CN102391266B - Method for extracting and separating pseudolycorine from lycoris plants - Google Patents
Method for extracting and separating pseudolycorine from lycoris plants Download PDFInfo
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- CN102391266B CN102391266B CN 201110443976 CN201110443976A CN102391266B CN 102391266 B CN102391266 B CN 102391266B CN 201110443976 CN201110443976 CN 201110443976 CN 201110443976 A CN201110443976 A CN 201110443976A CN 102391266 B CN102391266 B CN 102391266B
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Abstract
The invention relates to a method for extracting and separating pseudolycorine from lycoris plants, which takes lycoris bulbiferous plant as a raw material. The method for extracting and separating pseudolycorine comprises the following steps: (1) preparing lycoris bulbiferous dry powder; (2) wet mixing a dilute alkali solution; (3)leaching ethyl acetate; (4) distilling and recovering ethyl acetate; (5) acid dissolving; (6) extracting chloroform and removing impurities; (7) regulating pH value; (8) salting out and removing impurities; (9) extracting ethyl acetate; (10) distilling and recovering ethyl acetate; (11) adding water and dissolving; (12) carrying out column chromatography; (13) recrystallizing; (14) vacuum drying. The method for extracting and separating pseudolycorine from lycoris plants reaches the purposes of reasonable operational path, minimum organic solvent amount, high purity of obtained product and stable product quality.
Description
Technical field
The present invention relates to from lycoris plants, extract the method for separating Pseudo lycorine.
Background technology
Amaryllidaceae (Amarylllidaceae) Lycoris is China and some national endemic genuses of East Asia, and its feature is relatively stable, is per nnial herb.Amrallid contains with it multiplely has the alkaloid component of biological activity and pharmacologically active to cause countries in the world pharmaceuticals researcher's concern.Lycoris plants is used as medicinal very early, and according to the Compendium of Material Medica record, lycoris plants has detoxifcation, timid phlegm, diuresis, emetic function.The chemical ingredients of lycoris plants mainly comprises alkaloid and chromocor compound aspect.Alkaloid mainly contains narcissine, Pseudo lycorine, narcipoetine, LYCORENINE, spend more narcissine, lycoremine, make every effort to overcome and draw quick, lycoricidine, hippeastrine etc.
China researches on natural drugs personnel are since research and the drug development of maryllidaceous alkaloid the 1950's, and galanthamine hydrobromide and dihydrogalanthamine (make every effort to overcome draw quick) have been used for clinical; Nineteen eighty-three, the anti-cancer agent oxylycorine passed through clinical identification.Enter 21 century, by new pharmacological screening biological activity, found the more pharmacologically active of maryllidaceous alkaloid.
Pseudo lycorine is the alkaloid that extracts from amrallid narcissus and short-tube lycoris at first, and its free alkali and hydrochloride have obvious restraining effect to the growth of rat W-256 under the animal dosis tolerata.The people such as Furusawa of Hawaii, America university have proved that in the pharmacological research of 1971-1974 Pseudo lycorine can prolong the life-span of the big white mouse of cases with leukemia splenomegaly, suppress reverse transcriptase activity.
Pseudo lycorine (Pseudolycorine) claim again pseudolycorine, white needle-like crystals, 247～248 ℃ of fusing points, its hydrochloride is the white plates crystal, and 288 ℃ of fusing points have antitumor and virus function, it is less that documents and materials record Pseudo lycorine extracts the separation data, the fifth phase in 1978 " herbal medicine communication " (existing name " herbal medicine ") is report to some extent, the present invention be the scientific research personnel of our company through the achievement of the research of long period, fully different from prior art processes and processing condition.
Summary of the invention
Purpose of the present invention is to provide a kind of method of separating Pseudo lycorine from the lycoris plants bulb, and it is reasonable to reach operational path, and consumption of organic solvent is economized most, obtains the product purity height, the requirement of constant product quality.
