CN102399252A - Preparation method for cowherb seed flavonoid glycoside monomer - Google Patents
Preparation method for cowherb seed flavonoid glycoside monomer Download PDFInfo
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- CN102399252A CN102399252A CN2011104200855A CN201110420085A CN102399252A CN 102399252 A CN102399252 A CN 102399252A CN 2011104200855 A CN2011104200855 A CN 2011104200855A CN 201110420085 A CN201110420085 A CN 201110420085A CN 102399252 A CN102399252 A CN 102399252A
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Abstract
The invention relates to a method for quickly separating a high-purity cowherb seed flavonoid glycoside monomer from a Chinese medicinal material cowherb seed and belongs to the technical field of Chinese medicines. The method comprises the following process steps of: A, extracting raw materials, namely poaching; B, enriching by using macroporous resin; C, performing high-efficiency preparation and liquid phase separation, wherein C18 fillers are adopted, the detection wavelength is 280 nm and the mobile phase is a 30 volume percent methanol solution; and D, recovering products, namely enriching a preparation solution by using the macroporous resin, desorbing by using ethanol, concentrating and drying to obtain the cowherb seed flavonoid glycoside monomer with the purity of over 99 percent. The method is simple and quick, low in solvent consumption, high in yield, and economic and environment-friendly. A large number of products can be prepared by the method at one time. The method has high economic value and academic value.
Description
Technical field
The present invention relates to the monomeric preparation method of a kind of Chemistry for Chinese Traditional Medicine, belong to technical field of traditional Chinese medicines, particularly, the present invention relates to a kind of from the Chinese medicinal materials Semen Vaccariae sharp separation high purity Semen Vaccariae flavonoid glycoside monomer methods.
Background technology
Chinese medicinal materials Semen Vaccariae (Vaccariae Semen); It is the dry mature seed of Caryophyllaceae (Caryophyllaceae) Vaccaria (Vaccaria Medic.) plant cow-fat (Vaccaria segetalis (Neck.) Garcke); Has promoting blood circulation to restore menstrual flow; The lactogenesis detumescence, the effect of inducing diuresis for treating stranguria syndrome.Be used for through closing, dysmenorrhoea, agalactia, acute mastitis swells and ache, the puckery pain of stranguria." Chinese pharmacopoeia is recorded, and is lactagogue good medicine in order to go through portion.
Semen Vaccariae flavonoid glycoside (Vaccarin); Chemistry 4H-1-Benzopyran-4-one by name; 6-(2-O-α-L-arabinopyranosyl-β-D-glucopyranosyl)-2-[4-(phenyl of β-D-glucopyranosyloxy)]-5,7-dihydroxy-, molecular formula is C
32H
38O
19, structural formula is following:
The Semen Vaccariae flavonoid glycoside is the main active ingredient of Semen Vaccariae, also is characteristic chemical constituent, is used for the quality control of Semen Vaccariae medicinal material.At present seldom about the bibliographical information of Semen Vaccariae flavonoid glycoside separation and purification; The Meng, report such as he, Qin Wenjie utilized silica gel column chromatography to combine dextran gel column chromatography to separate, and can obtain Semen Vaccariae flavonoid glycoside crystalline particulate (" herbal medicine " in May, 2011).Through repeatedly practising, Semen Vaccariae flavonoid glycoside water-soluble very strong is difficult for silica gel column chromatography and separates and crystallization purifying, thereby be difficult to obtain its high-purity monomer.The author finds to adopt the preparative high performance liquid chromatography post to separate through a large amount of practices of groping, and through once preparation, product purity can reach more than 99%.High performance preparative liquid chromatography is used for the monomeric separation and purification of Semen Vaccariae flavonoid glycoside and belongs to reported first.
Summary of the invention
The present invention is intended to overcome the defective of prior art, provide a kind of from the Semen Vaccariae medicinal material method of separating high-purity Semen Vaccariae flavonoid glycoside.Should method is simple, consume that solvent is few, yield is high, safety non-toxic, environmental protection, and product purity can reach more than 99%, can satisfy scale operation and suitability for industrialized production needs fully.
