a further improved scheme, the method for preparing the crude product of the general flavone comprises the following steps of dissolving the spina date seeds in an alcohol solution, soaking, carrying out ultrasonic extraction, degreasing an extracting solution, concentrating and drying to obtain the crude product of the general flavone:
(11) pulverizing semen Ziziphi Spinosae, sieving, adding 50% -80% ethanol water solution, soaking;
(12) ultrasonic extraction: extracting at 30-50 ℃ and 500-1000W ultrasonic power for 1-5 h;
(13) concentrating the extractive solution to dryness, adding water, extracting with n-butanol, collecting n-butanol layer, concentrating, and drying to obtain crude product of total flavonoids.
In a further improved scheme, the method for preparing the saponin and the wensaing II by separating and purifying the crude product of the total flavonoids by using a HSCCC method and a first set of solution system and a second set of solution system comprises the following steps:
preparing a first solution system according to the proportion, fully oscillating and layering, wherein the upper layer is an upper layer, and the lower layer is a lower layer; dissolving the crude product of the general flavone by using an upper phase and a lower phase with a volume ratio of 1:1, filtering, injecting a sample, and performing HSCCC separation, wherein the upper phase is a stationary phase, the lower phase is a mobile phase, the rotating speed of a high-speed countercurrent chromatography host is 800-840rpm, the flow rate of the stationary phase is 10-15mL/min, the flow rate of the mobile phase is 2-2.4mL/min, the separation temperature is 20-25 ℃, collecting a fraction containing the saponin and the West Ning II, and concentrating to obtain a crude fraction;
preparing a second solution system according to the proportion, fully oscillating and layering, wherein the upper layer is an upper layer, and the lower layer is a lower layer; dissolving the crude fraction with an upper phase and a lower phase in a volume ratio of 1:1, filtering, injecting a sample, and performing HSCCC separation, wherein the upper phase is a stationary phase, the lower phase is a mobile phase, the rotating speed of a high-speed countercurrent chromatography host is 800-840rpm, the flow rate of the stationary phase is 10-15mL/min, the flow rate of the mobile phase is 2-2.4mL/min, the separation temperature is 20-25 ℃, collecting fractions containing the saponin and the wensaining II respectively, concentrating, and freeze-drying to prepare the saponin and the wensaining II.
Wherein the detection wavelength is selected to be different according to different instruments.
The method for preparing the high-purity saponin and the wensaing II in the spina date seed by adopting the HSCCC provided by the invention makes up the blank of preparing the high-purity saponin and the wensaing II in the spina date seed by utilizing the HSCCC, and the prepared saponin and the wensaing II are high in purity.
Detailed Description
Example 1
The method for preparing high-purity saponin and wensaining II in the spina date seed by adopting HSCCC comprises the following steps:
(1) preparation of the extract: dissolving semen Ziziphi Spinosae in alcohol solution, soaking, ultrasonic extracting, defatting the extractive solution, concentrating, and vacuum drying to obtain total flavone crude product;
wherein, step (1) specifically includes:
(11) pulverizing semen Ziziphi Spinosae, sieving with 40 mesh sieve, adding 70% ethanol water solution, and soaking;
(12) ultrasonic extraction: wild jujube seed powder and 70% ethanol aqueous solution in a weight ratio of 15: 1, extracting for 2 hours at 40 ℃ and 750W ultrasonic power;
(13) concentrating the extractive solution to dryness, adding water, extracting with n-butanol, collecting n-butanol layer, concentrating, and drying to obtain crude product of total flavonoids;
(2) HSCCC separation preparation: separating and purifying the crude product of the general flavone by using a HSCCC method and a first set of solution system and a second set of solution system to prepare saponin and wensaining II;
wherein, the step (2) specifically comprises the following steps:
