CN102382119A - Extraction method of tetrandrine and demethyltetrandrine - Google Patents
Extraction method of tetrandrine and demethyltetrandrine Download PDFInfo
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Abstract
The invention relates to an extraction method of tetrandrine and demethyltetrandrine. The extraction method comprises the steps of: uniformly mixing Stephania tetrandra powder and quick lime powder, carrying out alcohol extraction to obtain total alkaloid extract, adjusting the pH value to 2-4, extracting, and standing for layering; carrying out alkalization and reduction on the extract liquid to obtain extract, dissolving the extract in acetone, filtering, concentrating and crystallizing to obtain tetrandrine crude product, and recrystallizing the tetrandrine crude product to obtain a tetrandrine product; and adjusting pH value of the acidic aqueous solution obtained after standing to 9-11, extracting to obtain extract, dissolving the extract in acetone, filtering, concentrating and crystallizing to obtain demethyltetrandrine crude product, and recrystallizing the demethyltetrandrine crude product to obtain a demethyltetrandrine product. Compared with the prior art, the extraction method has the advantages that: the characteristics of the solubility difference between free tetrandrine and free demethyltetrandrine and demethyltetrandrine salts generated by reaction between acid and each of tetrandrine and demethyltetrandrine is utilized, tetrandrine and demethyltetrandrine can be separately obtained by adjusting the pH value; the operation controllability is good, the component loss is low, the extractant can be reused, benzene is not used in extraction process, and the production cost is low; the extraction method is suitable for industrial production; tetrandrine and demethyltetrandrine products can be simultaneously obtained; and the raw material utilization rate is effectively improved and the production cost is lowered.
Description
Technical field
The invention belongs to effective ingredients in plant separation and extraction technology field, be specifically related to from Radix Stephaniae Tetrandrae, extract retrandrine and the plain method of Radix Stephaniae Tetrandrae second.
Background technology
Retrandrine (Tetrandrine; Claim Radix Stephaniae Tetrandrae alkali, Tetrandrine again) and the plain (Demethyl-tetrandrine of Radix Stephaniae Tetrandrae second; Not only claim to go first Tetrandrine, Fangchinoline) be (but also to claim powder tetrandra root, stone toad, Lignum Aquilariae Resinatum from menispermaceae plant Radix Stephaniae Tetrandrae; Stephania tetrandra S.Moore) separate the bisbenzylisoquinoline alkaloid that obtains in the root, structural formula is following.
Retrandrine (Tetrandrine) Radix Stephaniae Tetrandrae second plain (Demethyl-tetrandrine)
At present more about the pharmaceutical research of retrandrine; Existing tablet and injection are applied to clinical; As antirheumatic and anticancer synergia medicine; Be used for illnesss such as rheumatosis, arthrodynia, neurodynia, it radiates combined utilization in lung cancer therapy with low dose, also is applicable to simple silicon I, II, III phase and each phase anthracosilicosis; Research shows that Radix Stephaniae Tetrandrae second element has analgesia, anti-inflammatory, antianaphylaxis, step-down and certain lax striate effect.
Extract the plain technology of retrandrine and Radix Stephaniae Tetrandrae second at present and (see Yang Yun, Feng Weisheng chief editor's " chemical composition of Chinese materia medica extraction separation handbook P130～133; Chinese patent (application number 200710056757.2) adsorption resin method separates the haplont alkali in the Radix Stephaniae Tetrandrae total alkaloids) there is following problem: 1. purge process uses benzene to remove Radix Stephaniae Tetrandrae second element as purification solvent; It is residual that finished product is had, and production environment and operator are constituted potential hazard; 2. adopting silica gel or resin is main carrier of separating, and the unsuitable recycling of carrier, and complicated operation, production cost are high causes technology to be difficult for amplifying and can not suitability for industrialized production; 3. it is plain to obtain retrandrine and Radix Stephaniae Tetrandrae second simultaneously.
Summary of the invention
The purpose of this invention is to provide a kind of retrandrine and plain method of Radix Stephaniae Tetrandrae second from Radix Stephaniae Tetrandrae, extracted; This method technical process is simple and easy to do, strong operability, production cost are low, be easy to realize suitability for industrialized production; And do not use the murder by poisoning solvent, the product noresidue.
