CN1448390A - Method of extracting Shishanjianjia from Chinese herbal medicine multi-layer tower - Google Patents
Method of extracting Shishanjianjia from Chinese herbal medicine multi-layer tower Download PDFInfo
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- CN1448390A CN1448390A CN 02115669 CN02115669A CN1448390A CN 1448390 A CN1448390 A CN 1448390A CN 02115669 CN02115669 CN 02115669 CN 02115669 A CN02115669 A CN 02115669A CN 1448390 A CN1448390 A CN 1448390A
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- selagine
- chloroform
- herba lycopodii
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 40
- APLHEOBEIBHCHW-YQEJDHNASA-N Selagine Natural products O=C1NC2=C([C@]3(N)/C(=C/C)/[C@@H](CC(C)=C3)C2)C=C1 APLHEOBEIBHCHW-YQEJDHNASA-N 0.000 claims description 35
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- ZRJBHWIHUMBLCN-YQEJDHNASA-N huperzine A Chemical compound N1C(=O)C=CC2=C1C[C@H]1\C(=C/C)[C@]2(N)CC(C)=C1 ZRJBHWIHUMBLCN-YQEJDHNASA-N 0.000 claims description 35
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- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
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- 150000007524 organic acids Chemical class 0.000 claims description 5
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- SVHVEORJPVYLCT-UHFFFAOYSA-N ethanol;hexane;propan-2-one Chemical compound CCO.CC(C)=O.CCCCCC SVHVEORJPVYLCT-UHFFFAOYSA-N 0.000 claims description 4
- 238000007689 inspection Methods 0.000 claims description 4
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000012267 brine Substances 0.000 claims description 3
- 238000007654 immersion Methods 0.000 claims description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
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- 238000001816 cooling Methods 0.000 claims description 2
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- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical group ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 claims description 2
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- BCZFSDNVXODRAJ-JTTNIQEDSA-N lycopodine Chemical compound C1CCN2CCC[C@@H]3[C@H]4C[C@@H](C)C[C@]32[C@H]1C(=O)C4 BCZFSDNVXODRAJ-JTTNIQEDSA-N 0.000 abstract 1
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- UBAPRWGDQPSCEH-UHFFFAOYSA-N Des-N-methyl-beta-obscurine Natural products N1CCCC2C3CC(C)CC21C(C=CC(=O)N1)=C1C3 UBAPRWGDQPSCEH-UHFFFAOYSA-N 0.000 description 2
- YYWGABLTRMRUIT-XHBSWPGZSA-N Huperzine B Natural products N1CCC[C@@H]2[C@@H]3C=C(C)C[C@]21C(C=CC(=O)N1)=C1C3 YYWGABLTRMRUIT-XHBSWPGZSA-N 0.000 description 2
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The process of extracting lycopodine from Chinese medicine material serrate clubmoss herb includes the following steps: material crushing, soaking, concentration, repeated extraction, column chromatographing, crystallization, efficient liquid phase chromatographic selection, concentration and drying. Owing to the superfine crushing of material and efficient liquid phase chromatographic separation and purification, the present invention has yield of 70-90 ppm and product purity up to 98 % and may be used in industrial production.
Description
(1) technical field
The present invention relates to a kind of traditional Chinese medicine extraction method, relate in particular to a kind of method of from the herbal medicine Herba Lycopodii serrati, extracting selagine.
(2) background technology
The herbal medicine Herba Lycopodii serrati is the herb of pteridophyte Huperziaceae Herba Lycopodii serrati, another name is many because the place of production spreads all over China from reaching the mountain area in north in the south, and the place of production is wide, and another name has feet added to a snake by an ignorant artist grass, Herba pteridis vittatae etc., be perennial herb, be applied to loose stasis of blood blood, swelling and pain relieving, dehumidifying, clearing heat and detoxicating among the people.Its main chemical compositions: selagine, second, the peaceful alkali of Herba Lycopodii serrati, Herba Lycopodii serrati are decided alkaloidss such as alkali, its peaceful alkali of Herba Lycopodii serrati.
