CN103800397B - The technique of macroporous resin purification Herba Ephedrae total alkaloids - Google Patents
The technique of macroporous resin purification Herba Ephedrae total alkaloids Download PDFInfo
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- CN103800397B CN103800397B CN201410047475.6A CN201410047475A CN103800397B CN 103800397 B CN103800397 B CN 103800397B CN 201410047475 A CN201410047475 A CN 201410047475A CN 103800397 B CN103800397 B CN 103800397B
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- 239000011347 resin Substances 0.000 title claims abstract description 32
- 229920005989 resin Polymers 0.000 title claims abstract description 32
- 229930013930 alkaloid Natural products 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000000746 purification Methods 0.000 title claims abstract description 15
- 238000011068 loading method Methods 0.000 claims abstract description 18
- 241001465251 Ephedra sinica Species 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000003480 eluent Substances 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 7
- 238000010828 elution Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 229960002534 ephedrine hydrochloride Drugs 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- ZPLCXHWYPWVJDL-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)methyl]-1,3-oxazolidin-2-one Chemical compound C1=CC(O)=CC=C1CC1NC(=O)OC1 ZPLCXHWYPWVJDL-UHFFFAOYSA-N 0.000 claims description 4
- BALXUFOVQVENIU-GNAZCLTHSA-N Ephedrine hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-GNAZCLTHSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 claims description 3
- FMCGSUUBYTWNDP-UHFFFAOYSA-N N-Methylephedrine Natural products CN(C)C(C)C(O)C1=CC=CC=C1 FMCGSUUBYTWNDP-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002835 absorbance Methods 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 3
- 230000000536 complexating effect Effects 0.000 claims description 3
- 229960002179 ephedrine Drugs 0.000 claims description 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- 229960002221 methylephedrine Drugs 0.000 claims description 3
- 239000008363 phosphate buffer Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims description 3
- 238000002137 ultrasound extraction Methods 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 2
- 238000003828 vacuum filtration Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000003285 pharmacodynamic effect Effects 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 238000003556 assay Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 description 5
- 238000003795 desorption Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000218671 Ephedra Species 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000013558 reference substance Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 102000011759 adducin Human genes 0.000 description 1
- 108010076723 adducin Proteins 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940126678 chinese medicines Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229960003447 pseudoephedrine hydrochloride Drugs 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a kind of technique of macroporous resin purification Herba Ephedrae total alkaloids, comprise the following steps:Three kinds of Contents of Main Components measure, the pretreatment of macroreticular resin, loadings, wash-outs in the preparation of Chinese ephedra extract solution, the assay of Herba Ephedrae total alkaloids, Chinese ephedra, there is provided a kind of optimised process for purifying Herba Ephedrae total alkaloids, it is easy to operate, yield is high, is that further galenic pharmacy and pharmacodynamic study are offered reference.
Description
Technical field
The invention belongs to the field of Chinese medicines, specifically a kind of technique of macroporous resin purification Herba Ephedrae total alkaloids.
Background technology
Chinese ephedraEphedrae HerbaIt is EphedraceaeEphedraceaPlant ephedra sinicaEphedra sinica Stapf, in
Chinese ephedraEphedra intermedia Schrenk et C.A.MeyAnd ephedra equisetinaEphedra equisetina BgeIt is dry
Dry herbaceous stem stem, be《Chinese Pharmacopoeia》The traditional Chinese medicine for recording.Modern study shows that the TA in Chinese ephedra has in excitement
Pivot, antitussive and antiasthmatic, lax tracheae, hypotensive, influence tissue anti-oxidation function, reduction blood sugar[It is that it plays medicine Deng pharmacological action
The active component of effect.
However, the research that isolates and purifies of Herba Ephedrae total alkaloids is rarely reported, only using resin to single group in Chinese ephedra
Point --- ephedrine hydrochloride carries out the investigation of purifying process, not can be shown that the purifying situation to Herba Ephedrae total alkaloids.
The content of the invention
In order to solve the above-mentioned technical problem, the invention provides a kind of technique of macroporous resin purification Herba Ephedrae total alkaloids.