The process for extracting that retrandrine proposed by the invention and Radix Stephaniae Tetrandrae second are plain; It is characterized in that; With the Radix Stephaniae Tetrandrae medicinal material of pulverizing by weight 2%～5% admix the calcium lime powder mixing; Adopt pure extracting method to carry out thermal backflow and extract (volumetric concentration of alcoholic solution can select 70%～85%), obtain containing retrandrine and the plain total alkaloids medicinal extract of Radix Stephaniae Tetrandrae second; Behind acidizing reagent adjusting medicinal extract pH to 2～4, extract repeatedly with extraction solvent again, be layered as two layers of organic solvent extraction liquid and acidic aqueous solutions after leaving standstill; Wherein extraction liquid concentrates with alkalizing agent reduction final vacuum, reclaims extraction solvent, and the extract that obtains is used acetone solution, and crystallization after filtering, concentrating obtains the retrandrine bullion, uses ethyl alcohol recrystallization again, promptly obtains the retrandrine product; Acidic aqueous solution after aforementioned extraction left standstill is transferred pH to 9～11, extracts repeatedly with extraction solvent again, reclaim extraction solvent after; The extract that obtains is used acetone solution, and crystallization after filtering, concentrating obtains the plain bullion of Radix Stephaniae Tetrandrae second; Use ethyl alcohol recrystallization again, promptly obtain the plain product of Radix Stephaniae Tetrandrae second; Described extraction solvent can be the combination of any or two kinds of ETHYLE ACETATE, trichloromethane, methylene dichloride.
Process for extracting of the present invention specifically may further comprise the steps:
Step 1, extraction medicinal extract: the Radix Stephaniae Tetrandrae pulverizing medicinal materials is become 10～60 purpose meal; Admix calcium lime powder by 2～5% of medicinal material weight; Insert extractor behind the mixing; Using volumetric concentration is that 70～85% alcoholic solution extracts three times repeatedly, and united extraction liquid concentrating under reduced pressure obtains proportion and be 1.1～1.2 total alkaloids medicinal extract; Described alcoholic solution is ethanolic soln or methanol solution, and the total consumption of this step alcoholic solution is 10 times of medicinal material weight, and the ratio of three consumptions can be selected 4: 3: 3;
Step 2, extraction for the first time: the medicinal extract that step 1 is obtained is dissolved into the acidic aqueous solution of pH 2～3 with acidizing reagent; Extract the back standing demix repeatedly with extraction solvent, tell the organic solvent extraction liquid acidic aqueous solution plain that contains retrandrine with containing Radix Stephaniae Tetrandrae second; Described acidizing reagent is that mass concentration is 2%～5% the sulfuric acid or the aqueous solution of hydrochloric acid or phosphoric acid;
Step 3, in the resulting organic solvent extraction liquid of step 2, add alkali lye and carry out reduction reaction; Obtain containing the extract of retrandrine behind the recovery extraction solvent; Extract is used acetone solution, through filtering, concentrate, crystallization, obtaining the retrandrine bullion after refiltering; This bullion is used ethyl alcohol recrystallization, after filtering, drying, be the retrandrine product of purity >=98%;
Step 4, extraction for the second time: with the resulting plain acidic aqueous solution of Radix Stephaniae Tetrandrae second that contains of step 2; Transfer pH to 9.0～11.0; Extract repeatedly with extraction solvent again; After reclaiming extraction solvent, the gained extract use acetone solution, through filtering, concentrated, crystallization, obtaining Radix Stephaniae Tetrandrae second element bullion after refiltering; This bullion is used ethyl alcohol recrystallization again, after filtering, drying, be the plain product of Radix Stephaniae Tetrandrae second of purity >=98%.
Wherein, alkalization reduction and the used alkali lye of accent pH can be any aqueous solution of sodium hydroxide, Pottasium Hydroxide, ammoniacal liquor or yellow soda ash.
