CN104817500A - Method for preparing lappaconitine hydrobromate by reduced pressure-ultrasonic coupled extraction - Google Patents
Method for preparing lappaconitine hydrobromate by reduced pressure-ultrasonic coupled extraction Download PDFInfo
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- CN104817500A CN104817500A CN201510265925.3A CN201510265925A CN104817500A CN 104817500 A CN104817500 A CN 104817500A CN 201510265925 A CN201510265925 A CN 201510265925A CN 104817500 A CN104817500 A CN 104817500A
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- lappaconitine
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
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Abstract
The invention discloses a method for preparing lappaconitine hydrobromate by reduced pressure-ultrasonic coupled extraction, belonging to the technical field of natural drug extraction and preparation. The method comprises the following steps: pretreating drugs, carrying out ultrasonic extraction under reduced pressure by using a special extracting solution, carrying out extraction-back extraction, treating with hydrobromic acid, and crystallizing. By utilizing the vacuum generated by pressure reduction and the cavitation effect and stirring action generated by ultrasonic and adding a certain amount of special extracting solution, the lappaconitine in the Aconitum sinomontanum can be synchronously extracted and synthesized, and the preparation of the lappaconitine hydrobromate can be accelerated. The method greatly shortens the production cycle of the product, enhances the yield and purity of the product, has the advantages of simple technique, mild conditions for separation and purification, low toxicity and low production cost, and is suitable for industrial production.
Description
Technical field
The present invention relates to a kind of method preparing Lappaconitine, be specifically related to the coupling of a kind of depressurizing ultrasonic and extract the method preparing Lappaconitine.
Background technology
Lappaconitine (1appaconite hydrobromide, LH), be extract total alkali from cohosh Aconitum sinomontanum Nakai, through the hydrobromate of the two flag class monomer lappaconitines that chemical separation obtains, the non-additive central nervous system anodyne of domestic initiation, its molecular formula C
32h
44o
8n
2h
2o HBr, molecular weight 683.64, CAS registration number 97792-45-5.
Show through pharmacology clinical study, LH has stronger analgesia and detumescence, antipyretic, local anesthetic action, particularly remarkable to the curative effect of malignant, tumor pain and other intractable pains.Its analgesic activity is 7 times of antipyretic and analgesic pyramidon, suitable with Pethidine analgesic effect, holds time longer, is a kind of excellent non-addicted analgesics, without the mutagenesis of teratogenesis tire, also accumulate poisoning can not occurs.Meanwhile, LH has again obvious antiarrhythmic effect.
Research finds, in the rhizome of Chinese monkshood, a lot of alkaloid all has analgesic activities, as N-take off acetyl lappaconitine (DLA), lappaconitine (LA), 3-acetylaconitine, bulleyaconitine are first-class.Wherein to take off the structure of acetyl lappaconitine (DLA) and lappaconitine (LA) closely similar for N-.DLA is adjacent amido phenylformic acid on Aconitine-type structural framework 4, and LA is adjacent acetaminobenzoic acid.Clinically show, after deacetylation, DLA still retains the multiple pharmacologically active of LA, and LA can play analgesic activity by its periphery meta-bolites DLA at maincenter.
N-deacetylation lappaconitine, English name N-deacetyllappaconitine, molecular formula C
30h
42n
2o
7, molecular weight 542.67, CAS accession number 11033-64-0.
A lot of containing in the plant of lappaconitine also contains N-deacetylation lappaconitine, such as Aconitum sinomontanum Nakai, finet monkshood root, Aconitum teucostomum, pale reddish brown Aconitum sinomontanum Nakai etc. simultaneously.When extracting lappaconitine, can N-deacetylation lappaconitine be extracted simultaneously.
