CN105131063A - Method for separating and purifying kinds of flavonoid constituents from meconopsis integrifolia flowers at same time - Google Patents
Method for separating and purifying kinds of flavonoid constituents from meconopsis integrifolia flowers at same time Download PDFInfo
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Abstract
The invention provides a method for separating and purifying kinds of flavonoid constituents from meconopsis integrifolia flowers at the same time and a method for separating and purifying two kinds of known flavonoid constituents at the same time. Through an HSCCC method, four kinds of flavonoid constituents are successfully separated and purified from the meconopsis integrifolia flowers; the separation speed is high, and the method lays a foundation for material basis research of the meconopsis integrifolia flowers. The research finds that the separated known compounds or new compounds have good free radical scavenging activity and can be used as antioxidant medicine or a health-care product.
Description
Technical field
The present invention relates to the method for separation and purification multiple flavones ingredient while of spending middle from Meconopsis integrifolia.
Background technology
Meconopsis integrifolia Meconopsisintegrifolia (Maxim.) Franch. is papaveracease (Papaveraceae) meconopsis (Meconopsis) plant, for traditional Tibetan medicine material, be mainly distributed in the provinces and regions such as Tibet, Sichuan, Yunnan, Qinghai, Gansu in China." Jingzhubencao " is recorded Meconopsis integrifolia and is used as medicine with flower, is used for the treatment of hepatitis, pneumonia and oedema
[1-2].Modern chemical composition research has carried out comparatively systematic research to the chemical composition of the over-ground part of Meconopsis integrifolia, adopts traditional separation method to be separated and obtains the compound such as alkaloid and flavones
[3-5].And Tibetan medicine and pharmacology books record Meconopsis integrifolia is used as medicine with flower, finds no the chemical composition of bibliographical information to Meconopsis integrifolia flower and study.Further, the traditional separation method such as chemical composition many employings silica gel column chromatography, medium pressure column chromatography, preparation liquid phase, SephadexLH-20 of meconopsis plant is separated
[3-7], therefore, the method that pure compound is prepared in simple, quick, reproducible separation will receive increasing concern in this platymiscium.
The difference of the partition ratio of high speed adverse current chromatogram (High-speedcounter-currentchromatography, HSCCC) technical basis compound in immiscible two-phase solvent and realize being separated.Do not need solid carrier, the irreversible adsorption Sum decomposition of sample in sepn process can be avoided, the polarity of solvent systems can be selected according to the character of compound, range of choice is wide, be applicable to the compound of various polarity, and analysis time is shorter, the rate of recovery and product purity high, suitable amplification, is convenient to suitability for industrialized production, can be effective to separation and prepares natural product
[8-10].
Zhou etc.
[11]report, Meconopsis integrifolia over-ground part 70% ethanol extraction has good Hepatocyte protection.Yet there are no and spend the separation and purification of middle flavones ingredient to study by HSCCC method to Meconopsis integrifolia.
Summary of the invention
The object of the present invention is to provide the method for the different flavones ingredient of separation and purification simultaneously from Meconopsis integrifolia.
The invention provides the method for separation and purification 4 kinds of flavones ingredients while of spending middle from Meconopsis integrifolia, it comprises following operation steps:
(1) flower of papaveracease meconopsis plant Meconopsis integrifolia M.integrifolia (Maxim.) Franch. is got, pulverize, with 60 ~ 70%v/v ethanol for solvent extracts, collect alcohol extract, decompression recycling ethanol, successively with water-ethyl acetate solvent system and water-n-butanol solvent system extraction, combined ethyl acetate and butanol extraction liquid, after desolventizing, be residue obtainedly crude extract;
(2) ethyl acetate is got: propyl carbinol: water=2:3:5v/v/v, shake well, stratification, above is stationary phase mutually, and lower is moving phase mutually, stationary phase is full of separation spiral tube, column temperature 30 ~ 35 DEG C, main frame rotates forward, and rotating speed is 890 ~ 920r/min, then enter moving phase with the flow pump of 2mL/min, in tubing string, reach equilibrium state to two-phase solvent; By crude extract prepared by step (1), below be dissolution with solvents mutually, prepare sample solution, by sample solution sample introduction, monitor under 254nm, collect the target component that appearance time is 250 ~ 280min, 300 ~ 320min, 360 ~ 90min, 420 ~ 450min successively, namely obtain compound 1 ~ 4 successively, each structural formula of compound is as follows:
The selection of solvent system is that high speed adverse current chromatogram is separated vital link in (HSCCC), according to the physico-chemical property of material to be separated, need select suitable solvent system.Partition ratio is the important parameter that HSCCC is separated, and be one of reference frame of screening solvent system, desirable partition ratio is that 0.5 ~ 2, K value makes band broadening too greatly, and K value is too little, and peak cannot be separated
[12-13].The present invention adopts UPLC method to measure the K value of solvent system, the results are shown in Table 1.
