CN106496292A - A kind of method for preparing 6 iridoid glycoside constituents from Fructus Gardeniae simultaneously - Google Patents
A kind of method for preparing 6 iridoid glycoside constituents from Fructus Gardeniae simultaneously Download PDFInfo
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Abstract
The invention provides a kind of efficiently quick method for preparing 6 iridoid glycoside constituents from Fructus Gardeniae simultaneously, the method is by cape jasmine fruit ethanol extract, the operation of 3 steps such as isolate and purify through macroporous adsorbent resin rough segmentation, anti-phase middle pressure preparative liquid chromatography enrichment flow point and reversed phase high-pressure, you can obtain the monomeric compound that 6 purity are up to more than 95%.The method can expand laboratory and separate scale, improve purification efficiency.Preparation process is simple of the present invention, low cost, extraction efficiency are high, it is most important that, without waste, crystallization purity is high for sample.
Description
Technical field
The invention belongs to the field of Chinese medicines, it is related in a kind of Fructus Gardeniae from Chinese medicine efficiently while 6 monomeric compounds such as the isolation and purification method of 6 kinds of iridoid glycoside constituents of preparation, main separation and purification deacetyl asperulosidic acid methyl ester, Gardenoside, Flos Ixorae Chinensis (Cacumen et Folium Clerodendri paniculati) glycosides, Herba Paederiae time glycosides methyl ester, genipin -1- β-D- gentiobioside with cape jasmine and geniposide.
Background technology
Fructus Gardeniae is Maguireothamnus speciosus Fructus Gardeniae（Gardenia jasminoidesEllis ）Dry mature fruit, with purging intense heat relieving restlessness, clearing away heat-damp and promoting diuresis, removing pathogenic heat from blood and toxic substance from the body, effect of externally used detumescence pain relieving.Pharmaceutical research shows, the effects such as Fructus Gardeniae has antipyretic calm, hepatic cholagogic, is clinically used for treating acute icterohepatitisshock, pain relieving, bruise, coronary heart disease etc..
Main pharmacodynamics composition of the iridoid constituents with geniposide as representative as Fructus Gardeniae, including Herba Paederiae time glycosides methyl ester, Gardenoside, deacetyl asperulosidic acid methyl ester, genipin -1- β-D- gentiobioside with cape jasmine etc., there is many pharmacologically actives such as liver protection, antiinflammatory《Chinese Pharmacopoeia》The qualitative and quantitative analysis method with jasminoidin as reference substance is recorded.With the further investigation to Fructus Gardeniae, the method in the urgent need to developing a kind of multiple iridoid constituents of high efficiency separation purification from Fructus Gardeniae, so as to lay the foundation for the quality evaluation of Fructus Gardeniae, effective substance research, clinical practice and the deep research and development of Fructus Gardeniae related preparations.But such constituent structure is similar to, and polarity is close, water solublity is big, and stability is poor, isolates and purifies more difficult.