Pertinent literature report is had about extracting the research and development preparing Lappaconitine method from Aconitum sinomontanum Nakai, wherein, patent CN 1706831A discloses one " preparation method of Lappaconitine ", described preparation method is, Aconitum sinomontanum Nakai powder, after alcohol immersion diacolation, concentrates, by concentrated solution after acidifying, alkalization, use chloroform extraction, extraction liquid leaves standstill to obtain lappaconitine crystallization through ethanol, prepares Hydrogen bromide Gao Wujia element finally by Hydrogen bromide.The method use the large and organic solvents, chloroform that cost is high of toxicity, the Lappaconitine yield of preparation reaches as high as 0.64%, and its technical process is more complicated, the more and not easily recycling of required medicine, unsuitable suitability for industrialized production.Patent CN103360311 A discloses one " Lappaconitine new preparation process ", described new preparation process is, Aconitum sinomontanum Nakai root powder sodium hydroxide alkalizes, the mixed solvent adding methanol/ethanol carries out thermal backflow dynamic extraction and obtains crude extract, then carries out acidifying, alkalization separations, crystallization, recrystallizing and refining, Hydrogen bromide reaction salify and must finished product to it.Although the product purity that this technique is produced is high, process cycle is short, the yield of its Lappaconitine is general, and easily causes pollution, the increase cost of environment in acidifying alkalization flowchart process, the maximization that cannot generate profit.Patent CN1817865 A discloses one " preparation technology of lappaconitine and hydrobromate thereof ", described preparation technology comprises: Aconitum sinomontanum Nakai block root cuts off or pulverizes, with ethanol reflux extraction or sour water permeating extraction or the extraction of alcohol dipping method, be condensed into rare medicinal extract, obtain Aconitum sinomontanum Nakai crude extract; Again the acid of Aconitum sinomontanum Nakai crude extract is acidified to 1-5, obtained acidizing fluid; And acidizing fluid is crossed Zeo-karb or macroporous adsorbent resin or alumina adsorption, first wash with water, use chloroform again or/and ethanol elution, collect elutriant, be condensed into medicinal extract, again medicinal extract is dissolved in ethanol, placement is spent the night, crystallization, washing with alcohol, obtain lappaconitine alkali, again by itself and Hydrogen bromide reacting by heating, crystallization, is prepared into Lappaconitine.Lappaconitine content prepared by this technique is more than 99%, but the yield of its product is not high, and purification step is more loaded down with trivial details, and the cycle is longer, and have employed the larger chloroform of toxicity to carry out purifying; The wherein application of resin, the cost of the technique of increasing, cannot realize suitability for industrialized production.Patent CN100417646 C discloses one " preparation method of Lappaconitine hydrobromide ", and Aconitum sinomontanum Nakai root is pulverized by described preparation method, extracts with acidic ethanol percolation, sour water percolation.Acidic ethanol percolate is evaporated to fluid extract, cooling, leaves standstill, and filters, adjusts pH9-9.8, with chloroform extraction with basifier; Sour water percolate adds basifier and adjusts pH10-10.9, leaves standstill, and be separated, supernatant liquor discards, throw out chloroform extraction or doubly cross macroporous resin column after the trichloromethane of throw out amount dissolves with 1-2, then uses ethanol-trichloromethane wash-out.Collect extraction liquid or elutriant, adsorbing contaminant, filter, concentrated, containing the solution of crystallization, this solution with ethanol must be diluted, leave standstill, be separated, obtain biology total alkali, biology total alkali ethyl alcohol recrystallization is obtained lappaconitine highly finished product, and these highly finished product and Hydrogen bromide synthesize and obtain Lappaconitine hydrobromide.Lappaconitine hydrobromide purity prepared by this preparation method (high effective liquid chromatography for measuring) more than 98%, but its preparation method repeatedly need adjust pH, and use chloroform extraction, step is more loaded down with trivial details, cost is higher, and toxicity is comparatively large, easily causes the loss of target product, reduce product yield, unsuitable industrialization is produced.
The present invention be directed to the defect of above-mentioned production technique, solve emphatically lappaconitine and the on the low side and problem of easily degraded of hydrobromate yield thereof, again in conjunction with easy and purifying process effectively, rapidly and efficiently prepare the novel process of Lappaconitine, it is with short production cycle, product yield is high, separation purifying technique is easy, can realize green, environmental protection, reduces production cost, improve yield and the quality of product, be easy to industrialization and produce.
Summary of the invention
The present invention proposes first and hyperacoustic cavatition and second-order effect is combined with decompression technology, adopts exclusive extracting solution, by the separation purifying technique of simple and fast, prepares highly purified Lappaconitine.This technology can realize lappaconitine and extract and carry out with preparation simultaneously, while improving the finished product yields, also can improve its purity, have simple to operate, high-efficiency environment friendly, with low cost, be easy to the features such as suitability for industrialized production.
