CN106565802A - Radix paeoniae alba alcohol extract, 4-O-galloyl albiflorin and preparation and application of 4-O-galloyl albiflorin - Google Patents
Radix paeoniae alba alcohol extract, 4-O-galloyl albiflorin and preparation and application of 4-O-galloyl albiflorin Download PDFInfo
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- CN106565802A CN106565802A CN201610850345.5A CN201610850345A CN106565802A CN 106565802 A CN106565802 A CN 106565802A CN 201610850345 A CN201610850345 A CN 201610850345A CN 106565802 A CN106565802 A CN 106565802A
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- albiflorin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
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Abstract
The invention relates to 4-O-galloyl albiflorin, a preparation method of the 4-O-galloyl albiflorin and new application of the 4-O-galloyl albiflorin to preparing medicines with the beta-secretase inhibiting effect. The 4-O-galloyl albiflorin, the preparation method and the application are characterized in that the prepared medicines can be used for treating neurodegenerative diseases such as the Alzheimer's disease and stroke. The 4-O-galloyl albiflorin, the preparation method and the application aim at exploring the prospects of the beta-secretase inhibiting effect of the radix paeoniae alba alcohol extract and the 4-O-galloyl albiflorin, and a new medicinal field is exploited.
Description
Technical field：The present invention relates to root of herbaceous peony alcohol extract.Its preparation method and the acquired 4-O- galloyls root of herbaceous peony
Glycosides prepares the new application of the medicine of the inhibitory action of beta-secretase.
Background technology：Alzheimer's disease (Alzheimer's disease, AD) is the god being characterized with progressive dementia
One kind of Jing DDs, in being mainly in elderly population, is mainly shown as senile plaque expelling, the generation of neurofibrillary tangles and extensively
The neurological deficits of property.The deposition of intracerebral nerve internode condensed state amyloid-beta (β-amyloid, A β) forms senile plaque expelling and born of the same parents
The hyperphosphorylation of interior Protein tau forms the major pathologic features that nerve entanglement is acknowledged as AD.Recently research finds, insoluble
The generation and accumulation of A β is mainly amyloid precusor protein (APP) and shears through beta-secretase (BACE1) and gamma-secretase in succession
Product afterwards, starts neurovirulent cascade reaction then, causes oxidative stress, inflammatory reaction and irreversible neurotrosis
Occur.Therefore, suppress beta-secretase and gamma-secretase to mitigate the symptom of AD, enjoy in the medicine of research and development treatment AD and look steadily
Mesh.However, inhibitors of gamma-secretase is under development and encountering some and related to targeting (target-based) toxicity choosing
War, such as inhibitors of gamma-secretase are in Notch signal paths and other participation physiology and the effect on development associated protein substrate.
In contrast, in recent years the exploitation of beta-secretase inhibitor achieves gratifying achievements, shows targeting by force, Small side effects
Advantage.Therefore, beta-secretase has become the reliability of research and development prevention and treatment AD medicines as the rate-limiting enzyme during A β generations
Target spot.
The root of herbaceous peony (Paeonia lactiflora Pall.) also referred to as spends Chinese herbaceous peony, Ranunculaceae Chinese herbaceous peony platymiscium in vain.It is not only medicine
With plant (its root is used as medicine), or a kind of functional food, widely use in Asia, existing more than 2000 years history.As sight
The root of herbaceous peony of grass and food of admiring the beauty of flowers has many pharmacological actions, is mainly manifested in the aspects such as anti-freezing, antidepression, anti-oxidant and liver protection.
Through early stage work we obtained root of herbaceous peony alcohol extract, 4-O- galloyl albiflorin monomers and determined that it has suppression
The biologically active of beta-secretase
The content of the invention：
Goal of the invention：The invention provides root of herbaceous peony alcohol extract：The preparation method of 4-O- galloyl albiflorins；And its system
It is ready for use on the application of the newtype drugs of nerve degenerative diseases such as treatment alzheimer's disease, cerebral apoplexy.
