CN1307191C - Process for preparing jasminodin and genipin-1-beta-D-gentiobioside with cape jasmine fruit - Google Patents
Process for preparing jasminodin and genipin-1-beta-D-gentiobioside with cape jasmine fruit Download PDFInfo
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- CN1307191C CN1307191C CNB2005100261426A CN200510026142A CN1307191C CN 1307191 C CN1307191 C CN 1307191C CN B2005100261426 A CNB2005100261426 A CN B2005100261426A CN 200510026142 A CN200510026142 A CN 200510026142A CN 1307191 C CN1307191 C CN 1307191C
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Abstract
The present invention relates to the technical field of medicine, particularly to a process of separating and purifying jasminodin with high purity and genipin-1-beta-D-gentiobioside from cape jasmine fruit. The process comprises: water or ethanol water solution is used for soaking or refluxing and preparing a crude extract of cape jasmine fruit; a large amount of water firstly is used sufficiently eluting macroporous absorbing resin until eluent is colorless; ethanol with a low concentration is used for elution, decompression and concentration for obtaining a macroporous absorbing resin extract of the cape jasmine fruit; the extract is separated and purified by the combined process of high-speed countercurrent chromatography and the preparation of liquid phase chromatography for obtaining jasminodin with high purity and genipin-1-beta-D-gentiobioside. The preparing process of the present invention has the advantages of high separating efficiency, good product purity and simple and convenient operation, and is suitable for industrial production.
Description
Technical field
The present invention relates to medical technical field, be a kind of from cape jasmine fruit the method for separating and purifying high-purity jasminoidin, genipin-1-β-D-gentiobiose glycosides.
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.Clinical be mainly used in the treatment fever of children, esophagitis and aphtha, turn round and frustrate wound, coronary heart disease, acute viral hepatitis hyperbilirubinemia, acute catarrhal conjunctivitis etc.Its main chemical ingredients 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, (genipin-1-β-D-geniobioside) belongs to the iridoid glycoside compounds to jasminoidin (geniposide) and genipin-1-β-D-gentiobiose glycosides, be the main active ingredient [Wang Gangli in the cape jasmine fruit, 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], their structural formula is as follows:
At present, both at home and abroad prepare jasminoidin and adopt effective monomer in the traditional method separation and purification cape jasmine fruits such as column chromatography and recrystallization more with cape jasmine fruit, these class methods maybe need be used poisonous organic solvent, use chloroform, methyl alcohol as silica gel column chromatography, can cause environmental pollution; Or cost height and complex operation, [Inouye H, et al.Chem Pharm Bull.1970,18 (5): 1066 as little property alumina packing, cost an arm and a leg; Inouye H, et al.Phytochemistry.1974,13:2219; Endo T. et al.ChemPharm Bull.1973,21 (12): 2684], and used stationary phase has the non-reversibility adsorption to sample.[the Wang Lan that adopts preparative liquid chromatography separation and purification jasminoidin is also arranged, open mirror .RP-HPLC preparative chromatography and separate jasminoidin monomer .2003,25 (9): 764], but its pre-treatment still needs by above-mentioned conventional post chromatography, and adopts and repeatedly repeat preparation and carry out purifying and cause the jasminoidin loss more.High speed adverse current chromatogram (High-speed counter-current chromatography HSCCC) is a kind of newer liquid liquid distribution chromatography technology, it need not any solid support or carrier and overcome the non-reversibility adsorption of traditional separation method to sample, thereby sample recovery rate height, also have advantages such as applied range, instrumentation is simple, fractional dose is big simultaneously, but yet there are no the separation and purification that high speed adverse current chromatogram is applied to monomeric compound in the cape jasmine at present both at home and abroad.
Summary of the invention
What the invention provides that a kind of preparation technology is simple fast, the rate of recovery is high, purity is high and be suitable for suitability for industrialized production prepares ten thousand methods of jasminoidin, genipin-1-β-D-gentiobiose glycosides with cape jasmine fruit.
