CN102895278B - Application of arctinin and arctigenin in resisting parkinsonism - Google Patents
Application of arctinin and arctigenin in resisting parkinsonism Download PDFInfo
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Abstract
The invention discloses application of arctinin and arctigenin in the aspect of resisting parkinsonism, wherein the arctinin and the arctigenin are main active ingredients in traditional Chinese medicine burdock for resisting the parkinsonism. Shown by in vivo and in vitro test results, the arctinin and the arctigenin are stronger in effect of resisting the parkinsonism. The arctinin and the arctigenin in the traditional Chinese medicine burdock for resisting the parkinsonism are higher in activity in the aspect of resisting the parkinsonism, are small in side effect and low in price, and have better druggability.
Description
Technical field
The present invention relates to pharmacological action and the application thereof of two kinds of Chinese medicine monomer compositions, specifically take medicine and the application in preparing anti-Parkinson medicine thereof that Arctiin and aglycon be active component.
Background technology
Fructus Arctii be Compositae (Compositae) Arctium (Arctium) plant Fructus Arctii (
arctium lappa) dry mature fruit.The main pharmacodynamics composition of Fructus Arctii is Arctiin, our result of study (He Fan, Dou De-Qiang, Sun Yu, Zhu Lin, Xiao Hong-Bin, Kang Ting-Guo. Plasma pharmacokinetics and tissue distribution of arctiin and its main metabolite in rats by HPLC-UV and LC-MS. Planta Medica 2012,78:800-806.) and external report all show that Arctiin brings into play its drug effect by be metabolized to aretigenin in gastrointestinal tract.Parkinson disease (Parkinson ' s disease, PD) are to take the central nervous system degenerative disease that the gradual death of substantia nigra of midbrain dopaminergic neuron is pathological characters.Treatment means mainly be take Western medicine as main at present, but can only improve symptom, can not control its process, and prolonged application curative effect weakens and toxicity increases.
Summary of the invention
The object of the invention is to disclose the new purposes of a kind of Arctiin and aglycon, can be applied to the Parkinsonian medicine of preparation control.
Our result of study shows that aretigenin is the metabolite of Arctiin and the active component of absorbed into serum, and it is lower directly to take the bioavailability of aretigenin.Therefore the prodrug that Arctiin is aretigenin.First we find that by experiment in vitro aretigenin has good anti-Parkinson effect, then by experiment in body, finds that oral Arctiin shows that it has the effect of stronger anti-parkinson.Result of study proof Arctiin and aglycon all can be applicable to Parkinsonian treatment.For confirming that Arctiin and aglycon have the technical scheme that anti-parkinson adopts and be:
One, the preparation of Arctiin and aglycon:
1, the preparation method of Arctiin is to get Fructus Arctii coarse powder 1.0kg(Arctiin content 5.2%), use water boiling and extraction three times, add 15 times of water gagings, 1 hour at every turn.Merge extractive liquid,, is evaporated to 2 times of amounts of medical material, adds 95% ethanol to concentration of alcohol and reaches 80%, 4 ℃ of precipitate with ethanol 12 hours, filters, and gets supernatant, is evaporated near dryly, obtains extractum.Extractum dissolve with methanol, 100-120 order silica gel mixed sample by weight such as extractum 1, separated with the 200-300 order silica gel of the weight such as extractum 1, use chloroform-methanol eluting, obtain the fraction that contains Arctiin, merge the fraction that contains Arctiin, after concentrating, add 95% alcohol crystal, obtain Arctiin 30g (Arctiin content is greater than 95%).
