CN101468950A - Novel compound separated from immature exocarp of Juglans mandshurica Maxim, and preparation and use thereof - Google Patents
Novel compound separated from immature exocarp of Juglans mandshurica Maxim, and preparation and use thereof Download PDFInfo
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Abstract
The invention relates to a novel compound separated form north Juglans regia and a preparation method and application thereof. The preparation method adopts a method for combining alcohol extraction, chromatographic separation and purification and cytoactive assay to separate the novel compound, which is not reported before and has anti-tumor function, from the north Juglans regia, and adopts mass spectrum and high-resolution nuclear magnetic resonance technique to determine the structure of the compound. The structural formula of the novel compound is the right formula (I). The novel compound is applied in the field of medicine.
Description
Technical field:
The present invention relates to a kind of new compound, this compound is the novel substance that extraction separation obtains from the Chinese medicine immature exocarp of Juglans mandshurica Maxim, has anti-tumor activity; The invention still further relates to the preparation method of this compound; The invention still further relates to the application of this compound in the preparation antitumor drug.
Background technology:
Cancer is the serious disease that threatens the human life, and therefore, the research of cancer therapy drug is the focus of World Focusing always.Chinese medicine is antitumor to have distinctive feature at the chemicals that compares aspect raising immunizing power and the reduction mutagenesis toxicity, therefore, from motherland's medicine treasure-house, seek the antitumor Chinese medicine of determined curative effect, clear and definite its effective substance, and then develop the new drug of high-efficiency low-toxicity, become the focus that tcm field is studied for many years.
Immature exocarp of Juglans mandshurica Maxim is the immature fruit of juglandaceae plant Juglans mandshurica (Juglans Mandshurica MAXIM.), abounds with in each county, outskirts of a town, northeast, at the anodyne that is commonly used for the various cancers of treatment and tetter and various pain among the people.Immature exocarp of Juglans mandshurica Maxim recorded and became a kind of Chinese medicine in Heilongjiang Province's medicinal material standard and be applied to clinical and produce calendar year 2001.Alimentary tract cancers such as the crude extract preparation for treating cancer of the stomach of immature exocarp of Juglans mandshurica Maxim, the esophageal carcinoma, have the case of two more than ten years treatment observation to prove (Li Zhongyuan. the 120 routine clinical observations of Exocarpium Juglandis Immaturum treatment carcinoma of esophago cardia. Chinese materia medica information, 1988, (3): 3), its antitumor action is unquestionable.Yet its effective substance research does not deeply launch, bibliographical information rests on the pharmacological action of its crude extract more and (Ji Yubin is gone up in the antitumor action research that lacks its effective constituent, the horse grand plan, Yang Bo, draw the cutting edge of a knife or a sword in morning. the antitumor action research of the different extract parts of immature exocarp of Juglans mandshurica Maxim. herbal medicine, 2004,35 (10): 1145-1147), thereby the serious hysteresis that causes this medicine resource of immature exocarp of Juglans mandshurica Maxim to be developed.We are in the research at the antitumor effective constituent of immature exocarp of Juglans mandshurica Maxim, detect the method that combines through extraction using alcohol, chromatographic separation and purification with cytoactive, finally obtained to have a new compound of anti-tumor activity, and adopt mass spectrum and high resolution NMR technology, determined the structure of this compound.This compound has good antitumour activity, can make the antitumor drug that is suitable for clinical use with drug excipient, also can be used as lead compound, its structure activity relationship is further studied, synthetic a series of cancer therapy drug and drug regimen, more can be used as the index components of the immature exocarp of Juglans mandshurica Maxim medicinal material and the quality of the pharmaceutical preparations thereof control, realize the stable and controlled of the immature exocarp of Juglans mandshurica Maxim medicinal material and the quality of the pharmaceutical preparations thereof, break through the bottleneck of present immature exocarp of Juglans mandshurica Maxim research and development.
Summary of the invention:
The purpose of this invention is to provide a kind of have anti-tumor activity, extraction separation obtains from the Chinese medicine immature exocarp of Juglans mandshurica Maxim new compound.The preparation method of this compound and the new purposes of this compound.
