CN107007637A - Application of the miracle fruit leaf extract in the medicine preparation for the treatment of alzheimer disease - Google Patents
Application of the miracle fruit leaf extract in the medicine preparation for the treatment of alzheimer disease Download PDFInfo
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- 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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- A61K2236/50—Methods involving additional extraction steps
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Abstract
The present invention provides a kind of miracle fruit leaf extract and is preparing the application in being used to treat the medicine of alzheimer disease.The miracle fruit leaf extract is extracted by following steps：Miracle fruit leaf is dried, crushed, miracle fruit leaf powder is obtained；The first alcoholic solution is added into the miracle fruit leaf powder, ultrasonic extraction is carried out, and supernatant is collected by centrifugation, residual residue is extracted at least twice in the same way again, merging supernatant is alcohol extract；The alcohol extract obtains miracle fruit Leave extract through vacuum distillation, freeze-drying；The miracle fruit Leave extract is dissolved in the water, and through macroporous resin treatment, then eluted with the second alcoholic solution eluant, eluent, alcohol eluen is collected；The alcohol eluen obtains miracle fruit leaf extract dry powder through vacuum distillation and freeze-drying.The miracle fruit leaf extract can substantially suppress nematode strain CL4176 paralysis, can be used for the preparation for treating the medicine and health products of alzheimer's disease.
Description
Technical field
The present invention relates to the application of miracle fruit leaf extract, more particularly to miracle fruit leaf extract prepare be used to treating Ah
Application in the medicine of Alzheimer's disease.
Background technology
Alzheimer disease (Alzheimer disease, AD), is called senile dementia, is a kind of central nervous system
Degenerative disease, insidious onset, the course of disease is in chronic progressive, is the most common type of senile dementia.It is mainly shown as progressive
Property the neuropsychic symptom such as memory disorders, cognition dysfunction, personality change and aphasis, have a strong impact on social, occupation with
Vital function.The AD cause of disease and pathogenesis is not yet illustrated, and characteristic pathological changes into β amyloid proteins and deposits to be formed extracellular
Neurofibrillary tangles in senile plaque expelling and the nerve cell of Protein tau Hyperphosphorylationof formation, and neuron loss is with colloid
Hyperplasia etc..
Because the AD cause of disease and pathogenesis are unknown, specific short is there is no at present, based on symptomatic treatment.The medicine used
Mainly there are choline, lecithin, eserine and cholinergic agonist etc., but these effect of drugs difference is totally different, can also produce evil
The side effects such as the heart, vomiting, transaminase rise, stove necrosis of liver cells and depression.
Miracle fruit (Synsepalum dulcificum Daniell) is a kind of peculiar fruit that Sapotaceae miracle fruit belongs to.
The fruit originates in West Africa torrid areas, is planted extensively in China tropical and subtropical region, throughout the year can result.
Its pulp contains the nutriments such as abundant peculiar glycoprotein, vitamin, organic acid, flavones, anthocyanidin.At this stage for mystery
The research of fruit shows that it has regulation blood pressure, blood fat, mitigates the effects such as gout, uric acid, headache.Miracle fruit leaf has treatment high
The effects such as blood pressure, diabetes and artery sclerosis, and hyperhydrochloria, enhancing hepato-biliary function and raising immunity can be improved.
The content of the invention
There is provided miracle fruit leaf extract for activity of the present invention based on the polyphenoils included in miracle fruit leaf extract
Application in preventing or treating the medicine preparation of alzheimer disease.According to the miracle fruit leaf extract of the present invention for A Er
Zi Haimo diseases have good prevention or therapeutic action, simultaneously because the natural anti-oxidation active component wherein included, it is to avoid
The side effects such as Nausea and vomiting, transaminase rise, stove necrosis of liver cells and depression, with excellent bioactivity and security.
Prepared according to an aspect of the present invention there is provided a kind of miracle fruit leaf extract for treating alzheimer disease
Medicine in application, the miracle fruit leaf extract extracted by following steps：Miracle fruit leaf is dried, crushed, god is obtained
Secret fruit leaf powder；The first alcoholic solution is added into the miracle fruit leaf powder, ultrasonic extraction is carried out, and supernatant is collected by centrifugation, it is remaining
Residue is extracted at least twice in the same way again, and merging supernatant is alcohol extract；The alcohol extract is through vacuum distillation, cold
Jelly is dried to obtain miracle fruit Leave extract；The miracle fruit Leave extract is dissolved in the water, and through macroporous resin treatment, then
Eluted with the second alcoholic solution eluant, eluent, collect alcohol eluen；The alcohol eluen is obtained through vacuum distillation and freeze-drying
Miracle fruit leaf extract dry powder.
