CN102462727A - Yulangsan general flavone and action of monomer component thereof in preparation of anti-tumor medicament - Google Patents
Yulangsan general flavone and action of monomer component thereof in preparation of anti-tumor medicament Download PDFInfo
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- CN102462727A CN102462727A CN2010105472388A CN201010547238A CN102462727A CN 102462727 A CN102462727 A CN 102462727A CN 2010105472388 A CN2010105472388 A CN 2010105472388A CN 201010547238 A CN201010547238 A CN 201010547238A CN 102462727 A CN102462727 A CN 102462727A
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Abstract
The invention discloses a novel anti-tumor plant extract and a monomer compound. A general flavone and a series of monomer flavonoid compounds are separated from root of leguminous plant millettia pulchra kurz var.laxior (Dunn) Z.Wei (common name yulangsan) serving as a raw material by performing solvent extraction and adopting a plurality of chromatography method, and the structures thereof are verified. As proved by an in-vitro anti-tumor experiment, the general flavone and twelve monomer compounds have remarkable restraining effects on a plurality of severe tumors, and can be used for inducing apoptosis of tumors through a mitochondrial pathway. Through oral administration of the general flavone, mouse S180 sarcomas, liver cancers H22 and human nude mouse implanted breast cancers can be restrained remarkably. Due to the adoption of the Yulangsan general flavone and the monomer flavonoid compounds, pilot compounds are provided for the research and development of novel anti-tumor medicaments; and the Yulangsan general flavone and the monomer flavonoid compounds can be clinically taken as novel medicaments for preventing and treating cancers.
Description
Technical field
The present invention relates to the effect in the preparation anti-tumor medicine of YULANGSAN total flavones and monomeric compound composition thereof.
Background technology
YULANGSAN; Have another name called the Arillus Longan ginseng; Dredge the tuber of leaf precipice bean (Millettia pulchra kurz var.laxior Dunn Z.Wei) for pulse family (Leguminosae) butterfly type flower subfamily (Papilionaceae) precipice bean Calamus (Millettia) plant; For Guangxi Zhuang, precious jade doctor medicinal herbs most in use, be recorded in " Guangxi Chinese medicinal herbal " at first, be used to treat infantile malnutrition, puerperal and after being ill weakness, treating swelling and pain by traumatic injury, fracture, Fengshi Guanjie swell and ache, apoplectic hemiplegia, mental retardation of children and senile dementia etc.; The effect of have promoting blood circulation to remove blood stasis, reducing swelling and alleviating pain, allaying excitement is one of main Chinese medicinal materials of Chinese medicinal liniment " repercussive and analgesic tincture ".YULANGSAN contains multiple compositions such as flavone, saponin, polysaccharide, it is reported, Yulangsan polysaccharide can be protected the damage of hepatocyte injury and acute cerebral ischemia and can remove ultra-oxygen anion free radical and hydroxy radical; The YULANGSAN flavone can reduce essential hypertension; Increase coronary flow and reduce myocardial ischemic injury; Can remove ultra-oxygen anion free radical and hydroxy radical, xylol causes mice ear, carrageenin causes the mice foot swelling and the rat acute pleuritis is inhibited.The objective of the invention is to extract preparation YULANGSAN total flavones and monomeric compound thereof and study its antitumor action, for this resourceful national medicinal plants of YULANGSAN provides the new approach that utilizes.
