CN100441191C - Use of steroidal compound and total steroidal extract for preparing anti-depression drug - Google Patents
Use of steroidal compound and total steroidal extract for preparing anti-depression drug Download PDFInfo
- Publication number
- CN100441191C CN100441191C CNB200510111265XA CN200510111265A CN100441191C CN 100441191 C CN100441191 C CN 100441191C CN B200510111265X A CNB200510111265X A CN B200510111265XA CN 200510111265 A CN200510111265 A CN 200510111265A CN 100441191 C CN100441191 C CN 100441191C
- Authority
- CN
- China
- Prior art keywords
- total
- sterol
- extract
- cupreol
- phytosterin compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Landscapes
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention discloses a sterol compound and total sterol extract, and their application in preparation of medicine for resisting depression. The described sterol compound mainly includes sitosterol, stigmasterol, campesterol, brassicasterol, steroid glycoside, sterol ester and acylated steroid glycoside, etc. The animal tests show that the above-mentioned compounds have action of resisting depression for mouse.
Description
Technical field:
The invention belongs to the Natural Medicine Chemistry technical field.Be specifically related to the application in the preparation antidepressant drug of phytosterin compound and total-sterol extract.
Background technology:
Phytosterin compound in the phytosterin compound, particularly plant mainly comprises sitosterol, stigmasterol, campesterol, brassicasterol and steroline, sterol ester and acidylate steroline etc.All contain phytosterin compound in a lot of plants, in plant, mainly exist with form of mixtures.
The biological activity of relevant phytosterin compound also has a large amount of reports.For example, steroline has complement activation and anti-inflammatory activity; The steroline mixture that comprises cupreol glucoside and other cupreol glucosides has immunoregulation effect; In vivo test shows that they have effect to HashimotoShi thyroiditis, atopic exzema, psoriasis, asthma and tumor.But sterol cholesterol reducing.But the sterols composition does not appear in the newspapers to central nervous system's such as depression, anxiety effect.
Depression (depression) is the main type of affective disorders (mood disorders), be a kind of low with remarkable and persistent mental state be the syndrome of principal character, its mainly show be in a bad mood low, speech reduces, spirit, bradykinesia, normal self-accusation crime certainly, even suicide attempts etc.Along with socioeconomic fast development, rhythm of life is accelerated day by day, and life and work pressure continues to increase, and depression has become the commonly encountered diseases of modern society, high morbidity, and its sickness rate is soaring rapidly.According to World Health Organization's report, whole world patients with depression reaches more than 200,000,000.Large-scale in the world epidemiological study shows that " depression " is number four at present, has 3%～5% lifelong prevalence at least, will be number two to the year two thousand twenty, is only second to ischemic heart desease in world's disabling condition.
The chemical synthetic drug that is used for the treatment of depression at present mainly contains tricyclic antidepressants, oxidase inhibitor and 5-hydroxy tryptamine cell reabsorption inhibitor, but untoward reaction is in various degree arranged all, after taking for a long time, serious toxic and side effects can occur, influence patient's life quality greatly.Therefore, press for efficient, the safe antidepressant drug of searching.
From Chinese herbal medicine, seek and development has the medicine of good antidepressant effect, have good effect, side effect little, be fit to take for a long time and many advantages such as safe and reliable, more and more cause people's attention.
Summary of the invention:
Technical problem to be solved by this invention is good effect in the research design natural plants, side effect is little, suitable takes and safe and reliable antidepressant drug for a long time.
The present invention is a raw material with natural plants or Chinese crude drug, adopt one or more technologies in the technologies such as solvent extraction method, solvent extraction, resin adsorption method or carbon dioxide supercritical fluid extraction, and in conjunction with conventional drying method such as concentrate drying, drying under reduced pressure or lyophilizations, utilization comprises that methods such as adsorbent resin column chromatography, vacuum liquid phase column chromatography, silica gel column chromatography, Sephadex gel filtration chromatography, mesolow column chromatography and high-pressure liquid phase (HPLC) column chromatography and precipitation, crystallization obtain phytosterin compound or total-sterol extract.
