CN112999254B - Isatis tinctoria leaf total alkaloid and extraction method and application thereof - Google Patents
Isatis tinctoria leaf total alkaloid and extraction method and application thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/31—Brassicaceae or Cruciferae (Mustard family), e.g. broccoli, cabbage or kohlrabi
- A61K36/315—Isatis, e.g. Dyer's woad
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/35—Extraction with lipophilic solvents, e.g. Hexane or petrol ether
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
Abstract
The invention relates to the technical field of medicines, relates to isatis tinctoria leaf total alkaloids and an extraction method thereof, and further relates to application of isatis tinctoria leaf total alkaloid extract in preparation of medicines or health-care products for treating Parkinson's disease. The preparation method of the invention comprises the following steps: 1): extracting; 2): eluting the extracting solution with strong acid type or weak acid type cation exchange resin by using deionized water, discarding the eluent, eluting 4-6 retention volumes by using 4-6% alkali, eluting 4-6 retention volumes by using ethanol with the pH of 2-3 and the concentration of 60-80%, and recovering the solvent to obtain crude extract of the isatis leaf total alkaloids; 3): dissolving the crude extract of the isatis indigotica leaf total alkaloids by using a formic acid solution, filtering, removing residues, and adjusting the pH value to 10-12 by using an alkali solution; 4): extracting the obtained alkali liquor with chloroform, and concentrating the extract to obtain total alkaloids of Isatis tinctoria leaves. The content of the prepared isatis leaf total alkaloids is more than 75%. And has obvious anti-PD effect.
Description
Technical Field
The invention relates to the technical field of medicines, relates to isatis tinctoria leaf total alkaloids and an extraction method thereof, and further relates to application of isatis tinctoria leaf total alkaloid extract in preparation of medicines or health-care products for treating Parkinson's disease.
Background
Parkinson's Disease (PD) is a common nervous system degenerative disease, and has the main clinical manifestations of motor symptoms such as resting tremor, muscular rigidity, bradykinesia and the like, and non-motor symptoms such as olfactory disorder, sleep disorder, cardiovascular dysfunction, intractable constipation and the like. PD is the second major neurodegenerative disease, the incidence rate increases year by year, and the number of PD affected people in China is estimated to be 494 ten thousands by 2030, which accounts for half of the world and brings heavy burden to families and society. The cause of PD is not clear so far, and the existing treatment methods and means have limitations and side effects. As a typical chronic disease of the old, the prevalence of Parkinson's disease is multiplied in the elderly population, 1-2% in the elderly population over 65 years old and 3-5% in the elderly population over 85 years old. Therefore, the development of the powerful anti-Parkinson disease drug has great social significance.
Isatis indigotica (Isatis indigotica) is a biennial herb plant of Isatis indigotica (Isatis L.) of Cruciferae, which is native to China and cultivated all over the country. Its dry leaves and roots can be used as medicine, the root is named as "isatis root", the leaves are named as "isatis leaf", it has the functions of clearing away heat and toxic material, cooling blood and removing macula, it is often used to treat wind-heat type common cold, sore throat, epidemic encephalitis B, hepatitis and parotitis. Alkaloids are the main chemical components of isatis indigotica fort leaves, and have various pharmacological activities including antibacterial, antiviral and antiendotoxin. No report of the anti-PD activity of the isatis leaf total alkaloids is found in the prior art.
Disclosure of Invention
One of the objects of the present invention is to provide total alkaloids extracted from the leaves of Isatis tinctoria L belonging to Isatis genus of Brassicaceae family.
The other purpose of the invention is to provide a preparation method of the isatis indigotica leaf total alkaloids.
The third purpose of the invention is to provide the application of the isatis indigotica leaf total alkaloids in preparing anti-PD drugs.