Selagine is being used for the treatment of and prevention degenerative brain disorder and the medicine for the treatment of benign memory deficits of China's original creation, is the chemical monomer of extraction separation from the herbal medicine Herba Lycopodii serrati, is a kind of potent reversibility acetylcholinesterase depressant.The man memory function is mainly by the neurotransmitter of a kind of vagusstoff in the brain, can promote maintenance and the consolidation remembered when its increased activity, during minimizing then hypomnesis so that lose.The acetylcholinesterase that exists in human body can decompose vagusstoff, it is reduced in human brain and produces hypomnesis and dementia.Selagine is the inhibitor of acetylcholinesterase, can reduce the Pseudocholinesterase in the brain.
Through clinical verification, after person in middle and old age poor memory person took medicine one month, people's memory of 74-86.6% significantly strengthened, 58-61% slightly to moderate senile dementia patient take medicine one to two month after, not only strengthen memory, improved cognition, and improved the ability of self-cooking life.
Acetylcholinesterase depressant commonly used has his Kelin of selagine sheet that selagine makes and foreign production and sales, and his Kelin is chemosynthesis, and tangible hepatotoxicity is arranged, simultaneously the transformation period of this product short, the clothes after effect time is lacked, and is on the high side.And selagine is to extract from the herbal medicine Herba Lycopodii serrati, easily absorb, and no obvious toxic-side effects, long action time easily sees through hemato encephalic barrier, moderate cost.Since this medicine listing, receive the concern of domestic and international the world of medicine, be incorporated into " world's medicine guide " in the world, had domestic greatly, world market potentiality.
At present, from the herbal medicine Herba Lycopodii serrati, extract selagine, domestic employing laboratory scale is extracted, its main technique step is: raw material is handled (select, pulverize) → dipping (sour water immersion) → concentrated → extraction → column chromatography → refining (employing recrystallization method) etc., yield is low, only reaches 5/100000ths, and purity is below 95%, industrial scale is little, can not meet the need of market.Therefore, the insider seeks new extracting method in research.
(3) summary of the invention
Problems such as purpose of the present invention is low at existing yield in the above-mentioned prior art just, purity is low and a kind of new processing method of from Herba Lycopodii serrati, extracting selagine developed.
The objective of the invention is to realize by following scheme:
Method of the present invention comprises following processing step successively: (1), dipping: the raw material Herba Lycopodii serrati is pulverized the back soaked 38～60 hours tapping 3～6 times with the organic acid dynamic circulation in jar; (2), concentrate: percolate is put into vacuum concentration pot, and 50 ℃～65 ℃ vacuum decompressions are concentrated into 1～10% of original volume; (3), extraction: concentrated solution is transferred pH value to 8～9.5 with sodium hydroxide or potassium hydroxide, chloroform extraction 4～6 times, with the extraction of 0.05～0.2% sodium hydroxide solution, the chloroform solution of obtaining is put into the alkali lye basin again, alkali lye input extraction liquid basin, use chloroform extraction again 2～3 times, the combined chloroform extraction liquid is gone into reclaim under reduced pressure device, concentrating under reduced pressure, vacuum tightness 600～750mmHg, chloroform vapor is recycled to medicinal extract with-0.3～10 ℃ of cool brine coolings with extraction liquid, emits chloroform and goes into basin; (4), column chromatography: will admix silica gel after the medicinal extract oven dry processing, wet method dress post avoids occurring bubble, carries out gradient elution with the chloroform-methanol elutriant of preparing, and with each stream part of thin layer chromatography inspection, collects the high stream part of content; (5), crystallization: high component elutriant is put and is left standstill 10～20 days in the freezer, temperature-0.3～-15 ℃, after precipitation is separated out, the sucking-off supernatant liquor, suction filtration, drying under reduced pressure gets crude product; Wherein: the raw material Herba Lycopodii serrati is the powder through micronizing; The crude product of crystallization gained separates purification (this be the present invention tool characteristics part) with the preparative high performance liquid chromatography instrument, adopts the 150mm silicagel column, use the eluent wash-out, collection selagine section; Selagine liquid is concentrated into 1/2～1/5 of original volume with thinfilm rotary evaporator, concentrated solution is delivered to lyophilize in the vacuum refrigerating machine, get the selagine finished product.
