CN101157947B - Method for extracting active alkaloid from lycoris herb - Google Patents
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Abstract
The invention discloses a method for extracting active alkaloid from lycoris plants. The method utilizes the combination of an enzymic method and modern mechanical wall-breaking technique to extract lycoris alkaloid. Lycoris alkaloid is extracted efficiently in excellent yields under mild conditions, other impurities dissolution is lowered and the consistency of extract is decreased for continuing treatment of isolation and purification. Segmental extraction technique is adopted according to the alkalinity of lycoris alkaloid to get a plurality of raw products of lycoris alkaloid. Then highly purified monomer of lycoris alkaloids (galanthamin, galanthidine, dihydrogalanthamine, sekisamine) are available after column chromatography and repeated recrystallization. The invention has the advantages of simple line, no pollution, short cycle, high yield of products, high safety coefficient, low cost, diversity of outputs, thus raising the comprehensive utilization of lycoris and reducing the manufacturing cost of deep processing and increasing the feasibility of industrial production.
Description
Technical field
The invention belongs to the natural organic chemistry field, relate to a kind of method of from lycoris plants, extracting active alkaloid.
Background technology
Lycoris (Lycoris Herb.) plant is an important genus in the Amaryllidaceae (Amaryllidaceae), is per nnial herb.According to incompletely statistics, it has kind more than 20 approximately in the whole world, and the warm temperate zone that mainly is distributed in East Asia is to the subtropics.Contain large number of biological alkali in the short-tube lycoris.External scientist goes out large number of biological alkali in 20 beginnings of the century with regard to extraction separation.As Lycorine (narcissine), tazettine (ungernine), homolycorine (narcipoetine), Jia Kela quick (lycoramine), LYCORENINE (lycorenine), Pseudo lycorine (pseudlycorine), Norpluviine (norpluviine), the table Garland adds quick (epigalanthamine), vitatine (vittatine), pluviine (pluviine), hippeastrine alkaloids such as (hippeastrine).
China's science and technology is backward relatively, to just carrying out the research of maryllidaceous alkaloid the 1950's, has also obtained certain achievement.As big vast mountain and sea, Ma Guangen etc. China short-tube lycoris is also carried out the research of vegetable chemistry and pharmacology aspect, and therefrom separated the compound squamigerine (squamigerine) that makes new advances.
Modern pharmacological research and clinical showing, maryllidaceous alkaloid has multiple biological activity and curative effect: lycoremine is the specifics of treatment senile dementia disease, poliomyelitis sequela and myasthenia gravis, and the dysmnesia that dementia patients and brain organic pathology are caused also have the improvement effect; Narcissine have anti-ameba, anticancer, step-down, emetic, eliminate the phlegm, spasmolysis, the analgesic activity stronger 5 times, stronger analgesic activity is also arranged than acetylsalicylic acid than morphine.Its derivative lycobetaine is used for the treatment of digestive tract cancer, liver cancer, ovarian cancer, lung cancer, incidence cancer, malignant lymphoma etc., and is wherein better to cancer of the stomach, ovarian cancer curative effect; Lycoramine is used for the poliomyelitis sequela paralysis, the hemiplegia due to the cerebrovascular accident, sciatic neuritis; Ungernine has the choline-like effect of intending, and the growth of yoshida sarcoma is had fine restraining effect.
At present, be raw material with the short-tube lycoris in the prior art, through loaded down with trivial details extraction separation purification step, only produce a kind of maryllidaceous alkaloid monomer product and the discarded alkaloid that is rich in other valuable activeconstituents, do not make full use of the short-tube lycoris resource, and the high purity requirement that the production cycle is long, the productive rate yield is not high, product is far from reaching pharmaceutical grade.Chinese patent literature " a kind of short-tube lycoris galanthamine hydrobromide sour water lixiviate alkaloid extracting method and technology " (publication number CN1569856, open day be 2005.01.26) in a large amount of use acid extractions, use a large amount of soda acids in the production process, discharge a large amount of spent acid salkali waste, serious environment pollution is unfavorable for industrialization; In a large number with an organic solvent, the production safety coefficient is low in the technology among " method of separating high-purity lycoremine from the short-tube lycoris crude extract " (publication number CN1490319, open day is 2004.04.21), the cost height, and suitability for industrialized production is restricted; Chinese patent literature " method of extraction lycoremine from short-tube lycoris or snowdrop raw material " (publication number CN1696131, be 2005.11.16 in open day) in used instrument cost an arm and a leg, treatment capacity is little, need the advanced techniques personnel to operate, be not suitable for amplifying and produce, industrialization is restricted; And most of technologies are all had to single product, cause the wasting of resources.As " method of separating high-purity lycoremine from the short-tube lycoris crude extract ", " method of separating high-purity lycoremine from the short-tube lycoris crude extract ", " a kind of short-tube lycoris galanthamine hydrobromide resin absorption impurity-removing method and technology " and patent documentations such as " from lycoris plants, extracting the processing method of lycoramine ".
