CN104013610A - Application of kaempferol in preparation of medicines for preventing and treating radiation-induced pulmonary injury - Google Patents
Application of kaempferol in preparation of medicines for preventing and treating radiation-induced pulmonary injury Download PDFInfo
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Abstract
The invention discloses application of kaempferol in preparation of medicines for preventing and treating radiation-induced pulmonary injury. The experiment proves that kaempferol can obviously improve inflammatory exudation of lung tissues suffering from the mouse radiation-induced pulmonary injury and has an excellent positive effect on the radiation-induced pulmonary injury. The invention provides a novel drug for radiation-induced pulmonary injury diseases. A novel thought is provided for research and development of medicines for treating the radiation-induced pulmonary injury, and the application path of kaempferol in the field of medicines is widened.
Description
Technical field
The one that the present invention relates to kaempferol is newly applied, and is specifically related to the application of kaempferol in control induced lung injury medicine, and the preparation making taking kaempferol as medicine material.
Background technology
Induced lung injury (radio-pulmonary lesion) is due to the malignant tumor of chest is carried out to the complication that radiotherapy causes, sees at most pulmonary carcinoma, breast carcinoma, is secondly the radiotherapy to the esophageal carcinoma, mediastinum malignant tumor.Because the scope of radiological dose, radiation position and radiation is different, the weight of injury of lung is variant, and serious meeting forms interstitial pulmonary fibrosis.In the time there is injury of lung, the means of taking are at present stop radiotherapy or treat to the ill.At present the medicine of radiotherapy injury of lung is fewer, and more conventional healing potion is hormone, and hormone can immunosuppressant, is unfavorable for life-time service.Therefore, research and develop new effective medicine very necessary.
Kaempferol (Kaempferol), has another name called Kaempferol, kaempferol, Kaempferol, kaempferol, thesine, is extensively present in vegetable, fruit and Chinese herbal medicine, as all contained kaempferol in tea, Caulis et Folium Brassicae capitatae, Fructus Vitis viniferae, Semen Ginkgo, the Radix Astragali etc.Kaempferol is a kind of flavone compound of low relative molecular mass, its chemistry by name 3,5,7-trihydroxy-2-(4-hydroxy phenyl)-4H-1-benzopyran-4-one, there is the effects such as antiinflammatory, antioxidation, antibacterial, antitumor, antiallergic, analgesia, anxiety, osteoporosis.But have not yet to see the report of kaempferol aspect the effect of control induced lung injury.
Summary of the invention
The object of this invention is to provide a kind of new medical usage of kaempferol, i.e. the application of kaempferol in preparation control induced lung injury medicine.
Another object of the present invention is to provide the pharmaceutical preparation of the control induced lung injury making taking kaempferol as medicine material.
Kaempferol is one effect medicine widely, and its structural formula is as follows.There is no at present the report of kaempferol aspect induced lung injury.Inventor is in the time of the medicine of research treatment control induced lung injury, kaempferol to similar and formononetin are tested simultaneously, in the time of research, find, kaempferol has good Study On The Radioprotective, can obviously improve the inflammatory exudation of mice induced lung injury lung tissue, can reduce after mice radiotherapy the content of TNF-α, IL-6 in serum, improve total SOD vigor in mice serum, the injury of lung causing for x-ray bombardment has certain preventive and therapeutic effect.And although formononetin is also and kaempferol similar, not Study On The Radioprotective.
Kaempferol structural formula
formononetin structural formula
According to above research, kaempferol can be used as the effective ingredient of radiotherapy injury of lung, itself and adjuvant can be mixed and made into different dosage forms, such as injection, tablet or capsule etc.
Kaempferol can also be composite to the effective effective ingredient of induced lung injury with other, makes compound medicinal formulation.
The invention provides the new purposes of kaempferol aspect control induced lung injury, find through experiment, kaempferol can obviously improve the inflammatory exudation of mice induced lung injury lung tissue, and induced lung injury is had to good positive role.The present invention, for induced lung injury disease provides a kind of new medicine, for the research and development of induced lung injury medicine provide new thinking, has also expanded the application approach of kaempferol at field of medicaments.
