CN103012326B - Separation and purification method of rhodojaponin-III monomer - Google Patents
Separation and purification method of rhodojaponin-III monomer Download PDFInfo
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Abstract
The invention provides a separation and purification method of a rhodojaponin-III monomer, and belongs to the technical field of separation and purification of active ingredients of traditional Chinese medicines. The separation and purification method comprises the following steps in sequence: based on ericaceous plant rhododendron molle as a raw material, carrying out alcohol extraction, ethyl acetate extraction and preparative high performance liquid chromatography separation; and concentrating and drying to obtain the rhodojaponin-III monomer. According to the preparation method, the optimal technology and parameter conditions are utilized, thus the content of the rhodojaponin-III in the product is up to more than 98%; and the method is simple and convenient for operation in the whole technological process, stable in technology, low in cost, suitable for mass production, high in separation efficiency and high in purity of product, and can realize high-purity separation and preparation of the rhodojaponin-III monomers as mass.
Description
Technical field
The present invention relates to a kind of preparation method of plant compound monomer, be specifically related to the method for extraction and isolation rhodojaponinⅢ monomer from Chinese azalea, belong to the separating and purifying technology field of active ingredient of Chinese herbs.
Background technology
RhodojaponinⅢ is Chinese azalea extract III again, Rhodojaponin 1, and molecular formula is C
20h
32o
6, molecular weight is 368, and structural formula is as follows:
RhodojaponinⅢ derives from ericad Chinese azalea Rhododendron molle G. Don, the main active ingredient in Chinese azalea medicinal material and characteristic component, Chinese azalea extract III is plant insecticide, its Action mechanism mainly contains two aspects, one is act on neural system, affect the nerves cell Triphosaden (ATP) enzymic activity, and block nerves is conducted, and affects ion channel opens; Be intestines biofilm system in destroying in addition, affect digestive enzyme system and removing toxic substances plum system activity.The mode of action is mainly food refusal and stomach poison function, repellent rate effect, has action of contace poison concurrently.
Learn according to coordinate indexing, at present for the separation of rhodojaponinⅢ monomer, mainly adopt the method for periodic crystallisation again after silica gel column chromatography, its production cycle is long, and yield is low.
Summary of the invention
A kind of easy sharp separation is the object of the present invention is to provide to prepare the method for high-content rhodojaponinⅢ, for new drug development and evaluation of medical materials' quality provide support.The method is easy and simple to handle, and separation efficiency is high, and process stabilizing is with low cost, and can realize the high purity separation preparation of a large amount of rhodojaponinⅢ monomer, the rhodojaponinⅢ monomer purity obtained is high, can reach more than 98%.
In order to realize foregoing invention object, the technical solution used in the present invention is as follows:
A separation purification method for rhodojaponinⅢ monomer, is characterized in that: with ericad Chinese azalea medicinal material for raw material, and by extracting, extraction, preparation liquid phase systems be separated and dry rhodojaponinⅢ monomer, specifically comprises following processing step:
A extracts
The Chinese azalea pulverizing medicinal materials of drying is become the meal of 1 ~ 4mm, add alcoholic solution, extract 3 ~ 5 times, each 1 ~ 3 hour, extracting liquid filtering in 60 ~ 100 DEG C, merge filtered liquid, 60 ~ 90 DEG C of concentration and recovery ethanol, obtain the concentrated extract of relative density 1.0 ~ 1.1.
Described alcoholic solution is methyl alcohol or ethanolic soln, and their concentration is G/G=70 ~ 90%.
The add-on of described alcoholic solution is medicinal material weight: alcoholic solution volume=1Kg:(6 ~ 10) L.
By pulverizing, heating extraction, concentrating under reduced pressure, target compound is transferred in medicinal extract and is more conducive to subsequent disposal.
B extracts total toxin
When the concentrated extract of steps A gained being diluted with water to 60 DEG C, relative density is 0.7 ~ 0.9g/mL, then isopyknic extraction into ethyl acetate is added 3 ~ 5 times, divide and get upper solution, 45 ~ 60 DEG C are evaporated to dry, the methyl alcohol ultrasonic dissolution of gained solids mass/volume=10 ~ 15, and with 0.45 μm of organic membrane filter, obtain settled solution.
