CN102119957A - Preparation method and application of effective ingredient of rosewood heart wood - Google Patents
Preparation method and application of effective ingredient of rosewood heart wood Download PDFInfo
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- CN102119957A CN102119957A CN 201110058973 CN201110058973A CN102119957A CN 102119957 A CN102119957 A CN 102119957A CN 201110058973 CN201110058973 CN 201110058973 CN 201110058973 A CN201110058973 A CN 201110058973A CN 102119957 A CN102119957 A CN 102119957A
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- dalbergiae odoriferae
- lignum dalbergiae
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides an effective ingredient of rosewood heart wood. The effective ingredient mainly comprises isoliquiritigenin, medicarpin, dalbergin and 3'-methoxy violanone and is obtained by the following steps of: heating medicinal materials and extracting; concentrating, separating by using a silicagel column, eluting, concentrating eluent and drying; and continuously separating by using a liquid chromatogram, collecting solution, concentrating the collected solution and drying. The effective ingredient of the rosewood heart wood provided by the invention can be applied to the preparation of a medicament for treating and preventing cardiovascular disease. The method has a reasonable design and can be used for quickly and accurately obtaining the effective ingredient; and by the method, the quality of the medicament is easier to control during production.
Description
Technical field
The invention belongs to the Chinese medicine extract field, relate to a kind of Chinese medicine extract for the treatment of cardiovascular disease, relate in particular to the preparation method and the purposes of the active component that extracts from Lignum Dalbergiae Odoriferae, this active component mainly contains several chemical compounds such as the purple dalbergin of isoliquiritigenin, (-)-3-hydroxy-9-methoxypterocarpan, dalbergin and 3'-methoxyl group.
Background technology
Cardiovascular disease is first killer of harm humans health, in recent years, along with the variation of China's population senescence and people's work, life, dietary structure and environment etc., the incidence rate of cardiovascular and cerebrovascular diseases such as coronary heart disease also increases year by year, and the people's physical and mental health in serious threat.In the natural product many active substances have resist myocardial ischemia, anoxia functions, some of them have been developed to treatment coronary heart disease and anginal new drug.Thereby from natural product, seek have resist myocardial ischemia, the active substance of anoxia physiologically active, be find, one of effective way of developing new drug.China's medicinal organism resource is very abundant, and its biological active substances is research and finds new drug guide chemicals, the natural treasure-house of developing new drug.At present, China extracts active substance from natural product, be used to be developed to treatment coronary heart disease, safety is good, toxicity is low new drug also seldom, from natural product, extract active substance, be developed to have and resist myocardial ischemia, be used for the treatment of coronary heart disease and anginal new drug, have significant application value and wide development prospect.
Lignum Dalbergiae Odoriferae is the dry duramen of leguminous plant Lignum Dalbergiae Odoriferae wingceltis Dalbergia odorifera T. Chen trunk and root.Suffering, temperature is returned liver, spleen channel.Have promoting flow of QI and blood, pain relieving, the hemostatic effect contains multiple flavones ingredient, belongs to having of isoflavone: formoononetin, Bao Di xyloquinone, the big legumin of 3'-methoxyl group; Belong to having of flavanone: liquiritigenin; Belong to having of chalcone derivative: isoliquiritin unit, 2'-O-methyl isoliquiritin unit; Belong to having of isoflavan: (3R)-donkey food grass phenol, 5'-methoxyl group donkey food grass phenol, 3', 8-dihydroxy donkey food grass phenol, dimpling sword-like leave Sha phenol of racemization, dextral sword-like leave Sha belongs to isoflavan, and different sword-like leave Sha of racemization belongs to isoflavan, the different yellow alkene of Lignum Dalbergiae Odoriferae; Belong to having of isoflavanone: (3R)-2', 