The K value of table 1 compound 1 ~ 4 in different solvents system
As can be seen from Table 1, in chloroform/methanol/aqueous systems (4:3:2), the K value of target compound is too large, is not suitable for being separated, therefore attempts selecting ethyl acetate/n-butanol/water system.Result shows, in different volumes solvent burden ratio, ethyl acetate/propyl carbinol/methanol/water system (4:1:0.5:5, v/v/v/v) is although K value (1.K=0.58; 2.K=0.82; 3.K=1.38; 4.K=1.26) suitable, but the separating effect of target peak bad in substantial sepn, peak does not separate, and four peaks are gone out together.Therefore consider that the mode by increasing K value makes appearance time delay, whether test can make peak reach the object of separation.Reduce the volume of ethyl acetate, increase the volume of propyl carbinol, when employing solvent system is ethyl acetate/n-butanol/water system (3:2:5, v/v/v), time, K value is comparatively large, and the K value at peak 3 and 4 is greater than 2, separating effect makes moderate progress, but peak still can not reach separation.Continue to reduce ethyl acetate, increase the amount of propyl carbinol, adopt ethyl acetate/n-butanol/water system (2:3:5, v/v/v), although K value very large (1.K=1.85; 2.K=2.46; 3.K=4.45; 4.K=4.56), much larger than 2, but still good separating effect can be obtained.Can think thus, when being separated the present invention's each compound selective solvent system, except reference K value, actual separation test is also necessary, adopts the solvent system that K value is larger, delays appearance time, be conducive to the separation at peak.
Other conditions that HSCCC is separated also have larger impact as rotating speed, column temperature, flow velocity to separation, need carry out the suitable condition of test and Selection.Ethyl acetate/n-butanol/water system belongs to the higher solvent systems of interfacial tension, and higher rotating speed can promote the transmission resistance distributing and reduce particle
[14], therefore select rotating speed to be 900r/min.Instrument column temperature remains with very important effect to stationary phase, has considerable influence, raise column temperature and contribute to the stationary phase retention rate improving this system the stationary phase retention rate of the strong n-butanol solvent system of wetting ability
[15], test finds, when column temperature 35 DEG C, the retention rate of ethyl acetate/n-butanol/water (2:3:5, v/v/v) system is 46%, reaches separation requirement.Because selected solvent system retention rate is lower, high flow rate is unfavorable for that stationary phase retains, therefore selects flow velocity to be 2.0mL/min.
Further, in step (1), alcohol concn is 70%v/v.
Present invention also offers and spend the middle method being simultaneously separated 2 kinds of flavones ingredients from Meconopsis integrifolia, it comprises following operation steps:
(1) flower of papaveracease meconopsis plant Meconopsis integrifolia M.integrifolia (Maxim.) Franch. is got, pulverize, with 60 ~ 70%v/v ethanol for solvent extracts, collect alcohol extract, decompression recycling ethanol,---ethyl acetate solvent system and water---n-butanol solvent system extracts to use water successively, combined ethyl acetate and butanol extraction liquid, after desolventizing, be residue obtainedly crude extract;
(2) ethyl acetate is got: propyl carbinol: water=2:3:5v/v/v, shake well, stratification, above is stationary phase mutually, and lower is moving phase mutually, stationary phase is full of separation spiral tube, column temperature 30 ~ 35 DEG C, main frame rotates forward, and rotating speed is 890 ~ 920r/min, then enter moving phase with the flow pump of 2mL/min, in tubing string, reach equilibrium state to two-phase solvent; By crude extract prepared by step (1), below be dissolution with solvents mutually, prepare sample solution, by sample solution sample introduction, monitor under 254nm, collect the target component that appearance time is 250 ~ 280min, 300 ~ 320min successively, namely obtain compound 1 ~ 2 successively, each structural formula of compound is as follows:
Wherein, in step (1), alcohol concn is 70%v/v.
Wherein, in step (2), column temperature is 35 DEG C.
