CN110229204A - A kind of compound PGHG preparation method treated in Parkinson disease drug - Google Patents
A kind of compound PGHG preparation method treated in Parkinson disease drug Download PDFInfo
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- CN110229204A CN110229204A CN201910458658.XA CN201910458658A CN110229204A CN 110229204 A CN110229204 A CN 110229204A CN 201910458658 A CN201910458658 A CN 201910458658A CN 110229204 A CN110229204 A CN 110229204A
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- 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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- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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Abstract
The invention discloses a kind of compound PGHG preparation methods treated in Parkinson disease drug, penthorum chinense pursh stem dried powder: 70% ethyl alcohol (1:25) ultrasonic extraction, it is successively extracted with petroleum ether, ethyl acetate, extract liquor is concentrated under reduced pressure, is freeze-dried to obtain penthorum chinense pursh stem polyphenol segment (PSE)；PSE is through isolated A, B flow point of high speed adverse current chromatogram (HSCCC), A flow point is further purified using preparative HPLC, efflux is collected according to chromatographic peak manually, monomeric compound is obtained after reduced pressure, purity reaches 99%, is accredited as PGHG through mass spectrum and nuclear-magnetism.The SH-SY5Y cellular ATP levels that PSE and PGHG can obviously inhibit 6- hydroxyl dopamine to induce reduce, and improve cell viability.Wherein PGHG can pass through the expression of activation Nrf2/HO-1 anti-oxidant access modulating apoptosis albumen and inflammatory protein.The neuroprotection has remarkable result in preventing and treating Parkinson disease.
Description
Technical field
The present invention relates to pharmaceutical technology field more particularly to a kind of compound PGHG systems treated in Parkinson disease drug
Preparation Method.
Background technique
Parkinson's disease (Parkinson ' sdisease, PD) be only second to alzheimer's disease it is second-biggest-in-the-world it is chronic into
Row sexual centre the nervous system disease threatens the health of more than 600 ten thousand people of the world.The clinical manifestation of PD includes bradykinesia, position
Unstable, tranquillization tremble with it is stiff, and the neurological susceptibility of memory disorders and behavior change is increased.The morbidity of PD and population are aged
Change closely related.With being further exacerbated by for China's aging, the disease incidence of PD is continuously increased, and is come to society and economy-zone serious
Harm.But it there is no definite effective intervention and treatment method at present.Therefore, the health threat generated in face of PD, treats it
Research and development with drug have become one of emphasis and the hot spot of world medicine area research.
Penthorum chinense pursh (Penthorum chinense Pursh.) also known as Chinese penthorum herb, adina pull root vegetables etc., are kiss-mes
Section (Saxifragaceae) penthorum (Penthorum Gronov.ex L.) plant pulls the aerial part of root vegetables.Penthorum chinense pursh
First recorded in Ming Dynasty's herbal for Relief of Famines, be distributed mainly on the ground such as China North China, East China, Central-South and Shaanxi, Sichuan and Guizhou, main product in
Sichuan Gulin County is Miao ethnic group, China medicinal herbs most in use.Penthorum chinense pursh belongs to the plant of civil dual-purpose of drug and food, civil to be made tea with penthorum chinense pursh
The generation of prevention of liver disease.Penthorum chinense pursh is warm-natured, it is sweet in flavor, nontoxic, there is clearing heat and detoxicating, inducing diuresis to remove edema, promoting blood circulation, calming the liver, invigorating the spleen, Huang of dispelling
The effect of subcutaneous ulcer.In addition, having definite curative effect for acute and chronic hepatitis and various complication using it as GANSU KELI made of raw material.
