CN104490896A - Pharmaceutical use of protopanaxatriol or/and derivatives thereof - Google Patents
Pharmaceutical use of protopanaxatriol or/and derivatives thereof Download PDFInfo
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- CN104490896A CN104490896A CN201410707438.3A CN201410707438A CN104490896A CN 104490896 A CN104490896 A CN 104490896A CN 201410707438 A CN201410707438 A CN 201410707438A CN 104490896 A CN104490896 A CN 104490896A
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
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Abstract
The invention discloses a pharmaceutical use of protopanaxatriol or/and derivatives thereof as active ingredient(s) for preparing medicines for treating fatty liver. Research results show that the protopanaxatriol has an obvious in-vitro effect of inhibiting fat cell differentiation and also has the in-vivo effects of preventing the weight increase of high-fat meal induced fat rats, inhibiting the volume increase of body fat cells, improving fasting blood-glucose, insulin resistance and dyslipidemia and the like; in addition, PPAR gamma report gene analysis results indicate that the protopanaxatriol is capable of selectively inhibiting the transcriptional activity of PPAR gamma. In other words, the protopanaxatriol has remarkable treatment activity on the fatty liver, and also is capable of achieving the effect of preventing, improving and/or treating metabolic diseases such as obesity by selectively inhibiting the transcriptional activity of PPAR gamma, and has a remarkable pharmaceutical value especially for obesity patients suffering from fatty liver.
Description
Technical field
The present invention relates to a kind of Protopanaxatriol or/and the medicinal usage of its derivant, belongs to medical art.
Background technology
Fatty liver refers to the pathological changes due to overheap fatty in the hepatocyte that a variety of causes causes.The health of the positive serious threat compatriots of fatty liver disease, become the second largest hepatopathy being only second to viral hepatitis, oneself is acknowledged as the common cause of disguised liver cirrhosis.The lighter is asymptomatic in fatty liver clinical manifestation, and the severe one state of an illness is violent.Generally speaking, fatty liver belongs to reversibility disease, and early diagnosis also treatment in time often can recover normal.
The sickness rate of fatty liver rose rapidly in American-European and China in recent years, and in some professional population, the average attack rate of (white collar personage, taxi driver, professional manager, individual proprietor, government official, high level intellectual etc.) fatty liver is 25%; In obese people and type ii diabetes patient, the sickness rate of fatty liver is 50%; Being addicted to drink with the sickness rate of alcoholic fatty liver is 58%; In often insomnia, tired, the sub-health population of not thinking ordinary food and drink, gastrointestinal dysfunction, the sickness rate of fatty liver is about 60%.The age of fatty liver crowd also constantly declines in recent years, and the mean age only has 40 years old, and the patient of about 30 years old also gets more and more.Within less than 45 years old, fatty liver in male is obviously more than women.
Up to the present; Western medicine there is no lipotropic active drug; usually protection hepatocyte, degrease medicine and antioxidant etc. are selected; as vitamin B, C, E, lecithin, ursodesoxycholic acid, inosine, coenzyme A, reduced glutathion, taurine, carnitine Orotate, glucuronolatone, and some fat-reducing medicament (such as: liver purport is clear) etc.Although said medicine is a lot, effect is not ideal and have potential hepatotoxicity mostly, and action target spot is single, therefore can not obtain satisfied therapeutic effect.Research and develop a kind of effective medicine to fatty liver to be of great practical significance.
Protopanaxatriol is (English by name: Protopanaxatriol, referred to as PPT) be the sapogenin of panaxatriol's saponins, there are 20 (S)-Protopanaxatriols and 20 (R)-Protopanaxatriols, two kinds of configurations, the two is a pair configurational isomer, all belong to dammarane type four-ring triterpenoid class, the dry root of Araliaceae Radix Ginseng Panax ginseng C.A.Mey. can be derived from.The open PPT saponin such as Xiang Qiuling obviously can improve the hemiplegia sign of MCAO rat, reduces infarct size in brain, alleviates cerebral edema [Zhongshan University's journal (medical science version), 2008 (06)]; The open PPT saponin extracted by Radix Panacis Quinquefolii such as Xie Yaqi can stimulate adrenal cortex function and can reduce the little dirty contraction of rest state penetrates blood, reduce myocardial oxygen consumption under kinestate and invigoration effect [Journal of Shenyang Institute of Physical Education to myocardial contraction Ejection function, 2001 (01)], but so far there are no about PPT and derivant thereof have prevention or treatment fatty liver active reporter.
