CN103006634A - Use of hypericum sampsonii hance xanthone compounds in antidepressant drug preparation - Google Patents
Use of hypericum sampsonii hance xanthone compounds in antidepressant drug preparation Download PDFInfo
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- CN103006634A CN103006634A CN2011102809055A CN201110280905A CN103006634A CN 103006634 A CN103006634 A CN 103006634A CN 2011102809055 A CN2011102809055 A CN 2011102809055A CN 201110280905 A CN201110280905 A CN 201110280905A CN 103006634 A CN103006634 A CN 103006634A
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Abstract
The present invention discloses a new medical use of hypericum sampsonii hance xanthone compounds. Pharmacodynamics researches show that xanthone compounds such as 1-hydroxy-7-methoxy xanthone and 1,3,5-trihydroxy xanthone in the hypericum sampsonii hance can significantly shorten immobility times in tail suspension and immobility times in forced swimming of mice, and have good antidepressant activity, such that the xanthone compounds can be used for preparing antidepressant drugs or food. With the present invention, a new source is provided for seeking antidepressant drugs or food.
Description
Technical field
The present invention relates to the new medical use of Herba Hyperici Sampsonii Xanthones ketone compounds, being specifically related to is Herba Hyperici Sampsonii Xanthones ketone compounds 1-hydroxyl-7-methoxyl group Xanthones ketone and the application of 1,3,5-trihydroxy Xanthones ketone in preparation antidepressant drug or food.
Background technology
Whole world mental disease becomes outstanding social problem day by day, and depression (depression) is then listed in first of all kinds of mental sickness, accounts for 47% of mental sickness burden.According to World Health Organization's statistics, the sickness rate of global depression is about 11%, and present global patients with depression reaches 1.2 hundred million, and depression has become the 4th large disease that threatens human health.Expect the year two thousand twenty, depression may become and is only second to the cardiopathic the 2nd large disease, and depression is just becoming serious global problems.Depression is the able-bodied commonly encountered diseases of a kind of harm humans, famous psychologist Martin Sai Liman is called " common cold " in the psychiatry with depression, can have influence on anyone, no matter its status, race, age, or sex, marital status or schooling are how.The foreign statistic data shows, about 13～20% people once had depressed experience in life, lifetime prevalence about 17%, the women can be up to 25%, along with rhythm of life day by day accelerate, compete increasingly sharpen and the shortage in the road that pressure is releived, it is nervous, tired and gloomy to have more people, adds poverty, unemployment, is laid off, family's discord, the factors such as old and wounded or disabled, and the sickness rate of depression can further increase.Relevant statistics according to Chinese Association for Mental Hygiene shows that China's depression rate is about 3%-5%, has had at present 2,600 ten thousand people of surpassing to suffer from depression, and the annual financial burden that brings to China has reached 621.91 hundred million yuan.According to a research report of World Health Organization (WHO), depression has become the main killer of 21 century human health at present, the homicide rate of patients with depression is up to 14%, and about 60% all suffers from depression (Center C in the suicide, Davis M, Detre T, et al.Confronting depression and suicide in physicians:a consensus statement.JAMA.2003,18; 289 (23): 3161-6.).Depression also causes huge economy and commercial loss simultaneously.Statistics show, in north America region and EU countries, depression can cause annual loss (Wang PS up to 1,500 hundred million dollars, Simon G, Kessler RC.The economic burden of depression and the cost-effectiveness of treatment.Int J Methods Psychiatr Res.2003; 12 (1): 22-33.)! Therefore, the research of antidepressant drug also becomes one of the fastest field of development.Although alternative antidepressant drug is more on the market, and postural hypotension is arranged more, arrhythmia, epilepsy, hyposexuality and overdose have the multiple untoward reaction such as lethal.Therefore, challenge that the medicine of seeking the control depression of high-efficiency low-toxicity is still that world medical circle faces and a difficult problem, and be devoted to the developmental research of antidepressants, will have very large Social benefit and economic benefit.