A kind of technique of macroporous resin purification Herba Ephedrae total alkaloids, it is characterised in that comprise the following steps:
1)Precision weighs Chinese ephedra fine powder in right amount, 8 times of 0.5% aqueous hydrochloric acid solutions of amount of addition, 60 DEG C, 250W ultrasonic extraction 1h,
Suction filtration, required concentration is concentrated under reduced pressure into Rotary Evaporators;
2)Precision draws appropriate Chinese ephedra need testing solution, sequentially adds 7.5 phosphate buffer 1s of pH 0 mL, 0.05%
The mL of bromothymol blue solution 4, after 3 min of complexing, adds 10 mL chloroforms to be extracted twice every time, divides and takes chloroform layer, determines 416
Absorbance at nm wavelength, is control with ephedrine hydrochloride, calculates the content of TA;
3)Appropriate Chinese ephedra need testing solution is taken, HPLC analyses are carried out, ephedrine, d-pseudo-ephedrine, methylephedrine is determined
Three kinds of contents of main component;
4)Macroreticular resin is placed in beaker, 24 h are soaked with 95% ethanol, it is fully expanded, 95 % are added after suction filtration
Ethanol washing macroreticular resin to cleaning solution adds appropriate distilled water without white opacity phenomenon, then cleans ethanol with distilled water, and vacuum is taken out
It is standby after filter;
5)Loading, wash-out, wherein loading liquid pH are 5-6, and sample concentration is 0.1-0.15 g mL-1, loading flow velocity is
0.3—0.7 mL•min-1, eluant, eluent volume is 7.5-8 BV, and eluant, eluent is 95% ethanol, and elution flow rate is 0.8-1.2
mL•min-1。
A kind of technique of described macroporous resin purification Herba Ephedrae total alkaloids, it is characterised in that step 3)Middle chromatographic condition
For:Chromatographic column Agilent Zorbax SB-C18(250 mm × 4.6 mm, 5 μm), 0.1% phosphoric acid:Acetonitrile=95:5, detect ripple
A length of 210 nm;30 DEG C of column temperature;The mL min of flow velocity 1-1, the μ L of sample size 20.
A kind of technique of described macroporous resin purification Herba Ephedrae total alkaloids, it is characterised in that step 4)Described in macropore
Resin is HPD100 type macroreticular resins.
A kind of technique of described macroporous resin purification Herba Ephedrae total alkaloids, it is characterised in that step 5)Middle loading liquid pH
It is 5.3-5.7, sample concentration is 0.11-0.13 g mL-1, loading flow velocity is 0.4-0.6 mL min-1, eluant, eluent volume
It is 7.7-7.9 BV, eluant, eluent is 95% ethanol, and elution flow rate is 0.9-1.1mL min-1。
A kind of technique of described macroporous resin purification Herba Ephedrae total alkaloids, it is characterised in that step 5)Middle loading liquid pH
It is 5.5, sample concentration is 0.12 g mL-1, loading flow velocity is 0.5mL min-1, eluant, eluent volume is 7.8 BV, and eluant, eluent is
95% ethanol, elution flow rate is 1.0mL min-1。
The technique of macroporous resin purification Herba Ephedrae total alkaloids of the invention, there is provided a kind of purifying Herba Ephedrae total alkaloids are most
Good technique, easy to operate, yield is high, is that further galenic pharmacy and pharmacodynamic study are offered reference.
Specific embodiment
Instrument and reagent
The Infinity type high performance liquid chromatographs of Agilent 1260(U.S. Agilent Technologies);UV-
2800H type ultraviolet-uisible spectrophotometers(You Nike Shanghai Instrument Ltd.);SHA-A type constant temperature digital display water bath chaders
(The double Shun's experiment Development Co., Ltds in Shanghai);KQ-250E type numerical control supersonic cleaning machines(Kunshan Ultrasonic Instruments Co., Ltd.),
RE-52A type Rotary Evaporators(Shanghai Ya Rong bio-instruments factory);METTLER AL104 type a ten thousandth electronic balances(Mei Te
Le-support benefit instrument company).
Macroreticular resin HPD100(Cangzhou Bon Adsorption Material Science and Technology Co., Ltd of Hebei province);Bromothymol blue(Hong Kong
Fisher Science companies);Acetonitrile is chromatographically pure(TEDIA companies of the U.S.);Ethanol, phosphoric acid, hydrochloric acid, ammoniacal liquor, chloroform etc. are
It is pure to analyze;Ephedrine hydrochloride reference substance No. 171241-201007, pseudoephedrine hydrochloride reference substance No. 171237-
201208th, mephedrine reference substance No.171247-200301(Nat'l Pharmaceutical & Biological Products Control Institute), glass chromatography
Post(Internal diameter 1.5cm, Hangzhou Hui Pu chemical industry Instrument Ltd. is customized).
