CN101348474A - Method for preparing salvianolic acid B and tanshinol from Salvia miltiorrhiza stem - Google Patents
Method for preparing salvianolic acid B and tanshinol from Salvia miltiorrhiza stem Download PDFInfo
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- CN101348474A CN101348474A CNA2007100183021A CN200710018302A CN101348474A CN 101348474 A CN101348474 A CN 101348474A CN A2007100183021 A CNA2007100183021 A CN A2007100183021A CN 200710018302 A CN200710018302 A CN 200710018302A CN 101348474 A CN101348474 A CN 101348474A
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- salvianolic acid
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- salvianic acida
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- SNKFFCBZYFGCQN-UHFFFAOYSA-N 2-[3-[3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyloxy]-3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound C=1C=C(O)C=2OC(C=3C=C(O)C(O)=CC=3)C(C(=O)OC(CC=3C=C(O)C(O)=CC=3)C(O)=O)C=2C=1C=CC(=O)OC(C(=O)O)CC1=CC=C(O)C(O)=C1 SNKFFCBZYFGCQN-UHFFFAOYSA-N 0.000 title claims abstract description 20
- SNKFFCBZYFGCQN-VWUOOIFGSA-N Lithospermic acid B Natural products C([C@H](C(=O)O)OC(=O)\C=C\C=1C=2[C@H](C(=O)O[C@H](CC=3C=C(O)C(O)=CC=3)C(O)=O)[C@H](OC=2C(O)=CC=1)C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 SNKFFCBZYFGCQN-VWUOOIFGSA-N 0.000 title claims abstract description 19
- STCJJTBMWHMRCD-UHFFFAOYSA-N salvianolic acid B Natural products OC(=O)C(Cc1ccc(O)c(O)c1)OC(=O)C=Cc2cc(O)c(O)c3OC(C(C(=O)OC(Cc4ccc(O)c(O)c4)C(=O)O)c23)c5ccc(O)c(O)c5 STCJJTBMWHMRCD-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 17
- 229930189533 tanshinol Natural products 0.000 title abstract 4
- 241000304195 Salvia miltiorrhiza Species 0.000 title 1
- 235000011135 Salvia miltiorrhiza Nutrition 0.000 title 1
- 239000011347 resin Substances 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 238000005057 refrigeration Methods 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000003809 water extraction Methods 0.000 claims abstract description 4
- 239000000284 extract Substances 0.000 claims abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 240000007164 Salvia officinalis Species 0.000 claims description 17
- 235000005412 red sage Nutrition 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 4
- PAFLSMZLRSPALU-MRVPVSSYSA-N (2R)-3-(3,4-dihydroxyphenyl)lactic acid Chemical compound OC(=O)[C@H](O)CC1=CC=C(O)C(O)=C1 PAFLSMZLRSPALU-MRVPVSSYSA-N 0.000 claims description 3
- PAFLSMZLRSPALU-UHFFFAOYSA-N Salvianic acid A Natural products OC(=O)C(O)CC1=CC=C(O)C(O)=C1 PAFLSMZLRSPALU-UHFFFAOYSA-N 0.000 claims description 3
- 229930002875 chlorophyll Natural products 0.000 claims description 3
- 235000019804 chlorophyll Nutrition 0.000 claims description 3
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 3
- 238000007654 immersion Methods 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- YMGFTDKNIWPMGF-QHCPKHFHSA-N Salvianolic acid A Natural products OC(=O)[C@H](Cc1ccc(O)c(O)c1)OC(=O)C=Cc2ccc(O)c(O)c2C=Cc3ccc(O)c(O)c3 YMGFTDKNIWPMGF-QHCPKHFHSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 4
- YMGFTDKNIWPMGF-UCPJVGPRSA-N Salvianolic acid A Chemical compound C([C@H](C(=O)O)OC(=O)\C=C\C=1C(=C(O)C(O)=CC=1)\C=C\C=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 YMGFTDKNIWPMGF-UCPJVGPRSA-N 0.000 claims 1
- 230000000274 adsorptive effect Effects 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 229930183842 salvianolic acid Natural products 0.000 claims 1
- 238000001694 spray drying Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 238000001291 vacuum drying Methods 0.000 abstract description 3
- 238000005507 spraying Methods 0.000 abstract description 2
- 238000005119 centrifugation Methods 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000010828 elution Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- PAFLSMZLRSPALU-QMMMGPOBSA-N Danshensu Natural products OC(=O)[C@@H](O)CC1=CC=C(O)C(O)=C1 PAFLSMZLRSPALU-QMMMGPOBSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 1