A kind of method of separating Pseudo lycorine of extracting from lycoris plants of the present invention is characterized in that take the lycoris plants bulb as raw material, extracts with processing condition according to the following steps successively and separates Pseudo lycorine:
(1) short-tube lycoris bulb dry powder is made: with fresh clean short-tube lycoris bulb section, dry, pulverize, get short-tube lycoris bulb dry powder;
(2) diluted alkaline water is mixed wet: add 10 ㎏ 1 by 50 ㎏ short-tube lycoris bulb dry powder: 1(V/V) the ammoniacal liquor mixing is mixed thoroughly, gets weakly alkaline short-tube lycoris bulb powder;
(3) ethyl acetate leaching: the total consumption of ethyl acetate is 10 times of short-tube lycoris bulb dry powder weight, minute three refluxing extraction, and each 1.5h merges three times reflux extracting liquid, gets the ethyl acetate leaching liquid;
(4) Distillation recovery ethyl acetate: the Distillation recovery ethyl acetate gets ethyl acetate extract;
(5) acid is molten: per 1 ㎏ ethyl acetate extract adds the dissolving of 5 ㎏ dilute sulphuric acids, and dilute sulphuric acid concentration 0.5% V/V gets acidic aqueous solution behind the filtering and impurity removing;
(6) chloroform extraction removal of impurities: in above-mentioned acidic aqueous solution volume: the ratio of chloroform volume=1: 1 is with the removal of impurities of chloroform counter-current extraction, gets the acidic aqueous solution after the chloroform removal of impurities, and chloroform is recycled;
(7) transfer pH: regulate acidic aqueous solution after the chloroform removal of impurities with the NaOH solution of 40-50%W/W concentration, make pH=10, get the alkaline aqueous solution after the chloroform removal of impurities;
(8) removal of impurities of saltouing: add sodium-chlor in the alkaline aqueous solution after the chloroform removal of impurities, until solution is saturated, stir, impurity is removed in centrifuging, the liquid of must saltouing;
(9) ethyl acetate extraction: long-pending in the liquid of saltouing: the ratio of ethyl acetate volume=1: 1.5-2, with ethyl acetate the liquid of saltouing is carried out counter-current extraction, get acetic acid ethyl acetate extract;
(10) Distillation recovery ethyl acetate: the distillation acetic acid ethyl acetate extract, reclaim ethyl acetate, get ethyl acetate extraction cream;
(11) be dissolved in water: with dissolved in distilled water ethyl acetate extraction cream, per 1 ㎏ ethyl acetate extraction cream adding distil water, 5 ㎏, fully dissolving, centrifuging keeps clear liquid;
(12) column chromatography: then clear liquid uses first the distilled water wash-out of 2 times of column volumes by the D201 macroporous adsorptive resins, uses the 30%(V/V of 4 times of column volumes again) the methanol aqueous solution wash-out, reclaim elutriant, condensing crystal gets the Pseudo lycorine crude product;
(13) recrystallization: with Pseudo lycorine crude product 50%(V/V) dissolve with ethanol, concentrated recrystallization gets the Pseudo lycorine sterling;
(14) vacuum-drying: recrystallization gained Pseudo lycorine sterling is in 65 ℃ of vacuum-dryings 10 hours, pulverizes to such an extent that purity is 98.4% Pseudo lycorine.
Wherein step (2) diluted alkaline water is mixed wet used sig water and is comprised that also the aqueous solution with sodium bicarbonate or yellow soda ash replaces dilute ammonia solution.
Wherein the used acid of step (5) solution can also be used dilute hydrochloric acid except sulfuric acid.
Wherein step (12) column chromatography elutriant can replace methanol aqueous solution with aqueous ethanolic solution.
The insolubles residue that stays after step (11) is dissolved in water can be used for producing lycoremine and narcissine.
Innovative point of the present invention is: (1) provides a kind of method that fully utilizes the short-tube lycoris resource; (2) provide a kind of method of from the lycoris plants bulb, separating Pseudo lycorine; (3) the present invention in conjunction with counter-current extraction, saltout and the macroporous resin chromatography, processing route is reasonable, obtains the product purity height, steady quality.
