CN107007591A - A kind of application of polymethoxyflavone on the medicine for preparing treatment melanoma - Google Patents
A kind of application of polymethoxyflavone on the medicine for preparing treatment melanoma Download PDFInfo
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- CN107007591A CN107007591A CN201710123220.7A CN201710123220A CN107007591A CN 107007591 A CN107007591 A CN 107007591A CN 201710123220 A CN201710123220 A CN 201710123220A CN 107007591 A CN107007591 A CN 107007591A
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- 201000001441 melanoma Diseases 0.000 title claims abstract description 40
- 229930182496 polymethoxyflavone Natural products 0.000 title claims abstract description 19
- 239000003814 drug Substances 0.000 title claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 17
- 238000011740 C57BL/6 mouse Methods 0.000 claims abstract description 7
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 claims abstract 2
- OBIOZWXPDBWYHB-UHFFFAOYSA-N Nobiletin Natural products C1=CC(OC)=CC=C1C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 OBIOZWXPDBWYHB-UHFFFAOYSA-N 0.000 claims abstract 2
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 claims abstract 2
- 229960001587 hesperetin Drugs 0.000 claims abstract 2
- AIONOLUJZLIMTK-UHFFFAOYSA-N hesperetin Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-UHFFFAOYSA-N 0.000 claims abstract 2
- 235000010209 hesperetin Nutrition 0.000 claims abstract 2
- FTODBIPDTXRIGS-UHFFFAOYSA-N homoeriodictyol Natural products C1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 FTODBIPDTXRIGS-UHFFFAOYSA-N 0.000 claims abstract 2
- MRIAQLRQZPPODS-UHFFFAOYSA-N nobiletin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 MRIAQLRQZPPODS-UHFFFAOYSA-N 0.000 claims abstract 2
- 241000699670 Mus sp. Species 0.000 claims description 4
- 229930003944 flavone Natural products 0.000 claims description 4
- 235000011949 flavones Nutrition 0.000 claims description 4
- 238000011081 inoculation Methods 0.000 claims description 3
- 150000002213 flavones Chemical class 0.000 claims description 2
- JDVPHCLYMGBZLE-UHFFFAOYSA-N 5-Hydroxy-3,3',4',6,7,8-hexamethoxyflavone Chemical class C1=C(OC)C(OC)=CC=C1C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1 JDVPHCLYMGBZLE-UHFFFAOYSA-N 0.000 abstract description 7
- 230000012010 growth Effects 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 230000004083 survival effect Effects 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 57
- 210000004027 cell Anatomy 0.000 description 41
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 8
- 239000001963 growth medium Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 3
- -1 flavone compound Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 230000010190 G1 phase Effects 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- XFYYZBJXMSDKCV-UHFFFAOYSA-N 2-(3-hydroxy-4-methoxyphenyl)-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one Natural products C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 XFYYZBJXMSDKCV-UHFFFAOYSA-N 0.000 description 1
- ZAIANDVQAMEDFL-UHFFFAOYSA-N 3-methoxy-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(OC)=C1C1=CC=CC=C1 ZAIANDVQAMEDFL-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 230000009946 DNA mutation Effects 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 206010000583 acral lentiginous melanoma Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000003161 choroid Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010262 high-speed countercurrent chromatography Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 210000002752 melanocyte Anatomy 0.000 description 1
- YEHDMSUNJUONMW-UHFFFAOYSA-N methoxyflavone Natural products COC1=CC=CC=C1C1=CC(=O)C2=CC=CC=C2O1 YEHDMSUNJUONMW-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003032 molecular docking Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Melanoma is treated the present invention relates to polymethoxyflavone.The active ingredient of the invention includes the one or more in hesperetin, Nobiletin, senensetin, 5 five polymethoxyflavones of hydroxyl 3,6,7,3', 4', 5 hydroxyl 3,6,7,8,3', 4' hexa methoxy flavones, the polymethoxyflavones of 5 hydroxyl 6,7,4' tri-.After polymethoxyflavone of the present invention is acted on 48 hours, the survival rate of human melanoma cell line A2058 and A375 cell is respectively 42% and 26%；Compared with control group, polymethoxyflavone of the present invention improves 2.75 times to the inhibitory action for being inoculated with the C57bl/6 mouse interior tumors growth of human melanoma cell line A375 cells.
