CN1247855A - Preparation and application of tanshinpolyphenolic salt - Google Patents
Preparation and application of tanshinpolyphenolic salt Download PDFInfo
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- CN1247855A CN1247855A CN 98111076 CN98111076A CN1247855A CN 1247855 A CN1247855 A CN 1247855A CN 98111076 CN98111076 CN 98111076 CN 98111076 A CN98111076 A CN 98111076A CN 1247855 A CN1247855 A CN 1247855A
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- macroporous resin
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Abstract
The present invention prepares refined tanshinpolyphenolic salt through hot water extraction and macroporous resin separation. Tanshinpolyphenolic salt contains magnesium tanshinpolyphenolate B as main active component up to 60% and may be applied in the medicine for cardiac and cerebral vascular diseases.
Description
The present invention relates to the salviamiltiorrhizabung extract, more particularly extract the refining salvianolate that forms by the red sage root.
The single herbal medicine is used for the treatment of a kind of important means that disease is Chinese materia medica and folk medicine.The red sage root is simply to prevention and treatment cardiovascular disorder such as effective Chinese medicine such as stenocardia, coronary heart disease and apoplexy.The general using method of the red sage root is concluded and is mainly contained two big classes at present:
1. single salvia piece or after other Chinese medicines decoct into decoction of medicinal ingredients, take.
2. the finished medicines that becomes various formulations by factory process is as back uses such as oral preparation, injection and aerosols.
Red sage root finished medicines especially injection is widely used clinically.The Chemical Composition of the red sage root mainly is made up of fat-soluble composition and water-soluble components two portions.The chemical work of the previous red sage root concentrates on fat-soluble composition mostly, and therefrom isolating TANSHINONES is a series of diterpene compounds of representative, confirms that through pharmacological testing this compounds has certain physiologically active.Thereafter (pharmacy circular such as Chen Zheng hero.1981,16 (9), 2425) at first carried out the research of the water-soluble components of the red sage root, found rancinamycin IV, Salvianic acidA, salvianolic acid first and the second grade water-soluble cpds, pharmacologically active shows that they have the effect of certain enhancing mouse hypoxia-bearing capability.In view of salvianolic acid is difficult to obtain pure product, and the more easily separated and synthetic acquisition of rancinamycin IV and Salvianic acidA, so existing red sage root patent medicine preparation such as the water miscible Salvianic acidA of quality control major control of Radix Salviae Miltiorrhizae Injection and the content of rancinamycin IV, oral preparations then detects water miscible Salvianic acidA and fat-soluble TANSHINONES simultaneously.A large amount of pharmacology and clinical study result show that the activity of the water-soluble components of the red sage root is better than fat-soluble composition, and rancinamycin IV toxic side effect, Salvianic acidA represent the activity of the red sage root very unreasonable.Ma Li Lian waited and systematically the salvianolic acid compounds to be carried out extensive work the end of the eighties, isolated compounds such as salvianolic acid A, B and C, but failed fundamentally to illustrate the main active ingredient of the red sage root equally.((a) Planta Medica 1984,50 (3), 227; 1992,58 (2), 197; (b) J.Nat.Prod.1988,51 (1), 145; (C) Phytochemistry.1992,31 (2), 1068; When (d) ChineseChem.Lett.1993,4 (6), 501) Japanese scholar Xi Gang five husbands wait the full effective ingredient of research Treated with Radix Salviae Miltiorrhizae kidney, isolate salvianolic acid B magnesium, but do not illustrate it yet the active contribution of the red sage root (Chem, Pharm.Bull.1989,37 (2), 340).Because the effective ingredient research of the red sage root lags behind, the quality of domestic red sage formulation and effect can not get ensureing that the different lot number product clinical effectiveness of the product of different manufacturers or same producer differ greatly, and lack reliable Quality Control foundation.
The objective of the invention is by Study on extraction red sage root aqueous solution composition, the mould rope goes out a kind of method simple and easy, the efficient production salvianolate also to be determined to make quality control index with the salvianolic acid B magnesium in the poly phenolic acid of Radix Salviae Miltiorrhizae salt mixture, improves its treatment cardiovascular and cerebrovascular diseases result of use.