The present invention obtains first the higher target extract of content, namely leach the short-tube lycoris bulb and reclaim ethyl acetate with ethyl acetate first and get ethyl acetate extract, Pseudo lycorine in the short-tube lycoris bulb is almost all leached in the ethyl acetate extract, and further separation and purification obtains the very high target product of purity---Pseudo lycorine from medicinal extract again.This is than the method advanced person who usually gets first ethanol extract with ethanol leaching short-tube lycoris bulb and Recycled ethanol, extract impurity is few, purity is high, the counter-current extraction removal of impurities is adopted in chloroform extraction removal of impurities of the present invention, save organic solvent than the direct liquid of common employing-liquid extraction, because impurity is few in the ethyl acetate extract of the present invention, purity is high, therefore in the process of purifies and separates Pseudo lycorine, formality is simple, because the present invention also adopts macroporous resin chromatography and ethyl alcohol recrystallization in rear operation, so product purity of the present invention is high, guarantees product quality.The present invention's extraction all is to adopt counter-current extraction, therefore saves organic solvent.
In a word, a kind of method of from the lycoris plants bulb, separating Pseudo lycorine of the present invention, it is reasonable to reach operational path, and consumption of organic solvent is economized most, obtains the product purity height, the purpose of constant product quality.
Description of drawings
Accompanying drawing 1 is process flow diagram of the present invention, and processing step of the present invention is followed successively by from scheming as can be known: (1) short-tube lycoris bulb dry powder is made;
(2) diluted alkaline water is mixed wet;
(3) ethyl acetate leaching;
(4) Distillation recovery ethyl acetate;
(5) acid is molten;
(6) chloroform extraction removal of impurities;
(7) transfer pH;
(8) removal of impurities of saltouing;
(9) ethyl acetate extraction;
(10) Distillation recovery ethyl acetate;
(11) be dissolved in water;
(12) column chromatography;
(13) recrystallization;
(14) vacuum-drying.
Embodiment
Embodiment 1
Extraction separates Pseudo lycorine with processing condition to click successively step:
(1) short-tube lycoris bulb dry powder is made: with fresh clean short-tube lycoris bulb 200 ㎏ section, dry, pulverize, get short-tube lycoris bulb dry powder 50 ㎏;
(2) diluted alkaline water is mixed wet: add 10 ㎏ 1 in 50 ㎏ short-tube lycoris bulb dry powder: 1(V/V) the ammoniacal liquor mixing is mixed thoroughly, gets weakly alkaline short-tube lycoris bulb powder;
(3) ethyl acetate lixiviate: weakly alkaline short-tube lycoris bulb powder is dropped into extractor, use ethyl acetate 500L, minute three refluxing extraction, each 1.5h merges three times reflux extracting liquid, gets the ethyl acetate leaching liquid;
(4) Distillation recovery ethyl acetate: stay to get ethyl acetate extract 5 ㎏ after the Distillation recovery ethyl acetate;
(5) acid is molten: use concentration 0.5%(V/V) aqueous sulfuric acid 25L stirring and dissolving 5 ㎏ ethyl acetate extracts, then get acidic aqueous solution behind the filtering and impurity removing;
(6) chloroform extraction removal of impurities: get the 25L chloroform and take the counter-current extraction mode, impurity in the above-mentioned acidic aqueous solution is removed in extraction, gets the acidic aqueous solution after the chloroform removal of impurities, and chloroform is recycled;
(7) transfer pH: use 50%(w/w) acidic aqueous solution after the NaOH solution adjusting chloroform removal of impurities of concentration, make pH=10, get the alkaline aqueous solution after the chloroform removal of impurities;
(8) removal of impurities of saltouing: add sodium-chlor in the alkaline aqueous solution after the chloroform removal of impurities, until solution is saturated, stir, impurity is removed in centrifuging, the liquid of must saltouing;
(9) ethyl acetate extraction: get the 40L ethyl acetate liquid of saltouing is carried out counter-current extraction, get acetic acid ethyl acetate extract;
(10) Distillation recovery ethyl acetate: with 40L acetic acid ethyl acetate extract Distillation recovery ethyl acetate, get ethyl acetate extraction cream 2 ㎏;
(11) be dissolved in water: dissolve 2 ㎏ ethyl acetate extraction cream with distilled water 10L, centrifuging keeps clear liquid;
(12) column chromatography: then above-mentioned clear liquid uses first 10L distilled water wash-out by the D201 macroporous adsorptive resins, uses 20L 30%(V/V again) the methanol aqueous solution wash-out, reclaim elutriant, condensing crystal gets the Pseudo lycorine crude product;
(13) recrystallization: with Pseudo lycorine crude product 50%(V/V) dissolve with ethanol, concentrated recrystallization gets the Pseudo lycorine sterling;
(14) vacuum-drying: recrystallization gained Pseudo lycorine sterling is in 65 ℃ of vacuum-dryings 10 hours, pulverizes to such an extent that purity is 98.4% Pseudo lycorine 60g.