Wherein, in step (2), rotating speed is 900r/min.
Present invention also offers compound 1 or 2 in the purposes preparing oxidation resistant medicine or health care kind.
Further, described medicine or healthcare products are medicine or healthcare products of scavenging free radicals.
Wherein, described free radical is DPPH free radical.
The present invention is by HSCCC method, and from Meconopsis integrifolia, successful separation and purification has gone out 4 kinds of flavonoid compounds, and velocity of separation is very fast, for the research of Meconopsis integrifolia basic substance is laid a good foundation.
Find after deliberation, the known compound of above-mentioned separation or new compound all have good Free-radical scavenging activity, can it can be used as oxidation resistant medicine or healthcare products.
Accompanying drawing explanation
The HSCCC color atlas of Fig. 1 Meconopsis integrifolia flower crude extract
The different volumetric molar concentration compound of Fig. 2, Vc and BHT scavenging activity on DPPH figure
The numeral " 1 " marked in figure, " 2 ", " 3 ", " 4 ", represent compound " 1 ", " 2 ", " 3 ", " 4 " successively.
Embodiment
The preparation of embodiment 14 kinds of flavones ingredients
(1) crude extract preparation
Take Meconopsis integrifolia flower 10g, powder beater is pulverized, and powder is not more than 0.3mm (basic all by No. 3 sieves), add 70% ethanol (v/v) 200mL, ultrasonic (45kHz, 300w) extracts 3 times, each 45min, merge 3 filtrates, decompression recycling ethanol, obtains concentrated solution, after concentrated solution being placed in-80 DEG C of refrigerator overnight, lyophilize, obtains dry extract 3.11g, and dry extract yield is 31.1%.
Get medicinal extract and be about 150mg, use 50mL water dissolution, be transferred in separating funnel, use ethyl acetate and n-butanol extraction successively, combined ethyl acetate and butanol extraction liquid, 45 DEG C of decompression and solvent recoveries, gained crude extract is for subsequent use.
(2) separation and purification
Two-phase solvent system 2L is altogether configured by ethyl acetate/n-butanol/water (2:3:5, v/v/v), shake well, stratification in separating funnel.Below be stationary phase mutually, lower is moving phase mutually, to be dissolved in by the sample medicinal extract prepared under 20mL mutually, for subsequent use.
Being full of separation spiral tube with the flow velocity of 20mL/min by solvent systems pumping into mutually main frame, circulator bath temperature 35 DEG C, UV determined wavelength 254nm, rotating speed 900r/min, rotating forward.After stabilization of speed, pump into lower phase with flow velocity 2.0mL/min, flow out until lower from tubing string outlet and after baseline stability, sample solution injected by sample introduction circle, according to each chromatographic peak component (see Fig. 1) of color atlas manual collection, compound 1 ~ 4 can be obtained respectively.
Wherein, collecting appearance time is the position of 250 ~ 280min, and after removal of solvent under reduced pressure, remaining solid substance is compound 1 (60mg);
Collecting appearance time is the position of 300 ~ 320min, and after removal of solvent under reduced pressure, remaining solid substance is compound 2 (40mg);
Collecting appearance time is the position of 360 ~ 390min, and after removal of solvent under reduced pressure, remaining solid substance is compound 3 (16mg);
Collecting appearance time is the position of 420 ~ 450min, and after removal of solvent under reduced pressure, remaining solid substance is compound 4 (11mg).
Appearance time of the present invention was counted from the time pumping into upper phase.The present invention is very fast to the velocity of separation of each composition, whole sepn process, terminates institute and takes time from pumping into solvent is separated to peak and be only 480min.
Structural Identification
Compound 1: yellow powder, ESI-MS (negative ion mode): m/z625.16.Compound 1
1h-NMR and
13c-NMR data are in table 2 and table 3.The data of the data of compound 1 and middle quercetin-3-O-β-D-glucopyrannosy-(1 → 6)-β-D-glucopyranoside of document [16] are basically identical.
Compound 2: yellow powder, ESI-MS (negative ion mode): the secondary fragment ion that m/z667.22, MS/MS produce has m/z625.13,607.13,301.01.Compound 2
1h-NMR and
13c-NMR data are in table 2 and table 3.The data of quercetin3-O-in the data of compound 2 and document [17] [2 " '-O-acetyl-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside] are basically identical.
