CN103505467A - Applications of stilbene compounds for preparing medicament for preventing and treating depression - Google Patents
Applications of stilbene compounds for preparing medicament for preventing and treating depression Download PDFInfo
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Abstract
The invention discloses applications of a stilbene compounds for preparing medicaments for preventing and treating depression, wherein the stilbene compounds can be used as an effective active component to prepare the medicaments for preventing and treating depression. The stilbene compounds are mixtures containing ore or both of piceatannol or piceatannol 3'-O-beta-D-glucopyranoside, and used in the medicaments for preventing and treating endogenous depression, and/or reactive depression, and/or masked depression, and/or depression using learning difficulty as a characteristic; and/or secondary depression caused by medicaments, and/or secondary depression caused by body diseases, and/or postnatal depression, and/or involutional melancholia, and/or depressive neurosis. By a Konmin mouse tail suspension test, a swimming force test and a chronic stress sucrose preference determination experiment, the stilbene compounds can substantially raises disappointed time of mouse tail suspension and motionless time of forced swimming, has substantial resistant effect for interest deprivation symptom caused by chronic stress, and has a substantial antidepressant effect.
Description
Technical field
The invention belongs to pharmaceutical chemistry technical field, be specifically related to the new purposes of a kind of stilbenes compound in preparation prevention and Cure of depression medicine.
Background technology
Depression is a kind of common mood disorders, can be caused by a variety of causes, and the remarkable and lasting mental state of take is low is main clinical characteristics, and mental state is low unbecoming with its situation, and suicidal thought and behavior can appear in severe patient.According to World Health Organization's statistics, depression has become the large illness in the world the 4th, expects the year two thousand twenty, may become the world's second largest disease that is only second to coronary heart disease, accounts for 15% of global disease burden.According to expert statistics, China's patients with depression accounts for 4～8% of total population, and the number of committing suiside because of trouble depression reaches more than 80 ten thousand people.
The antidepressant of current clinical use comprises: 1, SSRIs(selectivity 5-HT reuptake inhibitor) class medicine, as paroxetine, Sertraline, fluoxetine etc., this class medicine often with feeling sick, vomiting, anorexia, constipation, diarrhoea, xerostomia, tremble, the generation of the untoward reaction such as insomnia, anxiety and sexual dysfunction; 2, TCAs(tricyclic antidepressants) class medicine, as reach body youth; SNRIs(NE and 5-HT reuptake inhibitor) class medicine, the untoward reaction such as venlafaxine, duloxetine etc., this class medicine is common nauseating, xerostomia, perspiration, weak, anxiety, tremble, sexual impotence and defective ejaculation; 3, NaSSAs class (NE and specificity 5-HT can antidepressants), as mirtazapine, this class medicine is common the untoward reaction such as calmness, drowsiness, dizziness, tired, appetite and body weight increase; 4, other medicines are as the weak inhibitor of amfebutamone, norepinephrine, 5-hydroxy tryptamine, dopamine reuptake, commonly have excitement, xerostomia, insomnia, headache or migraine, feel sick, vomiting, constipation, tremble, the untoward reaction such as hyperhidrosis.
Chinese patent (application number 03147932.4) " the oligomeric stilbenes compound of resveratrol and method for making thereof and its pharmaceutical composition and purposes ", discloses the purposes of the medicine of the oligomeric stilbenes compound treatment of resveratrol rheumatoid arthritis, asthma, allergic inflammation; List of references " design of ligustrazine stilbenoids derivatives, synthetic and bioactivity research " (Deng Lijuan, Shandong University, 2007, Master's thesis) discloses ligustrazine stilbenoids derivatives and has had good cardiovascular and cerebrovascular vessel pharmacology activity; List of references " progress of stilbene compound in vitis spp " (Yang Xing magnitude, " gardening collected works 5 ", 2010) disclose stilbene compound in vitis spp and there is the biological activitys such as antioxidation, antitumor, anti-inflammation, angiocardiopathy preventing.