2, the preparation method of aretigenin is to get Fructus Arctii coarse powder 1.0Kg(Arctiin content 5.2%), add 3 times of water gagings, 40 ℃ of temperature are incubated 4 hours, add 95% second alcohol and water and are adjusted to 10 times of amount 60% ethanol extracts, and reflux decocts 1 hour.Continue with 60% ethanol extraction twice, each 1 hour.Merge extractive liquid,, concentrated near dry.Separated through silicagel column, with 100 order silica gel, by sample size 1:1, mix sample, 200-300 order silica gel 1:1 carries out column chromatography, chloroform-methanol eluting merges the flow point that contains aretigenin, with ethyl alcohol recrystallization, obtains aretigenin 25g(aretigenin content and is greater than 95%).
Two,
the foundation of the cultivation of cell and PD cell model
1.1 experiment materials: dopaminergic Human neuroblastoma cell strain (SH-SY5Y cell is purchased from Chinese Academy of Sciences's Shanghai cell bank), Arctiin used and aglycon are taken from this laboratory.
1.2 cell culture: containing 10% deactivation calf serum (purchased from GIBCO company, 8166872), penicillin 100UmL lot number:
-1, streptomycin 100 μ gmL
-1(purchased from HyClone company, lot number: DMEM F-12 1:1 culture fluid J120721) (purchased from HyClone company, lot number: NXA0559) cultivate SH-SY5Y cell, be placed in 37 ℃, the incubator of 5%CO2.Change every other day culture fluid, when being cultured to cell monolayer approximately 80% and converging, the cultivation of going down to posterity, tests with the cell of exponential phase.
1.3 modelings and medication: regulate SH-SY5Y cell density approximately 5 * 10
4/ mL, 100 μ L/ holes are inoculated in 96 orifice plates, add respectively Arctiin and the aretigenin of variable concentrations (1 μ M, 5 μ M and 10 μ M) after 16h, and each concentration is established 3 multiple holes, and matched group (containing reagent treatment) and the model group of establishing equivalent (only add MPP
+, being purchased from Sigma company, lot number: 100M4713V), after 24h, matched group adds complete medium, model group and the every hole of blank group add the MPP with the 1mM of culture fluid dilution
+(1-methyl-4-phenylpyridinium ion).
1.4 tetramethyl azo azoles salt (MTT
+) method detection cell survival rate: after 48h, the every Kong Jun of cell does not add 5mg/mL MTT on the same group
+10 μ L, cultivate 4h, suck culture medium in hole, every hole adds DMSO 100 μ L, abundant dissolving to be crystallized, microplate reader detects the absorption value (OD value) (reference wavelength 620nm) in each hole, 490nm place, calculating cell survival rate [cell survival rate %=(experimental group OD value-blank group OD value/matched group OD value-blank group OD value) * 100%].
1.5 statistical procedures data with mean ± standard deviation (
± s) represent, with one factor analysis of variance (one-way ANOVA), carry out statistical procedures.The results are shown in Table 1.
SH-SY5Y cell survival rate after table 1 variable concentrations Arctiin and aglycon antagonism MPP+ cytotoxicity
Note: * with compare, variant (p<0.05); * and model group comparison, there were significant differences (p<0.001)
Three, the EXPERIMENTAL EXAMPLE of the anti-Parkinson effect of Arctiin
3.1 experiment materials: C57BL/6 mice is purchased from Dalian Medical Univ's zoopery center, and Arctiin used is self-control, and positive drug selegiline is produced by Shenzhen China Associated Pharmaceutical Co., Ltd..
3.2 animals groupings: 60 C57BL/6 mices are divided into six groups at random: blank group, model group, positive controls and basic, normal, high dosage Arctiin group (this laboratory self-control, purity > 95%), 10 every group.
3.3 modelings and medication: basic, normal, high dosage Arctiin group is administered once respectively every day, successive administration 13 days.Basic, normal, high dosage Arctiin group is administration 20mg/kg, 40mg/kg and 80mg/kg respectively, selegiline group administration 15mg/kg.With beginning in the 9th day after administration, model group, basic, normal, high dosage Arctiin group and selegiline group subcutaneous injection MPTP(1 monomethyl one 4 one phenyl 1,2,3, (1-methyl 4-phenyl tetrahydropyridine, is purchased from Sigma company, lot number to 6-tetrahydropyridine: 1001054803) 25 mg/kg, once a day, continuous 5 days.Blank group is with lumbar injection equivalent physiologic saline for substitute MPTP, once a day.Carry out Animal Behavior Science experiment exam every day simultaneously.
