CN102351929B - Preparation method of high-purity breviscapine active pharmaceutical ingredient - Google Patents
Preparation method of high-purity breviscapine active pharmaceutical ingredient Download PDFInfo
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- CN102351929B CN102351929B CN201110335099.7A CN201110335099A CN102351929B CN 102351929 B CN102351929 B CN 102351929B CN 201110335099 A CN201110335099 A CN 201110335099A CN 102351929 B CN102351929 B CN 102351929B
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- Prior art keywords
- breviscapine
- solution
- breviscarpine
- active pharmaceutical
- pharmaceutical ingredient
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- DJSISFGPUUYILV-UHFFFAOYSA-N UNPD161792 Natural products O1C(C(O)=O)C(O)C(O)C(O)C1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-UHFFFAOYSA-N 0.000 title claims abstract description 24
- DJSISFGPUUYILV-ZFORQUDYSA-N scutellarin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC(O)=CC=1)O2 DJSISFGPUUYILV-ZFORQUDYSA-N 0.000 title claims abstract description 24
- 239000008186 active pharmaceutical agent Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000047 product Substances 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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 6
- NPLTVGMLNDMOQE-UHFFFAOYSA-N carthamidin Natural products C1=CC(O)=CC=C1C1OC2=CC(O)=C(O)C(O)=C2C(=O)C1 NPLTVGMLNDMOQE-UHFFFAOYSA-N 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- 229930190376 scutellarin Natural products 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000011549 crystallization solution Substances 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 229910000474 mercury oxide Inorganic materials 0.000 claims description 3
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010979 pH adjustment Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 abstract description 10
- 230000008025 crystallization Effects 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 9
- 239000013078 crystal Substances 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 2
- 230000007547 defect Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 241001013934 Erigeron breviscapus Species 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a preparation method of a high-purity breviscapine active pharmaceutical ingredient, which comprises the following steps: preparing a crude breviscapine product into a crystalline solution, standing to obtain crystals, dissolving the crystals, precipitating, filtering, dehydrating, and drying to obtain the breviscapine product of which the content is higher than 90%; and carrying out further purification to obtain the breviscapine product of which the content is higher than 98%. The preparation technique is simple, can easily implement industrial production, and solves the problem in refinement of the breviscapine active pharmaceutical ingredient throughout the years. Since the crystallization process enables identical molecules to be arranged orderly, only molecules with identical crystal lattice can crystallize and precipitate, other substances with different crystal lattices are separated from the breviscapine, thereby effectively overcoming the defect of solvent residues and removing other impurities. The prepared breviscapine active pharmaceutical ingredient achieves the standard specification in Chinese Pharmacopoeia 2010 Edition.
Description
Technical field
The invention belongs to plant amedica production technical field, be specifically related to a kind of preparation method of high-purity breviscapine active pharmaceutical ingredient.
background technology
Herba Erigerontis has another name called Herba Erigerontis, belongs to composite family Erigeron breviscapus (Vant.) Hand.-Mazz. platymiscium, and formal name used at school is Erigeron breviscapus (Vant.) Hand.Mazz., is the distinctive wild natural pharmaceutical resources in Yunnan.Herba Erigerontis is planted by domestication, and within 2009, Erigeron breviscapus in Honghe Region is approved for national geography sign protection product.The preparation method of conventional high-content breviscapine active pharmaceutical ingredient need use resin and a large amount of acetone solvents at present, and in product, residuals is difficult to control, and complex process, and production cost is high, and human body and environment are easily polluted.
summary of the invention
The object of the invention is to for the deficiencies in the prior art, a kind of method of preparing high-purity breviscapine active pharmaceutical ingredient is provided, adopt crystallization process to produce, do not use resin and acetone solvent, solve the unmanageable difficult problem of residuals in product.
Object of the present invention is achieved by the following technical programs.
Except as otherwise noted, percentage ratio of the present invention is weight percentage.
A preparation method for breviscapine active pharmaceutical ingredient, comprises the following steps:
1, obtain Breviscarpine crude product with extraction using alcohol Herba Erigerontis raw material;
2, step (1) gained Breviscarpine crude product is mixed with to the solution that concentration is weight percentage 6～10% with the water of 35～90 DEG C, again with lye pH adjustment value to 6.7～7.0, dissolve, add the gac or the talcum powder that account for crude product 0.1～5%, filter and obtain Breviscarpine crystallization solution; Described alkali lye is aqueous sodium hydroxide solution, sodium bicarbonate aqueous solution or potassium hydroxide aqueous solution;
3, the concentration of regulating step (2) gained Breviscarpine crystallization solution is 6～10%, and solution temperature is 50～80 DEG C, and pH value is 6.7～7.0, standing with crystallizer, obtains xln;
4, collect step (3) gained xln, with after 15～30 times of water dissolution, add again equal-volume ethanol, with acid solution adjust pH be 2.0～2.5, separate out yellow mercury oxide, leave standstill more than 8 hours and filter, throw out washes neutrality with water, ethanol dehydration, 80 DEG C of following drying under reduced pressure obtain scutellarin content and are not less than 90% Breviscarpine product; Described acid solution is sulfuric acid, hydrochloric acid, phosphoric acid, acetic acid or careless aqueous acid.