Brief description of the drawings
Fig. 1 respectively organizes mouse lung and organizes HE coloration result: A Normal group; B irradiation group merely; C irradiation+high dose kaempferol group; D irradiation+low dosage kaempferol group; E irradiation+amifostine group; The simple administration group of F (HE dyeing, × 200).
Fig. 2 Western blot detects the expression of results of each group of mouse lung histone.
Fig. 3 respectively organizes mouse lung and organizes NF-κ B p65 expression of results: A Normal group; B irradiation group merely; C irradiation+high dose kaempferol group; D irradiation+low dosage kaempferol group; E irradiation+amifostine group; The simple administration group of F (immunohistochemical staining, × 400).
Fig. 4 respectively organizes mouse lung and organizes I κ B-alpha expression result: A Normal group; B irradiation group merely; C irradiation+high dose kaempferol group; D irradiation+low dosage kaempferol group; E irradiation+amifostine; The simple administration group of F (immunohistochemical staining, × 400).
Fig. 5 respectively organizes mouse lung and organizes JNK expression of results: A Normal group; B irradiation group merely; C irradiation+high dose kaempferol group; D irradiation+low dosage kaempferol group; E irradiation+amifostine group; The simple administration group of F (immunohistochemical staining, × 400).
Fig. 6 respectively organizes mouse lung and organizes p44/42 expression of results: A Normal group; B irradiation group merely; C irradiation+high dose kaempferol group; D irradiation+low dosage kaempferol group; E irradiation+amifostine group; The simple administration group of F (immunohistochemical staining, × 400).
Fig. 7 respectively organizes mouse lung and organizes p38 expression of results: A Normal group; B irradiation group merely; C irradiation+high dose kaempferol group; D irradiation+low dosage kaempferol group; E irradiation+amifostine group; The simple administration group of F (immunohistochemical staining, × 400).
Fig. 8 respectively organizes mouse lung and organizes HE coloration result: A Normal group; B irradiation group merely; C irradiation+high dose formononetin group; D irradiation+low dosage formononetin group (HE dyeing, × 200).
Detailed description of the invention
Below by the Study On The Radioprotective of animal experiment study kaempferol.The present invention's kaempferol, formononetin used can have been bought in market.
kaempferol Study On The Radioprotective animal experiment study
1, agents useful for same preparation
(1) kaempferol solution: get 100mg kaempferol, be dissolved in the mixed solvent of F68 of DMSO, propylene glycol, PEG400 and 5wt% that 25ml volume ratio is 1:2:2:5, be configured to the solution of 4mg/ml, keep in Dark Place in 4 DEG C of refrigerators.
(2) amifostine solution: get amifostine 10mg, be dissolved in 2.5ml normal saline, be configured to the amifostine solution of 4mg/ml, now with the current.
(3) pentobarbital sodium solution: get 100mg pentobarbital sodium, be dissolved in 10ml normal saline, be configured to the pentobarbital sodium solution of 1wt%, now with the current.
2, experimental technique
2.1 laboratory animal groupings
Before experiment, adopt table of random number method that 100 BABL/C mices are divided into six groups at random: 10 of (1) Normal groups, (2) 20 of simple irradiation groups, (3) 20 of irradiation+high dose kaempferol groups, (4) 20 of irradiation+low dosage kaempferol groups, (5) 20 of irradiation+amifostine groups, 10 of (6) simple administration groups.
The method for building up of 2.2 induced lung injury animal models
Mice is after 1% pentobarbital sodium solution (50mg/kg) intraperitoneal anesthesia, dorsal position is fixed on homemade fixing head, the xiphoid-process that ensures each mice is positioned at same level position, stereotype shielding head and abdominal part, with the full chest x-ray irradiation of 225KV toy irradiation instrument, single dose is 10 Gy, source range 50cm.
