CN101928285A - Method for extracting major alkaloids from rhizoma coptidis - Google Patents
Method for extracting major alkaloids from rhizoma coptidis Download PDFInfo
- Publication number
- CN101928285A CN101928285A CN2010102466116A CN201010246611A CN101928285A CN 101928285 A CN101928285 A CN 101928285A CN 2010102466116 A CN2010102466116 A CN 2010102466116A CN 201010246611 A CN201010246611 A CN 201010246611A CN 101928285 A CN101928285 A CN 101928285A
- Authority
- CN
- China
- Prior art keywords
- acetonitrile
- alkaloid
- obtains
- ethanol
- component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a method for extracting major alkaloids from rhizoma coptidis. The extraction comprises the following steps of: extracting rhizoma coptidis percolation liquid; crudely extracting alkaloids under an acid condition; removing impurities from the crudely extracted alkaloid mother liquid by using macroporous resin to obtain an alkaloid mixture; crudely separating the alkaloid mixture on a chromatographic column; and crystallizing, separating and refining. Compared with the chromatographic separation method of the traditional preparation, the separation method which adopts a reverse chromatographic column to separate a plurality of major alkaloids from the rhizoma coptidis under normal pressure has the advantages that: the yield is greatly improved; cost is lower; and the purified product can be used as a reference substance for quality standard research and development.
Description
Technical field
The present invention relates to a kind of extracting method of chemical monomer composition, relate to the extracting method of main alkaloid in a kind of coptis in particular.
Technical background
The chemical ingredients of coptis Coptis chinensis Franch. is mainly former barberry property alkaloid, since the sixties, China is studied the chemical ingredients of the coptis with regard to the scholar is arranged, successively from the coptis rhizome isolation identification isoquinoline alkaloids such as Berberine, palmatine, jateorhizine, palmatine, coptisine, epiberberine.At present both at home and abroad commercially available reference substance has only Berberine, palmatine, jateorhizine, and epiberberine, coptisine, palmatine be because of separation difficulty, and Nat'l Pharmaceutical ﹠ Biological Products Control Institute does not also have standard substance to sell, and elsewhere also is difficult to buy.
Berberine is a topmost alkaloid in the coptis, and content is up to 5.2%～7.69%.A lot of to the Berberine Study on extraction process in recent years, less relatively at the technical study of other biological alkali.The alkaloid extraction method based on Berberine of bibliographical information has decocting method, pickling process, refluxing extraction, supersound extraction, solid-liquid hot extraction, enzymolysis process, microwave method, micromethod, half bionical, supercritical extraction extraction etc.; Extraction solvent has water, sour water, ethanol, acidic ethanol, milk of lime etc.Alkaloidal separation purifying technique has macroporous resin purification, countercurrent chromatography, liquid-film method etc.Also have some scholars that several different extracting method are compared, for example high red prosperous grade compares the extraction process of berberine in the golden cypress, finds that the acid alcohol extraction is better than alkaline extraction and extraction using alcohol.Shi Ji connect to wait utilization pharmacopeia method, circumfluence method, ultrasonic method, backflow ultrasonic method to extract the Berberine in the coptis, the result show reflux ultrasonic short than the additive method time, content is high, the suitable Berberine that extracts in the coptis.The scholar investigates the influence of coptis extraction granularity, extraction temperature and the emulsifying agent of coptis medicinal material in addition, and according to experimental result, content is the highest in 20 orders～40 order extracts, and the above residence of 10 orders is inferior, and 40 orders～80 orders and the following content of 80 orders sharply descend; Along with temperature raises, Berberine must be measured and increase, but when temperature reached 100 ℃, Berberine was destroyed bigger; Acid iodide type anion surfactant and polyamine class tensio-active agent reduce the berberine extracted amount. and the nonionic surface active agent propylene glycol ester has synergy to improving extraction yield when the span-80 lower concentration.
Also do not have obtain the coptis several main alkaloid a kind of from the coptis, the separation simultaneously at present, and the method for suitable industrialized production.