Compared with prior art have the following advantages: the present invention makes full use of retrandrine and the plain free state of Radix Stephaniae Tetrandrae second; And the different solubility of salt in the aqueous solution and organic solvent that generates with different inorganic acid reactions; Through regulating the pH of material in the corresponding steps; Make target component through behind twice liquid-liquid extraction, it is plain to obtain retrandrine and Radix Stephaniae Tetrandrae second respectively; Its operation controllability is good, and the target component loss is little, and it is reusable that used extraction agent reclaims the back, reduced production cost, is fit to suitability for industrialized production; The present invention does not use benzene in extraction, reduced the potential hazard of production process to environment and operator, has effectively avoided the dissolvent residual of benzene; The inventive method can obtain retrandrine and the plain two kinds of products of Radix Stephaniae Tetrandrae second simultaneously, has improved raw material availability effectively, has reduced production costs.
Embodiment
Below in conjunction with instance technical scheme of the present invention is described in further detail.Agents useful for same is except that the TLC detection reagent is analytical pure in the instance, and other are technical pure; The Radix Stephaniae Tetrandrae medicinal material is bought from the Nanning medicinal material market; The TLC detection method referring to Chinese Pharmacopoeia Commission establishment " (version was one one in 2010, P139) for Chinese pharmacopoeia.
Instance 1,
Step 1, extraction medicinal extract: the Radix Stephaniae Tetrandrae pulverizing medicinal materials is become 20 purpose meal, get 100kg, after the calcium lime powder of adding 2kg mixes; Insert in the stainless steel multi-function extractor; Adding 400kg volumetric concentration is 70% methanol solution, and heating keeps boiling 2 hours, leaches solution; Extract twice as stated above with 70% methanol solution of 300kg respectively again, merge three times the gained extracting solution, concentrating under reduced pressure reclaims methyl alcohol, obtains proportion and be 1.12 total alkaloids medicinal extract;
Step 2, extraction for the first time: with gained medicinal extract with the aqueous hydrochloric acid of 5% concentration 35 ℃ of dissolvings; Make it to become pH and be 2 acidic aqueous solution; With the mixed solvent of ETHYLE ACETATE and trichloromethane (volume ratio 1: 5) as extraction solvent; Retrandrine in the extraction acidic aqueous solution detects with the TLC method simultaneously, and no obvious retrandrine reacts till the spot in acidic aqueous solution; Leave standstill the extraction liquid layering, tell the organic solvent extraction liquid acidic aqueous solution plain that contains retrandrine with containing Radix Stephaniae Tetrandrae second;
Step 3, the organic solvent extraction liquid of step 2 gained is added the saturated aqueous sodium carbonate reduction reaction (pH >=8 are kept in reaction) that alkalizes; Obtain extract behind the recovery extraction solvent and use acetone solution again; Through filtering, being concentrated into crystallization and separating out; After leaving standstill crystallization, filter and obtain the retrandrine bullion; This bullion is used ethyl alcohol recrystallization, obtain white retrandrine crystallization, through filtering, dry to such an extent that purity is 98.5% retrandrine product 0.62kg, yield is 0.62%;
Step 4, reextraction: contain the plain acidic aqueous solution of Radix Stephaniae Tetrandrae second with what step 2 obtained; Transfer pH to 9.5 with saturated aqueous sodium carbonate; Extract repeatedly with above-mentioned extraction solvent, detect with the TLC method simultaneously, no obvious Radix Stephaniae Tetrandrae second is plain in the aqueous solution reacts till the spot; After reclaiming extraction solvent, the extract that obtains use acetone solution, through filtering, concentrated, crystallization, obtaining Radix Stephaniae Tetrandrae second element bullion after refiltering; Bullion being used ethyl alcohol recrystallization twice again, obtain the plain crystallization of white Radix Stephaniae Tetrandrae second, is 98.1% Radix Stephaniae Tetrandrae second element product 0.23kg through filtering, obtain after the oven dry purity, and yield is 0.23%.