Above-mentioned purpose realizes by following technical scheme:
Isolating antineoplastic novel compound from immature exocarp of Juglans mandshurica Maxim, the plain A of called after Exocarpium Juglandis Immaturum, the structural formula of this compound is:
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim is got fresh immature exocarp of Juglans mandshurica Maxim and is extracted with alcohol immersion, and extracting solution concentrates, concentrated solution adds water-dispersion, gets supernatant liquor after centrifugal, and supernatant liquor passes through macroporous adsorbent resin, with the polymeric adsorbent ethanol elution, use dissolve with methanol behind the elutriant evaporate to dryness, filter the back and inject dextrane gel, collect meoh eluate, silica gel thin-layer is qualitative, merge same component, must this compound, purity 98%.
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, describedly get fresh immature exocarp of Juglans mandshurica Maxim and extract with alcohol immersion, extracting solution concentrates, be with one week of 75% alcohol immersion with fresh immature exocarp of Juglans mandshurica Maxim, extract three times, united extraction liquid is evaporated to relative density 1.10-1.14 (50 ℃).
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, described concentrated solution adds water-dispersion, get supernatant liquor after centrifugal, supernatant liquor passes through macroporous adsorbent resin, with the polymeric adsorbent ethanol elution, be meant that concentrated solution adds 10 times of water gagings and disperses, centrifugal, get supernatant liquor, be injected in the macroporous adsorbent resin of having handled well, the ratio of concentrated solution and resin is 1:50, and flow velocity is 10ml/min, respectively with the washing of 3 times of column volumes, 30% ethanol of 5 times of column volumes is washed, collect 30% ethanol eluate, the elutriant evaporated under reduced pressure is obtained residue, residue dissolves with small amount of methanol, filter the back and inject dextrane gel, collect meoh eluate, silica gel thin-layer is qualitative, merges same component, must this compound, purity 98%.
The preparation of antineoplastic novel compound in the Exocarpium Juglandis Immaturum, described filtrate is injected dextrane gel, collects meoh eluate, be meant on the filtrate injection sephadex lh-20 post, column diameter 2cm, column length 2m, applied sample amount are 1g residue/each, with methanol-eluted fractions, collect meoh eluate, silica gel thin-layer is qualitative, merges same component, must this compound, purity 98%.
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, described collection meoh eluate, silica gel thin-layer is qualitative, merge same component, be meant that elutriant carries out thin-layer chromatography on silica-gel plate, developping agent is a chloroform-methanol, volume parts merges R than being 84:16
fValue is 0.3 one-component.
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim merges R
fValue is 0.3 one-component, must this compound with recrystallizing methanol, and purity is more than 98%.
The application of isolating new compound in antitumor drug from immature exocarp of Juglans mandshurica Maxim.
This technical scheme has following beneficial effect:
1. the invention provides a kind of compound of not reporting with antitumor action, by to cancer cells inhibition test and pharmacodynamics test, proved that this compound has good antitumour activity, can make the antitumor drug that is suitable for clinical use with drug excipient.
2 adopt the screening method of these experiments this compound that caused from the Chinese medicine immature exocarp of Juglans mandshurica Maxim separation and purification, and purity reaches more than 98%.This compound is an extraction separation from natural phant, have novel structure, the unique advantage of effect, can make the antitumor drug that is suitable for clinical use with drug excipient on the one hand, also can be used as lead compound on the other hand, its structure activity relationship is further studied synthetic a series of cancer therapy drug and drug regimen.
3 Chinese medicines and the quality of the pharmaceutical preparations thereof stable and controlled be the bottleneck of the modernization of Chinese medicine always, this compound is one of effective constituent of Chinese medicine immature exocarp of Juglans mandshurica Maxim, can be used as the index of the immature exocarp of Juglans mandshurica Maxim medicinal material and the quality of the pharmaceutical preparations thereof control, setting up with this composition on this basis is the discriminating of index and the quality control standard of assay project, realize the stable and controlled of the immature exocarp of Juglans mandshurica Maxim medicinal material and the quality of the pharmaceutical preparations thereof, this compound will be extensive use of as the Chinese medicine reference substance.
Description of drawings:
Accompanying drawing 1 is a The compounds of this invention
1H-
1Observed structure iron in the H COSY spectrum.