The examination of 3.4 behavioristicss
3.4.1 hang experiment (Traction test):
Object is to detect C57BL/6 mice limb motion to coordinate situation.Tested mice is hung in a horizontal wire, and the diameter of wire is about 0.2mm.From the two fore paws of mice, catch electric wire to start timing, the mice timing of dropping finishes.Within 25 seconds, above note is 6 minutes; 20-25 remembers 5 minutes second; 15-20 remembers 4 minutes second; 10-15 remembers 3 minutes second; 5-10s note 2 minutes; 0-5s note 1 minute.Situation the Epidemiological Analysis that takes statistics finally count the score.Score value is higher, and mice catches electric wire more firm; Illustrate that mice limb motion is coordinated situation better, otherwise, illustrate that the situations such as mice is trembled, myotonia are serious.The results are shown in Table 2.
Table 2 suspension experiment scores (
± s)
| ? | Dosage (mg/kg) | The 9th day | The 10th day | The 11st day | The 12nd day | The 13rd day |
| Blank group | -- | 7.00±0.00 | 6.47±1.20 | 6.04±1.44 | 5.98±1.26 | 5.07±1.72 |
| Model group | -- | 6.34±1.34 △ | 5.17±1.05 △ | 3.23±1.41 △△ | 2.94±1.57 △△ | 2.06±1.05 △△ |
| Positive controls | 15 | 6.75±0.76 | 6.07±1.46 ▲ | 5.83±1.47 ▲ | 5.35±1.26 ▲▲ | 4.37±1.32 ▲▲ |
| Low dose group | 20 | 5.96±0.10 | 4.95±1.25 | 3.42±1.96 | 3.83±1.47 ▲ | 3.03±1.85 ▲ |
| Middle dosage group | 40 | 6.00±0.72 | 4.88±1.29 | 3.51±1.21 ▲ | 4.06±1.30 ▲▲ | 3.32±1.12 ▲▲ |
| High dose group | 80 | 5.90±0.11 | 4.92±1.19 | 5.10±1.32 ▲▲ | 5.54±1.57 ▲▲■ | 4.16±0.88 ▲▲■ |
Note: △ compares with blank group, variant (p<0.05); △ △ compares with blank group, and there were significant differences (p<0.01); ▲ with model group comparison, variant (p<0.05), ▲ ▲ with model group comparison, there were significant differences (p<0.01); ■ and positive controls comparison, zero difference (p > 0.05)
3.4.2 pole-climbing experiment (Pole test):
Object is to detect C57BL/6 mice limb motion to coordinate situation.The cork ball that is 2.5cm by a diameter is fixed on a long 50cm, and the rod top of diameter 1cm is wrapped with gauze with anti-slip on rod, then tested mice is put on bead, and records mice and climbed the needed time of pole.Then by following standard, score: 0-3 completes the note 6 minutes of above-mentioned action in second; The note that 3-6 completed in second 5 minutes; The note that 6-9 completed in second 4 minutes; The note that 9-12 completed in second 3 minutes; The note that 12-15 completed in second 2 minutes; Within 15 seconds, above note is 1 minute.Situation the Epidemiological Analysis that takes statistics finally count the score.Score value is higher, and it is fewer that mice has climbed the whole process of the pole time used, illustrates that mice limb motion is coordinated situation better, also illustrates that mice is more and more skilled to pole-climbing experiment, the results are shown in Table 3.