Summary of the invention
For addressing the above problem, the invention provides the extracting method of main alkaloid in a kind of company, extraction step comprises and extracts that coptis percolate, acidic conditions are carried alkaloid at the beginning of down, just proposing on the alkaloid mother liquor macroporous resin removal of impurities, to obtain on alkaloid mixture, the alkaloid mixture chromatographic column roughing out and Crystallization Separation refining that the described step that goes up the chromatographic column roughing out is:
1) will go up the alkaloid mixed solution that the macroporous resin removal of impurities obtains and be recycled to the dried alkaloid mixture that obtains;
2) with the alkaloid mixture with 65～85 hot water dissolving, last C
18The reverse phase silica gel post, under the condition of normal pressure, column temperature remains under 35～55 ℃ of conditions, and water, 2% acetonitrile, 4% acetonitrile, 6% acetonitrile, 8% acetonitrile, 10% acetonitrile, 12% acetonitrile, 15% acetonitrile gradient wash-out receive elutriant respectively according to colour band successively;
3) with the above-mentioned elutriant of pressing the same colour band that colour band receives, be recycled to dried, with 65～85 ℃ hot water dissolving, last C
18The reverse phase silica gel post is used water, 1% acetonitrile, 2% acetonitrile, 3% acetonitrile, 4% acetonitrile, 5% acetonitrile, 6% acetonitrile, 7% acetonitrile wash-out successively respectively, reclaims elutriant respectively according to colour band;
4) will reclaim elutriant repeating step 3 respectively according to colour band) operation, till each colour band detects to same single-point by thin layer, obtain component I, component I I, component III and component I V from big to small according to polarity.
The step of described extraction coptis percolate is: Golden Thread is soaked into last diafiltration post with 90% ethanol; Use 95% ethanol, 60% ethanol, 30% ethanol, water, 0.5% sulfuric acid gradient, 0.5% sulfuric acid gradient diacolation successively, merge percolate, filter and obtain coptis percolate.
Described acidic conditions is carried alkaloid at the beginning of down: will extract coptis percolate and be recycled to and do not contain ethanol, and add acid and transfer pH 2～3, leave standstill 12～24 hours, filtering-depositing obtains yellow mercury oxide, and mother liquor adds decolorizing with activated carbon, obtains just carrying the alkaloid mother liquor.
Describedly just carry that the macroporous resin removal of impurities is on the alkaloid mother liquor: concentrate and just carry the alkaloid mother liquor, last D101 type macroporous resin column, water is eluted to colourless, uses 20% ethanol, 40% ethanol elution successively; Merge ethanol eluate, concentrate and obtain the alkaloid mixture.
Described Crystallization Separation is refining to be: component I obtains Jatrorrhizine chloride with 50% acetonitrile crystallization, and mother liquor obtains the hydrochloric acid palmatine with 95% alcohol crystal again;
Component I I makes with extra care with 95% alcohol crystal and obtains the hydrochloric acid epiberberine;
Component III obtains the hydrochloric acid coptisine with 50% acetonitrile crystal refining;
Component I V obtains berberine hydrochloride with 50% acetonitrile crystallization, and mother liquor obtains palmatine hydrochloride with 95% alcohol crystal again.
Useful technique effect of the present invention is: the present invention adopts the reverse chromatograms post under condition of normal pressure, isolating method is separated several main alkaloids in the coptis, preparative chromatography separation method more in the past, output increases substantially, cost is lower, and the product of purification can be used as the reference substance of quality standard research.
Embodiment
The preparation of embodiment 1 coptis percolate
Take by weighing coptis 5kg meal and cross 10 mesh sieves, the part that can not sieve repeats crushing screening.Meal is soaked into 30min with 95% ethanol, in the diacolation post of dress 5cm diameter, added 95% alcohol immersion medicinal material 12 hours, beginning diacolation, 3 times of volumes of diacolation; Change 60% ethanol and continue diacolation, the amount of 2 times of volumes of diacolation is changed 30% ethanol and is continued diacolation, the amount of 2 times of volumes of diacolation; Merge all ethanol percolation liquid, reclaim ethanol, obtain ethanol percolation liquid;
In percolator, add 0.5% sulfuric acid, soaked 6 hours, continue 3 times of volumes of diacolation, incorporate ethanol percolation liquid into, obtain coptis percolate.
