CN102311466A - Method for extracting phenylethanoid glycoside active components from semenplantaginis - Google Patents
Method for extracting phenylethanoid glycoside active components from semenplantaginis Download PDFInfo
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- 150000002338 glycosides Chemical class 0.000 title abstract description 4
- 239000000284 extract Substances 0.000 claims abstract description 85
- 239000002904 solvent Substances 0.000 claims abstract description 36
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 141
- -1 benzyl carbinol glycosides Chemical class 0.000 claims description 95
- 210000000582 Semen Anatomy 0.000 claims description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 62
- 238000000605 extraction Methods 0.000 claims description 44
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- 239000000243 solution Substances 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 28
- 239000000741 silica gel Substances 0.000 claims description 26
- 229910002027 silica gel Inorganic materials 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 26
- 238000000967 suction filtration Methods 0.000 claims description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
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- IQPNAANSBPBGFQ-UHFFFAOYSA-N Luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 description 2
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- 238000004809 thin layer chromatography Methods 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-N (2E)-3-phenylprop-2-enoic acid Chemical group OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical group CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a method for extracting phenylethanoid glycoside active components from semenplantaginis. The method comprises extracting by solvents and refining by a chromatography to obtain extract. The obtained extract contains phenylethanoid glycoside active components with a total content above 50%. The method is simple, is suitable for industrialized production, and has a prospect of industrial application.
Description
Technical field
The invention belongs to natural medicine technical field, be specifically related to a kind of method of from Semen Plantaginis, extracting the benzyl carbinol glycosides active component.
Background technology
Semen Plantaginis (Semenplantaginis) is one of China's tradition medicinal material, has another name called blocking the way, ox something lost, frog clothing, in addition; Claim the preceding dish of car, Leaf of Toothedfruit Dock, wheel dish, pig Auricled Hedyotis Herb etc. in addition; Beginning is shown in " Book of Songs ", and the medicinal beginning is stated from Shennong's Herbal, and is classified as in the medicine top grade.
Semen Plantaginis is Plantaginaceae plant Plantago depressa Willd (Plantago depressa Willd.), claim before the granule car again or car before (Plantago asiatica Linn.), claim the dry seed before the big grain car again, distribution is all arranged throughout the country, resource is extensive.Have relieving stranguria by diuresis, excreting dampness antidiarrheal, clear liver and improve vision, the effect of removing heat-phlegm.Contain a large amount of phlegmatic temperaments (polysaccharide compound) in the Semen Plantaginis (referring to Tomoda Masashi; Yokoi Maemi; Ishikawa Kazuyo.Plant Mucilages.XXIX. [J] .asiatica.J.Chen Pharm Bull, 1981,29 (10): 2884-2887. and ohn F Kennedy; Jasbir S Sandhu; David A T.Southgate. [J] .Carbohydrate Research, 1979,75:265-274.) and plantenolic acid, choline, VITAMIN B4, succsinic acid, protein, trace element etc.Contain flavonoid compound: mainly contain luteolin, Homoplantaginin, plantagin etc.Triterpene compound: mainly contain ursolic acid, Oleanolic Acid etc.Volatile oil: mainly contain DBPC 2,6 ditertiary butyl p cresol and 3-tertiary butyl-4-hydroxy phenylmethylether etc.; Cyclenes ether glycosides compound is like aucubin, Geniposidic acid; The benzyl carbinol glycosides compounds: verbascoside etc. (referring to Wang Shaohua, Luo Guangming etc. chemical ingredients of Chinese medicine Semen Plantaginis and pharmaceutical research progress. the Asia-Pacific traditional medicine, 2008,9 (9), 133-135.).Wherein have most DEVELOPMENT PROSPECT one of reactive site be exactly the benzyl carbinol glycosides compounds, comprise verbascoside etc.
