CN103245687A - Component-structure-based quality control and detection method for danshen injection - Google Patents
Component-structure-based quality control and detection method for danshen injection Download PDFInfo
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Abstract
The invention provides a novel component-structure-based quality control and detection method for danshen injection. The quality is judged according to phenolic acid components and sugar components which represent the whole property in the danshen injection. The optimal judgment standard is that a ratio of the phenolic acid components to the sugar components is (1-95 percent) to (90-1 percent); the composing ratios of tanshinol, protocatechualdehyde, caffeic acid, danshinolic acid E1 subjected to tanshinol removal, danshinolic acid E2 subjected to tanshinol removal, danshinolic acid A, danshinolic acid B, danshinolic acid C, danshinolic acid D and rosmarinic acid in the danshen phenolic acid is (1-95 percent):(5-95 percent):(1-20 percent):(1-20 percent):(5-20 percent):(1-50 percent):(5-20 percent):(1-10 percent):(1-20 percent):(1-20 percent); the sum of the content of the phenolic acid components and the content of the sugar components is more than 35-90 percent of a total solid content; and the content of the phenolic acid components is not less than 40-80 percent of the total solid content.
Description
Technical field
The present invention relates to the quality control standard of compound Chinese medicinal preparation, especially a kind of quality control detection method field based on component structure for danshen injections.
Background technology
The one-tenth with global feature that the effective substance of Chinese medicine preparation is made up of according to certain constituent ratio a plurality of components hives off.Modern pharmacology and fitochemical studies result show that non-certain single component of material base of Chinese medicine preparation performance drug effect works, but realizes synergy by many target spots, multicomponent.At present, the researchist recognizes that gradually the Chinese medicine preparation material base is studied and quality control can not be walked traditional plant approach of seeking monomer, content with certain active component or toxic component is formulated quality standard, but to see based on the integral body of Chinese medicine, be point of penetration with " component ", illustrate the material base of Chinese medicine and finally reach the purpose of the traditional Chinese medicine quality control that meets whole characteristics.Material foundation of tcm " component structure theory " thinks that the Chinese medicine preparation material base is an orderly integral body, have " three generating multi-dimension hierarchical structures ", formed by various ingredients, and also constituted by the certain proportioning of a plurality of compositions in each component, all there is the certain structure feature between component with in the component, this with just control the Chinese medicine preparation method for quality with certain index content at present and compare, both realized controllability, embodied the globality of Chinese medicine again.
Danshen injections is clinical Chinese medicine preparation commonly used, have promoting blood circulation and removing blood stasis, regulate the flow of vital energy have one's ideas straightened out, the effect of hemangiectasis and enhancement coronary blood flow, be used for prevention and treatment of diseases such as angina pectoris, myocardial infarction.Danshen injections mainly contains water-soluble root of red-rooted salvia phenolic acid compounds and carbohydrate, as danshensu, protocatechualdehyde, caffeic acid, remove danshensu salvianolic acid E 1, remove danshensu salvianolic acid E 2, salviandic acid A, tanshin polyphenolic acid B, salvianolic acid C, salvianolic acid D, Rosmarinic acid etc.Studies show that these compounds all have certain cardiovascular and cerebrovascular protective effect.
Summary of the invention
Goal of the invention:
The present invention will solve the existing deficiency of the quality control of danshen injections according to traditional Chinese medicine globality and systematic characteristics, and a kind of multidimensional structure method of quality control that represents component characteristics is provided.
Technical scheme:
A kind of quality control detection method based on component of danshen injections, being characterized as of this method controlled composition structure and component inner structure between the component of phenolic acid in the danshen injections and carbohydrate components, adopt HPLC finger-print, pre-column derivatization HPLC and NMR technology to measure the limited composition that represents globality, thus the whole content ratio of also controlling between the interior composition of injection of danshen fluid component and composition systemicly.The optimality criterion of weighing the danshen injections quality is:
The phenolic acid component: the content range of control of carbohydrate components is (1%-95%): (90%-1%); And danshensu, protocatechualdehyde, caffeic acid in the root of red-rooted salvia phenolic acid, remove danshensu salvianolic acid E 1, remove danshensu salvianolic acid E 2, the constituent ratio of salviandic acid A, tanshin polyphenolic acid B, salvianolic acid C, salvianolic acid D, each composition of Rosmarinic acid is respectively (1%-95%): (5%-95%): (1%-20%): (1%-20%): (5%-20%): (1%-50%): (5%-20%): (1%-10%): (1%-20%): (1%-20%); The content summation of phenolic acid component and carbohydrate components is greater than the 35-90% of total solid; The phenolic acid components contents is not less than the 40-80% of total solid.
