CN112110826B - Method for extracting levodopa from cat beans - Google Patents

Method for extracting levodopa from cat beans Download PDF

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CN112110826B
CN112110826B CN201910539636.6A CN201910539636A CN112110826B CN 112110826 B CN112110826 B CN 112110826B CN 201910539636 A CN201910539636 A CN 201910539636A CN 112110826 B CN112110826 B CN 112110826B
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levodopa
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cat
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extracting
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蒙汉富
李伟
黄华凤
覃香泉
黄振华
戴丽琼
莫川献
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Wu Ji
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/38—Separation; Purification; Stabilisation; Use of additives
    • C07C227/40—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C12P7/06—Ethanol, i.e. non-beverage
    • C12P7/065—Ethanol, i.e. non-beverage with microorganisms other than yeasts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

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  • Coloring Foods And Improving Nutritive Qualities (AREA)
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Abstract

The invention relates to a method for extracting levodopa from cat beans, and belongs to the technical field of extraction. The method for extracting the levodopa from the cat beans comprises the following steps: 1) Crushing: pulverizing semen Canavaliae into 14-300 mesh; 2) Extracting: adding an acidic aqueous solution with the weight which is 3-30 times of the total weight of the crushed cat bean raw material, heating to gelatinize, cooling, adding sweet wine yeast and complex enzyme, and fermenting to obtain a fermentation liquor; 3) And (3) crystallization: adding acid into the fermentation liquid to adjust the pH value to 2, filtering, adding 1-3 times of water into filter residues, adjusting the pH value to 2, filtering, combining filtrate, concentrating, and recovering to obtain ethanol; standing the concentrated solution for crystallization to obtain a crude levodopa product; 4) Recrystallizing to obtain the L-dopa with the purity of more than 99.2 percent. The method disclosed by the invention has the advantages of simple process, good product quality, convenience in operation, high economic benefit, low cost and suitability for industrial production, and the bean dregs can be used for feed without waste water, waste gas and waste products.