Modern study shows; Benzyl carbinol glycosides compounds (phenylethanoid glycosides) is one type and contains (hydroxyl, methoxyl group) substituted benzene ethyl and (hydroxyl, methoxyl group) replacement cinnamoyl; Usually be the natural glucosides that contains ester bond and oxygen glycosidic bond of parent nucleus with B one glucose; Extensively be present in the dicotyledons, biological activity is very strong, receives vegetable chemistry and pharmacy worker's great attention.Many in recent years researchs show, that this compounds has is antibiotic, anti-inflammatory, antiviral, antitumor, anti-oxidant, immunomodulatory, hypermnesis, protect the liver, effect such as cardiac stimulant (referring to quiet meeting, help and build cutting edge of a knife or a sword etc. the time treasure traditional Chinese medical science traditional Chinese medicines .2006,17 (3): 440-441).
Semen Plantaginis all has distribution throughout the country, wide material sources, and cheap, content is higher in the medicinal material, extracts phenylethyl alcohol glycoside activity from Semen Plantaginis and has vast market prospect.The Semen Plantaginis complicated component, a lot of compound structures are close with character, and therefore, the extraction separation that from Semen Plantaginis, extracts the benzyl carbinol glycosides active component is comparatively difficult, and yield is very low.
Summary of the invention
Goal of the invention of the present invention provides a kind of method of from Semen Plantaginis, extracting the benzyl carbinol glycosides active component, and extract obtained middle benzyl carbinol glycosides constituents quality percentage composition is more than 50%.
The method of from Semen Plantaginis, extracting the benzyl carbinol glycosides active component provided by the invention may further comprise the steps:
Step 1: Semen Plantaginis is pulverized, extract 1-4 time or refluxing extraction or supersound extraction or cold soaking or diacolation extraction with first polar solvent, suction filtration goes out extracting solution; Centrifugal or the suction filtration of extracting solution is isolated supernatant; The mixing solutions of the aqueous solution, acetone, acetone and water that said first polar solvent is the 0-100%C1-C6 alkyl alcohol or contain acid or the above-mentioned solvent of alkali;
Step 2: supernatant is mixed in behind silica gel or the zeyssatite or directly supernatant is made with extra care with chromatogram; The eluting solvent wash-out; Stream part of benzyl carbinol glycosides compounds is rich in collection, and concentrate drying gets said Semen Plantaginis extract; The quality percentage composition of benzyl carbinol glycosides active component is preferably 50%-95% more than 50% in the said Semen Plantaginis extract; Wherein said chromatogram is macroporous adsorbent resin chromatography, polymeric amide chromatogram, purification on normal-phase silica gel or reverse phase silica gel chromatogram or its combination.
As preferably; The mixing solutions of the aqueous solution, acetone, acetone and water that said first polar solvent of step 1 is the 50-95%C1-C6 alkyl alcohol or contain acid or the above-mentioned solvent of alkali; Said acid or alkali are strong acid, highly basic or weak acid, weak base, are preferably the Na of 0.5%HCL, 1% acetic acid, 0.5%NaOH or 1%
2CO
3, the said above-mentioned solvent that contains acid or alkali is preferably the Na that contains 0.5%HCL, 1% acetic acid, 0.5%NaOH or 1%
2CO
3The aqueous solution, acetone or acetone and the mixing solutions of water of 50-95%C1-C6 alkyl alcohol.
As preferably, said C1-C6 alkyl alcohol is the mixed solvent that methyl alcohol, ethanol, Virahol or propyl carbinol or their are formed.
As preferably, the said eluting solvent of step 2 is a water, the C1-C6 alkyl alcohol, halohydrocarbon, ether solvent, ketones solvent, esters solvent, with and the mixed solvent of two or more compositions.
As preferably, the said eluting solvent of step 2 is for being selected from methyl alcohol, ethanol, Virahol, propyl carbinol, methylene dichloride, trichloromethane, ether, methyl tert-butyl ether, acetone, 2-butanone, ETHYLE ACETATE, ethyl formate.More preferably said eluting solvent is the mixed solvent of trichloromethane, ETHYLE ACETATE, ethanol, first alcohol and water composition.