Above-mentioned natural plants or Chinese medicine comprise Bulbus Lilii, the Radix Paeoniae Alba, Fructus Jujubae, Semen sojae atricolor (or soybean oil deodorizer distillate), Radix Achyranthis Bidentatae, Semen Brassicae campestris, Semen Tritici aestivi (or Testa Tritici) etc.
In adopting solvent extraction method, organic solvent or two or more mixed solvents that dissolve each other such as the optional water of solvent for use, methanol, ethanol, propanol, butanols, amylalcohol, acetone, ethyl acetate, Ethyl formate, chloroform, dichloromethane, ether or petroleum ether, at room temperature dipping extracts or with the reflux, extract, under supersound extraction or the heated condition, extraction time can be once, also can be repeatedly.
In adopting solvent extraction, the above-mentioned extract that obtains can be suspended in water and directly extract with suitable solvent butanols, amylalcohol, ethyl acetate, Ethyl formate, chloroform, dichloromethane, ether or petroleum ether etc., extraction times can be once, also can be repeatedly.
Above-mentioned resin method is the macroporous adsorbent resin method, and water, alcohol or hydrous alcohol extraction thing can be handled with macroporous adsorbent resin, discard the water elution part, and all or part of collection alcohol eluting part promptly.
The carbon dioxide supercritical extraction method that is adopted can according to circumstances add suitable entrainer, as cyclohexane extraction, chloroform, ethyl acetate, methanol or ethanol etc.
Phytosterin compound of the present invention comprises sterol, sterol derivative, sterol ester, steroline, acidylate steroline and their derivant.
Described total-sterol extract is meant the extract that contains above-mentioned one or more phytosterin compounds that obtains by the said extracted separation method by in natural plants or the Chinese medicine, and its total sterol content is 50～90%.
Described sterol is sitosterol (Sitosterol), stigmasterol (Stigmasterol), campesterol (Campesterol) brassicasterol (brassicasterol), cholesterol (cholesterol), chondrillasterol (spinasterol), 24-ethylidenecholest-5-en-3.beta.-ol. (fucosterol), lanosterol (lanosterol), avenasterol (avenasterol), this sterol of standing grain (gramisterol), poriferasterol (poriferasterol), fungisterol (fungisterol), rosasterol (rosasterol), three-coloured amaranth sterol (amasterol), coprostenol (epicoprosterol), Codiumfragile(sur.) Hariot. sterol (codisterol), blunt leaf sterol (obtusifoliol), a species of small clam living in fresh water sterol (corbisterol), herba ineritis gracilis sterol (chondrilla sterol), desmosterol (desmosterol), ] paulownia sterol (clerosterol), euphol (euphorbosterol) etc. derives from the sterol of plant.
Described sterol derivative is meant in the sterol derivant of partly or entirely double-bond hydrogenation hydrogenation or 7-position dehydrogenation or oxidation etc.
Described sterol ester is the sterol ester of sterol and unsaturated fatty acid or ferulic acid formation.Its unsaturated fatty acid has 16～22 carbon atoms and one or more unsaturated carbon-carbon double bonds.
Described steroline is that sterol combines the steroline that forms with one or more monosaccharide such as natural pentose or hexoses.Described monosaccharide is: D-glucose (D-glucose), D-mannose (D-mannose), D-galactose (D-galactose), D-allose (D-allose), L-arabinose (L-arabinose), D-lyxose (D-lyxose), D-xylose (D-xylose), D-ribose (D-ribose), D-fructose (D-fructose), L-sorbose (sorbose), L-rhamnose (rhamnose) or L-husband sugar (L-fucose) etc.
Described acidylate steroline is the acidylate steroline that above-mentioned arbitrary steroline and unsaturated fatty acid form.Its unsaturated fatty acid has 16～22 carbon atoms and one or more unsaturated carbon-carbon double bonds.
Phytosterin compound of the present invention and total-sterol extract have carried out following animal effect experiment:
1, phytosterin compound antidepressant effect test
It is representative that phytosterin compound is selected cupreol (I), cupreol glucoside (II) and inferior oleoyl glucosyl group cupreol (III), adopts mice forced swimming test, the experiment of antagonism reserpine and voluntary activity experiment carrying out antidepressant effect to detect and checking.