Instance 2,
Step 1, extraction medicinal extract: Radix Stephaniae Tetrandrae medicinal material 200kg is ground into 40 purpose meal; After the calcium lime powder of adding 5kg mixes, insert in the stainless steel multi-function extractor, adding 800kg volumetric concentration is 80% ethanolic soln; Heating keeps boiling 2 hours, leaches solution; Extract twice as stated above with 80% ethanolic soln of 600kg respectively again, merge three times the gained extracting solution, concentrating under reduced pressure reclaims ethanol, obtains proportion and be 1.15 total alkaloids medicinal extract;
Step 2, extraction for the first time: with step 1 gained medicinal extract with the aqueous sulfuric acid of 2% concentration 35 ℃ of dissolvings; Make it to become pH and be 2.5 acidic aqueous solution; With trichloromethane as extraction solvent; Extract the retrandrine in the said acidic aqueous solution, detect with the TLC method simultaneously, no obvious retrandrine reacts till the spot in acidic aqueous solution; Leave standstill the extraction liquid layering, tell the organic solvent extraction liquid acidic aqueous solution plain that contains retrandrine with containing Radix Stephaniae Tetrandrae second;
Step 3, step 2 gained organic solvent extraction liquid is added concentration is the reduction (pH >=8.5 are kept in reaction) of alkalizing of 5% the NaOH aqueous solution; Obtain extract behind the recovery extraction solvent and use acetone solution again; Through filtering, being concentrated into crystallization and separating out; After leaving standstill crystallization, filter and obtain the retrandrine bullion; This bullion is used ethyl alcohol recrystallization, obtains white retrandrine crystallization, through filter, to obtain purity be 98.8% retrandrine product 1.50kg in oven dry, yield is 0.75%;
Step 4, reextraction: contain the plain acidic aqueous solution of Radix Stephaniae Tetrandrae second with what step 2 obtained; Transfer pH to 9.5 with the above-mentioned NaOH aqueous solution; Extract repeatedly with the chloroform extraction solvent, detect with the TLC method simultaneously, no obvious Radix Stephaniae Tetrandrae second is plain in the aqueous solution reacts till the spot; After reclaiming extraction solvent, the extract that obtains use acetone solution, through filtering, concentrated, crystallization, obtaining Radix Stephaniae Tetrandrae second element bullion after refiltering; This bullion being used ethyl alcohol recrystallization twice again, obtain the plain crystallization of white Radix Stephaniae Tetrandrae second, is 98.2% Radix Stephaniae Tetrandrae second element product 0.50kg through filtering, be after the oven dry purity, and yield is 0.25%.
Instance 3,
Step 1, extraction medicinal extract: at 50 order Radix Stephaniae Tetrandrae medicinal material coarse powder 500kg; After the calcium lime powder of adding 15kg mixes, insert in the stainless steel multi-function extractor, adding 2000kg volumetric concentration is 85% ethanolic soln; Heating keeps boiling 2 hours, leaches solution; Extract twice as stated above with 85% ethanolic soln of 1500kg respectively again, merge three times the gained extracting solution, concentrating under reduced pressure reclaims ethanol, obtains proportion and be 1.15 total alkaloids medicinal extract;
Step 2, extraction for the first time: with step 1 gained medicinal extract with the phosphate aqueous solution of 2% concentration 60 ℃ of dissolvings; Make it to become pH and be 2.5 acidic aqueous solution; With trichloromethane as extraction solvent; Retrandrine in the extraction acidic aqueous solution detects with the TLC method simultaneously, and no obvious retrandrine reacts till the spot in acidic aqueous solution; Leave standstill the extraction liquid layering, tell the organic solvent extraction liquid acidic aqueous solution plain that contains retrandrine with containing Radix Stephaniae Tetrandrae second;
Step 3, step 2 gained organic solvent extraction liquid is used concentration is 5% the ammoniacal liquor reduction reaction (pH >=8 are kept in reaction) that alkalizes; The extract that the recovery extraction solvent obtains is used acetone solution; After filtering, be concentrated into crystallization and separate out, leaving standstill crystallization, filter and obtain the retrandrine bullion; This bullion is used ethyl alcohol recrystallization, obtain white retrandrine crystallization, be retrandrine product 4.25kg through filtering, drying, yield is 0.85%.