Summary of the invention
The object of this invention is to provide a kind of Protopanaxatriol or/and the new pharmaceutical uses of its derivant, to widen Protopanaxatriol or/and the range of application of its derivant.
A kind of Protopanaxatriol of the present invention, or/and the medicinal usage of its derivant, refers to using Protopanaxatriol or/and its derivant is used for the treatment of the medicine of fatty liver as active fraction preparation.
Described Protopanaxatriol is or/and its derivant comprises at least one in the precursor compound of 20 (S)-Protopanaxatriols, 20 (R)-Protopanaxatriols, the racemic modification of Protopanaxatriol, the pharmaceutically acceptable salt of Protopanaxatriol, the hydrate of Protopanaxatriol and Protopanaxatriol.
Described " pharmaceutically acceptable salt of Protopanaxatriol " refers to that Protopanaxatriol and mineral acid, Organic Acid and Base metal or alkaline-earth metal etc. react the salt generated.These salt are including, but not limited to the salt that (1) and following mineral acid are formed, example hydrochloric acid, hydrobromic acid, hydroiodic acid, sulphuric acid, nitric acid, phosphoric acid; (2) salt formed with following organic acid, as acetic acid, lactic acid, citric acid, succinic acid, Fumaric acid, gluconic acid, benzoic acid, Loprazolam, ethane sulfonic acid, benzenesulfonic acid, p-methyl benzenesulfonic acid, oxalic acid, succinic acid, tartaric acid, maleic acid or arginine.Other salt comprises with alkali metal or alkaline-earth metal (as sodium, potassium, calcium or magnesium) salt that formed, ammonium salt or water miscible amine salt (as N-METHYL-ALPHA-L-GLUCOSAMINE salt), rudimentary alkanol ammonium salt and other pharmaceutically acceptable amine salt (such as methylamine salt, ethylamine salt, propylamine salt, dimethyl amine salt, trismethylamine salt, diethyl amine salt, triethyl amine salt, tert-butylamine salt, ethylenediamine salt, oxyethylamine salt, dihydroxy ethylamine salt, three oxyethylamine salt, and respectively by morpholine, piperazine, the amine salt that lysine is formed), or the form of " prodrug " of other routine.
Because Protopanaxatriol's compound has asymmetric center, have 20 (S) and 20 (R), two kinds of isomers, these isomers can separately or as the form of mixtures of racemic mixture, independent enantiomer, independent diastereomer, diastereomer as active component.
Described " precursor compound " refers to after taking by suitable method, and this precursor compound carries out metabolism in patient body or chemical reaction can be transformed into reactive compound of the present invention, or the salt formed for reactive compound of the present invention or solution.Precursor compound of the present invention is including, but not limited to the form such as carboxylate, carbonic ester, phosphate ester, nitrate, sulfuric ester, sulfone ester, sulfoxide esters, amino-compound, carbaminate, azo-compound, phosphamide, glucoside, ether, acetal of Protopanaxatriol.
Those skilled in the art should be understood that cicada the compounds of this invention structure after, by multiple method well known in the art, utilize known raw material, obtain derivant of the present invention, such as chemosynthesis or extract from plant.
Term as used herein " contain " or " comprising " include " comprising ", " substantially by ... form " and " by ... form ".Term " substantially by ... form " refer in the composition, except containing except main active, also can contain a small amount of and not affect submember and/or the impurity of effective ingredient.Such as, sweeting agent can be contained to improve taste, antioxidant in case oxidation, and the additive that other this area is conventional.
In the present invention, " pharmaceutically acceptable " composition is the material being applicable to people and namely having rational benefit/risk ratio without excessive bad side reaction (as toxicity, stimulation and allergy).