In a word, existing is that the alkaloidal method of raw material production has the following disadvantages with the short-tube lycoris: product is single, step is loaded down with trivial details, the cycle is long, the product recovery rate is not high, safety coefficient is low, cost is high, the short-tube lycoris resource utilization is not high and environmental pollution is serious, and is difficult for industrialization.
Summary of the invention
The object of the present invention is to provide a kind of method of extracting active alkaloid from lycoris plants, this method product recovery rate height can obtain multiple product simultaneously, and environmental pollution is low.
The method of from lycoris plants, extracting active alkaloid provided by the invention, its step comprises:
(1) adding volume in the lycoris plants after chopping is the water of 2~10 times of amounts, add complex cellulase again, the mass percent of complex cellulase and lycoris plants is 0.1~0.5%, regulate pH value to 5~8,20~60 ℃ of following enzymolysis of temperature 2~24 hours, with lycoris plants cytoclasis behind the enzymolysis, filter again, obtain extracting solution;
(2) concentrate said extracted liquid, obtain extract concentrated solution, the proportion of this concentrated solution is 1.05~1.15 when measuring for 20 ℃;
(3) by pH value substep said extracted thing concentrated solution is extracted;
(4) will extract each product of obtaining of step is that 1: 60~1: 5 amount is carried out column chromatography respectively with thick product than filler, carries out wash-out again;
(5) same composition that column chromatography for separation is obtained merges, and recrystallization obtains multiple high-purity monomer repeatedly.
The inventive method has been carried out following optimization to technique scheme,
The component and the mass ratio of complex cellulase are in the step (1): cellulase 40-50%, polygalacturonase 30-40%, hemicellulase 20-30%.
Step (3) extracts by following process:
The first step extraction: the pH of extract concentrated solution is transferred to 5~7, add 0.5~3 times of volume organic solvent and extract 1~4 time, merge organic solvent phase, the reclaim under reduced pressure organic solvent step extraction product of winning;
The extraction of second step: water adjust pH to 7~10 with the first step extraction obtains, add 0.5~3 times of volume organic solvent and extract 1~4 time, merge organic solvent phase, the reclaim under reduced pressure organic solvent gets the second step extraction product;
The extraction of the 3rd step: water adjust pH to 10~11 with the extraction of second step obtains, add 0.5~3 times of volume organic solvent and extract 1~4 time, merge organic solvent phase, the reclaim under reduced pressure organic solvent gets the 3rd step extraction product;
The organic solvent of extraction usefulness is a kind of in chloroform, propyl carbinol, sherwood oil, ethyl acetate, ether and the primary isoamyl alcohol.
In the step (4), the carrier that column chromatography for separation is used is a kind of in macroporous resin, diatomite, carbon 18 fillers, silica gel or the aluminum oxide; The separatory elutriant of chromatography column is one or more mixing in water, methyl alcohol, ethanol, acetone, chloroform, ethyl acetate and the ether.
The solvent that recrystallization is used in the step (5) is one or more mixing in water, methyl alcohol, ethanol, chloroform, ether, n-propyl alcohol and the Virahol.
The inventive method has following technique effect:
(1) extraction yield height, production stage is simple: adopt biological enzymolysis technology that the vegetable cell wall part is decomposed, utilize high speed machine shearing force and whipping force again, destroy plant cell tissue rapidly, the chemical ingredients of histocyte inside is fully contacted with solvent, make the quick solution transfer of effective constituent, reach inside and outside dissolution equilibrium in short period of time at the utmost point, both increased substantially alkaloidal stripping in the plant, impurity stripping when avoiding high temperature extraction again, improve filtyration velocity and purification effect in the production process, simplify the later separation purification step.The present invention and traditional extraction process relatively use the amount of soda acid and organic solvent to significantly reduce, thereby environmentally safe, cost are low.
(2) the stage extraction technology that adopts of the present invention with handicraft product was single different in the past, is divided into 3 sections according to the difference of pH with extract, obtains 3 kinds of main productss at least, and the comprehensive utilization short-tube lycoris has been improved the value of cash crop short-tube lycoris greatly.