Jasminoidin and genipin-1-β-D-gentiobiose glycosides is the main component in the cape jasmine fruit, in view of its polarity in the iridoid glycoside constituents relatively a little less than, so the present invention uses big water gaging with impurity and strong polarity iridoid glycoside constituents flush away earlier, with the low-concentration ethanol selective elution, obtain jasminoidin and genipin-1-β-D-gentiobiose glycosides content and account for the extract more than 95% again.And then separate and purifying with preparative liquid chromatography with high speed adverse current chromatogram.
The inventive method comprises the steps:
1. prepare the 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. purifying:
(1) uses purification with macroreticular resin: after the above-mentioned cape jasmine fruit crude extract that makes is added the suitable quantity of water suspendible, cross macroporous adsorptive resins.The abundant wash-out of elder generation's water is colourless until elutriant, the elution volume of water is no less than 4 times of amount of resin usually, discard elutriant, use 10%～30% low-concentration ethanol wash-out again, collect elutriant, the concentrating under reduced pressure drying, promptly get extract, detect through high performance liquid chromatography (HPLC), contain 95% above jasminoidin and genipin-1-β-D-gentiobiose glycosides, yield is 4%～6%;
(2) with high speed adverse current chromatogram and preparative liquid chromatography with jasminoidin and genipin-1-β-D-gentiobiose glycosides separation and purification: the solvent system that constitutes high speed adverse current chromatogram stationary phase, moving phase is an ethyl acetate: propyl carbinol: water=2: 1: 3 or 2: 1.5: 3 or propyl carbinol: water=1: 1.Static layering behind the shake well in separating funnel, on be stationary phase mutually, is moving phase mutually down.Make earlier in the counter current chromatograph pillar to be full of stationary phase, main frame is rotated, pump into moving phase again, the extract of getting gained in the step (1) is dissolved in a small amount of phase down, by the sampling valve sample introduction, receives flow point " I ", " II " according to the detector spectrogram.Adopt high performance liquid chromatography that the gained flow point is carried out purity detecting (peak area normalization method), record stream part " II " purity and be higher than 99%, stream part " I " purity is higher than 85%.Use preparative liquid chromatography convection current part " I " separation and purification again, must flow part " III ", detect by above-mentioned high performance liquid chromatography, purity is higher than 99%.Volatilize behind the solvent to flow point " II " " III " carry out MS,
1HNMR and
13CNMR analyzes, and carries out structural confirmation according to the gained data, and flow point " II " is a jasminoidin, and flow point " III " is genipin-1-β-D-gentiobiose glycosides.
The present invention adopts macroporous adsorbent resin that sample is carried out pre-treatment, only makes water and low-concentration ethanol wash-out, and is with low cost, free from environmental pollution; In elution process, because genipin-1-β-D-gentiobiose glycosides and jasminoidin are less than normal at the iridoid Semi-polarity, so at first remove other strong polarity iridoid glycoside constituents with massive laundering, again with the low-concentration ethanol wash-out, obtain containing genipin-1-β-D-gentiobiose glycosides and the extract of jasminoidin more than 95%, simple to operate.Adopt high speed adverse current chromatogram and preparative liquid chromatography that the jasminoidin in this extract and genipin-1-β-D-gentiobiose glycosides are carried out separation and purification at last, method is fast simple and the rate of recovery is high, overcome shortcomings such as traditional preparation process method complex operation, separation cycle be long, and have separation efficiency height, good product purity, easy, be suitable for advantage such as suitability for industrialized production.
Description of drawings
Fig. 1 is the high-efficient liquid phase chromatogram through the extract of purification with macroreticular resin
Fig. 2 is the color atlas through the high speed adverse current chromatogram of the extract of purification with macroreticular resin (HSCCC)
Fig. 3 is the color atlas of the preparative liquid chromatography of genipin of the present invention-1-β-D-gentiobiose glycosides
Fig. 4 separates flow point " I " (the separating obtained stream part that contains genipin-1-β-D-gentiobiose glycosides of high-speed counter-current) high-efficient liquid phase chromatogram for HSCCC
Fig. 5 is preparative liquid chromatography flow point " III " (genipin-1-β-D-gentiobiose glycosides) high-efficient liquid phase chromatogram
Fig. 6 is HSCCC separated flow part " II " (jasminoidin) high-efficient liquid phase chromatogram
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, with 10 times of amount 50% alcohol reflux 2 times, each 2 hours, filter, merging filtrate, 60 ℃ are evaporated to rare medicinal extract, and vacuum-drying gets the cape jasmine fruit crude extract, and yield is 29.8%.
