CN108558970B - Method for simultaneously preparing high-purity morroniside and loganin from dogwood extract - Google Patents
Method for simultaneously preparing high-purity morroniside and loganin from dogwood extract Download PDFInfo
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Abstract
The invention relates to a method for simultaneously preparing high-purity morroniside and loganin from a dogwood extract. After macroporous adsorption resin enrichment and normal phase silica gel preliminary separation, the dogwood extract passes through a medium-pressure reverse phase silica gel chromatographic column, the mobile phase is ethanol and water, gradient elution is carried out, the same components are combined, and the reduced pressure concentration is carried out to respectively obtain a crude morroniside product and a crude loganin product with the purity being equal to or larger than 90 percent; purifying by Sephadex LH-20 gel column, eluting with mixed solvent of chloroform and methanol, mixing the same components, and evaporating under reduced pressure to obtain high-purity morroniside and loganin. The method is simple and easy to operate, mild in conditions and suitable for simultaneously preparing the cornus officinalis extract in a large scale and producing the morroniside and the loganin with the purity being equal to or larger than 98%.
Description
Technical Field
The invention relates to a method for simultaneously preparing high-purity morroniside and loganin from a dogwood extract, in particular to a separation method for preparing a high-purity target compound by combining medium-pressure reverse-phase silica gel column chromatography with Sephadex LH-20 (hydroxypropyl Sephadex) gel column chromatography, wherein the medium-pressure reverse-phase silica gel column chromatography has a remarkable separation effect on morroniside and loganin.
Background
The dogwood is Cornus officinalis Sieb.Et Zucc of Cornus officinalis of Cornaceae, the medicinal part of the dogwood is dry and mature pulp, the dogwood has the effects of tonifying liver and kidney, astringing and relieving depletion, and the dogwood is widely applied to treatment of dizziness and tinnitus, soreness and pain of waist and knees, impotence and spermatorrhea, internal heat and thirst quenching and the like. The dogwood has a plurality of chemical components, iridoid glycoside is the main active component, while morroniside and loganin are two components with the largest content in iridoid total glycoside, and are also the main active components, and have better effects on cardiovascular protection, neuroprotection, anti-tumor and the like. A simple and feasible method for simultaneously preparing high-purity active monomer compounds from dogwoods is found, and a good foundation is laid for development and utilization of the dogwoods.
The method for simultaneously preparing the morroniside and the loganin from the dogwood is less, and the patent CN 102477053A reports that the morroniside and the loganin are simultaneously separated by adopting high-speed counter-current chromatography, the method needs special equipment, has higher cost, is not suitable for preparing a large amount of products, adopts a recrystallization mode for purification, wastes time and labor, and has limited amount of high-purity target compounds; "preparation of Strychnos nux-vomica glycoside and Monuo glycoside in Cornus officinalis" (Lexiana, preparation of Strychnos nux-vomica glycoside and Monuo glycoside in Cornus officinalis. Chinese herbal medicine 2006,37(8): 1168-.
Disclosure of Invention
The invention aims to overcome the defects of simultaneously preparing and purifying the morroniside and the loganin in the existing preparation method and technology, and provides a method which is simple in preparation method, easy to operate, high in yield, suitable for large-scale production and simultaneously preparing the high-purity morroniside and the loganin. The method is simple and feasible, and the morroniside and the loganin with the purity being equal to or larger than 98 percent (mass percent, the same below) can be simultaneously prepared in a large scale.
A method for preparing high-purity morroniside and loganin simultaneously from a dogwood extract comprises the following steps after the dogwood extract is enriched by macroporous adsorption resin and is primarily separated by normal phase silica gel:
(1) medium-pressure reverse-phase silica gel column separation: dissolving a mixed sample containing the morroniside and the loganin, which is obtained by enrichment through macroporous adsorption resin and primary separation through normal phase silica gel, with water, performing gradient elution through a medium-pressure reverse phase silica gel chromatographic column with ethanol and water as mobile phases, respectively collecting eluates rich in the morroniside and the loganin, and performing reduced pressure concentration to obtain a crude product of the morroniside and a crude product of the loganin with the purity not less than 90%;
(2) purifying by using a gel column: and (3) respectively purifying the crude products of the morroniside and the loganin with the purity ≧ 90% by a Sephadex LH-20 gel (hydroxypropyl Sephadex) column, eluting by a chloroform and methanol mixed solvent, and evaporating the eluent under reduced pressure to dryness to obtain the high-purity morroniside and loganin.