The preparation method of the isatis indigotica leaf total alkaloids provided by the invention comprises the following steps:
1): extraction: extracting dried Isatis tinctoria leaves with water or aqueous alcohol at room temperature or under reflux, filtering, mixing filtrates, and concentrating under reduced pressure to obtain Isatis tinctoria leaf extractive solution;
2): eluting the extracting solution with strong acid type or weak acid type cation exchange resin by using deionized water, discarding the eluent, eluting 4-6 retention volumes by using 4-6% alkali, eluting 4-6 retention volumes by using ethanol with the pH of 2-3 and the concentration of 60-80%, and recovering the solvent to obtain crude extract of the isatis leaf total alkaloids; ' Qiyi
3): dissolving the crude extract of the isatis indigotica leaf total alkaloids by using a formic acid solution, filtering, removing residues, and adjusting the pH value to 10-12 by using an alkali solution;
4): extracting the obtained alkali liquor with chloroform, and concentrating the extract to obtain total alkaloids of Isatis tinctoria leaves.
The aqueous alcohol in the step 1) is aqueous methanol or aqueous ethanol, the volume concentration of the aqueous alcohol is 60-75%, and the total volume of water or the aqueous alcohol is 5-10 times of the weight of the isatis indigotica leaves; reflux extraction times are 2-5 times, each time for 1.5-3 hr.
The strong acid type or weak acid type ion exchange resin in the step 2) is selected from one of a hydrogen 001X 7 type cation exchange resin, a D301 weak acid type cation exchange resin and an Amberlite IR-116 resin.
The alkali used for alkalization in the step 2) is ammonia water, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate or potassium carbonate, preferably ammonia water.
The pH value of the formic acid solution in the step 3) is 4-5, and the alkali solution is NaOH solution.
The content of the prepared isatis leaf total alkaloids is more than 75%.
MTT method proves that the isatis leaf total alkaloids have protection effect on SH-SY5Y cell damage induced by MPP +. After the treatment of the isatis indigotica leaf total alkaloids with the concentration of 12.5 mu M, the cell survival rate is improved by 8.4 percent compared with the MPP + treatment group. Therefore, the isatis indigotica leaf total alkaloids have the potential of preparing clinical anti-PD medicines.
The invention has the advantages that:
1. provides a new medical application of the isatis indigotica leaf total alkaloids in preparing anti-PD drugs, and has wide application prospect.
2. The woad is cultivated all over the country, and has rich sources, low price and easy obtainment.
3. The extraction and preparation process of the isatis tinctoria leaf total alkaloids is green, environment-friendly, simple and easy to implement.
Detailed Description
The present invention is described in detail below with reference to specific examples, but the use and purpose of these exemplary embodiments are merely to exemplify the present invention, and do not set forth any limitation on the actual scope of the present invention in any form, and the scope of the present invention is not limited thereto.
Example 1
Soaking 1Kg of dried Isatis tinctoria leaves in 10 times of 70 (v)% ethanol overnight, decocting for 3 hr, and filtering to obtain filtrate; decocting the residue with 7 times of 70% ethanol solution for 2 hr, filtering, and mixing filtrates; concentrating under reduced pressure to obtain extract. Eluting with 001 × 7 type ion exchange resin by a conventional method, removing impurities by using deionized water, eluting with 5% ammonia water for 4-5 retention volumes, eluting with 60-80% ethanol with pH of 2-3 for 4-6 retention volumes, and recovering the solvent to obtain crude extract of isatis tinctoria leaf total alkaloids. Dissolving the obtained crude extract of the isatis indigotica leaf total alkaloids by using a formic acid solution with the pH value of 2-3, filtering, removing residues, and adjusting the pH value to 10-12 by using a sodium hydroxide solution; the obtained alkali solution was extracted with chloroform, and chloroform was recovered to obtain 4.54g of isatis leaf total alkaloids. By ultraviolet-visible spectrophotometry, indirubin as reference substance, and measuring absorbance at 289nm wavelength, the detection result shows that the obtained total alkaloid content of Isatis tinctoria leaf is 83.5%.