(3) product purity height of the present invention: lycoremine purity reaches 99.5%, lycoramine purity reaches more than 99%, and ungernine purity can reach 99%, reaches medicinal requirements, maybe can prepare medicinal its derivative.
Embodiment
Be illustrated for example below, these embodiment are just to the describing in further detail of the inventive method, and do not mean that any limitation of the invention.
Embodiment 1
(1) extracts
Get the 10kg dry lycoris radiata slice, the 30kg aqueous solution in multi-function extractor, transfers pH between 6-7, temperature is a room temperature, add cellulase 13.5g, polygalacturonase 9.6g, hemicellulase 6.9g, enzymolysis 8 hours is after enzymolysis finishes, adopt the Mechanical Crushing technology that plant tissue is smashed to pieces, filter, filtrate is that 0.08-0.09MPa, 70 ℃ concentrate in vacuum tightness, obtain 1.3L proportion and be 1.10 extract concentrated solution of (20 ℃ time).
The Mechanical Crushing technology can be that tissue is smashed homogenate technology, solid sample crushing technology, high pressure cell crushing technology to pieces or dodged the formula extractive technique.
(2) extraction
The first step extraction: transfer the pH to 6.5 of extract concentrated solution, add ether and carry out 2 extractions, consumption is respectively 1.3L, 0.65L, merges ether phase reclaim under reduced pressure ether, the step extraction product of winning;
The second step extraction: the water adjust pH of the first step extraction is to 8.5-9.5, ethyl acetate extraction 5 times, each consumption is 0.5L, combined ethyl acetate phase reclaim under reduced pressure ethyl acetate, the second step extraction product;
The 3rd step extraction: the water adjust pH that the extraction of second step is told is to 10.5-11, extracted with diethyl ether twice, and consumption is respectively 0.6L, 0.4L, merges ether phase reclaim under reduced pressure ether and gets the 3rd step extraction product;
(3) separation and purification
The first step extraction product adds the less water dissolving, sodium bicarbonate alkalizes to pH 8.0, ethyl acetate is inferior in ratio the 3rd step extraction in 1: 1, combined ethyl acetate phase reclaim under reduced pressure ethyl acetate, with product than 1: 20 upper prop of silica gel, sherwood oil: ethyl acetate (10: 1-1: 10) gradient elution, thin layer is followed the tracks of and is detected, merge same composition, methyl alcohol-chloroform recrystallization, dry the 1.8g ungernine.
The second step extraction product adds less water dissolving, is 1: 10 upper prop with product than carbon 18, and respectively with water, 30% methyl alcohol, 60% methyl alcohol, pure methyl alcohol, ethanol elution, thin layer are followed the tracks of and detected, and merge same composition, ethyl alcohol recrystallization, dry the 11.2g lycoremine.
The 3rd step extraction product adds less water dissolving, is 1: 50 upper prop with product than diatomite, and with sherwood oil, ethyl acetate, acetone, methyl alcohol wash-out respectively, thin layer is followed the tracks of and detected, and merges same composition, the n-propyl alcohol recrystallization, dry the 13.7g lycoramine.
Embodiment 2
(1) extracts
Get the 10kg dry lycoris radiata slice, the 40kg aqueous solution, in multi-function extractor, transfer pH between 5-6, temperature is 40 ℃, adds cellulase 8.4g, polygalacturonase 6.6g, hemicellulase 5g, enzymolysis after 2 hours using-system smash the broken sample of homogenate to pieces, filter, filtrate is that 0.08-0.09MPa, 77 ℃ concentrate in vacuum tightness, obtain 1.2L proportion and be 1.07 extract concentrated solution of (20 ℃ time).
(2) extraction
The first step extraction: transfer the pH to 5.0 of extract concentrated solution, add propyl carbinol and carry out 3 extractions, consumption is respectively 0.6L, 0.4L, 0.4L, merges the propyl carbinol phase, reclaim under reduced pressure propyl carbinol, the step extraction product of winning;
The second step extraction: the water layer adjust pH of the first step extraction is to 9.0-9.5, chloroform the 3rd step extraction time, consumption is respectively 0.6L, 0.4L, 0.4L, combined chloroform phase reclaim under reduced pressure chloroform, the second step extraction product;
The extraction of the 3rd step: the second water layer adjust pH that goes on foot extraction is to 10.0-10.5, and primary isoamyl alcohol extracts 6 times, and it all is 0.4L that consumption divides, and merges primary isoamyl alcohol phase reclaim under reduced pressure primary isoamyl alcohol, gets the 3rd step extraction product;
(3) separation and purification
The first step extraction product adds the less water dissolving, sodium hydroxide alkalizes to pH 8.5, ethyl acetate is by step extraction in 1: 1 the 3rd time, combined ethyl acetate phase reclaim under reduced pressure, with product than 1: 60 upper prop of macroporous resin, water, 25%, 50%, 75% ethanol elution, thin layer are followed the tracks of and are detected, and merge same composition, the ether recrystallization, dry the 1.6g ungernine.