By extraction into ethyl acetate, dissolve with methanol, organic membrane filtration, can effectively remove most of impurity further, purifying rhodojaponinⅢ.
C is separated rhodojaponinⅢ monomer by preparative high performance liquid chromatography
Get the filtrate sample introduction of step B gained, carry out the preparative separation of rhodojaponinⅢ monomer, UV-detector on-line monitoring specific aim collect rhodojaponinⅢ prepare cut solution, obtain rhodojaponinⅢ monomer solution.
Described preparative high performance liquid chromatography adopts filler to be C
18chromatographic column, moving phase consist of: the methanol aqueous solution of volume fraction 65 ~ 85%.
Described UV-detector determined wavelength is 210nm.
The present invention is before carrying out high performance preparative liquid chromatography separation, and the method commonly used by liquid-mass chromatography or other the art, as carbon-13 nmr spectra, hydrogen spectrum etc. determine the peak shape of rhodojaponinⅢ monomer in high performance liquid chromatography.
For liquid-mass chromatography (HPLC-MS) method, filler can be adopted to be C
18chromatographic column, moving phase consists of: the methanol aqueous solution of volume fraction 65 ~ 85%, column temperature is room temperature, determined wavelength is 210nm, get the appropriate sample introduction of clear filtrate of step B gained, the HPLC-MS carrying out rhodojaponinⅢ monomer detects, UV-detector on-line monitoring, and according to mass spectrum positive ion detected result, determine the peak shape that rhodojaponinⅢ monomer is corresponding in liquid chromatography and ownership.Also C is adopted because preparative high performance liquid chromatography is separated rhodojaponinⅢ monomer
18chromatographic column, and moving phase composition identical, thus can be used for infer in preparative high performance liquid chromatography rhodojaponinⅢ monomer go out peak position and peak shape etc.
RhodojaponinⅢ monomer product is prepared in D drying
Get step D gained rhodojaponinⅢ monomer solution, be evaporated to dry, then coexisted in the Vanadium Pentoxide in FLAKES that 45 ~ 85 DEG C hold with another device by solids in 45 DEG C ~ 75 DEG C, vacuum-drying, to constant weight, is collected dry product, is obtained rhodojaponinⅢ monomer product.
The invention has the advantages that:
1, the present invention is by extraction into ethyl acetate, dissolve with methanol, organic membrane filtration of step B, effectively removes most of impurity further, purifying rhodojaponinⅢ.
2, the present invention adopts preparative high performance liquid chromatography system to be separated rhodojaponinⅢ monomer, by optimum pre-treating process and chromatographic condition etc., reach good separating effect, and UV-detector on-line monitoring, specific aim collects rhodojaponinⅢ monomer, with clearly defined objective, avoid conventional column chromatography and be first separated the wasting of resources detecting afterwards and cause.
3, the present invention adopts preparative high performance liquid chromatography sepn process directly perceived, and targeted is strong, and be easy to control to the quality of product, product purity can reach more than 98%.
4, the present invention is easy and simple to handle, with short production cycle, and separation efficiency is high, and yield is high, and output is large, and process stabilizing is reliable, and favorable reproducibility is with low cost, is applicable to suitability for industrialized production.
5, because high performance liquid chromatography requires all higher to the purity, color and luster etc. of sample solution, the extracting solution obtained by simple process such as extractions directly can not enter highly effective liquid phase chromatographic system as sample solution, if therefore before carrying out high performance liquid chromatography separation, carry out extracting not in accordance with the inventive method step, be hydrolyzed, macroporous adsorbing resin for purification, then likely do not reach good separating effect, also may produce on accessories such as the chromatographic columns of highly effective liquid phase chromatographic system the impact being difficult to reverse, shorten its life cycle; And the related accessory cost of the liquid chromatographies such as chromatographic column is usually higher, the shortening of its life cycle obviously will cause the production cost of the finished product greatly to improve; Thus, require higher to the sample solution entering high performance liquid chromatography, its pretreatment process is extremely important.