Make with extra care with chromatogram, when said chromatogram is a macroporous adsorbent resin chromatography, preferred eluting solvent is ethanol or the methanol aqueous solution of water and 10-75%, and benzyl carbinol glycosides constituents total content is at 50%-60% in the extract; Said chromatogram is the polymeric amide chromatogram, and preferred eluting solvent is ethanol or the methanol aqueous solution of water and 10-75%, and benzyl carbinol glycosides constituents total content is at 50%-60% in the extract; Said chromatogram is the reverse phase silica gel chromatogram, and preferred eluting solvent is aqueous ethanolic solution or the methanol aqueous solution of water and 10-50%, and benzyl carbinol glycosides constituents total content is at 70%-95% in the extract; Said chromatogram is a purification on normal-phase silica gel, and preferred eluting solvent is the mixed solvent of trichloromethane, ETHYLE ACETATE, 90-100% aqueous ethanolic solution, methyl alcohol or its composition, and benzyl carbinol glycosides constituents total content is at 60%-80% in the extract.
In embodiment of the present invention, macroporous resin is selected from HP-20 type macroporous resin or AB-8 type macroporous resin, uses the aqueous ethanolic solution gradient elution, is rich in the benzyl carbinol glycosides composition and is present in the 30% alcoholic acid elutriant; When making with extra care with polyamide column, be rich in the benzyl carbinol glycosides composition and be present in the 50% alcoholic acid elutriant, this physicochemical property with the weighting material of different chromatography columns is relevant.
As preferably, said usefulness first polar solvent of step 1 is extracted as first polar solvent that at every turn adds 4-20BV and extracts to the temperature of solvent refluxing at 0 ℃.
As preferably, step 1 extracting solution carries out concentration before separating supernatant, and the volume mass of preferred simmer down to extracting solution and Semen Plantaginis raw material is than counting 0.1-1 with ml/g: 10-1.
As preferably, the temperature that the said extraction TR of step 1 is room temperature a to solvent refluxing.
The method of from Semen Plantaginis, extracting the benzyl carbinol glycosides active component provided by the invention, extract obtained in benzyl carbinol glycosides constituents total content more than 50%, and detect and contain verbascoside and verivate composition thereof, the verbascoside structure is as follows:
Among the said preparation method, the benzyl carbinol glycosides total content is surveyed through the inspection of ultraviolet (UV) method, and the stream part of being rich in verbascoside is detected through thin-layer chromatography (TLC), ultraviolet (UV), HPLC methods such as (HPLC), wherein preferred HPLC detection method.
The invention discloses a kind of method of from Semen Plantaginis, extracting the benzyl carbinol glycosides active component, the method for the invention adopts solvent extraction, and is refining through chromatographic process, obtains extract; Effective constituent phenylethyl alcohol glycoside total content is more than 50% in the prepared extract, and macroporous adsorbent resin method for refining technology is simple, is suitable for suitability for industrialized production, has prospects for commercial application.
Embodiment
The invention discloses a kind of method of from Semen Plantaginis, extracting the benzyl carbinol glycosides active component, those skilled in the art can use for reference this paper content, suitably improve processing parameter and realize.Special needs to be pointed out is that all similarly replace and change apparent to those skilled in the art, they all are regarded as and are included in the present invention.Method of the present invention and application are described through preferred embodiment; The related personnel obviously can change or suitably change and combination methods and applications as herein described in not breaking away from content of the present invention, spirit and scope, realizes and use technology of the present invention.
In order to make those skilled in the art understand technical scheme of the present invention better, the present invention is done further detailed description below in conjunction with specific embodiment.
Embodiment 1:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds 70% ethanol with 10 times liquid-solid ratioes; Ultrasonic (frequency 80KHz) extracts 30min, repeats to extract suction filtration 3 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: that the flow velocity of above-mentioned filtrating with 0.5BV/h joined in pretreated HP-20 type macroporous resin column; The ethanol of water, 5%, 30% and 75% concentration gradient is successively washed; HPLC detects, and collects the elutriant (30% ethanol elution part) that is rich in the benzyl carbinol glycosides compounds, is concentrated into thick paste; Vacuum-drying obtains the total phenylethyl alcohol glycoside of Semen Plantaginis extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 54%.
