CN107875162A - The preparation and application of oleanane-type triterpene saponin - Google Patents
The preparation and application of oleanane-type triterpene saponin Download PDFInfo
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- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
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- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
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Abstract
The present invention relates to one kind from Sapindaceae, isolated oleanane-type triterpene saponin class compound in the shell of shiny-leaved yellowhorn platymiscium shiny-leaved yellowhorn, 16 deoxybarringtogenol C of chemical entitled title 3 O β D glucopyranosyl (1 → 6) (3 ' angeloyl) β D glucopyranosyl 28 O β D glucopyranosyl (1 → 6) [α L rhamnopyranosyl (1 → 2) β D glucopyranosyl].Pharmacological evaluation shows it to (the A β of amyloid beta 25 3525‑35) damage of PC12 cells of induction has good protective effect.The invention further relates to the preparation method of the compound and its preparing the application in treating nerve degenerative diseases medicine.
Description
Technical field
The invention belongs to pharmaceutical technology field, is related to the preparation and application of oleanane-type triterpene saponin, and in particular to one
It is prepared by kind oleanane-type triterpene saponin class compound isolated from Sapindaceae shiny-leaved yellowhorn platymiscium shinyleaf yellowhorn fruit shell
Method and neuroprotection.
Background technology
Shiny-leaved yellowhorn (Xanthoceras sorbifolia) also known as pawpaw, precipice pawpaw, mountain papaw, Wendeng City pavilion, Seng Dengmao roads,
Belong to Sapindaceae (Sapindaceae) shiny-leaved yellowhorn category (Xanthoceras) traditional oil tree, a category is a kind of, main distribution
It is the distinctive oil use in China and medicinal plant in provinces such as China Inner Mongol, Shaanxi, Shanxi, Hebei, Liaoning.The heartwood of shiny-leaved yellowhorn,
The position such as stem branch, fruit or even leaf, flower and benevolence can be used as medicine, and the drying woody part of its stem and branch commonly uses medicine for the Mongols
Material, referred to as anaesthetic wood of shiny-leaved yellowhorn, the entitled hila of Mongolia is gloomy to be stepped on, and sweet, slight bitter is cool in nature, has swelling and pain relieving, clearing damp, holds back dry
The effect of yellow water, it is mainly used in treating rheumatic arthritis, the disease such as heat, skin wind-heat, was once included in version in 1977 in rheumatism《In
Chinese republic pharmacopeia.Its seed is commonly used to treat infantile enuresis, Shenyang Inst. of Applied Ecology, Chinese Academy of Sciences among the people
The preparation for the treatment of infantile enuresis is developed into, it is evident in efficacy.
At present, it is separated from shiny-leaved yellowhorn to have obtained various active chemical composition, including triterpene and triterpene saponin, flavones
Class, steroid, Coumarins, fatty acid, alkaloids and other class compounds.It is considered as discarded before the shell of shiny-leaved yellowhorn
Thing, but recent studies indicate that, shinyleaf yellowhorn fruit shell extract can produce to the learning memory disorder of animal significantly to be changed
Kind effect, total saposins in extract and the monomeric compound Xanthoceraside separated from total saposins can be notable
Ground improve as caused by A beta peptide aggregations AD models mouse learning memory disorder, prompt shiny-leaved yellowhorn in triterpenoid saponins very
There may be the effect of potential anti-senile dementia.And in numerous triterpenoid saponins, due to the difference of its structure, its is anti-ageing
The effect of dementia also has significant difference.
China is the country that AD patient numbers are most in the world, with the aggravation of aging population, the quantity meeting of AD patient
More quickly increase, but at present there has been no the report of relevant treatment senile dementia specific drug, and three in shinyleaf yellowhorn fruit shell
Terpene saponins compound content is very high, and carry out further exploitation as potential medicine resource has practical significance very much.
The content of the invention
It is an object of the invention to provide the neat honest fruit alkane type triterpenoid saponins compound of formula (I) to prepare neuroprotection work
Application in medicine.