(21) preparing a solution system from n-heptane, ethyl acetate, methanol and water according to a volume ratio of 1:5:1:5, and fully oscillating for layering, wherein the upper layer is an upper phase and the lower layer is a lower phase; dissolving the crude product of the total flavonoids by using an upper phase and a lower phase in a volume ratio of 1:1, filtering, injecting a sample, and performing HSCCC separation, wherein the upper phase is a stationary phase, the lower phase is a mobile phase, and the rotating speed of a high-speed counter-current chromatography host is 800 rpm; the flow rate of the stationary phase is 15mL/min, the flow rate of the mobile phase is 2mL/min, the separation temperature is 20 ℃, the ultraviolet detection wavelength is 335nm, fractions containing saponin and the wensaining II are collected and concentrated to obtain a crude fraction;
(22) preparing a solution system from n-heptane, ethyl acetate, methanol and water according to a volume ratio of 1:4:1:4, fully oscillating and layering, wherein the upper layer is an upper phase, and the lower layer is a lower phase; dissolving the crude total flavone product with an upper phase and a lower phase in a volume ratio of 1:1, filtering, injecting a sample, and performing HSCCC separation, wherein the upper phase is a stationary phase, and the lower phase is a mobile phase, and the rotating speed of a high-speed counter-current chromatography host machine is 800 rpm; the flow rate of the fixed phase is 15mL/min, the flow rate of the mobile phase is 2mL/min, the separation temperature is 20 ℃, the ultraviolet detection wavelength is 335nm, the fractions of the saponin and the wensaining II are respectively collected, concentrated and freeze-dried to prepare the saponin with the purity of 99.0 percent and the wensaining II with the purity of 97.7 percent.
Example 2
The method for preparing high-purity saponin and wensaining II in the spina date seed by adopting HSCCC comprises the following steps:
(1) preparation of the extract: dissolving semen Ziziphi Spinosae in alcohol solution, soaking, ultrasonic extracting, defatting the extractive solution, concentrating, and vacuum drying to obtain total flavone crude product;
wherein, step (1) specifically includes:
(11) pulverizing semen Ziziphi Spinosae, sieving with 30 mesh sieve, adding 50% ethanol water solution, and soaking;
(12) ultrasonic extraction: mixing semen Ziziphi Spinosae powder and 70% ethanol water solution at a ratio of 20:1, extracting for 4 hours at 30 ℃ and 500W ultrasonic power;
(13) concentrating the extractive solution to dryness, adding water, extracting with n-butanol, collecting n-butanol layer, concentrating, and drying to obtain crude product of total flavonoids;
(2) HSCCC separation preparation: separating and purifying the crude product of the general flavone by using a HSCCC method and a first set of solution system and a second set of solution system to prepare saponin and wensaining II;
wherein, the step (2) specifically comprises the following steps:
(21) preparing a solution system from n-heptane, ethyl acetate, methanol and water according to a volume ratio of 1:4:1:4, fully oscillating and layering, wherein the upper layer is an upper phase, and the lower layer is a lower phase; dissolving the crude product of the total flavonoids by using an upper phase and a lower phase in a volume ratio of 1:1, wherein the rotating speed of a high-speed counter-current chromatography host is 840rpm, the flow rate of a stationary phase is 10mL/min, the flow rate of a mobile phase is 2.4mL/min, the separation temperature is 25 ℃, the ultraviolet detection wavelength is 335nm, collecting fractions containing saponin and a wensaining II, and concentrating to obtain a crude fraction;
(22) preparing a solution system from n-heptane, ethyl acetate, methanol and water according to a volume ratio of 1:8:1:8, fully oscillating and layering, wherein the upper layer is an upper phase and the lower layer is a lower phase; dissolving the crude components by using an upper phase and a lower phase in a volume ratio of 1:1, filtering, injecting a sample, and performing HSCCC separation, wherein the upper phase is a stationary phase, the lower phase is a mobile phase, the rotating speed of a high-speed counter-current chromatography host is 840rpm, the flow rate of the stationary phase is 10mL/min, the flow rate of the mobile phase is 2.4mL/min, the separation temperature is 25 ℃, the ultraviolet detection wavelength is 335nm, collecting fractions of the saponin and the wensaining II respectively, concentrating, and freeze-drying to prepare the saponin with the purity of 96.5% and the wensaining II with the purity of 98.1%.