At present, having been reported that extraction purification iridoid glycoside constituents from Fructus Gardeniae more, traditional separation method, adopt column chromatography more, separated with toxic organic solvents eluting, time-consuming, and high cost, purity are not ideal enough, easily causes environmental pollution.Chinese patent（A kind of method that cape jasmine fruit prepares high-purity gardenoside, CN1706859A）Using macroporous adsorbent resin, low-concentration ethanol selective elution, one monomer component of jasminoidin that purity is 98.9% is only obtained.Chinese patent（The method that jasminoidin, genipin -1- β-D- gentiobioside with cape jasmine are prepared with cape jasmine fruit, CN1706858A）Using macroporous resin, high speed adverse current chromatogram and the method that combines of liquid phase is prepared, only isolated jasminoidin, genipin -1- β-D- 2 high-purity compositions of gentiobioside with cape jasmine, and in a large number using organic solvents such as ethyl acetate, n-butyl alcohol.Chinese patent（A kind of method for extracting deacetyl asperulosidic acid methyl ester and Herba Paederiae time glycosides methyl ester, CN103242390A）Liquid phase separation is prepared by macroporous resin remove impurity, silicagel column elution remove impurity and mesolow and obtains deacetyl asperulosidic acid methyl ester and Herba Paederiae time glycosides 2 monomer constituents of methyl ester, operating process is loaded down with trivial details, and has pollution to environment.Chinese patent（A kind of method of use preparing total iridoid glycoside with cape jasmine fruit, CN1706860A）Using macroporous resin, the method for low-concentration ethanol eluting, the purity for obtaining iridoid glycoside is 85.7%, and the wherein content of jasminoidin is 55-65%, does not obtain monomeric compound of the purity more than more than 95%.Chinese patent（Capejasmine cycloolefines ether terpene total extract and its production and use, CN1517326A）Iridoid total extract is obtained by ethanol percolation, alcohol reflux or water decocting method, the extraction process is more extensive, do not obtain the such as monomeric compound such as geniposide.Chinese patent（The method for separating and concentrating of iridoid glycoside and crocin, CN101012248A in cape jasmine fruit）Separated by macroporous resin, the enrichment of 30% ethanol gradient elution obtains iridoid glycosideses component, yield is 6.5%, wherein Determination of Gardenoside is 65%, 60% ethanol gradient elution obtains crocin class component, yield is 4.5%, and wherein the content of crocin I is 13%, does not obtain highly purified monomer constituents.Above-mentioned several method is only capable of obtaining one kind or a few iridoid glycoside constituents, cumbersome, yet there are no the method for synchronously preparing 6 kinds of iridoid glycoside constituents from Fructus Gardeniae.
The present invention is with cape jasmine fruit ethanol extract as raw material, the 3 step high efficiency separation such as purification, purification are prepared by macroporous adsorptive resins crude separation, the enrichment of anti-phase medium pressure liquid chromatography and reverse-phase HPLC, on-line checking collects corresponding stream part, lyophilization, you can while obtaining iridoid glycoside constituents of 6 purity more than 95%.
Content of the invention
Present invention aims to the deficiencies in the prior art; provide that a kind of process is simple, fractional dose be big, low cost, the method for quickly preparing multiple high-purity Fructus Gardeniae iridoid glycoside constituents of easy scale; isolate and purify through 3 steps and be obtained 6 monomeric compounds such as highly purified Herba Paederiae time glycosides methyl ester, Gardenoside, Flos Ixorae Chinensis (Cacumen et Folium Clerodendri paniculati) glycosides, deacetyl asperulosidic acid methyl ester, genipin -1- β-D- gentiobioside with cape jasmine and geniposide, technical method is simple, novel, efficient.
For achieving the above object, the present invention employs the following technical solutions to implement：
1. the preparation of Fructus Gardeniae ethanol extract：Cape jasmine fruit coarse granule is taken, with the alcohol reflux of 40-60%, as far as possible the chemical composition in Fructus Gardeniae is extracted completely, is filtered, merging filtrate.Decompression recycling ethanol obtains Fructus Gardeniae ethanol extract extractum to without alcohol taste.
2. macroporous adsorptive resins are separated：After Fructus Gardeniae ethanol extract extractum is taken with suitable quantity of water dispersing and dissolving, separated by macroporous adsorptive resins, order is with water, the water-ethanol gradient elution of variable concentrations, collect each eluting position, appropriate concentration, relative analyses are detected through HPLC, concentrates position concentrating under reduced pressure, lyophilization to obtain yellowish-brown powder iridoid glycoside constituents.
3. suppress standby liquid phase separation to be enriched with：Take yellowish-brown powder to dissolve with appropriate dilute methanol, with the chromatographic separation condition for optimizing, by the anti-phase middle compactings of ODS for post separation, on-line checking, collect main chromatographic peak, decompression and solvent recovery, lyophilization.Analyze through HPLC, obtain corresponding stream part enrichment positions and 2 monomeric compounds.