Quzhazhigan, chemistry (E)-1-(3 by name, 5-dihydroxyphenyl)-2-(3-hydroxyl-4-O-β-D-Glucopyranose. phenyl) ethylene or 3,5,3', 4'-tetrahydroxy Stilbene-3'-O-beta-glucosidase, because its plant origin is Lhasa rhubarb rhizome, Lhasa rhubarb has another name called bent letter (" newly repairing Jingzhubencao " in Tibetan medicine, Luo Dashang chief editor, Sichuan science tech publishing house, 2004), therefore claim that this compound is Quzhazhigan.Chinese patent (application number: 201010116358.2) " Quzhazhigan application in the basic preparation of preparation control cardiac-cerebral ischemia and preparation method thereof "; Chinese patent (application number: 2011110371198.0) " a kind of efficient liquid-phase chromatography method of measuring Quzhazhigan content in Lhasa rhubarb "; Chinese patent (application number: 201110253242.8) " a kind of method of preparing piceatannol " discloses extraction process, the detection method of Quzhazhigan and prepared the method for the aglycon piceatannol of Quzhazhigan.Although prior art shows stilbenes compound and has many-sided active application such as antiinflammatory, anti-HIV, antioxidation, anticancer and treatment cardiovascular and cerebrovascular disease, but have no the purposes report in treatment and prevention of depression medicine, more have no Quzhazhigan, the piceatannol purposes report in preparation treatment and prevention of depression medicine.
Along with people are to the understanding of the antidepressant drug side effect of current use and the theory of " back to nature " and the enhancing of consciousness, people pay close attention to from natural plants and find, research and develop antidepressant ideal medicament more.Although also developed successively in recent years the purposes in Cure of depression medicine such as helexin and derivant thereof, naringin, 7-O-β-D-acetylation sugar-coumarin, physcione, but still had the deficiency of the aspects such as clinical therapeutic efficacy is not obvious, side effect large, the difficult control of addiction.If can from Chinese conventional medicament, search out a kind of efficient, have no side effect or low toxic and side effects, can or not be difficult for the compound of addiction, can show the glamour of chinese tradition medical science, for depression doctors and patients open up new treatment approach.
Summary of the invention
The object of the present invention is to provide a kind of have safety, the new purposes of the obvious stilbenes compound of therapeutic effect in preparing Cure of depression medicine.
The purposes of stilbenes compound of the present invention in preparation prevention and Cure of depression medicine, described stilbenes compound general structure is:
Wherein, R is " OH " group or " O-Glu " group.
Prior art field is not also having the disclosing of purposes technology of stilbenes compound aspect prevention and Cure of depression.The new purposes of stilbenes compound of the present invention in preparing Cure of depression medicine, through tail suspension test, forced swimming and chronic stress sucrose partially degree of having a liking for determination experiment show to there is significant antidepressant effect; Through chmice acute and long term toxicity test, within the scope of safe dose, do not observe toxicity reflection.
The specific embodiment
Below the present invention is further illustrated, but never in any form the present invention is limited, any conversion of doing based on training centre of the present invention, all falls into protection scope of the present invention.
The purposes of stilbenes compound of the present invention in preparation prevention and Cure of depression medicine, described stilbenes compound general structure is:
Wherein, R is " OH " group or " O-Glu " group.
The structural formula of stilbenes compound of the present invention " OH " group compound is:
The structural formula of stilbenes compound of the present invention " O-Glu " group compound is:
As preferred implementation: described stilbenes compound is one or both the mixture in Quzhazhigan (compound that structural formula is " O-Glu " group) or piceatannol (compound that structural formula is " OH " group).
As preferred implementation: described Cure of depression medicine at prevention and treatment endogenous depression or/and reactive depression or/and masked depression or/and take depression that learning difficulty is feature or/and the purposes in drug-induced secondary depression medicine.