Medicinal material No. 201304 is purchased from Zhejiang Co., Ltd of Zhen Yuan chain drug stores, by Zhejiang University of Traditional Chinese Medicine's resource and identification
Teaching and research room associate professor Chen Xilin is accredited as ephedra sinicaEphedra sinica StapfHerbaceous stem stem.
Method and result
1)Precision weighs Chinese ephedra fine powder in right amount, 8 times of 0.5% aqueous hydrochloric acid solutions of amount of addition, 60 DEG C, 250W ultrasonic extraction 1h,
Suction filtration, required concentration is concentrated under reduced pressure into Rotary Evaporators;
2)Precision draws appropriate Chinese ephedra need testing solution, sequentially adds 7.5 phosphate buffer 1s of pH 0 mL, 0.05%
The mL of bromothymol blue solution 4, after 3 min of complexing, adds 10 mL chloroforms to be extracted twice every time, divides and takes chloroform layer, determines 416
Absorbance at nm wavelength, is control with ephedrine hydrochloride, calculates the content of TA;
3)Appropriate Chinese ephedra need testing solution is taken, HPLC analyses are carried out, ephedrine, d-pseudo-ephedrine, methylephedrine is determined
Three kinds of contents of main component, chromatographic condition is:Chromatographic column Agilent Zorbax SB-C18(250 mm × 4.6 mm, 5 μ
m), 0.1% phosphoric acid:Acetonitrile=95:5, Detection wavelength is 210 nm;30 DEG C of column temperature;The mL min of flow velocity 1-1, the μ L of sample size 20;
4)HPD100 type macroreticular resins are placed in beaker, 24 h are soaked with 95% ethanol, it is fully expanded, after suction filtration
Add 95% ethanol to wash macroreticular resin to cleaning solution and add appropriate distilled water without white opacity phenomenon, then ethanol is cleaned with distilled water,
It is standby after vacuum filtration;
5)Loading, wash-out, wherein loading liquid pH are 5.5, and sample concentration is 0.12 g mL-1, loading flow velocity is 0.5mL
min-1, eluant, eluent volume is 7.8 BV, and eluant, eluent is 95% ethanol, and elution flow rate is 1.0mL min-1。
Experiment proves that after, the overall target absorption ration of the Herba Ephedrae total alkaloids of gained is 5.58 mg g-1, comprehensively refer to
Mark is 5.50 mg g than desorption quantity-1, close to predicted value(Integrated value is inhaled according to Herba Ephedrae total alkaloids and three kinds of ratios of main component
Attached amount, assign corresponding weight than desorption quantity entropy assessment after be calculated).
Eluent Rotary Evaporators are evaporated to obtain Herba Ephedrae total alkaloids purified, the wherein content of TA and three is determined
The content of main component is planted, the yield for calculating gained Herba Ephedrae total alkaloids and its three kinds of main components respectively reaches 30.01% He
28.63%, it is promoted to 2.18 times before purification and 2.25 times.
Macroreticular resin has the features such as physical and chemical stability is high, selectivity is good, regeneration treatment facilitates, and this experiment is used
The Adsorption and desorption characteristics of Herba Ephedrae total alkaloids are had obvious by HPD100 type non-polar macroporous resins compared to other macroreticular resins
Advantage.Equilibrium adsorption capacity is up to 15.49 mg g-1, Static Adsorption rate reaches 89.95 % and static desorption efficiency reaches 85.48 %.
Generally, nonpolar adsorption resin is adapted to adsorb apolar substance from polar solvent, and vice versa.In Chinese ephedra alkaloid into
Polarity is larger, and HPD100 types macroreticular resin has larger adsorbance to it, may have larger specific area 650-700 with it
(m2•g-1), appropriate average pore size 90-100()There is substantial connection.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all it is of the invention spirit and
Any modification, equivalent and improvement for being made within principle etc., are all contained within protection scope of the present invention.