The present invention mainly pulverizes the back with the red sage root and carries with hydro-thermal, extracting fully, back water is concentrated, concentrated solution centrifuging, filtered liquid are removed impurity through macroporous resin adsorption with water wash, be adsorbed in polyphenol hydrochlorate on the macroporous resin through with moisture lower alcohol wash-out, elutriant is evaporated to certain volume, adds dehydrated alcohol, alcohol precipitation, inclining supernatant liquor and discards throw out, and the supernatant liquor that inclines is evaporated to dried.Drying and crushing gets salvianolic acid salt.
The present invention implements through the following steps.
[separation of salvia-soluble composition]
Pulverize red rooted salvia, use hot water extraction then, the centrifuging of extracting solution concentrating under reduced pressure, solution is further through Sephadex LH-20, TSK gel Toyopearl HW 40 F, reversed phase chromatography carrier column chromatographies such as MCI gel CHP 20P.CosmosilODS obtain eight compounds respectively, and to measure each compound structure as follows through chemistry and spectral method:
Salvianolic acid salt is the mixture of salvia-soluble phenol sexual element, mainly contain salvianolic acid B magnesium (compound 6), salvianolic acid salt mixture and existing salvia-soluble composition product such as Radix Salviae Miltiorrhizae Injection, in the kind of effective ingredient, there is very big difference aspects such as content and activity.Through showing with the HPLC quantitative analysis, salvianolic acid B magnesium is the main ingredient in the salvia-soluble composition, and its content accounts for 60% of salvia-soluble phenol sexual element.
[biological activity determination]
The antioxygenation of red sage root component adopts (Biochemical Pharmacology 1992 such as Liu, 43 (2), 147) reported method is measured, and platelet aggregation-against and hypoxia endurance test adopt Liang Zijun (Li Yikui etc., herbal pharmacology experimental technique etc., Shanghai science tech publishing house, 1991 the 82nd page) and Qi Chen east (Li Yikui etc., herbal pharmacology experimental methodology, Shanghai science tech publishing house, 1991, the 110th page) reported method mensuration.Measurement result sees Table one to table six.
Eight compounds of salvia miltiorrhiza tanshinoate salt except that compound 7 must measure atomic, all the other seven compounds are anti-oxidant to it respectively, platelet aggregation-against and mouse hypoxia tolerance are tested, compound 6 all shows the strongest activity on four screening models as can be known from table one to table four, and Salvianic acidA is then active unsatisfactory.Utilize hydrogen type cation exchange resin to prepare the corresponding acidulants of compound 6 and salvianolate respectively, it is suitable with compound 6 during at high dosage as its activity of mixture from the visible salvia miltiorrhiza tanshinoate salt of table five and table six at the activity intensity on the mouse hypoxia tolerance model of platelet aggregation-against further to have compared salt and acid, then not as compound 6, their acidulants activity is the poorest during low dosage.Above-mentioned chemistry and pharmacology result show that the content of compound 6 can be used as the quality control index of salvianolate, can be in the application in the treatment cardiovascular medicament through biological activity test proof salvianolate.
Table one. red sage root component produces the influence of MDA to the tetrachloro-methane induction rat hepatocytes
| Compound | Concentration (μ M) | MDA measures statistical value | Effect |
| ????1 | ????0.5 ????1.0 | ????↓P＜0.001 ????↓P＜0.001 | ????++ ????++ |
| ????2 | ????0.5 ????1.0 | ????↓P＜0.001 ????↓P＜0.001 | ????++ ????++ |
| ????3 | ????0.5 ????1.0 | ????↓P＜0.001 ????↓P＜0.001 | ????++ ????++ |
| ????4 | ????0.5 ????1.0 | ????↓P＜0.001 ????↓P＜0.001 | ????++ ????++ |
| ????5 | ????0.5 ????1.0 | ????↓P＜0.001 ????↓P＜0.001 | ????++ ????++ |
| ????6 | ????0.5 ????1.0 | ????↓P＜0.001 ????↓P＜0.001 | ????++ ????++ |
| ????8 | ????0.5 ????1.0 | ????↓P＜0.001 ????↓P＜0.001 | ????++ ????++ |
Annotate :-invalid ,+effectively, ++ produce effects
Table two. red sage root component is to H
2O
2Induce the erythrocytic hemolytic influence of rat
| Compound | Inhibiting rate | Effect |
| ????1 ????2 ????3 ????4 ????5 ????6 ????8 | ????100％ ????100％ ????100％ ????100％ ????100％ ????100％ ????100％ | ????++ ????++ ????++ ????++ ????++ ????++ ????++ |
Annotate: 1)-invalid ,+effectively, ++ produce effects.