Embodiment 2:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and extracts with 70% alcohol heating reflux, and each liquid-solid ratio with 4 times adds 70% ethanol, and the 2h that refluxes for the first time is for the second time with the 1h that refluxes for the third time.Suction filtration, united extraction liquid reclaims ethanol and also is concentrated into 1000ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: that the flow velocity of above-mentioned filtrating with 1BV/h joined in pretreated AB-8 type macroporous resin column; The ethanol of water, 5%, 30% and 75% concentration gradient is successively washed; HPLC detects, and collects the 30% ethanol part that is rich in the phenylethyl alcohol glycoside, is concentrated into medicinal extract; Vacuum-drying obtains the total phenylethyl alcohol glycoside of Semen Plantaginis extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 51%.
Embodiment 3:
(1) extract: Semen Plantaginis is softening with water vapour, and oven dry is pulverized, and sieves; Take by weighing the Plantago Seed 1000g after the processing, adopt decocting to extract, add deionized water, extract 2h at every turn with 40 times liquid-solid ratioes; Re-treatment 3 times with extracting liquid filtering, merges, and reclaims ethanol and is concentrated into 1000ml; Be cooled to room temperature, leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: the flow velocity with 1BV/h joins above-mentioned filtrating in the post of pretreated polymeric amide; The ethanol of water, 10%, 50% and 75% concentration gradient is successively washed; HPLC detects; 50% ethanol elution part of phenylethyl alcohol glycoside is rich in collection, and concentrating under reduced pressure, vacuum-drying obtain the total phenylethyl alcohol glycoside of Semen Plantaginis extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 52%.
Embodiment 4:
(1) extracts: Semen Plantaginis is pulverized, cross 20 mesh sieves, take by weighing 1000g and add 60% ethanol room temperature lixiviate 4 times, each 24.0h.United extraction liquid reclaims ethanol and also is concentrated into 1000ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: as to treat that with above-mentioned upper prop filtrating joins on the pretreated ADS-8 post with the flow velocity of 2BV/h; Use water elution in order to the 1BV/h flow velocity; Use the alcoholic solution wash-out of 10%, 30% and 70% concentration again, HPLC detects, and collects the 30% wash-out part that is rich in the phenylethyl alcohol glycoside; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 51%.
Embodiment 5:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts 60% ethanol (containing 0.5%NaOH) heating and refluxing extraction 4 times, and each liquid-solid ratio with 10 times adds 60% ethanol (containing 0.5%NaOH), the 2h that refluxes for the first time, back three backflow 1h.Suction filtration, united extraction liquid reclaims ethanol and is concentrated into medicinal extract.
(2) refining: with condensed cream and silica gel mixed sample; Through purification on normal-phase silica gel (100-200 order) post; With ETHYLE ACETATE-methyl alcohol (10: 1) wash-out, use ETHYLE ACETATE-methyl alcohol (5: 1) and ETHYLE ACETATE-methyl alcohol (1: 1) wash-out more earlier, collect (ETHYLE ACETATE: methyl alcohol is 10: 1) stream part of being rich in the phenylethyl alcohol glycoside; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 76%.
Embodiment 6:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds 60% methyl alcohol with 10 times liquid-solid ratioes; 60 ℃ of temperature, supersound extraction 30min when frequency is 80KHz repeats to extract suction filtration 4 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: as to treat that with above-mentioned upper prop filtrating joins on the pretreated polyamide column with the flow velocity of 3BV/h; Use water elution in order to the 1BV/h flow velocity; Use the alcoholic solution wash-out of 5%, 30% and 70% concentration again, HPLC detects, and collects the 30% wash-out part that is rich in the phenylethyl alcohol glycoside; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 51%.
Embodiment 7:
(1) extracts: Semen Plantaginis is pulverized, cross 20 mesh sieves, take by weighing 1000g and add 95% ethanol room temperature lixiviate 2 times, each 24.0h.United extraction liquid reclaims ethanol and is concentrated into medicinal extract.