4. high pressure prepares liquid phase separation and prepares：The position that standby for middle compacting liquid phase enrichment is obtained, with the chromatographic separation condition for optimizing, by reversed phase high-pressure liquid phantom preparing chromatogram post separation, on-line checking, sequentially collects 4 chromatographic peaks by peak, respectively decompression and solvent recovery, lyophilization.Purity is detected with HPLC area normalization methods, 4 monomeric compounds are obtained.
5. compound structure identification：Detected with NMR and reference substance counter point, identify the structure of 6 compounds.
Of the invention compared with the existing method for preparing iridoid glycoside constituents from Fructus Gardeniae, with following technical advantage：
（1）Present invention process flow process is simple, easy to operate, with strong points, and separation efficiency is high.
Fructus Gardeniae ethanol extract is separated by macroporous adsorptive resins, prepares the operation of 3 steps such as liquid phase separation in conjunction with anti-phase middle high-pressure, you can separate from Fructus Gardeniae and prepare 6 iridoid glycoside constituents, and technological process is simpler.Tested and analyzed with macroporous adsorptive resins separating and combining HPLC, step locking iridoid methods of glycosides target eluting position, and the remove impurity through water elution position, reduce the pollution of the standby liquid-phase chromatographic column of next step centering compacting；Anti-phase middle high-pressure preparative liquid chromatography has quick, efficient, on-line real time monitoring, and target component is with strong points, and the monomeric compound purity of preparation is high；Compared with repeatedly separating repeatedly with conventional silica gel column chromatography, a large amount of losses of the target component caused due to extremely adsorbing are reduced, it is to avoid the use of a large amount of toxic organic solvents, thus substantially increase separation efficiency.
（2）The reliable and stable economy of technological means that the present invention is adopted, favorable reproducibility, are suitable for amplifying scale up test, with preferable application prospect.
Macroporous adsorbent resin is inexpensive, renewable use, anti-phase column packing can Reusability, middle high-pressure reversed phase chromatography is easily enlarged preparative separation scale, is suitable to large-scale production.
Description of the drawings
HPLC chromatograms of the Fig. 1 for Fructus Gardeniae ethanol extract macroporous adsorbent resin different solvents eluting position；
Fig. 2 is that the anti-phase middle of 30% alcohol elution suppresses standby liquid chromatogram；
Reversed phase high-pressure preparative liquid chromatography figures of the Fig. 3 for aminoacyl site；
Fig. 4 is the HPLC purity analysis of 6 compounds；
Fig. 5 is the structural formula of 6 compounds；
Fig. 6 is from Fructus Gardeniae while the separating technology flow chart of 6 iridoid glycoside constituents of preparation.
Specific embodiment
Technical solution of the present invention is described in detail in conjunction with embodiment and accompanying drawing, embodiment is only limitted to the explanation present invention, but protection domain is not limited by this.
1. the preparation of Fructus Gardeniae ethanol extract：Take cape jasmine fruit and pulverize into coarse granule, with the alcohol reflux 3 times of 10 times of amounts 50%, each 1.0h, filter, merging filtrate.Decompression recycling ethanol obtains the Fructus Gardeniae ethanol extract extractum of 1g/mL to without alcohol taste.
2. macroporous adsorptive resins are separated and detection iridoid glycoside concentrates position
（1）After Fructus Gardeniae ethanol extract extractum is taken with suitable quantity of water dispersing and dissolving, separated by HPD-100 macroporous adsorptive resins, with the water of 10 times of amount column volumes, 30% ethanol, 50% ethanol, 70% ethanol, 95% ethanol gradient elution, collect each eluting position, concentrating under reduced pressure, lyophilization obtain the powder at different eluting positions.
（2）HPLC detects relative analyses
The preparation of test sample：Take Fructus Gardeniae and macroporous adsorptive resins difference eluting position powder is each appropriate, dissolved with methanol, cross 0.22 μm of microporous filter membrane, standby.