The specific embodiment of the present invention:
Embodiment 1:
Isolating antineoplastic novel compound from immature exocarp of Juglans mandshurica Maxim, the plain A of called after Exocarpium Juglandis Immaturum, the structural formula of this compound is:
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim is got fresh immature exocarp of Juglans mandshurica Maxim and is extracted with alcohol immersion, and extracting solution concentrates, concentrated solution adds water-dispersion, gets supernatant liquor after centrifugal, and supernatant liquor passes through macroporous adsorbent resin, with the polymeric adsorbent ethanol elution, use dissolve with methanol behind the elutriant evaporate to dryness, filter the back and inject dextrane gel, collect meoh eluate, silica gel thin-layer is qualitative, merge same component, must this compound, purity 98%.
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, describedly get fresh immature exocarp of Juglans mandshurica Maxim and extract with alcohol immersion, extracting solution concentrates, be with one week of 75% alcohol immersion with fresh immature exocarp of Juglans mandshurica Maxim, extract three times, united extraction liquid is evaporated to relative density 1.10-1.14 (50 ℃).
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, described concentrated solution adds water-dispersion, get supernatant liquor after centrifugal, supernatant liquor passes through macroporous adsorbent resin, with the polymeric adsorbent ethanol elution, be meant that concentrated solution adds 10 times of water gagings and disperses, centrifugal, get supernatant liquor, be injected in the macroporous adsorbent resin of having handled well, the ratio of concentrated solution and resin is 1:50, and flow velocity is 10ml/min, respectively with the washing of 3 times of column volumes, 30% ethanol of 5 times of column volumes is washed, collect 30% ethanol eluate, the elutriant evaporated under reduced pressure is obtained residue, residue dissolves with small amount of methanol, filter the back and inject dextrane gel, collect meoh eluate, silica gel thin-layer is qualitative, merges same component, must this compound, purity 98%.
The preparation of antineoplastic novel compound in the Exocarpium Juglandis Immaturum, described filtrate is injected dextrane gel, collects meoh eluate, be meant on the filtrate injection sephadex lh-20 post, column diameter 2cm, column length 2m, applied sample amount are 1g residue/each, with methanol-eluted fractions, collect meoh eluate, silica gel thin-layer is qualitative, merges same component, must this compound, purity 98%.
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim, described collection meoh eluate, silica gel thin-layer is qualitative, merge same component, be meant that elutriant carries out thin-layer chromatography on silica-gel plate, developping agent is a chloroform-methanol, volume parts merges R than being 84:16
fValue is 0.3 one-component.
The preparation of antineoplastic novel compound in described a kind of immature exocarp of Juglans mandshurica Maxim merges R
fValue is 0.3 one-component, must this compound with recrystallizing methanol, and purity is more than 98%.
The application of isolating new compound in antitumor drug from immature exocarp of Juglans mandshurica Maxim.
Embodiment 2:
The preparation of compound
The material source immature exocarp of Juglans mandshurica Maxim is the immature fruit of juglandaceae plant Juglans mandshurica (Juglans MandshuricaMAXIM.), adopts in 5 constant virtues, Heilongjiang Province county mid-July, and the herbarium sample is concealed in Chinese herbal medicine specimen shop, institute for drug control, Heilongjiang Province.
Extract and separate fresh immature exocarp of Juglans mandshurica Maxim with one week of 75% alcohol immersion, extract altogether three times, united extraction liquid, concentrating under reduced pressure, be concentrated into the concentrated solution of relative density 1.10-1.14 (50 ℃), concentrated solution adds 10 times of water gagings and disperses, centrifugal, get supernatant liquor, inject the Diaion HP-20 macroporous adsorbent resin of having handled well (ratio of concentrated solution and resin is 1:50), flow velocity 10ml/min, respectively with the washing of 3 times of column volumes, 30% ethanol of 5 times of column volumes is washed, and collects 30% ethanol eluate, and the elutriant evaporated under reduced pressure obtains residue, residue dissolves with small amount of methanol, filter, filtrate is injected (column diameter 2cm, column length 2m on the sephadex lh-20 post, applied sample amount is a 1g residue/each), with methanol-eluted fractions, flow velocity 1.0ml/min, elutriant carry out thin-layer chromatography on silica-gel plate, developping agent is chloroform-methanol (84:16), merges R
fValue is 0.3 one-component, must this compound with recrystallizing methanol, and purity is more than 98%.