(2) refining: the medicinal extract silica gel mixed sample; Through purification on normal-phase silica gel (100-200 order) chromatographic column, behind chloroform-methanol (9: the 1) wash-out, use chloroform-methanol (3: 1) and chloroform-methanol (1: 1) wash-out again; HPLC detects; Stream part (the chloroform-methanol ratio is 9: 1 parts) of benzyl carbinol glycosides compounds is rich in collection, concentrating under reduced pressure, the dry Semen Plantaginis phenylethyl alcohol glycoside extract that gets.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 76%.
Embodiment 8:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds acetone with 10 times liquid-solid ratioes; 60 ℃ of temperature, supersound extraction 30min when frequency is 80KHz repeats to extract suction filtration 2 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: as will to filtrate and use n-butanol extraction, and reclaim solvent and get n-butyl alcohol extract; Extract is crossed reverse phase silica gel (C-18) post, water and 10% ethanol, and 30 ethanol, 70% ethanolic soln wash-out, HPLC detects, and collects the 30% stream part of being rich in the benzyl carbinol glycosides compounds, concentrating under reduced pressure, the dry Semen Plantaginis phenylethyl alcohol glycoside extract that gets.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 92%.
Embodiment 9:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts 70% Virahol heating and refluxing extraction, adds 70% Virahol with 20 times liquid-solid ratioes, refluxing extraction 1 time.Suction filtration, united extraction liquid reclaims ethanol and also is concentrated into 800ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: that liquid concentrator through reverse phase silica gel (C-18) post, behind water and the 10% methanol solution wash-out, is used the methanol solution wash-out of 50% concentration again; HPLC detects; 50% stream part of benzyl carbinol glycosides compounds, concentrating under reduced pressure, the dry Semen Plantaginis phenylethyl alcohol glycoside extract that gets are rich in collection.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 82%.
Embodiment 10:
(1) extracts: Semen Plantaginis is pulverized, cross 20 mesh sieves, take by weighing 1000g and add 50% acetone room temperature lixiviate 3 times, each 24.0h.United extraction liquid reclaims ethanol and is concentrated into medicinal extract.
(2) refining: the medicinal extract silica gel mixed sample; Through purification on normal-phase silica gel (100-200 order) chromatographic column, behind chloroform-95% ethanol (20: the 1) wash-out, use chloroform-95% ethanol (5: 1) and chloroform-95% ethanol (1: 1) wash-out again; HPLC detects; Stream part (chloroform-95% ethanol ratio is 20: 1 parts) of benzyl carbinol glycosides compounds is rich in collection, concentrating under reduced pressure, the dry Semen Plantaginis phenylethyl alcohol glycoside extract that gets.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 73%.
Embodiment 11:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts 50% alcohol heating reflux to extract, and adds 50% ethanol with 10 times liquid-solid ratioes, refluxing extraction 3 times.Suction filtration, united extraction liquid reclaims ethanol and also is concentrated into 1000ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: as to treat that with above-mentioned upper prop filtrating joins on the pretreated D101 post with the flow velocity of 0.5BV/h; Use water elution in order to the 1BV/h flow velocity; Use the alcoholic solution wash-out of 5%, 30% and 70% concentration again, HPLC detects, and collects the 30% wash-out part that is rich in the benzyl carbinol glycosides compounds; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 51%.
Embodiment 12:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds 50% ethanol (containing 1% acetic acid) with 10 times liquid-solid ratioes; 60 ℃ of temperature, supersound extraction 30min when frequency is 80KHz repeats to extract suction filtration 3 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: the medicinal extract silica gel mixed sample; Through purification on normal-phase silica gel (100-200 order) chromatographic column, behind ETHYLE ACETATE-95% ethanol (15: the 1) wash-out, use ETHYLE ACETATE-95% ethanol (3: 1) and ETHYLE ACETATE-95% ethanol (1: 1) wash-out again; HPLC detects; Stream part (chloroform-95% ethanol ratio is 15: 1 parts) of benzyl carbinol glycosides compounds is rich in collection, concentrating under reduced pressure, the dry Semen Plantaginis phenylethyl alcohol glycoside extract that gets.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 76%.