2.3 medications and processing
(1) Normal group: virtual irradiation, pre-irradiation 30min to after irradiating in 8 weeks weekly twice through mouse tail vein injection 0.1ml normal saline;
(2) irradiation group merely: the full chest irradiation 10Gy of single, pre-irradiation 30min is to twice tail vein injection 0.1ml normal saline weekly in 8 weeks after irradiating;
(3) irradiation+high dose kaempferol group: the full chest irradiation 10Gy of single, pre-irradiation 30min is to twice tail vein injection kaempferol solution (20mg/kg) weekly in 8 weeks after irradiating;
(4) irradiation+low dosage kaempferol group: the full chest irradiation 10Gy of single, pre-irradiation 30min is to twice tail vein injection kaempferol solution (10mg/kg) weekly in 8 weeks after irradiating;
(5) irradiation+amifostine group: the full chest irradiation 10Gy of single, pre-irradiation 30min is to twice tail vein injection amifostine solution (20mg/kg) weekly in 8 weeks after irradiating;
(6) simple administration group: virtual irradiation, pre-irradiation 30min is to double injection 0.1ml kaempferol solution (20mg/kg) weekly in after irradiating 8 weeks.
2.4 collections of specimens and detection index
Each group mice is anaesthetized with 50mg/kg pentobarbital sodium solution (1%) respectively at irradiating for latter 24 hours, 1 week, 2 weeks, 4 weeks, 8 weeks, cut off mice beard, win eyeball of mouse with the curved tweezer of aseptic ophthalmology and get blood, in the 1.5ml EP pipe that blood collecting is crossed in autoclave sterilization, leave standstill 30min to 1 hour, the centrifugal 20min of 2000g/min, collects serum and is placed in-20 DEG C of preservations after packing.The dead 2-4 in an each component other places mice subsequently, takes out bilateral pulmonary tissue, with the residual blood of normal saline flushing of pre-cooling, use filter paper suck dry moisture, left pulmonary tissue specimen is fixed by neutral formalin, paraffin embedding, 4 μ m thickness sections, for HE dyeing and immunohistochemical staining.
Detect each group of mice NF – κ B, MAPK Signal Transduction Pathways associated protein component expression by Western Blot and SABC, detect total SOD vigor in serum by xanthine oxidase, detect IL-6, TNF-alpha levels in serum by Elisa method.Analyze the impact of kaempferol on NF-κ B and MAPK channel marking protein expression and the impact on downstream protein expression, thereby explore the mechanism of kaempferol control induced lung injury.
3, experimental result
3.1 mouse lungs organize gross specimen to observe
Normal group, simple administration group mice lungs outward appearance pinkiness, smooth surface, elasticity is good, without congested, petechia, is normal lung tissue.
Simple irradiation group: 24h after irradiating, lung outward appearance is ruddy, can have petechia, and elasticity is fair; The 2nd week, slightly swelling of the lobe of the lung, a small amount of fresh petechia, matter is soft, and elasticity is poor; The 4th week, lobe of the lung swelling, volume increases, visible lamellar ecchymosis, tangent plane has foam sample liquid body to ooze out; The 8th week, lobe of the lung swelling, color depth is red, poor flexibility, surface is dispersed in dim purple petechia, and tangent plane still has a small amount of kermesinus courage and uprightness to ooze out.
Irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group mouse lung tissue are congested, hemorrhage, swelling, ooze out that all more simple irradiation group is light; No significant difference between irradiation+low dosage administration group, irradiation+high dose administration group, irradiation+amifostine group.
3.2 HE coloration results and the classification of mice alveolitis
3.2.1HE coloration result
Normal group and simple administration group mouse lung organize alveolar wall interval very thin, and capillary wall is complete, without obviously oozing out and hyperemia, and organizational structure complete display.
Simple irradiation group is irradiated and is started to occur inflammatory cell infiltration in latter 24 hours, is mainly neutrophilic granulocyte, extends in time, and inflammatory exudation presents and increases the weight of trend.After irradiating, 2 weeks inflammatory exudations are the most obvious, the visible a large amount of inflammatory cells of alveolar septum, and the common congestion and edema of lung tissue, alveolar septum thickens, alveolar space distortion.After irradiating, 4 weeks visible interstitial lungs thicken, and there is pulmonary consolidation part, and alveolar space dwindles, and has proliferation of fibroblast in various degree, and alveolar space inner cellulose, erythrocyte, tissue fluid are oozed out.Irradiate after 8 weeks as seen hemorrhage, hyperemia before alleviate, alveolar wall thickens, local consolidation, emphysema and pulmonary belb, granulation tissue hyperplasia.
Irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group and irradiation+amifostine group: pneumonia is more simple irradiation group mild degree all.
Each group lung tissue HE coloration result is shown in Fig. 1.
3.2.2 respectively organize the classification of mice alveolitis
Each group mice alveolitis degree is in table 1.As can be seen from the table: simple irradiation group and Normal group pneumonia degree difference have statistical significance (p<0.05).Irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group and all more simple irradiation group mild degrees (p<0.05) of irradiation+amifostine group pneumonia.Irradiation+kaempferol group and irradiation+amifostine group pneumonia degree difference not statistically significant (p>0.05).
The total SOD vitality test of 3.3 serum result
The total SOD vigor of each group mice serum is in table 2.As can be seen from Table 2: the simple total SOD vigor of irradiation group mice serum compared with normal matched group SOD in serum level obviously reduces (p=0.016); Irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group, the total SOD vigor of irradiation+amifostine group serum compared with normal matched group decrease (p>0.05), but more simple irradiation group obviously increases (p<0.05); The total SOD vigor of serum difference not statistically significant (p>0.05) between irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group and irradiation+amifostine group.
TNF-alpha expression quantitative determination in 3.4 serum
Each group mice serum TNF-alpha levels is in table 3.As can be seen from Table 3: simple irradiation group mice serum TNF-alpha levels compared with normal matched group TNF-α level obviously raise (p<0.001).Irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group, irradiation+amifostine group TNF-α level irradiation group more merely obviously reduce (p<0.05), and the horizontal no difference of science of statistics of TNF-α (p>0.05) between each group.
In 3.5 serum, IL-6 expression is measured
Each group mice serum IL-6 level is in table 4.As can be seen from Table 4: irradiation group merely, irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group, the horizontal compared with normal matched group of irradiation+amifostine group mice serum IL-6 IL-6 obviously raise (being p<0.001), but irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group, irradiation+amifostine group mice serum IL-6 level irradiation group more merely obviously reduce (p=0.021; P=0.01; P=0.008).IL-6 difference not statistically significant (being p>0.05) between irradiation+high dose kaempferol group, irradiation+low dosage kaempferol group and irradiation+amifostine group.
3.6 Western blot results
Western blot(western blotting) expression of results that detects each group of mouse lung histone is shown in Fig. 2.As can be seen from the figure:
Normal group and simple administration group lung tissue NF-κ B p65, JNK, p44/42, p38 have a small amount of expression, NF-κ B p65, JNK, p44/42, p38 in simple irradiation group compared with normal matched group express increase, irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group and simple irradiation group comparison, the expression of NF-κ B p65, JNK, p44/42, p38 all reduces.
Normal group and simple administration group lung tissue I κ B-alpha expression are more, and the I κ B-alpha expression in simple irradiation group compared with normal matched group reduces; Irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group and simple irradiation group comparison, the expression of I κ B-α all raises.See Fig. 2.
3.7 ImmunohistochemistryResults Results
In each group mouse lung tissue, the expression of NF-κ B p65, I κ B-α, JNK, p44/42, p38 is shown in Fig. 3-Fig. 7.
As can be seen from Figure 3: Normal group and the simple in-house NF-κ of administration group mouse lung B p65 positive cell number are less, paler colour, nucleus is interior without positive expression; And simple irradiation group NF-κ B p65 positive cell quantity obviously increases and color burn, in nucleus, NF-κ B p65 expresses increases; Irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group are organized NF-κ B p65 in thinner karyon with simple irradiation and are expressed reduction; Between irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group, NF-κ B p65 expresses no significant difference.
As can be seen from Figure 4: Normal group and the simple in-house I κ of administration group mouse lung B-α positive cell number are more, and color is darker; And simple irradiation group I κ B-α positive cell quantity obviously reduces, and paler colour; Irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group and the relatively I κ B-alpha expression increase of simple irradiation group; I κ B-alpha expression no significant difference between irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group.