2) sample concentration is 0.33mg/ml, and is external.
Table three. red sage root component is to the influence of anoxic mouse
| Compound | The survival time statistics | Effect |
| ????1 | ????P＞0.05 | ????- |
| ????2 | P＜0.01 prolongs 42% | ????++ |
| ????3 | P＜0.05 prolongs 23% | ????+ |
| ????4 | P＜0.05 prolongs 45% | ????+ |
| ????5 | ????P＞0.05 | ????- |
| ????6 | P＜0.01 prolongs 65% | ????++ |
| ????8 | P＜0.01 prolongs 69% | ????++ |
Annotate: 1)-invalid ,+effectively, ++ produce effects.
Table four. red sage root component is to the influence of rat platelet aggregation
| Compound | Concentration (μ g/ml) | Inhibiting rate | Effect |
| ????1 | ????180 ????900 | ????0％ ????0％ | ????- |
| ????2 | ????180 ????900 | ????0％ ????13％ | ????- |
| ????3 | ????180 ????900 | ????0％ ????18％ | ????- |
| ????4 | ????180 ????900 | ????0％ ????28％ | ????- |
| ????5 | ????180 ????900 | ????0％ ????44％ | ????+ |
| ????6 | ????180 ????450 ????900 | ????0％ ????15％ ????74％ | ????+ |
| ????8 | ????180 ????900 | ????0％ ????20％ | ????- |
Annotate :-invalid ,+effectively, ++ produce effects
Table five. the platelet aggregation inhibitory activity of compound 6 and salvianolic acid salt and their acidulants
| Sample | Concentration (μ g/ml) | Inhibiting rate (%) |
| ????6 | ????900 ????450 | ????94 ????74 |
| 6 acidulants | ????900 ????450 | ????68 ????22 |
| Salvianolic acid salt | ????900 ????450 | ????94 ????20 |
| The salvianolic acid salt acidulants | ????900 ????450 | ????23 ????0 |
Annotate: in vitro tests.
Table six. compound 6 and salvianolic acid salt and their acidulants are to the influence (200mg/Kg) of anoxic mouse
| Sample | Survive the time lengthening rate |
| ????6 | ????78％ |
| 6 acidulants | ????28％ |
| Salvianolic acid salt | ????78％ |
| The salvianolic acid salt acidulants | ????14％ |
Annotate: intraperitoneal injection.
[preparation of salvianolate]
The red sage root of chopping is boiled with boiling water and carries 2-4 time, first water consumption be about the crude drug amount 4-8 doubly, extracting solution is through concentrating after-filtration, (macroporous resin is to be the commercially available porousness adsorption chromatography carrier that bridging materials makes with vinylbenzene by macroporous resin adsorption, can use Amberlite XAD series and domestic resin roughly the same, for example raise the 1300-1 macroporous resin of continent pharmaceutical factory etc.) wash decon with water, use moisture C again
1-C
5The lower alcohol wash-out, the wash-out lower alcohol is methyl alcohol, ethanol or propyl alcohol etc., the concentration of moisture lower alcohol is 30-80%, the aqueous alcohol consumption is about 5-10 times of crude drug amount, collect the lower alcohol elutriant, concentrating under reduced pressure, the alcohol concn of final alcohol precipitation is 75-95%, the 0.5-2 that the alcohol precipitation liquor capacity is equivalent to the crude drug amount doubly, product yield more than 2.5% of dose of making a living.
Providing most preferred embodiment below further specifies the present invention but the present invention is not limited.