The dosage form of medicine of the present invention can be diversified, as long as the dosage form that active component can be made effectively to arrive in mammalian body is all fine.Such as can be selected from: tablet, capsule, powder, granule, syrup, solution, suspension, injection, tincture, oral liquid, aerosol, suck the slow release formulations such as common dosage forms or nanometer formulation such as agent, electuary, pill, powder.
Effective application dosage of active component of the present invention can change with the order of severity of the pattern of compound used, administration and disease to be treated.But, usually when reactive compound of the present invention gives with the dosage of about 100-500mg/kg the weight of animals every day, gratifying effect can be obtained, preferably give with the dosage that 1-3 time is separated every day, or with sustained release forms administration.Be applicable to the dosage form taken orally, comprise and the solid-state or intimately mixed reactive compound of liquid carrier.This dosage of scalable to provide optimal treatment, such as: by treatment situation an urgent demand, the dosage that several times separate can be given every day, or dosage is reduced pari passu.
Result of study display of the present invention: Protopanaxatriol not only has the in vitro effects significantly suppressing Adipocyte Differentiation, and the C57BL/6 Mouse Weight of high-fat meal induction capable of blocking increases, the volume of body fat cell is suppressed to increase, improve mice fasting glucose, insulin resistant, and effect in the body such as the dyslipidemia of mice; In addition, PPAR γ reporter gene assays result display Protopanaxatriol optionally can suppress the transcriptional activity of PPAR γ.Describe Protopanaxatriol and not only to fatty liver, there is remarkable therapeutic activity, also simultaneously by optionally suppressing the transcriptional activity of PPAR γ to play prevention, improving and/or treat metabolic disease as the effect of obesity, especially can have significance medical value to the obese patient suffering from fatty liver.
Accompanying drawing explanation
Fig. 1 embodies Protopanaxatriol to be affected the body weight of the fat C57BL/6 mice that high lipid food is induced; In figure: * represents and to compare with matched group, P<0.05.
Fig. 2 embodies the impact of Protopanaxatriol on obesity mice adipose cell density.
Fig. 3 A is the liver organization aspect graph of each group of mice observed after adopting HE dyeing.
Fig. 3 B is the liver organization aspect graph of each group of mice observed after adopting oil red dyeing.
Fig. 4 embodies the impact of Protopanaxatriol on content of triglyceride; In figure: * represents and to compare with matched group, P<0.05; * represents and to compare with matched group, P<0.01.
Fig. 5 A embodies the impact of Protopanaxatriol on obesity mice fasting glucose; In figure: * represents and to compare with matched group, P<0.05; * represents and to compare with matched group, P<0.01.
Fig. 5 B embodies the improvement result of Protopanaxatriol to obesity mice glucose tolerance test; In figure: * represents and to compare with matched group, P<0.05; * represents and to compare with matched group, P<0.01.
Fig. 6 embodies the improvement result of Protopanaxatriol to obesity mice Glucose Tolerance Test; In figure: * represents and to compare with matched group, P<0.05.
Fig. 7 A is the testing result of reporter gene; In figure: * represents and to compare with matched group, P<0.05; * represents and to compare with matched group, P<0.01.
Fig. 7 B is Fluorescence Resonance Energy shift experiment result.
Detailed description of the invention
Below in conjunction with specific embodiment, set forth the present invention further.Should be understood that these embodiments are only not used in for illustration of the present invention to limit the scope of the invention.The experimental technique of unreceipted actual conditions in the following example, the usually conveniently conditioned disjunction condition of advising according to manufacturer.Unless otherwise indicated, otherwise percentage ratio and number calculate by weight.
Embodiment
1. medicine and animal
8 week age C57/BJ6 mice, body weight be about 22-25 gram/only.Rearing conditions is SPF level, raising temperature 22-23 DEG C.Within 12 hours, day alternates with night.Animal feed is purchased from Research Diet (high fat D12492, low fat D12450B).
Following embodiment is using 20 (S)-Protopanaxatriol monomeric compounds as active medicine, and its chemical mechanical formula is as follows:
2. experimental apparatus
Blood glucose meter and reagent paper are purchased from Roche (with all strength health).