In invention, used eluent can be normal hexane-acetone-ethanol, ratio 1.5～3: 2～4.5: 0.05～0.15; Also be chloroform-methanol, ratio 85～99: 15～1; Eluent also can be methylene dichloride-acetone, ratio 1～5: 1.
The present invention's used organic acid when soaking can be tartrate, also can be oxysuccinic acid.
From extraction process of the present invention and existing extraction process more as can be known, because the pulverizing of existing raw material Herba Lycopodii serrati is to adopt general breaking method, with pulverizing medicinal materials is that meal carries out diacolation, the selagine stripping is incomplete, yield is lower, and the present invention then adopts the super-fine powder crushing technology, can be with the vegetable cell fragmentation, thereby make the selagine stripping more thorough, therefore yield is improved; Moreover, prior art is to adopt recrystallization method to separate, contained another kind of alkaloid---huperzine B is similar to the selagine chemical structure because in the Herba Lycopodii serrati, and the biological activity of huperzine B is very low, adopt the method for recrystallization to be difficult to the two separation, thereby cause yield low, purity is also low, the present invention adopts the high performance liquid chromatography selections to separate, and advantage is by spectral detection, and is different with the retention time of selagine according to stone shirt alkali second, the two can be separated fully, thereby huperzine B is removed, can be made purity reach 98% like this, actual purity can reach more than 99%.
The present invention compared with prior art, its advantage is: can make yield reach 7/100000ths to nine, improve yield 30%, purity also is improved, and produces and can reach industrialized scale, the quality product height, it is strong to enter competitiveness in the international market.
(4) specific embodiments
The present invention is described further below in conjunction with embodiment, but does not limit the present invention.
The technical process that the present invention extracts selagine is: raw material is handled pulverizing → dipping → concentrated → extraction (repeatedly) → column chromatography → crystallization → high performance liquid chromatography selections → concentrate drying → finished product.
Embodiment 1
The method steps of present embodiment extraction selagine is as follows:
(1), get the raw materials ready: raw material is selected, segment, pulverizing, meal, pulverize through super-fine powder again;
(2), dipping: the raw material Herba Lycopodii serrati is pulverized the back in the diacolation jar, soaked 45 hours, every tapping in 10 hours 1 time with the tartrate dynamic circulation;
(3), concentrate: percolate is put into vacuum concentration pot, and 55 ℃ of vacuum decompressions are concentrated into original volume 8%;
(4), extraction: concentrated solution is transferred about pH value to 8.5 with sodium hydroxide, chloroform extraction 4 times, with the extraction of 0.1% sodium hydroxide solution, the chloroform solution of obtaining is put into the alkali lye basin again, alkali lye input extraction liquid basin, use chloroform extraction again 2 times, chloroform extraction liquid is gone into reclaim under reduced pressure device, concentrating under reduced pressure, about vacuum tightness 650mmHg, chloroform vapor cools off with 1 ℃ of cool brine, and extraction liquid is recycled to medicinal extract, emits chloroform and goes into basin;
(5), column chromatography: will medicinal extract admix silica gel after the oven dry, wet method dress post avoids occurring bubble, carries out gradient elution with the chloroform-methanol elutriant of preparation, with each stream of thin layer chromatography inspection part, the high stream part of collection content;
(6), crystallization: high component elutriant is put and is left standstill 12 days in the freezer, temperature-5 ℃, after precipitation is separated out, the sucking-off supernatant liquor, suction filtration, drying under reduced pressure gets crude product;
(7), crude product is separated purification (this be the present invention tool characteristics part) with the preparative high performance liquid chromatography instrument, adopt the 150mm silicagel column, eluent is normal hexane-acetone-ethanol, ratio 1.5-3: 2-4.5: 0.05-0.15, collect the selagine section;
(8), selagine liquid is concentrated into about 1/3 of original volume with thinfilm rotary evaporator, concentrated solution is delivered to lyophilize in the vacuum refrigerating machine, the selagine finished product.