In the step (1), a medium-pressure reverse phase silica gel separation instrument is a medium-pressure chromatograph, the pressure is between 0 and 50MPa, and the pressure is between 5 and 25MPa when the medium-pressure reverse phase silica gel separation instrument is used; separating with medium-pressure reverse phase silica gel column chromatography, wherein the column chromatography is reverse phase silica gel column, and the reverse phase silica gel filler is C18 filler.
When the medium-pressure reverse-phase silica gel is separated, performing wet loading on the medium-pressure reverse-phase silica gel column chromatography, performing gradient elution on a mobile phase which is a mixed solvent of ethanol and water at a volume ratio of 5: 95-20: 80, collecting fractions of ethanol and water at a volume ratio of 5: 95-8: 92, combining the same components according to silica gel thin-layer chromatography and high-performance liquid chromatography, and performing reduced-pressure concentration to obtain a crude product of the morroniside with the purity not less than 90%; collecting the flow parts of ethanol and water with the volume ratio of 10: 90-20: 80, combining the same components according to silica gel thin-layer chromatography and high performance liquid chromatography, and concentrating under reduced pressure to obtain a crude loganin product with the purity being not less than 90%. The purity of the crude product of the mogroside and the loganin obtained by medium-pressure reverse phase column chromatography (wet loading) is not less than 98 percent, and the purity of the vast majority of the samples is not less than 90 percent.
Preferably, the solvent elution flow rate is 10-50ml/min, and each gradient elutes 3-5 column volumes. The volume ratio of the ethanol to the water of the mobile phase is 5:95, 7:93, 8:92, 10:90, 12:88, 15:85, 20:80 gradient elution is carried out.
In the step (2), when Sephadex LH-20 gel column chromatography is adopted for purification, the mobile phase is chloroform and methanol, and the volume ratio of the chloroform to the methanol can be any ratio of 0: 1-2.5: 1, namely the volume ratio of the chloroform to the methanol is 0:1, 0.5:1, 1:1, 1.5:1, 2:1, 2.5:1 or any ratio therebetween as the solvent.
Preferably, when the crude morroniside product is purified by using Spehadex LH-20 gel, the mobile phase is eluted by using chloroform and methanol at the volume ratio of 1.5: 1; when the crude loganin is purified by Spehadex LH-20 gel, the mobile phase is eluted by chloroform to methanol in a volume ratio of 2.5: 1.
The Sephadex LH-20 gel column chromatography is controlled at the flow rate of 2-20 ml/min according to the diameter and length of the column.
After elution, the same components are combined according to a silica gel thin-layer chromatography and a high performance liquid chromatography, and the purity of the morroniside obtained by reduced pressure evaporation is larger than or equal to 98 percent, and the purity of the loganin is larger than or equal to 98 percent.
In the invention, the preparation method of the dogwood extract comprises the following steps: pulverizing dried Corni fructus, sieving with 20 mesh sieve, adding 50% ethanol into the powder at a liquid-material ratio of 10:1(ml/g), ultrasonic extracting for three times, mixing extractive solutions, concentrating under reduced pressure, and evaporating to dryness to obtain Corni fructus extract powder. The process conditions of ultrasonic extraction are as follows: the extraction is carried out at room temperature, the power of ultrasonic wave is 300W, and the extraction time is 45-60 min each time.
Enriching by macroporous adsorption resin: dissolving Corni fructus extract with water, subjecting to macroporous adsorbent resin column with water and/or ethanol as mobile phase, performing gradient elution, collecting eluate rich in morroniside and loganin, and recovering under reduced pressure to obtain dried eluate.
Preferably, the macroporous adsorbent resin is enriched by dissolving Corni fructus extract with water, filtering, removing insoluble substances, subjecting the liquid to HP-20 type macroporous adsorbent resin column, gradient eluting with water, 10% ethanol (volume%, the same below), 40% ethanol, 70% ethanol, and 95% ethanol, respectively, collecting 40% ethanol eluate, and recovering under reduced pressure to obtain dried eluate. Preferably, the solvent elution flow rate is 10-50ml/min, and each gradient elutes 3-5 column volumes.
Primary separation of a normal phase silica gel column: dissolving the obtained eluate, mixing with normal phase silica gel, mixing with silica gel, loading with mobile phase of chloroform and methanol by dry method, performing gradient elution, collecting eluate rich in morroniside and loganin, and concentrating under reduced pressure to obtain mixed sample containing morroniside and loganin.