Step 4, reextraction:, use NaCO with the acidic aqueous solution that contains Radix Stephaniae Tetrandrae second element that step 2 obtains
3The aqueous solution is transferred pH to 9.0, extracts repeatedly with the chloroform extraction solvent again, detects with the TLC method simultaneously, and no obvious Radix Stephaniae Tetrandrae second is plain in the aqueous solution reacts till the spot; After reclaiming extraction solvent, the extract that obtains use acetone solution, through filtering, concentrated, crystallization, obtaining Radix Stephaniae Tetrandrae second element bullion after refiltering; Bullion being used ethyl alcohol recrystallization twice again, obtain the plain crystallization of white Radix Stephaniae Tetrandrae second, is 98.3% Radix Stephaniae Tetrandrae second element product 1.45kg through filtering, obtain after the oven dry purity, and yield is 0.29%.
Claims (2)
1. the plain process for extracting of retrandrine and Radix Stephaniae Tetrandrae second; It is characterized in that; With the Radix Stephaniae Tetrandrae medicinal material of pulverizing by weight 2%～5% admix the calcium lime powder mixing, adopt pure extracting method to carry out thermal backflow and extract, obtain containing the total alkaloids medicinal extract of retrandrine and Radix Stephaniae Tetrandrae second element; Behind acidizing reagent adjusting medicinal extract pH to 2～4, extract repeatedly with extraction solvent again, be layered as two layers of organic solvent extraction liquid and acidic aqueous solutions after leaving standstill; Wherein extraction liquid concentrates with alkalizing agent reduction final vacuum, reclaims extraction solvent, and the extract that obtains is used acetone solution, and crystallization after filtering, concentrating obtains the retrandrine bullion, uses ethyl alcohol recrystallization again, promptly obtains the retrandrine product; Acidic aqueous solution after aforementioned extraction left standstill is transferred pH to 9～11, extracts repeatedly with extraction solvent again, reclaim extraction solvent after; The extract that obtains is used acetone solution, and crystallization after filtering, concentrating obtains the plain bullion of Radix Stephaniae Tetrandrae second; Use ethyl alcohol recrystallization again, promptly obtain the plain product of Radix Stephaniae Tetrandrae second; Described extraction solvent is the combination of any or two kinds of ETHYLE ACETATE, trichloromethane, methylene dichloride.
2. process for extracting according to claim 1 is characterized in that, may further comprise the steps:
Step 1, extraction medicinal extract: the Radix Stephaniae Tetrandrae pulverizing medicinal materials is become 10～60 purpose meal; Admix calcium lime powder by 2～5% of medicinal material weight; Insert extractor behind the mixing; Using volumetric concentration is that 70～85% alcoholic solution extracts three times repeatedly, and united extraction liquid concentrating under reduced pressure obtains proportion and be 1.1～1.2 total alkaloids medicinal extract; Described alcoholic solution is ethanolic soln or methanol solution, and the total consumption of this step alcoholic solution is 10 times of medicinal material weight;
Step 2, extraction for the first time: the medicinal extract that step 1 is obtained is dissolved into the acidic aqueous solution of pH 2～3 with acidizing reagent; Extract the back standing demix repeatedly with extraction solvent, tell the organic solvent extraction liquid acidic aqueous solution plain that contains retrandrine with containing Radix Stephaniae Tetrandrae second; Described acidizing reagent is that mass concentration is 2%～5% the sulfuric acid or the aqueous solution of hydrochloric acid or phosphoric acid;
Step 3, in the resulting organic solvent extraction liquid of step 2, add alkali lye and carry out reduction reaction; Obtain containing the extract of retrandrine behind the recovery extraction solvent; Extract is used acetone solution, through filtering, concentrate, crystallization, obtaining the retrandrine bullion after refiltering; This bullion is used ethyl alcohol recrystallization, after filtering, drying, be the retrandrine product of purity >=98%;
Step 4, extraction for the second time: with the resulting plain acidic aqueous solution of Radix Stephaniae Tetrandrae second that contains of step 2; Transfer pH to 9.0～11.0; Extract repeatedly with extraction solvent again; After reclaiming extraction solvent, the gained extract use acetone solution, through filtering, concentrated, crystallization, obtaining Radix Stephaniae Tetrandrae second element bullion after refiltering; This bullion is used ethyl alcohol recrystallization, after filtering, drying, be the plain product of Radix Stephaniae Tetrandrae second of purity >=98%.