1) raw materials pretreatment
By Aconitum sinomontanum Nakai root after cleaning, drying, pulverize, cross 80 mesh sieves, obtain Aconitum sinomontanum Nakai powder, for subsequent use;
2) depressurizing ultrasonic extracts
Aconitum sinomontanum Nakai powder and exclusive extraction agent are pressed mass volume ratio 1 g:20-30 mL and soak 12-24 hour, at vacuum tightness 0.08-0.1 MPa, power 200-240 W, under the condition of temperature 40-50, depressurizing ultrasonic extracts 30-40 minute, extracts twice; Suction filtration obtains filtrate.
3) extraction and back extraction
By step 2) extracting solution that obtains is evaporated to degree Beaume between 10 and 20, be extracted with ethyl acetate (3-4 time), combining extraction liquid, is evaporated to degree Beaume between 20-30, first with distilled water mixing, stratification, remove water miscible impurity, with aqueous acid, extraction liquid is stripped again, then regulate PH 9-10 with sodium hydroxide or ammoniacal liquor, leave standstill and filter, dry, obtain lappaconitine crude product;
4) crystallization
Lappaconitine crude product dehydrated alcohol thermosol step 3) obtained, leaves standstill, crystallization, filters, and with the absolute ethanol washing crystallization of cooling, obtains lappaconitine.Filtrate is reclaimed, and can be used for next crystallization, guarantees that the loss of lappaconitine drops to minimum.
Particularly, step 2) described in exclusive extraction agent be the mixing solutions of ethanol and glacial acetic acid 20-30:1 by volume.
Particularly, step 2) described in the condition of suction filtration be: vacuum tightness 0.07-0.09 MPa.
Particularly, the condition of concentrating under reduced pressure described in step 3) is: vacuum tightness 0.07-0.09MPa, and temperature is 40-50 DEG C.
Particularly, concentrated solution described in step 3) and the cumulative volume of ethyl acetate are than being 1:15-20.
Particularly, the volume ratio that acetic acid ethyl acetate extract described in step 3) and distilled water mix is 1:1-2, and the stratification time is 1-2 hour.
Particularly, sour water described in step 3) is the aqueous hydrochloric acid of PH between 0.5-1, and the volume ratio of back extraction is ethyl acetate: sour water=1:5-10.
Particularly, leaving standstill filtration time described in step 3) is 0.5-1 hour, and bake out temperature controls at 40-50 DEG C.
Particularly, crude product described in step 4) and hydrobromic mass volume ratio are 1 g:0.5-1 mL.
Particularly, the mass volume ratio of crude product described in step 4) and dehydrated alcohol (thermosol) is 1g:10-13 mL, and its time left standstill is 24-48 hour.
Specific implementation method:
Example 1: get Aconitum sinomontanum Nakai root 1kg, clean, dry, pulverized 80 mesh sieves, adds exclusive extracting solution (95% ethanol and glacial acetic acid 20:1 by volume) 20L, soaks 15h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 200W, under the condition that temperature is 40 DEG C, depressurizing ultrasonic extracts 30 minutes, and extract twice, under vacuum tightness 0.07 MPa, suction filtration merges twice filtrate, at vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 10.The ethyl acetate of getting 6L is divided and is extracted concentrated solutions three times, collects acetic acid ethyl acetate extract, is evaporated to degree Beaume between 20-30, first with the distilled water of 3L and acetic acid ethyl acetate extract mixes, stratification, removes water miscible impurity.Carry out back extraction with 6L aqueous acid again, utilize ammoniacal liquor that the pH of strip liquor is adjusted to 10, filter, collect, dry precipitation.By the precipitation 0.1L dehydrated alcohol thermosol after oven dry, add Hydrogen bromide 0.005L while stirring, suction filtration while hot, wait to leave standstill and separate out precipitation, filtration, obtain refining Lappaconitine, its purity can reach 99.07%, and yield is 0.71%.