Description
Technical field
The present invention relates to a kind of application of polymethoxyflavone on the medicine for preparing treatment melanoma.
Background technology
Melanoma is that a kind of evil formed after canceration occurs for the melanocyte at the positions such as skin, mucous membrane and ocular choroid
Property tumour, be grade malignancy highest in skin neoplasin, easily occur DISTANT METASTASES IN tumour.The original site of melanoma is generally
Vola, toes, finger tips and first are inferior.For white people such as America and Europes, the principal element for forming melanoma be when skin by
To after ultraviolet irradiation, what caused DNA mutation was formed.And for the acral lentiginous melanoma in Asia and African Territories, its disease
Because being still not clear at present.It is relevant with period residing for melanoma for the therapeutic effect of melanoma, I phase, II phase, III phase IV
5 years survival rates of phase melanoma patients are respectively 94%, 44%, 38%, 4.6%.The melanoma patients of early stage, in biopsy
After making a definite diagnosis, typically treated by the operation of primary tumor expanded resection, middle and later periods patient, after surgery excision, in addition it is also necessary to carry out
Chemicotherapy is treated.Because the ulcer ratio of China's patient's melanoma is high, the difficulty of surgery excision is had influence on.So, exploitation is new
Melanoma therapeutic scheme, improve melanoma therapeutic effect, it appears it is very urgent.Polymethoxyflavone is class connection
The flavone compound of 4 or more than 4 methoxyl groups, is widely present in plant, especially with Rutaceae citrus plant
Content is enriched the most；Pass through overcritical silica gel column chromatography repeatedly, CO2Supercritical extraction, ultrasonic assistant method, ion exchange
The methods such as method, high-speed countercurrent chromatography extract separation.Due to polymethoxyflavone class compound have suppress cancer cell growth,
The bioactivity such as anti-inflammatory, anti-oxidant, prevention cardiovascular and cerebrovascular disease, suppression growth of pathogenic bacteria, is widely paid close attention to.
The content of the invention
A kind of medicine treated suitable for melanoma.The medicine is that polymethoxyflavone is preparing treatment melanoma
Application on medicine.
The concentration of polymethoxyflavone of the present invention is 0.1 μm of ol/L-1000 μm of ol/L, when using on demand
Concentration, is dissolved in the DMSO that mass concentration is 2%.
(English is entitled for 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones of the present invention：5-hydroxy-3,6,
7,8,3 ', 4 '-hexamethoxyflavone) to human melanoma cell line A2058 and A375 cell growth inhibition
Application method is：100 μ l are added in every liter of DMEM culture medium containing 31.25-500 μm of ol 5- hydroxyls -3,6,7,8,3', 4'- six
The 2%DMSO solution of methoxy flavone；After cultivating 24 hours and 48 hours respectively, cell is collected, each processing human melanin is determined
Oncocyte system A2058 and A375 cells light absorption value, calculate semilethal rate.
5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones of the present invention is to inoculation human melanoma cell line
The application method of C57bl/6 mouse interior tumor growth inhibition effect of the A375 cells after 7 days is：C57bl/6 mouse are divided into 2
Group, every group 8.The time interval fed once by 2 days, it is molten that DMSO control groups feed the DMSO that 0.4ml mass concentrations are 2%
Liquid, 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones treatment group feed 0.4ml containing 0.5 μm of ol 5- hydroxyl -3,6,7,8,
The DMSO solution of 3', 4'- hexa methoxy flavones, experiment mice is located after human melanoma cell line A375 cells are inoculated with 28 days
Extremely, tumour growth situation is detected.