Carry alkaloid at the beginning of under embodiment 2 acidic conditionss
The coptis percolate that obtains among the reclaim under reduced pressure embodiment 1, filters after the dissolving with 65 ℃ of hot water dissolvings immediately to doing, and adds hydrochloric acid and transfers pH2～3, leaves standstill under the room temperature 12 hours, and solution is separated out yellow mercury oxide; Filter above-mentioned yellow mercury oxide, merge mother liquor, add activated carbon in mother liquor, leave standstill, filtration of active charcoal obtains the mother liquor that decolours;
Above-mentioned precipitation with 80 ℃ of dissolvings of dissolve with ethanol of 95%, is added decolorizing with activated carbon, and filtration of active charcoal leaves standstill cooling 3 hours, separates out precipitation, and mother liquor further concentrates and separates out crystallization I, and filtering-depositing is with the crystal II that arrives of 50% acetonitrile recrystallization.
Determine that by thin layer detection and HPLC detection crystallization I and crystal II are that a kind of interior mark purity is 99% chemical monomer composition.
Described thin layer detection method is: the crystallization that takes a morsel, use dissolve with methanol, as test liquid; The reference substance that takes a morsel adds dissolve with methanol, in contrast liquid; Test liquid and contrast liquid are put on same block of thin layer plate, are developping agent with hexanaphthene-vinyl acetic monomer-Virahol-methanol-water-triethylamine (3: 3.5: 1: 1.5: 0.5: 1) (groove being added equivalent ammoniacal liquor, presaturation 20min), launch, take out, dry, put under the ultraviolet lamp 365nm and inspect.
Described HPLC detection method is: the same preparation test liquid and contrast liquid, and with chromatographic condition: weighting agent is an octadecylsilane chemically bonded silica; Moving phase is acetonitrile-50mmol/L potassium dihydrogen phosphate (50: 50) (add the 15mmol/L sodium lauryl sulphate in the mixed solution, regulating pH with phosphoric acid again is 4.0); Flow velocity 0.6mL/min; Detect wavelength 345nm; 30 ℃ of column temperatures are analyzed.
Chromatographic column roughing out and further Crystallization Separation and purifying on the embodiment 3 alkaloid mixtures
The alkaloid mixed solution that last macroporous resin removal of impurities is obtained is recycled to the dried alkaloid mixture that obtains;
With the hot water dissolving of alkaloid mixture with 65～85 ℃, last C
18The reverse phase silica gel post, under the condition of normal pressure, column temperature remains under 35～55 ℃ of conditions, and water, 2% acetonitrile, 4% acetonitrile, 6% acetonitrile, 8% acetonitrile, 10% acetonitrile, 12% acetonitrile, 15% acetonitrile gradient wash-out receive elutriant respectively according to colour band successively;
With the above-mentioned elutriant of pressing the same colour band that colour band receives, be recycled to dried, with 65～85 ℃ hot water dissolving, last C
18The reverse phase silica gel post is used water, 1% acetonitrile, 2% acetonitrile, 3% acetonitrile, 4% acetonitrile, 5% acetonitrile, 6% acetonitrile, 7% acetonitrile wash-out successively respectively, reclaims elutriant respectively according to colour band;
To reclaim elutriant respectively according to colour band and repeat the above-mentioned steps operation, till each colour band detects to same single-point by embodiment 2 described thin layer detection methods, obtain component I, component I I, component III and component I V according to polarity order from big to small.