6, for the physico-chemical property of the various compositions existed in Chinese azalea medicinal material, the inventive method is by the order collocation of abovementioned steps A, B, and suitable parameters combination, the compositions such as rhodojaponinⅢ are effectively extracted, and eliminate a large amount of impurity, obtain the sample solution (i.e. step B obtain clear filtrate) that can enter preparative high performance liquid chromatography system thus, unlikely very large impact is caused on highly effective liquid phase chromatographic system, extend its life cycle as far as possible, save production cost.
7, in high performance liquid chromatography sepn process, the selection of chromatographic condition is extremely important, and it plays conclusive effect to the peak sequence, peak shape, separating effect etc. of material each in sample solution; Chromatographic condition mainly comprises chromatographic column (comprising filler, column length and internal diameter etc.), moving phase (comprise composition and flow velocity etc.), column temperature, determined wavelength, detector etc., the selection of each chromatographic condition and combine most important.The present invention, by a large amount of experimental studies and comparative analysis, determines each chromatographic condition as above, makes the optimizings such as the appearance time of each material in sample solution, peak shape, separating effect, is conducive to rhodojaponinⅢ monomer and obtains fully effective separation.
Accompanying drawing explanation
Fig. 1 is the high performance liquid preparative chromatography figure of the embodiment of the present invention 1 rhodojaponinⅢ, and be recorded as 3 sample needle continuous sample introduction color atlass in figure, in figure, peak 1,2,3 is rhodojaponinⅢ;
Fig. 2 is the high-efficient liquid phase analysis color atlas that the embodiment of the present invention 2 rhodojaponinⅢ monomer product is rechecked
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, but this should be interpreted as the present invention is only limitted to following embodiment.
In following each embodiment, the purity of finished product rhodojaponinⅢ monomer is rechecked and is all adopted inverse analysis type liquid chromatography (RP-HPLC) method, and chromatographic condition is as follows:
Moving phase consists of: methanol-water, and the two volume ratio is 80:20; Flow velocity 1.0mL/min;
Chromatographic column filler is C
18, granularity is 5 μm, and chromatographic column internal diameter is 4.6mm, and length is 150mm;
Determined wavelength is 210nm.
embodiment 1
A separation purification method for rhodojaponinⅢ monomer, comprises following processing step:
A extracts
The Chinese azalea medicinal material 100Kg of drying is ground into the meal of 1 ~ 4mm, loads volume 2x10
33in the extractor of L, add the methanol solution 600L that mass percent concentration is 90%, 60 DEG C are extracted 3 times, each 3 hours, and extracting liquid filtering merges filtered liquid, 60 DEG C of concentration and recovery methyl alcohol, and the concentrated extract obtaining relative density 1.1 is about 80L next step process pending;
B extracts total toxin
The concentrated extract of steps A gained being diluted with water to relative density is 0.85g/mL(about 60 DEG C mensuration), be total to obtain solution 100L, add isopyknic extraction into ethyl acetate 4 times, make rhodojaponinⅢ be transferred in ethyl acetate solution, divide and get upper solution, 45 DEG C are evaporated to dry, the methyl alcohol ultrasonic dissolution of gained solids 250g 2500ml, and with 0.45 μm of organic membrane filter, obtain settled solution, be for further processing;
C is separated rhodojaponinⅢ monomer by preparative high performance liquid chromatography
A () determines peak shape and the ownership of rhodojaponinⅢ monomer in high performance liquid chromatography:
By liquid-mass chromatography (HPLC-MS), employing filler is C
18chromatographic column (C
18granularity is 5 μm, column length is 250mm, internal diameter 4.6mm), moving phase consists of the methanol aqueous solution of volume fraction 65%, flow velocity 1mL/min, column temperature is room temperature, determined wavelength is 210nm, get step C gained filtrate 10 μ l sample introduction, the HPLC-MS carrying out rhodojaponinⅢ monomer detects, UV-detector on-line monitoring, and according to mass spectrum positive ion detected result, determine the peak shape that rhodojaponinⅢ monomer is corresponding in liquid chromatography, the material corresponding to the peak of appearance time t=17.88-19.39min is rhodojaponinⅢ monomer.