The device have the advantages that：
Polymethoxyflavone of the present invention is widely present in plant, can by a variety of method separation and Extractions,
Can directly it be bought from the Reagent Company of separation and Extraction, raw material sources are extensive.Melanoma, energy are treated using polymethoxyflavone
Enough suppress the growth of human melanoma cell, 5- hydroxyls -3,6 of the present invention, the docking of 7,8,3', 4'- hexa methoxies flavones
The inhibitory action for planting human melanoma cell line A375 C57bl/6 mouse interior tumors growth improves 2.75 times.The present invention
The exploitation of new melanoma treatment method can be instructed, be future to 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones
Development and application provides new direction and strategy.
Brief description of the drawings
Fig. 1 is that 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones suppresses human melanoma cell line A2058 and A375
The influence of cell growth.
Fig. 2 is that 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones suppression human melanoma cell line A375 cells wither
The influence died.
Fig. 3 is that 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones suppression human melanoma cell line A375 cells are lured
Lead the influence of C57bl/6 mice tumors grews.
Embodiment
Embodiment 1：5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones to human melanoma cell line A2058 and
The growth of A375 cells and the influence of cell cycle distribution
The cell cultivated is human melanoma cell line A2058 and A375 cell, and culture medium is DMEM culture mediums, is contained
100U/ml penicillin and 100 μ g/ml streptomysin, 10% hyclone, cultivation temperature are 37 DEG C, and gas concentration lwevel is
5%.The DMSO solution that 100 μ l mass concentrations are 2% is added in every liter of DMEM culture medium；Added in every liter of DMEM culture medium
The 2%DMSO solution of 5- hydroxyl -3,6,7,8,3', 4'- hexa methoxy flavones of the 100 μ l containing 3.125 μm of ol；In every liter of DMEM training
Support the 2%DMSO solution that 5- hydroxyl -3,6,7,8,3', 4'- hexa methoxy flavones of the 100 μ l containing 6.25 μm of ol is added in base；
The 2% of 5- hydroxyl -3,6,7,8,3', 4'- hexa methoxy flavones of the 100 μ l containing 12.5 μm of ol is added in every liter of DMEM culture medium
DMSO solution；5- hydroxyl -3,6,7,8,3', 4'- hexa methoxies of the 100 μ l containing 25.0 μm of ol is added in every liter of DMEM culture medium
The 2%DMSO solution of flavones；5- hydroxyl -3,6,7,8,3's of the 100 μ l containing 50.0 μm of ol is added in every liter of DMEM culture medium,
After the 2%DMSO solution of 4'- hexa methoxy flavones, culture 48h, cell is collected, each processing human melanoma cell line is determined
The light absorption value of A2058 and A375 cells, calculates semilethal rate (Fig. 1).
In order to further understand that 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones suppresses human melanoma cell life
The long mechanism of action, we add 100 μ in the different human melanoma cell line A375 cell culture mediums of one liter of volume respectively
L 2%DMSO solution；The 2%DMSO for adding 5- hydroxyl -3,6,7,8,3', 4'- hexa methoxy flavones of the 100 μ l containing 25 μm of ol is molten
Liquid；5- hydroxyls -3,6 of the 100 μ l containing 50 μm of ol is added, the 2%DMSO solution of 7,8,3', 4'- hexa methoxy flavones cultivates cell
After 48h, cell is collected into centrifuge tube, is washed with the PBS of 4 DEG C of precoolings after cell, add 70% ethanol of -20 DEG C of precoolings and mix
Even, 4 DEG C stand overnight after fixed cell, and 1000rpm centrifugations discard ethanol, add appropriate PBS solution, and adjustment cell density is
(1-2)×106Individual cell/ml, adds the RNA that final concentration of 50 μ g/ml PI and final concentration of 50g/ml pollute without DNA enzymatic
After enzyme, room temperature lucifuge dyeing 30min, the cell cycle distribution feelings of flow cytomery human melanoma cell line A375 cells
Condition, all experimental results are repeated 3 times, and are averaged.Test result indicates that, compared with 2%DMSO is only added, cell culture medium
After 25 μm of ol/L or 50 μm of ol/L 5- hydroxyls -3,6 of middle addition, 7,8,3', 4'- hexa methoxy flavones, Humanmachine tumour can be caused
Accumulation of the cell line A375 cells in the sub- G1 phases, the cell in sub- G1 phases phase accounts for the ratio of all culture cells by control group
1.4% bring up to 9.4% and 25% (Fig. 2).As a result show that 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones can be induced
Apoptosis occurs for human melanoma cell.