Example 2
Soaking 1Kg of dried Isatis tinctoria leaves in 8 times of 75 (v)% ethanol overnight, decocting for 2 hr, and filtering to obtain filtrate; decocting the residue with 6 times of 75% ethanol solution for 1 hr, filtering, and mixing filtrates; concentrating under reduced pressure to obtain extract. Adding D301 weak acid type ion exchange resin according to a conventional method, eluting with deionized water to remove impurities, eluting with 5% ammonia water for 4-5 retention volumes, eluting with 60-80% ethanol with pH of 2-3 for 4-6 retention volumes, and recovering the solvent to obtain crude extract of isatis tinctoria leaf total alkaloids. Dissolving the obtained crude extract of the isatis indigotica leaf total alkaloids by using a formic acid solution with the pH value of 2-3, filtering, removing residues, and adjusting the pH value to 10-12 by using a potassium hydroxide solution; the obtained alkali solution was extracted with chloroform, and chloroform was recovered to obtain 4.16g of isatis leaf total alkaloids. By ultraviolet-visible spectrophotometry, indirubin as reference substance, and measuring absorbance at 289nm wavelength, the detection result shows that the obtained total alkaloid content of Isatis tinctoria leaf is 81.0%.
Example 3
Decocting 1Kg of dried Isatis tinctoria leaf with 5 times of 60 (v)% ethanol for 3 times each for 3 hr, filtering, mixing filtrates, and concentrating under reduced pressure to obtain Isatis tinctoria leaf extractive solution. Adding Amberlite IR-116 resin according to a conventional method, eluting with deionized water to remove impurities, eluting with 5% ammonia water for 4-5 retention volumes, eluting with 60-80% ethanol with pH of 2-3 for 4-6 retention volumes, and recovering the solvent to obtain crude extract of isatis indigotica leaf total alkaloids. Dissolving the obtained crude extract of the isatis indigotica leaf total alkaloids by using a formic acid solution with the pH value of 2-3, filtering, removing residues, and adjusting the pH value to 10-12 by using a calcium hydroxide solution; extracting the obtained alkaline solution with chloroform, and recovering chloroform to obtain 4.32g of Isatis tinctoria leaf total alkaloids. By ultraviolet-visible spectrophotometry, indirubin as reference substance, and measuring absorbance at 289nm wavelength, the detection result shows that the content of obtained folium Isatidis total alkaloids is 82.6%.
Example 4
Collecting 1Kg of dried Isatis tinctoria leaf, adding 10 times of 70 (v)% ethanol, reflux extracting for 3 times each for 1.5 hr, filtering, mixing ethanol extractive solutions, and concentrating under reduced pressure to obtain Isatis tinctoria leaf extractive solution. Adding Amberlite IR-116 resin according to a conventional method, eluting with deionized water to remove impurities, eluting with 5% ammonia water for 4-5 retention volumes, eluting with 60-80% ethanol with pH of 2-3 for 4-6 retention volumes, and recovering the solvent to obtain crude extract of isatis indigotica leaf total alkaloids. Dissolving the obtained crude extract of the isatis indigotica leaf total alkaloids by using a formic acid solution with the pH value of 2-3, filtering, removing residues, and adjusting the pH value to 10-12 by using a sodium hydroxide solution; extracting the obtained alkaline solution with chloroform, and recovering chloroform to obtain 4.80g of Isatis tinctoria leaf total alkaloids. By ultraviolet-visible spectrophotometry, indirubin as reference substance, and measuring absorbance at 289nm wavelength, the detection result shows that the obtained total alkaloid content of Isatis tinctoria leaf is 85.8%.
Example 5
MTT method for detecting the influence of the total alkaloid of isatis leaves prepared in example 4 on the activity of human neuroblastoma SH-SY5Y cells:
1. cell culture
Neuroblastoma SH-SY5Y cell line (purchased from American model culture Collection ATCC, Manassas, USA) was cultured in DMEM medium containing 10% FBS (purchased from Rockwell Hakkrong Hyclone, Logan, USA) at 37 ℃ in an incubator containing 5% CO2, and after 24h the cells were attached and the old culture medium was discarded.
2. Grouping of cells
Blank group: without any drug, only DMEM complete medium was used.
Model group: after the cells were cultured in DMEM complete medium for 4 hours, 1mM MPP + was added and the culture was continued for 36 hours.