Embodiment 2
Extract with processing condition according to the following steps successively and separate Pseudo lycorine:
(1) short-tube lycoris bulb dry powder is made: with fresh clean short-tube lycoris bulb 1000 ㎏ section, dry, pulverize, get short-tube lycoris bulb dry powder 250 ㎏;
(2) diluted alkaline water is mixed wet: adding 50 ㎏ 10%(w/w in 250 ㎏ short-tube lycoris bulb dry powder) the sodium hydrogen carbonate solution mixing is mixed thoroughly, gets weakly alkaline short-tube lycoris bulb powder;
(3) ethyl acetate lixiviate: weakly alkaline short-tube lycoris bulb powder is dropped into extractor, use ethyl acetate 2500L, minute three refluxing extraction, each 1.5h merges three times reflux extracting liquid, gets the ethyl acetate leaching liquid;
(4) Distillation recovery ethyl acetate: stay to get ethyl acetate extract 26 ㎏ after the Distillation recovery ethyl acetate;
(5) acid is molten: use concentration 1%(V/V) aqueous hydrochloric acid 130L stirring and dissolving 26 ㎏ ethyl acetate extracts, then get acidic aqueous solution behind the filtering and impurity removing;
(6) chloroform extraction removal of impurities: get the 130L chloroform and take the counter-current extraction mode, impurity in the above-mentioned acidic aqueous solution is removed in extraction, gets the acidic aqueous solution after the chloroform removal of impurities, and chloroform is recycled;
(7) transfer pH: use 50%(w/w) acidic aqueous solution after the NaOH solution adjusting chloroform removal of impurities of concentration, make pH=10, get the alkaline aqueous solution after the chloroform removal of impurities;
(8) removal of impurities of saltouing: add sodium-chlor in the alkaline aqueous solution after the chloroform removal of impurities, stir until solution is saturated, centrifugally filter out decon, the liquid of must saltouing;
(9) ethyl acetate extraction: get the 250L ethyl acetate liquid of saltouing is carried out counter-current extraction, get acetic acid ethyl acetate extract;
(10) Distillation recovery ethyl acetate: with 250L acetic acid ethyl acetate extract Distillation recovery ethyl acetate, get ethyl acetate extraction cream 10 ㎏;
(11) be dissolved in water: dissolve 10 ㎏ ethyl acetate extraction cream with distilled water 50L, centrifuging keeps clear liquid;
(12) column chromatography: then above-mentioned clear liquid uses first 50L distilled water wash-out by the D201 macroporous adsorptive resins, uses 100L 30%(V/V again) the methanol aqueous solution wash-out, reclaim elutriant, condensing crystal gets the Pseudo lycorine crude product;
(13) recrystallization: with Pseudo lycorine crude product 50%(V/V) dissolve with ethanol, concentrated recrystallization gets the Pseudo lycorine sterling;
(14) vacuum-drying: recrystallization gained Pseudo lycorine sterling is in 65 ℃ of vacuum-dryings 10 hours, pulverizes to such an extent that purity is 98.4% Pseudo lycorine 312g.