Table 3 pole-climbing experiment scores (
± s)
| ? | Dosage (mg/kg) | The 9th day | The 10th day | The 11st day | The 12nd day | The 13rd day |
| Blank group | -- | 6.00±0.00 | 5.63±1.32 | 5.70±1.39 | 5.52±0.88 | 5.83±0.75 |
| Model group | -- | 5.05±0.48 | 3.83±1.04 △ | 3.38±1.41 △ | 3.20±1.12 △△ | 2.92±0.55 △△ |
| Positive controls | 15 | 4.96±1.02 | 4.32±1.05 | 4.20±0.94 ▲ | 4.38±0.71 ▲▲ | 4.13±0.65 ▲▲ |
| Low dose group | 20 | 4.60±0.62 | 3.91±0.36 | 3.42±0.63 | 3.70±0.76 ▲ | 3.13±0.47 ▲ |
| Middle dosage group | 40 | 4.46±0.11 | 3.97±1.31 | 3.98±0.91 ▲ | 3.53±0.76 ▲ | 3.29±0.93 ▲ |
| High dose group | 80 | 4.79±0.30 | 4.40±0.82 | 4.17±1.03 ▲▲■ | 3.99±0.87 ▲ | 4.09±0.47 ▲▲■ |
Note: △ compares with blank group, variant (p<0.05); △ △ compares with blank group, and there were significant differences (p<0.01); ▲ with model group comparison, variant (p<0.05); ▲ ▲ with model group comparison, there were significant differences (p<0.01); ■ and positive controls comparison, zero difference (p > 0.05)
3.4.3 swimming test (Swim test): object is to detect C57BL/6 mice limb motion to coordinate situation.The water tank of tested mice being put into 20 cm x 30cm * 20 cm specifications, water temperature is 22 ℃～25 ℃.Record the floating time of mice in 1min.Standards of grading are as follows: in 1min, and the note of flotation time in 10s 6 minutes; Note in 20s 5 minutes; Note in 30s 4 minutes; Note in 40s 3 minutes; Note in 50s 2 minutes; The note 1 minute that exceeds 50s.Situation the Epidemiological Analysis that takes statistics finally count the score.Score value is higher, and the time of mice swimming is longer; Illustrate that mice limb motion is coordinated situation better, otherwise, illustrate that the situations such as mice is trembled, myotonia are serious.The results are shown in Table 4.
Table 4 swimming test scores (
± s)
| ? | Dosage (mg/kg) | The 9th day | The 10th day | The 11st day | The 12nd day | The 13rd day |
| Blank group | -- | 6.00±0.00 | 5.80±0.05 | 5.680±0.32 | 6.00±0.60 | 6.00±0.38 |
| Model group | -- | 5.70±0.52 | 4.34±0.63 | 4.57±1.32 △ | 4.39±1.13 △△ | 3.85±0.96 △△ |
| Positive controls | 15 | 6.00±0.00 | 5.65±0.58 ▲ | 5.87±0.73 ▲▲ | 5.05±0.62 ▲ | 5.18±0.88 ▲▲ |
| Low dose group | 20 | 6.00±0.46 | 4.73±0.58 | 5.08±0.69 | 4.92±1.02 ▲▲ | 4.78±0.83 ▲ |
| Middle dosage group | 40 | 6.00±0.02 | 5.06±0.67 ▲ | 5.18±0.45 ▲ | 5.01±0.71 ▲▲ | 5.20±0.83 ▲▲■ |
| High dose group | 80 | 5.83±0.48 | 5.40±0.70 ▲ | 5.38±0.35 ▲▲ | 5.15±0.46 ▲▲■ | 5.04±0.45 ▲▲■ |
Note: △ compares with blank group, variant (p<0.05); △ △ compares with blank group, and there were significant differences (p<0.01); ▲ with model group comparison, variant (p<0.05); ▲ ▲ with model group comparison, there were significant differences (p<0.01); ■ and positive controls comparison, zero difference (p > 0.05)
Behavioristics's experimental result shows, middle dosage Arctiin group can strengthen the suspension exponential sum swimming index of mice, high dose Arctiin group can obviously strengthen suspension index, the pole-climbing exponential sum swimming index of mice, the be significantly improved effect of MPTP MODEL C 57BL/6 mice behavior of tool, its effect is suitable with the effect of positive control drug selegiline group.