Beneficial effect:
Traditional Chinese medicine preparation product is by synergy performance effect by numerous chemical constitutions.The effective substance of traditional Chinese medicine preparation product is made up of a certain component that polycomponent or multicomponent constitute, and there is significant difference in the biologically active between each component, and action target spot and mechanism also are not quite similar; Each compound structure also exists difference in the component, biologically active also exists difference, therefore, the material base formation of these components and composition performance optimum medicine efficacy exists certain uniqueness, namely exists unique composition architectural feature between the component or in the component between the compound.Danshen injections mainly comprises phenolic acid and carbohydrate components; these components have the cardiovascular effect of certain protection, studies show that root of red-rooted salvia phenolic acid has neural and cerebral ischemia protection, protection myocardial damage, antithrombotic and inhibition platelet activation, improves the effects such as propagation of diabetic vascular complications, inhibition vascular cell.Carbohydrate also is that the material base of its effect constitutes one of component, and red sage root carbohydrate has antioxidation activity and improves the mouse hypoxia-bearing capability, also can be by raising prohibitin protein expression performance protection H
2O
2Cause the effect of myocardial cell injury.Therefore, to the quality control of danshen injections, can not only replace the overall activity composition with danshensu or protocatechualdehyde.Importantly, the composition architectural feature of formation effective substance is left in the basket.Therefore, based on the component structure theory, illustrate between the phenolic acid of danshen injections and carbohydrate components and the architectural feature in the component, the real control with realizing the danshen injections quality guarantees its curative effect and security.The present invention has overcome existing deficiency to danshen injections production quality control detection method, and the quality control that may become a kind of danshen injections detects new method.
Description of drawings
Fig. 1 danshen injections multidimensional structure quality control synoptic diagram
Liposoluble ingredient finger-print in Fig. 2 danshen injections, (1.5-hydroxymethylfurfural wherein; 2. Sodium Danshensu; 3. protocatechualdehyde; 4. caffeic acid; 5. remove danshensu salvianolic acid E 1; 6. remove danshensu salvianolic acid E 2; 7. salvianolic acid D; 8. Rosmarinic acid; 9. tanshin polyphenolic acid B; 10. salviandic acid A; 11, salvianolic acid C)
Figure 32 50ml:16g specification danshen injections phenolic acid composition HPLC finger-print
Figure 42 50ml:12g specification danshen injections phenolic acid composition HPLC finger-print
Fig. 5 danshen injections carbohydrate hydrolysis HPLC schemes (1. mannose 2. glucose 3. galactoses)
Fig. 6 red sage root carbohydrate components nuclear-magnetism pulse sequence diagram
Fig. 7 red sage root carbohydrate components chemical shift figure
Fig. 8 red sage root carbohydrate components area integral figure
Embodiment
Below in conjunction with embodiment the quality control detection method based on component structure for danshen injections of the present invention is elaborated:
Embodiment
Quality control detection method step 1:
Measure the salvianolic acid content in the danshen injections, each phenolic acid composition is carried out qualitative, quantitative characterize
1. instrument:
Highly effective liquid phase chromatographic system: Agilent1100 U.S. Agilent Technologies (configuration vacuum degassing machine, automatic sampler, quaternary pump, VWD G1314A, DAD G1315B; Agilent ChemStation A10.02 chromatographic work station);
2. chromatographic condition
Chromatographic column: Shiseido Capcell pak MG C18 (4.6 * 250mm, 5 μ m) chromatographic column and Shiseido MG C18 guard column (4.6 * 12.5mm, 5 μ m); Flowing is acetonitrile (A)-0.075% phosphoric acid water mutually, and elution program is: acetonitrile (A) 0-17min, 5%A-12%A; 17-42min, 12%A-18%A; 42-46min, 18%A-18%A; 46-58min, 18%A-27%A; 58-65min, 27%A-27%A; 65-75min, 27%A-50%A; 75-85min, 50%A-80%A.Flow velocity is 1.0mL/min; The detection wavelength is 270nm; Column temperature is 30oC; Sampling volume is 10 μ L.
3. the preparation of reference substance solution:
Precision takes by weighing danshensu, protocatechualdehyde, caffeic acid, removes danshensu salvianolic acid E 1, removes danshensu salvianolic acid E 2, salviandic acid A, tanshin polyphenolic acid B, salvianolic acid C, salvianolic acid D, Rosmarinic acid totally 10 liposoluble ingredient reference substances:
Place the brown volumetric flask of 10ml respectively, add the methyl alcohol dissolving, be settled to 10ml, each reference substance concentration is followed successively by 100.53 μ g/ml, 95.60 μ g/ml, 85.49 μ g/ml, 74.26 μ g/ml, 58.62 μ g/ml, 120.36 μ g/ml, 57.18 μ g/ml, 66.21 μ g/ml, 59.78 μ g/ml, 117.64 μ g/ml.Respectively getting 1ml mixes to such an extent that mix reference substance solution.