B () prepares rhodojaponinⅢ monomer
Employing filler is C
18chromatographic column (internal diameter 80mm, C
18granularity is 10 μm), moving phase consists of the methanol aqueous solution of volume fraction 65%, flow velocity is 140mL/min, determined wavelength is 210nm, get the clear filtrate sample introduction of step B gained, carry out the preparative separation of rhodojaponinⅢ monomer, UV-detector on-line monitoring, according to situations such as the peak shapes of rhodojaponinⅢ monomer in the high performance liquid chromatography that step (a) is determined, what specific aim collected rhodojaponinⅢ monomer prepares cut solution (appearance time is 48 ~ 51min), obtains rhodojaponinⅢ monomer solution;
RhodojaponinⅢ monomer product is prepared in D drying
Get step D gained rhodojaponinⅢ monomer solution, be evaporated to dry, then coexisted in the Vanadium Pentoxide in FLAKES that 45 DEG C hold with another device by solids in 75 DEG C, vacuum-drying, to constant weight, is collected dry product, is obtained rhodojaponinⅢ monomer product 15.32g.
By changing mobile phase composition, utilize inverse analysis type liquid chromatography (RP-HPLC) to recheck product purity, recording result is 98.82%.
embodiment 2
A separation purification method for rhodojaponinⅢ monomer, comprises following processing step:
A extracts
The Chinese azalea medicinal material 300Kg of drying is ground into 1 ~ 4mm meal, loads volume 4x10
33in the extractor of L, add the methanol solution 2.4x10 that mass percent concentration is 85%
3l, 80 DEG C are extracted 4 times, each 1.5 hours, and extracting liquid filtering merges filtered liquid, 85 DEG C of concentration and recovery methyl alcohol, and the concentrated extract obtaining relative density 1.0 is about 180L next step process pending;
B, extract total toxin
The concentrated extract of steps A gained being diluted with water to relative density is 0.9g/mL(about 60 DEG C mensuration), be total to solution is about 200L, add isopyknic extraction into ethyl acetate 5 times, make rhodojaponinⅢ be transferred in ethyl acetate solution, divide and get upper solution, 50 DEG C are evaporated to dry, the methyl alcohol ultrasonic dissolution of gained solids 762g 9100ml, and with 0.45 μm of organic membrane filter, obtain settled solution, be for further processing;
C, be separated rhodojaponinⅢ monomer by preparative high performance liquid chromatography
A () determines peak shape and the ownership of rhodojaponinⅢ monomer in high performance liquid chromatography
By liquid-mass chromatography (HPLC-MS), employing filler is C
18chromatographic column (C
18granularity is 5 μm, column length is 250mm, internal diameter 4.6mm), moving phase consists of the methanol aqueous solution of volume fraction 85%, flow velocity 1mL/min, column temperature is room temperature, determined wavelength is 210nm, get step C gained filtrate 10 μ l sample introduction, the HPLC-MS carrying out rhodojaponinⅢ monomer detects, UV-detector on-line monitoring, and according to mass spectrum positive ion detected result, determine the peak shape that rhodojaponinⅢ monomer is corresponding in liquid chromatography, the material corresponding to the peak of appearance time t=8.21-8.39min is rhodojaponinⅢ monomer.