The each component that obtains is carried out the fractional crystallization purifying respectively:
Component I obtains crystal II with 50% acetonitrile crystallization, and mother liquor obtains crystallization IV with 95% alcohol crystal again;
Component I I makes with extra care with 95% alcohol crystal and obtains crystallization V;
Component III obtains crystal II with 50% acetonitrile crystal refining;
Component I V obtains crystallization I with 50% acetonitrile crystallization, and mother liquor obtains crystallization VI with 95% alcohol crystal again;
To the detection of above-mentioned crystallization by embodiment 2 described HPLC methods, marker method purity melts distance, MS, UV, IR and H-NMR then respectively and detects the structure of judging composition greater than 99%.
Embodiment 4 isolated alkaloid chemical monomer compositions
By being the described method of embodiment 1-3, obtain several main alkaloid of the coptis, be respectively:
Crystallization I berberine hydrochloride: faint yellow needle crystal, be soluble in hot water, be slightly soluble in cold water, cold ethanol, be dissolved in chloroform and ether hardly; Molten distance: 204.8～205.4 ℃;
350,265,229; IR (KBr) cm
-1: 3402,2997,1504,1363;
1H-NMR (CD
3OD) δ: 3.30 (2H, t, J=6.3Hz, H-2), 4.08 (3H, s, H-20, OCH
3), 4.19 (3H, s, H-19, CH
3), 4.85 (2H, t, J=15.4Hz, H-1), 6.08 (2H, s, H-15), 6.93-9.75 (6H, Ar-H); FAB-MS (m/z): 336[M]
+
Crystal II hydrochloric acid coptisine: orange-yellow needle crystal, the utmost point is insoluble in water, is slightly soluble in ethanol, methyl alcohol; 290 ℃ of complete charings, 400 ℃ are not molten yet;
360,265,241; IR (KBr) cm
-1: 3365,3004,1604,1323;
1H-NMR (CD
3OD) δ ppm:3.25 (2H, brs, C
6H
2), 4.89 (2H, brs, C
5H
2), 6.10 (2H, s, C
2,3-OCH
2O-), 6.46 (2H, s, C
9,10-OCH
2O-), 6.95 (1H, s, C
4H), 7.64 (1H, s, C
1H), 7.87 (2H, s, C
11,12H), 8.73 (1H, s, C
13H), 9.72 (1H, s, C
8H); FAB-MS (m/z): 320[M]
+
Crystal II I Jatrorrhizine chloride: orange needle crystal, water-soluble, ethanol, methyl alcohol are insoluble to chloroform.Molten distance: 212.2～212.9 ℃;
350,265,239; IR (KBr) cm
-1: 3734,3341,1634,1533,1444,1361;
1H-NMR (CD
3OD) δ: 3.20 (2H, t, J=6.3Hz, H-2), 4.88 (2H, m, H-1), 6.84 (1H, s, H-3), 7.63 (1H, s, H-6), 7.98 (1H, d, J=9.15Hz, H-8), 8.07 (1H, d, J=9.2Hz, H-9), 8.76 (1H, s, H-7), 9.72 (1H, s, H-12); FAB-MS (m/z): 338[M]
+
Crystallization IV hydrochloric acid palmatine: orange-yellow crystalline powder, water-soluble, ethanol, methyl alcohol are insoluble to chloroform.Molten distance: 243.1～244.0 ℃;
227,266,349,430; IR (KBr) cm
-1: 3390,1635,1605,1564,1508;
1H-NMR (CD
3OD) δ: 9.74 (1H, s, H-8), 8.63 (1H, s, H-13), 8.08 (1H, d, J=9.0Hz, H-11), 8.00 (1H, d, J=9.2Hz, H-12), 7.55 (1H, s, H-1), 7.01 (1H, s, H-4), 4.92 (2H, t, J=6.0Hz, H-6), 4.20 (3H, s, 9-OCH
3), 4.10 (3H, s, 10-OCH
3), 3.96 (3H, s, 2-OCH
3), 3.30 (2H, t, J=6.0Hz, H-5); FAB-MS (m/z): 338[M]
+
Crystallization V hydrochloric acid epiberberine: orange red needle crystal,, water-soluble, ethanol, methyl alcohol are insoluble to chloroform.Molten distance: 266.0～267.5 ℃;
359,265,243; IR (KBr) cm
-1: 3327,2929,1604,1359;
1H-NMR (CD