Preferably, first alcoholic solution is 50~90% (v/v) methanol aqueous solutions.
According to an embodiment, the ratio of the miracle fruit leaf powder and first alcoholic solution is every gram of miracle fruit
Leaf powder uses the alcoholic solutions of 15~45mL first.
According to another embodiment, the time of the ultrasonic extraction is 0.5~1h, and the temperature of ultrasound bath is
40~60 DEG C.
Second alcoholic solution is 10~90% (v/v) ethanol water.
According to another embodiment, the macroreticular resin is AB-8.
Preferably, first it is eluted with water before being eluted with the alcohols eluant, eluent, eluent is given it up.
Had according to the miracle fruit leaf extract of the present invention to DPPH (1,1- diphenyl -2- hardships phenylhydrazine) free radical stronger
Scavenging activity (IC50For 83~120 μ g/mL), Scavenging activity is at least 2 times of Kaempferol；With higher iron ion reduction/resist
Oxidability (FRAP values are 6~8mM/g Trolox), at least the 2.5 of Kaempferol times.Above-mentioned miracle fruit leaf extract can
Substantially suppress nematode strain CL4176 paralysis, can be used for the preparation of anti-AD medicine and health products.
Brief description of the drawings
Fig. 1 shows polyphenoils in the miracle fruit leaf extract according to the present invention detected under 325nm wavelength
UPLC chromatograms.
Fig. 2 shows the paralysis under various concentrations to nematode strain CL4176 according to the miracle fruit leaf extract of the present invention
Inhibitory action.
Embodiment
The present invention provides a kind of miracle fruit leaf extract and is preparing the application in being used to treat the medicine of alzheimer disease,
The miracle fruit leaf extract is extracted by following steps：Miracle fruit leaf is dried, crushed, miracle fruit leaf powder is obtained；To described
The first alcoholic solution is added in miracle fruit leaf powder, ultrasonic extraction is carried out, and supernatant is collected by centrifugation, residual residue is again with same side
Formula is extracted at least twice, and merging supernatant is alcohol extract；The alcohol extract obtains miracle fruit through vacuum distillation, freeze-drying
Leave extract；The miracle fruit Leave extract is dissolved in the water, and through macroporous resin treatment, then eluted with the second alcoholic solution
Agent is eluted, and collects alcohol eluen；The alcohol eluen obtains miracle fruit leaf extract through vacuum distillation and freeze-drying and done
Powder.
Specifically, miracle fruit leaf is dried and crushed by conventional method, for example, dry naturally.Miracle fruit leaf after crushing is excellent
80 mesh sieves were gated, to obtain miracle fruit leaf powder.
Preferably, first alcoholic solution is 50~90% (v/v), preferably 60~80% (v/v) methanol aqueous solution.
The ultrasonic extraction frequency is 40000 hertz, and the time can be 0.5~1h, and the temperature of ultrasound bath is 40~60
℃。
, can not if extracting the first alcoholic solution of solution excessive concentration (i.e. more than 90% (v/v)) during ultrasonic extraction
Extract the larger active material of polarity；If it is too low (i.e. less than 50% (v/v)) to extract solution the first alcoholic solution concentration, have
Too many carbohydrate is extracted in extract, influences next step drying effect.
According to an embodiment, the ratio of the miracle fruit leaf powder and first alcoholic solution is every gram of miracle fruit
Leaf powder uses 15~45mL, the preferably alcoholic solutions of 30mL first.
According to another embodiment, the second alcoholic solution as eluant, eluent be 10~90% (v/v), preferably 30~
70% (v/v), more preferably 60% (v/v) ethanol water.
According to another embodiment, above-mentioned macroreticular resin can be AB-8.Preferably, in macroreticular resin separating step
In, the flow velocity of miracle fruit Leave extract solution is 1~3mL/min, preferably 1.5mL/min.
According to an embodiment, first it is eluted with water before being eluted with the second alcoholic solution eluant, eluent, abandons elution
Liquid, for removing the glucide in extract.
Above-mentioned freeze-drying step is carried out using conventional method and condition, and for example freeze-drying can be at subzero 35 ± 1 DEG C
At a temperature of carry out.
In said extracted method, using methanol aqueous solution as extractant, it is more easy to because its polarity is big, molecular weight is relatively low
Active material is extracted in into cell membrane.Meanwhile, extracted using ultrasonic assistant so that extraction time is short, it is simple to operate, obtained
Activity substance content is high in the product obtained.