3'-7-trihydroxy-4'-methoxyl group isoflavanone.Also contain two isoflavan constituents: (3R, 4R)-trans-2', 3', 7-trihydroxy-4'-Shen oxygen base-4[(3R)-2', 7-dihydroxy-4'-methoxyl group isoflavan-5'-yl] isoflavan, (3R, 4R)-and trans 2', 7-dihydroxy-4'-methoxyl group-4-[(3R)-and 2', 7-dihydroxy-4'-methoxyl group isoflavan-5'-yl] isoflavan, (3R, 4R)-trans-3' under, 7-dihydroxy-2', 4'-dimethoxy-4 ' [(3R) 2', 7-dihydroxy-4'-methoxyl group isoflavan-5'-yl] isoflavan, 7-hydroxyl-4'-methoxyl group-2', the 5'-dioxy-4-[(3R)-and 2', 7-dihydroxy-4'-methoxyl group isoflavan-5'-yl) isoflavan, (3R, 4R)-and trans-3', 7-dihydroxy-2', the 4'-dimethoxy-4 '-[(2S)-4', 5,7-trihydroxy flavanone-6-yl] isoflavan, 2,3-two deoxidations-2', 7-dihydroxy-4'-methoxyl group-3-[2', 7-dihydroxy-4'-methoxyl group isoflavan-6-yl] flavane, 2,3-two deoxidations-2', 7-dihydroxy-4'-methoxyl group-3-[2', 7-dihydroxy-4'-methoxyl group isoflavan-5' yl] flavane, 2,3-two deoxidations-2', 7-dihydroxy-4'-methoxyl group-3-(2', 7-dihydroxy-4'-methoxyl group isoflavan-5' yl) flavone.Contain the pterocarpan composition again: (-)-3-hydroxy-9-methoxypterocarpan, left-handed 9-O-methyl Unisem sweet pea Lignum pterocarpi indici phenol, left-handed white sweet clover Lignum pterocarpi indici phenol C and D, left-handed season perfume pterocarpin.Also contain cinnamyl phenol composition: dalbergia obtusifolia styrene, different dimpling sword-like leave Sha styrene.Contain 2-hydroxyl-3 again, 4-dimethoxy p-methyl, 2', 6-dihydroxy-4'-methoxyl group-2-aryl benzofuran.
Lignum Dalbergiae Odoriferae is a promoting blood circulation to remove blood stasis Chinese medicine, experiment shows that its syndrome of blood stasis animal capable that high molecular dextran is injected formed blood high viscosity syndrome significantly reduces whole blood viscosity, especially the whole blood viscosity effect is outstanding under the high shear rate to reduce, also can reduce plasma viscosity, but erythrocyte aggregation is not made significant difference, Lignum Dalbergiae Odoriferae also has the blood fat reducing effect, and it reduces syndrome of blood stasis animal blood viscosity may be relevant with its effect for reducing fat, and the mechanism of its effect for reducing blood fat is then with to suppress the HMG CoA-reductase relevant.2-hydroxyl-3,4-dimethoxy p-methyl, hydroxyl dalbergia obtusifolia styrene, different dimpling sword-like leave Sha styrene have test to show significantly anticoagulant of contained some composition in addition.In addition, Lignum Dalbergiae Odoriferae is that coronary disease II number side forms one of medicine, the modern pharmacology experiment shows that the single Lignum Dalbergiae Odoriferae can significantly promote recovery and the recovery after the arteriole contraction and the recovery of local microcirculation of the experimental microcirculation disturbance blood flow of mice mesentery, arteriolar contraction is stronger due to its antiadrenergic drug, to a little less than postponing the effect that blood arrheas.The remarkable hypotensive effect of coronary disease II tool, wherein Lignum Dalbergiae Odoriferae plays a role because of the receptor of inhibition angiotensin II.Lignum Dalbergiae Odoriferae has above obvious pharmacological action to cardiovascular system, therefore, isolates active component from Lignum Dalbergiae Odoriferae, and the modern Chinese medicine of developing the treatment cardiovascular disease has great importance.
Summary of the invention
The object of the present invention is to provide a kind of preparation method of Lignum Dalbergiae Odoriferae active component, realize by following steps: will add ethyl acetate and ethanol after the Lignum Dalbergiae Odoriferae pulverizing medicinal materials, heating extraction, medicinal residues add ethanol water and extract, extracting solution is condensed into extractum, with the reverse phase silica gel post it is separated, at first use low concentration methanol, get eluent I as mobile phase, abandon it, use high concentration methanol then instead as mobile phase, get eluent II, will get sample behind the eluent II concentrate drying; Continue to separate the sample that obtains with preparative liquid chromatography; The separation condition of preparative hplc: chromatographic column is a preparative column, and mobile phase is water and acetonitrile, gradient elution.