1. the mandatory swimming test of mice (FST)
With the mandatory swimming depression model of the mice of classics, observed behind the oral or lumbar injection various dose phytosterin compound of 1 property of mice influence, to estimate the antidepressant activity of this chemical compound to its mandatory non-swimming time.Get male ICR mouse, body weight 24-28g.Administration experimentized after 1 hour, mice was placed in the glass jar (diameter 10cm, high 20cm) that fills 25 ℃ of water, and depth of water 10cm makes mice swimming 6 minutes, disregards in preceding 2 minutes, writes down the dead time of animal accumulative total in back 4 minutes.Experimental result shows, the inferior oleoyl glucosyl group cupreol (III) of the cupreol (I) of oral 90mg/ml or lumbar injection 30mg/kg, the cupreol glucoside (II) of 30mg/ml and 30mg/ml all can significantly reduce the mice forced swimming dead time (P＜0.05) (seeing Table 2,3,4).
Table 2. cupreol is to the influence of mice non-swimming time
**P＜0.01，
*P＜0.05 vs control group
Table 3. cupreol glucoside is to the influence of mice non-swimming time
| Medicine | Dosage (mg/kg) | Route of administration | Number of animals | The forced swimming dead time (s) |
| The blank group | - | Irritate stomach | 8 | 150.8±22.5 |
| Sample sets | 30 | Irritate stomach | 8 | 98.9±24.2** |
**p＜0.01，
*p＜0.05
The inferior oleoyl glucosyl group of table 4. cupreol is to the influence of mice non-swimming time
| Medicine | Dosage (mg/kg) | Route of administration | Number of animals | The forced swimming dead time (s) |
| The blank group | - | Irritate stomach | 8 | 153.7±19.2 |
| Sample sets | 30 | Irritate stomach | 8 | 94.1±8.2** |
**p＜0.01，
*p＜0.05
2. the antagonism reserpine is tested at the blepharoptosis that mice causes
At the blepharoptosis model that mice causes, observed the influence that 1 property of mice lumbar injection gives the blepharoptosis that reserpine caused behind various dose phytosterin compound-cupreol, with the reserpine of classics to estimate the antidepressant activity of this chemical compound.Get male ICR mouse, body weight 24-28g.Lumbar injection gives the cupreol of various dose, and simultaneously subcutaneous injection gives the reserpine of 2.5mg/kg, measures blepharoptosis after 1 hour.Experimental result shows the blepharoptosis (seeing Table 5) that the remarkable antagonism reserpine of cupreol energy of lumbar injection 30mg/kg causes mice.
Table 5. cupreol causes the influence of blepharoptosis mice to reserpine
3. cupreol is to the influence (LMA) of mice voluntary activity
Whether the oral cupreol of observation mice to the influence of spontaneous activity, has central excitation or inhibitory action with the check cupreol in forced swimming experiment effective dosage ranges.
Adopt Auto Track motion to resolve instrument (U.S. Columbus Instruments) and observe the mice voluntary activity.Get male ICR mouse, body weight 24-28g.The cupreol of lumbar injection 30mg/kg or oral 90mg/kg was put into the spacious case of the lucite of resolving instrument with mice after 1 hour, observed interior 10 minutes the spontaneous activity of case of animal, and observation index comprises the horizontal movement number, number and total motion number move both vertically.Experimental result shows that the cupreol in the forced swimming effective dosage ranges does not obviously influence (table 6) to the mice voluntary activity.
Table 6. cupreol is to the influence of spontaneous activity in mice
More than experiment shows, but the mouse peritoneal injection gives the cupreol antagonism blepharoptosis that reserpine causes, mouse stomach gives phytosterin compound can significantly reduce the forced swimming dead time, and this effect is not because the central excitation effect produces, and illustrates that phytosterin compound such as cupreol etc. have antidepressant effect.
2, Bulbus Lilii total-sterol extract antidepressant effect test
1. the mandatory swimming test of mice (FST)
Experimental technique is the same
Table 7. various dose Bulbus Lilii total-sterol extract is to the influence of mice non-swimming time
2. mouse tail suspension experiment
Behind the male mice gastric infusion 1h, the position of mice tail end 2cm is attached on the high horizontal rod of destage face 35cm, makes animal become the reversal of the natural order of things state.Observe 6min, respectively organize the accumulative total dead time of mice in the 4min of back.