Can find out from Fig. 5-7: Normal group and the simple in-house JNK of administration group mouse lung, p44/42, p38 positive cell are less, and color is more shallow; And irradiation group JNK, p44/42, p38 positive cell quantity obviously increase merely, and color is darker; Relatively JNK, p44/42, p38 express minimizing with simple irradiation group for irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group; The expression no significant difference of JNK, p44/42, p38 between irradiation+low dosage kaempferol group, irradiation+high dose kaempferol group, irradiation+amifostine group.
4, conclusion
Can find out from above-mentioned experimental result, kaempferol can obviously improve the inflammatory exudation of mice induced lung injury lung tissue, and induced lung injury is had to certain preventive and therapeutic effect, and its prevention effect and amifostine are close.
Kaempferol can reduce after mice radiotherapy the content of TNF-α, IL-6 in serum, improves total SOD vigor in mice serum, infers that thus kaempferol may be to be used for bringing into play radioprotective effect by what suppress NF-κ B, MAPK path.
two, the animal experiment study of formononetin Study On The Radioprotective
1, agents useful for same preparation
(1) formononetin solution: get 100mg formononetin, be dissolved in 25ml deionized water, regulate PH to 7.4, be configured to the solution of 4mg/ml, keep in Dark Place in 4 DEG C of refrigerators.
(2) pentobarbital sodium solution: get 100mg pentobarbital sodium, be dissolved in 10ml normal saline, be configured to the pentobarbital sodium solution of 1wt%, now with the current.
2, experimental technique
2.1 laboratory animal groupings
Before experiment, adopt table of random number method that 30 BABL/C mices are divided into four groups at random: 6 of (1) Normal groups, 6 of (2) simple irradiation groups, 9 of (3) irradiation+high dose formononetin groups, 9 of (4) irradiation+low dosage formononetin groups.
2.2, the method for building up of induced lung injury animal model
Mice is after 1% pentobarbital sodium solution (50mg/kg) intraperitoneal anesthesia, dorsal position is fixed on homemade fixing head, the xiphoid-process that ensures each mice is positioned at same level position, stereotype shielding head and abdominal part, with the full chest x-ray irradiation of 225KV toy irradiation instrument, single dose is 10 Gy, source range 50cm.
2.3, medication and processing
(1) Normal group: virtual irradiation, pre-irradiation 30min to after irradiating in 8 weeks weekly twice through mouse tail vein injection 0.1ml normal saline;
(2) irradiation group merely: the full chest irradiation 10Gy of single, pre-irradiation 30min is to twice tail vein injection 0.1ml normal saline weekly in 8 weeks after irradiating;
(3) irradiation+high dose formononetin group: the full chest irradiation 10Gy of single, pre-irradiation 30min is to twice tail vein injection formononetin solution (20mg/kg) weekly in 8 weeks after irradiating;
(4) irradiation+low dosage formononetin group: the full chest irradiation 10Gy of single, pre-irradiation 30min is to twice tail vein injection formononetin solution (10mg/kg) weekly in 8 weeks after irradiating;
2.4, collection of specimens and processing
Each group mice was put to death 2-3 mice respectively at after irradiating 1 week, 2 weeks, 4 weeks with 50mg/kg pentobarbital sodium solution (1%) anesthesia, taking-up bilateral pulmonary tissue, with the residual blood of the normal saline flushing of pre-cooling, use filter paper suck dry moisture, left pulmonary tissue specimen is fixed by neutral formalin, paraffin embedding, 4 μ m thickness sections, observe each group of mice pneumonia situation for HE dyeing.
3, experimental result
3.1 mouse lungs organize gross specimen to observe
Normal group mice lungs outward appearance pinkiness, smooth surface, elasticity is good, without congested, petechia, is normal lung tissue.
Simple irradiation group: irradiate latter 1 week, lung outward appearance is ruddy, congested, has petechia, and elasticity is fair; The 2nd week, slightly swelling of the lobe of the lung, a small amount of fresh petechia, matter is soft, and elasticity is poor; The 4th week, lobe of the lung swelling, volume increases, visible lamellar ecchymosis, tangent plane has foam sample liquid body to ooze out; The 8th week, lobe of the lung swelling, color depth is red, poor flexibility, surface is dispersed in dim purple petechia, and tangent plane still has a small amount of kermesinus courage and uprightness to ooze out.