Preferably, the normal phase silica gel column is initially separated, after the obtained eluate is dissolved by methanol, the normal phase silica gel is mixed with a sample, the mixed silica gel is loaded by a dry method, and the mobile phase is chloroform: performing gradient elution with methanol at 15: 1-8: 1, combining chloroform: and (3) concentrating the same components with methanol being 10: 1-8: 1 under reduced pressure to obtain a mixed sample containing the morroniside and the loganin, wherein the normal phase silica gel is 160-200 meshes. Preferably, the solvent elution flow rate is 10-50ml/min, and each gradient elutes 2-5 column volumes. The mobile phase is eluted according to the gradient that the volume ratio of chloroform to methanol is 15:1, 12:1, 10:1, 9:1 and 8:1 respectively.
Detecting the obtained monomer morroniside and loganin by high performance liquid chromatography to finally determine the purity of the morroniside and loganin. The HPLC analysis method related to the invention is characterized in that the liquid chromatograph is a Waters2545 model 2998 detector, the chromatographic Column is a Waters sunfire C18Column (4.6 × 250mm, 5 μm), and the mobile phase: methanol: water 30:70, flow rate: 1mL/min, detection wavelength: 240 nm.
The morroniside and the loganin have obvious separation effect on medium-pressure reverse phase silica gel column chromatography, can be completely separated at one time, and has high speed and high efficiency. The mobile phase used by gel Sephadex LH-20 is different proportions of chloroform and methanol, and the used eluent is a normal phase system, thereby ensuring the separation effect and rapid separation and recovery. The crude morroniside product and the crude loganin product with the purity of not less than 90 percent can be respectively subjected to gel column chromatography (wet loading, wet column loading, and repeated long-term use after once column loading of filler) to obtain high-purity morroniside and loganin with the purity of not less than 98 percent. The method is simple and easy to operate, has mild conditions, can repeatedly use the reverse phase silica gel column and the gel column, and is suitable for simultaneously preparing and producing the morroniside and the loganin with the purity being equal to or more than 98% in a large scale by using the dogwood extract.
The method can simultaneously obtain high-purity morroniside and loganin from the dogwood extract. According to the invention, an optimal purification process route is finally selected through multiple search attempts, and a method which is simple and easy to operate and can efficiently prepare large quantities of high-purity morroniside and loganin with the content being equal to or larger than 98% is provided for the market.
Drawings
FIG. 1 is a Monoloside purity check HPLC chromatogram.
FIG. 2 is a HPLC chromatogram for purity check of loganin.
Detailed Description
The method for simultaneously preparing high-purity morroniside and loganin from the dogwood extract comprises the following specific steps:
the method comprises the following steps: pulverizing dried fruit of Corni fructus, sieving with 20 mesh sieve, extracting with 50% ethanol at liquid-to-material ratio of 10:1(ml/g) under ultrasonic condition for three times, mixing extractive solutions, concentrating under reduced pressure, and evaporating to dryness to obtain crude extract powder of Corni fructus.
Step two: dissolving the above powder with water, filtering, removing insoluble substances, subjecting the liquid to HP-20 type macroporous adsorbent resin column, gradient eluting with water, 10% ethanol, 40% ethanol, 70% ethanol, and 95% ethanol, collecting 40% ethanol eluate, and vacuum distilling, drying and recovering to obtain dried eluate.
Step three: dissolving the eluate with methanol, mixing with normal phase silica gel, mixing with silica gel, loading, separating with normal pressure normal phase silica gel column chromatography, and separating with chloroform: performing gradient elution with methanol at 15: 1-8: 1, and collecting chloroform: and (3) carrying out fractional distillation on the methanol (10: 1-8: 1), combining the same components, and carrying out reduced pressure concentration to obtain a mixed sample containing the morroniside and the loganin, wherein the normal phase silica gel is 160-200 meshes.
Step four: dissolving a mixed sample containing the morroniside and the loganin in pure water, and putting the mixed sample on a medium-pressure reverse-phase C18 chromatographic column, wherein the mobile phase comprises the following components: ethanol: and (3) carrying out gradient elution with water at the ratio of 5: 95-20: 80, and collecting ethanol: mixing the same components to obtain the morroniside with the purity being equal to or larger than 90 percent; collecting ethanol: and (3) mixing the same components to obtain the loganin with the purity being equal to or larger than 90% by using the flow part of 10: 90-20: 80.