2. purifying:
(1) uses purification with macroreticular resin: 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 6000ml 20% ethanol elution again, behind the ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets extract powder 29.51g, and yield is 5.9%, detects through HPLC, and its jasminoidin and genipin-1-β-D-gentiobiose glycosides total content is 95.3%.
(2) use high speed adverse current chromatogram (Shenzhen is with the biochemical company limited in field) and preparative liquid chromatography with jasminoidin and genipin-1-β-D-gentiobiose glycosides separation and purification: the solvent system of formation high speed adverse current chromatogram stationary phase, moving phase is an ethyl acetate: propyl carbinol: water=2: 1: 3.Static layering behind the shake well in separating funnel, on be stationary phase mutually, is moving phase mutually down.Make earlier in the counter current chromatograph pillar and be full of stationary phase, main frame is rotated, pump into moving phase again, the adverse current chromatogram column volume is 300ml, stationary phase retention rate 60%, flow velocity 2.0ml/min, rotating speed 800rpm detects wavelength 254nm, get during the extract obtained powder 300mg of step (1) is dissolved under the 10ml mutually, by the sampling valve sample introduction, receive flow point " I ", " II " according to the detector spectrogram, see Fig. 1.It is single chromatographic peak that this part is carried out HPLC analysis revealed " II ", and peak purity is 99.7%, and stream part " I " purity is 87.6%.Use preparative liquid chromatography separation and purification stream part " I " again.The HPLC preparation condition is chromatographic column YWG C
18(10.0 * 200mm i.d.10 μ m); Moving phase is acetonitrile: water=10: 90; Flow velocity 2.0ml/min; 25 ℃ of column temperatures; Detect wavelength 238nm.According to detector spectrogram receiving target composition, get flow point " III ", this flow point is carried out high-efficient liquid phase analysis show that it is single chromatographic peak, peak purity is 99.8%.Preparative liquid chromatography figure sees Fig. 2.The HPLC analysis condition is chromatographic column Lichrospher C
18(4.6 * 250mmi.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.Each high-efficient liquid phase chromatogram of gained is seen Fig. 3, Fig. 4, Fig. 5, Fig. 6 with this understanding, and wherein peak 1 is genipin-1-β-D-gentiobiose glycosides, and peak 2 is a jasminoidin." II ", " III " flow point that separation is obtained volatilize, and get flow point " II " yellow powder 209.4mg, and yield is 4.1%; Flow point " III " yellow powder 47.1mg, yield is 0.9%.Flow point " II ", " III " on VarianINOVA-500 type nuclear magnetic resonance analyser and Varian MAT-212 type mass spectrograph, are carried out
1HNMR,
13CNMR and MS analyze, and determine that through structure elucidation flow point II is a jasminoidin, and flow point III is genipin-1-β-D-gentiobiose glycosides.The gained data are: flow point " II " UV λ max (nm MeOH): 239.ESI-MS：389(M+1)，227，209(M-glu)。
1HNMR(500?MHz，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′)。Flow point " III " UV λ max (nm MeOH): 239.ESI-MS：549(M-H)，573(M+Na)。
1HNMR(500?MHz，DMSO-d
6)δ：5.12(1H，d，J＝8.0Hz，H-1)，7.5(1H，brs，H-3)，5.7(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′)，4.24(1H，d，J＝8.0Hz，H-1＂)。
13CNMR(500?MHz，DMSO-d
6)δ：96.4(C-1)，151.4(C-3)，110.6(C-4)，45.5(C-5)，37.9(C-6)，125.9(C-7)，143.9(C-8)，50.8(C-9)，59.2(C-10)，166.8(C-11)，34.6(C-12)，98.9(C-1′)，73.5(C-2′)，76.5(C-3′)，70.1(C-4′)，76.5(C-5′)，68(C-6′)，103.2(C-1＂)，76.5(C-2")，73(C-3＂)，70(C-4")，76.5(C-5")，61(C-6＂)。
Embodiment 2:
1. prepare the 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, filter, 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:
(1) uses purification with macroreticular resin: get above-mentioned cape jasmine fruit crude extract, add that cumulative volume is 2000ml behind the water suspendible.Join dress row 1500g on pretreated AB-8 macroporous adsorption resin chromatography post, absorption was 2 hours after last sample finished.With 7000ml water elution (discarding).Use 4000ml 30% ethanol elution again, behind the ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets cape jasmine fruit macroporous adsorbent resin extract powder 32.88g (jasminoidin and genipin-1-β-D-gentiobiose glycosides accounts for 94.5%), and yield is 6.6%.