Description

Method for extracting levodopa from cat beans
[ field of technology ]
The invention relates to the technical field of extraction, in particular to a method for extracting levodopa from cat beans.
[ background Art ]
Cat beans, latin's name Mucuna cochinchine-sis (Lour) Tang et Wang, respectively called Lipuidambaris, oriental Italian Mucuna, tiger bean, cande labra bean, cat bean, leguminosae, annual grass vine plants of the genus Lipuidambaris. The stem is cylindrical, the tendril is 2-10 m long, the branches are multiple, three leaves are covered, the small She Ju round oval, the overall inflorescence, the butterfly corolla are nearly white or purple, the plant is drought-resistant and highly adaptive, the root of the plant is provided with a plurality of rhizobia, the soil fertility can be improved, the root system is developed, the tendril is high, the coverage area is wide, and the plant is favorable for retaining water and soil. The original asia is mainly distributed in south and east areas of south China, southwest and Jiangxi, hunan and Guangxi provinces. The whole body of the cat bean is Bao, and the bean shells, the bean leaves and the bean seeds are rich in crude fat and crude protein, so that the cat bean is a feed for the upper pigs.
Studies have shown that the cat beans mainly contain non-protein amino acids such as levodopa and chenopodium album, indoles such as beta-carboline and quinoline alkaloids, and fatty acid compounds such as oleic acid, linoleic acid, linolenic acid and palmitic acid.
Levodopa (3, 4-Dihydrox ylphenylalanine, L-Dopa) belongs to phenylalanine compounds, is the most commonly used and effective medicament for treating primary paralysis agitans and non-drug-induced paralysis agitans syndrome (Parkinson's disease) at present, and is one of main effective active ingredients of cat beans and velvet beans. English name: levodopa, chinese synonym: 3-hydroxy-L-tyrosine; l-dopa, L-3- (3, 4-dihydroxyphenyl) alanine, L-B- (3, 4-dihydroxyphenyl) alanine, L-beta- (3, 4-dihydroxyphenyl) alanine, L-dopa; 3- (3, 4-dihydroxybenzene) -L-alanine, L-3- (3, 4-dihydroxyphenyl) alanine. The molecular formula: C9H11N04, molecular weight 197.19, cas no: 59-92-7, EINECS number: 200-445-2. A colored or white-like crystalline powder. Melting point 285.5 ℃ (decomposition). Is easily soluble in dilute acid, slightly soluble in water, insoluble in ethanol, diethyl ether and chloroform. No odor, no smell, and blackening in air. Levodopa is one of the effective drugs for treating paralysis agitans at present, is one of precursors for synthesizing norepinephrine, dopamine and the like in vivo, and belongs to catecholamine. Levodopa can enter the brain through the blood brain barrier and act by decarboxylation by polymaleic enzyme to dopamine.
At present, a large amount of organic solvents are used in the process of extracting the levodopa from the cat beans, or macroporous ion adsorption resin is used, so that the cost is high, the operation is inconvenient, the amount of generated wastewater is large, the environmental pollution is serious, the purity of the extracted levodopa is not high, and alcohol is not obtained by comprehensive utilization.
[ invention ]
The invention aims at: aiming at the problems, the method for extracting the levodopa from the cat beans is simple in process, good in product quality, convenient to operate, low in cost and suitable for industrial production.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
a method for extracting levodopa from cat beans, comprising the steps of:
1) Crushing: pulverizing semen Canavaliae into 14-300 mesh;
2) Extracting: adding an acidic aqueous solution with the weight which is 3-30 times of the total weight of the crushed cat bean raw material, heating to gelatinize, cooling, adding sweet wine yeast and complex enzyme, and fermenting to obtain a fermentation liquor;
3) And (3) crystallization: adding acid into the fermentation liquid to adjust the pH value to 2, filtering, adding 1-3 times of water into filter residues, adjusting the pH value to 2, filtering, combining filtrate, concentrating, and recovering to obtain ethanol; standing the concentrated solution for crystallization to obtain a crude levodopa product;
4) And (5) recrystallizing: filtering the crude product, adding ion water to dissolve completely, adjusting pH to 3.5, adding 0.1-20% active carbon for decolorizing, filtering, concentrating to 1/2 of the original volume, and crystallizing to obtain L-dopa with purity of more than 99.2%.
Further, in step 2), the pH of the acidic aqueous solution is 1 to 4.
Further, in the step 2), the temperature of the heating gelatinization is 50-110 ℃, and the gelatinization time is 1-24 hours.
Further, in the step 2), the complex enzyme is formed by mixing hemicellulase, laccase, alpha-amylase and acid protease.
Further, in the step 2), the mass ratio of the hemicellulase to the laccase to the alpha-amylase to the acid protease in the complex enzyme is 5:3:2:1.