Inoxidizability is had according to the miracle fruit leaf extract of the present invention, wherein active material is mainly polyphenol and flavonoids
Compound.Specifically, the miracle fruit leaf extract obtained according to the above method has stronger Scavenging activity to DPPH free radicals,
Such as IC50For 83~120 μ g/mL, preferably 100~120 μ g/mL, Scavenging activity is more than 2 times of Kaempferol；With higher
Iron ion reduction/oxidation resistance (FRAP), such as FRAP values are 6~8mM/g Trolox, preferably 6.5mM/g Trolox, are
More than 2.5 times of Kaempferol；Paralysis thus, it is possible to substantially suppress nematode strain CL4176, can be used for antioxidant and anti-AD
Medicine or health products preparation.
Following examples are that the present invention is further illustrated, rather than limitation of the present invention.
Embodiment
Embodiment 1：The preparation of miracle fruit leaf extract
Miracle fruit leaf is dried naturally, crushed, and crosses 80 mesh sieves, miracle fruit leaf powder is obtained；
50% (v/v) methanol aqueous solution is added with every gram of miracle fruit leaf powder 30mL amount into miracle fruit leaf powder, 40
DEG C bath temperature under, ultrasonic extraction 0.5h is collected by centrifugation supernatant, and residual residue is repeated to extract twice with identical condition,
Merge these supernatants and obtain alcohol extract；
By above-mentioned alcohol extract through 40 DEG C of vacuum distillations, at subzero 35 DEG C being freeze-dried 24h obtains miracle fruit leaf and slightly carries
Thing；
Above-mentioned miracle fruit Leave extract is dissolved in water to no particle, and through macroreticular resin AB-8 processing, first washed
Removing is miscellaneous, then with 60% (v/v) ethanol elution, collects eluent；
Above-mentioned alcohol eluen obtains miracle fruit leaf extract dry powder through 40 DEG C of vacuum distillations and subzero 35 DEG C of freeze-dryings.
Embodiment 2 to 3
Miracle fruit leaf extract dry powder is prepared according to step same as Example 1, difference is to divide in embodiment 2 and 3
Not Cai Yong 70% (v/v) methanol aqueous solution and 90% (v/v) methanol aqueous solution be used as extractant.
Comparative example 1
Miracle fruit leaf extract dry powder is prepared according to step same as Example 1, difference is in comparative example 1 to use water
It is used as extractant.
Total phenol, the measure of general flavone content in miracle fruit leaf extract
The drafting of total phenol standard curve.The standard sample of various concentrations is configured with 100mg/L gallic acid storing solution.It is accurate
Really pipette different volumes gallic acid titer, add 1mL forint phenol reagent (water in advance be diluted to original concentration ten/
One) it is 2mL that cumulative volume, is supplied with water.Room temperature adds 1.0mL sodium carbonate liquors (7.5%, w/v) after static 5 minutes, in dark
After middle reaction 30min absorbance is determined in 765nm.Wherein in standard sample the ultimate density of gallic acid be 0.1,0.2,0.5,
1.0th, 2.0 and 4.0mg/L.Total phenol content in sample is represented with the percentage (%) of same amount of gallic acid is reached.
The drafting of general flavone standard curve.Accurate weigh is dried to the control substance of Rutin 0.0100g of constant weight, with 60% (v/
V) ethanol solution is configured to 0.2mg/mL reference substance solution.It is accurate respectively to draw 0.0,1.0,2.0,4.0,6.0,8.0 and
10.0mL rutins standard liquid is diluted to 15mL in 25mL volumetric flasks with 60% (v/v) ethanol solution, adds 5% (w/v) sub-
Sodium nitrate solution 0.3mL, shakes up, and stands 5min.Then 10% (w/v) aluminum nitrate solution 0.3mL is added, is shaken up, 5min is stood.
1mol/L sodium hydroxide solution 2mL are added, is mixed, is diluted to scale with 60% (v/v) ethanol solution, is stored at room temperature 15min.
Using the first pipe as blank control, absorbance is determined at wavelength 510nm.General flavone content in sample is same amount of with reaching
The percentage (%) of rutin is represented.
The content and recovery rate of total phenol and general flavone are shown in the miracle fruit leaf extract that various concentrations methanol aqueous solution is extracted
Table 1.