Summary of the invention
Said YULANGSAN total flavones of the present invention and monomeric compound extract from YULANGSAN (Millettia pulchra kurz var.laxior Dunn Z.Wei).Raw material in
2005Year
6The moon picks up from
Guangxi, through being accredited as
Leguminous plant is dredged the root (YULANGSAN) of leaf precipice bean
Among the present invention, the YULANGSAN total flavones and separate from wherein 12 monomer flavone compound karanjins (MPL-01), 2 ', β-dimethoxy-furan-[2 ", 3 ": 4 '; 3 ']-dihydrochalcone (MPL-04), 2 '-methoxyl group-furan-[2 ", 3 ": 4 ', 3 ']-chalcone (MPL-06), furan-[2 ", 3 ": 7; 8]-flavone (MPL-07), 2 ", 2 " dimethyl-pyrans-[and 5 ", 6 ": 7; 8] flavone (MPL-08), 2 '-methoxyl group-furan-[2 ", 3 ": 7,8]-flavone (MPL-09), [2] .alpha.-5:6-benzopyran [4; 3-b]-furo [2,3-h] [1] .alpha.-5:6-benzopyran-6 (10H)-ketone (MPL-10), 6-methoxyl group-2 ", 2 " dimethyl-pyrans-[and 5 "; 6 ": 7,8] flavone (MPL-11), formononetin (MPL-12), 5-methoxyl group-2 ", 2 " dimethyl-pyrans-[and 5 "; 6 ": 7,8] flavone (MPL-13), 7-methoxyl group-3 " hydroxyl-3 "-methyl-8-(1 " cyclobutenyl)-flavone (MPL-16), 6-hydroxyl-2 ", 2 " dimethyl-pyrans-[5 "; 6 ": 7,8] flavone (MPL-17) all has the growth inhibiting effect of kinds of tumor cells, and inducing apoptosis of tumour cell; Wherein can have remarkable inhibitory action to mice S180 sarcoma, hepatocarcinoma H22 in the YULANGSAN total flavones body.
6-hydroxyl-2 among the present invention ", 2 " dimethyl-pyrans-[5 ", 6 ": 7,8] flavone is new chemical compound.
YULANGSAN total flavones and monomer component can be used with appropriate carriers pharmaceutically among the present invention, can be made into tablet, injection, capsule, oral liquor and other types of formulations.
Advantage of the present invention:
(1) the present invention separates YULANGSAN total flavones and the flavone monomer component obtain and has remarkable anti-tumor activity and inducing apoptosis of tumour cell;
(2) technology of extraction separation YULANGSAN total flavones of the present invention and flavone monomer component is simple;
(3) the present invention lays a good foundation for the development of new type anticancer medicine.
The specific embodiment
The extraction separation and the evaluation of embodiment one YULANGSAN total flavones and known monomers chemical compound
Use 50% alcohol reflux again after adopting 90% alcohol heating reflux to extract, the chemical compound of its each polarity section is fully extracted, the extracting solution concentrating under reduced pressure obtains pure extractum.Alcohol extractum adds dissolution with solvents, admixes adsorbent (silica gel, kieselguhr etc.), with opposed polarity solvent (normal hexane, ethyl acetate, methanol etc.) eluting, pure extractum is divided into normal hexane, ethyl acetate and methanol part in the cable type extractor according of packing into after mixture dries.Wherein the normal hexane part mainly contains flavone, is the total flavones part.Remove normal hexane part cream and ethyl acetate part cream after desolvating through silica gel column chromatography, LH-20 gel filtration chromatography and prepare means such as TLC separates and has identified 11 chemical compounds; Be respectively karanjin (MPL-01), 2 ', β-dimethoxy-furan-[2 ", 3 ": 4 '; 3 ']-dihydrochalcone (MPL-04), 2 '-methoxyl group-furan-[2 ", 3 ": 4 ', 3 ']-chalcone (MPL-06), furan-[2 "; 3 ": 7,8]-flavone (MPL-07), 2 ", 2 " dimethyl-pyrans-[and 5 "; 6 ": 7,8] flavone (MPL-08), 2 '-methoxyl group-furan-[2 ", 3 ": 7; 8]-flavone (MPL-09), [2] .alpha.-5:6-benzopyran [4,3-b]-furo [2,3-h] [1] .alpha.-5:6-benzopyran-6 (10H)-ketone (MPL-10), 6-methoxyl group-2 "; 2 "-dimethyl-pyrans-[5 ", 6 ": 7,8] flavone (MPL-11), formononetin (MPL-12), 5-methoxyl group-2 "; 2 "-dimethyl-pyrans-[5 ", 6 ": 7,8] flavone (MPL-13), 7-methoxyl group-3 " hydroxyl-3 "-methyl-8-(1 " cyclobutenyl)-flavone (MPL-16).
The title and the structure of separating the chemical compound that obtains in table 1 YULANGSAN
*：new?natural?product，**：new?compound
The separation of embodiment two noval chemical compounds and structure are identified
1. the separation of noval chemical compound
YULANGSAN medical material 12kg, the alcohol heating reflux of pulverizing back 90% extracts 3 times, and each 1 hour, the extracting solution pressurization concentrated, and concentrated solution and 800 gram kieselguhr are mixed thoroughly, dry, and the kieselguhr mixture is successively with normal hexane, ethyl acetate and methanol-eluted fractions; Hexane eluting part is separated through silica gel column chromatography, and hexane: acetone (2: 1) is eluant, and 154-173 part obtains noval chemical compound 6-hydroxy-2 through gel filtration chromatography ", 2 " dimethylpyrano-[5 ", 6 ": 7,8] flavone 30mg.