Technical scheme：
A kind of root of herbaceous peony alcohol extract, 4-O- galloyl albiflorins, it is characterised in that：The 4-O- galloyls root of herbaceous peony
Glycosides is the compound shown in below formula：
Described root of herbaceous peony alcohol extract, the preparation method of 4-O- galloyl albiflorins, it is characterised in that：The method includes
Following steps：
(1) white Peony Root is taken, is extracted 3 times with the alcohol reflux of concentration of volume percent 60%, 80～90 DEG C of Extracting temperature, often
Secondary extraction time is two hours；
(2) ethanol in recycling step (1), obtains medicinal extract；
(3) medicinal extract is dispersed in water, extract extraction；
(4) by the extract Jing silica gel column chromatography methylene chloride-methanol gradient elutions in step (3), again Jing Sephadex
After LH-20 is separated, by preparing liquid phase, compound, as 4-O- galloyls albiflorin are obtained.
The preparation method of described 4-O- galloyl albiflorins, it is characterised in that：Sephadex in the step (4)
The detached flowing phase constituents of LH-20 and ratio are dichloromethane：Methyl alcohol=1:1.
Application of the described 4-O- galloyls albiflorin in the medicine for preparing treatment nerve degenerative diseases.
Described 4-O- galloyls albiflorin is preparing the application of the medicine for treating nerve degenerative diseases, its feature
It is：The nervus retrogression includes alzheimer's disease and cerebral apoplexy.
The detection method of root of herbaceous peony alcohol extract, 4-O- galloyls albiflorin to beta-secretase inhibitory action, its feature exists
In：The method is carried out according to the following steps：
(1) 10mL buffer solutions, 10mL BACE1,10mL substrate and 10mL measuring samples are dissolved in 10%DMSO, 25 DEG C
Lower lucifuge is incubated 60min, and the measuring samples are 2,10,50,100 μM/L4-O- galloyl albiflorins；
(2) its fluorescence intensity is surveyed by microwell plate spectral fluorometer, exciting light adopts 545nm, launching light to adopt 585nm, is surveyed
Measure inhibition percentage；
Formula is：Inhibition percentage (%)=1 ﹣ [(S60﹣ S0)/(C60﹣ C0)]×100
Wherein：C60For blank control group：The fluorescence intensity detected after enzyme, buffer solution, substrate incubation 60min；C0For sky
The fluorescence intensity that detection is obtained when white control group starts；S60The fluorescence intensity that detection group is detected after to be incubated 60min；S0For prison
The fluorescence intensity that survey group is detected when starting.
Advantage and effect：The present invention has excavated the root of herbaceous peony and 4-O- galloyl albiflorins and the like for A Erzi
DEVELOPMENT PROSPECT in terms of the nerve degenerative diseases pharmacy such as sea silent disease, cerebral apoplexy, has opened up a new medicinal applications.
Description of the drawings：
Fig. 1 is 4-O- galloyls albiflorin structural formula of the present invention；
Fig. 2 is result schematic diagram of the root of herbaceous peony alcohol extract to beta-secretase inhibitory action；
Fig. 3 is result schematic diagram of the 4-O- galloyls albiflorin to beta-secretase inhibitory action.
Specific embodiment：
The present invention is root of herbaceous peony alcohol extract, a kind of 4-O- galloyls albiflorin, it is characterised in that：The 4-O- nutgalls
Acyl group albiflorin is the compound shown in below formula：
The method for also including extracting 4-O- galloyl albiflorins from white Peony Root, the method is comprised the following steps：
(1) white Peony Root is taken, is extracted 3 times with the alcohol reflux of concentration of volume percent 60%, 80～90 DEG C of Extracting temperature, often
Secondary extraction time is two hours；
(2) ethanol in recycling step (1), obtains medicinal extract；
(3) medicinal extract is dispersed in water, extract extraction；
(4) by the extract Jing silica gel column chromatography methylene chloride-methanol gradient elutions in step (3), again Jing Sephadex
After LH-20 is separated, by preparing liquid phase, compound, as 4-O- galloyls albiflorin are obtained.
The preparation method of above-mentioned 4-O- galloyl albiflorins, Sephadex LH-20 are separated in the step (4)
Flowing phase constituent and ratio be dichloromethane：Methyl alcohol=1:1.
Also include application of the 4-O- galloyls albiflorin in terms of the medicine for the treatment of nerve degenerative diseases is prepared.