Further, in the step 2), the dosage of the complex enzyme is 0.5-2% of the mass of the cat beans;
further, in the step 2), the fermentation temperature is 50-60 ℃.
Further, in the step 2), the usage amount of the sweet wine yeast is 3-5% of the mass of the cat beans.
Further, in the step 2), the acidic aqueous solution is selected from one of hydrochloric acid, sulfuric acid, phosphoric acid and acetic acid solution.
In summary, due to the adoption of the technical scheme, the beneficial effects of the invention are as follows:
(1) The method has the advantages of simple process, convenient operation and low cost, and the content of the levodopa in the obtained cat bean levodopa product reaches more than 99.2 percent, thus being suitable for industrial production.
(2) The invention does not use toxic reagent and has no pollutant emission, thereby achieving the aim of clean production.
(3) The invention can obtain ethanol at the same time, and improves economic benefit.
[ detailed description ] of the invention
Example 1
A method for extracting levodopa from cat beans, comprising the steps of:
1) Crushing: pulverizing semen Canavaliae into 80 mesh;
2) Extracting: adding 6 times of hydrochloric acid solution with the pH of 1.5 into the crushed cat bean raw material, gelatinizing for 3 hours at 80 ℃, cooling, adding sweet wine yeast and complex enzyme, and fermenting for 48 hours at 50-60 ℃ to obtain fermentation liquor; the complex enzyme is formed by mixing hemicellulase, laccase, alpha-amylase and acid protease; the mass ratio of the hemicellulase to the laccase to the alpha-amylase to the acid protease in the compound enzyme is 5:3:2:1; the dosage of the complex enzyme is 1% of the mass of the cat beans; the dosage of the sweet wine yeast is 4% of the mass of the cat beans;
3) And (3) crystallization: adding acid into the fermentation liquor to adjust the pH value to 2, filtering, adding 2 times of water into filter residues to adjust the pH value to 2, filtering, combining filtrate and concentrating to obtain 34% ethanol, standing the concentrated liquor for crystallization to obtain a crude levodopa product; the acid is selected from one of hydrochloric acid, sulfuric acid, phosphoric acid and acetic acid;
4) And (5) recrystallizing: filtering the crude product, adding ionized water to dissolve completely, adjusting pH to 3.5, adding 0.5% active carbon for decolorization, filtering, concentrating to 1/2 of the original volume, and crystallizing to obtain the L-dopa with purity of more than 99.2%.
The content of levodopa obtained in this example was 99.2%.
Example 2
A method for extracting levodopa from cat beans, comprising the steps of:
1) Crushing: pulverizing semen Canavaliae into 14 mesh;
2) Extracting: adding acetic acid solution with pH value of 2.5 and 3 times of total weight of the crushed cat bean raw material, gelatinizing for 2 hours at 100 ℃, cooling, adding sweet wine yeast and complex enzyme, and fermenting for 36 hours at 50-60 ℃ to obtain fermentation liquor; the complex enzyme is formed by mixing hemicellulase, laccase, alpha-amylase and acid protease; the mass ratio of the hemicellulase to the laccase to the alpha-amylase to the acid protease in the compound enzyme is 5:3:2:1; the dosage of the complex enzyme is 2% of the mass of the cat beans; the dosage of the sweet wine yeast is 3% of the mass of the cat beans;
3) And (3) crystallization: adding acid into the fermentation liquor to adjust the pH value to 2, filtering, adding 1 time of water into filter residues to adjust the pH value to 2, filtering, combining filtrate and concentrating to obtain 55% ethanol, standing the concentrated liquor for crystallization to obtain a crude levodopa product; the acid is selected from one of hydrochloric acid, sulfuric acid, phosphoric acid and acetic acid;
4) And (5) recrystallizing: filtering the crude product, adding ionized water to dissolve completely, adjusting pH to 3.5, adding 0.1% active carbon for decolorization, filtering, concentrating to 1/2 of the original volume, and crystallizing to obtain the L-dopa with purity of more than 99.2%.
The content of levodopa obtained in this example was 99.5%.
Example 3
A method for extracting levodopa from cat beans, comprising the steps of:
1) Crushing: pulverizing semen Canavaliae into 300 mesh;
2) Extracting: adding 10 times of sulfuric acid solution with pH of 4 into the crushed cat bean raw material, gelatinizing for 2.5 hours at 90 ℃, cooling, adding sweet wine yeast and complex enzyme, and fermenting for 72 hours at 50-60 ℃ to obtain fermentation liquor; the complex enzyme is formed by mixing hemicellulase, laccase, alpha-amylase and acid protease; the mass ratio of the hemicellulase to the laccase to the alpha-amylase to the acid protease in the compound enzyme is 5:3:2:1; the dosage of the complex enzyme is 0.5% of the mass of the cat beans; the dosage of the sweet wine yeast is 5% of the mass of the cat beans;