Preferably, Lignum Dalbergiae Odoriferae active component preparation method of the present invention comprises the following steps: to get the Lignum Dalbergiae Odoriferae medical material, and it is pulverized the back, and to add volume ratio be ethyl acetate and the ethanol of 1:1, and reflux 1 hour is extracted 2 times, filtrate merge extracting solution I.Medicinal residues add 70% ethanol, and reflux 1 hour is extracted 2 times, filtrate merge extracting solution II, II is condensed into extractum with extracting solution, with 50% dissolve with methanol extractum, adopts ODS-C
18Post separates it, at first uses 5% methanol as mobile phase, gets eluent I, uses 70% methanol then instead as mobile phase, gets eluent II, gets sample behind the concentrate drying; Continue to separate the sample that obtains with preparative liquid chromatography: the separation condition of preparative hplc: chromatographic column is preparative column (ZORBAX Sb-C
18; 21.2mm
250mm, 7
), mobile phase is water A and acetonitrile B, the gradient elution program is as follows: during 0min, mobile phase A is 85% water, and Mobile phase B is 15% acetonitrile solution; During 60min, mobile phase A is 40% water, and Mobile phase B is 60% acetonitrile solution; Flow velocity is 10ml/min, and column temperature is a room temperature; Sample separates through preparative liquid chromatography, collects solution in the 48.2-53.8min time period, and solution obtains active component behind concentrate drying, mainly contains the purple dalbergin of isoliquiritigenin, Sativanone, dalbergin and 3'-methoxyl group.
Another object of the present invention provides the application of the above-mentioned Lignum Dalbergiae Odoriferae active component for preparing in the medicine of preparation treatment, angiocardiopathy preventing.Prove that through pharmacological evaluation Lignum Dalbergiae Odoriferae active component provided by the invention has the certain protection effect to myocardial cell.
Lignum Dalbergiae Odoriferae active component of the present invention can be used as active component, adds the adjuvant of accepting on the pharmaceutics, makes preparation according to the preparation method of the preparation of putting down in writing on the pharmaceutics.
Described preparation comprises injection, drip liquid, injectable powder, granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, enteric coated tablet, capsule, hard capsule, soft capsule, sucks agent, granule, pill, unguentum, sublimed preparation, spray, drop pill, disintegrating agent, oral cavity disintegration tablet, micropill etc.
Lignum Dalbergiae Odoriferae active component of the present invention and preparation thereof can be used in preparation treatment, angiocardiopathy preventing medicine.Preparation method provided by the invention is reasonable in design, can obtain effective ingredient rapidly and accurately, is easier to the quality control of medicine aborning.
Description of drawings
Fig. 1 is the HPLC chromatogram of Lignum Dalbergiae Odoriferae active component, and 1 is isoliquiritigenin, and 2 is Sativanone, and 3 is dalbergin, and 4 is the purple dalbergin of 3-methoxyl group.
The specific embodiment
Further describe flesh and blood of the present invention and beneficial effect below in conjunction with embodiment, this embodiment only is used to the present invention is described but not limitation of the present invention.
The preparation of embodiment one Lignum Dalbergiae Odoriferae active component
To add ethyl acetate and ethanol after the Lignum Dalbergiae Odoriferae pulverizing medicinal materials, heating extraction gets extracting solution I, abandons it.Medicinal residues add ethanol water, and heating extraction gets extracting solution II, and II is condensed into extractum with extracting solution, with 50% dissolve with methanol extractum, adopt ODS-C
18Post separates it, at first uses low concentration methanol as mobile phase, gets eluent I, uses high concentration methanol then instead as mobile phase, gets eluent II, gets sample behind the concentrate drying; Continue to separate the sample that obtains with preparative liquid chromatography, separate, collect solution, obtain active component behind the concentrate drying at time period 48.2-53.8min through preparative liquid chromatography.
The preparation of embodiment two Lignum Dalbergiae Odoriferae active components
Get Lignum Dalbergiae Odoriferae medical material 250g, it is pulverized the back, and to add volume ratio be ethyl acetate and the ethanol of 1:1, and reflux 1 hour is extracted 2 times, filtrate merge extracting solution I.Medicinal residues add 70% alcoholic solution, and reflux 1 hour is extracted 2 times, filtrate merge extracting solution II, II is condensed into extractum with extracting solution, with 50% dissolve with methanol solution extractum, adopts ODS-C
18Post separates it, at first uses 5% methanol solution as mobile phase, gets eluent I, uses 70% methanol solution then instead as mobile phase, gets eluent II, gets sample behind the concentrate drying; Continue to separate the sample that obtains with preparative liquid chromatography: the separation condition of preparative hplc: chromatographic column is preparative column (ZORBAX Sb-C
18; 21.2mm
250mm, 7
), mobile phase is water A and acetonitrile B, the gradient elution program is as follows: during 0min, mobile phase A is 85% water, and Mobile phase B is 15% acetonitrile solution; During 60min, mobile phase A is 40% water, and Mobile phase B is 60% acetonitrile solution; Flow velocity is 10ml/min, and column temperature is a room temperature; Sample separates through preparative liquid chromatography, collects solution at time period 48.2-53.8min, and solution obtains active component behind concentrate drying.Mainly contain the purple dalbergin of isoliquiritigenin, Sativanone, dalbergin and 3'-methoxyl group.
