CN1706859A - Process of preparing high-purity jasminodin with Cape jasmine fruit - Google Patents
Process of preparing high-purity jasminodin with Cape jasmine fruit Download PDFInfo
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Abstract
The present invention relates to medicine technology, and is especially the preparation process of preparing jasminodin with cape jasmine fruit. The preparation process includes soaking or refluxing cape jasmine fruit with water or water solution of ethanol to obtain coarse extract; eluting in macroporous adsorbing resin first with great amount of water and then with 10 % concentration ethanol solution to eliminate strong polar iridoid glycoside components and other impurities; selectively eluting jasminodin with low concentration ethanol solution; and decompression concentrating to obtain high purity jasminodin. The preparation process of the present invention has simple operation, low cost, high product purity, no environmental pollution and high yield, and is suitable for industrial production.
Description
Technical field
The present invention relates to medical technical field, is a kind of method for preparing high-purity gardenoside from cape jasmine fruit.
Background technology
Cape jasmine has another name called SHANZHIZI, is the fruit of madder wort mountain Cape jasmine Gardenia jasminoides Ellis., and the property bitter cold is nontoxic.The cape jasmine beginning is stated from Shennong's Herbal, has cholagogic, short pancreatic secretion, step-down, calmness, cooling, antimicrobial antiphlogistic effect.The main chemical compositions of cape jasmine is iridoid, flavones, triterpene, organic acid acetic etc., also have d-N.F,USP MANNITOL, sterols, triterpene saponin, long chain alkane, alcohol and pigment etc. in addition, wherein the iridoid glycoside compounds is [Wang Gangli such as its main active ingredient such as jasminoidin, genipin-1-β-D-gentiobiose glycosides, Gardenoside, gardoside, fevervine time glycosides methyl esters, deacetylate psyllium acid methyl esters, cape jasmine thuja acid, gardenin, Chen Dechang etc. Gardenia Ellis plant chemical ingredient progress. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 1996,21 (2): 67; Huang Shengyang. Chinese Gardenia Ellis Study on plants overview. Jiangxi College of Traditional Chinese Medicine journal, 1991,3 (1): 59].Jasminoidin (geniposide) is main iridoid glycoside compound, is the important effective constituent of cape jasmine, and structural formula is as follows:
Jasminoidin
At present, the traditional method separation and purification jasminoidins such as column chromatography, recrystallization that adopt when preparing jasminoidin with cape jasmine fruit both at home and abroad more, as [Inouye H, et al.Chem Pharm Bull.1970,18 (5): 1066 such as silica gel column chromatography, alumina column chromatography and thin-layer chromatographys; Inouye H, et al.Phytochemistry.1974,13:2219; Endo T, et al.Chem Pharm Bull.1973,21 (12): 2684; The comparison of flourish .TLC of Li Li and column chromatography for separation jasminoidin. Chinese patent medicine .1999,21 (12): 645], these class methods maybe need be used poisonous organic solvent, as chloroform, methyl alcohol, can cause environmental pollution; Or cost height and complex operation, as the neutral alumina filler, cost an arm and a leg.Though also can adopt preparative liquid chromatography to prepare jasminoidin [Wang Lan opens mirror .RP-HPLC preparative chromatography and separates jasminoidin monomer .2003,25 (9): 764], its pre-treating process complex operation is not suitable for large-scale commercial production.There have bibliographical information to adopt macroporous adsorbent resin to separate the jasminoidin cost to be low, do not cause environmental pollution [Lv Maoping, Qiao Qingbin etc. macroporous resin is to the research .2002 of jasminoidin separating effect, 33 (9): 794; CN 1546507A " a kind of Fructus Gardeniae extract and preparation technology thereof and its application "; Jin Rixian, Guo Chunyan etc. the technical study .2005 of jasminoidin in the macroporous adsorbent resin method enrichment cape jasmine, 11 (3): 1], but type of elution commonly used at present has two kinds, one be with behind the water elution directly with the high concentration ethanol wash-out, not only can't remove the iridoid glycoside constituents that polarity is better than jasminoidin slightly, and low-pole impurity is residual more; Two for without washing directly to use the high concentration ethanol wash-out behind the low-concentration ethanol wash-out again, not only can't remove water-soluble impurity, and can introduce more low-pole impurity equally.Therefore, the jasminoidin purity that existing method obtains is lower, still needs to be further purified by above-mentioned traditional separation method, and the application on producing has certain limitation.
Summary of the invention
The invention provides that a kind of preparation technology is simple, the method that from cape jasmine fruit, prepares high-purity gardenoside of low cost and environmentally safe.
The present invention is according to jasminoidin more weak characteristics of relative polarity in the iridoid glycoside constituents, during with purification with macroreticular resin cape jasmine fruit crude extract, earlier with big water gaging and 10% ethanol flush away impurity and the big iridoid glycoside constituents of polarity, low-pole impurity and other iridoid glycosides composition of being introduced with minimizing high concentration ethanol wash-out with 20%～30% ethanol selective elution jasminoidin again.Fact proved that the jasminoidin purity that this simple preparation method obtained is very high, avoided the environmental pollution that causes by other method separation and purification.