Described 4-O- galloyls albiflorin is preparing the application of the medicine for treating nerve degenerative diseases, its feature
It is：The nervus retrogression includes alzheimer's disease and cerebral apoplexy.
The present invention determines root of herbaceous peony alcohol extract, the 4-O- galloyl root of herbaceous peonys using FRET method (FRET methods)
Inhibitory action of the glycosides to beta-secretase (BACE1), as a result shows that root of herbaceous peony alcohol extract, 4-O- galloyls albiflorin have notable
Beta-secretase (BACE1) inhibitory action, therefore can be used for research and development treatment alzheimer's disease, the nerve such as cerebral apoplexy
The newtype drug of DD.
By embodiment come the present invention will be described：
Embodiment 1：
A kind of root of herbaceous peony alcohol extract as claimed in claim 1, the preparation method of 4-O- galloyl albiflorins, its feature
It is：White Peony Root is taken, with concentration of volume percent 80～90 DEG C of 60% ethanol refluxing extraction 3 times, 2 hours every time, ethanol is reclaimed,
Obtain medicinal extract (medicinal extract is root of herbaceous peony alcohol extract)；Medicinal extract is dispersed in water, extract extraction；By extract Jing silica gel column chromatographies
Methylene chloride-methanol gradient elution, again (methylene chloride-methanol=1 Jing after SephadexLH-20 separation:1), by preparation solution
Phase, obtains compound 1, learns to do section with reference to physicochemical property and Modern spectroscopy and identifies as 4-O- galloyl albiflorins.
Detection of the root of herbaceous peony alcohol extract to beta-secretase inhibitory action：
By 10mL buffer solutions, 10mL BACE1,10mL substrate and 10mL measuring samples (10,50,100, the 200mg/mL root of herbaceous peonys
Alcohol extract) 10%DMSO is dissolved in, lucifuge incubation 60min at 25 DEG C.Microwell plate spectral fluorometer surveys its fluorescence intensity, excites gloss
With 545nm, launching light adopts 585nm, surveys its inhibition percentage.Formula is as follows：Inhibition percentage (%)=1 ﹣ [(S60﹣ S0)/
(C60﹣ C0)]×100(C60Represent blank control group【Enzyme, buffer solution, substrate】The fluorescence intensity detected after incubation 60min；C0
The fluorescence intensity that detection is obtained when representing that blank control group starts；S60Represent that the fluorescence that detection group is detected after incubation 60min is strong
Degree；S0Represent the fluorescence intensity that monitoring group is detected when starting).
As a result it is as follows：The root of herbaceous peony alcohol extract of variable concentrations can with dose dependent suppression beta-secretase activity, as a result
As shown in Figure 2.
Detection of the 4-O- galloyls albiflorin to beta-secretase inhibitory action：
By 10mL buffer solutions, 10mL BACE1,10mL substrate and 10mL measuring samples, (2,10,50,100 μM/L 4-O- do not have
Infanticide acyl group albiflorin) 10%DMSO is dissolved in, lucifuge incubation 60min at 25 DEG C.Microwell plate spectral fluorometer surveys its fluorescence intensity,
Exciting light adopts 545nm, launching light to adopt 585nm, surveys its inhibition percentage.Formula is as follows：Inhibition percentage (%)=1 ﹣
[(S60﹣ S0)/(C60﹣ C0)]×100(C60Represent blank control group【Enzyme, buffer solution, substrate】What is detected after incubation 60min is glimmering
Luminous intensity；C0The fluorescence intensity that detection is obtained when representing that blank control group starts；S60Represent that detection group is detected after incubation 60min
Fluorescence intensity；S0Represent the fluorescence intensity that monitoring group is detected when starting).
As a result it is as follows：The 4-O- galloyls albiflorin of variable concentrations can be with the suppression beta-secretase of dose dependent
Activity, as a result as shown in Figure 3.