Table 8. Bulbus Lilii total-sterol extract mouse tail suspension experimental result
3. spontaneous activity in mice test
Experimental technique is the same
Table 9. Bulbus Lilii total-sterol extract is to the influence of spontaneous activity in mice
| Control | The Bulbus Lilii total-sterol extract (40mpk, po@lh) | Potent(vs Control) | P value | |
| Total | 2778.6±194.7 | 3705.3±218.9 | 133.3 | ＜0.05 |
| Ambul | 2057.4±188.4 | 2703.3±230.3 | 131.4 | ＜0.05 |
| Vertical | 101.1±28.4 | 157.1±35.6 | 155.4 | ＞0.05 |
3, different plant extract antidepressant effect tests
Experimental technique is the same.
The different plant extracts of table 10. are to the influence of mice non-swimming time
The 13C NMR data of table 1. cupreol glucoside (II) and inferior oleoyl glucosyl group cupreol (III)
Phytosterin compound described in the present invention is as the active ingredient of central nervous system disease medicines such as preparation treatment depression, anxiety, can use separately or share or combine, make the central nervous system disease medicines such as treatment depression, anxiety of peroral dosage form or non-peroral dosage form according to conventional method with suitable excipient etc.
Embodiment
Embodiment 1: the extraction separation of phytosterin compound acidylate sitosterol glucoside (Acylated sitosteryl glucoside).
Get dry bulb (leaf) the sheet 1kg of liliaceous plant Bulbus Lilii, use 80% alcohol reflux, concentrated lixiviating solution gets ethanol extraction, extract mixture is suspended from the water, uses petroleum ether extraction, concentrate ligroin extraction, silica gel column chromatography on the ligroin extraction, gradient elution, wherein 15～16
#Part obtains the inferior oleoyl 3-O-glucosyl group-cupreol (the NMR data see Table 1) of 6 '-O-through silica gel column chromatography again.
Embodiment 2: the extraction separation of phytosterin compound cupreol glucoside
Get dry bulb (leaf) the sheet 1kg of liliaceous plant Bulbus Lilii, use 80% alcohol reflux, concentrated lixiviating solution gets ethanol extraction, extract mixture is suspended from the water, use ethyl acetate extraction, concentrate ethyl acetate extract, silica gel column chromatography on the ethyl acetate extract, the chloroform-methanol gradient elution obtains cupreol-3-O-glucoside (the NMR data see Table 1) through the SephadexLH20 gel filtration chromatography again.
Embodiment 3: phytosterin compound cupreol extraction separation
Get dry bulb (leaf) the sheet 1kg of liliaceous plant Bulbus Lilii, use 80% alcohol reflux, concentrated lixiviating solution gets ethanol extraction, extract mixture is suspended from the water, uses petroleum ether extraction, concentrate ligroin extraction, silica gel column chromatography on the ligroin extraction, normal hexane-ethyl acetate gradient elution, crystallization in the chloroform methanol solution obtains cupreol.
Embodiment 4: the extraction separation of phytosterin compound in the Fructus Jujubae
Get dry Fructus Jujubae 80% alcohol reflux, concentrated lixiviating solution gets ethanol extraction, and extract mixture is suspended from the water, uses ethyl acetate extraction, concentrate ethyl acetate extract; Ethyl acetate extract is suspended in 5% sodium hydrate aqueous solution, uses ethyl acetate extraction, silicagel column on the extract, normal hexane-chloroform-methanol gradient elution, eluting fraction is placed or recrystallizing methanol, obtains cupreol and cupreol glucoside.
Embodiment 5: the extraction separation of sterol compound in the Radix Paeoniae Alba
Get Radix Paeoniae Alba decoction pieces, use 85% alcohol reflux, concentrated lixiviating solution gets ethanol extraction, extract mixture is suspended from the water, uses petroleum ether extraction, concentrate ligroin extraction, silica gel column chromatography on the ligroin extraction, normal hexane-ethyl acetate gradient elution, crystallization in the chloroform methanol solution obtains cupreol.