Embodiment 1
Red rooted salvia after 100 kilograms of pulverizing drops into extractor, carries three times with 600,300,250 liter poach successively at 90-100 ℃, and extraction time is 2 hours at every turn, merges No. three times extracting solution, after the centrifuging supernatant liquor is evaporated to 250 liters.Concentrated solution is slowly flow through the adsorption column that 300 liter 1300-1 macroporous resins (production of Yang Zhou pharmaceutical factory) is housed, remove impurity with 800 liters washings adsorption column after, wash out salvianolic acid salt with 600 liters, 50% ethanol again.Collect 50% ethanol elutant, after being evaporated to 10 liters, under agitation slowly add 90 liter dehydrated alcohols, finish and placed 2 hours, centrifugally then incline to supernatant liquor and discard throw out, supernatant concentration is to doing, further dry and pulverize 3 kilograms in brown salvianolic acid salt powder, be 3% by the raw medicinal herbs yield.
Claims (5)
1. a method for preparing salvianolate is characterized in that
A. the red sage root after pulverizing is carried with hydro-thermal, and extracting fully, back water is concentrated concentrated solution centrifuging;
B. filtered liquid is removed impurity through macroporous resin adsorption and with water wash;
C. be adsorbed in polyphenol hydrochlorate on the macroporous resin through with moisture lower alcohol wash-out;
D. elutriant is evaporated to certain volume and adds the dehydrated alcohol alcohol precipitation, inclines to supernatant liquor and discard
Throw out;
E. incline on clear liquid be evaporated to driedly, drying and crushing gets salvianolic acid salt.
2. preparation method according to claim 1 is characterized in that it is the polystyrene type porousness polymeric adsorbent of bridging materials that macroporous resin can be with vinylbenzene.
3. preparation method according to claim 1 is characterized in that being adsorbed in the moisture C of product on the macroporous resin
1-C
5The lower alcohol wash-out.
4. preparation method according to claim 3 is characterized in that being adsorbed in the moisture C of product of macroporous resin
1-C
5The lower alcohol wash-out, elutriant concentration is 30-80%.
5. preparation method according to claim 1 is characterized in that the polyphenol hydrochlorate of gained can be used in the treatment cardiovascular medicament.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98111076A CN1129572C (en) | 1998-09-11 | 1998-09-11 | Preparation and application of tanshinpolyphenolic salt |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98111076A CN1129572C (en) | 1998-09-11 | 1998-09-11 | Preparation and application of tanshinpolyphenolic salt |
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| CN1247855A true CN1247855A (en) | 2000-03-22 |
| CN1129572C CN1129572C (en) | 2003-12-03 |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003099759A1 (en) * | 2002-05-23 | 2003-12-04 | Tianjin Tasly Pharmaceutical Co., Ltd. | Preparation and application of transhintotalphenolic acid |
| WO2005051404A1 (en) | 2003-09-23 | 2005-06-09 | Tianjin Tasly Pharmaceutical Co., Ltd. | Pharmaceutical composition for the treatment of cardiovascular and cerebrovascular diseases |
| CN1305866C (en) * | 2003-08-19 | 2007-03-21 | 江苏扬子江药业集团有限公司 | Method of extracting phenolic components from chinese medicine red sage root and its freeze dried powder injection agent |
| CN100335076C (en) * | 2003-04-18 | 2007-09-05 | 上海通用药业股份有限公司 | Art for extracting red sage root water soluble ingredient and removing impurities |
| CN101210002B (en) * | 2006-12-27 | 2011-04-20 | 中国科学院大连化学物理研究所 | Method for separating and preparing salvianolic acid B chemical reference substance |
| CN102058599A (en) * | 2009-11-17 | 2011-05-18 | 中国科学院上海药物研究所 | Salvianolate, and preparation method and application thereof |
| CN102274283A (en) * | 2011-09-05 | 2011-12-14 | 邵明川 | Preparation method of red-rooted salvia root active fraction |
| CN102100742B (en) * | 2003-03-27 | 2012-03-28 | 成都地奥制药集团有限公司 | Water-solubility extract of root of red-rooted salvia, preparation method thereof and application thereof |