Research shows that penthorum chinense pursh extract has good anti-oxidant, antitumor and antiviral efficacy.It for carbon tetrachloride, alcohol and
The inside and outside hepatic injury of the inductions such as tert-butyl hydroperoxide (t-BHP) has good protective effect.It is to Parkinson disease
There is not been reported for protective effect.The work of laboratory early period has obtained penthorum chinense pursh stem polyphenol segment, [3 "-O- does not have pinocembrin -7-O-
Infanticide acyl group -4 ", 6 "-(S)-hexahydroxy biphenyl diacyl]-β-D-Glucose glycosides (PGHG).In order to test and assess the present invention
The application potential of middle penthorum chinense pursh stem polyphenol segment and PGHG in terms of Parkinson disease protection, those skilled in the art establish 6-
Hydroxyl dopamine (6-OHDA) damages SH-SY5Y cell Parkinson disease model, and determines cell viability and ATP level.
Summary of the invention
The object of the invention is that providing a kind of change treated in Parkinson disease drug to solve the above-mentioned problems
Close object PGHG preparation method.
The present invention through the following technical solutions to achieve the above objectives:
The first aspect of the invention is related to providing the preparation method of PGHG: using high speed adverse current chromatogram (HSCCC) with just
Reversed rotary-die type separates PSE, obtains A, B flow point, is dissolved respectively with proper amount of methanol after reduced pressure, crosses 0.22 μm
PTFE filter membrane.Be further purified using preparative HPLC, chromatographic condition is as follows: chromatographic column be C18 column (250mm × 10mm,
5 μm), column temperature is set as 28 DEG C, with 100 μ L of 5mL/min sample introduction, is flowed respectively with 60% methanol and 55% methanol isocratic elution A, B
Point, using 280nm and 335nm as Detection wavelength, efflux is collected according to chromatographic peak manually, efflux is concentrated under reduced pressure, from A flow point
Obtain compound PGHG.
The second aspect of the invention is related to the penthorum chinense pursh stem polyphenol segment and PGHG in Parkinson disease protection
New opplication.
In order to detect the protective effect of the resulting penthorum chinense pursh stem polyphenol segment of the present invention and PGHG to Parkinson disease, will catch up with
Yellow grass stem polyphenol segment and PGHG are configured to the medical fluid of various concentration with culture medium respectively, for handling human glioma cell
SH-SY5Y cell observes medical fluid at different dosages to the SH-SY5Y cell pa of 6- hydroxyl dopamine (6-OHDA) induction respectively
The protective effect of the gloomy disease of gold.The result shows that penthorum chinense pursh stem polyphenol segment and PGHG can be significant alleviate caused by 6-OHDA
The reduction of SH-SY5Y cell viability and ATP level, and effect is better than positive control baicalein (Baicalein).Show to catch up with Huang
Grass blade polyphenol segment and PGHG have good potentiality in the drug of preparation treatment Parkinson disease.
For PGHG in the drug of preparation treatment Parkinson disease, the PGHG includes swashing to the protective effect of Parkinson disease
The anti-oxidant access of Nrf2/HO-1 living, lowers the expression of apoptotic proteins Caspase-3 and inflammatory protein NF κ B, COX-2.
The beneficial effects of the present invention are:
The present invention is a kind of compound PGHG preparation method treated in Parkinson disease drug, compared with prior art,
The present invention is accredited as PGHG through mass spectrum and nuclear-magnetism.The SH-SY5Y cell that PSE and PGHG can obviously inhibit 6- hydroxyl dopamine to induce
ATP level reduces, and improves cell viability.Wherein PGHG can be by activating the anti-oxidant access modulating apoptosis albumen of Nrf2/HO-1
With the expression of inflammatory protein.The neuroprotection has remarkable result in preventing and treating Parkinson disease.