The inventive method comprises the steps:
(1) preparation cape jasmine fruit crude extract: routinely dry cape jasmine fruit meal is soaked with water or aqueous ethanolic solution or refluxing extraction 1～3 time, filter, filtrate decompression is concentrated into rare medicinal extract, vacuum-drying gets the cape jasmine fruit crude extract again, and yield is 25%～30%.
(2) prepare jasminoidin: after the above-mentioned cape jasmine fruit crude extract that makes is added the suitable quantity of water suspendible, cross macroporous adsorptive resins.It is colourless that first water respectively and 10% ethanol fully are eluted to elutriant, and water and 10% alcoholic acid elution volume are no less than 4 times of amount of resin usually, discard elutriant, use 20%～30% low-concentration ethanol wash-out again, collect this elutriant, the concentrating under reduced pressure drying promptly gets the jasminoidin powder.Adopt high performance liquid chromatography (HPLC) method that this powder is carried out purity detecting (peak and long-pending normalization method) and record jasminoidin purity and be higher than 98%, yield is 0.5%～1.5%.And carry out MS,
1HNMR and
13CNMR analyzes, and carries out structural confirmation according to the gained data, proves jasminoidin.
The present invention adopts macroporous adsorbent resin only with water and low-concentration ethanol wash-out, with low cost, environment is not polluted, in elution process by water and 10% ethanol gradient elution, remove iridoid glycoside compounds and the impurity that depolarization is better than jasminoidin successively by the polarity size, at last not to be higher than 30% low-concentration ethanol selective elution jasminoidin, reduce the interference of low-pole impurity, need not to be further purified and to obtain purity and be higher than 98% jasminoidin, preparation technology is simple, is fit to suitability for industrialized production.
Description of drawings
Fig. 1 is the color atlas of the high performance liquid chromatography (HPLC) of jasminoidin of the present invention
Embodiment
Describe the present invention below in conjunction with embodiment and accompanying drawing.
Embodiment 1:
1. prepare the cape jasmine fruit crude extract: get dry cape jasmine fruit medicinal material coarse powder 500g, measure 50% alcohol reflux 2 times, each 2 hours with 10 times, filter, merging filtrate, 60 ℃ are evaporated to rare medicinal extract, vacuum-drying gets the cape jasmine fruit crude extract, and yield is 26.6%.
2. purifying: get above-mentioned cape jasmine fruit crude extract, add that cumulative volume is 2000ml behind the water suspendible.Join and 1500g is housed on 1300 pretreated macroporous adsorption resin chromatography posts, absorption was 2 hours after last sample finished.With 6000ml water elution (discarding).Use 8000ml 10% ethanol elution (discarding) again, use 6000ml 20% ethanol elution at last, behind the 20% ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets jasminoidin brown ceramic powder 6.42g, and yield is 1.3%.Adopting high performance liquid chromatography (HPLC) method that this powder is carried out purity detecting (peak area normalization method), to record jasminoidin purity be 98.9%.And carry out MS,
1HNMR and
13CNMR analyzes, and carries out structural confirmation according to the gained data.The HPLC analysis condition is chromatographic column Lichrospher C
18(4.6 * 250mm i.d.5 μ m); Moving phase is acetonitrile: 1% aqueous acetic acid=10: 90; Flow velocity 0.9ml/min; 25 ℃ of column temperatures detect wavelength 238nm.The high-efficient liquid phase chromatogram of jasminoidin is seen Fig. 1 with this understanding, and peak 1 is a jasminoidin.Structure is identified: the jasminoidin that separation is obtained on Varian INOVA-500 type nuclear magnetic resonance analyser and Varian MAT-212 type mass spectrograph, carry out MS,
1HNMR and
13CNMR analyzes, and the result is: UV λ max (nm MeOH): 239.ESI-MS：389(M+1)，227，209(M-glu)。
1HNMR(500MHz，DMSO-d
6)δ：5.12(1H，d，J＝7.0Hz，H-1)，7.5(1H，brs，H-3)，5.6(1H，brs，H-7)，4.2(1H，d，J＝15.0Hz，H-10)，4.0(1H，d，J＝14.0Hz，H-10)，3.6(3H，s，H-12)，4.53(1H，d，J＝8.0Hz，H-1′)。
13CNMR(500MHz，DMSO-d
6)δ：95.7(C-1)，151.5(C-3)，110.9(C-4)，45.9(C-5)，37.9(C-6)，125.4(C-7)，144.1(C-8)，51(C-9)，59.3(C-10)，166.9(C-11)，34.4(C-12)，98.6(C-1′)，73.3(C-2′)，77.2(C-3′)，70(C-4′)，76.6(C-5′)，61(C-6′)。Confirm as jasminoidin through structure elucidation.
Embodiment 2:
1. preparation cape jasmine fruit crude extract: get dry cape jasmine fruit medicinal material coarse powder 500g, with 10 times of water gaging refluxing extraction 2 times, each 2 hours, filtration, merging filtrate, 60 ℃ are evaporated to rare medicinal extract, and vacuum-drying gets the cape jasmine fruit crude extract, and yield is 28.7%.