3OD) δ: 3.30 (2H, t, J=6.3Hz, H-2), 3.94 (2H, t, J=15.4Hz, H-1), 4.88 (2H, s, H-15), 6.46-9.71 (6H, Ar-H); FAB-MS (m/z): 336[M]
+Structural representation is seen accompanying drawing 25～28;
Crystallization VI palmatine hydrochloride: yellow needle (95% ethyl alcohol recrystallization).Be dissolved in cold water, easy molten hot water is slightly soluble in ethanol, is dissolved in chloroform and ether hardly.Molten distance: 208.0～208.8 ℃;
348,266,227; IR (KBr) cm
-1: 3647,3354 (OH), 1605,1510,1458,1364;
1H-NMR (CD
3OD) δ: 3.27 (2H, m, H-2), 4.93 (2H, t, J=6.3Hz, H-1), 7.03 (1H, s, H-3), 7.62 (1H, s, H-6), 8.01 (1H, d, J=9.2Hz, H-8), 8.09 (1H, s, J=9.2Hz, H-9), 8.79 (1H, s, H-7), 9.75 (1H, s, H-12); FAB-MS (m/z): 352[M]
+
Claims (5)
1. the extracting method of main alkaloid in the coptis, extraction step comprises and extracts that coptis percolate, acidic conditions are carried alkaloid at the beginning of down, just proposing on the alkaloid mother liquor macroporous resin removal of impurities, to obtain on alkaloid mixture, the alkaloid mixture chromatographic column roughing out and Crystallization Separation refining that it is characterized in that: the described step that goes up the chromatographic column roughing out is:
1) will go up the alkaloid mixed solution that the macroporous resin removal of impurities obtains and be recycled to the dried alkaloid mixture that obtains;
2) with the hot water dissolving of alkaloid mixture with 65～85 ℃, last C
18The reverse phase silica gel post, under the condition of normal pressure, column temperature remains under 35～55 ℃ of conditions, and water, 2% acetonitrile, 4% acetonitrile, 6% acetonitrile, 8% acetonitrile, 10% acetonitrile, 12% acetonitrile, 15% acetonitrile gradient wash-out receive elutriant respectively according to colour band successively;
3) with the above-mentioned elutriant of pressing the same colour band that colour band receives, be recycled to dried, with 65～85 ℃ hot water dissolving, last C
18The reverse phase silica gel post is used water, 1% acetonitrile, 2% acetonitrile, 3% acetonitrile, 4% acetonitrile, 5% acetonitrile, 6% acetonitrile, 7% acetonitrile wash-out successively respectively, reclaims elutriant respectively according to colour band;
4) will reclaim elutriant repeating step 3 respectively according to colour band) operation, till each colour band detects to same single-point by thin layer, obtain component I, component I I, component III and component I V from big to small according to polarity.
2. method according to claim 1 is characterized in that: the step of described extraction coptis percolate is: Golden Thread is soaked into last diafiltration post with 90% ethanol; Use 95% ethanol, 60% ethanol, 30% ethanol, water, 0.5% sulfuric acid gradient diacolation successively, merge percolate, reclaim ethanol, filter and obtain coptis percolate.
3. method according to claim 1, it is characterized in that: carrying alkaloid at the beginning of under the described acidic conditions is: reclaim coptis percolate to doing, add 65～85 ℃ of hot water to dissolving, filter, add acid and transfer pH 2～3, left standstill filtering-depositing 12～24 hours, mother liquor adds decolorizing with activated carbon, obtains just carrying the alkaloid mother liquor.