The structure determination of compound
Structure determination
With Shimadzu UV-160 spectrophotometric determination UV spectrum, with JASCOFT/IR-300E (KBr compressing tablet) spectrophotometric determination infrared spectra, measure specific rotation with JASCO DIP-370digital polarimeter, measure ESI-MS with LCQ mass analyzer, measure HR-FAB-MS with JEOL Mstation spectrometer
1H-and
13The C-NMR spectrum is marked in TMS does with JEOL ECP-500 spectrometer.
The physico-chemical property of compound:
Compound is an amorphous powder.IR(KBr)ν
max：3414，2924，2857，2372，1618，1456，1391，1263，1116，618。UV(MeOH)λ
max(logε)：209nm(3.52)，263nm(3.92)，344nm(4.41)。[α]
D 25-21°(c＝0.1，MeOH)。
1H-NMR (500MHz, CD
3OD) and
13C-NMR (125MHz, CD
3OD) the spectrum data see Table 1.ESI-MS (positive) m/z 379.1[M+Na]; HR-FAB-MS (positive) m/z 379.1002[M+Na] (calculated value C
19H
16O
7Na 379.1005).
Compound
1Show five fragrant protons in the H-NMR spectrum, at δ 6.67 (1H, dd, J=8.2,1.1), δ 7.42 (1H, dd, J=8.2,7.8), δ 7.29 (1H, dd, J=7.8,1.1) be a cover ABC coupling system, δ 6.53 (1H, s), (1H s) is the aroma system that a cover contraposition hydrogen replaces to δ 7.06, at high field region δ 2.50 (1H, dd, J=12.4,4.2), δ 2.57 (1H, dd, J=12.4,1.8) be that a methylene radical and a methyne are at δ 3.15 (1H, d, J=4.2,1.8) the ortho position coupling, its excess-three proton is respectively at δ 3.31 (1H, m) and δ 2.68 (2H, m) ortho position coupling, these
1H-
1Obtain conclusive evidence (seeing accompanying drawing 1) in the H COSY spectrum.
13C-NMR spectrum composes as can be known in conjunction with HMQC that δ 208.7 is carbonyl carbon, is respectively a methylene radical and a methyne at δ 48.9 and δ 36.7, and δ 70.9 is for being connected with the tertiary carbon of hydroxyl.δ 2.50 (H-3) in the HMBC spectrum, the methylene radical of δ 2.57 (H-3) is relevant with δ 208.7 (C-1) carbonyl, and the methyne of δ 3.15 (H-2) is relevant with δ 70.9 (C-4), can infer and contain the Tetralone an intermediate of Sertraline structure in the molecule.δ 6.67 (H-5) is relevant with δ 70.9 (C-4) in the HMBC spectrum has also proved this point, and shows that the phenyl ring in the Tetralone an intermediate of Sertraline is an ABC coupling system.An other cover aroma system is to be connected on the δ 70.9 (C-4), and this can observe the relevant peaks of δ 7.06 (H-5 ') and δ 70.9 (C-4) in HMBC spectrum.δ 3.31 in HMBC spectrum (H-7 ') and δ 116.1 (C-2 ') are relevant, and δ 6.53 (H-2 ') and δ 40.3 (C-7 ') are relevant, show that δ 40.3 (C-7 ') and δ 45.6 (C-8 ') are connected on another phenyl ring.Wherein δ 2.68 (H-8 ') is long-range relevant with 48.9 (C-2), δ 3.31 (H-7 ') long-range relevant with δ 208.7 (C-1), show that C-7 ' is connected on the C-2, this can pass through δ 3.31 (H-7 ') and δ 36.7 (C-3), δ 2.50 (H-3), the long-range relevant conclusive evidence that obtains of δ 2.57 (H-3) and δ 40.3 (C-7 ').Substituting group from the phenyl ring has two hydroxyls on the Tetralone an intermediate of Sertraline, lay respectively at C-4 and C-8, and two vicinal hydroxyl groups are arranged on another phenyl ring, and two Sauerstoffatoms are still arranged in the molecular formula, in conjunction with
13C-NMR composes (δ 176.9) data, and showing has a carboxyl to exist, and it can only be connected on the C-8 '.Therefore, compound
1H-NMR and
13The C-NMR data are arranged as table 1.From HMBC spectrum (accompanying drawing 2), the structure of this compound has obtained conclusive evidence.