- YMGFTDKNIWPMGF-AGYDPFETSA-N 3-(3,4-dihydroxyphenyl)-2-[(e)-3-[2-[(e)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]prop-2-enoyl]oxypropanoic acid Chemical compound C=1C=C(O)C(O)=C(\C=C\C=2C=C(O)C(O)=CC=2)C=1/C=C/C(=O)OC(C(=O)O)CC1=CC=C(O)C(O)=C1 YMGFTDKNIWPMGF-AGYDPFETSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- -1 Salvianic acidA Chemical compound 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000003035 anti-peroxidant effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses a method for simultaneously separating tanshinol and salvianolic acid B from leaves and stems of radix salivae miltiorrhizae. The method comprises the following steps of 1. water extraction; 2. refrigeration, centrifugation or filtration; 3 adjustment of pH of the extract; 4. separation of tanshinol from salvianolic acid B with a large-hole adsorption resin and; 5 vacuum drying or spraying drying. The method provided by the invention can simultaneously extract and purify tanshinol and salvianolic acid B with high content and take full advantages of the medicinal material of radix salivae miltiorrhizae, has low cost and stable quality of the product, and allows for large-scale production.
Description
Technical field
The present invention relates to a kind of method that from red sage root cauline leaf, prepares salvianolic acid B and Salvianic acidA.
Background technology
The red sage root is used as medicine with root, and more its cauline leaf is abandoned and need not.In order to make full use of the top drug resource of the red sage root, by the HPLC method salvianolic acid B in the 6～October pale reddish brown red sage root cauline leaf and content of Danshensu measurement result are shown, these two kinds of liposoluble ingredient content reach the highest in July, wherein content of Danshensu is than exceeding in the red sage root more than one times, and cauline leaf also contains unexistent phenol thing in the red sage root.Find no any toxic side effect in the clinical use.For reducing production costs, improve yield, can consider to replace red sage root as the raw material of producing medicaments for coronary disease with red sage root cauline leaf, water soluble component comprises in the red sage root cauline leaf: rancinamycin IV, Salvianic acidA, Protocatechuic Acid and salvianolic acid A, B, C, D, E etc., wherein remarkable with the effect of Salvianic acidA and salvianolic acid B, it has significant anti peroxidation of lipid, removes free radical and antithrombotic effect.Cardiovascular disorder is the elderly's height morbidity, the developing the salvianolic acid B series product and will do and provide big contribution for the mankind prevent and treat cardiovascular diseases of success.
The method that from red sage root cauline leaf, prepares salvianolic acid B and Salvianic acidA that the present invention proposes, its technical scheme is:
1, water extraction
Adopt 50 ℃～60 ℃ deionized water to soak, select for use twice effect of immersion better.Soak for the first time, get the red sage root cauline leaf that crushes, amount of water is generally 10～15 times of medicinal material amount, is heated to 50 ℃～60 ℃ insulations and soaks 10～12 hours, separates extracting solution for the first time.Soak for the second time, amount of water is 8～12 times of medicinal material amount, 50 ℃～60 ℃ insulations 8～10 hours, separates extracting solution for the second time.Water logging bubble with 50 ℃～60 ℃ can be avoided the content of danshinolic acid B loss.
2, refrigeration, filtration
Merge extracted twice liquid,, can remove solid impurities such as some chlorophyll with the filter paper sheet frame 4 ℃～10 ℃ refrigerations 24 hours.
3, extracting solution is transferred pH value
Extracting solution is transferred PH3～4 with 10% hydrochloric acid or sulfuric acid, because salvianolic acid B and Salvianic acidA are slightly acidic class material, it easily by absorption with macroporous adsorbent resin, improves the separation and purification effect under acidic conditions.
4, macroporous adsorbent resin separation, purifying salvianolic acid B and Salvianic acidA
(1) activation of resin column can be adopted methyl alcohol, ethanol, alkali-aqueous solution or acid-aqueous solution.
(2) aqueous solution with the above-mentioned red sage root adds on the resin column of having handled well, with liquor ferri trichloridi differentiate whether go up saturated, if differentiate present blackish green, sample on then stopping.