Example 2: get Aconitum sinomontanum Nakai root 10kg, clean, dry, pulverized 80 mesh sieves, adds exclusive extracting solution (95% ethanol and glacial acetic acid 20:1 by volume) 250L, soaks 20h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 220W, under the condition that temperature is 45 DEG C, depressurizing ultrasonic extracts 30 minutes, and extract twice, under vacuum tightness 0.07 MPa, suction filtration merges twice filtrate, at vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 10.The ethyl acetate of getting 75L is divided and is extracted concentrated solutions three times, and collect acetic acid ethyl acetate extract, being evaporated to degree Beaume is 30, first with the distilled water of 25L and acetic acid ethyl acetate extract mixes, stratification, removes water miscible impurity.Carry out back extraction with 75L aqueous acid again, utilize ammoniacal liquor that the pH of strip liquor is adjusted to 10, filter, collect, dry precipitation.By the precipitation 1L dehydrated alcohol thermosol after oven dry, add Hydrogen bromide 0.05L while stirring, suction filtration while hot, wait to leave standstill and separate out precipitation, filtration, obtain refining Lappaconitine, its purity can reach 99.18%, and yield is 0.70%.
Example 3: get Aconitum sinomontanum Nakai root 100kg, clean, dry, pulverized 80 mesh sieves, adds exclusive extracting solution (95% ethanol and glacial acetic acid 20:1 by volume) 3000L, soaks 24h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 240W, under the condition that temperature is 50 DEG C, depressurizing ultrasonic extracts 30 minutes, and extract twice, under vacuum tightness 0.07 MPa, suction filtration merges twice filtrate, at vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 10.The ethyl acetate of getting 900L is divided and is extracted concentrated solutions three times, and collect acetic acid ethyl acetate extract, being evaporated to degree Beaume is 30, first with the distilled water of 300L and acetic acid ethyl acetate extract mixes, stratification, removes water miscible impurity.Carry out back extraction with 900L aqueous acid again, utilize ammoniacal liquor that the pH of strip liquor is adjusted to 10, filter, collect, dry precipitation.Precipitation 10L dehydrated alcohol thermosol after drying is added Hydrogen bromide 0.5L, suction filtration while hot while stirring, and wait to leave standstill and separate out precipitation, filter, obtain refining Lappaconitine, its purity can reach 99.36%, and yield is 0.72%.
Example 4: get Aconitum sinomontanum Nakai root 300kg, clean, dry, pulverized 80 mesh sieves, adds exclusive extracting solution (95% ethanol and glacial acetic acid 20:1 by volume) 9000L, soaks 24h.Use depressurizing ultrasonic extraction equipment, at vacuum tightness 0.08MPa, power 240W, under the condition of temperature 50 C, depressurizing ultrasonic extracts 30 minutes, and extract twice, under vacuum tightness 0.07 MPa, suction filtration merges twice filtrate, at vacuum tightness 0.07MPa, temperature is that under the condition of 40 DEG C, concentrating under reduced pressure filtrate to degree Beaume is 10.The ethyl acetate of getting 2700L is divided and is extracted concentrated solutions three times, and collect acetic acid ethyl acetate extract, being evaporated to degree Beaume is 30, first with the distilled water of 900L and acetic acid ethyl acetate extract mixes, stratification, removes water miscible impurity.Carry out back extraction with 2700L aqueous acid again, utilize ammoniacal liquor that the pH of strip liquor is adjusted to 10, filter, collect, dry precipitation.Precipitation 30L dehydrated alcohol thermosol after drying is added Hydrogen bromide 1.5L, suction filtration while hot while stirring, and wait to leave standstill and separate out precipitation, filter, obtain refining Lappaconitine, its purity can reach 99.34%, and yield is 0.73%.
Claims (9)
1. the method preparing Lappaconitine is extracted in depressurizing ultrasonic coupling, it is characterized in that, comprises the steps:
1) medicinal material pre-treatment
Aconitum sinomontanum Nakai root is cleaned, dries, pulverized, crosses 80 mesh sieves, obtain Aconitum sinomontanum Nakai powder, for subsequent use;
2) depressurizing ultrasonic extracts
Aconitum sinomontanum Nakai powder and exclusive extraction agent are pressed mass volume ratio 1g:20-30mL and soaks 12-24 hour, at vacuum tightness 0.08-0.1MPa, under the condition of power 200-240W, temperature 40-50 DEG C, depressurizing ultrasonic extracts 30-40 minute, extracts twice; Suction filtration obtains filtrate.