(b), prepare rhodojaponinⅢ monomer:
Employing filler is C
18chromatographic column (internal diameter 100mm, C
18granularity is 10 μm), moving phase consists of the methanol aqueous solution of volume fraction 85%, flow velocity is 250mL/min, determined wavelength is 210nm, get the clear filtrate sample introduction of step B gained, carry out the preparative separation of rhodojaponinⅢ monomer, UV-detector on-line monitoring, according to situations such as the peak shapes of rhodojaponinⅢ monomer in the high performance liquid chromatography that step (a) is determined, what specific aim collected rhodojaponinⅢ monomer prepares cut solution (appearance time is 13 ~ 17min), obtains rhodojaponinⅢ monomer solution;
RhodojaponinⅢ monomer product is prepared in D, drying:
Get step D gained rhodojaponinⅢ monomer solution, be evaporated to dry, then coexisted in the Vanadium Pentoxide in FLAKES that 85 DEG C hold with another device by solids in 60 DEG C, vacuum-drying, to constant weight, is collected dry product, is obtained rhodojaponinⅢ monomer product 45.9g.
By changing mobile phase composition, utilize inverse analysis type liquid chromatography (RP-HPLC) to recheck product purity, recording result is 99.12%.
embodiment 3
A separation purification method for rhodojaponinⅢ monomer, comprises following processing step:
A extracts
The Chinese azalea medicinal material 50Kg of drying is ground into 1 ~ 4mm meal, loads volume 1x10
33in the extractor of L, add the ethanolic soln 500L that mass percent concentration is 70%, 100 DEG C are extracted 3 times, each 1 hour, and extracting liquid filtering merges filtered liquid, 90 DEG C of concentration and recovery ethanol, and the concentrated extract obtaining relative density 1.1 is about 20L next step process pending;
B extracts total toxin
The concentrated extract of steps A gained being diluted with water to relative density is 0.7g/mL(about 60 DEG C mensuration), be total to obtain solution 28L, add isopyknic extraction into ethyl acetate 3 times, make rhodojaponinⅢ be transferred in ethyl acetate solution, divide and get upper solution, 60 DEG C are evaporated to dry, the methyl alcohol ultrasonic dissolution of gained solids 123g 1800ml, and with 0.45 μm of organic membrane filter, obtain settled solution, be for further processing;
C is separated rhodojaponinⅢ monomer by preparative high performance liquid chromatography
A () determines peak shape and the ownership of rhodojaponinⅢ monomer in high performance liquid chromatography
By liquid-mass chromatography (HPLC-MS), employing filler is C
18chromatographic column (C
18granularity is 5 μm, column length is 250mm, internal diameter 4.6mm), moving phase consists of the methanol aqueous solution of volume fraction 75%, flow velocity 1mL/min, column temperature is room temperature, determined wavelength is 210nm, get step C gained filtrate 10 μ l sample introduction, the HPLC-MS carrying out rhodojaponinⅢ monomer detects, UV-detector on-line monitoring, and according to mass spectrum positive ion detected result, determine the peak shape that rhodojaponinⅢ monomer is corresponding in liquid chromatography, the material corresponding to the peak of appearance time t=20.88-21.65min is rhodojaponinⅢ monomer.
B () prepares rhodojaponinⅢ monomer
Employing filler is C
18chromatographic column (internal diameter 50mm, C
18granularity is 10 μm), moving phase consists of the methanol aqueous solution of volume fraction 75%, flow velocity is 60mL/min, determined wavelength is 210nm, get the clear filtrate sample introduction of step B gained, carry out the preparative separation of rhodojaponinⅢ monomer, UV-detector on-line monitoring, according to situations such as the peak shapes of rhodojaponinⅢ monomer in the high performance liquid chromatography that step (a) is determined, what specific aim collected rhodojaponinⅢ monomer prepares cut solution (appearance time is 45 ~ 47min), obtains rhodojaponinⅢ monomer solution;
RhodojaponinⅢ monomer product is prepared in D drying
Get step D gained rhodojaponinⅢ monomer solution, be evaporated to dry, then coexisted in the Vanadium Pentoxide in FLAKES that 60 DEG C hold with another device by solids in 45 DEG C, vacuum-drying, to constant weight, is collected dry product, is obtained rhodojaponinⅢ monomer product 8.15g.
By changing mobile phase composition, utilize inverse analysis type liquid chromatography (RP-HPLC) to recheck product purity, recording result is 98.61%.