Embodiment 6: the extraction separation of total-sterol extract in the Bulbus Lilii
Get dry bulb (leaf) sheet of liliaceous plant Bulbus Lilii, use 80% alcohol reflux, concentrated lixiviating solution gets ethanol extraction, extract mixture is suspended from the water, uses chloroform extraction, in chloroform extract solution acetone, filter, behind the acetone soln concentrate drying, add the methanol hot melt, behind the placement certain hour, filter, the collecting precipitation thing, drying gets the Bulbus Lilii total-sterol extract.
Embodiment 7: the extraction separation of total-sterol extract in the Semen sojae atricolor
Soyabean deodorization distillate is dissolved in ethyl acetate, uses 5% sodium hydroxide extraction, water system is heat-fused in methanol behind the concentrate drying, places, and leaches precipitation and both has been total-sterol extract.
Embodiment 8: the extraction separation of total-sterol extract in the Radix Achyranthis Bidentatae
Get dry Radix Achyranthis Bidentatae, pulverize, use 80% alcohol reflux, extract mixture is suspended from the water, with ethyl acetate extraction, after the washing of extract reuse 5% sodium hydroxide, puts cryoprecipitate with the methanol hot melt, the Radix Achyranthis Bidentatae total-sterol extract of repeated multiple times.
Claims (3)
1, phytosterin compound or the total-sterol extract application in the preparation antidepressant drug; Wherein said phytosterin compound is cupreol, cupreol glucoside or inferior oleoyl glucosyl group cupreol; Described phytosterin compound or total-sterol extract are what extract from Semen sojae atricolor, Radix Achyranthis Bidentatae, the Radix Paeoniae Alba, Bulbus Lilii or Fructus Jujubae.
2, phytosterin compound according to claim 1 or the total-sterol extract application in the preparation antidepressant drug, the total sterol content that it is characterized in that wherein said total-sterol extract is 50-90%.
3, phytosterin compound according to claim 1 or the total-sterol extract application in the preparation antidepressant drug, it is characterized in that with in phytosterin compound or the total-sterol extract one or more as active ingredient, with the pharmaceutical excipient combination, preparation treatment depressive illness medicine; This medicine is oral or non-peroral dosage form.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200510111265XA CN100441191C (en) | 2005-12-08 | 2005-12-08 | Use of steroidal compound and total steroidal extract for preparing anti-depression drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB200510111265XA CN100441191C (en) | 2005-12-08 | 2005-12-08 | Use of steroidal compound and total steroidal extract for preparing anti-depression drug |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1977848A CN1977848A (en) | 2007-06-13 |
| CN100441191C true CN100441191C (en) | 2008-12-10 |
Family
ID=38129268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB200510111265XA Expired - Fee Related CN100441191C (en) | 2005-12-08 | 2005-12-08 | Use of steroidal compound and total steroidal extract for preparing anti-depression drug |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100441191C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018207178A1 (en) | 2017-05-07 | 2018-11-15 | Yeda Research And Development Co. Ltd. | Methods of treating psychiatric stress disorders |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106146597A (en) * | 2016-07-05 | 2016-11-23 | 浙江海洋大学 | A kind of saringosterol compound and extracting method, application |
| CN106146596A (en) * | 2016-07-05 | 2016-11-23 | 浙江海洋大学 | A kind of Sargassum phyllocystum Tseng et Lu,Sargassum horneri (Turn.) C. Ag. (Fucus horneri (Turn.)C.Ag.,Spongocarpus horneri Kutz.) Sitosterolum compound and extracting method, application |
| CN109528806B (en) * | 2018-12-19 | 2021-08-06 | 刘东波 | Sterol composition in pumpkin seed oil, application thereof and medicine for treating prostatic hyperplasia |
| CN112107606B (en) * | 2020-11-05 | 2022-06-28 | 陈乃宏 | Application of Chinese parsley or extract thereof in preparation of antidepressant drug |