(3) it is 1.15～1.18 that water wash-out Salvianic acidA, water lotion are evaporated to proportion, uses ethyl acetate extraction 4～5 times, and each dosage is 2～3 times of washing concentrated solution volume, and extraction liquid merges can purer Salvianic acidA.
(4) with 40%～70% ethanol elution salvianolic acid B, elution amount is 7～9 times of volumes.
5, drying
It is 1.20～1.24 that alcohol eluen and extraction liquid are concentrated into proportion respectively, adopts vacuum-drying or spraying drying, can get high-purity danshinolic acid B and Salvianic acidA.
Specific implementation method:
Below in conjunction with specific embodiment, the present invention is described in further detail.
Embodiment one:
1, water extraction: get red sage root cauline leaf 10kg, pulverize, add the water of 12 times of amounts by weight, at 55 ℃ of insulations 10 hours, separation and Extraction liquid; Residue adds water by 8 times of amounts of former cauline leaf weight, and 60 ℃ are incubated 8 hours, and separation and Extraction liquid merges extracted twice liquid.Refrigeration, filtration.Extracting solution is used filter paper filtering 6 ℃ of refrigerations 24 hours.
2, extracting solution is transferred pH value: add 10% hydrochloric acid and transfer PH in filtrate, the limit edged stirs, to the PH of filtrate be 3.5.
3, D301 type (Chemical Plant of Nankai Univ.'s product) resin column on the filtrate, weight resin is 5kg.With liquor ferri trichloridi differentiate whether go up saturated, water wash-out Salvianic acidA, about 10 times of amount volumes, water elution liquid is concentrated into proportion 1.16, with ethyl acetate extraction 4 times, dosage is spissated 2 times of amounts at every turn, uses 50% ethanol elution salvianolic acid B again.
4, drying: reclaim under reduced pressure acetic acid ethyl acetate extract, dry 152g content are 75.3% Salvianic acidA, 50% ethanol eluate reclaim under reduced pressure vacuum-drying 210g, 82% salvianolic acid B.
Embodiment two:
Basic identical with embodiment one, different is that leaching process is 100 ℃ of decoctions of water.
Embodiment three:
Basic identical with embodiment one, different is, and what to extract that the extracting solution acidifying uses is sulfuric acid.
Embodiment four:
Basic identical with embodiment one, usefulness that different is be 70% ethanol elution salvianolic acid B.
Claims (5)
1, a kind of method that from red sage root cauline leaf, prepares salvianolic acid B and Salvianic acidA, its processing step is:
Step 1, water extraction
Take from and so dry or after drying in the sun red sage root cauline leaf pulverized, water decocted or the warm water immersion method extracts main soluble salvianolic acid constituents.
Step 2, refrigeration, centrifugal or filtration
Adopt refrigeration 24 hours, centrifugal or filter the solid impurity tentatively removed in the extracting solution and chlorophyll etc.
Step 3, acidizing extracting liquid
Add mineral acid and transfer pH value in extracting solution, the PH that makes extracting solution is 3～4.
Step 4, macroporous adsorbent resin separate Salvianic acidA and salvianolic acid B
The employing macroporous adsorptive resins separates, and chromatographic column should activate earlier, then extracting solution is added to chromatographic column, and water wash-out Salvianic acidA, water lotion can get high-purity salvianic acid A again through ethyl acetate extraction.
With alcohol-water solution or second eyeball-aqueous solution wash-out, get highly purified salvianolic acid B solution.
Step 5, drying.
2, the described preparation method of claim 1 is characterized in that: it can be decocting method that red sage root cauline leaf is pulverized the method for extracting the back, also available warm water immersion method, and with refrigeration, centrifugal or filtration method is removed the impurity such as chlorophyll in the extracting solution.
3, claim 1 or 2 described preparation methods is characterized in that: step 3, acidizing extracting liquid, and acid is hydrochloric acid or sulfuric acid, regulating and making its PH is 3～4.
4, claim 1 or 2 described preparation methods, it is characterized in that: step 4, macroporous adsorbent resin separate, and first water wash-out Salvianic acidA is after water lotion concentrates ethyl acetate extraction, can get the Salvianic acidA more than 70%, get salvianolic acid B with low or height alcoholic solution wash-out again.