The analysis of embodiment three Lignum Dalbergiae Odoriferae active components
Chromatographic condition: chromatographic column Agilent Zorbax SB-C
18Post (4.6
Mm* 150
Mm, 5
μ m); Adopt gradient elution, mobile phase A is 0.2% glacial acetic acid aqueous solution mutually, and Mobile phase B is mutually for containing the acetonitrile solution of 0.2% glacial acetic acid; The gradient elution program is as follows: in the time of 0 minute, mobile phase A is that 90% 0.2% glacial acetic acid aqueous solution, Mobile phase B are the acetonitrile solution of 10% 0.2% glacial acetic acid; In the time of 20 minutes, mobile phase A is that 70% 0.2% glacial acetic acid aqueous solution, Mobile phase B are the acetonitrile solution of 30% 0.2% glacial acetic acid; In the time of 30 minutes, mobile phase A is that 50% 0.2% glacial acetic acid aqueous solution, Mobile phase B are the acetonitrile solution of 50% 0.2% glacial acetic acid; In the time of 35 minutes, mobile phase A is that 50% 0.2% glacial acetic acid aqueous solution, Mobile phase B are the acetonitrile solution of 50% 0.2% glacial acetic acid; Flow velocity 0.5mL/min; Detect wavelength: 254 nm; 30 ℃ of column temperatures; Sample size 5 μ L.Chromatogram is seen Fig. 1, mainly contains the purple dalbergin of isoliquiritigenin, Sativanone, dalbergin and 3'-methoxyl group.
The preparation of need testing solutionTake by weighing this product, in volumetric flask, be diluted to scale, shake up, promptly with dissolve with methanol solution.
Assay methodThe accurate need testing solution of drawing injects chromatograph of liquid, measures, promptly.
The preparation of embodiment four dropping pill formulations
Get Lignum Dalbergiae Odoriferae active component 0.5g and 10.5g Polyethylene Glycol-20000 mix homogeneously, heating and melting moves in the drop pill drip irrigation behind the change material, and in ℃ liquid paraffin of medicine liquid droplet to 6 ~ 8, oil removing makes 400 of drop pill.
The preparation of embodiment five lyophilized injectable powders
Get Lignum Dalbergiae Odoriferae active component 0.5g, glucose 4.5g, sodium thiosulfate 0.9g and distilled water 1000ml, behind the said components mix homogeneously, 400 of packing, lyophilization, promptly.
The active appraisal experiment of embodiment six Lignum Dalbergiae Odoriferae active components
1. the Lignum Dalbergiae Odoriferae component is to H
2O
2The protective effect of injury of myocardium cell
In vitro culture H
9C
2Myocardial cell, culture fluid are that DMEM (high sugar)+10%FBS (G)+1% non essential amino acid+0.1% pair is anti-.The trophophase cell of taking the logarithm places on the 96 porocyte culture plates, behind constant temperature culture 24 h, adds 200 μ mol/mL H
2O
2Injury of myocardium cell 30 min, the Lignum Dalbergiae Odoriferae component that adds final concentration again and be 50 μ g/mL is hatched 24 h, adopts mtt assay to measure cell viability.The result shows that this component is to H
2O
2The protective rate of injury of myocardium cell is 18.5 %.
2. the Lignum Dalbergiae Odoriferae component is to the protective effect of hypoxia-reoxygenation induced injured myocardium cell
In vitro culture H
9C
2Myocardial cell, culture fluid are that DMEM (high sugar)+10%FBS (G)+1% non essential amino acid+0.1% pair is anti-.The trophophase cell of taking the logarithm places on the 96 porocyte culture plates, behind constant temperature culture 24 h, cultivates 6 h in the anoxia cell.After anoxia finished, taking out the Tissue Culture Plate adding was the Lignum Dalbergiae Odoriferae component of 50 μ g/mL through the final concentration of sugar-free Hank ' s dilution, is hatching 6 h under normal condition of culture, gets cell culture supernatant and measures lactic acid dehydrogenase (LDH) content.The result shows that this component is 21.6 % to the myocardial cell protection rate of anoxia reoxygenation injury.