3. animal and grouping
The forage feed of mice in 8 week age containing 60% (w/w) fat, medicine is mixed into feedstuff by treatment group, mice ad lib, drinking-water.Treat 8 weeks altogether.The next day record Mouse Weight and food ration.
4. Protopanaxatriol is on the impact of obesity mice body weight
C57BJ/6 mice is after high lipid food (Research Diet, D12492) raises 3 months, and obesity mice is through gavage Protopanaxatriol (administration concentration is 0.1wt%), and successive administration 4 weeks, measures a Mouse Weight weekly.
Fig. 1 embodies Protopanaxatriol to be affected the body weight of the fat C57BL/6 mice that high lipid food is induced; * in figure: represent and compare with matched group, P<0.05.As seen from Figure 1: Protopanaxatriol's administration group presents obvious reduction (P<0.05) relative to the body weight of matched group, show that Protopanaxatriol can alleviate the body weight of obesity mice, there is antiobesity action.
5. Protopanaxatriol is on the impact of obesity mice adipose cell density
C57BJ/6 mice is through high lipid food (Research Diet, D12492) raise after 3 months, obesity mice is through gavage Protopanaxatriol (administration concentration is 0.1wt%), successive administration 4 weeks, then the adipose cell density of mice is respectively organized with scanning electron microscope observation, observation pictures as shown in Figure 2, as seen from Figure 2: the adipose cell density through the obesity mice of Protopanaxatriol's treatment presents obvious reduction, show that Protopanaxatriol can reduce the adipose cell of obesity mice, further illustrate it and there is antiobesity action.
6. Protopanaxatriol is to the improvement result of obesity mice fatty liver
C57BJ/6 mice is through high lipid food (Research Diet, D12492) raise after 3 months, obesity mice is through gavage Protopanaxatriol (administration concentration is 0.1wt%), successive administration 4 weeks, carry out liver section, adopt HE dyeing to observe each group of mouse liver tissue morphology respectively and adopt oil red dyeing to observe liver organization fat content, to judge fatty liver degree.
Fig. 3 A is the liver organization aspect graph of each group of mice observed after adopting HE dyeing, from Fig. 3 A: the fat vacuole of obesity mice liver increases, but after Protopanaxatriol's treatment, the fat vacuole of obesity mice liver significantly reduces.
Fig. 3 B is the liver organization aspect graph of each group of mice observed after adopting oil red dyeing, from Fig. 3 B: after Protopanaxatriol's treatment, the fatty quantity of obesity mice liver significantly reduces.
Homogenate is carried out, chloroform to the liver of above-mentioned each group of mice, dissolves after chloroform layer drying with isopropyl alcohol, survey content of triglyceride wherein; Testing result as shown in Figure 4, as seen from Figure 4: through Protopanaxatriol treatment after, the content of triglyceride in obesity mice liver can be made significantly to reduce (P<0.05).
To sum up experimental result is visible: Protopanaxatriol significantly can improve the fatty liver degree of obesity mice.
7. Protopanaxatriol tests the fasting glucose of obesity mice
C57BJ/6 mice is after high lipid food (Research Diet, D12492) raises 3 months, and through gavage Protopanaxatriol (administration concentration is 0.1wt%), successive administration 4 weeks, surveys fasting glucose; Mice administration the morning 9 time, mice overnight fasting before survey blood glucose.Control mice feeding low fat feedstuff (Research Diet, D12450B).
Fig. 5 A embodies the impact of Protopanaxatriol on obesity mice fasting glucose, from Fig. 5 A: the mice fasting glucose through fed with high is significantly higher than low fat control mice.But significantly reduce (P<0.01) through the mice fasting glucose of Protopanaxatriol's feeding after 4 weeks.
8. Protopanaxatriol is to the glucose tolerance test of obesity mice
C57BJ/6 mice is after high lipid food (Research Diet, D12492) raises 3 months, and through gavage Protopanaxatriol (administration concentration is 0.1wt%), successive administration 4 weeks, carries out glucose tolerance test; Survey mice overnight fasting before blood glucose, survey fasting glucose first 2 hours gastric infusions 1 time.Control mice feeding low fat feedstuff (Research Diet, D12450B).