Claims (3)
1. a separation purification method for rhodojaponinⅢ monomer, is characterized in that: with ericad Chinese azalea medicinal material for raw material, and by extracting, extraction, preparation liquid phase systems be separated and dry rhodojaponinⅢ monomer, specifically comprises following processing step:
A extracts
The Chinese azalea pulverizing medicinal materials of drying is become the meal of 1 ~ 4mm, add alcoholic solution, extract 3 ~ 5 times, each 1 ~ 3 hour, extracting liquid filtering in 60 ~ 100 DEG C, merge filtered liquid, 60 ~ 90 DEG C of concentration and recovery ethanol, obtain the concentrated extract of relative density 1.0 ~ 1.1;
B extracts total toxin
When the concentrated extract of steps A gained being diluted with water to 60 DEG C, relative density is 0.7 ~ 0.9g/mL, then isopyknic extraction into ethyl acetate is added 3 ~ 5 times, divide and get upper solution, 45 ~ 60 DEG C are evaporated to dry, the methyl alcohol ultrasonic dissolution of gained solids mass/volume=10 ~ 15, and with 0.45 μm of organic membrane filter, obtain settled solution;
C is separated rhodojaponinⅢ monomer by preparative high performance liquid chromatography
Get the filtrate sample introduction of step B gained, carry out the preparative separation of rhodojaponinⅢ monomer, UV-detector on-line monitoring specific aim collect rhodojaponinⅢ prepare cut solution, obtain rhodojaponinⅢ monomer solution;
RhodojaponinⅢ monomer product is prepared in D drying
Get step D gained rhodojaponinⅢ monomer solution, be evaporated to dry, then coexisted in the Vanadium Pentoxide in FLAKES that 45 ~ 85 DEG C hold with another device by solids in 45 DEG C ~ 75 DEG C, vacuum-drying, to constant weight, is collected dry product, is obtained rhodojaponinⅢ monomer product;
Alcoholic solution described in steps A is ethanolic soln, and its mass percent concentration is 70 ~ 90%;
The add-on of alcoholic solution described in steps A is medicinal material weight: alcoholic solution volume=1Kg:(6 ~ 10) L;
Preparative high performance liquid chromatography described in step C adopts filler to be C
18chromatographic column, moving phase consist of: the methanol aqueous solution of volume fraction 65 ~ 85%;
UV-detector determined wavelength described in step C is 210nm.
2. the separation purification method of rhodojaponinⅢ monomer as claimed in claim 1, it is characterized in that: before preparative high performance liquid chromatography described in step C is separated, by the peak shape of rhodojaponinⅢ monomer in liquid-mass chromatography method or compounds GC-MS, carbon-13 nmr spectra, hydrogen spectral method determination high performance liquid chromatography.
3. the separation purification method of rhodojaponinⅢ monomer as claimed in claim 2, it is characterized in that described liquid-mass chromatography method, employing filler is C
18chromatographic column, moving phase consists of: the methanol aqueous solution of volume fraction 65 ~ 85%, and column temperature is room temperature, and determined wavelength is 210nm, according to mass spectrum positive ion detected result, determines the peak shape that rhodojaponinⅢ monomer is corresponding in liquid chromatography and ownership.
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| CN111377888B (en) * | 2020-06-01 | 2020-10-16 | 中国农业科学院蜜蜂研究所 | Rhododendrin mollis toxin III hapten as well as preparation method and application thereof |
| CN111646898B (en) * | 2020-08-06 | 2020-12-25 | 中国农业科学院蜜蜂研究所 | Chenopodium quinotoxin III hapten, artificial antigen, preparation method and application thereof |
| CN112089745B (en) * | 2020-09-22 | 2022-03-15 | 重庆市中医院 | Processing method of rhododendron molle and rhododendron molle decoction pieces |
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| CN101648932A (en) * | 2009-09-04 | 2010-02-17 | 昆明理工大学 | 3,4-ring-opening polyacylation grayananes diterpene compound and preparation method thereof |
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| CN101648932A (en) * | 2009-09-04 | 2010-02-17 | 昆明理工大学 | 3,4-ring-opening polyacylation grayananes diterpene compound and preparation method thereof |
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