Example 3
The method for preparing high-purity saponin and wensaining II in the spina date seed by adopting HSCCC comprises the following steps:
(1) preparation of the extract: dissolving semen Ziziphi Spinosae in alcohol solution, soaking, ultrasonic extracting, defatting the extractive solution, concentrating, and vacuum drying to obtain total flavone crude product;
wherein, step (1) specifically includes:
(11) pulverizing semen Ziziphi Spinosae, sieving with 50 mesh sieve, adding 80% ethanol water solution, and soaking;
(12) ultrasonic extraction: mixing semen Ziziphi Spinosae powder and 70% ethanol water solution at a ratio of 10:1, extracting for 1h at 50 ℃ and 1000W ultrasonic power;
(13) concentrating the extractive solution to dryness, adding water, extracting with n-butanol, collecting n-butanol layer, concentrating, and drying to obtain crude product of total flavonoids;
(2) HSCCC separation preparation: separating and purifying the crude product of the general flavone by using a HSCCC method and a first set of solution system and a second set of solution system to prepare saponin and wensaining II;
wherein, the step (2) specifically comprises the following steps:
(21) preparing a solution system from n-heptane, ethyl acetate, methanol and water according to a volume ratio of 1:8:1:8, fully oscillating and layering, wherein the upper layer is an upper phase and the lower layer is a lower phase; dissolving the crude total flavone with an upper phase and a lower phase in a volume ratio of 1:1, filtering, injecting a sample, performing HSCCC separation, wherein the upper phase is a stationary phase, the lower phase is a mobile phase, the rotating speed of a high-speed counter-current chromatography host is 820rpm, the flow rate of the stationary phase is 12mL/min, the flow rate of the mobile phase is 2.2mL/min, the separation temperature is 23 ℃, the ultraviolet detection wavelength is 335nm, collecting fractions containing saponin and Wenxinin II, and concentrating to obtain a crude fraction;
(22) preparing a solution system from n-heptane, ethyl acetate, methanol and water according to a volume ratio of 1:6:1:6, and fully oscillating for layering, wherein the upper layer is an upper phase and the lower layer is a lower phase; dissolving the crude components by using an upper phase and a lower phase in a volume ratio of 1:1, filtering, injecting a sample, and performing HSCCC separation, wherein the upper phase is a stationary phase, the lower phase is a mobile phase, the rotating speed of a high-speed counter-current chromatography host is 820rpm, the flow rate of the stationary phase is 12mL/min, the flow rate of the mobile phase is 2.2mL/min, the separation temperature is 23 ℃, the ultraviolet detection wavelength is 335nm, collecting fractions of the saponin and the wensaining II respectively, concentrating, and freeze-drying to prepare the saponin with the purity of 97.1% and the wensaining II with the purity of 96.3%.
Example 4-example 14 differs from example 1 in the difference of the solvent systems of step 21) and step 22), and the results of examining the influence of the solvent systems on the purity of saponin and wencornin ii are shown in table 1.
TABLE 1 results of the Effect of different solvent systems on the purity (%) of saponin and Wenzenin II
As can be seen from the above table, the two sets of solution systems defined in this application were chosen to obtain high purity saponin and wencetin ii by the HSCCC process.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes, which are made by the present specification, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (1)
1. A method for preparing high-purity wensaining II in spina date seeds by adopting HSCCC is characterized by comprising the following steps:
(1) preparation of the extract: dissolving semen Ziziphi Spinosae in alcohol solution, soaking, extracting with ultrasonic wave, extracting the extractive solution with n-butanol, concentrating n-butanol layer, and drying to obtain total flavone crude product;
(2) HSCCC separation preparation: separating and purifying the crude product of the general flavone by using a HSCCC method and a first set of solution system and a second set of solution system to prepare the Wenxinin II; the first solution system consists of C6-C8 alkane-acetate with the volume ratio of 1:3-10:1:3-10, an organic solvent with the polarity of 6.0-6.6 and water; the second solution system consists of C6-C8 alkyl-acetate with the volume ratio of 1:3-10:1:3-10, organic solvent with the polarity of 6.0-6.6 and water;
the C6-C8 alkane is selected from n-heptane or n-hexane;
the acetate is selected from ethyl acetate;
the organic solvent with the polarity of 6.0-6.6 is methanol.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH09328496A (en) * | 1996-06-07 | 1997-12-22 | Kao Corp | Separation and concentration of ziziphin |
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