CN104490863A - Application of isoflavone compounds to preparing medicines or health care products with anti-tumor effect - Google Patents
Application of isoflavone compounds to preparing medicines or health care products with anti-tumor effect Download PDFInfo
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- CN104490863A CN104490863A CN201410671485.7A CN201410671485A CN104490863A CN 104490863 A CN104490863 A CN 104490863A CN 201410671485 A CN201410671485 A CN 201410671485A CN 104490863 A CN104490863 A CN 104490863A
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- breast cancer
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- 239000003814 drug Substances 0.000 title claims abstract description 22
- 150000002515 isoflavone derivatives Chemical class 0.000 title claims abstract description 15
- 229940079593 drug Drugs 0.000 title claims abstract description 9
- 230000000259 anti-tumor effect Effects 0.000 title claims abstract description 7
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 33
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 33
- 230000000694 effects Effects 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 18
- QJSPPBAASCPSJB-UHFFFAOYSA-N 5-hydroxy-7-(4-methoxyphenyl)-2,2-dimethylpyrano[3,2-g]chromen-6-one Chemical compound C1=CC(OC)=CC=C1C(C(C1=C2O)=O)=COC1=CC1=C2C=CC(C)(C)O1 QJSPPBAASCPSJB-UHFFFAOYSA-N 0.000 abstract description 10
- HGHOPAZIUPORIN-UHFFFAOYSA-N 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one Chemical compound CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C(C2=O)=C1OC=C2C1=CC=C(O)C=C1 HGHOPAZIUPORIN-UHFFFAOYSA-N 0.000 abstract description 9
- GGGQCONNJCHXIR-UHFFFAOYSA-N Erythrinin A Natural products O=C1C=2C=C3C=CC(C)(C)OC3=CC=2OC=C1C1=CC=C(O)C=C1 GGGQCONNJCHXIR-UHFFFAOYSA-N 0.000 abstract description 5
- RQAMSFTXEFSBPK-UHFFFAOYSA-N alpinumisoflavone Chemical compound O=C1C=2C(O)=C3C=CC(C)(C)OC3=CC=2OC=C1C1=CC=C(O)C=C1 RQAMSFTXEFSBPK-UHFFFAOYSA-N 0.000 abstract description 5
- YKYNYMQDXOWMDT-UHFFFAOYSA-N alpinumisoflavone Natural products O=C1C=2C(O)=C3C=CC(C)(C)OC3=CC=2OC=C1C1=CC=C(O)C=C1O YKYNYMQDXOWMDT-UHFFFAOYSA-N 0.000 abstract description 5
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 abstract description 2
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 abstract description 2
- 235000008696 isoflavones Nutrition 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 201000008275 breast carcinoma Diseases 0.000 description 5
- 239000001963 growth medium Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000287 crude extract Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000034994 death Effects 0.000 description 3
- 231100000517 death Toxicity 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 241001629511 Litchi Species 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 241000628997 Flos Species 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000218231 Moraceae Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 230000002380 cytological effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001641 gel filtration chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/60—Moraceae (Mulberry family), e.g. breadfruit or fig
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to the field of medicines, in particular to application of isoflavone compounds to preparing medicines or health care products with the anti-tumor effect. Isoflavone comprises Scandenolone, 4'-O-Methylalpinumisoflavone and Alpinumisoflavone which have the certain breast cancer resisting effect; in particular, the breast cancer resisting effect of the Scandenolone is most obvious; and the application can be used for the further development of the medicines or the health care products for treating the breast cancer.
Description
Technical field
The present invention relates to field of medicaments, be specifically related to a kind of isoflavone compounds, in preparation, there is antitumor action
Medicine or health product in application.