HPLC is analyzed：Shimadzu LC20-AT high performance liquid chromatograph（Quaternary gradient pump, DAD detectors, on-line degassing machine, automatic sampler）, chromatographic column is Agilent TC（2）C18 posts（4.6 mm × 250 mm, 5 μm）；Mobile phase is 0.2% formic acid water（A）Acetonitrile（B）Gradient elution：0~30min (94%→94% A), 30~40min(94%→83% A), 40~48min (83%→80% A), 48~55min (80%→78% A), 55~60min (78%→73% A), 60~75min (73%→68% A), 75~82min (68%→66% A), 82~85min (66%→64% A), 85~95min (64%→61% A), 95~100min (61%→50% A), 100~105min (50%→0% A)；Detection wavelength 238nm；40 DEG C of column temperature；Flow velocity：1ml/min；10 μ L of each test sample sample introduction.
As a result：The characteristic absorption of iridoid glycoside constituents is 238nm, from the point of view of according to different eluting positions paste-forming rate and HPLC collection of illustrative plates relative analyses, iridoid glycoside constituents focus primarily upon 30% alcohol elution, freeze-dried obtain yellowish-brown powder, therefore next further isolate and purify mainly for the position.Concrete outcome is shown in accompanying drawing 1.
3. standby liquid phase enrichment stream part A is suppressed in, separate 2 monomeric compounds
（1）The preparation of sample solution to be separated：Weigh 30% isolated ethanol position of macroporous resin（Yellowish-brown powder）10g, is dissolved to 20mL with 10% methanol, obtains the sample solution of 0.5g/ml, after crossing 0.22 μm of microporous filter membrane, standby.
（2）Middle compacting is for liquid phase separation chromatographic condition：LC-3000 mesohighs prepare liquid phase all-in-one（Binary gradient pump, UV-detector, six-way valve, quantitative loop 10mL）, prepare column length 31cm, internal diameter 2.6cm, anti-phase C18 column packings（Fuji-ODS, 25-40 μm, 130g）；Mobile phase is methanol（A）- water（B）Gradient elution：0 ~ 30.0 min (10% → 10% A), 30.01 ~ 32.0 min (10% → 20% A), 32 ~ 60.0 min (20% → 20% A), 60.01 ~ 65.0 min (20% → 30% A), 65.1 ~ 160.0 min (30% → 30% A)；Detection wavelength 238nm；Flow velocity：5.0ml/min；Sample size 5.0mL.
（3）Sample separation and concentration：On the anti-phase middle compression leg that the injection of 5.0mL sample solutions has been balanced, with above-mentioned chromatographic separation condition on-line checking, the chromatographic peak for detecting is collected according to appearance time and order successively.According to the standby liquid chromatogram of middle compacting, three big chromatographic peaks such as A, B, C are mainly collected, concrete outcome is shown in accompanying drawing 2.
（4）Compound purity is analyzed：HPLC methods, Shimadzu LC20-AT high performance liquid chromatograph, chromatographic column, Detection wavelength, flow velocity, column temperature same 2.（2）Under；Mobile phase is acetonitrile（A）- 0.2% formic acid water（B）Gradient elution：0~22min A（6%→6%）, 22 ~ 32min A（6%→17%）, 32 ~ 38min A（17%→20%）.Under the HPLC analysis conditions, stream part A is a mixture, awaits further separating.Collect stream part B and C is evaporated in right amount respectively, detect through HPLC areas of peak normalization method, purity is respectively 90.12% and 93.25%；White powder is respectively obtained with recrystallizing methanol, the purity of 2 compounds is improved to 97.12% and 98.70%.Concrete outcome is shown in accompanying drawing 4.
4. high pressure preparation solution synchronised is separated and prepares 4 monomeric compounds
（1）The preparation of A stream part sample solutions：Take the A stream parts sample after concentration appropriate, the sample solution for being prepared into 0.5mg/ml is dissolved with 10% methanol, after crossing 0.22 μm of microporous filter membrane, standby.