2. All new compounds is resolved
Noval chemical compound 6-hydroxy-2 ", 2 " dimethylpyrano-[5 ", 6 ": 7,8] the structural member Fig.1.1 of flavone
Noval chemical compound is a yellow crystal type powder, and mp ℃, ° (c 0.6, CHCl in [α]=-0.002
3).EI-MS m/z:320M
+(40), 305 [M-CH
3]
+(100), 289 [M-CH
3-O]
+, 203 [M-CH
3-B]
+In conjunction with carbon spectrum and its molecular formula of hydrogen spectrum release is C
20H
16O
4, degree of unsaturation is 13, points out this chemical compound possibly have 2 or 2 above benzene ring structures.IR (KBr) v
MaxCm
-1: the characteristic absorption at places such as 3301,1625,1587 shows that hydroxyl is arranged in the molecule, conjugation carbonyl, aromatic ring etc.UV λ
MaxNm (log ε) in MeOH:224,245,281,341 (3.64, end absorption) have the flavone compound characteristic ultraviolet absorption, and pointing out this chemical compound is flavone compound.
1H-NMR (CDCl
3) two methyl signals δ are arranged in the spectrum: 1.56 (3H * 2 s), and all link to each other with saturated quaternary carbon.7.89 (2H m) is C on the flavone parent nucleus B ring
2 ', 6 '-H signal, 7.53 (3H m) infers and to be C on the flavone parent nucleus B ring
3 ', 4 ', 5 '-H signal (A2B2C system) shows that this compd B ring is no substituted graphic.6.95 (1H, d, J=10.0HZ); 5.79 (1H, d J=10.0HZ) are two cis alkene hydrogen signals.In addition, also have two fragrant proton signal δ: 6.78 (1H, s), 7.60 (1H, s), chemical shift is that 6.78 a unimodal hydrogen can be inferred and is 3 hydrogen of flavone.Can know that according to above hydrogen spectrum data this chemical compound is a chromocor compound.
13C-NMR (CDCl
3) show 17 carbon signals, wherein δ in the spectrum: 28.17 are two identical methyl carbon signals of chemical environment (in the hydrogen spectrum a unimodal signal that contains six hydrogen being arranged), 129.06 (C
2 ', 6 ') and 126.07 (C
3 ', 5 ') signal intensity be 2 times of other signal, should have symmetrical structure, so this chemical compound contains 20 carbon signals altogether.In addition, δ 79.12 is for connecting oxygen saturation quaternary carbon signal, and δ 177.72 is the carbonyl carbon signal, 4 company's oxygen aromatic carbon signals (143.03～162.43), 12 aromatic carbon signals (106.90～132.17).Can find out that from HMBC 1.56 and 79.12,130.33 is relevant respectively; 5.79 it is relevant respectively with 28.17,79.12,109.80; 6.95 relevant with 79.12,144.81,146.64, by having the pyranoid ring structure in these information deducibility chemical compounds, see Fig.1-2.While is δ in the HMBC spectrum: 7.53 and 132.14,126.07 is relevant, and 7.89 and 129.06,131.33,162.43 is relevant, explains that containing segment in this chemical compound sees Fig.1-3.δ in the HMBC spectrum: 6.78 and 117.85,132.14,162.43,177.72 is relevant, and δ: 6.78 should be H-3.From the HMBC spectrum, also can see δ: 7.60 and 144.81,146.64,177.72,143.03 is relevant, shows δ: 7.60 is 5 hydrogen, because 5 hydrogen are unimodal; And chemical potential displacement in C-6 position is to low field displacement to 143.03; C-5,7 equal high field of chemical shift can be inferred that the C-6 position should be and contain oxygen and replace; Because can knowing with the hydrocarbon number of NMR spectrum demonstration, m/z 320 should contain a hydroxyl in the chemical compound; IR spectrum shows that also this chemical compound contains hydroxyl in addition, replaces so the C-6 position should be hydroxyl, then can release fragment and see Fig.1-4.