Total alkali group: after the cells are cultured in DMEM complete culture solution for 4h, adding different concentrations (12.5. mu.M, 25. mu.M and 50. mu.M) of the isatis indigotica leaf total alkaloids to be cultured for 1 h, then adding 1mM MPP +, and continuing to culture for 36 h.
3. MTT assay
1) 20 μ L wells of MTT solution (0.5mg/mL) were added and incubation continued at 37 ℃ for 4 h.
2) The waste liquid is discarded, DMSO is added in a volume of 150. mu.L/well, and the mixture is shaken on a constant temperature shaker for 10 min.
3) Microplate reader (Thermo Scientific Multiskan MK3, Shanghai, China). The absorbance of each well was measured at 490 nm.
4. Statistical treatment
All results and data were confirmed in at least three independent experiments. All data results obtained are expressed as mean ± sd
One-way anova, P, was performed on each set of data using GraphPad Prism (california, usa) software<0.05 was considered statistically significant.
5. Results of the experiment
The results are shown in table 1, where the MPP + treated cells were significantly decreased in viability (P <0.001) compared to the blank group. Compared with a model group, the isatis leaf total alkaloids with different concentrations have better protection effect on SH-SY5Y cell injury induced by MPP +, and the cell survival rates are respectively improved by 4.9%, 9.5% and 13.7%.
TABLE 1 MPP + induced SH-SY5Y cell protection effect of Isatis tinctoria leaf total alkaloids
Example 6
Experiment on influence of isatis leaf total alkaloids on biological behaviors of 6-hydroxydopamine (6-hydroxydopamine, 6-OHDA) induced Parkinson disease rats:
1. materials and methods
1.1 materials
1.1.1 healthy adult 3-4 month old female SD rats with a mass between 200-250 g, provided by SPF grade laboratory animal center of Shenyang pharmaceutical university.
1.1.2 instrumental reagents (1)6-OHDA (purchased from Shanghai Yuye technology Co., Ltd.) (2) apomorphine (purchased from Qinghai pharmaceutical factory Co., Ltd.) (3) isatin leaf total alkaloids prepared by the above method (4) Bavishydrazine purchased from Shanghai Roche pharmaceutical Co., Ltd. (5) UMP2 type stereotaxic instrument purchased from American WPI (Co., Ltd.) (6) microinjector purchased from Shandong Yuwang group.
1.2 methods
1.2.1 preparation of animal models animals received a striatal unilateral injection 6-OHDA surgery 12h after fasting. Rats were anesthetized with an intraperitoneal injection of 10ml/kg of 3.6% chloral hydrate. After the rat falls asleep stably, the rat is fixed on a brain stereotaxic apparatus, and the ventral coordinates (1 mm behind bregma, 3mm on the left side of the midline, 4mm below the dura mater and 2 points of 6 mm) of the caudate putamen of the left striatum are determined as 6-OHDA injection sites by referring to a George rat brain stereotaxic map. Adjusting the brain stereotaxic apparatus, slowly lowering the injection needle to the dura mater, recording as 0mm, slowly inserting the needle downwards to reach the first injection site, and injecting 6-OHDA (2 μ g. mu.L)－1) Keeping the needle for 2min at 4 muL, lifting the injection needle by 2mm to reach the second injection point, injecting 4 muL of 6-OHDA, keeping the needle for 5min, and slowly withdrawing the needle. Sham operated animals were injected with equal amounts of normal saline. And after all the suture parts are withdrawn, local disinfection and suture are carried out.
1.2.2 rotational test 4 weeks after operation starts to subcutaneously inject 0.02% apomorphine 5ml/kg every week, rats begin to rotate to the opposite side of the injury (the right side in the experiment) about 2min, 30min is observed, the total number of revolutions in the rats within 30min is recorded, the average rpm is calculated, 4r/min or more and 7r/min or less after operation for 4 weeks is a partial success model, and 7r/min or more is a success PD rat model.