As preferred implementation: the secondary depression that described Cure of depression medicine causes at prevention and treatment physical disease or/and postpartum depression or/and involutional melancholia or/and the purposes in depressive neurosis medicine.
As preferred implementation: described Cure of depression medicine is to comprise stilbenes compound and the preparation that pharmaceutically one or more auxiliary agents of acceptable form.
As preferred implementation: described Cure of depression pharmaceutical dosage form is tablet, capsule, solution, suspension, injection, drip liquid or freeze-dried powder.
As preferred implementation: the purposes of described stilbenes compound in the mammal depression medicines such as preparation prevention and treatment people, monkey, chimpanzee, baboon, cattle, horse, pig, sheep, dog, rabbit, rat, mice.
As common preferred implementation: described stilbenes compound is 10～200mg/d at the using dosage of human body.
Experimental example 1: toxicity test
1, material
1.1 medicines: Quzhazhigan and piceatannol are prepared by Kunming Medicine Group Stock Co., Ltd, purity is all greater than 98.0% after testing, deposits in exsiccator.
1.2 animals: healthy Kunming mouse, male and female dual-purpose, body weight 18～22g，You Kunming Medicine Group Stock Co., Ltd provide, credit number: SCXK(Yunnan) 2009-0001.
, chmice acute toxicity test
Under maximum administration concentration and maximum administration capacity, mice oral administration gavage gives 1:1 Quzhazhigan and piceatannol mixed powder 5g/kg, Continuous Observation 14d, and experiment mice has no dead and undue toxicity's reaction.The maximum tolerated dose that shows Quzhazhigan and piceatannol mouse stomach is 5g/kg.
, mice long term toxicity test
The 1:1 mixed powder of Quzhazhigan and piceatannol is divided into tri-groups of 50mg/kg, 100mg/kg, 200mg/kg, and drug withdrawal after mice continuous oral gavage 90d is recovered to 28d long term toxicity test.Result shows:
3.1 ordinary circumstances: in administration with between convalescent period, mice fur is smooth, and behavioral activity is normal, body weight increases, and the drinking-water of ingesting is normal;
3.2 hematologys and blood parameters: administration finish with convalescent period after, mouse blood is learned and blood parameters all fluctuates within normal range, shows no obvious abnormalities;
3.3 bone marrow and routine urinalysis index: administration finish with convalescent period after, mouse bone marrow cells and routine urinalysis index show no obvious abnormalities;
3.4 histopathology indexs: administration finish with convalescent period after, Organs of Mice naked eyes show no obvious abnormalities, each internal organs pathology shows no obvious abnormalities change.
Mice long term toxicity test shows, Quzhazhigan and piceatannol have no overt toxicity reaction to mice long term administration.
4, conclusion: chmice acute and long term toxicity test show, Quzhazhigan and piceatannol, within the scope of safe administration, do not have overt toxicity reaction.
experimental example 2: Tail suspension test
1, medicine: Quzhazhigan and piceatannol are prepared by Kunming Medicine Group Stock Co., Ltd, purity is all greater than 98.0% after testing, deposits in exsiccator.During experiment, with 0.9% normal saline, be made into suspension standby.Fluoxetine (fluoxetine Hydrochloride), Lilly Suzhou pharmaceutical Co. Ltd.
2, animal: healthy Kunming mouse, male and female dual-purpose, body weight 18～22 g ，You Kunming Medicine Group Stock Co., Ltd provide, credit number: SCXK(Yunnan) 2009-0001.
3, method: healthy Kunming mouse is divided into 8 groups at random, and every group of l0 only, is respectively blank group (normal saline); Positive controls (fluoxetine Hydrochloride 20.0mg/kg); The high, medium and low dosage group of Quzhazhigan and piceatannol (30.0,20.0,10.0 mg/kg).Gastric infusion, 1 time/d, continuous 7 d.Experimental session animal freely takes food and drinks water.After last administration 1h, mouse tail is fixed with clip apart from the about 1cm of end place, make on its cross bar that hangs upside down 15 cm left and right, Yu Ju ground, animal is for overcoming undesired position struggle activity, but after asking in the time of movable one section, occur that discontinuity is motionless, show disappointed state, hang 6min, the dead time after each group of accumulative total in 4 min.Experimental result is in Table 1.