The second step extraction product adds less water dissolving, is 1: 10 upper prop with product than silica gel, and respectively with sherwood oil, chloroform, dehydrated alcohol wash-out, thin layer are followed the tracks of and detected, and merge same composition, ethyl alcohol recrystallization, dry the 7.8g lycoremine.
The 3rd step extraction product adds less water dissolving, is 1: 40 upper prop with the product ratio aluminum oxide, and with sherwood oil, acetone, methyl alcohol wash-out respectively, thin layer is followed the tracks of and detected, and merges same composition, the n-propyl alcohol recrystallization, dry the 15.6g lycoramine.
Embodiment 3
(1) extracts
Get 10kg and do the Lycoris aurea sheet, the 100kg aqueous solution, transfer pH between 7-8, temperature is 55 degree, adds cellulase 21.15g, polygalacturonase 13.95g, hemicellulase 9.9g, enzymolysis 24 hours, used the broken sample of high-shear flash extracter 10 minutes, and filtered, filtrate is 0.08-0.09MPa in vacuum tightness, 77 ℃ concentrate, obtain 2.1L proportion and be 1.05 extract concentrated solution of (20 ℃ time).
(2) extraction
The first step extraction: transfer the pH to 6.0 of extract concentrated solution, add ethyl acetate and carry out 4 extractions, each consumption is 0.6L, combined ethyl acetate phase, the reclaim under reduced pressure ethyl acetate step extraction product of winning;
The extraction of second step: the water adjust pH of the first step extraction is to 9.3-9.8, and chloroform extraction secondary, consumption are 0.8L and 0.6L, the combined chloroform phase, and the reclaim under reduced pressure chloroform gets the second step extraction product;
The 3rd step extraction: the water adjust pH of second step extraction is to 10.7-10.9, extracted with diethyl ether three times, consumption is 0.6L, merges the ether phase, the reclaim under reduced pressure ether, the 3rd step extraction product;
(3) separation and purification
The first step extraction product adds the less water dissolving, sodium bicarbonate alkalizes to pH9.0,3 extractions of ethyl acetate, combined ethyl acetate phase reclaim under reduced pressure ethyl acetate, with 1: 45 upper prop of product ratio aluminum oxide, sherwood oil, ethyl acetate, methyl alcohol is wash-out respectively, thin layer is followed the tracks of and is detected, merge same composition, the alcohol-water recrystallization, dry the 4.5g ungernine.
The second step extraction product adds less water dissolving, is 1: 35 upper prop with product than silica gel, and respectively with sherwood oil, chloroform, dehydrated alcohol wash-out, thin layer are followed the tracks of and detected, and merge same composition, ethyl alcohol recrystallization, dry the 13.7g lycoremine.
The 3rd step extraction product adds less water dissolving, is 1: 30 upper prop with the product ratio aluminum oxide, and with sherwood oil, acetone, methyl alcohol wash-out respectively, thin layer is followed the tracks of and detected, and merges same composition, the n-propyl alcohol recrystallization, dry the 11.6g lycoramine.