Embodiment 13:
(1) extracts: Semen Plantaginis is pulverized, cross 20 mesh sieves, take by weighing 1000g and add 20 times of deionized water room temperatures lixiviate 3 times, each 24.0h.United extraction liquid is concentrated into 1000ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: that the flow velocity of above-mentioned filtrating with 0.5BV/h joined on the pretreated HPD-100 post; Use water elution in order to the 1BV/h flow velocity; Use the methanol solution wash-out of 5%, 30% and 75% concentration again, HPLC detects, and collects 30% methanol-eluted fractions part; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 52%.
Embodiment 14:
(1) extracts: Semen Plantaginis is pulverized, cross 20 mesh sieves, take by weighing 1000g and adopt decocting to extract, add deionized water with 40 times liquid-solid ratioes; Each 1h that extracts, re-treatment 3 times is with extracting liquid filtering; Merge, reclaim ethanol and be concentrated into 1000ml, be cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: the flow velocity with 1BV/h joins above-mentioned filtrating through pretreated AB-8 type macroporous adsorbent resin; The methyl alcohol of water, 10%, 30% and 70% concentration gradient is successively washed; HPLC detects; 30% methanol-eluted fractions part of phenylethyl alcohol glycoside is rich in collection, and concentrating under reduced pressure, vacuum-drying obtain the total phenylethyl alcohol glycoside of Semen Plantaginis extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 50%.
Embodiment 15:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts the deionized water ultrasonic extraction, adds deionized water with 20 times liquid-solid ratioes; 30 ℃ of temperature, supersound extraction 30min when frequency is 80KHz repeats to extract suction filtration 3 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: above-mentioned filtrating extracts with ethyl formate, reclaims solvent and gets the ethyl formate extract.The ethyl formate extract is used water dissolution; The flow velocity of filtrating with 0.5BV/h is passed through reverse phase silica gel post (C-18), behind water and the 10% alcoholic solution wash-out, use the alcoholic solution wash-out of 50% concentration again; HPLC detects; 50% stream part of phenylethyl alcohol glycoside is rich in collection, concentrating under reduced pressure, and vacuum-drying promptly gets Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 85%.
Embodiment 16:
(1) extract: Semen Plantaginis is pulverized, cross 20 mesh sieves, 30% ethanol that takes by weighing 20 times of 1000g addings (contains 1%NaCO
3) room temperature lixiviate 2 times, each 24.0h.United extraction liquid reclaims ethanol and also is concentrated into 1000ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: as to treat that with above-mentioned upper prop filtrating joins on the pretreated D101 post with the flow velocity of 0.5BV/h; Use water elution in order to the 1BV/h flow velocity; Use the methanol solution wash-out of 5%, 30% and 70% concentration again, HPLC detects, and collects 30% methanol-eluted fractions part; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 54%.
Embodiment 17:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts 30% alcohol heating reflux to extract, and adds 30% ethanol with 15 times liquid-solid ratioes, refluxing extraction 3 times.Suction filtration, united extraction liquid reclaims ethanol and also is concentrated into 1000ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: as will to filtrate and use n-butanol extraction, and reclaim the solvent propyl carbinol, condensed cream and silica gel mixed sample; Through purification on normal-phase silica gel (100-200 order) post; Behind ethyl formate-95% ethanol (15: the 1) wash-out, use ethyl formate-95% ethanol (4: 1) and ethyl formate-95% ethanol (1: 1) gradient elution again, collect phenylethyl alcohol glycoside (ethyl formate-95% ethanol is 15: 1) the stream part of being rich in; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 78%.
Embodiment 18:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds 30% ethanol with 15 times liquid-solid ratioes; 60 ℃ of temperature, supersound extraction 30min when frequency is 80KHz repeats to extract suction filtration 3 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: that the flow velocity of above-mentioned filtrating with 0.5BV/h joined in pretreated AB-8 type macroporous resin column; The ethanol of water, 10%, 30% and 75% concentration gradient is successively washed; HPLC detects, and collects the elutriant (30% ethanol elution part) that is rich in the phenylethyl alcohol glycoside, is concentrated into thick paste; Vacuum-drying obtains the total phenylethyl alcohol glycoside of Semen Plantaginis extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 51%.