| CN113509474A (en) * | 2021-08-31 | 2021-10-19 | 广东工业大学 | Application of beta-sitosterol in preparation of anti-neuritis medicine |
| CN116999533B (en) * | 2023-08-16 | 2024-06-07 | 秦皇岛市山海关药业有限责任公司 | Heart-nourishing and pulse-activating granule, preparation method thereof and application thereof in antidepressant product |
-
2005
- 2005-12-08 CN CNB200510111265XA patent/CN100441191C/en not_active Expired - Fee Related
Non-Patent Citations (6)
| Title |
|---|
| 大豆植物甾醇及其生理功能. 李劲松等.加工技术，第5期. 2004 |
| 大豆植物甾醇及其生理功能. 李劲松等.加工技术，第5期. 2004 * |
| 植物甾醇发展前景. 胡学烟.粮食与油脂，第1期. 2001 |
| 植物甾醇发展前景. 胡学烟.粮食与油脂，第1期. 2001 * |
| 植物甾醇来源、提取、分析 技术及其食品开发. 寇明钰等.粮食与油脂，第8期. 2004 |
| 植物甾醇来源、提取、分析 技术及其食品开发. 寇明钰等.粮食与油脂，第8期. 2004 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018207178A1 (en) | 2017-05-07 | 2018-11-15 | Yeda Research And Development Co. Ltd. | Methods of treating psychiatric stress disorders |
| EP3821888A1 (en) | 2017-05-07 | 2021-05-19 | Yeda Research and Development Co. Ltd | Lxr agonists for treating psychiatric stress disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1977848A (en) | 2007-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100441191C (en) | Use of steroidal compound and total steroidal extract for preparing anti-depression drug | |
| CN101242850A (en) | Composition, function and use of xanthoceras sorbifolia extract and compound isolated from same, method for preparing same | |
| CN101279964B (en) | Guaiane type sesquiterpenes, preparation and medical use thereof | |
| CN1972702A (en) | Composition comprising xanthoceras sorbifolia extracts, compounds isolated from same, methods for preparing same and uses thereof | |
| CN101647850B (en) | New application of chemical component of eucommia bark used as plant estrogen | |
| CN104910240B (en) | Triterpenoid saponin in Bougainvillea glabra, the hypoglycemic drug with it as active component, and its preparation method and application | |
| CN104547104B (en) | Ramulus Ziziphi Spinosae leaf extract and its preparation method and application | |
| CN102504006A (en) | Steroid saponin compound in siberian fritillary bulb | |
| CN100344642C (en) | Process for preparing flaxseed lignan total glycoside extract and use thereof | |
| CN101972294A (en) | New usage of eucommia ulmoides chemical composition as vessel protective agent | |
| CN111440157B (en) | Method for simultaneously separating schaftoside, vitamin adopted-2 and ecdysone and application thereof | |
| CN105998103A (en) | Chestnut flower activated extract and preparation method and application thereof | |
| CN101011545A (en) | Method for extracting effective sites group of smilax China root | |
| CN100372865C (en) | Saponin compound and use of its glucoside in preparing medicine for treating neure injure | |
| Meyre-Silva et al. | Phytochemical and pharmacological analysis of Bauhinia microstachya (Raddi) Macbr.(Leguminosae) | |
| TAYONE et al. | Isolation and structure elucidation of potential Anti-Dengue metabolites from Tawa-Tawa (Euphorbia hirta Linn.) | |
| CN106674309A (en) | Coumarin glycoside, and preparation method and application thereof | |
| CN105503990A (en) | Novel withanolides compound as well as preparation method and medical application thereof | |
| CN113861301B (en) | Non-starch lily polysaccharide NSLP-1 and application thereof | |
| CN101648959B (en) | Coumaronochromones compound and preparation and application thereof | |
| CN110507662B (en) | Polygonatum sibiricum steroidal sapogenin and preparation method and application thereof | |
| CN101023979A (en) | Lamiophlomis-rotata leaf-stem distract and its preparing process and use | |
| CN101491530A (en) | Use of sterols compound and total-sterol extract in preparing analgesic | |
| CN107722087B (en) | Gynostemma pentaphylla flavonoid compound, preparation method thereof and application thereof in antitumor drugs | |
| CN101347418A (en) | Use of 8-0-4'type lignan in preparing anticomplement medicament |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20081210 Termination date: 20100108 |