Claims (2)
1. method of from lycoris plants, extracting active alkaloid, described active alkaloid is ungernine, lycoremine and lycoramine, the step of this method comprises:
(1) adding volume in the lycoris plants after chopping is the water of 2~10 times of amounts, add complex cellulase again, the mass percent of complex cellulase and lycoris plants is 0.1~0.5%, regulate pH value to 5~8,20~60 ℃ of following enzymolysis of temperature 2~24 hours, with lycoris plants cytoclasis behind the enzymolysis, filter again, obtain extracting solution; The component of complex cellulase and mass ratio are: cellulase 40-50%, polygalacturonase 30-40%, hemicellulase 20-30%;
(2) concentrate said extracted liquid, obtain extract concentrated solution, the proportion of this concentrated solution is 1.05~1.15 when measuring for 20 ℃;
(3) by pH value substep said extracted thing concentrated solution is extracted, extraction process is:
The first step extraction: the pH of extract concentrated solution is transferred to 5~7, add 0.5~3 times of volume organic solvent and extract 1~4 time, merge organic solvent phase, the reclaim under reduced pressure organic solvent step extraction product of winning; The organic solvent that the first step extraction is adopted is ether, propyl carbinol or ethyl acetate;
The extraction of second step: water adjust pH to 7~10 with the first step extraction obtains, add 0.5~3 times of volume organic solvent and extract 1~4 time, merge organic solvent phase, the reclaim under reduced pressure organic solvent gets the second step extraction product; The organic solvent that the extraction of second step is adopted is ethyl acetate or chloroform:
The extraction of the 3rd step: water adjust pH to 10~11 with the extraction of second step obtains, add 0.5~3 times of volume organic solvent and extract 1~4 time, merge organic solvent phase, the reclaim under reduced pressure organic solvent gets the 3rd step extraction product; The organic solvent that the extraction of the 3rd step is adopted is ether or primary isoamyl alcohol:
(4)
Ungernine is a kind of separation the among the A1-A3 in the following manner:
(A1) the first step extraction product adds the less water dissolving, sodium bicarbonate alkalizes to pH 8.0, ethyl acetate is in ratio extraction in 1: 13 times, combined ethyl acetate phase reclaim under reduced pressure ethyl acetate, than 1: 20 upper prop of silica gel, sherwood oil: ethyl acetate is by 10: 1-1: 10 gradient elutions with product, thin layer is followed the tracks of and is detected, merge same composition, methyl alcohol-chloroform recrystallization, oven dry obtains ungernine;
(A2) the first step extraction product is dissolved in water, sodium hydroxide alkalizes to pH 8.5, ethyl acetate is by extraction in 1: 13 times, combined ethyl acetate phase reclaim under reduced pressure, with product than 1: 60 upper prop of macroporous resin, water, 25%, 50%, 75% ethanol elution, thin layer is followed the tracks of and is detected, merge same composition, the ether recrystallization, oven dry obtains ungernine;
(A3) the first step extraction product is dissolved in water, sodium bicarbonate alkalizes to pH9.0,3 extractions of ethyl acetate, combined ethyl acetate phase reclaim under reduced pressure ethyl acetate, with 1: 45 upper prop of product ratio aluminum oxide, sherwood oil, ethyl acetate, methyl alcohol is wash-out respectively, thin layer is followed the tracks of and is detected, merge same composition, the alcohol-water recrystallization, oven dry obtains ungernine;
Lycoremine is a kind of separation the among the B1-B3 in the following manner:
(B1) the second step extraction product is dissolved in water, and is 1: 10 upper prop with product than carbon 18, and respectively with water, 30% methyl alcohol, 60% methyl alcohol, pure methyl alcohol, ethanol elution, thin layer is followed the tracks of and detected, and merges same composition, ethyl alcohol recrystallization, and oven dry obtains lycoremine;
(B2) the second step extraction product is dissolved in water, and is 1: 10 upper prop with product than silica gel, and respectively with sherwood oil, chloroform, dehydrated alcohol wash-out, thin layer is followed the tracks of and detected, and merges same composition, ethyl alcohol recrystallization, and oven dry obtains lycoremine;
(B3) the second step extraction product is dissolved in water, and is 1: 35 upper prop with product than silica gel, and respectively with sherwood oil, chloroform, dehydrated alcohol wash-out, thin layer is followed the tracks of and detected, and merges same composition, ethyl alcohol recrystallization, and oven dry obtains lycoremine;
Lycoramine is a kind of separation the among the C1-C3 in the following manner:
(C1) the 3rd step extraction product is dissolved in water, and is 1: 50 upper prop with product than diatomite, and with sherwood oil, ethyl acetate, acetone, methyl alcohol difference wash-out, thin layer is followed the tracks of and detected, and merges same composition, the n-propyl alcohol recrystallization, and oven dry obtains lycoramine;
(C2) the 3rd step extraction product is dissolved in water, and is 1: 40 upper prop with the product ratio aluminum oxide, and with sherwood oil, acetone, methyl alcohol difference wash-out, thin layer is followed the tracks of and detected, and merges same composition, the n-propyl alcohol recrystallization, and oven dry obtains lycoramine;
(C3) the 3rd step extraction product is dissolved in water, and is 1: 30 upper prop with the product ratio aluminum oxide, and with sherwood oil, acetone, methyl alcohol difference wash-out, thin layer is followed the tracks of and detected, and merges same composition, the n-propyl alcohol recrystallization, and oven dry obtains lycoramine;
(5) same composition that column chromatography for separation is obtained merges, and recrystallization obtains multiple high-purity monomer repeatedly.
2. method according to claim 1 is characterized in that: the solvent that recrystallization is used is one or more mixing in water, methyl alcohol, ethanol, chloroform, ether, n-propyl alcohol and the Virahol.
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