Embodiment 19:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts 45% alcohol heating reflux to extract, and adds 45% ethanol with 15 times liquid-solid ratioes, refluxing extraction 3 times.Suction filtration, united extraction liquid reclaims ethanol and also is concentrated into 1000ml, is cooled to room temperature, leaves standstill 24h, centrifugally gets rid of filter, clear filtrate.
(2) refining: the flow velocity with 1BV/h joins above-mentioned filtrating in the post of pretreated HP-20; The methyl alcohol of water, 10%, 30% and 75% concentration gradient is successively washed; The phenylethyl alcohol glycoside that collection is rich in (30% methyl alcohol) stream part; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 55%.
Embodiment 20:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds 45% ethanol with 15 times liquid-solid ratioes; 30 ℃ of temperature, supersound extraction 30min when frequency is 80KHz repeats to extract suction filtration 3 times; United extraction liquid reclaims ethanol and is concentrated into the medicinal extract shape, adding distil water ultrasonic dissolution, suction filtration; Filtrating is used n-butanol extraction, reclaims the solvent propyl carbinol, gets n-butyl alcohol extract.
(2) refining: n-butyl alcohol extract is used dissolved in distilled water, filters, and filtrating is passed through reverse phase silica gel post (C-18) with the flow velocity of 0.5BV/h; Behind water and the 10% methanol solution wash-out; Use the methanol solution wash-out of 50% concentration again, HPLC detects, and collects the 50% methyl alcohol stream part of being rich in the phenylethyl alcohol glycoside; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 82%.
Embodiment 21:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds 70% ethanol with 10 times liquid-solid ratioes; Ultrasonic (frequency 80KHz) extracts 30min, repeats to extract suction filtration 3 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: the flow velocity of above-mentioned filtrating with 0.5BV/h joined in pretreated HP-20 type macroporous resin column, and the ethanol of water, 5%, 30% and 75% concentration gradient is successively washed, and HPLC detects; The elutriant (30% ethanol elution part) of benzyl carbinol glycosides compounds is rich in collection, concentrates, and liquid concentrator is through reverse phase silica gel (C-18) post; Behind water and the 10% methanol solution wash-out; Use the methanol solution wash-out of 50% concentration again, HPLC detects, and collects the 50% stream part of being rich in the benzyl carbinol glycosides compounds; Concentrating under reduced pressure, the dry Semen Plantaginis phenylethyl alcohol glycoside extract that gets.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 92%.
Embodiment 22:
(1) extract: Semen Plantaginis is pulverized, and crosses 20 mesh sieves, takes by weighing 1000g and adopts ultrasonic extraction, adds 60% methyl alcohol with 10 times liquid-solid ratioes; 60 ℃ of temperature, supersound extraction 30min when frequency is 80KHz repeats to extract suction filtration 4 times; United extraction liquid reclaims ethanol and is concentrated into 1000ml, is cooled to room temperature; Leave standstill 24h, centrifugally get rid of filter, clear filtrate.
(2) refining: as to treat that with above-mentioned upper prop filtrating joins on the pretreated polyamide column with the flow velocity of 3BV/h, use water elution, use the alcoholic solution wash-out of 5%, 30% and 70% concentration again in order to the 1BV/h flow velocity; HPLC detects, and collects the 30% wash-out part that is rich in the phenylethyl alcohol glycoside, concentrating under reduced pressure; Liquid concentrator is through purification on normal-phase silica gel (100-200 order) post; With ETHYLE ACETATE-methyl alcohol (10: 1) wash-out, use ETHYLE ACETATE-methyl alcohol (5: 1) and ETHYLE ACETATE-methyl alcohol (1: 1) wash-out more earlier, collect (ETHYLE ACETATE: methyl alcohol is 10: 1) stream part of being rich in the phenylethyl alcohol glycoside; Concentrating under reduced pressure, vacuum-drying promptly get Semen Plantaginis phenylethyl alcohol glycoside extract.Measure through ultraviolet (UV) method, wherein the benzyl carbinol glycosides kind compound content is 86%.