Step five: the crude products of the morroniside and the loganin with the purity being equal to or larger than 90 percent are respectively purified by Spehadex LH-20 gel, and the mobile phases are respectively purified by chloroform: eluting with methanol at a ratio of 1.5:1 and 2.5:1, mixing the same components, and evaporating under reduced pressure to obtain > 98% high purity morroniside and loganin. Detecting the obtained monomer with high performance liquid chromatography to determine the purity of the morroniside and the loganin.
In the invention, the concentration of ethanol refers to volume concentration, the proportion of solvents in a mixed solvent refers to volume ratio, and the purity of the morroniside and the nux vomica glycoside is the mass percent purity.
Example 1 extraction of fruit of Cornus officinalis
Pulverizing dried Corni fructus 10kg, sieving with 20 mesh sieve, extracting with 50% ethanol solution at a ratio of 10:1 under ultrasonic condition with ultrasonic power of 300W for 60min for three times, mixing extractive solutions, concentrating under reduced pressure, and drying to obtain Corni fructus extract.
EXAMPLE 2 preparation of high purity morroniside and Strychnos Nudiflorin
1) Enrichment with macroporous adsorbent resin
Dissolving Corni fructus extract in water, and filtering to obtain filtrate. And (3) loading the filtrate into an HP-20 type macroporous adsorption resin column by a wet method, after completely adsorbing the sample, sequentially carrying out gradient elution by using pure water, 10 percent, 40 percent, 70 percent and 95 percent ethanol, and collecting the eluent. The flow rate was 40ml/min and 3 column volumes were eluted per gradient. According to detection of thin layer and high performance liquid chromatography, the target is completely enriched at 40% ethanol elution part, and the 40% ethanol elution part is concentrated under reduced pressure and dried.
2) Normal phase silica gel column separation
Taking 500g of the dried substance, dissolving the dried substance by 5000ml of methanol, and mixing the sample by normal phase silica gel (160-; separating by normal pressure silica gel column chromatography, loading 5000g normal phase silica gel (160-200 mesh) on the column by dry method, and separating the mobile phase by chloroform: and (3) carrying out gradient elution according to the volume ratio of chloroform to methanol of 15:1, 12:1, 10:1, 9:1 and 8:1 respectively, wherein the flow rate is 30ml/min, and 3 column volumes are eluted in each gradient. And (3) respectively collecting chloroform: carrying out fractional distillation on methanol at a ratio of 10: 1-8: 1, and combining the same components; recovering under reduced pressure to obtain a mixed sample containing morroniside and loganin.
3) Medium pressure reverse phase silica gel column separation
Dissolving 100g of the mixed sample containing the morroniside and the loganin in the step 2) with pure water, filtering, subjecting the filtrate to medium pressure (pressure is 0-50MPa, and pressure is 5-25MPa in use) reverse phase silica gel C18column (filler C18, filling amount is 1200g), and subjecting the mobile phase to: ethanol: water 5:95 to 20:80, 5:95, 7:93, 8:92, 10:90, 12: 88. gradient elution was performed at 15:85, 20:80, flow rate: 30ml/min, eluting 4 column volumes per gradient; collecting ethanol: separating with water at a ratio of 5: 95-8: 92, combining the same components according to silica gel thin-layer chromatography and high performance liquid chromatography, and concentrating and drying under reduced pressure to obtain a crude morroniside product with purity not less than 90%; collecting ethanol: and (3) dividing the mixture into 10: 90-20: 80 fractions, combining the same components according to silica gel thin-layer chromatography and high performance liquid chromatography, and concentrating and drying under reduced pressure to obtain the crude loganin with purity being not less than 90%. The medium-pressure reverse-phase silica gel column can be repeatedly used after being filled once, and has the advantages of high elution speed, short time and high efficiency.
4) Gel column purification
Respectively taking the morroniside and loganin samples with the purity not less than 90% in the step 3), respectively dissolving with pure water, purifying with Sephadex LH-20 gel, and respectively using chloroform as a mobile phase: eluting with methanol at flow rate of 6ml/min at 1.5:1 and 2.5:1, mixing the same components according to silica gel thin layer chromatography and high performance liquid chromatography, and evaporating under reduced pressure to obtain > 98% high purity mogroside and loganin. The gel column can be used repeatedly, the mobile phase is a normal phase system, the column chromatography time is short, and the separation and recovery efficiency is high.
