CN102382119B - 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 extract the method for etrandrine and Demethyl-tetrandrine from Radix Stephaniae Tetrandrae.
Background technology
Etrandrine (Tetrandrine, claim again Tetrandrine, Tetrandrine) and Demethyl-tetrandrine (Demethyl-tetrandrine, claim not only Demethyl-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) root in separate the bisbenzylisoquinoline alkaloid that obtains, structural formula is as follows.
Etrandrine (Tetrandrine) Demethyl-tetrandrine (Demethyl-tetrandrine)
At present more about the pharmaceutical research of etrandrine, existing tablet and injection are applied to clinical, as antirheumatic and anticancer synergia medicine, for illnesss such as rheumatosis, arthrodynia, neurodynias, it is united and applied in lung cancer therapy with low dose of radiation, is also applicable to simple silicon I, II, III phase and each phase anthracosilicosis; Research shows, Demethyl-tetrandrine has analgesia, anti-inflammatory, antianaphylaxis, step-down and certain lax striate effect.
Extract at present the technique of etrandrine and Demethyl-tetrandrine and (see " chemical composition of Chinese materia medica extracts and separates handbook " P130～133 of Yang Yun, Feng Weisheng chief editor; Chinese patent (application number 200710056757.2) adsorption resin method separates the haplont alkali in Radix Stephaniae Tetrandrae total alkaloids) there is following problem: 1. purge process is used benzene to remove Demethyl-tetrandrine as purification solvent, not only make finished product have residual, and production environment and operator are formed to 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 technique to be difficult for amplifying and can not suitability for industrialized production; 3. can not obtain etrandrine and Demethyl-tetrandrine simultaneously.
Summary of the invention
The object of this invention is to provide a kind of method of extracting etrandrine and Demethyl-tetrandrine from Radix Stephaniae Tetrandrae, the 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 murder by poisoning solvent, product noresidue.
The extracting method of etrandrine proposed by the invention and Demethyl-tetrandrine, it is characterized in that, by the Radix Stephaniae Tetrandrae medicinal material of pulverizing 2%～5% admixing calcium lime powder and mix by weight, adopt alcohol extracting method to carry out thermal backflow extraction (volumetric concentration of alcoholic solution can select 70%～85%), obtain the total alkaloids medicinal extract that contains etrandrine and Demethyl-tetrandrine; Regulate behind medicinal extract pH to 2～4 with acidizing reagent, more repeatedly extract with extraction solvent, after leaving standstill, be layered as two layers of organic solvent extraction liquid and acidic aqueous solutions; Will be wherein extraction liquid concentrated with alkalizing agent reduction final vacuum, reclaim extraction solvent, by the extract acetone solution obtaining, after filtration, concentrated rear crystallization, obtain etrandrine crude product, then use ethyl alcohol recrystallization, obtain etrandrine product; Acidic aqueous solution after aforementioned extraction is left standstill is adjusted pH to 9～11, more repeatedly extracts with extraction solvent, reclaims after extraction solvent, by the extract acetone solution obtaining, after filtration, concentrated after crystallization, obtain Demethyl-tetrandrine crude product, use again ethyl alcohol recrystallization, obtain Demethyl-tetrandrine product; Described extraction solvent can be any one or two kinds of combination of ethyl acetate, trichloromethane, methylene dichloride.
Extracting method of the present invention specifically comprises the following steps:
Step 1, extraction medicinal extract: Radix Stephaniae Tetrandrae pulverizing medicinal materials is become to 10～60 object meal, admix calcium lime powder by 2～5% of medicinal material weight, after mixing, insert extractor, the alcoholic solution that is 70～85% by volumetric concentration extracts three times repeatedly, united extraction liquid concentrating under reduced pressure, obtains proportion and is 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, repeatedly extract rear stratification with extraction solvent, separate containing the organic solvent extraction liquid of etrandrine with containing the acidic aqueous solution of Demethyl-tetrandrine; Described acidizing reagent is that mass concentration is 2%～5% sulfuric acid or hydrochloric acid or phosphorus aqueous acid;
In step 3, the organic solvent extraction liquid that obtains in step 2, add alkali lye to carry out reduction reaction, after reclaiming extraction solvent, obtain the extract containing etrandrine, by extract acetone solution, after filtration, concentrated, crystallization, obtain etrandrine crude product after refiltering; By this crude product ethyl alcohol recrystallization, after filtration, be the etrandrine product of purity >=98% after drying;
Step 4, extraction for the second time: the acidic aqueous solution containing Demethyl-tetrandrine that step 2 is obtained, adjust pH to 9.0～11.0, repeatedly extract with extraction solvent again, reclaim after extraction solvent, gained extract acetone solution, after filtration, concentrated, crystallization, obtain Demethyl-tetrandrine crude product after refiltering; This crude product is used to ethyl alcohol recrystallization again, after filtration, be the Demethyl-tetrandrine product of purity >=98% after drying.