For realizing the foregoing invention purpose, the technical scheme that the present invention adopts is following:
The monomeric preparation method of a kind of Semen Vaccariae flavonoid glycoside is characterized in that being undertaken by following process step:
A. raw material extracts: Semen Vaccariae is ground into meal, adds the water that 8-10 doubly measures according to mass volume ratio (kg/L), boil to boil to filter in 2 hours and extract, extract altogether 3 times, united extraction liquid is cooled to room temperature;
B. macroporous resin enrichment: the cooled extracting solution of steps A is adsorbed through the good AB-8 macroporous adsorptive resins of activation with the speed of 2 ~ 5BV; Then respectively with the water of 3 times of amount column volumes and the volume(tric)fraction 30% ethanolic soln wash-out impurity of 2 times of amount column volumes; Again with 2 times of volume(tric)fraction 50% ethanolic soln wash-out target substances of measuring column volumes; Collect elutriant, be concentrated into 1/10 of original volume;
C. efficient production liquid phase separation: behind the filtering with microporous membrane of step B gained enriching soln with the 0.45um aperture; Obtain the Semen Vaccariae flavonoid glycoside through the separation of high performance preparative liquid chromatography post again and prepare solution, get the Semen Vaccariae flavonoid glycoside aqueous solution behind the recovery organic solvent;
D. product reclaims: the step C gained Semen Vaccariae flavonoid glycoside aqueous solution is adsorbed through the good AB-8 macroporous adsorptive resins of activation with the speed of 2 ~ 5BV; Then with 2 times of volume(tric)fraction 95% ethanol elutions of measuring column volumes; Concentrate eluant is to doing; Solid got Semen Vaccariae flavonoid glycoside monomer product in 80 ℃ times dry 6 hours.
Said high performance preparative liquid chromatography column packing is octadecylsilane chemically bonded silica (C18), and the post specification is 50cm * 10cm, 50cm * 8cm or 50cm * 5cm etc.
The chromatographic condition of said efficient production liquid phase is: detect wavelength 280nm, moving phase is methanol-water, and its volume ratio is 3:7.
The invention has the advantages that:
1, step is few, weak point consuming time, and yield is high, and is easy and simple to handle, is easy to suitability for industrialized production.
2, solvent consumption is few, and the solvent in the preparative liquid chromatography separating step is all recyclable to be utilized again.
3, solvent toxicity is little, used organic solvent methyl alcohol, ethanol etc., and environmental pollution is little.
4, good in economic efficiency, can carry out scale operation, and operation is easy, only comprise 4 steps, be easy to control, separation efficiency is high.
5, has high academic value.At present domestic bibliographical information about the separation and purification of Semen Vaccariae flavonoid glycoside seldom, high performance preparative liquid chromatography is used for the monomeric separation and purification of Semen Vaccariae flavonoid glycoside and belongs to first.Products obtained therefrom of the present invention not only can be used as Semen Vaccariae flavonoid glycoside reference substance, also can be suitability for industrialized production Semen Vaccariae flavonoid glycoside preparation highly purified raw material is provided.
Description of drawings
Fig. 1 is the embodiment of the invention 1 a step C efficient production liquid phase separation on-line monitoring collection of illustrative plates
Fig. 2 is that the monomeric HPLC of the embodiment of the invention 1 Semen Vaccariae flavonoid glycoside detects collection of illustrative plates.
Embodiment
Embodiment 1
The monomeric preparation method of a kind of Semen Vaccariae flavonoid glycoside is characterized in that being undertaken by following process step:
A. raw material extracts: 5kg is ground into meal with the Semen Vaccariae medicinal material, adds 50L water, and heating is boiled and boiled 2 hours, filters; Add 50L water in the filter residue again, boil with method and boil 2 hours, filter; Add 50L water in the filter residue once more, boil with method and boil 2 hours, filter, merging filtrate is placed and is cooled to room temperature;
B. macroporous resin enrichment: take by weighing 2kg AB-8 macroporous adsorbent resin, load resin post, the about 6L of resin bed volume with diameter 15cm glass column; The cooled filtrating of steps A is adsorbed through the good macroporous adsorptive resins of activation with the speed of 4BV; Use 18L water and 12L volume(tric)fraction 30% ethanolic soln wash-out impurity then respectively; Use 12L volume(tric)fraction 50% ethanolic soln wash-out target substance again, collect elutriant, be concentrated into about 1L;
C. efficient production liquid phase separation: with the filtering with microporous membrane of step B gained enriching soln with the 0.45um aperture; Separate through the high performance preparative liquid chromatography post; Collect Semen Vaccariae flavonoid glycoside section and prepare solution, the preparation solution decompression that will collect then concentrate recovery methyl alcohol to do not have alcohol distinguish the flavor of the Semen Vaccariae flavonoid glycoside aqueous solution.