（2）High pressure prepares liquid phase separation chromatographic condition：LC-3000 mesohighs prepare liquid phase all-in-one, YMC high pressure preparative hplc posts (250 mm × 20 mm, 5 μm)；Mobile phase is 6% acetonitrile isocratic elution；Detection wavelength 238nm；Flow velocity：5.0ml/min；Sample size 1.0mL.
（3）Sample is separated and is prepared：According to the chromatographic separation condition of above-mentioned optimization, sample introduction, on-line checking, are collected successively according to appearance time and order in accordance with the law, and A stream parts collect 4 chromatographic peaks such as A1, A2, A3, A4 altogether, respectively decompression and solvent recovery, and lyophilization obtains white powder.Concrete outcome is shown in accompanying drawing 3.
（4）Compound purity is analyzed：HPLC methods, with 3.（4）Chromatographiccondition under.Detect that as a result 4 monomeric compound purity are respectively 97.89%, 98.12%, 95,45% and 96.34% with HPLC area normalization methods.Concrete outcome is shown in accompanying drawing 4.
5. the Structural Identification of preparative separation compound：Determine through NMR and compare with the Data Comparison of document report and with known reference substance, 6 compounds are identified respectively as acetyl asperuloside acid methyl ester（A1, compound 1）, Gardenoside（A2, compound 2）, Flos Ixorae Chinensis (Cacumen et Folium Clerodendri paniculati) glycosides（A3, compound 3）, Herba Paederiae time glycosides methyl ester（A4, compound 4）, genipin -1- β-D- gentiobioside with cape jasmine（B, compound 5）And geniposide（C, compound 6）Deng 6 compounds.Structural formula of compound concrete outcome is shown in accompanying drawing 5.
6. it should be pointed out that specific embodiment is the more representational example of the present invention, it is clear that technical scheme is not limited to above-described embodiment.The concrete outcome of separation process of the present invention is shown in accompanying drawing 6.
Claims (10)
1. a kind of method of 6 iridoid glycoside constituents of efficiently purifying from Fructus Gardeniae, follows the steps below：Fructus Gardeniae is pulverized into coarse granule, is extracted with aquiferous ethanol, united extraction liquid concentrating under reduced pressure is flung to ethanol and obtains extractum；After extractum is with suitable quantity of water dispersing and dissolving, separated using macroporous adsorbent resin, first with water elution after, then water-ethanol eluting in varing proportions collects eluent, concentration, and lyophilization, the eluting position that iridoid glycoside constituents are concentrated are yellowish-brown powder；Yellowish-brown powder is dissolved with suitable quantity of water or dilute methanol solution, microporous filter membrane（0.22μm）Filter, the preparative liquid chromatography initial gross separation of anti-phase middle pressure, methanol-water system gradient elution of the mobile phase for low concentration, Detection wavelength 238nm, on-line monitoring collect 3 main chromatographic peaks, concentration, lyophilization by figure；Analyze through HPLC, first chromatographic peak is mixture, pale powder, second, third chromatographic peak are respectively monomer component of the content more than 90%, reach more than 95% through recrystallizing methanol purity, and its outward appearance is white powder；By be enriched to first chromatographic peak（Pale powder）Dissolved with suitable quantity of water or dilute methanol solution, microporous filter membrane（0.22μm）Filter, reversed phase high-pressure preparative liquid chromatography is separated again, acetonitrile isocratic elution of the mobile phase for low concentration, Detection wavelength 238nm, collects 4 chromatographic peak flow points, concentration according to collection of illustrative plates, lyophilization, you can obtain iridoid glycoside constituents of 4 contents more than 95%, be white powder.
2. according to claims 1, it is characterised in that：Step（1）In Extraction solvent used be 40-60% ethanol, solubilization dosage is measured for 5-10 times of sample, and the heating and refluxing extraction time is 1-2 hours, and extraction time is 2-3 time, is concentrated into 1-2g crude drugs/mL.