Embodiment 2
The method steps of present embodiment extraction selagine is as follows:
(1), get the raw materials ready: raw material is selected, segment, pulverizing, meal, super-fine powder is pulverized again;
(2), dipping: the raw material Herba Lycopodii serrati is pulverized the back in the diacolation jar, soaked 60 hours, every tapping in 10 hours 1 time with the oxysuccinic acid dynamic circulation;
(3), concentrate: percolate is put into vacuum concentration pot, and 65 ℃ of vacuum decompressions are concentrated into original volume 10%;
(4), extraction: concentrated solution is transferred pH value to 9.5 with sodium hydroxide, chloroform extraction 6 times, with the extraction of 0.2% sodium hydroxide solution, the chloroform solution of obtaining is put into the alkali lye basin again, alkali lye input extraction liquid basin, use chloroform extraction again 3 times, chloroform extraction liquid is gone into reclaim under reduced pressure device, concentrating under reduced pressure, vacuum tightness 750mmHg, chloroform vapor cools off with 5 ℃ of cool brines, and extraction liquid is recycled to medicinal extract, emits chloroform and goes into basin;
(5), column chromatography: will medicinal extract admix silica gel after the oven dry, wet method dress post avoids occurring bubble, carries out gradient elution with the chloroform-methanol elutriant of preparation, with each stream of thin layer chromatography inspection part, the high stream part of collection content;
(6), crystallization: high component elutriant is put and is left standstill 18 days in the freezer, temperature-10 ℃, after precipitation is separated out, the sucking-off supernatant liquor, suction filtration, drying under reduced pressure gets crude product;
(7), crude product is separated purification (this be the present invention tool characteristics part) with the preparative high performance liquid chromatography instrument, adopt the 150mm silicagel column, eluent is normal hexane-acetone-ethanol, ratio 1.5-3: 2-4.5: 0.05-0.15, collect the selagine section;
(8), selagine liquid is concentrated into 1/4 of original volume with thinfilm rotary evaporator, concentrated solution is delivered to lyophilize in the vacuum refrigerating machine, the selagine finished product.
Equipment used in the present invention is the used general-purpose equipment of chemical pharmaceutical industry, as: soak jar, the energy-conservation concentration tank of triple effect, single-action concentration tank, import continuous extraction machine, chromatography column, high-efficient liquid phase color spectrometer, preparative high performance liquid chromatography instrument etc.
Claims (6)
1, a kind of method of from the herbal medicine Herba Lycopodii serrati, extracting selagine, it comprises following processing step successively: (1), dipping: the raw material Herba Lycopodii serrati is pulverized the back soaked 38～60 hours tapping 3～6 times with the organic acid dynamic circulation in jar; (2), concentrate: percolate is put into vacuum concentration pot, and 50 ℃～65 ℃ vacuum decompressions are concentrated into 1～10% of original volume; (3), extraction: concentrated solution is transferred pH value to 8～9.5 with sodium hydroxide or potassium hydroxide, chloroform extraction 4～6 times, with the extraction of 0.05～0.2% sodium hydroxide solution, the chloroform solution of obtaining is put into the alkali lye basin again, alkali lye input extraction liquid basin, use chloroform extraction again 2～3 times, the combined chloroform extraction liquid is gone into reclaim under reduced pressure device, concentrating under reduced pressure, vacuum tightness 600～750mmHg, chloroform vapor is recycled to medicinal extract with-0.3～10 ℃ of cool brine coolings with extraction liquid, emits chloroform and goes into basin; (4), column chromatography: will admix silica gel after the medicinal extract oven dry processing, wet method dress post avoids occurring bubble, carries out gradient elution with the chloroform-methanol elutriant of preparing, and with each stream part of thin layer chromatography inspection, collects the high stream part of content; (5), crystallization: high component elutriant is put and is left standstill 10～20 days in the freezer, temperature-0.3～-15 ℃, after precipitation is separated out, the sucking-off supernatant liquor, suction filtration, drying under reduced pressure gets crude product; It is characterized in that: the raw material Herba Lycopodii serrati is the powder through micronizing; The crude product of crystallization gained separates purification with the preparative high performance liquid chromatography instrument, adopts the 150mm silicagel column, uses the eluent wash-out, collects the selagine section; Selagine liquid is concentrated into 1/2～1/5 of original volume with thinfilm rotary evaporator, concentrated solution is delivered to lyophilize in the vacuum refrigerating machine, get the selagine finished product.