Table 1 compound
1H-NMR and
13The C-NMR data
Embodiment 3:
A kind of above-claimed cpd is in the application in anticancer field.
Suppress people HL-60 leukemia cell, people Kato-III stomach cancer cell and people A
549The activity experiment of lung carcinoma cell:
Cell cultures
People HL-60 leukemia cell, people Kato-III stomach cancer cell and people A
549Lung carcinoma cell is incubated at RPMI 1640 substratum, adds 10% FBS, L-glutamine, 100U/ml penicillin and 100 μ g/ml Streptomycin sulphates.The cell counting of taking the logarithm vegetative period is with 3 * 10
4The concentration of individual/ml is inoculated in 96 orifice plates, and every hole 180 μ l are at 37 ℃, 5% CO
2Incubator in cultivated 24 hours.
Cell toxicant is measured
The medicine of different concns (1-100 μ M) is with EtOH-H
2O (1:9) is dissolution with solvents to 20 μ l, and blank group adds the EtOH-H of 20 μ l
2O (1:9) solution, cell continue to cultivate 72 hours, adopt mtt assay to measure then, and the cell after promptly cultivating adds 10 μ l MTT (5mg/ml) phosphate buffered saline buffers, 37 ℃, 5% CO
2Cultivated 4 hours in the incubator, centrifugal, get supernatant liquor 150 μ l and discard, add 175 μ l DMSO, jolting was measured light absorption value with microplate reader at 550nm after 10 minutes.Calculate according to following formula, draw IC
50
Control wells: only add cell and do not add medicine
Blank well: only solubilizing agent does not add cell and medicine
Experimental port: add cell and add medicine again
Test-results sees Table 2.The result shows, compound all has in various degree restraining effect to three kinds of tumour cells.
Table 2. compound suppresses the IC of three kinds of tumour cells
50(μ M) value
Annotate: each numerical value is the mean value ± standard deviation of three independent experiments
Pharmacodynamics test
Experimental animal: Kunming mouse, body weight 18g-22g, male and female dual-purpose.
Medicine and reagent: injection physiological saline (blank), endoxan (positive control), compound.Knurl strain: rat liver cancer H
22
Test method:
1, mouse tumor is heavily reached the influence of immune organ exponential: mouse random packet, male and female half and half.Be respectively the compound group, endoxan group, physiological saline group.Each organizes mouse in the subcutaneous conventional inoculation H of right front armpit
22Tumor cell suspension 0.2ml (about 1 * 10
6-2 * 10
6Individual cell), respectively organizes the ip administration after the inoculation, continuously 7d.Put to death mouse after the last administration, weigh, claim knurl piece, thymus gland and spleen quality, calculate tumour inhibiting rate, thymus index and spleen index.
2, to H
22The influence of mouse increase in life span: mouse peritoneal inoculation H
22Tumor cell suspension 0.2ml observes and record dead mouse situation every day.
The results are shown in following table:
Annotate: compare * P＜0.05 with the physiological saline group; Compare P＜0.05 with the endoxan group.
Compound provided by the invention is to H
22Growth has the obvious suppression effect, and can obviously prolong the mouse survival time, has good antitumor action.
Claims (8)
1. isolating antineoplastic novel compound from immature exocarp of Juglans mandshurica Maxim, the plain A of called after Exocarpium Juglandis Immaturum, it is characterized in that: the structural formula of this compound is:
2. the preparation of antineoplastic novel compound in the described a kind of immature exocarp of Juglans mandshurica Maxim of claim 1 is characterized in that: get fresh immature exocarp of Juglans mandshurica Maxim and extract with alcohol immersion, extracting solution concentrates, concentrated solution adds water-dispersion, gets supernatant liquor after centrifugal, and supernatant liquor passes through macroporous adsorbent resin, with the polymeric adsorbent ethanol elution, use dissolve with methanol behind the elutriant evaporate to dryness, filter the back and inject dextrane gel, collect meoh eluate, silica gel thin-layer is qualitative, merge same component, must this compound, purity 98%.