Herba Hyperici Sampsonii Hypericum sampsonii Hance. is Hypericaceae (Hypericaceae) Hypericum (Hypericum Linn.) herbaceos perennial, aboundresources, be distributed widely in each provinces and regions on the south China Yangtze river basin, in Vietnam (the north), Burma (east), India (northeast) and Japan distribution arranged also.Among the people with all herbal medicine, have the effect of cooling blood for hemostasis, heat-clearing and toxic substances removing, promoting blood flow to regulate menstruation, dispelling wind and removing obstruction in the collateral.Cure mainly haematemesis, spitting of blood, epistaxis, stranguria with blood, wound hemorrhage, enteritis, dysentery, acute mastitis, carbuncle furunculosis, scald, venom, menoxenia, dysmenorrhea, leucorrhea, traumatic injury, rheumatic arthralgia and lumbago and skelalgia etc.The chemical constituent of Herba Hyperici Sampsonii mainly contains three classes: phloroglucinol class (phloroglucinol derivatives), naphthalene a pair of horses going side by side dianthracene ketone (naphthodianthrones) and Xanthones ketone (xanthones) (Xin WB, Mao ZJ, Jin GL, Qin LP.Two new xanthones from Hypericum sampsonii and biological activity of the isolated compounds.Phytother Res.2011,25 (4): 536-9.).Modern pharmacological research shows, the Xanthones ketone compounds has multiple biological activity: (Fu's acenaphthenes such as Antimalarial, the effect that protects the liver and treat acute, chronic hepatitis, antioxidation, tuberculosis effect, treatment heat symptom-complex, liver-gallbladder disease and hematopathy, function of resisting myocardial ischemia, Zhang Chuan, Zhang Weidong, Liu Runhui, Xu Xike. the pharmacology activity research progress of xanthone compounds. pharmacy practice magazine .2005,23 (1): 6-12.).Relevant Herba Hyperici Sampsonii Xanthones ketone compounds is used for the report of anti-depression aspect but so far there are no.
Summary of the invention
Technical problem to be solved by this invention provides the application of Herba Hyperici Sampsonii Xanthones ketone compounds in preparation antidepressant drug or food.
Herba Hyperici Sampsonii Xanthones ketone compounds of the present invention refers to 1-hydroxyl-7-methoxyl group Xanthones ketone and 1,3,5-trihydroxy Xanthones ketone, and their chemical structural formula is as follows:
1-hydroxyl-7-methoxyl group Xanthones ketone 1,3,5-trihydroxy Xanthones ketone
The preparation method of above-claimed cpd comprises the steps:
(1) preparation extracting solution: after the Herba Hyperici Sampsonii pulverizing medicinal materials, drop into extraction pot, carry 2～3 times with 40～90% ethanol heat, each solvent consumption is about 8～10 times of crude drug amount, and each extraction time is 1～2 hour, merge extractive liquid;
(2) refining concentrate drying: said extracted liquid is concentrated, and concentrated solution is used ethyl acetate extraction behind defat with petroleum ether, and concentrating under reduced pressure obtains ethyl acetate extract;
(3) separation and purification: with the water-soluble rear loading macroporous adsorbent resin of above-mentioned ethyl acetate extract, respectively with water, 20%, 40%, 60% and 80% ethanol system eluting, wherein 80% eluting partly utilizes the SephadexLH-20 gel column chromatography to carry out purification, 80% methanol-water is elution system, obtains 1-hydroxyl-7-methoxyl group Xanthones ketone; 40% eluting part is in conjunction with the ODS reversed-phase silica gel column chromatography, and methanol-water (1: 2 → 1: 0) solvent system eluting gets 1,3,5-trihydroxy Xanthones ketone.
In the step " (3) separation and purification ": described macroporous resin is to be selected from a kind of among AB-8, D-101, ZTC-1, HPD-100 or the DA201.
Among the embodiment subsequently, Herba Hyperici Sampsonii Xanthones ketone compounds is through testing with mouse tail suspension stress tests and mice forced swimming, find 1-hydroxyl-7-methoxyl group Xanthones ketone and 1,3,5-trihydroxy Xanthones ketone all can significantly shorten mouse tail suspension dead time and mice forced swimming dead time, have good antidepressant activity, therefore can be used for preparing antidepressant drug or food.
The specific embodiment
Below in conjunction with specific embodiment, further set forth the present invention.These embodiment are interpreted as only being used for explanation the present invention and are not used in restriction protection scope of the present invention.After the content of having read the present invention's record, those skilled in the art can make various changes or modifications the present invention, and these equivalences change and modification falls into claim limited range of the present invention equally.
Embodiment 1: the preparation of Xanthones ketone compounds
(1) preparation extracting solution: after the Herba Hyperici Sampsonii pulverizing medicinal materials, drop into extraction pot, carry 2～3 times with 40～90% ethanol heat, each solvent consumption is about 8～10 times of crude drug amount, and each extraction time is 1～2 hour, merge extractive liquid;
(2) refining concentrate drying: said extracted liquid is concentrated, and concentrated solution is used ethyl acetate extraction behind defat with petroleum ether, and concentrating under reduced pressure obtains ethyl acetate extract;
(3) separation and purification: with the water-soluble rear loading macroporous adsorbent resin of above-mentioned ethyl acetate extract, respectively with water, 20%, 40%, 60% and 80% ethanol system eluting, wherein 80% eluting partly utilizes the SephadexLH-20 gel column chromatography to carry out purification, 80% methanol-water is elution system, obtains 1-hydroxyl-7-methoxyl group Xanthones ketone; 40% eluting part is in conjunction with the ODS reversed-phase silica gel column chromatography, and methanol-water (1: 2 → 1: 0) solvent system eluting gets 1,3,5-trihydroxy Xanthones ketone.