Connect this three segments, confirm that All new compounds is a 6-hydroxyl-2 ", 2 " dimethyl-pyrans-[and 5 ", 6 ": 7,8] flavone (6-hydroxy-2 ", 2 " dimethylpyrano-[5 ", 6 ": 7,8] flavone) (MPL-17).
Embodiment three external anti-tumor experiments
Human tumor cells is in 5%CO
2, cultivate in DMEM culture medium that contains an amount of hyclone, green grass or young crops, streptomycin and glutamine or RPMI-1640 culture medium under 37 ℃ of conditions.Before the test, collection is in logarithmic (log) phase growing tumors cell, processes single cell suspension, adjustment cell concentration to 1 * 10
5/ ml adds variable concentrations the present invention (with the storage liquid that DMSO is made into 8mg/ml, diluting with culture medium and the adding cell by desired concn during use) matched group and adds isometric DMSO behind 37 ℃ of cultivation 24h.Every hole adds 10 μ l MTT solution (5mg/ml) behind the 48h, and 37 ℃ are continued to cultivate 4h, and careful the suction removed culture fluid in the 80 μ l holes, and every hole adds 80 μ l cell pyrolysis liquids, and crystal is fully dissolved.Measure light absorption value and calculate IC50 (50% cell growth inhibitory concentration) at enzyme-linked immunosorbent assay instrument 570nm place.
Table 2 YULANGSAN total flavones and monomeric compound are to the growth inhibited effect of 30 cell lines in seven kinds of tumors
As shown in table 2, the present invention is inhibited to 30 tumor cell lines of seven kinds of tumors, shows that YULANGSAN total flavones and 12 monomeric compounds have the broad-spectrum anti-tumor effect.
Embodiment four morphocytology experimental observation inducing apoptosis of tumour cell effects
The passage that will be in exponential phase is placed in 6 orifice plates that are placed with microscope slide, behind the cultivation 24h, adds the solution of the present invention of variable concentrations, and 37 ℃ are continued to cultivate 24h, and not dosing contrast is set simultaneously.Exhaust culture fluid, add the 0.5ml fixative, fixedly 10min.Remove fixative, wash 3 times with PBS, each 3min exhausts liquid.Wash the appropriate to the occasion shaking table of using, or manually rock.Add 0.5ml Hoechst 33258 dyeing liquors, dyeing 5min.Also should use shaking table, or manually rock for several times.Remove dyeing liquor, wash twice with PBS, each 3min exhausts liquid.Wash the appropriate to the occasion shaking table of using, or manually rock.Drip anti-fluorescent quenching mounting liquid on microscope slide, cover the coverslip that posts cell, let cells contacting mounting liquid, avoid bubble as far as possible.Under fluorescence microscope, observe and find that Normocellular nucleus is normal blueness, and the nucleus after the effect of the present invention is fine and close dense dying, or be fine and close dense the dying of chunky shape, show obvious apoptosis cell characteristic (seeing accompanying drawing 1A, Figure 1B).
The cellular morphology of the fluorescence microscope after Fig. 1 Hoechst 33258 dyeing changes (200 *) arrow and is designated as the typical apoptotic cell.
Figure 1A: the form of the normal HeLa cell of fluorescence microscope;
Figure 1B: the form of HeLa cell behind the fluorescence microscope drug effect.
The test of embodiment five apoptosis
Is 1 * 10 with cell with concentration
6/ ml is inoculated in 6 orifice plates, and 24h is hatched for 37 ℃ in the 2ml/ hole.The present invention is acted on cell 16h with variable concentrations, establish not dosing contrast.Culture fluid is collected in the test tube, washes twice, 0.25% trypsinization, collect with culture fluid, PBS washing liquid with the cold PBS of pH7.4,4 ℃ of centrifugal 5min collecting cells of 1000rpm, cold PBS washes twice.Cell is resuspended in 100 μ l, 1 * Annexin V-FITC binding buffer, adds 5 μ l Annexin V-FITC and 10 μ l PI buffer, and the room temperature lucifuge is hatched 15min.Add 400 μ l, 1 * Annexin V-FITC binding buffer, flow cytometer is analyzed.The two method testing results of dying of Annexin V-FITC/PI show that variable concentrations the present invention all can inducing apoptosis of tumour cell (seeing accompanying drawing 2).