Table 1
a：The measure carried out to alcohol extract
b：Relative to original miracle fruit leaf quality
c：The measure carried out to miracle fruit leaf extract dry powder
From result above, according to the recovery rate of the alcohol extract of embodiment 1 to 3 and total phenol, general flavone content, significantly
Higher than the content of the extract solution extracted in comparative example 1 with water.When methanol aqueous solution concentration is 70 volume %, alcohol extract is carried
Take rate and total phenol, general flavone content highest.
The measure of DPPH radical scavenging activities and iron ion reduction/determination oxidative (FRAP)
1mg/mL sample will be dissolved into according to the miracle fruit leaf extract dry powder of embodiment 1 to 3 and comparative example 1 with methanol
Carry out every determination oxidative.
With the bitter phenylhydrazine free radicals (DPPH, Sigma Co., USA) of 1,1- diphenyl -2- for reference material, DPPH free radicals are used
The method of Scavenging activity determines the oxidation resistance of above-mentioned miracle fruit leaf extract.
2mL DPPH solution (concentration is 0.5mM) is taken, each miracle fruit leaf extract methanol solution with 0.5mL is (dense respectively
Degree respectively 0.02,0.05,0.1,0.2,0.5,1mg/mL) mixing, lucifuge reacts 1h under 37 DEG C of constant temperature.In wavelength 525nm
Place determines absorbance.Thus the IC of miracle fruit leaf extract is calculated50Numerical value.
FRAP measure.FRAP is measured using kit.Take the above-mentioned miracle fruit leaf extract first after 10 times of dilution
The μ L of alcoholic solution sample 10 are added in 96 microwell plates, then add 2,4,6- tripyridyl triazines of 200 μ L Fresh
(TPTZ) working solution is mixed, and determines absorbance in 595nm after 37 DEG C of water-bath 30min, with various concentrations Trolox (0.15,
0.3rd, 0.6,0.9,1.2,1.5mM) do standard curve for reference material.Antioxidation activity (the FRAP of miracle fruit leaf extract sample
Value) same absorbance is reached with every gram of dry mass needed for Trolox mMs of number (mM Trolox/g) represent.Radicals scavenging
Ability and FRAP's the results are shown in Table 2.
Table 2
Result above as shown by data has very strong oxidation resistance according to the miracle fruit leaf extract of embodiment 1 to 3.
The constituent analysis of miracle fruit leaf extract
Using ultra high efficiency liquid phase-tandem mass spectrometry (UPLC-MS) determine in above-mentioned miracle fruit leaf extract into packet
Into.Wherein, ultra performance liquid chromatography (UPLC) condition is：
Waters ACQUITY BEH C18 chromatographic columns (50 × 2.1mm, 1.7 μm), 35 DEG C of column temperature；
Waters H-class separator units；
Waters ACQUITY PDADs；
Waters masslynx4.1 mass spectrum management softwares
Mobile phase is acetonitrile (A) and 0.1% aqueous formic acid (B), and using gradient elution, elution program is：Start concentration
For 8%A；0-8min rises to 20%；8-13min rises to 30%A；13-15min rises to 30%A；15-18 rises to 50%A；18-20
Rise to 90%A；20-21 is down to 8%A；21-25min is 8%A.Flow velocity is 0.4mL/min.
Full wavelength scanner, scanning range is 200~600nm.
Mass spectrum (MS-MS) condition is：
Mass spectrum uses electron spray ionisation source [ESI (-)], and full scan scope is 100~1200Da, and capillary voltage is
2.5kV, taper hole voltage is 50V.Ion source temperature is 150 DEG C；Desolvation gas (nitrogen) temperature is 500 DEG C, and flow is
1000L/h；Taper hole gas (nitrogen) flow is 50L/h, and collision gas is high-purity argon gas.
The composition in target product is determined according to standard specimen and mass spectrometric data.
UPLC of the product extracted with 70 volume % methanol after acetonitrile and formic acid gradient separation is shown in Fig. 1, and wavelength is
325nm, be with reference to the main antioxidant material in MASS SPECTRAL DATA ANALYSIS miracle fruit leaf extract：
1st, gallic acid 2, chlorogenic acid 3,5-O- p-coumaroylquinic acids 4,4-O- p-coumaroylquinic acids 5, gallicin
6th, methyl benzoate 7, myricetin -3- galactosides 8, rutin 9, myricetin 10, Hyperoside 11, isoquercitin 12, Kaempferol
3-O- glucosides 13, Quercetin -3- rhamnosides 14, phloridzin 15, quercetin glycoside
It is polyphenol and Flavonoid substances that the main antioxidant material in miracle fruit leaf is understood by result above.