Detailed description of the invention
Fig. 1 is the HSCCC separation figure of PSE；
Fig. 2 is the ESI-MS map of PGHG
Fig. 3 is the structural formula of PGHG
Fig. 4 is the influence diagram of PSE and PGHG to the 6-OHDA SH-SY5Y cell induced
In Fig. 4: the measurement of (A) cell viability；(B) ATP level measures
Fig. 5 is the influence that SH-SY5Y cellular oxidation, apoptosis and the inflammatory protein that PSE and PGHG induce 6-OHDA are expressed
Figure
In Fig. 5: (A) anti-oxidant GAP-associated protein GAP；(B) apoptosis and inflammatory protein
Specific embodiment
The present invention will be further explained below with reference to the attached drawings:
The separation method of embodiment 1:PGHG
The foundation of 1.1 separation methods
70% ethyl alcohol (solid-liquid ratio=1:25) of 25 times of volumes of penthorum chinense pursh stem dried powder is in 55 DEG C, under the conditions of 59kHz
Ultrasonic extraction is repeated twice, 40min/ times, is filtered after resulting filtrate merges and is concentrated under reduced pressure through Rotary Evaporators, is then added
200mL ultrapure water is resuspended, and is extracted according to volume ratio 1:1 with ethyl acetate (10 times), and reduced pressure is freeze-dried to obtain the final product
Penthorum chinense pursh stem polyphenol segment (PSE).
N-hexane-ethyl acetate-methanol-water (2:5:2:5, v/v/v/v) dicyandiamide solution is selected, upper phase is washed as mobile phase
De-, flow velocity 5.0mL/min, revolving speed 800rpm, just reversed rotary-die type, Detection wavelength 280nm, sample volume is 200mg (200mg
Sample is dissolved in phase on 20mL), equipment separation temperature is set as 28 DEG C, and under this separation condition, the retention rate of stationary phase is reachable
73.3%.Collect to obtain two flow points of A, B manually according to HSCCC separating spectrum (Fig. 1).
A, B flow point that HSCCC is separated to are concentrated to dryness, dissolved with a small amount of methanol, 0.22 μm of PTFE filter membrane is crossed, adopts
Be further purified with preparative HPLC, chromatographic condition is as follows: chromatographic column is C18 column (250mm × 10mm, 5 μm), and column temperature is set
Be set to 25 DEG C, with 100 μ L of 5mL/min sample introduction, respectively with 60% methanol and 55% methanol isocratic elution A, B flow point, with 280nm and
335nm is Detection wavelength, collects efflux manually according to chromatographic peak, and efflux is concentrated under reduced pressure, and monomer chemical combination is obtained from A flow point
Object I.
The Structural Identification of 1.2 compounds
Mass Spectrometry Conditions are as follows: electric spray ion source (ESI), orifice potential 30V, capillary voltage 0.8kV, probe temperature 600
DEG C, 126 DEG C of ion source temperature, liquid stream 0.4mL/min, using anion scan pattern, scanning range m/z150-900, acquisition
Rate is 10 points/second.
Nuclear-magnetism identification: the dried powder of compound is dissolved in the deuterated DMSO of 0.5mL, using nuclear magnetic resonance (1H-NMR and
13C-NMR) carry out Structural Identification.Concrete outcome is as follows:
Compound I: light brown to yellow powder, ESI-MS map are shown in that Fig. 2, m/z871.26 [M-H]-illustrate its molecular weight
For 872.26,1H-NMR (DMSO-d6,600MHz) δ ppm:7.53 (1H, s), 7.40 (4H, dt, J=19.6,7.0Hz), 6.88
(2H, s), 6.36 (1H, s), 6.28 (1H, s), 6.23 (2H, d, J=3.1Hz), 6.07 (1H, d, J=12.6Hz), 5.31
(2H, dt, J=19.4,8.4Hz), 5.09 (1H, d, J=9.8Hz), 4.81 (1H, t, J=10.0Hz), 3.63 (1H, m)
.13C-NMR(DMSO-d6,151MHz)δppm:167.97and167.39(HHDP-COO-),166.00(galloyl-COO-),
163.46(C-5),145.67(galloylC-3),138.97(HHDPC-6,6'),129.05(C-3',5'),127.17(C-
2',6'),119.51(galloyl C-1),109.42(galloylC-2,6),104.06(C-10),79.19(C-2),71.88
(C-5 "), 71.18 (C-2 "), 70.08 (C-4 "), 40.13 (C-3) above data with it is reported in the literature almost the same, therefore identify
Compound 11 is Pinocembrin-7-O- [3 "-O-galloyl-4 ", 6 "-(S)-hexahy-
droxydiphenoyl]-β-D-glucoside(PGHG).Structural formula is shown in Fig. 3.