5, claim 1 or 2 described preparation methods is characterized in that: step 5, employing boulton process or spray-drying process.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100183021A CN101348474A (en) | 2007-07-20 | 2007-07-20 | Method for preparing salvianolic acid B and tanshinol from Salvia miltiorrhiza stem |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100183021A CN101348474A (en) | 2007-07-20 | 2007-07-20 | Method for preparing salvianolic acid B and tanshinol from Salvia miltiorrhiza stem |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101348474A true CN101348474A (en) | 2009-01-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007100183021A Pending CN101348474A (en) | 2007-07-20 | 2007-07-20 | Method for preparing salvianolic acid B and tanshinol from Salvia miltiorrhiza stem |
Country Status (1)
| Country | Link |
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| CN (1) | CN101348474A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102028743A (en) * | 2009-09-29 | 2011-04-27 | 天津天士力现代中药资源有限公司 | Medicament for treating coronary heart disease and preparation method thereof |
| CN102028746A (en) * | 2009-09-29 | 2011-04-27 | 天津天士力现代中药资源有限公司 | Drug for treating coronary heart disease and extraction method |
| CN102690193A (en) * | 2012-03-28 | 2012-09-26 | 西安鸿生生物技术有限公司 | Preparation technology of tanshinol using spray counterflow extraction method |
| CN104611373A (en) * | 2015-02-10 | 2015-05-13 | 南京中医药大学 | Method for efficiently preparing salvianolic acid components from overground stems and leaves of salviae miltiorrhizae employing bioconversion technology |
| CN104761520A (en) * | 2015-04-10 | 2015-07-08 | 大连工业大学 | Method for preparing high-purity salvianolic acid B employing salt precipitation |
| CN106690317A (en) * | 2016-11-11 | 2017-05-24 | 贵州黔贵天赐大健康集团有限公司 | Radix salviae miltiorrhizae composition and preparation method thereof |
| CN106995369A (en) * | 2017-03-31 | 2017-08-01 | 吉林四长制药有限公司 | A kind of preparation method using danshensu as the red sage root extract of object |
| CN110423230A (en) * | 2019-08-07 | 2019-11-08 | 南阳医学高等专科学校 | A method of tanshin polyphenolic acid B is extracted from Salvia miltiorrhiza stem flower |
-
2007
- 2007-07-20 CN CNA2007100183021A patent/CN101348474A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102028743A (en) * | 2009-09-29 | 2011-04-27 | 天津天士力现代中药资源有限公司 | Medicament for treating coronary heart disease and preparation method thereof |
| CN102028746A (en) * | 2009-09-29 | 2011-04-27 | 天津天士力现代中药资源有限公司 | Drug for treating coronary heart disease and extraction method |
| CN102028743B (en) * | 2009-09-29 | 2014-12-24 | 天津天士力现代中药资源有限公司 | Medicament for treating coronary heart disease and preparation method thereof |
| CN102028746B (en) * | 2009-09-29 | 2014-12-24 | 天津天士力现代中药资源有限公司 | Drug for treating coronary heart disease and extraction method |
| CN102690193A (en) * | 2012-03-28 | 2012-09-26 | 西安鸿生生物技术有限公司 | Preparation technology of tanshinol using spray counterflow extraction method |
| CN104611373A (en) * | 2015-02-10 | 2015-05-13 | 南京中医药大学 | Method for efficiently preparing salvianolic acid components from overground stems and leaves of salviae miltiorrhizae employing bioconversion technology |
| CN104761520A (en) * | 2015-04-10 | 2015-07-08 | 大连工业大学 | Method for preparing high-purity salvianolic acid B employing salt precipitation |
| CN106690317A (en) * | 2016-11-11 | 2017-05-24 | 贵州黔贵天赐大健康集团有限公司 | Radix salviae miltiorrhizae composition and preparation method thereof |
| CN106995369A (en) * | 2017-03-31 | 2017-08-01 | 吉林四长制药有限公司 | A kind of preparation method using danshensu as the red sage root extract of object |
| CN106995369B (en) * | 2017-03-31 | 2019-06-14 | 吉林四长制药有限公司 | It is a kind of using danshensu as the preparation method of the red sage root extract of object |
| CN110423230A (en) * | 2019-08-07 | 2019-11-08 | 南阳医学高等专科学校 | A method of tanshin polyphenolic acid B is extracted from Salvia miltiorrhiza stem flower |
| CN110423230B (en) * | 2019-08-07 | 2023-11-14 | 河南度帮中药生物科技股份有限公司 | Method for extracting salvianolic acid B from stems, leaves and flowers of red sage root |
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