4. method according to claim 1 is characterized in that: describedly just carry that the macroporous resin removal of impurities is on the alkaloid mother liquor: concentrate and just carry the alkaloid mother liquor, and last D101 type macroporous resin column, water is eluted to colourless, uses 20% ethanol, 40% ethanol elution successively; Merge ethanol eluate, concentrate and obtain the alkaloid mixture.
5. method according to claim 1 is characterized in that: described Crystallization Separation is refining to be: component I obtains Jatrorrhizine chloride with 50% acetonitrile crystallization, and mother liquor obtains the hydrochloric acid palmatine with 95% alcohol crystal again;
Component I I makes with extra care with 95% alcohol crystal and obtains the hydrochloric acid epiberberine;
Component III obtains the hydrochloric acid coptisine with 50% acetonitrile crystal refining;
Component I V obtains berberine hydrochloride with 50% acetonitrile crystallization, and mother liquor obtains palmatine hydrochloride with 95% alcohol crystal again.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102466116A CN101928285A (en) | 2010-08-05 | 2010-08-05 | Method for extracting major alkaloids from rhizoma coptidis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102466116A CN101928285A (en) | 2010-08-05 | 2010-08-05 | Method for extracting major alkaloids from rhizoma coptidis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101928285A true CN101928285A (en) | 2010-12-29 |
Family
ID=43367761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010102466116A Pending CN101928285A (en) | 2010-08-05 | 2010-08-05 | Method for extracting major alkaloids from rhizoma coptidis |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101928285A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786518A (en) * | 2011-05-18 | 2012-11-21 | 中国医学科学院药物研究所 | Palmatine hydrochloride crystal B substance, its preparation method, and its applications in medicines and healthcare products |
| CN103421001A (en) * | 2012-05-22 | 2013-12-04 | 中国医学科学院药物研究所 | Berberine hydrochloride crystal E form substance, preparation method, pharmaceutical compositions and applications |
| CN103421000A (en) * | 2012-05-22 | 2013-12-04 | 中国医学科学院药物研究所 | Berberine hydrochloride crystal F form substance, preparation method, pharmaceutical compositions and applications |
| CN103421002A (en) * | 2012-05-22 | 2013-12-04 | 中国医学科学院药物研究所 | Berberine hydrochloride crystal D form substance, preparation method, pharmaceutical compositions and applications |
| CN104016978A (en) * | 2014-06-06 | 2014-09-03 | 北京健坤和医药科技有限公司 | Palmatine hydrochloride crystal form C as well as preparation method thereof and application thereof in medicament composition or health-care product |
| CN105044300A (en) * | 2015-06-18 | 2015-11-11 | 中国人民解放军第三〇二医院 | Method for adjusting dosage of medicinal material coptidis rhizoma on basis of anti-dysentery bacillus effect equivalency factor |
| CN105203680A (en) * | 2015-09-06 | 2015-12-30 | 齐鲁工业大学 | Microextraction coupling technique and application thereof to quality control over Qihuang capsule |
| CN108142655A (en) * | 2018-01-18 | 2018-06-12 | 兰溪富晟食品科技有限公司 | Improve feed of laying rate of laying hen and preparation method thereof |
| CN109187841A (en) * | 2018-08-31 | 2019-01-11 | 成都大学 | The thin-layer identification method of American lotus |
| CN110105353A (en) * | 2019-06-18 | 2019-08-09 | 云南润嘉药业有限公司 | Fibrauretine crystalline form and the preparation method and application thereof |
-
2010
- 2010-08-05 CN CN2010102466116A patent/CN101928285A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786518A (en) * | 2011-05-18 | 2012-11-21 | 中国医学科学院药物研究所 | Palmatine hydrochloride crystal B substance, its preparation method, and its applications in medicines and healthcare products |
| CN102786518B (en) * | 2011-05-18 | 2016-09-14 | 中国医学科学院药物研究所 | Palmatine hydrochloride crystal B-type material and preparation method are applied with in medicine and health product |