Background technology
At present, breast carcinoma is still in female malignant sickness rate first, account for 29% of all new female malignant, and women worldwide breast cancer incidence continues rising 0.2%-8% every year: die from the case load of malignant tumor women all, because the case load of breast cancer deaths comes second, account for 14%, breast carcinoma is one of major causes of death becoming women, is only second to the case load because of lung cancer death.In conjunction with the trend that breast cancer incidence rises, we can understand: very urgent to the preventing and controlling of breast carcinoma.But but do not have a kind of medicine can reach side effect effect little, evident in efficacy, based on this, people expect to find a kind of new drug always, tool be significantly improved clinical symptoms and body constitution, side effect is little and can prevent and treat the advantages such as complication in multiple link.And the effective ingredient in Chinese medicine provides very large element to people.
Fructus Cudraniae tricuspidatae
fructus Maclurae Tricuspidataefor the fruit of moraceae plants Zhe Shu, also known as doing good son, mountain Fructus Litchi, water Fructus Litchi, Flos dendrobenthamiae angustatae, Lignum Cudraniae tricuspidatae.As the Chinese medicine of folk tradition, Fructus Cudraniae tricuspidatae can be decocted soup and take orally, for clearing away heat and cooling blood, relaxing muscles and tendons and activating QI and blood in the collateral, for traumatic injury, also has certain curative effect.At present, Lignum Cudraniae tricuspidatae syrup has been made by existing company, is used for the treatment of breast carcinoma, but is object of study and treatment material with crude extract, and curative effect is stable and very optimistic not.And if the active material ingredients in its extract is determined, really establish a capital will have very large benefit by its curative effect and initial characterization quantitative approach.But containing thousands of compounds in crude extract, specifically which compound has active anticancer the best of anti-breast cancer activity and which compound, unknown.First this need, and research worker is separated crude extract by multiple chromatograph means, purification, obtains monomeric compound, and then by the structure of multiple spectroscopic technique determination monomeric compound; Finally again active testing is carried out to monomeric compound.Therefore, from crude extract, find active monomer compound, and determine which kind of compound activity the best needs to pay a large amount of performing creative labour.
Summary of the invention
Technical problem to be solved by this invention is that providing a kind of isoflavone compounds to have antitumor in preparation does
Medicine or health product in application.
Isoflavone compounds is preparing the application in the medicine or health product with antitumor action, and described isoflavone compounds is selected from the compound of any one structure following:
;
or
.
The name of above-mentioned three kinds of compounds is called Scandenolone, 4'-O-Methylalpinumisoflavone, Alpinumisoflavone.These three kinds of compounds have document and disclose its extraction or synthetic method.But not yet there is document to disclose it and there is active anticancer, especially anti-breast cancer activity.
Preferably, described isoflavone compounds is preparing the application in the medicine or health product with anti-breast cancer effect.
Preferably, the cancerous cell in described anti-breast cancer medicines is breast cancer cell MCF-7 or breast cancer cell M231.
Preferably, described isoflavone compounds is separated to obtain from Fructus Cudraniae tricuspidatae.
Preferably, described isoflavone compounds also can synthesize to obtain or be separated from other plant and obtains.
Preferably, above-claimed cpd, together with pharmaceutically acceptable carrier, adopts the conventional method of this area to be prepared into various dosage form, as tablet, pill, capsule, granule and oral liquid etc.
Beneficial effect: the novelty teabag that present invention finds Scandenolone, 4'-O-Methylalpinumisoflavone, Alpinumisoflavone tri-kinds of compounds, there is certain anti-breast cancer effect, especially the effect of the anti-breast cancer of Scandenolone is the most remarkable, can be used for the medicine being developed further into treatment breast carcinoma.
Accompanying drawing explanation
Fig. 1 is the growth inhibited curve chart of compound S candenolone to breast cancer cell MCF-7.
Fig. 2 is the growth inhibited curve chart of compound S candenolone to breast cancer cell M231.
Fig. 3 is the growth inhibited cytological map of compound S candenolone to breast cancer cell M231.