Table 1, on the impact of mouse tail suspension dead time (n=10,
± S)
| Group | Dosage (mg/Kg) | The outstanding tail dead time (S) |
| Blank group | / | 133.3±18.4 |
| Fluoxetine Hydrochloride group | 20 | 77.6±16.3** |
| Quzhazhigan low dose group | 10 | 109.5±11.4* |
| Dosage group in Quzhazhigan | 20 | 94.7±18.2* |
| Quzhazhigan high dose group | 30 | 83.2±20.1** |
| Piceatannol low dose group | 10 | 103.3±17.8* |
| Dosage group in piceatannol | 20 | 91.5±15.6* |
| Piceatannol high dose group | 30 | 80.1±19.4** |
4, conclusion: Quzhazhigan and piceatannol significantly shorten the mouse tail suspension dead time (* P < 0.05 or * * P < 0.01) under 10mg/Kg, 20mg/Kg, 30mg/Kg dosage, and are dose-dependence.Positive control drug fluoxetine Hydrochloride 20.0 mg/Kg also show same purpose (P < 0.01).Experiment shows, Quzhazhigan and piceatannol can significantly improve the disappointed time of tail suspension test,<b TranNum="157">there is antidepressant effect.</b>
experimental example 3: force mouse swimming test
1, medicine: with experimental example 2.
2, animal: with experimental example 2.
3, method: healthy Kunming mouse is divided into 8 groups at random, and every group of l0 only, is respectively blank group (normal saline); Positive controls (fluoxetine Hydrochloride 20.0mg/kg); The high, medium and low dosage group of Quzhazhigan and piceatannol (30.0,20.0,10.0 mg/kg).Gastric infusion, 1 time/d, continuous 7d.Experimental session animal freely takes food and drinks water.After last administration 1h, mice is put in to diameter 18cm, depth of water 18cm, in the container that water temperature is 25 ℃, mice swimming time is 6min, measure the floating motionless time of mice within 4 min (be that mice stops struggling in water, or animal is floating state, only has tiny limb motion to keep head to keep afloat).Experimental result is in Table 2.
Table 2, on the impact of mice forced swimming dead time (n=10,
± S)
| Group | Dosage (mg/Kg) | The forced swimming dead time (S) |
| Blank group | / | 116.5±14.4 |
| Fluoxetine Hydrochloride group | 20 | 62.6±12.1** |
| Quzhazhigan low dose group | 10 | 97.4±17.9* |
| Dosage group in Quzhazhigan | 20 | 91.9±14.6* |
| Quzhazhigan high dose group | 30 | 79.4±19.2** |
| Piceatannol low dose group | 10 | 93.1±17.3* |
| Dosage group in piceatannol | 20 | 86.9±13.5* |
| Piceatannol high dose group | 30 | 75.4±15.4** |
4, conclusion: mice occurs that in forced swimming model floating motionless state has reflected the desperate behavior of animal, Quzhazhigan and piceatannol obviously shorten the mice forced swimming dead time (* P < 0.05 and * * P < 0.01) under 10mg/Kg, 20mg/Kg, 30mg/Kg dosage, and are dose-dependence.Positive control drug fluoxetine Hydrochloride 20.0 mg/Kg also show same purpose (P < 0.01).Experiment shows, Quzhazhigan and piceatannol can significantly improve the dead time of mice forced swimming,<b TranNum="210">there is antidepressant effect</b>.
experimental example 4: chronic stress mice sucrose is degree of having a liking for determination experiment partially
1, medicine: with experimental example 2.
2, animal: with experimental example 2.