2.3) extraction and back extraction
By step 2) extracting solution that obtains is evaporated to degree Beaume between 10 and 20, be extracted with ethyl acetate (3-4 time), combining extraction liquid, is evaporated to degree Beaume between 20-30, through distilled water mixing, stratification, remove water miscible impurity, with aqueous acid, extraction liquid is stripped again, regulate PH9-10 through sodium hydroxide or ammoniacal liquor, leave standstill and filter, dry, obtain product crude product;
4) Hydrogen bromide-crystallization
The product crude product dehydrated alcohol thermosol that step 3) is obtained elimination insolubles, and drip a certain amount of Hydrogen bromide while hot, leave standstill, filter after crystallization, with the absolute ethanol washing crystallization of cooling, obtain Lappaconitine sterling.
3. method according to claim 1, is characterized in that, step 2) described in exclusive extraction agent be the mixing solutions of ethanol and glacial acetic acid Hydrogen bromide 20-30:1 by volume, the condition of suction filtration described in it is: vacuum tightness 0.07-0.09MPa.
4. method according to claim 1, is characterized in that, the condition of concentrating under reduced pressure described in step 3) is: vacuum tightness 0.07-0.09MPa, and temperature is 40-50 DEG C.
5. method according to claim 1, is characterized in that, concentrated solution described in step 3) is 1:15-20 with the cumulative volume ratio of ethyl acetate.
6. method according to claim 1, is characterized in that, the volume ratio that acetic acid ethyl acetate extract described in step 3) and distilled water mix is 1:1-2, and the stratification time is 1-2 hour.
7. method according to claim 1, it is characterized in that, sour water described in step 3) is the aqueous hydrochloric acid of PH between 0.5-1, and the volume ratio of back extraction is ethyl acetate: sour water=1:5-10, described standing filtration time is 0.5-1 hour, and bake out temperature controls at 40-50 DEG C.
8. method according to claim 1, is characterized in that, crude product described in step 4) and hydrobromic mass volume ratio are 1g:0.5-1mL.
9. method according to claim 1, is characterized in that, the mass volume ratio of crude product described in step 4) and dehydrated alcohol (thermosol) is 1g:10-13mL, and the time left standstill described in it is 24-48 hour.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1817865A (en) * | 2006-03-03 | 2006-08-16 | 甘肃奇正藏药有限公司 | Preparation of sinomontanine and its hydrobromide |
| CN1951922A (en) * | 2006-10-20 | 2007-04-25 | 佘建文 | Lappaconitine hydrobromide preparation method |
| CN102617468A (en) * | 2012-03-07 | 2012-08-01 | 西北师范大学 | Method for ultrasound-assisted extraction of lappaconitine |
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2015
- 2015-05-24 CN CN201510265925.3A patent/CN104817500A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1817865A (en) * | 2006-03-03 | 2006-08-16 | 甘肃奇正藏药有限公司 | Preparation of sinomontanine and its hydrobromide |
| CN1951922A (en) * | 2006-10-20 | 2007-04-25 | 佘建文 | Lappaconitine hydrobromide preparation method |
| CN102617468A (en) * | 2012-03-07 | 2012-08-01 | 西北师范大学 | Method for ultrasound-assisted extraction of lappaconitine |
Non-Patent Citations (1)
| Title |
|---|
| 高晓燕等: "氢溴酸高乌甲素提取工艺简报", 《中国医药指南》 * |
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Inventor after: Shi Gaofeng Inventor after: Chen Fuwen Inventor after: Wang Guoying Inventor after: Yao Ruixing Inventor before: Chen Fuwen Inventor before: Shi Gaofeng Inventor before: Wang Guoying |
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Effective date of registration: 20170922 Address after: 730050 Qilihe, Gansu Province Lan Ping Ping Road, No. 287, No. Applicant after: Lanzhou University Of Technology Address before: 730900 incubator base of hi tech Industrial Park, Baiyin District, Baiyin, Gansu Applicant before: Chen Fuwen |
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