Embodiment 3
Extraction separates Pseudo lycorine with processing condition to click successively step:
(1) short-tube lycoris bulb dry powder is made: with fresh clean short-tube lycoris bulb 500 ㎏ section, dry, pulverize, get short-tube lycoris bulb dry powder 130 ㎏;
(2) diluted alkaline water is mixed wet: adding 26 ㎏ 10%(w/w in 130 ㎏ short-tube lycoris bulb dry powder) the sodium hydrogen carbonate solution mixing is mixed thoroughly, gets weakly alkaline short-tube lycoris bulb powder;
(3) ethyl acetate lixiviate: weakly alkaline short-tube lycoris bulb powder is dropped into extractor, use ethyl acetate 260L, minute three refluxing extraction, each 1.5h merges three times reflux extracting liquid, gets the ethyl acetate leaching liquid;
(4) Distillation recovery ethyl acetate: stay to get ethyl acetate extract 13 ㎏ after the Distillation recovery ethyl acetate;
(5) acid is molten: use concentration 0.5%(V/V) aqueous sulfuric acid 65L stirring and dissolving 13 ㎏ ethyl acetate extracts, then get acidic aqueous solution behind the filtering and impurity removing;
(6) chloroform extraction removal of impurities: get the 65L chloroform and take the counter-current extraction mode, impurity in the above-mentioned acidic aqueous solution is removed in extraction, gets the acidic aqueous solution after the chloroform removal of impurities, and chloroform is recycled;
(7) transfer pH: use 50%(w/w) acidic aqueous solution after the NaOH solution adjusting chloroform removal of impurities of concentration, make pH=10, get the alkaline aqueous solution after the chloroform removal of impurities;
(8) removal of impurities of saltouing: add sodium-chlor in the alkaline aqueous solution after the chloroform removal of impurities, until solution stream look and stirring centrifugally filters out decon, the liquid of must saltouing;
(9) ethyl acetate extraction: get the 120L ethyl acetate liquid of saltouing is carried out counter-current extraction, get acetic acid ethyl acetate extract;
(10) Distillation recovery ethyl acetate: with 120L acetic acid ethyl acetate extract Distillation recovery ethyl acetate, get ethyl acetate extraction cream 5 ㎏;
(11) be dissolved in water: dissolve 5 ㎏ ethyl acetate extraction cream with distilled water 25L, centrifuging keeps clear liquid;
(12) column chromatography: then above-mentioned clear liquid uses first 25L distilled water wash-out by the D201 macroporous adsorptive resins, uses 50L 30%(V/V again) the methanol aqueous solution wash-out, reclaim elutriant, condensing crystal gets the Pseudo lycorine crude product;
(13) recrystallization: with Pseudo lycorine crude product 50%(V/V) dissolve with ethanol, concentrated recrystallization gets the Pseudo lycorine sterling;
(14) vacuum-drying: recrystallization gained Pseudo lycorine sterling is in 65 ℃ of vacuum-dryings 10 hours, pulverizes to such an extent that purity is 98.5% Pseudo lycorine 146g.