Further by step (4) products obtained therefrom with after 15～30 times of water dissolution, add equal-volume ethanol, with acid solution adjust pH be 2.0～2.5, separate out yellow mercury oxide, leave standstill more than 8 hours and filter, throw out washes neutrality with water, ethanol dehydration, throw out drying under reduced pressure below 80 DEG C is obtained to scutellarin content and be not less than 98% Breviscarpine product, described acid solution is sulfuric acid, hydrochloric acid, phosphoric acid, acetic acid or careless aqueous acid.
Preparation technology of the present invention is simple, be easy to suitability for industrialized production, solve a refining difficult problem for breviscapine active pharmaceutical ingredient for many years, because crystallization process makes same molecular ordered arrangement, only have identical lattice molecule ability crystallization, other materials separate with Breviscarpine because lattice is different, have effectively overcome the problem of dissolvent residual, remove other impurity, the breviscapine active pharmaceutical ingredient of preparing reaches 2010 editions " Chinese Pharmacopoeia " standard regulations simultaneously.
Brief description of the drawings
Fig. 1 is the high-efficient liquid phase chromatogram of Breviscarpine crude product in embodiment 1;
Fig. 2 is the high-efficient liquid phase chromatogram of embodiment 1 gained high-purity breviscapine active pharmaceutical ingredient product;
Fig. 3 is the high-efficient liquid phase chromatogram of embodiment 2 gained high-purity breviscapine active pharmaceutical ingredient products.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in further detail, but drawings and Examples are not limited to the technical solution, and all conversion of doing based on training centre of the present invention, all belong to protection scope of the present invention.
Embodiment 1
Obtain Breviscarpine crude product with extraction using alcohol Herba Erigerontis raw material, its scutellarin content is that 80.8%, Fig. 1 is its high-efficient liquid phase chromatogram after testing, and detection method, chromatographic condition are all undertaken by 2010 editions " Chinese Pharmacopoeia " regulation.Take Breviscarpine crude product 1000g, add 35 DEG C of warm water to be mixed with weight percent concentration 10% feed liquid, use 10%NaHCO
3adjust pH to 6.7-7.0, dissolution filter, filtrate is centrifugal with 16000r/min continuous pipe type whizzer, carry out again essence filter, regulate filter liquor concentration to 10%, Heating temperature to 50 DEG C, adjust pH to 6.7-7.0, pack filtrate into crystallizer and leave standstill, total 60 hours consuming time of natural decrease temperature crystalline, feed temperature is down to 35 DEG C from 50 DEG C and is taken 38 hours, and cooling per hour is not more than 0.39 DEG C, be down to 22 DEG C from 35 DEG C and take 22 hours, cooling per hour is not more than 0.59 DEG C, growing the grain 12 hours, crystallizer interlayer coolant water temperature and the crystallized liquid temperature difference are not more than 15 DEG C, until be down to 22 DEG C, crystallizer rotating speed is 3min/360 °, crystallizer and discharge system equipment are closed unit, kept being barotropic state in container by aseptic compressed air, crystallization yield raw material butt/wet feed butt is 70%, get crystallization and filter to isolate mother liquor, mother liquor is for former process batching, get filter cake and add 5 times of 85-90% washing with alcohol (washing lotion reclaims the batching of ethanol for former process), add doubly 80 DEG C of water dissolution of 15-30, add again equal-volume ethanol, filter, add 10% hydrochloric acid and adjust pH2.0, leave standstill after 8 hours and filter, get filter cake hot wash to neutral, use a small amount of ethanol dehydration, 80 DEG C of following drying under reduced pressure obtain Breviscarpine product.Its scutellarin content is 91.7% after testing.Fig. 2 is its high-efficient liquid phase chromatogram, and detection method, chromatographic condition are all undertaken by 2010 editions " Chinese Pharmacopoeia " regulation.
Embodiment 2
Take embodiment 1 gained Breviscarpine raw produce 1000g, be mixed with weight percent concentration 6%, use 10%NaHCO
3adjust pH7.0, make to dissolve completely, add product weight than 3% needle-use activated carbon, be heated to 60 DEG C and stir filtered while hot half an hour, gained feed liquid is as clear as crystal, getting filtrate adjusting concentration is 6.0%, is heated to 80-82 DEG C, adjusts after pH6.7-7.0, put crystallizer and leave standstill crystallization 60 hours, the 48 hours points of two-stages of crystallisation by cooling carry out, and it is total 28 hours consuming time of one-phase that filtrate temperature drops to 46 DEG C from 60 DEG C, and cooling per hour is not higher than 0.5 DEG C, two-stage be 45 DEG C to 22 DEG C total 20 hours consuming time, cooling per hour is higher than 1.15 DEG C, growing the grain 12 hours, crystallizer interlayer coolant water temperature and the crystallized liquid temperature difference be not higher than 15 DEG C, feed temperature is down to 22 DEG C, in tank, rotating speed is 3min/360 °, crystallizer and discharge system equipment are closed unit, kept being barotropic state in container by aseptic compressed air, crystallization yield, raw material butt/wet feed butt is 83%, get crystallization and filter to isolate mother liquor, mother liquor is for the batching of front operation, get filter cake and add 5 times of 85-90% washing with alcohol, washing lotion reclaims the batching of ethanol for former process, add doubly 80 DEG C of water dissolution of 15-30, add again equal-volume ethanol, filter, add 10% hydrochloric acid and adjust pH2.0, leave standstill be not less than 8 hours after filter, get filter cake hot wash to neutral, with a small amount of 90-95% ethanol dehydration, 80 DEG C of following drying under reduced pressure obtain Breviscarpine product.Its scutellarin content is 99.6% after testing.Fig. 3 is its high-efficient liquid phase chromatogram, and detection method, chromatographic condition are all undertaken by 2010 editions " Chinese Pharmacopoeia " regulation.