| CN1762341B (en) * | 2005-09-29 | 2012-03-28 | 丛晓东 | Salvianolic acid compound for treating cardiovascular and cerebrovascular disease and liver disease, and application thereof |
| CN102091125B (en) * | 2005-01-28 | 2012-11-21 | 成都地奥九泓制药厂 | Method for preparing total salvianolic acid |
| CN104042707A (en) * | 2013-11-28 | 2014-09-17 | 天津天狮生物发展有限公司 | Traditional Chinese medicinal composition containing Polygonum multiflorum Thunb extract, and preparation method thereof |
| WO2014201994A1 (en) | 2013-06-17 | 2014-12-24 | 天士力制药集团股份有限公司 | Salvia miltiorrhiza extract, micropellet formulation thereof, methods of preparing same, and uses thereof |
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1998
- 1998-09-11 CN CN98111076A patent/CN1129572C/en not_active Expired - Lifetime
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| US7641922B2 (en) | 2002-05-23 | 2010-01-05 | Tianjin Tasly Pharmaceutical Co., Ltd. | Preparation and application of transhintotalphenolic acid |
| WO2003099759A1 (en) * | 2002-05-23 | 2003-12-04 | Tianjin Tasly Pharmaceutical Co., Ltd. | Preparation and application of transhintotalphenolic acid |
| CN102100742B (en) * | 2003-03-27 | 2012-03-28 | 成都地奥制药集团有限公司 | Water-solubility extract of root of red-rooted salvia, preparation method thereof and application thereof |
| CN100335076C (en) * | 2003-04-18 | 2007-09-05 | 上海通用药业股份有限公司 | Art for extracting red sage root water soluble ingredient and removing impurities |
| CN1305866C (en) * | 2003-08-19 | 2007-03-21 | 江苏扬子江药业集团有限公司 | Method of extracting phenolic components from chinese medicine red sage root and its freeze dried powder injection agent |
| WO2005051404A1 (en) | 2003-09-23 | 2005-06-09 | Tianjin Tasly Pharmaceutical Co., Ltd. | Pharmaceutical composition for the treatment of cardiovascular and cerebrovascular diseases |
| LT5433B (en) | 2003-09-23 | 2007-07-25 | Tianjin Tasly Pharmaceuticals Co., Ltd. | Pharmaceutical composition for the treatment of cardiovascular and cerebrovascular diseases |
| CN102091125B (en) * | 2005-01-28 | 2012-11-21 | 成都地奥九泓制药厂 | Method for preparing total salvianolic acid |
| CN1762341B (en) * | 2005-09-29 | 2012-03-28 | 丛晓东 | Salvianolic acid compound for treating cardiovascular and cerebrovascular disease and liver disease, and application thereof |
| CN101210002B (en) * | 2006-12-27 | 2011-04-20 | 中国科学院大连化学物理研究所 | Method for separating and preparing salvianolic acid B chemical reference substance |
| CN102058599B (en) * | 2009-11-17 | 2014-06-04 | 中国科学院上海药物研究所 | Salvianolate, and preparation method and application thereof |
| CN102058599A (en) * | 2009-11-17 | 2011-05-18 | 中国科学院上海药物研究所 | Salvianolate, and preparation method and application thereof |
| CN102274283A (en) * | 2011-09-05 | 2011-12-14 | 邵明川 | Preparation method of red-rooted salvia root active fraction |
| CN102274283B (en) * | 2011-09-05 | 2013-04-17 | 邵明川 | Preparation method of red-rooted salvia root active fraction |
| WO2014201994A1 (en) | 2013-06-17 | 2014-12-24 | 天士力制药集团股份有限公司 | Salvia miltiorrhiza extract, micropellet formulation thereof, methods of preparing same, and uses thereof |
| CN104042707A (en) * | 2013-11-28 | 2014-09-17 | 天津天狮生物发展有限公司 | Traditional Chinese medicinal composition containing Polygonum multiflorum Thunb extract, and preparation method thereof |
| CN104042707B (en) * | 2013-11-28 | 2016-04-13 | 天津天狮生物发展有限公司 | A kind of Chinese medicine composition and preparation method containing Radix Polygoni Multiflori extract |
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| Publication number | Publication date |
|---|---|
| CN1129572C (en) | 2003-12-03 |
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Assignee: Shanghai Green Valley Pharmaceutical Co., Ltd. Assignor: Shanghai Institute of Materia Medica, Chinese Academy of Sciences Contract fulfillment period: 2018.9.10 to 2018.9.10 Contract record no.: 2008310000199 Denomination of invention: Preparation and application of tanshinpolyphenolic salt Granted publication date: 20031203 License type: Exclusive license Record date: 20081022 |
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