Wherein, alkalization reduction and tune pH alkali lye used can be any aqueous solution of sodium hydroxide, potassium hydroxide, ammoniacal liquor or sodium carbonate.
Compared with prior art have the following advantages: the present invention makes full use of the free state of etrandrine and Demethyl-tetrandrine, and the different solubility of the salt generating from different inorganic acid reactions in the aqueous solution and organic solvent, by regulating the pH of material in corresponding steps, make target component after twice liquid-liquid extraction, obtain respectively etrandrine and Demethyl-tetrandrine; Its operation controllability is good, and target component loss is little, and extraction agent used is reusable after reclaiming, and has reduced production cost, is applicable to suitability for industrialized production; The present invention does not use benzene in extraction, has reduced the potential hazard of production process to environment and operator, has effectively avoided the dissolvent residual of benzene; The inventive method can obtain etrandrine and two kinds of products of Demethyl-tetrandrine simultaneously, has effectively improved raw material availability, has reduced production costs.
Embodiment
Below in conjunction with example, technical solution of the present invention is described in further detail.In example, agents useful for same is except TLC detection reagent is analytical pure, and other are technical pure; Radix Stephaniae Tetrandrae medicinal material is bought from medicinal material market, Nanning; TLC detection method is referring to " Chinese Pharmacopoeia " (one of version in 2010, P139) of Chinese Pharmacopoeia Commission's establishment.
Example 1,
Step 1, extract medicinal extract: Radix Stephaniae Tetrandrae pulverizing medicinal materials is become to 20 object meal, get 100kg, after adding the calcium lime powder of 2kg to mix, insert in stainless steel multi-function extractor, adding 400kg volumetric concentration is 70% methanol solution, and heating keeps boiling 2 hours, leaches solution; Extract as stated above twice with 70% methanol solution of 300kg respectively again, merge three times gained extracting solution, concentrating under reduced pressure reclaims methyl alcohol, obtains proportion and be 1.12 total alkaloids medicinal extract;
Step 2, for the first time extraction: by gained medicinal extract with the aqueous hydrochloric acid of 5% concentration 35 DEG C of dissolvings, make it to become pH and be 2 acidic aqueous solution, with the mixed solvent of ethyl acetate and trichloromethane (volume ratio 1: 5) as extraction solvent, etrandrine in extraction acidic aqueous solution, detect by TLC method, until react spot without obvious etrandrine in acidic aqueous solution simultaneously; Leave standstill extraction liquid layering, separate containing the organic solvent extraction liquid of etrandrine with containing the acidic aqueous solution of Demethyl-tetrandrine;
Step 3, the organic solvent extraction liquid of step 2 gained is added to the saturated aqueous sodium carbonate reduction reaction (reaction maintains pH >=8) that alkalizes, after recovery extraction solvent, be extracted thing and use again acetone solution, after filtration, be concentrated into crystallization, leave standstill after crystallization, filter and obtain etrandrine crude product; By this crude product ethyl alcohol recrystallization, obtain white etrandrine crystallization, after filtration, dry to obtain the purity etrandrine product 0.62kg that is 98.5%, yield is 0.62%;
Step 4, reextraction: the acidic aqueous solution containing Demethyl-tetrandrine that step 2 is obtained, with saturated aqueous sodium carbonate tune pH to 9.5, repeatedly extract with above-mentioned extraction solvent again, detect by TLC method simultaneously, until react spot without obvious Demethyl-tetrandrine in the aqueous solution; Reclaim after extraction solvent, the extract acetone solution obtaining, after filtration, concentrate, crystallization, obtain Demethyl-tetrandrine crude product after refiltering; Crude product is used to ethyl alcohol recrystallization twice again, obtain white Demethyl-tetrandrine crystallization, after filtration, to obtain purity after drying be 98.1% Demethyl-tetrandrine product 0.23kg, yield is 0.23%.