Claims (6)
1. a kind of root of herbaceous peony alcohol extract, 4-O- galloyl albiflorins, it is characterised in that：The 4-O- galloyls albiflorin
Compound shown in below formula：
2. a kind of root of herbaceous peony alcohol extract as claimed in claim 1, the preparation method of 4-O- galloyl albiflorins, its feature exists
In：The method is comprised the following steps：
(1) white Peony Root is taken, is extracted 3 times with the alcohol reflux of concentration of volume percent 60%, 80～90 DEG C of Extracting temperature, every time
Extraction time is two hours；
(2) ethanol in recycling step (1), obtains medicinal extract, i.e. root of herbaceous peony alcohol extract；
(3) medicinal extract is dispersed in water, extract extraction；
(4) by the extract Jing silica gel column chromatography methylene chloride-methanol gradient elutions in step (3), again Jing Sephadex LH-
After 20 separate, by preparing liquid phase, compound, as 4-O- galloyls albiflorin are obtained.
3. root of herbaceous peony alcohol extract according to claim 2, the preparation method of 4-O- galloyl albiflorins, its feature exists
In：The detached flowing phase constituents of Sephadex LH-20 and ratio are dichloromethane in the step (4)：Methyl alcohol=1:1.
4. root of herbaceous peony alcohol extract as claimed in claim 1,4-O- galloyls albiflorin are preparing treatment nervus retrogression disease
The application of the medicine of disease.
5. root of herbaceous peony alcohol extract according to claim 4,4-O- galloyls albiflorin are preparing treatment nervus retrogression
The application of the medicine of disease, it is characterised in that：The nerve degenerative diseases include alzheimer's disease and cerebral apoplexy.
6. a kind of root of herbaceous peony alcohol extract, detection method of the 4-O- galloyls albiflorin to beta-secretase inhibitory action, its feature
It is：The method is carried out according to the following steps：
(1) 10mL buffer solutions, 10mL BACE1,10mL substrate and 10mL measuring samples are dissolved in 10%DMSO, are kept away at 25 DEG C
Light is incubated 60min, and the measuring samples are 2,10,50,100 μM/L4-O- galloyl albiflorins；
(2) its fluorescence intensity is surveyed by microwell plate spectral fluorometer, exciting light adopts 545nm, launching light to adopt 585nm, measures
To inhibition percentage；
Formula is：Inhibition percentage (%)=1 ﹣ [(S60﹣ S0)/(C60﹣ C0)]×100
Wherein：C60For blank control group：The fluorescence intensity detected after enzyme, buffer solution, substrate incubation 60min；C0It is right for blank
According to the fluorescence intensity that obtains of detection when group starting；S60The fluorescence intensity that detection group is detected after to be incubated 60min；S0For monitoring group
The fluorescence intensity detected during beginning.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110898102A (en) * | 2019-09-10 | 2020-03-24 | 中国人民解放军北部战区总医院 | Cinnamon extract and traditional Chinese medicine compound for preventing and treating cold injury and application thereof |
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| CN1714797A (en) * | 2004-07-02 | 2006-01-04 | 中国科学院上海药物研究所 | The medical usage of paeoniflorin |
| CN101053598A (en) * | 2007-05-29 | 2007-10-17 | 深圳市生物谷科技有限公司 | Medicinal composition for treating cardio-cerebralvascular diseases and diabetes |
| CN102125575A (en) * | 2010-01-19 | 2011-07-20 | 张作光 | Application of albiflorin in resisting Parkinson's disease |
| CN102258588A (en) * | 2011-03-10 | 2011-11-30 | 张建军 | Preparation method of peony general glycoside |
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2016
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1714797A (en) * | 2004-07-02 | 2006-01-04 | 中国科学院上海药物研究所 | The medical usage of paeoniflorin |
| CN101053598A (en) * | 2007-05-29 | 2007-10-17 | 深圳市生物谷科技有限公司 | Medicinal composition for treating cardio-cerebralvascular diseases and diabetes |
| CN102125575A (en) * | 2010-01-19 | 2011-07-20 | 张作光 | Application of albiflorin in resisting Parkinson's disease |
| CN102258588A (en) * | 2011-03-10 | 2011-11-30 | 张建军 | Preparation method of peony general glycoside |
Non-Patent Citations (3)
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110898102A (en) * | 2019-09-10 | 2020-03-24 | 中国人民解放军北部战区总医院 | Cinnamon extract and traditional Chinese medicine compound for preventing and treating cold injury and application thereof |
| CN110898102B (en) * | 2019-09-10 | 2021-09-17 | 中国人民解放军北部战区总医院 | Cinnamon extract and traditional Chinese medicine compound for preventing and treating cold injury and application thereof |
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