Claims (4)
1. one kind is extracted the method for separating Pseudo lycorine from lycoris plants, it is characterized in that take the lycoris plants bulb as raw material, extracts with processing condition according to the following steps successively and separates Pseudo lycorine:
(1) short-tube lycoris bulb dry powder is made: with fresh clean short-tube lycoris bulb section, dry, pulverize, get short-tube lycoris bulb dry powder;
(2) diluted alkaline water is mixed wet: add 10 ㎏ 1 by 50 ㎏ short-tube lycoris bulb dry powder: 1V/V ammoniacal liquor mixes to be mixed thoroughly, gets weakly alkaline short-tube lycoris bulb powder;
(3) ethyl acetate leaching: the total consumption of ethyl acetate is 10 times of short-tube lycoris bulb dry powder weight, minute three refluxing extraction, and each 1.5h merges three times reflux extracting liquid, gets the ethyl acetate leaching liquid;
(4) Distillation recovery ethyl acetate: the Distillation recovery ethyl acetate gets ethyl acetate extract;
(5) acid is molten: per 1 ㎏ ethyl acetate extract adds the dissolving of 5 ㎏ dilute sulphuric acids, and dilute sulphuric acid concentration 0.5% V/V gets acidic aqueous solution behind the filtering and impurity removing;
(6) chloroform extraction removal of impurities: in above-mentioned acidic aqueous solution volume: the ratio of chloroform volume=1: 1 is with the removal of impurities of chloroform counter-current extraction, gets the acidic aqueous solution after the chloroform removal of impurities, and chloroform is recycled;
(7) transfer pH: regulate acidic aqueous solution after the chloroform removal of impurities with the NaOH solution of 40-50%W/W concentration, make pH=10, get the alkaline aqueous solution after the chloroform removal of impurities;
(8) removal of impurities of saltouing: add sodium-chlor in the alkaline aqueous solution after the chloroform removal of impurities, until solution is saturated, stir, impurity is removed in centrifuging, the liquid of must saltouing;
(9) ethyl acetate extraction: long-pending in the liquid of saltouing: the ratio of ethyl acetate volume=1: 1.5-2, with ethyl acetate the liquid of saltouing is carried out counter-current extraction, get acetic acid ethyl acetate extract;
(10) Distillation recovery ethyl acetate: the distillation acetic acid ethyl acetate extract, reclaim ethyl acetate, get ethyl acetate extraction cream;
(11) be dissolved in water: with dissolved in distilled water ethyl acetate extraction cream, per 1 ㎏ ethyl acetate extraction cream adding distil water, 5 ㎏, fully dissolving, centrifuging keeps clear liquid;
(12) column chromatography: then clear liquid uses first the distilled water wash-out of 2 times of column volumes by the D201 macroporous adsorptive resins, uses the 30%V/V methanol aqueous solution wash-out of 4 times of column volumes again, reclaims elutriant, and condensing crystal gets the Pseudo lycorine crude product;
(13) recrystallization: with Pseudo lycorine crude product 50%V/V dissolve with ethanol, concentrated recrystallization gets the Pseudo lycorine sterling;
(14) vacuum-drying: recrystallization gained Pseudo lycorine sterling is in 65 ℃ of vacuum-dryings 10 hours, pulverizes to such an extent that purity is 98.4% Pseudo lycorine.
2. a kind of method of extract separating Pseudo lycorine from lycoris plants according to claim 1 is characterized in that step (2) diluted alkaline water mixes wet used sig water and comprise that also the aqueous solution with sodium bicarbonate or yellow soda ash replaces dilute ammonia solution.
3. a kind of method of separating Pseudo lycorine of extracting from lycoris plants according to claim 1 is characterized in that the molten used dilute sulphuric acid of step (5) acid replaces with dilute hydrochloric acid.
4. a kind of method of separating Pseudo lycorine of extracting from lycoris plants according to claim 1 is characterized in that step (12) column chromatography elutriant replaces methanol aqueous solution with aqueous ethanolic solution.
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| CN1936013A (en) * | 2006-09-12 | 2007-03-28 | 贵州芊芊园艺新技术发展公司 | Technological method for extracting lycorine from lycoris plants |
| CN101008023A (en) * | 2006-12-20 | 2007-08-01 | 贵州芊芊园艺新技术发展公司 | Technology for extracting dihydrogalanthamine from lycoris radiata genus plant |
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| CN1936013A (en) * | 2006-09-12 | 2007-03-28 | 贵州芊芊园艺新技术发展公司 | Technological method for extracting lycorine from lycoris plants |
| CN101008023A (en) * | 2006-12-20 | 2007-08-01 | 贵州芊芊园艺新技术发展公司 | Technology for extracting dihydrogalanthamine from lycoris radiata genus plant |
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