3) And (3) crystallization: adding acid into the fermentation liquor to adjust the pH value to 2, filtering, adding 3 times of water into filter residues to adjust the pH value to 2, filtering, combining filtrate and concentrating to obtain 20% ethanol; standing the concentrated solution for crystallization to obtain a crude levodopa product; the acid is selected from one of hydrochloric acid, sulfuric acid, phosphoric acid and acetic acid;
4) And (5) recrystallizing: filtering the crude product, adding ion water to dissolve completely, adjusting pH to 3.5, adding 20% active carbon for decolorizing, filtering, concentrating to 1/2 of the original volume, and crystallizing to obtain L-dopa with purity of more than 99.2%.
The content of levodopa obtained in this example was 99.8%.
In order to illustrate the technical effects of the present invention, the present invention provides the following comparative examples:
comparative example 1:
comparative example 1 differs from example 1 only in that: the soaking liquid in the step 2) is not added with sweet wine yeast;
the method comprises the following steps:
2) Extracting: adding 6 times of hydrochloric acid solution with pH value of 1.5 into the crushed cat bean raw material, gelatinizing for 3 hours at 80 ℃, cooling, adding complex enzyme, and fermenting for 48 hours at 50-60 ℃ to obtain fermentation liquor; the complex enzyme is formed by mixing hemicellulase, laccase, alpha-amylase and acid protease; the mass ratio of the hemicellulase to the laccase to the alpha-amylase to the acid protease in the compound enzyme is 5:3:2:1; the dosage of the complex enzyme is 1% of the mass of the cat beans; the dosage of the sweet wine yeast is 4% of the mass of the cat beans.
Results: the levodopa content of comparative example 1 was only 91.6% and no ethanol was obtained upon concentration.
Comparative example 2:
comparative example 2 differs from example 1 only in that: no complex enzyme is added into the soaking solution in the step 2).
The method comprises the following steps:
2) Extracting: adding 6 times of hydrochloric acid solution with pH value of 1.5 into the crushed cat bean raw material, gelatinizing for 3 hours at 80 ℃, cooling, adding sweet wine yeast and complex enzyme, fermenting for 48 hours at 50-60 ℃, adding dry yeast, and fermenting at 50-60 ℃ to obtain fermentation liquor; the dosage of the sweet wine yeast is 4% of the mass of the cat beans.
Results: the levodopa content of comparative example 2 was only 87.2%.
Comparative example 3:
comparative example 3 differs from example 1 only in that: the complex enzyme added into the soaking solution in the step 2) does not comprise laccase;
the method comprises the following steps:
2) Extracting: adding 6 times of hydrochloric acid solution with pH value of 1.5 into the crushed cat bean raw material, gelatinizing for 3 hours at 80 ℃, cooling, adding sweet wine yeast and complex enzyme, and fermenting for 48 hours at 50-60 ℃ to obtain fermentation liquor; the complex enzyme is formed by mixing hemicellulase, alpha-amylase and acid protease; the mass ratio of the hemicellulase to the alpha-amylase to the acid protease in the complex enzyme is 5:2:1; the dosage of the complex enzyme is 1% of the mass of the cat beans; the dosage of the sweet wine yeast is 4% of the mass of the cat beans.
Results: the levodopa content of comparative example 3 was only 90.3%.
Comparative example 4
Comparative example 4 differs from example 1 only in that: the complex enzyme added into the soaking solution in the step 2) does not comprise acid protease;
the method comprises the following steps:
2) Extracting: adding 6 times of hydrochloric acid solution with pH value of 1.5 into the crushed cat bean raw material, gelatinizing for 3 hours at 80 ℃, cooling, adding sweet wine yeast and complex enzyme, and fermenting for 48 hours at 50-60 ℃ to obtain fermentation liquor; the complex enzyme is formed by mixing hemicellulase, laccase and alpha-amylase; the mass ratio of the hemicellulase to the laccase to the alpha-amylase in the compound enzyme is 5:3:2; the dosage of the complex enzyme is 1% of the mass of the cat beans; the dosage of the dry yeast is 4% of the mass of the cat beans.
Results: the levodopa content of comparative example 4 was only 87.9%.
It can be seen from this:
(1) The complex enzyme adopted in the fermentation process and the dry yeast produce a synergistic effect, so that the content of the levodopa in the product is higher, ethanol is obtained by adding the sweet wine yeast, and the economic benefit is improved.
(2) The compound enzyme of the invention adopts the combination of hemicellulase, laccase, alpha-amylase and acid protease, and the content of levodopa in the product is higher than that of the compound enzyme adopting only three of the hemicellulase, laccase, alpha-amylase and acid protease.
The foregoing description is directed to the preferred embodiments of the present invention, but the embodiments are not intended to limit the scope of the invention, and all equivalent changes or modifications made under the technical spirit of the present invention should be construed to fall within the scope of the present invention.