Survey mouse glucose tolerance test: mouse peritoneal injection 1g/kg body weight glucose, 0,15,30,60,90min time survey mouse tail vein blood glucose value.
Fig. 5 B embodies the improvement result of Protopanaxatriol to obesity mice glucose tolerance test, from Fig. 5 B: in the test that two hours carry out upon administration of the obesity mice after Protopanaxatriol's feeding, the blood glucose of mice when 30 and 60min presents obvious decline (P<0.01), shows that Protopanaxatriol can improve the insulin resistant of the obesity mice through high lipid food induction.
9. Protopanaxatriol is to the Glucose Tolerance Test of obesity mice
C57BJ/6 mice is after high lipid food (Research Diet, D12492) raises 3 months, and in feedstuff, add Protopanaxatriol's (administration concentration is 0.1wt%), successive administration 4 weeks, carries out Glucose Tolerance Test; Mice overnight fasting before survey blood glucose.Control mice feeding low fat feedstuff (Research Diet, D12450B).
Survey the sugared resistance test of mouse islets element: mice has three days off, insulin injection 10U/kg body weight, respectively at 0,15,30,60,90min time survey mouse tail vein blood glucose value.
Fig. 6 embodies the improvement result of Protopanaxatriol to obesity mice Glucose Tolerance Test; In figure: * represents and to compare with matched group, P<0.05.As seen from Figure 6: in the test that two hours carry out upon administration of the obesity mice after Protopanaxatriol's feeding, the blood glucose of mice when 30 and 60min presents obvious decline (P<0.05), show that Protopanaxatriol can increase the insulin sensitivity of the obesity mice of high lipid food induction, significantly can improve the insulin resistant of the obesity mice through high lipid food induction.
10. Protopanaxatriol affects the blood lipid level of obesity mice
C57BJ/6 mice after high lipid food (Research Diet, D12492) raises 3 months, through gavage Protopanaxatriol (administration concentration is 0.1wt%), successive administration 4 weeks.Control mice feeding low fat feedstuff (Research Diet, D12450B).
At mice fasting Culling heart blood after 12 hours, leave standstill 2 hours, the centrifugal 15min of 3000rpm, collect mice serum, full automatic biochemical apparatus surveys triglyceride, cholesterol, high density lipoprotein and low-density lipoprotein white level.
Test result is shown in Table 1.
The blood lipid level of mice respectively organized by table 1
*p < 0.05,
*p < 0.01vs. height fat matched group
From table 1 result: the T-CHOL (TC) of high fat group mice, triglyceride (TG), high density lipoprotein (HDL-c) and low density lipoprotein, LDL (LDL-c) level are all higher than low fat control mice.And have certain reduction through the triglyceride of the administration group mice of Protopanaxatriol's feeding after 4 weeks, T-CHOL and low density lipoprotein, LDL.Show: Protopanaxatriol significantly can reduce the serum triglyceride level of obesity mice, T-CHOL, high density lipoprotein and low-density lipoprotein white level are slightly reduced.
The PPAR γ antagonistic activity test of 11. Protopanaxatriols
A, Protopanaxatriol detect the reporter gene of nuclear receptors PPAR's γ
When 293T cell grows to the density of 50%-80%, by pCMXGal-mPPAR γ-LBD, MH100 × 4-TK-Luc plasmid and liposome cotransfection in 293T cell, cultivate the concentration process cell of ligands specific rosiglitazone (10 μ g/mL) and Protopanaxatriol 10,25, the 50 μ g/mL using PPAR γ after 24 hours.After process 24h, wash cell twice with PBS.Every hole adds the lysate of 65 μ L, and the centrifugal 5min of shaking table vibration 15min, 1000rpm, gets supernatant lysate 10 μ L, add LAR II liquid 20 μ L, mixing, survey fluorescence, within 2 seconds, postpones, reads 10 seconds.Renilla fluorescent value is as internal reference, and identical experiment in triplicate, tests three multiple holes, statistical data at every turn.
Detect through reporter gene, Protopanaxatriol can remarkable antagonism PPAR γ transcriptional activity (refer to Fig. 7 A shown).