3, method:
The preparation of 3.1 chronic stress models: the continuous 28d of experiment mice is by the intensity of every day 1 or 2 kind of stimulation, and alternately giving mice stimulates below: fasting 24h, prohibit water 24h, restriction and ingest that 2h, pairing raise 12h, the 45 ° of 2h of cage that incline, the 12h that throws light on all night, moist (200ml water is added in 100g bedding and padding) 12h, white noise (110dB) 1h, forced swimming (4 ℃ of the water temperatures) 5min of raising.
3.2 experimental techniques: healthy Kunming mouse is divided into 9 groups at random, 10 every group, is respectively blank group (not carrying out the preparation of Stress model, normal saline), pathological model group (normal saline); Positive controls (fluoxetine Hydrochloride 20.0mg/kg); The high, medium and low dosage group of Quzhazhigan and piceatannol (30.0,20.0,10.0 mg/kg).Gastric infusion in chronic stress model preparation process, 1 time/d.
Each organizes mice fasting, only gives 1% sucrose water 48h and learns sucrose water and partially have a liking for training.After training finishes, mice freely takes food and the 3d that drinks water, then fasting prohibits water 23h, then allows mice freely select to drink 1% sucrose water and tap water, carries out amount of drinking water (g) measurement, by degree of the having a liking for calculating partially of formula calculating sucrose after drinking-water 1h.Mice adapts to 7d, by sucrose partially degree of having a liking for 80 mice equilibriums are divided into 8 groups, through chronic stress, stimulate 28d, again measure mice sucrose water degree of having a liking for partially, calculate sucrose degree of having a liking for rate of change partially simultaneously.Experimental result is in Table 3.
Sucrose is degree of having a liking for=sucrose diseases caused by retention of fluid consumption/(sucrose diseases caused by retention of fluid consumption+drinking purpose of tap water amount) * 100% partially
Sucrose partially degree of having a liking for rate of change=(after chronic stress sucrose water partially sucrose water degree of having a liking for partially before degree of having a liking for-chronic stress)/stress before sucrose water degree of having a liking for * 100% partially
Table 3, chronic stress model mice are to sucrose degree of having a liking for rate of change (n=10) partially
| Group | Dosage (mg/Kg) | Sucrose is degree of having a liking for rate of change (%) partially |
| Blank group | / | 1.4±0.6** |
| Pathological model group | / | -13.1±3.8 |
| Fluoxetine Hydrochloride group | 20 | 4.7±1.9** |
| Quzhazhigan low dose group | 10 | -1.8±0.6* |
| Dosage group in Quzhazhigan | 20 | 2.3±1.7** |
| Quzhazhigan high dose group | 30 | 4.4±1.3** |
| Piceatannol low dose group | 10 | -1.5±0.8* |
| Dosage group in piceatannol | 20 | 1.9±1.1** |
| Piceatannol high dose group | 30 | 4.2±2.0** |
4, conclusion: pathological model group and blank group relatively exist significant difference (P < 0.01), shows under the intervention that there is no medicine, mice, under chronic stress state, causes the hebetude to original foundation.Quzhazhigan and piceatannol are compared with pathology matched group under 10mg/Kg, 20mg/Kg, 30mg/Kg dosage, have statistically significant difference or significant difference (* P < 0.05 and * * P < 0.01), and are dose-dependence.Positive control drug fluoxetine Hydrochloride 20.0 mg/Kg also show and have significant difference (P < 0.01).Experiment shows, Quzhazhigan and piceatannol, show because the hebetude symptom that chronic stress causes has significant resistant function mice<b TranNum="271">there is opposing</b>the hebetude that causes due to depression is relevant<b TranNum="272">the pharmacologically active of brain malfunction</b>.
Comprehensive above-mentioned experiment 2 and 3 results, in conjunction with different animals dose,equivalent conversion factor and method, mice is only calculated by average weight 20g/, people calculates by average weight 70Kg/ people, the dose,equivalent conversion factor K of mice and human body is 388(Xu tertiary Yun,Bian Ru Lian etc., pharmacological experimental methodology [third edition], 202～203 pages), effective dosage of comprehensively extrapolating human body is about 10mg～200mg.