The above only is a preferred implementation of the present invention; Should be pointed out that for those skilled in the art, under the prerequisite that does not break away from the principle of the invention; Can also make some improvement and retouching, these improvement and retouching also should be regarded as protection scope of the present invention.
Claims (13)
1. method of from Semen Plantaginis, extracting the benzyl carbinol glycosides active component may further comprise the steps:
Step 1: Semen Plantaginis is pulverized, extract 1-4 time or refluxing extraction or supersound extraction or cold soaking or diacolation extraction with first polar solvent, suction filtration goes out extracting solution; Centrifugal or the suction filtration of extracting solution is isolated supernatant; The mixing solutions of the aqueous solution, acetone, acetone and water that said first polar solvent is a 0-100%C 1-C6 alkyl alcohol or contain acid or the above-mentioned solvent of alkali;
Step 2: supernatant is mixed in behind silica gel or the zeyssatite or directly supernatant is made with extra care with chromatogram; The eluting solvent wash-out; Stream part of benzyl carbinol glycosides compounds is rich in collection; Concentrate drying makes Semen Plantaginis extract, and the quality percentage composition of benzyl carbinol glycosides active component is more than 50% in the said Semen Plantaginis extract; Wherein said chromatogram is macroporous adsorbent resin chromatography, polymeric amide chromatogram, purification on normal-phase silica gel or reverse phase silica gel chromatogram or its combination.
2. method according to claim 1 is characterized in that, the mixing solutions of the aqueous solution, acetone, acetone and water that said first polar solvent is a 50-95%C 1-C6 alkyl alcohol or contain acid or the above-mentioned solvent of alkali.
3. method according to claim 2 is characterized in that, said C1-C6 alkyl alcohol is the mixed solvent of methyl alcohol, ethanol, Virahol or propyl carbinol or their compositions.
4. method according to claim 1 is characterized in that, said eluting solvent is a water, the C1-C6 alkyl alcohol, halohydrocarbon, ether solvent, ketones solvent, esters solvent, with and the mixed solvent of two or more compositions.
5. method according to claim 1 is characterized in that, said eluting solvent is for being selected from methyl alcohol, ethanol, Virahol, propyl carbinol, methylene dichloride, trichloromethane, ether, methyl tert-butyl ether, acetone, 2-butanone, ETHYLE ACETATE, ethyl formate.
6. method according to claim 1 is characterized in that, said eluting solvent is the mixed solvent of trichloromethane, ETHYLE ACETATE, ethanol, first alcohol and water composition.
7. method according to claim 1 is characterized in that, said chromatogram is a macroporous adsorbent resin chromatography, and eluting solvent is ethanol or the methanol aqueous solution of water and 10-75%.
8. method according to claim 1 is characterized in that, said chromatogram is the polymeric amide chromatogram, and eluting solvent is aqueous ethanolic solution or the methanol aqueous solution of water and 10-75%.
9. method according to claim 1 is characterized in that, said chromatogram is the reverse phase silica gel chromatogram, and eluting solvent is aqueous ethanolic solution or the methanol aqueous solution of water and 10-50%.
10. method according to claim 1 is characterized in that, said chromatogram is a purification on normal-phase silica gel, and eluting solvent is the mixed solvent of trichloromethane, ETHYLE ACETATE, 90-100% aqueous ethanolic solution, methyl alcohol or its composition.
11. method according to claim 1 is characterized in that, said usefulness first polar solvent of step 1 is extracted as first polar solvent that at every turn adds 4-20BV and extracts to the temperature of solvent refluxing at 0 ℃.
12. method according to claim 1 is characterized in that, step 1 extracting solution carries out concentration before separating supernatant, and the volume mass of preferred simmer down to extracting solution and Semen Plantaginis raw material is than counting 0.1-1 with ml/g: 10-1.
13. method according to claim 11 is characterized in that, said first polar solvent that uses of step 1 extracts the temperature of TR as room temperature to solvent refluxing.
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| CN112586515A (en) * | 2020-12-22 | 2021-04-02 | 长江绿银(无锡)科技有限公司 | Method for extracting allelochemicals and phenylethanoid glycosides compounds from Plantago asiatica |
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Application publication date: 20120111 |