The Xanthones ketone compounds that present embodiment makes
13The C-NMR data are as shown in table 1.
The Wave Spectrum data of the Xanthones ketone compounds that present embodiment makes are as follows:
1-hydroxyl-7-methoxyl group: foresythia acicular crystal (CHCl
3-CH
3OH); Mp:129～131 ℃; EI-MS m/z (%): 242[M
+] (100), 227 (29.6), 212 (10.7), 199 (4.2), 171 (12.0), 121 (10.5), 107 (10.0), 89 (4.6), 73 (22.1), 63 (20.6), 55 (11.1); IR (KBr) cm
-1: 3437,1645,1607,1488,1470,1371,1275,1233,1148,1047,1030,811,770,755,716;
1H-NMR (CDCl
3, 400MHz) δ ppm:12.6 (1H, s ,-OH), (7.592 1H, d, J=2.8Hz), 7.31 (1H, dd, J=9.2Hz, J=2.8Hz), 7.54 (1H, t, J=8.4Hz), 6.88 (1H, d, J=8.4Hz), 6.76 (1H, d, J=8.4Hz), (7.37 1H, d, J=9.2Hz);
1,3,5-trihydroxy Xanthones ketone: yellow acicular crystal (CHCl
3-CH
3OH); 226-228 ℃; EI-MS m/z (%): 244[M
+] (100); IR (KBr) cm
-1: 3566,3504,3150,1652,1612,1575,1495,1381,1352,1167,890,845;
1H-NMR (DMSO-d6,400MHz) δ ppm:12.87 (1H, s ,-OH), 11.00,10.35 (OH * 2), 7.55 (1H, dd, J=7.6Hz, J=1.2Hz), 7.25 (1H, t, J=7.6Hz), 7.31 (1H, dd, J=7.6Hz, J=1.2Hz), 6.42 (1H, d, J=2.0Hz), (6.21 1H, d, J=2Hz);
Table 1. Xanthones ketone compounds
13C-NMR data (400MHz)
The 1-hydroxyl that present embodiment makes-7-methoxyl group Xanthones ketone and 1,3,5-trihydroxy Xanthones ketone are used for embodiment 2 and embodiment 3 according to usual method compounding pharmaceutical high dose group (60mg/kgd) and the medicine low dose group (15mg/kgd) of solution allocation.
Embodiment 2: the Xanthones ketone compounds is on the impact of outstanding tail depression model mice dead time
Tail suspension test (Xu Shuyun, Bian Rulian, old repairing. pharmacological experimental methodology, the 3rd edition [M]. Beijing: the People's Health Publisher, 2002:807): ICR mice, male and female half and half, 6～8 ages in week, body weight 20 ± 2g, Second Military Medical University, PLA's Experimental Animal Center provides.18-22 ℃ of receptacle temperature, relative humidity 60%-75%, artificial mixed fodder is fed.Random packet: blank group, positive controls (imipramine 20mg/kgd), medicine high dose group (60mg/kgd) and medicine low dose group (15mg/kgd), every group of 10 mices, successive administration 7 days, the experimental session animal freely takes food and drinks water.Behind the last administration 1h, mouse tail is fixed with clip apart from the about 1cm of end place, it is hung upside down on the cross bar about the 15cm of distance ground, animal is for overcoming undesired position struggle activity, but after asking in the time of movable one section, it is motionless discontinuity to occur, shows disappointed state, and accumulative total is respectively organized the dead time in the 6min.The results are shown in Table 2.
By as seen from Table 2,2 Xanthones ketone compounds all can significantly shorten the mouse tail suspension dead time, with the blank group significant difference (P＜0.05) are arranged more all, and are certain dose-dependence.
Table 2. Xanthones ketone compounds is on the impact (mean ± SD, n=10) of Tail suspension test dead time
Compare * P＜0.05, * * P＜0.01 with the blank group
Embodiment 3: the Xanthones ketone compounds is on the impact of mice forced swimming dead time
Force mouse swimming test (Xu Shuyun, Bian Rulian, old repairing. pharmacological experimental methodology, the 3rd edition [M]. Beijing: the People's Health Publisher, 2002:807): ICR mice, male and female half and half, 6～8 ages in week, body weight 20 ± 2g, Second Military Medical University, PLA's Experimental Animal Center provides.18-22 ℃ of receptacle temperature, relative humidity 60%-75%, artificial mixed fodder is fed.Random packet: blank group, positive controls (imipramine 20mg/kgd), medicine high dose group (60mg/kgd) and medicine low dose group (15mg/kgd), every group of 10 mices, successive administration 7 days, the experimental session animal freely takes food and drinks water.Behind the last administration 1h, mice is put in diameter 14cm, depth of water 15cm, in the container that water temperature is 25 ℃, measure the floating motionless time of mice within the 6min (be that mice stops to struggle, or animal is floating state, tiny limb motion only arranged to keep head to keep afloat) in water.The results are shown in Table 3.