Paralysis Inhibition test of the extract to nematode CL4176 strains
It is prepared by flat board：70% methanolic extract is configured to 0.0002mg/mL, 0.002mg/mL, 0.02mg/ with distilled water
ML, it is 6.27mM (positive control) that caffeine (caffeine) is made into concentration with water, and 540uL is drawn respectively and is coated on nematode life
The surface (6cm culture dishes) of long body culture medium (NGM).After room temperature avoid light place half an hour, after 16 DEG C of income is stood overnight, coating
50uL (1mg/m) Escherichia coli OP50 (65 DEG C of water bath processing 0.5h).The flat board prepared, which places 24h at 16 DEG C, to be used to test.
Experiment process：After CL4176 strains are synchronized on control flat board and Drug plates, 15~16 DEG C of culture 48h
Afterwards, 25 DEG C of inductions are transferred to, 23h starts statistics.
Degree of paralysis comparison in difference is carried out using Log-rank (Mantel-Cox) Test.* represent<0.05, * * represents p<
0.01, * * * represent p<0.001.
The extract of various concentrations is shown in Fig. 2 to the inhibitory action that nematode CL4176 strains are paralysed.
As seen from the figure, concentration is that 0.02mg/mL miracle fruits leaves extract can suppress nematode strain CL4176 paralysis,
But concentration does not suppress the effect of paralysis phenotype when being reduced to 0.002mg/mL and 0.0002mg/mL.Further experiment shows,
Above-mentioned miracle fruit leaf extract can suppress nematode strain CL4176 paralysis in the range of 0.02~0.05mg/mL.
Polyphenols can suppress the poisonous condensate of amyloid proteins, so as to effectively alleviate AD generation, this
A little effects are related all to the antioxygenic property of polyphenols.In addition, to slow down human neuroblastoma thin for Flavonoid substances
The maturation of amyloid precursor protein in born of the same parents, is further able to significantly decrease the ratio of insoluble A β in AD mouse models, so as to also help
In the generation for reducing AD.Phenols and Flavonoid substances content are very high in the miracle fruit leaf extract that the present invention is provided, and have
Good antioxidation activity.The extract shows that miracle fruit leaf extract can be used for for the nematode strain CL4176 suppression paralysed
Prepare effectively treatment AD medicine.
Claims (9)
1. miracle fruit leaf extract is preparing the application in being used to treat the medicine of alzheimer disease, it is characterised in that described
Miracle fruit leaf extract is extracted by following steps：
Miracle fruit leaf is dried, crushed, miracle fruit leaf powder is obtained；
The first alcoholic solution is added into the miracle fruit leaf powder, ultrasonic extraction is carried out, and supernatant is collected by centrifugation, residual residue is again
Extract in the same way at least twice, merging supernatant is alcohol extract；
The alcohol extract obtains miracle fruit Leave extract through vacuum distillation, freeze-drying；
The miracle fruit Leave extract is dissolved in the water, and through macroporous resin treatment, then entered with the second alcoholic solution eluant, eluent
Row elution, collects alcohol eluen；
The alcohol eluen obtains miracle fruit leaf extract dry powder through vacuum distillation and freeze-drying.
2. application according to claim 1, wherein, first alcoholic solution is 50~90% (v/v) methanol aqueous solutions.
3. application according to claim 1, wherein, the ratio of the miracle fruit leaf powder and first alcoholic solution is every gram
Miracle fruit leaf powder uses the alcoholic solutions of 15~45mL first.
4. application according to claim 1, wherein, the ultrasonic extraction carries out 0.5~1h in 40~60 DEG C of water-bath.
5. application according to claim 1, wherein, second alcoholic solution is 10~90% (v/v) ethanol water.
6. application according to claim 1, wherein, first use water before being eluted with the second alcoholic solution eluant, eluent
Elute, and the eluent is given it up.
7. application according to claim 1, wherein, the IC of the miracle fruit leaf extract DPPH radical scavenging activities50
For 83~120 μ g/mL.
8. application according to claim 1, wherein, iron ion reduction/oxidation resistance of the miracle fruit leaf extract
(FRAP) numerical value is 6~8mM/g Trolox.
9. application according to claim 1, wherein, the macroreticular resin is AB-8.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107693556A (en) * | 2017-10-30 | 2018-02-16 | 海南师范大学 | The method that ultrasonic assistant method extracts macroreticular resin separating flavone class compound |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107693556A (en) * | 2017-10-30 | 2018-02-16 | 海南师范大学 | The method that ultrasonic assistant method extracts macroreticular resin separating flavone class compound |
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