| CN103421001A (en) * | 2012-05-22 | 2013-12-04 | 中国医学科学院药物研究所 | Berberine hydrochloride crystal E form substance, preparation method, pharmaceutical compositions and applications |
| CN103421000A (en) * | 2012-05-22 | 2013-12-04 | 中国医学科学院药物研究所 | Berberine hydrochloride crystal F form substance, preparation method, pharmaceutical compositions and applications |
| CN103421002A (en) * | 2012-05-22 | 2013-12-04 | 中国医学科学院药物研究所 | Berberine hydrochloride crystal D form substance, preparation method, pharmaceutical compositions and applications |
| CN104016978A (en) * | 2014-06-06 | 2014-09-03 | 北京健坤和医药科技有限公司 | Palmatine hydrochloride crystal form C as well as preparation method thereof and application thereof in medicament composition or health-care product |
| CN105044300A (en) * | 2015-06-18 | 2015-11-11 | 中国人民解放军第三〇二医院 | Method for adjusting dosage of medicinal material coptidis rhizoma on basis of anti-dysentery bacillus effect equivalency factor |
| CN105203680A (en) * | 2015-09-06 | 2015-12-30 | 齐鲁工业大学 | Microextraction coupling technique and application thereof to quality control over Qihuang capsule |
| CN108142655A (en) * | 2018-01-18 | 2018-06-12 | 兰溪富晟食品科技有限公司 | Improve feed of laying rate of laying hen and preparation method thereof |
| CN109187841A (en) * | 2018-08-31 | 2019-01-11 | 成都大学 | The thin-layer identification method of American lotus |
| CN110105353A (en) * | 2019-06-18 | 2019-08-09 | 云南润嘉药业有限公司 | Fibrauretine crystalline form and the preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101928285A (en) | Method for extracting major alkaloids from rhizoma coptidis | |
| CN101433565B (en) | Total alkaloid extract of seeds of harmel genus, and preparation thereof | |
| CN102285982B (en) | Method for separating and purifying monomer compounds from Chinese medicinal herb rhizoma coptidis | |
| CN102399187B (en) | Preparation method of sinomenine | |
| CN101134743B (en) | Method for extracting and separating Huperzine from huperzine serrate | |
| CN102101840B (en) | Method for extracting and separating high-purity 1-Deoxynojirimycin from folium mori | |
| CN107353201A (en) | A kind of natural shikimic acid extract of high content and preparation method thereof | |
| CN106831804B (en) | The method that ion exchange and silica gel column chromatography separation prepare Stephania tetrandra first, B prime | |
| CN105753917A (en) | Separating purifying method of liquiritin | |
| CN101260138B (en) | Highly effective separation purification method for polygalic acid and tenuigenin | |
| WO2012061984A1 (en) | Method for preparing albiflorin and paeoniflorin | |
| CN107445952B (en) | Method for extracting gladiolide and coptisine and application | |
| CN101172975B (en) | Method of preparing five-alkaloid composition of corydalis saxicola bunting | |
| CN111171104B (en) | Method for preparing ursolic acid from rosemary oil paste by-product | |
| CN104418852B (en) | A kind of high-purity coptisine extracting method and application | |
| CN101830892A (en) | Method for separating glycoside chemical components from tibetan capillaris | |
| CN101429197B (en) | Extraction method for joint production of coptis chinensis with coptis chinensis fibrous root as raw material | |
| CN107586311B (en) | The method that robinin -6-C- β-D-Glucose glycosides is extracted in creeping oxalis | |
| CN109912582A (en) | The method of mangiferin is extracted from mango leaf | |
| CN102908371A (en) | Method for preparing high-purity ferulic acid from angelica sinensis | |
| CN101177426A (en) | Process for separating extracting spherosinin from gansu whin | |
| CN113354697B (en) | Method for separating and purifying pectolinarin and linarin | |
| CN102276515A (en) | Method for extracting deoxynojirimycin | |
| CN101891729B (en) | Method for extracting high-purity rhamnazin from ford nervilia leaf | |
| CN101781307B (en) | Method for separating and purifying coptisine monomers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20101229 |