Embodiment 2: the SH-SY5Y cell pa that penthorum chinense pursh polyphenol segment and PGHG induce 6- hydroxyl dopamine (6-OHDA)
The intervention effect of the gloomy disease of gold
The detection of 2.1 cell viabilities
By SH-SY5Y cell inoculation to 96 orifice plates, culture medium is added in control group and model group after 12h, and medicine group adds respectively
Enter 1,2,5,10 μ g/mL penthorum chinense pursh polyphenol segments (PSE), the processing of 1,2,5,10 μM PGHG and 20 μM of baicalein (Bai)
12h, then model group and medicine group are added 200 μM of 6-OHDA and handle 12h, and fresh culture medium is added in control group.Finally siphon away
Every boreliquid is added 100 μ L culture mediums (containing 10 μ LCCK-8) and is placed in incubator incubation, uses microplate reader under 450nm after 40min
Light absorption value is measured, calculate cell survival rate according to OD value: OD drug/OD is compareed.
The detection of 2.2 ATP levels
By SH-SY5Y cell inoculation to 6 orifice plates, culture medium is added in control group and model group after 12h, and medicine group is separately added into
2,5,10 μ g/mL penthorum chinense pursh polyphenol segments (PSE) and 2,5,10 μM of PGHG handle 12h, and then model group and medicine group are added 200
μM 6-OHDA handles 12h, and fresh culture medium is added in control group.Culture solution is siphoned away, is collected into cell after being digested with pancreatin
In 1.5mL centrifuge tube, 2000rpm, 4 DEG C of centrifugation 7min siphon away supernatant, and 200 μ LRIPA lysates, vortex shake is added in cell precipitation
Cracking 15s is swung, 3 times, every minor tick 5min, last 15000rpm, 4 DEG C centrifugation 20min are cracked, supernatant is collected, according to ATP content
The operation reaction of assay kit specification, light absorption value is finally measured at 636nm, calculates each group ATP content.
2.3 results and analysis
By Fig. 5 A it is found that the SH-SY5Y cell that 5 μ g/mLPSE and 5 μM of PGHG can inhibit 6-OHDA to induce well is lived
The reduction of power, and required concentration will be far below positive control baicalein, and it is bright to show that PSE and PGHG have in patron saint classical prescription face
Aobvious advantage.Since 6-OHDA can be such that nerve cell ATP level declines, so have detected the level of intracellular ATP.As a result table
Bright PSE and PGHG can with conspicuousness increase the reduction (Fig. 4 B) of SH-SY5Y cellular ATP levels caused by 6-OHDA, show it
Can be synthesized with increase line mitochondrial energetics and slow down mitochondrial disorders caused by oxidative stress.In conclusion penthorum chinense pursh stem is more
Phenol segment and PGHG have good potentiality in the drug of preparation treatment Parkinson disease.
The influence of SH-SY5Y cellular anti-oxidant, apoptosis and inflammatory protein expression that embodiment 3:PGHG induces 6-OHDA
By SH-SY5Y cell inoculation to 60mm culture dish, after cell confluency degree reaches 70-80%, control group and model
Culture medium is added in group, and medicine group is separately added into 2,4,8 μM of PGHG processing 12h, and then 200 μM of 6- are added in model group and medicine group
OHDA handles 12h, and fresh culture medium is added in control group.Siphon away culture solution, after being digested with pancreatin by cell be collected into 1.5mL from
In heart pipe, 2000rpm, 4 DEG C of centrifugation 7min siphon away supernatant, and 200 μ LRIPA lysates, vortex concussion cracking is added in cell precipitation
15s cracks 3 times, every minor tick 5min, last 15000rpm, 4 DEG C centrifugation 20min, collects supernatant, the examination of BCA determination of protein concentration
Agent box measures protein concentration, and 5xloadingbuffer is added according to the ratio of 4:1 after leveling, boils, SDS-PAGE albumen electricity
Swimming, transferring film are incubated for Nrf2, HO-1, and 4 DEG C of primary antibody of NF κ B, COX-2, Caspase-3, β-Actin, GAPDH overnight, washes after film often
Temperature is incubated for secondary antibody 1h, develops finally by gel imaging system.