(2) use high speed adverse current chromatogram (Shenzhen is with the biochemical company limited in field) and preparative liquid chromatography with jasminoidin and genipin-1-β-D-gentiobiose glycosides separation and purification: the solvent system of formation high speed adverse current chromatogram stationary phase, moving phase is an ethyl acetate: propyl carbinol: water=2: 1.5: 3.The method that the separation and purification of jasminoidin and genipin-1-β-D-gentiobiose glycosides, purity detecting and structure are identified, step are with embodiment 1.The jasminoidin yield is 4.3%, and purity is 99.6%; Genipin-1-β-D-gentiobiose glycosides yield is 1.1%, and purity is 99.7%.
Embodiment 3:
1. prepare the cape jasmine fruit crude extract:
Get dry cape jasmine fruit medicinal material coarse powder 500g, extract 2 times with 10 times of amount 50% alcohol immersion, each 2 hours, filter, merging filtrate, 60 ℃ are evaporated to rare medicinal extract, and vacuum-drying gets the cape jasmine fruit crude extract, and yield is 20.3%.
2. purifying:
(1) uses purification with macroreticular resin: 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.Earlier with 6000ml water elution (discarding).Use 8000ml 10% low-concentration ethanol wash-out again, behind the ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets cape jasmine fruit macroporous adsorbent resin extract powder 23.47g (jasminoidin and genipin-1-β-D-gentiobiose glycosides accounts for 97.5%), and yield is 4.7%.
(2) use high speed adverse current chromatogram (Shenzhen is with the biochemical company limited in field) and preparative liquid chromatography with jasminoidin and genipin-1-β-D-gentiobiose glycosides separation and purification: the solvent system of formation high speed adverse current chromatogram stationary phase, moving phase is a propyl carbinol: water=1: 1.The method that the separation and purification of jasminoidin and genipin-1-β-D-gentiobiose glycosides, purity detecting and structure are identified, step are with embodiment 1.The jasminoidin yield is 3.9%, and purity is 99.8%; Genipin-1-β-D-gentiobiose glycosides yield is 0.7%, and purity is 99.9%.
Embodiment 4:
1. prepare the cape jasmine fruit crude extract:
Get dry cape jasmine fruit medicinal material coarse powder 500g, with 10 times of amount 50% alcohol reflux 2 times, each 2 hours, filter, merging filtrate, 60 ℃ are evaporated to rare medicinal extract, and vacuum-drying gets the cape jasmine fruit crude extract, and yield is 29.8%.
2. purifying:
(1) uses purification with macroreticular resin: 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.Earlier with 7000ml water elution (discarding).Use 7000ml 30% ethanol elution again, behind the ethanol elution stream part concentrating under reduced pressure, vacuum-drying (60 ℃) gets cape jasmine fruit macroporous adsorbent resin extract powder 30.23g (jasminoidin and genipin-1-β-D-gentiobiose glycosides accounts for 97.2%), and yield is 6.0%.
(2) use high speed adverse current chromatogram (Shenzhen is with the biochemical company limited in field) and preparative liquid chromatography with jasminoidin and genipin-1-β-D-gentiobiose glycosides separation and purification: the solvent system of formation high speed adverse current chromatogram stationary phase, moving phase is an ethyl acetate: propyl carbinol: water=2: 1: 3.The method that the separation and purification of jasminoidin and genipin-1-β-D-gentiobiose glycosides, purity detecting and structure are identified, step are with embodiment 1.The jasminoidin yield is 4.1%, and purity is 99.7%; Genipin-1-β-D-gentiobiose glycosides yield is 0.9%, and purity is 99.8%.