Example 2,
Step 1, extraction medicinal extract: Radix Stephaniae Tetrandrae medicinal material 200kg is ground into 40 object meal, after adding the calcium lime powder of 5kg to mix, insert in stainless steel multi-function extractor, adding 800kg volumetric concentration is 80% ethanolic soln, heating keeps boiling 2 hours, leaches solution; Extract as stated above twice with 80% ethanolic soln of 600kg respectively again, merge three times gained extracting solution, concentrating under reduced pressure reclaims ethanol, obtains proportion and be 1.15 total alkaloids medicinal extract;
Step 2, for the first time extraction: by step 1 gained medicinal extract with the aqueous sulfuric acid of 2% concentration 35 DEG C of dissolvings, make it to become pH and be 2.5 acidic aqueous solution, with trichloromethane as extraction solvent, extract the etrandrine in described acidic aqueous solution, detect by TLC method, until react spot without obvious etrandrine in acidic aqueous solution simultaneously; Leave standstill extraction liquid layering, separate containing the organic solvent extraction liquid of etrandrine with containing the acidic aqueous solution of Demethyl-tetrandrine;
Step 3, step 2 gained organic solvent extraction liquid is added to concentration is the reduction (reaction maintains pH >=8.5) of alkalizing of 5% the NaOH aqueous solution, after recovery extraction solvent, be extracted thing and use again acetone solution, after filtration, be concentrated into crystallization, leave standstill after crystallization, filter and obtain etrandrine crude product; By this crude product ethyl alcohol recrystallization, obtain white etrandrine crystallization, after filtration, dry that to obtain purity be 98.8% etrandrine product 1.50kg, yield is 0.75%;
Step 4, reextraction: the acidic aqueous solution containing Demethyl-tetrandrine that step 2 is obtained, with above-mentioned NaOH aqueous solution tune pH to 9.5, repeatedly extract with chloroform extraction solvent again, detect by TLC method simultaneously, until react spot without obvious Demethyl-tetrandrine in the aqueous solution; Reclaim after extraction solvent, the extract acetone solution obtaining, after filtration, concentrate, crystallization, obtain Demethyl-tetrandrine crude product after refiltering; This crude product is used to ethyl alcohol recrystallization twice again, obtain white Demethyl-tetrandrine crystallization, after filtration, to be purity after drying be 98.2% Demethyl-tetrandrine product 0.50kg, yield is 0.25%.
Example 3,
Step 1, extraction medicinal extract: at 50 order Radix Stephaniae Tetrandrae medicinal material coarse powder 500kg, after adding the calcium lime powder of 15kg to mix, insert in stainless steel multi-function extractor, adding 2000kg volumetric concentration is 85% ethanolic soln, heating keeps boiling 2 hours, leaches solution; Extract as stated above twice with 85% ethanolic soln of 1500kg respectively again, merge three times gained extracting solution, concentrating under reduced pressure reclaims ethanol, obtains proportion and be 1.15 total alkaloids medicinal extract;
Step 2, for the first time extraction: by step 1 gained medicinal extract with the phosphate aqueous solution of 2% concentration 60 DEG C of dissolvings, make it to become pH and be 2.5 acidic aqueous solution, with trichloromethane as extraction solvent, etrandrine in extraction acidic aqueous solution, detect by TLC method, until react spot without obvious etrandrine in acidic aqueous solution simultaneously; Leave standstill extraction liquid layering, separate containing the organic solvent extraction liquid of etrandrine with containing the acidic aqueous solution of Demethyl-tetrandrine;
Step 3, by the ammoniacal liquor that concentration is 5% reduction reaction (reaction maintains pH >=8) that alkalizes for step 2 gained organic solvent extraction liquid, reclaim the extract acetone solution that extraction solvent obtains, after filtration, be concentrated into crystallization, leave standstill after crystallization, filter and obtain etrandrine crude product; By this crude product ethyl alcohol recrystallization, obtain white etrandrine crystallization, after filtration, dry be etrandrine product 4.25kg, yield is 0.85%.