3. the preparation of antineoplastic novel compound in a kind of immature exocarp of Juglans mandshurica Maxim according to claim 2, it is characterized in that: describedly get fresh immature exocarp of Juglans mandshurica Maxim and extract with alcohol immersion, extracting solution concentrates, be with one week of 75% alcohol immersion with fresh immature exocarp of Juglans mandshurica Maxim, extract three times, united extraction liquid is evaporated to relative density 1.10-1.14 (50 ℃).
4. according to the preparation of antineoplastic novel compound in claim 2 or the 3 described a kind of immature exocarp of Juglans mandshurica Maxim, it is characterized in that: described concentrated solution adds water-dispersion, get supernatant liquor after centrifugal, supernatant liquor passes through macroporous adsorbent resin, with the polymeric adsorbent ethanol elution, be meant that concentrated solution adds 10 times of water gagings and disperses, centrifugal, get supernatant liquor, be injected in the macroporous adsorbent resin of having handled well, the ratio of concentrated solution and resin is 1:50, and flow velocity is 10ml/min, respectively with the washing of 3 times of column volumes, 30% ethanol of 5 times of column volumes is washed, collect 30% ethanol eluate, the elutriant evaporated under reduced pressure is obtained residue, residue dissolves with small amount of methanol, filter the back and inject dextrane gel, collect meoh eluate, silica gel thin-layer is qualitative, merges same component, must this compound, purity 98%.
5. the preparation of antineoplastic novel compound in a kind of immature exocarp of Juglans mandshurica Maxim according to claim 4 is characterized in that: described filtrate is injected dextrane gel, collects meoh eluate, be meant on the filtrate injection sephadex lh-20 post, column diameter 2cm, column length 2m, applied sample amount are 1g residue/each, with methanol-eluted fractions, collect meoh eluate, silica gel thin-layer is qualitative, merges same component, must this compound, purity 98%.
6. the preparation of antineoplastic novel compound in a kind of immature exocarp of Juglans mandshurica Maxim according to claim 5, it is characterized in that: described collection meoh eluate, silica gel thin-layer is qualitative, merge same component, be meant that elutriant carries out thin-layer chromatography on silica-gel plate, developping agent is a chloroform-methanol, and volume parts merges R than being 84:16
fValue is 0.3 one-component.
7. according to the preparation of antineoplastic novel compound in claim 2 or 3 or 4 or the 5 or 6 described a kind of immature exocarp of Juglans mandshurica Maxim, it is characterized in that: merge R
fValue is 0.3 one-component, must this compound with recrystallizing methanol, and purity is more than 98%.
8. the application of isolating new compound in antitumor drug from immature exocarp of Juglans mandshurica Maxim.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102370695A (en) * | 2010-08-19 | 2012-03-14 | 黑龙江省中医研究院 | Qinglongyi active extract, its preparation method and its application |
| CN103217491A (en) * | 2013-03-21 | 2013-07-24 | 黑龙江大学 | Method for establishing high performance liquid chromatography fingerprint spectrum of Exocarpium Juglandis Immaturum antioxidant active extract, its standard fingerprint spectrum and use |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100548957C (en) * | 2006-10-11 | 2009-10-14 | 东北林业大学 | A kind of method of extracting regianin |
| CN100567285C (en) * | 2007-04-04 | 2009-12-09 | 中国科学院兰州化学物理研究所 | Has maraniol of antitumour activity and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102370695A (en) * | 2010-08-19 | 2012-03-14 | 黑龙江省中医研究院 | Qinglongyi active extract, its preparation method and its application |
| CN102370695B (en) * | 2010-08-19 | 2014-04-16 | 黑龙江省中医研究院 | Qinglongyi active extract, its preparation method and its application |
| CN103217491A (en) * | 2013-03-21 | 2013-07-24 | 黑龙江大学 | Method for establishing high performance liquid chromatography fingerprint spectrum of Exocarpium Juglandis Immaturum antioxidant active extract, its standard fingerprint spectrum and use |
| CN103217491B (en) * | 2013-03-21 | 2014-07-23 | 黑龙江大学 | Method for establishing high performance liquid chromatography fingerprint spectrum of Exocarpium Juglandis Immaturum antioxidant active extract, its standard fingerprint spectrum and use |
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