Embodiment 2：5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones is lured human melanoma cell line A375 cells
Lead the influence of C57bl/6 mice tumors grews
C57bl/6 mouse are divided into 2 groups, every group 8.Time interval once is fed by 2d, 0.4ml mass is fed respectively
Concentration is molten for 2% DMSO of DMSO solution, 0.4ml containing 0.5 μm of ol 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxy flavones
Liquid, inoculation human melanoma cell line A375 cells put to death mouse after 28 days, detect each group C57bl/6 mouse interior tumor groups
The size (Fig. 3) knitted.Test result indicates that, 5- hydroxyls -3,6, the gross tumor volume of 7,8,3', 4'- hexa methoxy flavones is
890mm3, the gross tumor volume of 2% DMSO solution treatment group is 2450mm3, and 5- hydroxyls -3,6,7,8,3', 4'- hexa methoxies are yellow
The gross tumor volume of ketone treatment group is significantly less than 2% DMSO solution treatment group, shows the activity with stronger melanoma.
Claims (5)
1. a kind of application of polymethoxyflavone on the medicine for preparing treatment melanoma.
2. the application described in claim 1, it is characterised in that polymethoxyflavone include hesperetin, Nobiletin, senensetin,
The polymethoxyflavone of 5- hydroxyls -3,6,7,3', 4'- five, 5- hydroxyls -3,6,7,8,3 ', 4 '-hexamethyl flavones, 5- hydroxyl -6,7,
One kind in the polymethoxyflavones of 4'- tri-, two or more.
3. the application described in claim 1, it is characterised in that used cell line be human melanoma cell line A2058 and
A375 cells.
4. the application described in claim 1, it is characterised in that the tumour suppressed is C57bl/6 mouse inoculation Humanmachine tumours
After cell line A375 cells, the tumour produced by C57bl/6 Mice Bodies.
5. the application described in claim 1, it is characterised in that the concentration of described polymethoxyflavone is 0.1 μm of ol/L-
1000μmol/L。
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190046498A1 (en) * | 2017-08-11 | 2019-02-14 | Huanggang normal university | Method for treating melanoma |
| CN110483463A (en) * | 2019-09-09 | 2019-11-22 | 南开大学 | Aurora kinase-B antagonist and its application |
| CN112601461A (en) * | 2018-08-01 | 2021-04-02 | 弗门尼舍有限公司 | Polymethoxylated flavones as sweetness enhancers |
| CN113801084A (en) * | 2021-10-14 | 2021-12-17 | 三峡大学 | Polymethoxyflavone extracted from orange vinegar fermentation substrate sludge, and extraction method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20190046498A1 (en) * | 2017-08-11 | 2019-02-14 | Huanggang normal university | Method for treating melanoma |
| US10682332B2 (en) * | 2017-08-11 | 2020-06-16 | Huanggang normal university | Method for treating melanoma |
| CN112601461A (en) * | 2018-08-01 | 2021-04-02 | 弗门尼舍有限公司 | Polymethoxylated flavones as sweetness enhancers |
| CN112601461B (en) * | 2018-08-01 | 2021-10-22 | 弗门尼舍有限公司 | Polymethoxylated flavones as sweetness enhancers |
| CN110483463A (en) * | 2019-09-09 | 2019-11-22 | 南开大学 | Aurora kinase-B antagonist and its application |
| CN113801084A (en) * | 2021-10-14 | 2021-12-17 | 三峡大学 | Polymethoxyflavone extracted from orange vinegar fermentation substrate sludge, and extraction method and application thereof |
| CN113801084B (en) * | 2021-10-14 | 2023-11-28 | 三峡大学 | Polymethoxy flavone extracted from orange vinegar fermentation substrate sludge, extraction method and application |
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Application publication date: 20170804 |