Step 4, reextraction: the acidic aqueous solution containing Demethyl-tetrandrine that step 2 is obtained, use NaCO
3the aqueous solution is adjusted pH to 9.0, more repeatedly extracts with chloroform extraction solvent, detects, until react spot without obvious Demethyl-tetrandrine in the aqueous solution by TLC method simultaneously; Reclaim after extraction solvent, the extract acetone solution obtaining, after filtration, concentrate, crystallization, obtain Demethyl-tetrandrine crude product after refiltering; Crude product is used to ethyl alcohol recrystallization twice again, obtain white Demethyl-tetrandrine crystallization, after filtration, to obtain purity after drying be 98.3% Demethyl-tetrandrine product 1.45kg, yield is 0.29%.
Claims (2)
1. the extracting method of an etrandrine and Demethyl-tetrandrine, it is characterized in that, by the Radix Stephaniae Tetrandrae medicinal material of pulverizing 2%～5% admixing calcium lime powder and mix by weight, adopt alcohol extracting method to carry out thermal backflow extraction, obtain the total alkaloids medicinal extract that contains etrandrine and Demethyl-tetrandrine; Regulate behind medicinal extract pH to 2～4 with acidizing reagent, more repeatedly extract with extraction solvent, after leaving standstill, be layered as two layers of organic solvent extraction liquid and acidic aqueous solutions; Will be wherein extraction liquid concentrated with alkalizing agent reduction final vacuum, reclaim extraction solvent, by the extract acetone solution obtaining, after filtration, concentrated rear crystallization, obtain etrandrine crude product, then use ethyl alcohol recrystallization, obtain etrandrine product; Acidic aqueous solution after aforementioned extraction is left standstill is adjusted pH to 9～11, more repeatedly extracts with extraction solvent, reclaims after extraction solvent, by the extract acetone solution obtaining, after filtration, concentrated after crystallization, obtain Demethyl-tetrandrine crude product, use again ethyl alcohol recrystallization, obtain Demethyl-tetrandrine product; Described extraction solvent is any one or two kinds of combination of ethyl acetate, trichloromethane, methylene dichloride.
2. extracting method according to claim 1, is characterized in that, comprises the following steps:
Step 1, extraction medicinal extract: Radix Stephaniae Tetrandrae pulverizing medicinal materials is become to 10～60 object meal, admix calcium lime powder by 2～5% of medicinal material weight, after mixing, insert extractor, the alcoholic solution that is 70～85% by volumetric concentration extracts three times repeatedly, united extraction liquid concentrating under reduced pressure, obtains proportion and is 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, repeatedly extract rear stratification with extraction solvent, separate containing the organic solvent extraction liquid of etrandrine with containing the acidic aqueous solution of Demethyl-tetrandrine; Described acidizing reagent is that mass concentration is 2%～5% sulfuric acid or hydrochloric acid or phosphorus aqueous acid;
In step 3, the organic solvent extraction liquid that obtains in step 2, add alkali lye to carry out reduction reaction, after reclaiming extraction solvent, obtain the extract containing etrandrine, by extract acetone solution, after filtration, concentrated, crystallization, obtain etrandrine crude product after refiltering; By this crude product ethyl alcohol recrystallization, after filtration, be the etrandrine product of purity >=98% after drying;
Step 4, extraction for the second time: the acidic aqueous solution containing Demethyl-tetrandrine that step 2 is obtained, adjust pH to 9.0～11.0, repeatedly extract with extraction solvent again, reclaim after extraction solvent, gained extract acetone solution, after filtration, concentrated, crystallization, obtain Demethyl-tetrandrine crude product after refiltering; By this crude product ethyl alcohol recrystallization, after filtration, be the Demethyl-tetrandrine product of purity >=98% after drying.
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