Compound 4: yellow powder, ESI-MS (negative ion mode): m/z667.23.The molecular weight of compound 4 is consistent with the molecular weight of compound 2.The secondary fragment ion that MS/MS produces has m/z625.13,607.13,301.01, consistent with compound 2, lost fragment CH
3cOO, C
2h
5o
3, C
14h
23o
12, and the two
1h-NMR and
13c-NMR data are similar, and be isomers both visible, aglycon is Quercetin.Difference is the coupled position of ethanoyl and Quercetin glycosides.In HMBC collection of illustrative plates, the C=O (δ of ethanoyl
c169.7) and δ
h4.66 are correlated with, δ
h4.66 and C-2 " ' (δ
c71.2) and C-4 " ' (δ
c67.6) relevant, in HSQC collection of illustrative plates, δ
h4.66 and C-3 " ' (δ
c77.8) relevant, therefore, ethanoyl and C-3 can be determined " ' be connected, compound 4 is quercetin3-O-[3 " '-O-acetyl-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside].
Compound 3: yellow powder, ESI-MS (negative ion mode): m/z667.24.The secondary fragment ion that MS/MS produces has m/z625.16,607.16,301.01, consistent with compound 2 and compound 4, lost fragment CH
3cOO, C
2h
5o
3, C
14h
23o
12, and nuclear magnetic data is also similar with compound 4 to compound 2.Difference is the coupled position of ethanoyl and Quercetin glycosides.In HMBC collection of illustrative plates, C=O (δ in ethanoyl
c170.3) and δ
h3.93 and 4.10 are correlated with, and illustrate that ethanoyl may be connected with a methylene radical.In HSQC collection of illustrative plates, δ
h3.93 and 4.10 and δ
c63.5 (C-6 " ') are relevant, it can thus be appreciated that, ethanoyl and C-6 " ' be connected, compound 3 is quercetin3-O-[6 " '-O-acetyl-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside].
Table 2
Note: (solvent is methanol-d for compound 1 (solvent is dmso) and compound 2
4) by 400MHz nmr determination; Compound 3 (solvent is dmso) and compound 4 (solvent is dmso) are by 600MHz nmr determination; Compound 1 chemical shift ownership reference, other compounds chemical shift ownership according to DEPT,
1h-
1hCOSY, HSQC and HMBC data.
Table 3 compound 1 ~ 4
13cNMR data
Note: (solvent is methanol-d for compound 1 (solvent is dmso) and compound 2
4) by 400MHz nmr determination; Compound 3 (solvent is dmso) and compound 4 (solvent is dmso) are by 600MHz nmr determination; Compound 1 chemical shift ownership reference, other compounds chemical shift ownership according to DEPT,
1h-
1hCOSY, HSQC and HMBC data.
The preparation of embodiment 22 kinds of known flavones ingredients
(1) crude extract preparation
Take Meconopsis integrifolia flower 10g, powder beater is pulverized, and powder is not more than 0.3mm (basic all by No. 3 sieves), add 70% ethanol (v/v) 200mL, ultrasonic (45kHz, 300w) extracts 3 times, each 45min, merge 3 filtrates, decompression recycling ethanol, obtains concentrated solution, after concentrated solution being placed in-80 DEG C of refrigerator overnight, lyophilize, obtains dry extract 3.11g, and dry extract yield is 31.1%.
Get medicinal extract and be about 150mg, use 50mL water dissolution, be transferred in separating funnel, use ethyl acetate and n-butanol extraction successively, combined ethyl acetate and butanol extraction liquid, 45 DEG C of decompression and solvent recoveries, gained crude extract is for subsequent use.
(2) separation and purification
Two-phase solvent system 2L is altogether configured by ethyl acetate/n-butanol/water (2:3:5, v/v/v), shake well, stratification in separating funnel.Below be stationary phase mutually, lower is moving phase mutually, to be dissolved in by the sample medicinal extract prepared under 20mL mutually, for subsequent use.
Being full of separation spiral tube with the flow velocity of 20mL/min by solvent systems pumping into mutually main frame, circulator bath temperature 35 DEG C, UV determined wavelength 254nm, rotating speed 900r/min, rotating forward.After stabilization of speed, pump into lower phase with flow velocity 2.0mL/min, flow out until lower from tubing string outlet and after baseline stability, sample solution injected by sample introduction circle, according to each chromatographic peak component (see Fig. 1) of color atlas manual collection, compound 1 ~ 4 can be obtained respectively.