B, Applicative time resolved fluorescent resonance energy transfer experiments detect the binding ability of Protopanaxatriol and nuclear receptors PPAR's γ
Protopanaxatriol to come indirect reaction Protopanaxatriol and nuclear receptors PPAR's γ binding ability from the ability that acceptor site displaces tagged ligand is detected by Applicative time resolved fluorescent resonance energy transfer experiments.Add the 2X testing compound of 10 μ L variable concentrations gradients, 2X positive reference compound in 384 orifice plates.Add 5 μ L 4XPPAR-LBD/Tb-anti-GST antibody, 5 μ L 4X fluorescent dyes (Fluormone Pan-PPAR Green), lucifuge, jolting 30s gently, 1000r is centrifugal, and incubated at room 1-2h, Envision test the fluorescence signal of 495nm and 520nm.
Experimental result refers to shown in Fig. 7 B, from Fig. 7 B: Protopanaxatriol and PPAR gamma agonist rosiglitazone compete PPAR γ binding site.Illustrate that Protopanaxatriol has PPAR γ antagonistic activity.
Finally be necessary described herein: those skilled in the art can on above-described embodiment basis, carry out active component " 20 (S)-Protopanaxatriol " used at least one alternative embodiment in the precursor compound of the racemic modification of 20 (R)-Protopanaxatriols or Protopanaxatriol, the pharmaceutically acceptable salt of Protopanaxatriol, the hydrate of Protopanaxatriol and Protopanaxatriol and carry out the experiments of above-mentioned activity, will not enumerate at this.
Claims (4)
1. one kind using Protopanaxatriol or/and its derivant is used for the treatment of the medicinal usage of fatty liver as active fraction preparation.
2. medicinal usage as claimed in claim 1, is characterized in that: described active component comprises at least one in the precursor compound of 20 (S)-Protopanaxatriols, 20 (R)-Protopanaxatriols, the racemic modification of Protopanaxatriol, the pharmaceutically acceptable salt of Protopanaxatriol, the hydrate of Protopanaxatriol and Protopanaxatriol.
3. medicinal usage as claimed in claim 2, is characterized in that: the pharmaceutically acceptable salt of described Protopanaxatriol refers to that Protopanaxatriol and mineral acid, Organic Acid and Base metal or alkaline-earth metal react the salt generated.
4. medicinal usage as claimed in claim 1, is characterized in that: using Protopanaxatriol or/and its derivant is as the medicine of sole active agent for the preparation for the treatment of fatty liver.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108314698A (en) * | 2017-01-17 | 2018-07-24 | 刘珂 | Protopanoxadiol sodium phosphate and its preparation and its independent or multiple medicine combine the application in treating nephrotic syndrome |
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| CN1460481A (en) * | 2003-06-11 | 2003-12-10 | 陕西太明药物研究开发有限公司 | Medicine composition using resveratrol glucodside for curing fatty liver and its preparation method |
| CN101549039A (en) * | 2008-04-02 | 2009-10-07 | 潘思源 | Application of schisandra fruit or related monomeric compound thereof for preventing or curing fatty liver |
| CN102665725A (en) * | 2009-12-21 | 2012-09-12 | 狮王株式会社 | Hyperlipemia-ameliorating agent, anemia-ameliorating composition, uric-acid-level-reducing composition, and foods and beverages |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1460481A (en) * | 2003-06-11 | 2003-12-10 | 陕西太明药物研究开发有限公司 | Medicine composition using resveratrol glucodside for curing fatty liver and its preparation method |
| CN101549039A (en) * | 2008-04-02 | 2009-10-07 | 潘思源 | Application of schisandra fruit or related monomeric compound thereof for preventing or curing fatty liver |
| CN102665725A (en) * | 2009-12-21 | 2012-09-12 | 狮王株式会社 | Hyperlipemia-ameliorating agent, anemia-ameliorating composition, uric-acid-level-reducing composition, and foods and beverages |
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| CN108314698A (en) * | 2017-01-17 | 2018-07-24 | 刘珂 | Protopanoxadiol sodium phosphate and its preparation and its independent or multiple medicine combine the application in treating nephrotic syndrome |
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Application publication date: 20150408 |