The influence of pair cell apoptosis behind the Ovalitenin A function cells 16h of Fig. 2 variable concentrations
Fig. 2 A: (solvent) control tumor apoptosis rate
Apoptosis rate behind Fig. 2 B:5 μ g/ml Ovalitenin A effect HeLa cell 16h
Apoptosis rate behind Fig. 2 C:10 μ g/ml Ovalitenin A effect HeLa cell 16h
Apoptosis rate behind Fig. 2 D:20 μ g/ml Ovalitenin A effect HeLa cell 16h
Antitumor action in the embodiment hexasomic
1) Balb/c mice, 16-18 gram, male and female half and half, available from Beijing Vital River Experimental Animals Technology Co., Ltd., the quality certification number is SCXK (capital) 2002-0003.Animal feeding is in barrier environment, and temperature is 21-25 ℃, relative humidity 40-70%.Give conventional normal feedstuff before on-test and adapt to 5 days ~ 7 days.
2) under aseptic condition, well-grown S180, H22 oncocyte are mixed with 5 * 10
6/ ml suspension.Tumor cell suspension is inoculated in mice right fore oxter, and 0.2ml/ only.
3) inoculation back 24h is divided into 5 groups at random, 10 every group, be respectively model group (giving solvent control),
Positive drug group (compound recipe cyclophosphamide 30mg/kg, manufacturer: Tianjin Jinshi Pharmaceutical Co., Ltd., lot number: 20071101.Oral), the high, medium and low dose groups oral administration of YULANGSAN total flavones, continuous 10 days.
4) put to death mice on the 11st day, strip the tumor piece and weigh, respectively organize the heavy and calculating tumor control rate of tumor.
Tumor control rate (%)=(C-T)/C * 100, C is that the average tumor of matched group is heavy in the formula, T is that the average tumor of administration group is heavy.
Table 3 YULANGSAN total flavones is to the inhibitory action of mouse transplanted sarcoma S180, hepatocarcinoma H22
Compare with model group: * P＜0.05, * * P＜0.01.
Claims (7)
1. the method for preparing of YULANGSAN extractive of general flavone; It is characterized in that it comprises the following step: dry YULANGSAN medical material, pulverize, use 50% alcohol reflux again after extracting with 90% alcohol heating reflux; The chemical compound of its each polarity section is fully extracted, and the extracting solution concentrating under reduced pressure obtains pure extractum.Alcohol extractum adds dissolution with solvents, admixes adsorbent (silica gel, kieselguhr etc.), uses the normal hexane eluting in the cable type extractor according of packing into after mixture dries, and is YULANGSAN total flavones part.
2. method according to claim 1, dry YULANGSAN medical material is pulverized, after extracting respectively with 90% and 50% alcoholic solution, concentrating under reduced pressure filtrate pure extractum, it is mixed the kieselguhr chromatographic column of packing into, obtain the YULANGSAN extractive of general flavone with the normal hexane eluting.
Claim 1 or 2 described YULANGSAN extractive of general flavone mainly contain karanjin, 2 ', β-dimethoxy-furan-[2 ", 3 ": 4 ', 3 ']-dihydrochalcone, 2 '-methoxyl group-furan-[2 "; 3 ": 4 ', 3 ']-chalcone, furan-[2 ", 3 ": 7,8]-flavone, 2 "; 2 "-dimethyl-pyrans-[5 ", 6 ": 7,8] flavone, 2 '-methoxyl group-furan-[2 ", 3 ": 7; 8]-flavone, [2] .alpha.-5:6-benzopyran [4,3-b]-furo [2,3-h] [1] .alpha.-5:6-benzopyran-6 (10H)-ketone, 6-methoxyl group-2 ", 2 " dimethyl-pyrans-[and 5 "; 6 ": 7,8] flavone, formononetin, 5-methoxyl group-2 ", 2 " dimethyl-pyrans-[and 5 ", 6 ": 7; 8] flavone, 7-methoxyl group-3 " hydroxyl-3 "-methyl-8-(1 " cyclobutenyl)-flavone, 6-hydroxyl-2 ", 2 " dimethyl-pyrans-[5 ", 6 ": 7,8] 12 kinds of chemical compounds such as flavone.
4.6-hydroxyl-2 ", 2 " dimethyl-pyrans-[5 ", 6 ": 7,8] flavone is a kind of new chemical compound.