Wherein, collecting appearance time is the position of 250 ~ 280min, and after removal of solvent under reduced pressure, remaining solid substance is compound 1;
Collecting appearance time is the position of 300 ~ 320min, and after removal of solvent under reduced pressure, remaining solid substance is compound 2.
Appearance time of the present invention was counted from the time pumping into upper phase.
Embodiment 3 the compounds of this invention anti-oxidant activity is studied
1 material
Generally analyse TU-1950 ultraviolet spectrophotometer (Beijing Pu Xi company); METTLERAE240 type electronic balance (plum Teller--holder benefit (Shanghai) Co., Ltd.), KQ-250B ultrasonic cleaner (Kunshan Ultrasonic Instruments Co., Ltd.).
DPPH (Ti Xiai (Shanghai) changes into industrial development company limited); Xitix (Guangdong Guanghua Science and Technology Co., Ltd.); BHT (Chengdu Ke Long chemical reagent factory), other reagent are analytical pure, and water is distilled water.Laboratory sample: compound 1quercetin-3-O-β-D-glucopyrannosy-(1 → 6)-β-D-glucopyranoside, compound 2quercetin3-O-[2 " '-O-acetyl-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, compound 3quercetin3-O-[6 " '-O-acetyl-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, compound 4quercetin3-O-[3 " '-O-acetyl-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside.Above laboratory sample adopts embodiment 1 method to be separated and obtains.
2 methods
The preparation of DPPH solution: precision takes DPPH powder 7.30mg, adds dehydrated alcohol and is settled in 50mL volumetric flask, obtain DPPH storing solution.By storing solution redilution 5 times, obtain that concentration is 0.074mmol/L, absorbancy be about 0.7 DPPH working fluid.
The preparation of sample solution: it is appropriate that precision takes sample powder, adds H
2o is mixed with 0.32mmol/L storing solution, H during mensuration
2o is diluted to 0.16mmol/L, 0.08mmol/L, 0.04mmol/L, 0.02mmol/L, 0.005mmol/L.
3 remove DPPH ability measures
DPPH radical scavenging activity measuring method is with reference to the method for [18] such as ZhouG.Pipette samples solution 0.4mL different concns sample solution and 2.6mLDPPH working fluid, in colorimetric cylinder, after lucifuge reaction 1h, measure absorbance in 517nm place.With H
2o replaces sample solution as blank, and replace sample and DPPH solution as blank using dehydrated alcohol, with Vc and BHT of same concentrations for positive control, clearance rate is calculated as follows.
A in formula
sfor blank, namely 70% ethanol adds the absorbancy of DPPH solution; A
ifor the absorbancy of different concns sample solution and DPPH solution; A
0for the absorbancy of blank.
4 results and discussion
Different substances concentration samples and the clearance rate of positive control Vc and BHT to DPPH are shown in Fig. 2, IC
50value is respectively compound 1 (0.057mmol/L), compound 2 (0.051mmol/L), compound 3 (0.049mmol/L), compound 4 (0.067mmol/L), Vc (0.159mmol/L), and under this concentration gradient, the maximum DPPH clearance rate of BHT more than 50%, therefore cannot calculate IC
50value.
As can be seen from the results, the ability that the compound 1 ~ 4 spending middle separation to obtain from Meconopsis integrifolia removes DPPH free radical is better than Vc and BHT, has good anti-oxidant activity.
Reference
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Claims (10)
1. the method for separation and purification 4 kinds of flavones ingredients while of spending middle from Meconopsis integrifolia, is characterized in that: it comprises following operation steps:
(1) flower of papaveracease meconopsis plant Meconopsis integrifolia Meconopsisintegrifolia (Maxim.) Franch. is got, pulverize, with 60 ~ 70%v/v ethanol for solvent extracts, collect alcohol extract, decompression recycling ethanol, successively with water-ethyl acetate solvent system and water-n-butanol solvent system extraction, combined ethyl acetate and butanol extraction liquid, after desolventizing, be residue obtainedly crude extract;
(2) ethyl acetate is got: propyl carbinol: water=2:3:5v/v/v, shake well, stratification, above is stationary phase mutually, and lower is moving phase mutually, stationary phase is full of separation spiral tube, column temperature 30 ~ 35 DEG C, main frame rotates forward, and rotating speed is 890 ~ 920r/min, then enter moving phase with the flow pump of 2mL/min, in tubing string, reach equilibrium state to two-phase solvent; By crude extract prepared by step (1), below be dissolution with solvents mutually, prepare sample solution, by sample solution sample introduction, monitor under 254nm, collect the target component that appearance time is 250 ~ 280min, 300 ~ 320min, 360 ~ 390min, 420 ~ 450min successively, namely obtain compound 1 ~ 4 successively, each structural formula of compound is as follows:
2. preparation method according to claim 1, is characterized in that: in step (1), and alcohol concn is 70%v/v.