Said high performance preparative liquid chromatography column packing is octadecylsilane chemically bonded silica (C
18), the post specification is 50cm * 8cm; Detect wavelength 280nm, moving phase is volume(tric)fraction 30% methanol solution.
D. product reclaims: take by weighing 500g AB-8 macroporous adsorbent resin, load resin post, the about 1.5L of resin bed volume with diameter 10cm glass column; The step C gained Semen Vaccariae flavonoid glycoside aqueous solution is adsorbed through the good macroporous adsorptive resins of activation with the speed of 4BV; Use 3L volume(tric)fraction 95% ethanol elution then; Concentrate eluant is to doing, and 80 ℃ of dryings of solid 6 hours get Semen Vaccariae flavonoid glycoside monomer.
The heavy 22g of gained Semen Vaccariae flavonoid glycoside monomer, the HPLC purity check is 99.3%.
Embodiment 2
The monomeric preparation method of a kind of Semen Vaccariae flavonoid glycoside is characterized in that being undertaken by following process step:
A. raw material extracts: 10kg is ground into meal with the Semen Vaccariae medicinal material, adds 80L water, and heating is boiled and boiled 2 hours, filters; Add 80L water in the filter residue again, boil with method and boil 2 hours, filter; Add 80L water in the filter residue once more, boil with method and boil 2 hours, filter, merging filtrate is placed and is cooled to room temperature;
B. macroporous resin enrichment: take by weighing 4kg AB-8 macroporous adsorbent resin, load resin post, the about 12L of resin bed volume with diameter 20cm glass column; Cooled extracting solution is adsorbed through the good macroporous adsorptive resins of activation with the speed of 3BV; Use 36L water and 24L volume(tric)fraction 30% ethanolic soln wash-out impurity then respectively; Use 24L volume(tric)fraction 50% ethanolic soln wash-out target substance again, collect elutriant, be concentrated into about 2.5L;
C. efficient production liquid phase separation: with the filtering with microporous membrane of step B gained enriching soln with the 0.45um aperture; Separate through the high performance preparative liquid chromatography post; Collect Semen Vaccariae flavonoid glycoside section and prepare solution, the preparation solution decompression that will collect then concentrate recovery methyl alcohol to do not have alcohol distinguish the flavor of the Semen Vaccariae flavonoid glycoside aqueous solution.
Said high performance preparative liquid chromatography column packing is octadecylsilane chemically bonded silica (C
18), the post specification is 50cm * 10cm; Detect wavelength 280nm, moving phase is volume(tric)fraction 30% methanol solution.
D. product reclaims: take by weighing 1kg AB-8 macroporous adsorbent resin, load resin post, the about 3L of resin bed volume with diameter 10cm glass column; The step C gained Semen Vaccariae flavonoid glycoside aqueous solution is adsorbed through the good macroporous adsorptive resins of activation with the speed of 3BV; Use 6L volume(tric)fraction 95% ethanol elution then; Concentrate eluant is to doing, and 80 ℃ of dryings of solid 6 hours get Semen Vaccariae flavonoid glycoside monomer.
The heavy 43.5g of gained Semen Vaccariae flavonoid glycoside monomer, the HPLC purity check is 99.2%.