4. experimental technique and result:
Get reference substance and danshen injections (250ml:16g and 250ml:12g specification) sample solution, analyze by chromatographic condition, measure danshensu, protocatechualdehyde, caffeic acid, remove danshensu salvianolic acid E 1, remove the peak area of danshensu salvianolic acid E 2, salviandic acid A, tanshin polyphenolic acid B, salvianolic acid C, salvianolic acid D, Rosmarinic acid, calculate total phenolic content in the danshen injections; Total phenolic acid and carbohydrate components, other component constituent ratios; Each composition constituent ratio in total phenolic acid.Concrete outcome is seen Fig. 2, Fig. 3 and Fig. 4, table 1, table 2, table 3.
Total phenolic content (250ml:16g) in table 1 danshen injections
Total phenolic content (250ml:12g) in table 2 danshen injections
The total phenolic acid of table 3 danshen injections and carbohydrate components, other component constituent ratios; Each composition constituent ratio in total phenolic acid
Quality control detection method step 2:
Carbohydrate content in the danshen injections is carried out qualitative, quantitative to be characterized.The HPLC chromatogram is seen Fig. 5.
1. instrument:
Highly effective liquid phase chromatographic system: Agilent1100 U.S. Agilent Technologies (configuration vacuum degassing machine, automatic sampler, quaternary pump, VWD G1314A, DAD G1315B; Agilent ChemStation A10.02 chromatographic work station);
2. chromatographic condition
Chromatographic column: Agilent Zorbax SB-C18(4.6 * 250mm, 5 μ m) chromatographic column and SB-C18(4.6 * 10mm, 5 μ m) guard column; Flow and carry out gradient elution: 1-25min for acetonitrile (A)-0.05M potassium dihydrogen phosphate aqueous solution mutually, 16.5%-16.5%A; 25-55min, 16.5%-24%A; 55-60min, 24%-24%A; Flow velocity: 1.0ml/min; Detect wavelength: 245nm; Column temperature: 45 ℃; Sample size: 10 μ l.
3. the preparation of standard solution
Get monose reference substance (the mannose 4.97mg/ml of new preparation, glucose 5.04mg/ml, galactose 5.16mg/ml) respectively 100 μ l are mixed must mix the monose reference substance, the NaOH solution 300 μ l that add 0.15M, mix, get 1-phenyl-3-methyl-5-pyrazolones ketone (PMP) the methanol solution 100 μ l that 100 μ l add 0.1M, be cooled to room temperature behind the reaction 30min in 70 ℃ of water-baths, the hydrochloric acid 100 μ l neutralization that adds 0.075M, add the methenyl choloride dissolving of water and the 1ml of 0.7ml, leave standstill behind the vortex 2min, carefully extract lower floor's methenyl choloride layer out with syringe after the layering, the residue water layer adds the vibration of 1ml methenyl choloride vortex again and mixes, and repeats above process 3 times.The most at last water layer with 0.45 μ m membrane filtration after, standby.
4. the preparation of sample solution
Get the 0.5ml danshen injections, add 0.5ml water, mixing, the NaOH solution 1ml that adds 0.15M, mixing, get 1-phenyl-3-methyl-5-pyrazolones ketone (PMP) the methanol solution 100 μ l that 100 μ l add 0.2M, be cooled to room temperature behind the reaction 30min in 70 ℃ of water-baths, the hydrochloric acid 100 μ l neutralization that adds 0.075M, add the methenyl choloride dissolving of water and the 1ml of 0.7ml, leave standstill behind the vortex 2min, carefully extract lower floor's methenyl choloride layer out with syringe after the layering, the residue water layer adds the vibration of 1ml methenyl choloride vortex again and mixes, and repeats above process 3 times.The most at last water layer with 0.45 μ m membrane filtration after, standby.
5. experimental technique and result:
Get reference substance and danshen injections sample solution, analyze by chromatographic condition, the peak area of each monose in the working sample solution, with mannose, glucose, the galactose reference substance compares, and calculates the content of carbohydrate components in the danshen injections.The results are shown in Table 4.
Table 4 carbohydrate content assay result
Quality control detection method step 3:
Adopt magnetic resonance NMR technology to the mensuration of carbohydrate components in the danshen injections solids
1. the preparation of sample
Damping fluid: 1.5M PBS, 0.05%TSP(g/100ml);
Need testing solution: the red sage root extracts solid 0.7948g and adds the 2ml distilled water, vortex, and centrifugal (not having precipitation) got supernatant 500ml and added the 50ml damping fluid, and mixing is namely.