3. preparation method according to claim 1, is characterized in that: in step (2), and column temperature is 35 DEG C.
4. preparation method according to claim 1, is characterized in that: in step (2), and rotating speed is 900r/min.
5. spend the middle method being simultaneously separated 2 kinds of flavones ingredients from Meconopsis integrifolia, it is characterized in that: it comprises following operation steps:
(1) flower of papaveracease meconopsis plant Meconopsis integrifolia M.integrifolia (Maxim.) Franch. is got, pulverize, with 60 ~ 70%v/v ethanol for solvent extracts, collect alcohol extract, decompression recycling ethanol, successively with water-ethyl acetate solvent system and water-n-butanol solvent system extraction, combined ethyl acetate and butanol extraction liquid, after desolventizing, be residue obtainedly crude extract;
(2) ethyl acetate is got: propyl carbinol: water=2:3:5v/v/v, shake well, stratification, above is stationary phase mutually, and lower is moving phase mutually, stationary phase is full of separation spiral tube, column temperature 30 ~ 35 DEG C, main frame rotates forward, and rotating speed is 890 ~ 920r/min, then enter moving phase with the flow pump of 2mL/min, in tubing string, reach equilibrium state to two-phase solvent; By crude extract prepared by step (1), below be dissolution with solvents mutually, prepare sample solution, by sample solution sample introduction, monitor under 254nm, collect the target component that appearance time is 250 ~ 280min, 300 ~ 320min successively, namely obtain compound 1 ~ 2 successively, each structural formula of compound is as follows:
6. preparation method according to claim 5, is characterized in that: in step (1), and alcohol concn is 70%v/v.
7. preparation method according to claim 5, is characterized in that: in step (2), and column temperature is 35 DEG C.
8. preparation method according to claim 5, is characterized in that: in step (2), and rotating speed is 900r/min.
9. compound 1 or 2 is preparing the purposes of oxidation resistant medicine or health care kind.
10. purposes according to claim 9, is characterized in that: described medicine or healthcare products are medicine or the healthcare products of removing DPPH free radical.
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|---|---|---|---|---|
| CN108752403A (en) * | 2018-06-04 | 2018-11-06 | 西南民族大学 | The method of separating meletin rhamnoside from subdigitate wormwood herb |
| CN109705178A (en) * | 2018-12-28 | 2019-05-03 | 贵阳中医学院 | A kind of compound extracted from Sabia parviflora Wall.ex Roxb and its extraction process and application |
| CN115006451A (en) * | 2022-06-29 | 2022-09-06 | 西藏天虹科技股份有限责任公司 | Process for extracting total flavone of Tibetan medicine artemisia selengensis |
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| CN102250170A (en) * | 2011-05-19 | 2011-11-23 | 浙江农林大学 | Preparation method and application of two active flavonoid glycosides in okra fruits |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108752403A (en) * | 2018-06-04 | 2018-11-06 | 西南民族大学 | The method of separating meletin rhamnoside from subdigitate wormwood herb |
| CN108752403B (en) * | 2018-06-04 | 2021-02-05 | 西南民族大学 | Method for separating quercetin rhamnoside from artemisia rupestris |
| CN109705178A (en) * | 2018-12-28 | 2019-05-03 | 贵阳中医学院 | A kind of compound extracted from Sabia parviflora Wall.ex Roxb and its extraction process and application |
| CN109705178B (en) * | 2018-12-28 | 2022-12-27 | 贵州中医药大学 | Compound extracted from caulis Sinomenii, and its extraction process and application |
| CN115006451A (en) * | 2022-06-29 | 2022-09-06 | 西藏天虹科技股份有限责任公司 | Process for extracting total flavone of Tibetan medicine artemisia selengensis |
| CN115006451B (en) * | 2022-06-29 | 2023-11-03 | 西藏天虹科技股份有限责任公司 | Extraction process of Tibetan medicine artemisia rupestris total flavone |
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| Publication number | Publication date |
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| CN105131063B (en) | 2018-04-03 |
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