1.2.3 intervention and grouping selection of 60 successfully modeled PD rats, randomly dividing into a model group, a blank group (DMSO), a positive group (polyhydrazide) and a large, medium and small dose group of folium isatidis total alkaloids, and 10 rats in each group. Six groups of rats respectively receive normal saline, DMSO, poly-barnyardgrass hydrazine and different doses of isatis tinctoria leaf total alkaloid solution, and are injected into the abdominal cavity twice a day for two weeks. All drugs were made up into suspensions of the required concentration with 0.5% CMC-Na solution, stored in a refrigerator at 4 ℃ and pre-heated to 37 ℃ before use and shaken up. Dosage: large dose group: 100 mg/kg-1(ii) a The medium dose group: 50 mg/kg-1(ii) a Low dose group: 25 mg/kg-1(ii) a And (3) the rest: physiological saline, DMSO, and poly-barusine hydrazine solution with equal volume.
1.2.3 statistical processing data expressed as mean. + -. standard deviation (X. + -. S) were processed using SPSS13.0 software.
2. Results of the experiment
Compared with the blank group, the lateral rotation frequency of the PD rat in the model group is obviously increased (P < 0.01). After 24 days of administration, the lateral rolling frequency of rats in the polydiazine group and the isatis leaf total alkali dose group is obviously reduced compared with that in the model group (P is less than 0.01). The isatis leaf total alkaloids are prompted to have obvious improvement effect on apomorphine-stimulated circling behaviors in a rat model established by 6-OHDA. In the various dose groups of the isatis leaf total alkaloids, the middle dose group can reduce the lateral rolling frequency better than the large dose group and the small dose group, so that the influence of the isatis leaf total alkaloids on the biological behavior of the rat with the Parkinson disease induced by 6-OHDA is related to the dose. The results are shown in Table I.
Influence of Isatis tinctoria leaf total alkaloids on lateral circling frequency of PD rat
a, comparing with a blank group, wherein P is less than 0.01; and b, comparing the model group with P less than 0.01.
Claims (6)
1. The isatis tinctoria leaf total alkaloid is characterized in that the preparation method comprises the following steps:
1) extraction: extracting dried Isatis tinctoria leaves with aqueous alcohol at room temperature or under reflux, filtering, mixing filtrates, and concentrating under reduced pressure to obtain Isatis tinctoria leaf extract, wherein the aqueous alcohol is aqueous methanol or aqueous ethanol with volume concentration of 60-75%;
2) eluting the extracting solution with strong acid type or weak acid type cation exchange resin by using deionized water, discarding the eluent, eluting 4-6 retention volumes by using 4-6% alkali, eluting 4-6 retention volumes by using 60-80% ethanol, and recovering the solvent to obtain crude extract of the isatis leaf total alkaloids; the strong acid type or weak acid type cation exchange resin used is one of 001 × 7 type cation exchange resin in hydrogen form, D301 weak acid type cation exchange resin and Amberlite IR-116 resin;
3) dissolving the crude extract of the isatis indigotica leaf total alkaloids by using a formic acid solution, filtering, removing residues, and adjusting the pH value to 10-12 by using an alkali solution;
4) extracting the obtained alkali liquor with chloroform, and concentrating the extract to obtain total alkaloids of Isatis tinctoria leaves.
2. Isatis tinctoria leaf total alkaloids as claimed in claim 1, wherein: in the step 1), the total volume of the aqueous alcohol is 5-10 times of the weight of the isatis indigotica fort leaves; reflux extraction times are 2-5 times, each time for 1.5-3 hr.
3. Isatis tinctoria leaf total alkaloids as claimed in claim 1, wherein: the alkali in the step (2) is ammonia water, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate or potassium carbonate.
4. The Isatis tinctoria leaf total alkaloids according to claim 1, wherein the formic acid solution pH in step 3) is 4-5 and the alkaline solution is NaOH solution.
5. A pharmaceutical composition for treating Parkinson's disease, which is prepared from the isatis indigotica leaf total alkaloids in any one of claims 1 to 4 and a pharmaceutically acceptable carrier or excipient.
6. Use of the isatis tinctoria leaf total alkaloids according to any one of claims 1-4 or the pharmaceutical composition according to claim 5 in the preparation of an anti-parkinson's disease medicament.
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