2, the method for extracting selagine from the herbal medicine Herba Lycopodii serrati according to claim 1, it is characterized in that: eluent is normal hexane-acetone-ethanol, ratio 1.5～3: 2～4.5: 0.05～0.15.
3, the method for extracting selagine from the herbal medicine Herba Lycopodii serrati according to claim 1, it is characterized in that: eluent is a chloroform-methanol, ratio 85～99: 15～1.
4, the method for extracting selagine from the herbal medicine Herba Lycopodii serrati according to claim 1, it is characterized in that: eluent is methylene dichloride-acetone, ratio 1～5: 1.
5, the method for extracting selagine from the herbal medicine Herba Lycopodii serrati according to claim 1, it is characterized in that: used organic acid is a tartrate during immersion.
6, the method for extracting selagine from the herbal medicine Herba Lycopodii serrati according to claim 1, it is characterized in that: used organic acid is an oxysuccinic acid during immersion.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02115669 CN1207285C (en) | 2002-03-28 | 2002-03-28 | Method of extracting Shishanjianjia from Chinese herbal medicine multi-layer tower |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 02115669 CN1207285C (en) | 2002-03-28 | 2002-03-28 | Method of extracting Shishanjianjia from Chinese herbal medicine multi-layer tower |
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| CN1448390A true CN1448390A (en) | 2003-10-15 |
| CN1207285C CN1207285C (en) | 2005-06-22 |
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| CN 02115669 Expired - Lifetime CN1207285C (en) | 2002-03-28 | 2002-03-28 | Method of extracting Shishanjianjia from Chinese herbal medicine multi-layer tower |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006056129A1 (en) * | 2004-11-26 | 2006-06-01 | Delong Xie | Compositions of huperzia serrata alkaloids comprising huperzine a and huperzine b and preparation thereof |
| CN100383122C (en) * | 2006-06-15 | 2008-04-23 | 河南太龙药业股份有限公司 | Process of extracting lycopdine A from plant |
| JP2016527219A (en) * | 2013-07-15 | 2016-09-08 | 浙江万邦▲薬業▼股▲ふん▼有限公司Ｚｈｅｊｉａｎｇ Ｗａｎｂａｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｐｌｃ． | Preparation of (-)-Huperzine A |
| CN105949123A (en) * | 2016-06-06 | 2016-09-21 | 江西海富生物工程有限公司 | Huperzine A production method suitable for industrial production |
| CN110078667A (en) * | 2019-04-28 | 2019-08-02 | 云南汉德生物技术有限公司 | A method of extracting huperzine |
-
2002
- 2002-03-28 CN CN 02115669 patent/CN1207285C/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006056129A1 (en) * | 2004-11-26 | 2006-06-01 | Delong Xie | Compositions of huperzia serrata alkaloids comprising huperzine a and huperzine b and preparation thereof |
| US8574633B2 (en) | 2004-11-26 | 2013-11-05 | Delong Xie | Huperzia serrata (Thunb.) Trev. composition comprising compounded Huperzine A and Huperzine B and methods for preparing it |
| CN100383122C (en) * | 2006-06-15 | 2008-04-23 | 河南太龙药业股份有限公司 | Process of extracting lycopdine A from plant |
| JP2016527219A (en) * | 2013-07-15 | 2016-09-08 | 浙江万邦▲薬業▼股▲ふん▼有限公司Ｚｈｅｊｉａｎｇ Ｗａｎｂａｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｐｌｃ． | Preparation of (-)-Huperzine A |
| CN105949123A (en) * | 2016-06-06 | 2016-09-21 | 江西海富生物工程有限公司 | Huperzine A production method suitable for industrial production |
| CN110078667A (en) * | 2019-04-28 | 2019-08-02 | 云南汉德生物技术有限公司 | A method of extracting huperzine |
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| CN1207285C (en) | 2005-06-22 |
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