Claims (8)

1. A method for extracting levodopa from cat beans, comprising the steps of:
1) Crushing: pulverizing semen Canavaliae into 14-300 mesh;
2) Extracting: adding an acidic aqueous solution with the weight which is 3-30 times of the total weight of the crushed cat bean raw material, heating to gelatinize, cooling, adding sweet wine yeast and complex enzyme, and fermenting to obtain a fermentation liquor; the complex enzyme is formed by mixing hemicellulase, laccase, alpha-amylase and acid protease;
3) And (3) crystallization: adding acid into the fermentation liquid to adjust the pH value to 2, filtering, adding 1-3 times of water into filter residues, adjusting the pH value to 2, filtering, combining filtrate, concentrating, and recovering to obtain ethanol; standing the concentrated solution for crystallization to obtain a crude levodopa product;
4) And (5) recrystallizing: filtering the crude product, adding ion water to dissolve completely, adjusting pH to 3.5, adding 0.1-20% active carbon for decolorizing, filtering, concentrating to 1/2 of the original volume, and crystallizing to obtain L-dopa with purity of more than 99.2%.
2. The method according to claim 1, wherein in step 2) the pH of the acidic aqueous solution is 1-4.
3. The method according to claim 1, wherein in step 2), the temperature of the thermal gelatinization is 50-110 degrees and the gelatinization time is 1-24 hours.
4. The method according to claim 1, wherein in step 2) the mass ratio of hemicellulase, laccase, alpha-amylase and acid protease in the complex enzyme is 5:3:2:1.
5. The method according to claim 1, wherein in the step 2), the amount of the complex enzyme is 0.5 to 2% by mass of the cat bean.
6. The method according to claim 1, wherein in step 2), the fermentation temperature is 50 to 60 ℃.
7. The method according to claim 1, wherein in step 2), the amount of the sweet wine yeast is 3-5% of the mass of the cat beans.
8. The method according to claim 1, wherein in step 2), the acidic aqueous solution is selected from one of hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid solution.
CN201910539636.6A 2019-06-19 2019-06-19 Method for extracting levodopa from cat beans Active CN112110826B (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104480171A (en) * 2014-11-21 2015-04-01 南宁知本康业生物技术有限公司 Method for extracting polypeptide from velvet bean residue
CN106946721A (en) * 2017-03-30 2017-07-14 湖南华诚生物资源股份有限公司 A kind of method for extracting high-purity tyrosine and levodopa in the beans from cat simultaneously
CN109081787A (en) * 2018-09-28 2018-12-25 那坡康正天然植物提取有限责任公司 A kind of technique for extracting levodopa from multitude's beans

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104480171A (en) * 2014-11-21 2015-04-01 南宁知本康业生物技术有限公司 Method for extracting polypeptide from velvet bean residue
CN106946721A (en) * 2017-03-30 2017-07-14 湖南华诚生物资源股份有限公司 A kind of method for extracting high-purity tyrosine and levodopa in the beans from cat simultaneously
CN109081787A (en) * 2018-09-28 2018-12-25 那坡康正天然植物提取有限责任公司 A kind of technique for extracting levodopa from multitude's beans

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