The result shows that PGHG can with concentration dependent raise the expression (Fig. 5 A) of Nrf2 and HO-1, i.e. PGHG can swash
The anti-oxidant access of Nrf2 living.In addition, 6-OHDA can raise the expression of Caspase-3 with apoptosis-induced；And PGHG can pass through
It lowers the expression of Caspase-3 and raises the generation of the expression inhibiting apoptosis of anti-apoptotic proteins Bcl-2.And PGHG can be with
Inhibit the expression of inflammation related proteins NF κ B and COX-2 caused by 6-OHDA and then alleviates the generation (Fig. 5 B) of inflammation.
The penthorum chinense pursh stem place of production used in the present embodiment is Sichuan Province China, is bought in Sichuan Province, sweet osmanthus township, Gulin County minister phase penthorum chinense pursh
Crop cultivation speciality cooperative society.Drug and reagent are purchased from Chengdu Ke Long chemical reagent factory.
Basic principles and main features and advantages of the present invention of the invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent thereof.
Claims (3)
1. a kind of compound PGHG preparation method treated in Parkinson disease drug, it is characterised in that: use high-speed counter-current color
It composes (HSCCC) and isolated A, B flow point is carried out to PSE with just reversed rotary-die type, dissolved respectively with proper amount of methanol after reduced pressure,
Cross 0.22 μm of PTFE filter membrane, be further purified using preparative HPLC, chromatographic condition is as follows: chromatographic column is C18 column
(250mm × 10mm, 5 μm), column temperature is set as 25 DEG C, with 100 μ L of 5mL/min sample introduction, respectively with 60% methanol and 55% methanol
Isocratic elution A, B flow point collects efflux, efflux decompression according to chromatographic peak using 280nm and 335nm as Detection wavelength manually
Concentration, obtains compound PGHG from A flow point.
2. a kind of new opplication of compound PGHG in preparation treatment Parkinson disease drug, it is characterised in that: penthorum chinense pursh stem is more
Phenol segment and PGHG include improving cell viability and ATP level to the therapeutic effect of Parkinson disease.
3. new opplication of the compound PGHG according to claim 2 in preparation treatment Parkinson disease drug, feature
Be: the PGHG includes the activation anti-oxidant access of Nrf2/HO-1 to the therapeutic effect of Parkinson disease, lowers apoptotic proteins
The expression of Caspase-3 and inflammatory protein NF κ B, COX-2.
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|---|---|---|---|---|
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| CN108904490A (en) * | 2018-06-28 | 2018-11-30 | 首都医科大学 | Application of the flavanone derivative in the drug for preparing anti-hepatic cell fattydegeneration in penthorum chinense pursh |
| CN109125337A (en) * | 2018-07-23 | 2019-01-04 | 澳门科技大学 | The application of penthorum chinense pursh and its compound in preparation treatment atherosclerosis and the drug for mitigating Alzheimer disease |
| CN109260239A (en) * | 2018-11-08 | 2019-01-25 | 西南医科大学 | Penthorum chinense pursh general flavone preparation method |
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2019
- 2019-05-29 CN CN201910458658.XA patent/CN110229204B/en active Active
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| CN103641871A (en) * | 2013-11-26 | 2014-03-19 | 中国人民解放军第二军医大学 | Macrocyclic polyphenol compound, and preparation and application thereof in pharmacy |
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| CN109125337A (en) * | 2018-07-23 | 2019-01-04 | 澳门科技大学 | The application of penthorum chinense pursh and its compound in preparation treatment atherosclerosis and the drug for mitigating Alzheimer disease |
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