2. instrument parameter setting
Nuclear-magnetism pulse-gFlipsy(Fig. 6)
Parameter arranges as follows:
3. computing formula
M
TSP: TSP molecular weight C
TSPThe volumetric molar concentration of TSP in the nuclear-magnetism pipe
4. compound belongs to and content
See Table 5, Fig. 7, Fig. 8.
Table 5 carbohydrate content magnetic resonance NMR measurement result
The inventor is through repeatedly experiment discovery, and the phenolic acid component in danshen injections: the content range of control of carbohydrate components is (1%-95%): (90%-1%); And danshensu, protocatechualdehyde, caffeic acid in the root of red-rooted salvia phenolic acid, remove danshensu salvianolic acid E 1, remove danshensu salvianolic acid E 2, the constituent ratio of salviandic acid A, tanshin polyphenolic acid B, salvianolic acid C, salvianolic acid D, each composition of Rosmarinic acid is respectively (1%-95%): (5%-95%): (1%-20%): (1%-20%): (5%-20%): (1%-50%): (5%-20%): (1%-10%): (1%-20%): (1%-20%); The content summation of phenolic acid component and carbohydrate components is greater than the 35-90% of total solid; When the phenolic acid components contents was not less than the 40-80% of total solid, the quality of this danshen injections was best.
Above embodiment is the Overall Steps of the quality control detection method of danshen injections of the present invention, and be index with composition danshensu and protocatechualdehyde only to the quality control of danshen injections at present, the mass action characteristics of the many active components performance drug effects that clearly contain in this and the danshen injections are disagreed, and also are unscientific Quality Control detection methods.Therefore, forming structure in the polycomponent of employing danshen injections of the present invention and the component is that the optimum detection standard that draws of the quality control detection method of danshen injections is more effective, scientific and reasonable.In existing open source literature report, mostly the relevant patent that is all danshen injections is at extraction process or preparation process, yet there are no the quality control whole detection method at the component structure feature of the present invention.
Claims (5)
1. the quality control detection method based on component of a danshen injections, concrete grammar is characterized by and adopts following concrete steps for structure and two aspects of each component inner structure between the component of total phenolic acid component and carbohydrate components in the danshen injections are detected control:
Measure concrete composition, ratio and the total phenolic content of interior each phenolic acid of salvianolic acid in the danshen injections;
Measure carbohydrate composition and content in the danshen injections;
Measure carbohydrate components and content in the danshen injections solids.
2. the quality control detection method based on component of danshen injections according to claim 1, it is characterized in that with danshensu, protocatechualdehyde, caffeic acid, remove danshensu salvianolic acid E 1, remove danshensu salvianolic acid E 2, salviandic acid A, tanshin polyphenolic acid B, salvianolic acid C, salvianolic acid D, Rosmarinic acid be reference substance, measures concrete composition, ratio and the total phenolic content of each phenolic acid in total phenolic acid with the HPLC chromatography.
3. the quality control detection method based on component of danshen injections according to claim 1 is characterized in that adopting mannose, and glucose, galactose are reference substance, measures carbohydrate with the HPLC chromatography and forms and content.
4. according to the quality control detection method based on component of the described danshen injections of claim 1, it is characterized in that adopting magnetic resonance NMR technology to measure composition and the content of the interior carbohydrate of solids in the parenteral solution.
5. according to the quality control detection method based on component of the described danshen injections of claim 1, it is characterized by the phenolic acid component in this parenteral solution: the content range of control of carbohydrate components is (1%-95%): (90%-1%); And danshensu, protocatechualdehyde, caffeic acid in the root of red-rooted salvia phenolic acid, remove danshensu salvianolic acid E 1, remove danshensu salvianolic acid E 2, the constituent ratio of salviandic acid A, tanshin polyphenolic acid B, salvianolic acid C, salvianolic acid D, each composition of Rosmarinic acid is respectively (1%-95%): (5%-95%): (1%-20%): (1%-20%): (5%-20%): (1%-50%): (5%-20%): (1%-10%): (1%-20%): (1%-20%); The content summation of phenolic acid component and carbohydrate components is greater than the 35-90% of total solid; The phenolic acid components contents is not less than this parenteral solution of 40-80% the best in quality of total solid.
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| CN107014853A (en) * | 2017-02-22 | 2017-08-04 | 天津中医药大学 | A kind of detection method of content of sodium tashinone II A sulfonate injection |
| CN115403653A (en) * | 2022-05-19 | 2022-11-29 | 首都医科大学 | D (+) -beta- (3, 4-dihydroxyphenyl) -lactyl-Pro-Ala-Lys, synthesis and application thereof |
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