Detailed description of the invention
Explain the present invention further below in conjunction with specific embodiment, but embodiment does not limit in any form to the present invention.
the preparation of isoflavone in embodiment 1. Fructus Cudraniae tricuspidatae
S1. after being pulverized by fresh Fructus Cudraniae tricuspidatae, with the methanol of 10 times, room temperature leaves standstill to be extracted, then extracting solution is concentrated into 1/3 of original volume, obtains stock solution;
S2. by the ethyl acetate of 8 times of volumes, stock solution is extracted, collect supernatant concentration and obtain sample;
S3. sample is passed through silica gel column chromatography, adopt petroleum ether-ethyl acetate as eluant, first carry out eluting with petroleum ether, then use petroleum ether-ethyl acetate (95:5-15:85) to carry out gradient elution, finally use eluent ethyl acetate.Every 50ml connects a fraction, and some plate merges, and collects eluent concentrate drying and obtains crystal.
S4. the coarse crystal obtained is carried out purification by gel filtration chromatography, with chloroform-methanol (1:1) as eluant, some plate merges, and collects fraction, dry concentrated; Obtain three known compounds, through Structural Identification, they are respectively Scandenolone, 4'-O-Methylalpinumisoflavone, Alpinumisoflavone.
in embodiment 2. Fructus Cudraniae tricuspidatae, isoflavone compounds is to breast cancer cellmCF-7
growth inhibited effect
collect the breast cancer cell MCF-7 of growth logarithmic (log) phase, adjust concentration of cell suspension, then bed board on 96 orifice plates by counting, every hole adds 100 μ l, make cell to be measured adjust density 4000/ hole, but the aseptic PBS of the edge hole of 96 orifice plates fills.
2. 5%CO2, hatches for 37 DEG C, starts adherent growth (96 hole flat underside) at the bottom of hole, add the medicine of Concentraton gradient (12,16,20,24,28,32,36,40 μm of ol/L) to cell.In principle, dosing is got final product after cell attachment.
3. sop up culture medium with liquid-transfering gun, then add pastille culture medium.Each concentration arranges 5 multiple holes, arranges zeroing group (adding culture medium, MTT, dimethyl sulfoxide) and matched group (add cell, culture fluid, MTT, dimethyl sulfoxide, do not add medicine) simultaneously.5%CO2, hatches 24 hours for 37 DEG C.
4. every hole adds 10 μ LMTT solution (5mg/ml, i.e. 0.5%MTT), continues to cultivate 4h.
5. carefully suck mixed solution in hole, stop cultivating.
6. first, every hole adds 100 μ L dimethyl sulfoxide, then, enzyme-linked immunosorbent assay instrument jolts 5min, and the first a ceremonial jade-ladle, used in libation of generation is fully dissolved, and then measures the absorbance in each hole at wavelength 490nm place.Draw and intend Optimal Curve (as accompanying drawing 1), calculate IC50 value.
Result shows: Scandenolone, within the scope of 12-40 μm of ol/L, obviously can suppress the growth of breast cancer cell MCF-7, and IC50 value is (24.860 ± 0.038) μm ol/L.Compare with blank group, have significant difference (P ﹤ 0.01, or P ﹤ 0.05), and strengthen along with the increase of drug level, in dose dependent; And the IC50 of 4'-O-Methylalpinumisoflavone and Alpinumisoflavone is respectively and is greater than 80 μm of ol/L and be greater than 50 μm of ol/L, there is certain inhibitory action to the growth of breast cancer cell MCF-7, but act on not obvious.
embodiment 3.scandenolone
to the growth inhibited effect of breast cancer cell M231
collect the breast cancer cell M231 of growth logarithmic (log) phase, adjust concentration of cell suspension, then bed board on 96 orifice plates by counting, every hole adds 100 μ l, make cell to be measured adjust density 4000/ hole, but the aseptic PBS of the edge hole of 96 orifice plates fills.
2. 5%CO2, hatches for 37 DEG C, starts adherent growth (96 hole flat underside) at the bottom of hole, add the medicine of Concentraton gradient (8,12,16,20,24,28,32,36,40 μm of ol/L) to cell.In principle, dosing is got final product after cell attachment.