Claims (3)
1. a kind of technique of macroporous resin purification Herba Ephedrae total alkaloids, it is characterised in that comprise the following steps:
1)Precision weighs Chinese ephedra fine powder in right amount, adds 8 times of 0.5% aqueous hydrochloric acid solutions of amount, and 60 DEG C, 250W ultrasonic extraction 1h take out
Filter, required concentration is concentrated under reduced pressure into Rotary Evaporators;
2)Precision draws appropriate step 1)Obtained solution, sequentially adds the mL of 7.5 phosphate buffer 1s of pH 0,0.05% bromine
The mL of bromothymol blue solution 4, after 3 min of complexing, adds 10 mL chloroforms to be extracted twice every time, divides and takes chloroform layer, determines 416
Absorbance at nm wavelength, is control with ephedrine hydrochloride, calculates the content of TA;
3)Take appropriate step 1)Obtained solution, carries out HPLC analyses, determines ephedrine, d-pseudo-ephedrine, methylephedrine three
Plant the content of main component;Chromatographic condition is:Chromatographic column Agilent Zorbax SB-C18, 250 mm × 4.6 mm, 5 μm,
0.1% phosphoric acid:Acetonitrile=95:5, Detection wavelength is 210 nm;30 DEG C of column temperature;The mL min of flow velocity 1-1, the μ L of sample size 20;
4)Macroreticular resin is placed in beaker, 24 h are soaked with 95 % ethanol, it is fully expanded, 95 % ethanol are added after suction filtration
Washing macroreticular resin to cleaning solution adds appropriate distilled water without white opacity phenomenon, then cleans ethanol with distilled water, after vacuum filtration
Standby, described macroreticular resin is HPD100 type macroreticular resins;
5)Loading, wash-out, wherein loading liquid pH are 5-6, and sample concentration is 0.1-0.15 g mL-1, loading flow velocity is
0.3—0.7 mL•min-1, eluant, eluent volume is 7.5-8 BV, and eluant, eluent is 95% ethanol, and elution flow rate is 0.8-1.2
mL•min-1。
2. a kind of technique of macroporous resin purification Herba Ephedrae total alkaloids as claimed in claim 1, it is characterised in that step 5)In
Loading liquid pH is 5.3-5.7, and sample concentration is 0.11-0.13 g mL-1, loading flow velocity is 0.4-0.6 mL min-1,
Eluant, eluent volume is 7.7-7.9 BV, and eluant, eluent is 95% ethanol, and elution flow rate is 0.9-1 .1mL min-1。
3. a kind of technique of macroporous resin purification Herba Ephedrae total alkaloids as claimed in claim 1, it is characterised in that step 5)In
Loading liquid pH is 5.5, and sample concentration is 0.12 g mL-1, loading flow velocity is 0.5mL min-1, eluant, eluent volume is 7.8
BV, eluant, eluent is 95% ethanol, and elution flow rate is 1.0mL min-1。
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Citations (3)
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CN1201029A (en) * | 1997-05-29 | 1998-12-09 | 中国科学院西北高原生物研究所 | Method for preparing Ephedra sinica fine powder by Amberlyst process, and technology for producing its by-product tanning material |
CN1443749A (en) * | 2002-03-12 | 2003-09-24 | 中国科学院过程工程研究所 | Method for separating and purifying ephedrine by using weak acid cation exchange resin and macroporous resin |
CN1600777A (en) * | 2003-09-25 | 2005-03-30 | 中国科学院过程工程研究所 | New method for picking-up alkakoid of Chinese ephedra in large scale |
-
2014
- 2014-02-11 CN CN201410047475.6A patent/CN103800397B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1201029A (en) * | 1997-05-29 | 1998-12-09 | 中国科学院西北高原生物研究所 | Method for preparing Ephedra sinica fine powder by Amberlyst process, and technology for producing its by-product tanning material |
CN1443749A (en) * | 2002-03-12 | 2003-09-24 | 中国科学院过程工程研究所 | Method for separating and purifying ephedrine by using weak acid cation exchange resin and macroporous resin |
CN1600777A (en) * | 2003-09-25 | 2005-03-30 | 中国科学院过程工程研究所 | New method for picking-up alkakoid of Chinese ephedra in large scale |
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Title |
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HPLC法同时测定小儿平喘祛痰颗粒中盐酸麻黄碱、盐酸伪麻黄碱、苦杏仁苷含量;杨德斌等;《中国中药杂志》;20130331;第38卷(第5期);687-690 * |
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