2. purifying: get above-mentioned cape jasmine fruit crude extract, add that cumulative volume is 2000ml behind the water suspendible.Join and 1500g is housed on 1300 pretreated macroporous adsorption resin chromatography posts, absorption was 2 hours after last sample finished.With 6000ml water elution (discarding).Use 8000ml 10% ethanol elution (discarding) again, use 4000ml 30% ethanol elution at last, behind the 30% ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets jasminoidin brown ceramic powder 7.48g, and yield is 1.5%.Adopting high performance liquid chromatography (HPLC) method that this powder is carried out purity detecting (peak area normalization method), to record jasminoidin purity be 98.0%.Jasminoidin structure authentication method, step and result thereof are with embodiment 1.
Embodiment 3:
1. prepare the cape jasmine fruit crude extract: get dry cape jasmine fruit medicinal material coarse powder 500g, extract each 2 hours 2 times with 10 times of amount 50% alcohol immersion, filter, merging filtrate, 60 ℃ are evaporated to rare medicinal extract, vacuum-drying gets the cape jasmine fruit crude extract, and yield is 20.3%.
2. purifying: get above-mentioned cape jasmine fruit crude extract, add that cumulative volume is 2000ml behind the water suspendible.Join and 1500g is housed on pretreated AB-8 macroporous adsorption resin chromatography post, absorption was 2 hours after last sample finished.With 6000ml water elution (discarding).Use 8000ml 10% ethanol elution (discarding) again, use 6000ml 20% ethanol elution at last, behind the 20% ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets jasminoidin brown ceramic powder 5.36g, and yield is 1.1%.Adopting high performance liquid chromatography (HPLC) method that this powder is carried out purity detecting (peak area normalization method), to record jasminoidin purity be 98.7%.Jasminoidin structure authentication method, step and result thereof are with embodiment 1.
Embodiment 4:
1. prepare the cape jasmine fruit crude extract: get dry cape jasmine fruit medicinal material coarse powder 500g, measure 50% alcohol reflux 2 times, each 2 hours with 10 times, filter, merging filtrate, 60 ℃ are evaporated to rare medicinal extract, vacuum-drying gets the cape jasmine fruit crude extract, and yield is 26.6%.
2. purifying: get above-mentioned cape jasmine fruit crude extract, add that cumulative volume is 2000ml behind the water suspendible.Join and 1500g is housed on pretreated D101 macroporous adsorption resin chromatography post, absorption was 2 hours after last sample finished.With 7000ml water elution (discarding).Use 8000ml 10% ethanol elution (discarding) again, use 5000ml 20% ethanol elution at last, behind the 20% ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets jasminoidin brown ceramic powder 6.23g, and yield is 1.2%.Adopting high performance liquid chromatography (HPLC) method that this powder is carried out purity detecting (peak area normalization method), to record jasminoidin purity be 98.8%.Jasminoidin structure authentication method, step and result thereof are with embodiment 1.
Claims (8)
1. one kind prepares the method for jasminoidin with cape jasmine fruit, comprises the steps:
(1) preparation cape jasmine fruit crude extract: routinely dry cape jasmine fruit meal is soaked with water or aqueous ethanolic solution or refluxing extraction 1～3 time, filter, filtrate decompression is concentrated into rare medicinal extract, vacuum-drying gets the cape jasmine fruit crude extract again;
(2) purifying: after the above-mentioned cape jasmine fruit crude extract that makes added the suitable quantity of water suspendible, cross macroporous adsorbent resin, it is colourless that first water respectively and 10% ethanol fully are eluted to elutriant, discard elutriant, use 20%～30% low-concentration ethanol wash-out again, collect this elutriant, the concentrating under reduced pressure drying promptly gets jasminoidin.
2. prepare the method for jasminoidin by claim 1 is described with cape jasmine fruit, when it is characterized in that preparing the cape jasmine fruit crude extract, use 50% alcohol reflux.
3. describedly prepare the method for jasminoidin with cape jasmine fruit by claim 1 or 2, when it is characterized in that purifying, water and 10% alcoholic acid elution volume all are no less than 4 times of amount of resin.
4. describedly prepare the method for jasminoidin with cape jasmine fruit by claim 1 or 2, when it is characterized in that purifying, said low-concentration ethanol is 20% ethanol.
5. prepare the method for jasminoidin by claim 3 is described with cape jasmine fruit, when it is characterized in that purifying, said low-concentration ethanol is 20% ethanol.
6. describedly prepare the method for jasminoidin by claim 1 or 2 or 5, it is characterized in that said macroporous adsorbent resin is 1300 or D101 or AB-8 type macroporous adsorbent resin with cape jasmine fruit.
7. prepare the method for jasminoidin by claim 3 is described with cape jasmine fruit, it is characterized in that said macroporous adsorbent resin is 1300 or D101 or AB-8 type macroporous adsorbent resin.
8. prepare the method for jasminoidin by claim 4 is described with cape jasmine fruit, it is characterized in that said macroporous adsorbent resin is 1300 or D101 or AB-8 type macroporous adsorbent resin.
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