Four, the study on mechanism experimental example of aretigenin anti-parkinson:
1. experiment material: dopaminergic Human neuroblastoma cell strain (SH-SY5Y cell is purchased from Chinese Academy of Sciences's Shanghai cell bank), aretigenin used is self-control.
2. cell culture: containing 10% inactivated fetal bovine serum, penicillin 100UmL
-1, streptomycin 100 μ gmL
-1dMEM F-12 1:1 culture fluid (purchased from HyClone company) cultivate SH-SY5Y cell, be placed in 37 ℃, the incubator of 5%CO2.Change every other day culture fluid, when being cultured to cell monolayer approximately 80% and converging, the cultivation of going down to posterity, tests with the cell of exponential phase.
3. modeling and medication: regulate SH-SY5Y cell density approximately 10
5/ mL, goes down to posterity in culture bottle, after being cultured to cell approximately 80% and converging, adds respectively Arctiin and the aretigenin of variable concentrations (1 μ M, 5 μ M and 10 μ M), and establishes matched group (containing reagent treatment) and model group (only adds MPP
+, be purchased from Sigma company, lot number: 100M4713V), after 24h, matched group adds complete medium and every bottle of MPP that adds 1mM of model group
+.
4.Western blotting detects related apoptosis protein level in cell
4.1 pro apoptotic protein caspase-3 levels
Extract and respectively organize cell whole protein (test kit is purchased from triumphant base), by BCA method, carry out protein quantification (test kit is purchased from Beyotim company), after sample treatment, each 10 μ L loading electrophoresis.By semidry method, carrying out transferring film, 5% defatted milk powder sealing, β-actin antibody (purchased from Zhong Shan Golden Bridge, lot number 111212 :) and Caspase-3(activated form) antibody (purchased from Beyotim company) presses 1:1000 and mixes with TBST, and 4 ℃ are spent the night.Wash away primary antibodie, respectively with horseradish peroxidase-labeled goat anti-mouse IgG (H+L) (1:2000) and (1:1000) incubated at room 2h of horseradish peroxidase-labeled goat anti-rabbit igg (H+L) (purchased from Beyotim company), wash away two anti-after, ECL chemiluminescence (purchased from Beyotim company), develop, the laggard line scanning of photographic fixing and analysis.Repeat to test 3 times.
4.2 anti-apoptotic proteins Bcl-2 and pro apoptotic protein Bax level
Protein sample treatment step is the same, after sealing, β-actin antibody, Bcl-2 antibody (purchased from abcam company, lot number: GR73243-1) and Bax antibody (purchased from abcam company, lot number: GR45349-3) press respectively 1:1000,1:500 and 1:1000 and mix with TBST, 4 ℃ are spent the night.Wash away primary antibodie, select corresponding horseradish peroxidase-labeled goat anti-rabbit igg (H+L) (1:1000) and (1:2000) incubated at room 2h of horseradish peroxidase-labeled goat anti-mouse IgG (H+L), wash away two anti-after, ECL chemiluminescence, develop, the laggard line scanning of photographic fixing and analysis.Repeat to test 3 times.
5. result
The results are shown in Table 5.The differential expression of matched group and model group Bcl-2, Bax and Caspase-3 albumen has system
Meter is learned meaning (p<0.05), SH-SY5Y cell after aretigenin is processed, can reduce the ratio of Bax/Bcl-2, reduce the expression of Caspase-3, show that aretigenin may raise Bax/Bcl-2 albumen and lower Caspase-3 albumen, and regulating degree and medicine are certain concentration dependent.