Claims (8)
1. the purposes of stilbenes compound in preparation prevention and Cure of depression medicine, is characterized in that: described stilbenes compound general structure is:
Wherein, R is " OH " group or " O-Glu " group.
2. the purposes of stilbenes compound according to claim 1 in preparation prevention and Cure of depression medicine, is characterized in that: described stilbenes compound is one or both the mixture in Quzhazhigan or piceatannol.
3. the purposes of stilbenes compound according to claim 1 in preparation prevention and Cure of depression medicine, is characterized in that: described Cure of depression medicine prevention and treat endogenous depression or/and reactive depression or/and masked depression or/and take depression that learning difficulty is feature or/and the purposes in drug-induced secondary depression medicine.
4. the purposes of stilbenes compound according to claim 1 in preparation prevention and Cure of depression medicine, is characterized in that: described Cure of depression medicine in prevention and treat secondary depression that physical disease causes or/and postpartum depression or/and involutional melancholia or/and the purposes in depressive neurosis medicine.
5. the purposes of stilbenes compound according to claim 1 in preparation prevention and Cure of depression medicine, is characterized in that: described Cure of depression medicine is to comprise stilbenes compound and the preparation that pharmaceutically one or more auxiliary agents of acceptable form.
6. the purposes of stilbenes compound according to claim 5 in preparation prevention and Cure of depression medicine, is characterized in that: described Cure of depression pharmaceutical dosage form is tablet, capsule, solution, suspension, injection, drip liquid or freeze-dried powder.
7. the purposes of stilbenes compound according to claim 1 in preparation prevention and Cure of depression medicine, is characterized in that: described stilbenes compound is in preparation prevention and treat the purposes in the mammal depression medicines such as people, monkey, chimpanzee, baboon, cattle, horse, pig, sheep, dog, rabbit, rat, mice.
8. the purposes in preparation prevention and Cure of depression medicine according to the arbitrary described stilbenes compound of claim 1～5, is characterized in that: described stilbenes compound is 10～200mg/d at the using dosage of human body.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109288852A (en) * | 2018-11-20 | 2019-02-01 | 昆药集团股份有限公司 | The purposes of Quzhazhigan or derivatives thereof |
| CN109718332A (en) * | 2019-01-11 | 2019-05-07 | 浙江医药高等专科学校 | The preparation method and its usage of total stilbene compound in bletilla fibrous root |
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| CN101787061A (en) * | 2010-03-02 | 2010-07-28 | 昆明翔昊科技有限公司 | Application of Quzhazhigan in preparation of preparations for preventing and treating cardiac-cerebral ischemia diseases, and preparation method thereof |
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| US20090042817A1 (en) * | 2005-02-04 | 2009-02-12 | Peter Heger | Use of an Active Ingredient Combination That Contains Hydroxystilbene for Preventing and/or Treating Diseases |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109288852A (en) * | 2018-11-20 | 2019-02-01 | 昆药集团股份有限公司 | The purposes of Quzhazhigan or derivatives thereof |
| CN109718332A (en) * | 2019-01-11 | 2019-05-07 | 浙江医药高等专科学校 | The preparation method and its usage of total stilbene compound in bletilla fibrous root |
| CN109718332B (en) * | 2019-01-11 | 2021-05-04 | 浙江医药高等专科学校 | Preparation method and pharmaceutical application of total stilbene compounds in bletilla striata fibrous roots with antidepressant effect |
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Address after: 650106 Kunming science and Technology Industrial Development Zone, Yunnan Province Road No. 166 Patentee after: Kun Yao Group Plc Address before: 650106 Kunming science and Technology Industrial Development Zone, Yunnan Province Road No. 166 Patentee before: Kunming Pharmaceutical Industry Group Corp., Ltd. |