5. claim 1, the 2 or 3 described Yulangsan extracts purposes in preparation medicine for treating tumor thing.
6. medicine for treating tumor thing, it contains the YULANGSAN extractive of general flavone of claim 1.
Karanjin, 2 ', β-dimethoxy-furan-[2 ", 3 ": 4 ', 3 ']-dihydrochalcone, 2 '-methoxyl group-furan-[2 "; 3 ": 4 ', 3 ']-chalcone, furan-[2 ", 3 ": 7,8]-flavone, 2 "; 2 "-dimethyl-pyrans-[5 ", 6 ": 7,8] flavone, 2 '-methoxyl group-furan-[2 ", 3 ": 7; 8]-flavone, [2] .alpha.-5:6-benzopyran [4,3-b]-furo [2,3-h] [1] .alpha.-5:6-benzopyran-6 (10H)-ketone, 6-methoxyl group-2 ", 2 " dimethyl-pyrans-[and 5 "; 6 ": 7,8] flavone, formononetin, 5-methoxyl group-2 ", 2 " dimethyl-pyrans-[and 5 ", 6 ": 7; 8] flavone, 7-methoxyl group-3 " hydroxyl-3 "-methyl-8-(1 " cyclobutenyl)-flavone, 6-hydroxyl-2 ", 2 " dimethyl-pyrans-[and 5 ", 6 ": 7,8] purposes of flavone in preparation medicine for treating tumor thing.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103784432A (en) * | 2012-11-05 | 2014-05-14 | 广西壮族自治区花红药业股份有限公司 | Application of yulangsan extract in anti-inflammation |
| CN104248654A (en) * | 2013-06-26 | 2014-12-31 | 深圳海王药业有限公司 | Application of karanjin or Pongamia pinnata extract in anti-influenza virus drugs |
| CN106632178A (en) * | 2015-11-03 | 2017-05-10 | 沈阳药科大学 | Millpuline compounds and their preparation method and pharmaceutical application |
| CN115594686A (en) * | 2021-06-28 | 2023-01-13 | 沈阳药科大学（Cn） | Millpuline A derivatives, and preparation method and medical application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101040894A (en) * | 2007-04-16 | 2007-09-26 | 黄仁彬 | Preparing and application of Yulangsan extract |
| CN101181315A (en) * | 2007-11-30 | 2008-05-21 | 黄仁彬 | New purpose of Yulangsan polysaccharide |
| CN101463022A (en) * | 2008-12-01 | 2009-06-24 | 黄仁彬 | Preparation of Chinese medicine Yulansan chalcone monomer and use thereof |
-
2010
- 2010-11-17 CN CN2010105472388A patent/CN102462727A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101040894A (en) * | 2007-04-16 | 2007-09-26 | 黄仁彬 | Preparing and application of Yulangsan extract |
| CN101181315A (en) * | 2007-11-30 | 2008-05-21 | 黄仁彬 | New purpose of Yulangsan polysaccharide |
| CN101463022A (en) * | 2008-12-01 | 2009-06-24 | 黄仁彬 | Preparation of Chinese medicine Yulansan chalcone monomer and use thereof |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103784432A (en) * | 2012-11-05 | 2014-05-14 | 广西壮族自治区花红药业股份有限公司 | Application of yulangsan extract in anti-inflammation |
| CN104248654A (en) * | 2013-06-26 | 2014-12-31 | 深圳海王药业有限公司 | Application of karanjin or Pongamia pinnata extract in anti-influenza virus drugs |
| CN104248654B (en) * | 2013-06-26 | 2017-11-28 | 深圳海王药业有限公司 | The application of karanjin or Indian beech extract in anti-influenza virus medicament |
| CN106632178A (en) * | 2015-11-03 | 2017-05-10 | 沈阳药科大学 | Millpuline compounds and their preparation method and pharmaceutical application |
| CN106632178B (en) * | 2015-11-03 | 2019-03-01 | 沈阳药科大学 | Look into ear alkyl compound and preparation method thereof and medical usage |
| CN115594686A (en) * | 2021-06-28 | 2023-01-13 | 沈阳药科大学（Cn） | Millpuline A derivatives, and preparation method and medical application thereof |
| CN115594686B (en) * | 2021-06-28 | 2023-10-13 | 沈阳药科大学 | Millpulin A derivative, preparation method and medical application thereof |
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Application publication date: 20120523 |