The impact of table 5 aretigenin on apoptosis-related protein expression in the rear SH-SY5Y cell of MPP+ induction
| ? | Bax/Bcl-2 | Caspase-3/β-actin |
| 1mM aretigenin | 132.85±0.06*** | 137.60±0.04* |
| 5mM aretigenin | 121.33±0.05*** | 131.23±0.02** |
| 10mM aretigenin | 116.33±0.07*** | 118.54±0.02*** |
| Model group | 152.21±0.07 △ | 162.87±0.03 △ |
| Matched group | 100±0.00 | 100±0.00 |
Note: △ and matched group comparison, variant (p<0.05); * with model group comparison, variant (p<0.05); * and model group comparison, there were significant differences (p<0.005); * * and model group comparison, have obvious significant difference (p<0.001)
Known in sum: Arctiin and aglycon all have the activity of anti-Parkinson, the activity of aretigenin is better than Arctiin, illustrates that the effect of aretigenin aspect anti-Parkinson is better than Arctiin.And experiment is also confirmed in body, Arctiin has significant anti-parkinson effect after being converted in vivo aretigenin.Because the toxic and side effects of Arctiin is low compared with aretigenin, than aretigenin, more easily absorb, be more suitable for the life-time service of disturbances in patients with Parkinson disease.
Claims (5)
1. Arctiin and the aglycon purposes in preparing antiparkinsonism drug, while it is characterized in that described Arctiin and aglycon purity are greater than 90%, can be used for preparation treatment parkinson disease medicine.
2. Arctiin according to claim 1 and the aglycon purposes in preparing antiparkinsonism drug, is characterized in that described Arctiin and aglycon are to be made by Fructus Arctii coarse powder, wherein:
The preparation method of Arctiin is as follows: get Fructus Arctii coarse powder 1.0 kg, Arctiin content 5.2%, uses water boiling and extraction three times, each 15 times of amounts, 1 hour;
Merge extractive liquid,, is evaporated to 2 times of amounts of medical material, adds 95% ethanol to concentration of alcohol and reaches 80%, 4 ℃ of precipitate with ethanol 12 hours, filters, and gets supernatant, is evaporated near dryly, obtains extractum;
Extractum dissolve with methanol, 100-120 order silica gel mixed sample by weight such as extractum, separated with the 200-300 order silica gel of the weight such as extractum, use chloroform-methanol eluting, obtain the fraction that contains Arctiin, merge the fraction that contains Arctiin, after concentrating, add 95% alcohol crystal, obtain Arctiin 30g, Arctiin content is greater than 90%;
The preparation method of aretigenin is as follows: get Fructus Arctii coarse powder 1.0Kg, Arctiin content 5.2%, adds 3 times of water gagings, 40 ℃ of temperature are incubated 4 hours, add 10 times of amount extracting solution that 95% second alcohol and water is adjusted to 60% ethanol content, and reflux decocts 1 hour, continue with 60% ethanol extraction twice, each 1 hour;
Merge extractive liquid,, concentrated near dry;
Separated through silicagel column, with 100 order silica gel, by sample size 1:1, mix sample, 200-300 order silica gel 1:1 carries out column chromatography, and chloroform-methanol eluting merges the flow point that contains aretigenin, and use ethyl alcohol recrystallization obtains aretigenin 25g, aretigenin content is greater than 93%.
3. Arctiin according to claim 1 and the aglycon purposes in preparing antiparkinsonism drug, is characterized in that adopting dopaminergic Human neuroblastoma cell strain model, proves that Arctiin and aglycon have the biological activity of anti-parkinson.
4. Arctiin according to claim 1 and the aglycon purposes in preparing antiparkinsonism drug, is characterized in that adopting the C57BL/6 mouse model due to MTPT, proves that Arctiin and aglycon have anti-parkinson effect.
5. Arctiin according to claim 1 and the aglycon purposes in preparing antiparkinsonism drug, it is characterized in that described arctiin and aglycon can be separately or with other drug applied in any combination in treatment of Parkinson disease.
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