Irradiation+low dosage formononetin group, irradiation+high dose formononetin group mouse lung tissue are congested, hemorrhage, swelling, to ooze out more simple irradiation group difference not obvious.
3.2 HE coloration results and the classification of mice alveolitis
3.2.1 HE coloration result
Normal group mouse lung organizes alveolar wall interval very thin, and capillary wall is complete, without obviously oozing out and hyperemia, and organizational structure complete display.
Simple irradiation group occurs being mainly neutrophilic granulocyte by inflammatory cell infiltration after irradiating for 1 week, extends in time, and inflammatory exudation presents and increases the weight of trend.After irradiating, 2 weeks inflammatory exudations are the most obvious, the visible a large amount of inflammatory cells of alveolar septum, and the common congestion and edema of lung tissue, alveolar septum thickens, alveolar space distortion.After irradiating, 4 weeks visible interstitial lungs thicken, and there is pulmonary consolidation part, and alveolar space dwindles, and has proliferation of fibroblast in various degree, and alveolar space inner cellulose, erythrocyte, tissue fluid are oozed out.
Irradiation+high dose formononetin group, irradiation+low dosage formononetin group: pneumonia irradiation group more merely degree slightly alleviates.
Each group lung tissue HE coloration result See Figure 8.
3.2.2 respectively organize the classification of mice alveolitis
Each group mice alveolitis degree is in table 5.As can be seen from the table: simple irradiation group and Normal group pneumonia degree difference have statistical significance (p<0.05).Irradiation+high dose formononetin group, all more simple irradiation group no difference of science of statistics (p>0.05) of irradiation+low dosage formononetin group pneumonia.
Above result can find out that formononetin can not effectively prevent and treat induced lung injury.This shows, in the application of radiotherapy injury of lung, even if kaempferol and formononetin structure are very similar, but can not there is identical effect.In like manner, whether to be also used for induced lung injury treatment unknown with other materials of kaempferol similar, requires further study.
Claims (3)
1. the application of kaempferol in preparation control induced lung injury medicine.
2. application according to claim 1, is characterized in that: described medicine is injection, tablet or capsule.
3. a medicine of preventing and treating induced lung injury, is characterized in that: effective ingredient comprises kaempferol.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104388489A (en) * | 2014-11-10 | 2015-03-04 | 中山大学 | Microbial hydroxylation conversion method and application of flavone compounds |
| CN111297848A (en) * | 2018-12-11 | 2020-06-19 | 香港科技大学深圳研究院 | Application of kaempferol and analogues thereof |
| CN111358780A (en) * | 2020-03-18 | 2020-07-03 | 烟台汉麻生物技术有限公司 | Application of formononetin in preparation of medicine for preventing and treating severe acute pancreatitis, tablet, dripping pill and injection emulsion |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103251583A (en) * | 2013-05-16 | 2013-08-21 | 李宝生 | Application of quercetin in drug for preventing and treating acute radiation pneumonitis and preparation prepared from quercetin |
-
2014
- 2014-06-10 CN CN201410254249.5A patent/CN104013610A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103251583A (en) * | 2013-05-16 | 2013-08-21 | 李宝生 | Application of quercetin in drug for preventing and treating acute radiation pneumonitis and preparation prepared from quercetin |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104388489A (en) * | 2014-11-10 | 2015-03-04 | 中山大学 | Microbial hydroxylation conversion method and application of flavone compounds |
| CN104388489B (en) * | 2014-11-10 | 2017-10-27 | 中山大学 | A kind of microbial hydroxylation method for transformation of chromocor compound and application |
| CN111297848A (en) * | 2018-12-11 | 2020-06-19 | 香港科技大学深圳研究院 | Application of kaempferol and analogues thereof |
| CN111358780A (en) * | 2020-03-18 | 2020-07-03 | 烟台汉麻生物技术有限公司 | Application of formononetin in preparation of medicine for preventing and treating severe acute pancreatitis, tablet, dripping pill and injection emulsion |
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