Example 3 HPLC detection method
Liquid chromatograph: waters2545 model 2998 model ultraviolet detector
Chromatographic Column Waters sunfire C18Column (4.6X 250mm, 5 μm)
Mobile phase: methanol: water 30:70
Flow rate: 1mL/min
Detection wavelength: 240nm
Sample size of 10. mu.l
The peak time: the morroniside content is 9.22min, and the nux vomica glycoside content is 20.92min
Preparing solution of a test sample and a reference sample: chromatographic grade methanol was dissolved.
By adopting the apparatus and the method, the morroniside and the loganin obtained in example 2 are detected, the purity check HPLC chromatograms of the morroniside and the loganin are respectively shown in fig. 1 and fig. 2, and are determined as morroniside and loganin monomers through comparison with a reference substance chromatogram, and the purity is equal to or greater than 98%.
The invention primarily separates the dogwood extract by macroporous adsorption resin and normal phase silica gel, and then separates by a reverse phase column of a medium pressure chromatograph, wherein the mobile phase is ethanol: gradient elution is carried out on water at the ratio of 5: 95-20: 80, the same components are combined, and the mixture is concentrated under reduced pressure to obtain crude products of the morroniside and the loganin with the purity of not less than 90%; finally, purifying by Sephadex LH-20 gel column chromatography respectively, wherein the mobile phase comprises the following components: chloroform: eluting with methanol at ratio of 1.5:1 and 2.5:1 respectively, mixing the same components, and evaporating under reduced pressure to obtain morroniside and loganin with purity of above 98%. The morroniside and the loganin have obvious separation effect on medium-pressure reverse phase silica gel column chromatography, can be completely separated at one time, and has high speed and high efficiency. The method is simple and easy to operate, mild in conditions and suitable for simultaneously preparing the cornus officinalis extract in a large scale and producing the morroniside and the loganin with the purity being equal to or larger than 98%.
Claims (3)
1. A method for preparing high-purity morroniside and loganin simultaneously from a dogwood extract comprises the following steps after the dogwood extract is enriched by macroporous adsorption resin and is primarily separated by normal phase silica gel:
(1) medium-pressure reversed-phase silica gel separation: dissolving a mixed sample containing the morroniside and the loganin, which is obtained by macroporous adsorption resin enrichment and normal phase silica gel preliminary separation, with water, loading the sample by a medium-pressure reverse phase silica gel chromatographic column by adopting a wet method, wherein a mobile phase is a mixed solvent of ethanol and water, the volume ratio of the ethanol to the water is 5: 95-20: 80, after gradient elution, collecting fractions of the ethanol to the water with the volume ratio of 5: 95-8: 92, combining the same components, and concentrating under reduced pressure to obtain a morroniside crude product; collecting the parts of ethanol and water with the volume ratio of 10: 90-20: 80, mixing the same components, and concentrating under reduced pressure to obtain a crude product of the loganin;
(2) purifying by using a gel column: purifying the crude morroniside product and the crude loganin product by Sephadex LH-20 gel column respectively, eluting by using a mixed solvent of chloroform and methanol at the flow rate of 2-20 ml/min, and evaporating under reduced pressure to obtain high-purity morroniside and loganin; when the crude morroniside product is purified by Sephadex LH-20 gel, the volume ratio of chloroform to methanol used for a mobile phase is 1.5: 1; when the crude loganin is purified by Sephadex LH-20 gel, the volume ratio of chloroform to methanol used for a mobile phase is 2.5: 1; the purity of the obtained morroniside is not less than 98% by mass, and the purity of loganin is not less than 98% by mass.
2. The method for simultaneously preparing high-purity morroniside and loganin from the dogwood extract according to claim 1, wherein the method comprises the following steps: the medium-pressure reverse phase silica gel separation instrument is a medium-pressure chromatograph, and the reverse phase silica gel column adopts a reverse phase silica gel filler C18 filler.
3. The method for simultaneously preparing high-purity morroniside and loganin from the dogwood extract according to claim 1, wherein the method comprises the following steps: the preparation method of the dogwood extract comprises the following steps: pulverizing dried Corni fructus, sieving with 20 mesh sieve, adding 50% ethanol into the powder, performing ultrasonic extraction at liquid-material ratio of 10:1 ml/g for three times, mixing extractive solutions, concentrating under reduced pressure, and evaporating to dryness to obtain Corni fructus extract powder; the ultrasonic extraction is carried out at room temperature, the power of the ultrasonic wave is 300W, and the extraction time is 45-60 min each time.
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| 山茱萸果肉中化学成分研究（I）;第5期;《长治医学院学报》;20131031;第27卷;第332-334页 * |
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