Claims (8)
1. a method for preparing high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides from cape jasmine fruit comprises the steps:
1.1 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;
1.2 purifying:
1.2.1 use purification with macroreticular resin: after the above-mentioned cape jasmine fruit crude extract that makes added the suitable quantity of water suspendible, cross macroporous adsorbent resin, the abundant wash-out of first water is colourless until elutriant, use 10%～30% low-concentration ethanol wash-out again, collect elutriant, the concentrating under reduced pressure drying gets extract;
1.2.2 with high speed adverse current chromatogram and preparative liquid chromatography with jasminoidin and genipin-1-β-D-gentiobiose glycosides separation and purification: constitute the high speed adverse current chromatogram stationary phase, the solvent system of moving phase is an ethyl acetate: propyl carbinol: water=2: 1: 3 or 2: 1.5: 3 or propyl carbinol: water=1: 1, static layering behind the shake well in separating funnel, on be stationary phase mutually, be moving phase mutually down, make earlier in the counter current chromatograph pillar and be full of stationary phase, main frame is rotated, pump into moving phase again, with the extract of gained among the step 1.2.1 be dissolved in a small amount of down mutually in, by the sampling valve sample introduction, receive flow point " I " according to the detector spectrogram, " II ", use preparative liquid chromatography again to flow point " I " separation and purification, get flow point " III ", flow point " II ", " III " is respectively jasminoidin and genipin-1-β-D-gentiobiose glycosides.
2. prepare the method for high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides 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 high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides with cape jasmine fruit by claim 1 or 2, when it is characterized in that using purification with macroreticular resin, the elution volume of water is no less than 4 times of amount of resin.
4. describedly prepare the method for high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides with cape jasmine fruit by claim 1 or 2, when it is characterized in that using purification with macroreticular resin, said low-concentration ethanol is 20% ethanol.
5. prepare the method for high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides by claim 3 is described with cape jasmine fruit, when it is characterized in that using purification with macroreticular resin, said low-concentration ethanol is 20% ethanol.
6. describedly prepare the method for high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides 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 high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides 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 high-purity gardenoside, genipin-1-β-D-gentiobiose glycosides 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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| CN102000102A (en) * | 2010-11-03 | 2011-04-06 | 南京中医药大学 | Application of genipin-1-beta-D-gentiobioside to preparation of medicament for treating heart failure disease |
| CN102516325B (en) * | 2011-11-15 | 2014-04-09 | 江西中天农业生物工程有限公司 | Method for producing crocin with higher than 95% purity from gardenia |
| CN102875617A (en) * | 2012-09-12 | 2013-01-16 | 安徽医科大学 | Geniposide derivative, preparation method thereof and application of geniposide derivative to inflammation resistance |
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| 中药分离中高速逆流色谱溶剂体系的选择 颜继忠等，中国现代应用药学杂志，第20卷第5期 2003 * |
| 中药栀子提取方法的比较和工艺条件优化 李其兰等，中国医院药学杂志，第24卷第6期 2004 * |
| 天然产物分离技术的新进展 李德江等，天津化工，第18卷第2期 2004 * |
| 天然产物分离技术的新进展 李德江等，天津化工，第18卷第2期 2004;中药分离中高速逆流色谱溶剂体系的选择 颜继忠等，中国现代应用药学杂志，第20卷第5期 2003;中药栀子提取方法的比较和工艺条件优化 李其兰等，中国医院药学杂志，第24卷第6期 2004;栀子苷乙醇提取的方法优化 刘菊芳等，山东中医杂志，第23卷第11期 2001 * |
| 栀子苷乙醇提取的方法优化 刘菊芳等，山东中医杂志，第23卷第11期 2001 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101113156A (en) * | 2007-07-16 | 2008-01-30 | 石任兵 | Method for preparing cape jasmine glycosides standard substance and its analogue |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1706858A (en) | 2005-12-14 |
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