3. according to claims 1, it is characterised in that：Step（2）In resin used be D101, HPD-100, HP-20 or AB-8.
4. according to claims 1, it is characterised in that：Step（2）Respectively according to water, 20-35% ethanol, 45-55% ethanol, 65-75% ethanol, 90-98% ethanol successively eluting, the volume of each gradient elution is 6-10 times of column volume to middle eluting solvent.
5. according to claims 1, it is characterised in that：Step（2）Alcohol elution of the eluting position that middle iridoid methods of glycosides is concentrated for 20-35%.
6. according to claims 1, it is characterised in that：Step（3）In prepare column packing for C18 used by the standby liquid phase initial gross separation of anti-phase middle compacting, 25-75 μm of particle diameter prepares column length 30-100cm, internal diameter 2-4cm.
7. according to claims 1, it is characterised in that：Step（3）The methanol elution gradient mode of middle low concentration is 10% methanol, 20% methanol, 30% methanol difference eluting 30-35min, 30-35min, 80-120min, and flow velocity is 5-20mL/min, and on-line monitoring collects chromatographic peak.
8. according to claims 1, it is characterised in that：Step（3）In obtain 2 high-purity compositions (geniposide and genipin O-gentibioside), can reach more than 95% through recrystallization purity.
9. according to claims 1, it is characterised in that：Step（4）In anti-phase prepare liquid phase isolate and purify again used prepare column packing for C18,5-10 μm of particle diameter prepares column length 25-30cm, internal diameter 1.5-4cm.
10. according to claims 1, it is characterised in that：Step（4）In mobile phase used be 5-10% acetonitrile isocratic elutions, flow velocity is 2-10mL/min, collects by appearance number and appearance time and obtains 4 contents and reach more than 95% high-purity composition（10-deacetyl asperulosidic sweet acid methyl ester, Gardenoside, Flos Ixorae Chinensis (Cacumen et Folium Clerodendri paniculati) glycosides, Herba Paederiae time glycosides methyl ester）.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106993687A (en) * | 2017-05-09 | 2017-08-01 | 福建岳海水产食品有限公司 | A kind of preparation method of jasmine tea |
| CN107412040A (en) * | 2017-05-09 | 2017-12-01 | 宁德市容海水产有限公司 | A kind of cape jasmine facemask powder and preparation method thereof |
| CN109464514A (en) * | 2018-11-19 | 2019-03-15 | 中国中医科学院中药研究所 | A kind of capejasmine extract that treating hyperbileacidemia and its preparation and application |
| CN113735923A (en) * | 2021-09-26 | 2021-12-03 | 中国中医科学院中药研究所 | Dimer iridoid glycoside and preparation method and application thereof |
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2015
- 2015-09-08 CN CN201510563412.0A patent/CN106496292A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106993687A (en) * | 2017-05-09 | 2017-08-01 | 福建岳海水产食品有限公司 | A kind of preparation method of jasmine tea |
| CN107412040A (en) * | 2017-05-09 | 2017-12-01 | 宁德市容海水产有限公司 | A kind of cape jasmine facemask powder and preparation method thereof |
| CN106993687B (en) * | 2017-05-09 | 2020-03-27 | 福建岳海水产食品有限公司 | Preparation method of gardenia tea |
| CN107412040B (en) * | 2017-05-09 | 2020-06-16 | 宁德市容海水产有限公司 | Gardenia facial mask powder and preparation method thereof |
| CN109464514A (en) * | 2018-11-19 | 2019-03-15 | 中国中医科学院中药研究所 | A kind of capejasmine extract that treating hyperbileacidemia and its preparation and application |
| CN109464514B (en) * | 2018-11-19 | 2021-09-10 | 中国中医科学院中药研究所 | Gardenia extract for treating hypercholesterolaemia and preparation and application thereof |
| CN113735923A (en) * | 2021-09-26 | 2021-12-03 | 中国中医科学院中药研究所 | Dimer iridoid glycoside and preparation method and application thereof |
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