3. sop up culture medium with liquid-transfering gun, then add pastille culture medium.Each concentration arranges 5 multiple holes, and 5%CO2, hatches 12,24,48 or 72 hours for 37 DEG C.
4. every hole adds 10 μ LMTT solution (5mg/ml, i.e. 0.5%MTT), continues to cultivate 4h.
5. carefully suck mixed solution in hole, stop cultivating.
6. first, every hole adds 100 μ L dimethyl sulfoxide, then, enzyme-linked immunosorbent assay instrument jolts 5min, and the first a ceremonial jade-ladle, used in libation of generation is fully dissolved, and then measures the absorbance in each hole at wavelength 490nm place.Draw and intend Optimal Curve (as accompanying drawing 2), calculate IC50 value.
Result shows: the growth of the obvious T suppression cell M231 of Scandenolone energy, the IC50 value being 12 hours, 24 hours, 48 hours, 72 hours in action time is respectively 21.25 μm of ol/L, 17.00 μm of ol/L, 16.25 μm of ol/L, 13.75 μm of ol/L.Above-mentioned data show, compound S candenolone has significant inhibitory action to breast cancer cell M231.
Claims (4)
1. isoflavone compounds is preparing the application in the medicine or health product with antitumor action, and described isoflavone compounds is selected from the compound of any one structure following:
;
or
.
2. application according to claim 1, is characterized in that, described isoflavone compounds is preparing the application in the medicine or health product with anti-breast cancer effect.
3. application according to claim 2, is characterized in that, the cancerous cell in described anti-breast cancer medicines is breast cancer cell MCF-7 or breast cancer cell M231.
4. application according to claim 1, is characterized in that, described isoflavone compounds is separated to obtain from Fructus Cudraniae tricuspidatae.
Priority Applications (1)
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CN201410671485.7A CN104490863A (en) | 2014-11-21 | 2014-11-21 | Application of isoflavone compounds to preparing medicines or health care products with anti-tumor effect |
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CN201410671485.7A CN104490863A (en) | 2014-11-21 | 2014-11-21 | Application of isoflavone compounds to preparing medicines or health care products with anti-tumor effect |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110283182A (en) * | 2019-04-22 | 2019-09-27 | 暨南大学 | A kind of preparation method of isoflavone compound |
KR20210083485A (en) * | 2019-12-26 | 2021-07-07 | 충북대학교 산학협력단 | A Composition for Solubilizing Alpinumisoflavone and Uses Thereof |
-
2014
- 2014-11-21 CN CN201410671485.7A patent/CN104490863A/en active Pending
Non-Patent Citations (3)
Title |
---|
RUBEN F. TCHOKOUAHA等: "Erymildbraedin A and B, two novel cytotoxic dimethylpyrano-isoflavones from the stem bark of Erythrina mildbraedii: evaluation of their activity toward endocrine cancer cells", 《JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY》 * |
YANG LIU等: "Methylalpinumisoflavone Inhibits Hypoxia-inducible Factor-1 (HIF-1) Activation by Simultaneously Targeting Multiple Pathways", 《THE JOURNAL OF BIOLOGICAL CHEMISTRY》 * |
刘志平等: "构棘果中2 个苯并吡喃异黄酮的分离及其抗肿瘤活性筛选", 《中草药》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110283182A (en) * | 2019-04-22 | 2019-09-27 | 暨南大学 | A kind of preparation method of isoflavone compound |
KR20210083485A (en) * | 2019-12-26 | 2021-07-07 | 충북대학교 산학협력단 | A Composition for Solubilizing Alpinumisoflavone and Uses Thereof |
KR102300737B1 (en) | 2019-12-26 | 2021-09-13 | 주식회사 셀젠텍 | A Composition for Solubilizing Alpinumisoflavone and Uses Thereof |
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