Claims (3)
1. monomeric preparation method of Semen Vaccariae flavonoid glycoside is characterized in that being undertaken by following process step:
A. raw material extracts: Semen Vaccariae is ground into meal, adds the water that 8-10 doubly measures according to mass volume ratio kg/L, boil to boil to filter in 2 hours and extract, extract altogether 3 times, united extraction liquid is cooled to room temperature;
B. macroporous resin enrichment: the cooled extracting solution of steps A is adsorbed through the good AB-8 macroporous adsorptive resins of activation with the speed of 2 ~ 5BV; Then respectively with the water of 3 times of amount column volumes and the volume(tric)fraction 30% ethanolic soln wash-out impurity of 2 times of amount column volumes; Again with 2 times of volume(tric)fraction 50% ethanolic soln wash-out target substances of measuring column volumes; Collect elutriant, be concentrated into 1/10 of original volume;
C. efficient production liquid phase separation: behind the filtering with microporous membrane of step B gained enriching soln with the 0.45um aperture; Obtain the Semen Vaccariae flavonoid glycoside through the separation of high performance preparative liquid chromatography post again and prepare solution, get the Semen Vaccariae flavonoid glycoside aqueous solution behind the recovery organic solvent;
D. product reclaims: the step C gained Semen Vaccariae flavonoid glycoside aqueous solution is adsorbed through the good AB-8 macroporous adsorptive resins of activation with the speed of 2 ~ 5BV; Then with 2 times of volume(tric)fraction 95% ethanol elutions of measuring column volumes; Concentrate eluant is to doing; Solid got Semen Vaccariae flavonoid glycoside monomer product in 80 ℃ times dry 6 hours.
2. according to the monomeric preparation method of the said Semen Vaccariae flavonoid glycoside of claim 1, it is characterized in that said high performance preparative liquid chromatography column packing is an octadecylsilane chemically bonded silica, the post specification is 50cm * 10cm, 50cm * 8cm or 50cm * 5cm.
3. according to the monomeric preparation method of claim 1 Semen Vaccariae flavonoid glycoside, it is characterized in that the chromatographic condition of said efficient production liquid phase is: detect wavelength 280nm, moving phase is methanol-water, and its volume ratio is 3:7.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103102376A (en) * | 2012-12-05 | 2013-05-15 | 江南大学 | Separation method for simultaneously separating cowherb seed flavonoid glycoside and cowherb seed total saponin |
| CN103304611A (en) * | 2013-06-18 | 2013-09-18 | 聊城大学 | Method for separating and purifying three flavonoid glycosides from trichosanthes bark |
| CN109632994A (en) * | 2018-12-21 | 2019-04-16 | 广东方制药有限公司 | The method for building up of the UPLC map of the seed of cowherb and Semen Vaccariae (parched) and application |
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| WO2009089631A1 (en) * | 2008-01-18 | 2009-07-23 | National Research Council Of Canada | Process for seed and grain fractionation and recovery of bio-products |
| CN101723998A (en) * | 2008-10-17 | 2010-06-09 | 中国科学院大连化学物理研究所 | Preparation method of flavonoid glycosides in scutellaria baicalensis |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103102376A (en) * | 2012-12-05 | 2013-05-15 | 江南大学 | Separation method for simultaneously separating cowherb seed flavonoid glycoside and cowherb seed total saponin |
| CN103102376B (en) * | 2012-12-05 | 2016-08-31 | 江南大学 | A kind of separation method concurrently separating Vaccarin and Semen Vaccariae total saponins |
| CN103304611A (en) * | 2013-06-18 | 2013-09-18 | 聊城大学 | Method for separating and purifying three flavonoid glycosides from trichosanthes bark |
| CN103304611B (en) * | 2013-06-18 | 2016-06-15 | 山东中医药大学 | A kind of method of separation and purification 3 kinds of flavonoid glycosides from Snakegourd Peel |
| CN109632994A (en) * | 2018-12-21 | 2019-04-16 | 广东方制药有限公司 | The method for building up of the UPLC map of the seed of cowherb and Semen Vaccariae (parched) and application |
| CN109632994B (en) * | 2018-12-21 | 2022-05-03 | 广东一方制药有限公司 | Method for establishing UPLC (ultra Performance liquid chromatography) spectrum of cowherb seed and fried cowherb seed and application of UPLC spectrum |
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Application publication date: 20120404 |