Claims (1)
1. a preparation method for breviscapine active pharmaceutical ingredient, comprises the following steps:
(1) obtain Breviscarpine crude product with extraction using alcohol Herba Erigerontis raw material;
(2) step (1) gained Breviscarpine crude product is mixed with to the solution that concentration is weight percentage 6～10% with the water of 35～90 DEG C, again with lye pH adjustment value to 6.7～7.0, dissolve, add the gac or the talcum powder that account for crude product 0.1～5%, filter and obtain Breviscarpine crystallization solution; Described alkali lye is aqueous sodium hydroxide solution, sodium bicarbonate aqueous solution or potassium hydroxide aqueous solution;
(3) concentration of regulating step (2) gained Breviscarpine crystallization solution is 6～10%, and solution temperature is 50～80 DEG C, and pH value is 6.7～7.0, standing with crystallizer, obtains xln;
(4) collect step (3) gained xln, with after 15～30 times of water dissolution, add again equal-volume ethanol, with acid solution adjust pH be 2.0～2.5, separate out yellow mercury oxide, leave standstill more than 8 hours and filter, throw out washes neutrality with water, ethanol dehydration, 80 DEG C of following drying under reduced pressure obtain scutellarin content and are not less than 90% Breviscarpine product; Described acid solution is sulfuric acid, hydrochloric acid, phosphoric acid, acetic acid or careless aqueous acid.
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| CN201110335099.7A CN102351929B (en) | 2011-10-30 | 2011-10-30 | Preparation method of high-purity breviscapine active pharmaceutical ingredient |
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| CN102351929A CN102351929A (en) | 2012-02-15 |
| CN102351929B true CN102351929B (en) | 2014-10-08 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102659875B (en) * | 2012-04-27 | 2014-12-10 | 段志雄 | Extracting method of breviscapine |
| CN105273018B (en) * | 2014-06-17 | 2018-11-27 | 昆药集团股份有限公司 | A kind of lamp-dish flower acetic dihydrate crystallization II and preparation method thereof |
| CN107236009A (en) * | 2017-06-08 | 2017-10-10 | 云南三七科技灯盏花药业有限公司 | The refined preparation method of Breviscapinun Chinese medical extract |
| CN107266510B (en) * | 2017-06-08 | 2020-09-29 | 南涧龙津生物科技有限公司 | Preparation method of breviscapine traditional Chinese medicine extract |
| CN109705179A (en) * | 2019-03-15 | 2019-05-03 | 李小冬 | A method of the extraction purification high-purity scutellarin from radix scutellariae seed shell |
| CN112028953A (en) * | 2020-09-21 | 2020-12-04 | 云南省药物研究所 | Preparation process of high-purity breviscapine raw material medicine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1900102A (en) * | 2006-07-26 | 2007-01-24 | 红河千山生物工程有限公司 | Method for extracting breviscapine from fresh erigeron breviscapus |
| WO2009140887A1 (en) * | 2008-05-22 | 2009-11-26 | 昆明制药集团股份有限公司 | A scutellarin derivative, the preparing process, the pharmaceutical composition and the use thereof |
| CN102048692A (en) * | 2010-12-28 | 2011-05-11 | 湖南恒生制药有限公司 | Aerosol containing Breviscapine and preparation method thereof |
| CN102048691A (en) * | 2010-12-28 | 2011-05-11 | 湖南恒生制药有限公司 | Breviscapin-containing oral cavity spraying agent and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20110006890A (en) * | 2009-07-15 | 2011-01-21 | 주식회사 엘지생활건강 | Composition for promoting the generation of filaggrin |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1900102A (en) * | 2006-07-26 | 2007-01-24 | 红河千山生物工程有限公司 | Method for extracting breviscapine from fresh erigeron breviscapus |
| WO2009140887A1 (en) * | 2008-05-22 | 2009-11-26 | 昆明制药集团股份有限公司 | A scutellarin derivative, the preparing process, the pharmaceutical composition and the use thereof |
| CN102048692A (en) * | 2010-12-28 | 2011-05-11 | 湖南恒生制药有限公司 | Aerosol containing Breviscapine and preparation method thereof |
| CN102048691A (en) * | 2010-12-28 | 2011-05-11 | 湖南恒生制药有限公司 | Breviscapin-containing oral cavity spraying agent and preparation method thereof |
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