By as seen from Table 3,2 Xanthones ketone compounds all can significantly shorten the mice forced swimming dead time, with the blank group significant difference (P＜0.05) are arranged more all, and are certain dose-dependence.
Table 3. Xanthones ketone compounds is on the impact (mean ± SD, n=10) of experiment dead time of mice forced swimming
Compare * P＜0.05, * * P＜0.01 with the blank group
The experimental result of present embodiment shows, Xanthones ketone compounds 1-hydroxyl-7-methoxyl group Xanthones ketone and 1,3, the high low dose group of 5-trihydroxy Xanthones ketone all can significantly shorten mouse tail suspension dead time and mice forced swimming dead time, have good antidepressant activity, therefore can be used for preparing antidepressant drug or food.
Claims (4)
1. the purposes of Herba Hyperici Sampsonii Xanthones ketone compounds in preparation antidepressant drug or food.
2. purposes according to claim 1 is characterized in that, Herba Hyperici Sampsonii Xanthones ketone compounds is 1-hydroxyl-7-methoxyl group Xanthones ketone.
3. purposes according to claim 1 is characterized in that, Herba Hyperici Sampsonii Xanthones ketone compounds is 1,3,5-trihydroxy Xanthones ketone.
4. purposes according to claim 1 is characterized in that, Herba Hyperici Sampsonii Xanthones ketone compounds is 1-hydroxyl-7-methoxyl group Xanthones ketone and 1,3,5-trihydroxy Xanthones ketone.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104177324A (en) * | 2013-05-20 | 2014-12-03 | 南京工业大学 | Xanthone compounds and their use in depression resistance |
| CN105434422A (en) * | 2014-08-12 | 2016-03-30 | 天津药物研究院 | Application of alpha and gamma-mangostin in preparation of antidepressant drug |
| CN105560303A (en) * | 2014-10-15 | 2016-05-11 | 中国人民解放军第二军医大学 | Application of hypericum sampsonii hance total xanthone in preparation of antidepressant drugs |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08119959A (en) * | 1994-10-20 | 1996-05-14 | Oyo Seikagaku Kenkyusho | Xhanthone derivative and inhibitor of monoamine oxidase containing the same as active ingredient |
| CN1239547A (en) * | 1996-04-15 | 1999-12-22 | 法玛普林特公司 | Pharmaceutical grade botanical drugs |
-
2011
- 2011-09-21 CN CN2011102809055A patent/CN103006634A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08119959A (en) * | 1994-10-20 | 1996-05-14 | Oyo Seikagaku Kenkyusho | Xhanthone derivative and inhibitor of monoamine oxidase containing the same as active ingredient |
| CN1239547A (en) * | 1996-04-15 | 1999-12-22 | 法玛普林特公司 | Pharmaceutical grade botanical drugs |
Non-Patent Citations (4)
| Title |
|---|
| 《J Sci Food Agric》 20101027 Sara L Crockett， et al Bioactive xanthones from the roots of Hypericum perforatum (common St John's wort) 428-434 2-4 第91卷, 第3期 * |
| H.-M. THIEDE ， A. WALPER: "Inhibition of MAO and COMT by Hypericum Extracts and Hypericin", 《JOURNAL OF GERIATRIC PSYCHIATRY AND NEUROLOGY》, vol. 7, no. 1, 31 October 1994 (1994-10-31), pages 54 - 56 * |
| SARA L CROCKETT， ET AL: "Bioactive xanthones from the roots of Hypericum perforatum (common St John’s wort)", 《J SCI FOOD AGRIC》, vol. 91, no. 3, 27 October 2010 (2010-10-27), pages 428 - 434 * |
| 郭澄，等: "元宝草 酮成分的研究", 《中国药学杂志》, vol. 42, no. 6, 31 March 2007 (2007-03-31) * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104177324A (en) * | 2013-05-20 | 2014-12-03 | 南京工业大学 | Xanthone compounds and their use in depression resistance |
| CN104177324B (en) * | 2013-05-20 | 2016-05-11 | 南京工业大学 | Xanthone compounds and antidepression purposes thereof |
| CN105434422A (en) * | 2014-08-12 | 2016-03-30 | 天津药物研究院 | Application of alpha and gamma-mangostin in preparation of antidepressant drug |
| CN105560303A (en) * | 2014-10-15 | 2016-05-11 | 中国人民解放军第二军医大学 | Application of hypericum sampsonii hance total xanthone in preparation of antidepressant drugs |
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Application publication date: 20130403 |