Claims (5)
1. a Lignum Dalbergiae Odoriferae active component is characterized in that, obtains by following steps: will add ethyl acetate and ethanol after the Lignum Dalbergiae Odoriferae pulverizing medicinal materials, heating extraction, medicinal residues add ethanol water and extract, and extracting solution is condensed into extractum, with the reverse phase silica gel post it are separated, at first use low concentration methanol as mobile phase, get eluent I, abandon it, use high concentration methanol then instead as mobile phase, get eluent II, will get sample behind the eluent II concentrate drying; Continue to separate the sample that obtains with preparative liquid chromatography; The separation condition of preparative hplc: chromatographic column is a preparative column, and mobile phase is water and acetonitrile, gradient elution; Collect solution, solution obtains active component behind concentrate drying, mainly contains the purple dalbergin of isoliquiritigenin, Sativanone, dalbergin and 3'-methoxyl group in this active component.
2. a kind of Lignum Dalbergiae Odoriferae active component according to claim 1 is characterized in that low concentration methanol is 5% methanol solution, the methanol solution of high concentration methanol 70%.
3. a kind of Lignum Dalbergiae Odoriferae active component according to claim 1 is characterized in that, obtains by following steps: get the Lignum Dalbergiae Odoriferae medical material, it is pulverized back adding volume ratio is ethyl acetate and the ethanol of 1:1, reflux 1 hour is extracted 2 times, filtrate merge extracting solution I; Medicinal residues add 70% ethanol, and reflux 1 hour is extracted 2 times, filtrate merge extracting solution II, II is condensed into extractum with extracting solution, with 50% dissolve with methanol extractum, adopts ODS-C
18Post separates it, at first uses 5% methanol as mobile phase, gets eluent I, uses 70% methanol then instead as mobile phase, gets eluent II, gets sample behind the concentrate drying; Continue to separate the sample that obtains with preparative liquid chromatography: the separation condition of preparative hplc: chromatographic column is preparative column (ZORBAX Sb-C
18; 21.2mm
250mm, 7
), mobile phase is water A and acetonitrile B, the gradient elution program is as follows: 0min, 15%B; 60min, 60%B; Flow velocity is 10ml/min, and column temperature is a room temperature; Sample separates through preparative liquid chromatography, collects solution in the 48.2-53.8min time period, and solution obtains active component behind concentrate drying;
The application in the medicine of preparation treatment cardiovascular disease according to claim 1 or 3 described a kind of Lignum Dalbergiae Odoriferae active components.
4. application according to claim 4 is characterized in that, described medicine adds acceptable auxiliary on the pharmaceutics by the Lignum Dalbergiae Odoriferae active component, makes according to the formulation preparation method of putting down in writing on the pharmaceutics.
5. application according to claim 5 is characterized in that described preparation comprises liquid preparation or solid preparation.
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| CN1375316A (en) * | 2002-02-07 | 2002-10-23 | 天津天士力制药股份有限公司 | Chinese medicine prepn. for treating coronary heart disease and angina pactoris and its prepn. process |
| CN1559469A (en) * | 2004-02-27 | 2005-01-05 | 北京乾露春科技有限公司 | Prepn. method for freezing-drying powder injection for treating cardiovascular disease |
| CN101450106A (en) * | 2008-12-25 | 2009-06-10 | 浙江大学 | Traditional Chinese medicine composition with ischemic myocardium angiogenesis promoting function |
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| CN1375316A (en) * | 2002-02-07 | 2002-10-23 | 天津天士力制药股份有限公司 | Chinese medicine prepn. for treating coronary heart disease and angina pactoris and its prepn. process |
| CN1559469A (en) * | 2004-02-27 | 2005-01-05 | 北京乾露春科技有限公司 | Prepn. method for freezing-drying powder injection for treating cardiovascular disease |
| CN101450106A (en) * | 2008-12-25 | 2009-06-10 | 浙江大学 | Traditional Chinese medicine composition with ischemic myocardium angiogenesis promoting function |
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| CN111773265A (en) * | 2020-08-11 | 2020-10-16 | 江西中医药大学 | Application of dalbergia odorifera leaf extract in preparation of medicines for preventing or treating osteoporosis |
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