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| CN105640831A (en) * | 2016-01-18 | 2016-06-08 | 北京七巧时代科技有限公司 | Multi-effect plant cleanser |
| CN106831804A (en) * | 2017-01-18 | 2017-06-13 | 石药集团江西金芙蓉药业股份有限公司 | The method that ion exchange and silica gel column chromatography separation prepare Stephania tetrandra first, B prime |
| CN109432400A (en) * | 2018-12-27 | 2019-03-08 | 深圳市福美富基因科技有限公司 | A kind of trichogenous composition and its application |
| CN110179799A (en) * | 2019-06-20 | 2019-08-30 | 中国人民解放军军事科学院军事医学研究院 | The application of tetrandrine and the extracting method of tetrandrine |
| CN111153909A (en) * | 2020-01-17 | 2020-05-15 | 石药集团江西金芙蓉药业股份有限公司 | A double-template molecular imprinting purification method for alpha-and beta-carotene in Stephania tetrandra |
| CN112552308A (en) * | 2020-12-28 | 2021-03-26 | 重庆医药高等专科学校 | 5-bromo-bis-demethyltetrandrine ethyl formate crystal form and preparation method thereof |
| CN113185527A (en) * | 2021-05-10 | 2021-07-30 | 浙江耐司康药业有限公司 | Method for separating tetrandrine and tetrandrine |
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| CN104926823A (en) * | 2015-05-28 | 2015-09-23 | 广西大海阳光药业有限公司 | Extraction method for alkaloid in stephania tetrandra |
| CN105541857A (en) * | 2016-01-18 | 2016-05-04 | 北京七巧时代科技有限公司 | Tetrandrine extract as well as preparation method and application thereof |
| CN105640831A (en) * | 2016-01-18 | 2016-06-08 | 北京七巧时代科技有限公司 | Multi-effect plant cleanser |
| CN106831804A (en) * | 2017-01-18 | 2017-06-13 | 石药集团江西金芙蓉药业股份有限公司 | The method that ion exchange and silica gel column chromatography separation prepare Stephania tetrandra first, B prime |
| CN106831804B (en) * | 2017-01-18 | 2018-08-07 | 石药集团江西金芙蓉药业股份有限公司 | The method that ion exchange and silica gel column chromatography separation prepare Stephania tetrandra first, B prime |
| CN109432400A (en) * | 2018-12-27 | 2019-03-08 | 深圳市福美富基因科技有限公司 | A kind of trichogenous composition and its application |
| CN110179799A (en) * | 2019-06-20 | 2019-08-30 | 中国人民解放军军事科学院军事医学研究院 | The application of tetrandrine and the extracting method of tetrandrine |
| CN111153909A (en) * | 2020-01-17 | 2020-05-15 | 石药集团江西金芙蓉药业股份有限公司 | A double-template molecular imprinting purification method for alpha-and beta-carotene in Stephania tetrandra |
| CN111153909B (en) * | 2020-01-17 | 2022-05-17 | 石药集团江西金芙蓉药业股份有限公司 | A double-template molecular imprinting purification method for alpha-and beta-carotene in Stephania tetrandra |
| CN112552308A (en) * | 2020-12-28 | 2021-03-26 | 重庆医药高等专科学校 | 5-bromo-bis-demethyltetrandrine ethyl formate crystal form and preparation method thereof |
| CN113185527A (en) * | 2021-05-10 | 2021-07-30 | 浙江耐司康药业有限公司 | Method for separating tetrandrine and tetrandrine |
| CN113185527B (en) * | 2021-05-10 | 2022-07-29 | 浙江耐司康药业有限公司 | Method for separating tetrandrine and tetrandrine |
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| CN102382119B (en) | 2014-06-25 |
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