Described neat honest fruit alkane type triterpenoid saponins compound, its general structure are as follows：
3-O-β-D-glucopyranosyl(1→6)-(3′-angeloyl)-β-D-glucopyranosyl-28-O-β-
D-glucopyranosyl(1→6)[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-16-
deoxybarringtogenol C
Wherein：
R1=3-O- (3-O-angeloyl-6-O- β-D-glucopyranosyl)-β-D-glucopyranosyl R2=
28-O-(2-α-L-rhamnopyranosyl-6-O-β-D-glucopyranosyl)-β-D-glucop yranosyl
Concrete structure formula is as follows：
Present invention also offers the compound preparation method, its specific step is as follows：
(1) the drying shell of shiny-leaved yellowhorn is taken, alcohol reflux extraction, filtering, merging filtrate, alcohol extract is obtained, alcohol extract is subtracted
Pressure is recycled to no alcohol taste, obtains concentrate；
(2) concentrate obtained by is loaded in D101 macroporous resin columns, respectively with pure water, 20-30% alcohol-waters, 60-
70% alcohol-water and 85-95% alcohol-waters are that mobile phase carries out gradient elution, collect the eluent of 60-70% alcohol-waters, subtract
Recycling design is pressed, obtains the crude extract of triterpenoid saponin；
(3) by the crude extract of triterpenoid saponin, it is splined in silicagel column.Use dichloromethane/chloroform with methanol for stream
Dynamic mutually to carry out gradient elution, the target flow point of elution uses dichloromethane/chloroform to carry out ladder with methanol for mobile phase again
Degree elution, obtain flow point D (dichloromethane/chloroform and methanol=100:30~100:50).By sample introduction after flow point D processing extremely
Liquid phase is prepared through half, is detected under 205nm Detection wavelength, with acetonitrile-water (27:73~29:71), afforded for mobile phase
Compound I.
In step (1), described ethanol is 70-80% ethanol solution.
The volume of the ethanol solution is 6-8 times that shiny-leaved yellowhorn dries shell, refluxing extraction 2-3 times, each 1-2h, is merged
Extract solution.
Using silica gel column chromatography twice in step (3).Use methylene chloride-methanol 100 for the first time:0~0:100 carry out gradient
11 flow points are afforded, flow point 8 carries out second and eluted, using methylene chloride-methanol 100:5~0:100 carry out gradient elution.
Triterpene saponin componds prepared by the present invention have significant neuroprotection.
Triterpene saponin componds prepared by the present invention can be used in preparing the medicine for the treatment of nerve degenerative disease.
Specifically, chemical compounds I of the present invention is preparing treatment neuroinflamation, alzheimer disease, Parkinson, henry
The court of a feudal ruler, mostly occur hardening, vascular dementia, cerebral ischemia, epilepsy, amyotrophic lateral sclerosis, different type spinocerebellum mutual aid
Application in imbalance, Pick sick medicine.
It is highly preferred that chemical compounds I of the present invention is preparing treatment neuroinflamation, alzheimer disease, Parkinson, blood
Pipe is dull-witted, the application in the medicine of cerebral ischemia.
Chemical compounds I of the present invention can be prepared into clinically acceptable system with pharmaceutically acceptable excipient
Agent：Including oral formulations and injection, described oral formulations include tablet (ordinary tablet, lozenge, sublingual tablet, mouth paster, nozzle
Chew piece, dispersible tablet, fuse, effervescent tablet, sustained release tablets, controlled release tablet, enteric coatel tablets, oral dosage form etc.)；Pill (dripping pill, sugar-pill,
Piller)；Oral liquid (syrup, supensoid agent, solution, emulsion, mixture, distillate medicinal water or medicinal tea)；Granule (suspension
Grain, effervescence granular, enteric coated particles, slow-releasing granules, controlled release granule etc.) or powder etc..
Preferably oral liquid, such as chemical compounds I oral emulsion or chemical compounds I suspension oral liquid.
The injection includes powder pin and solution.
Preferably inject the parenteral solution or chemical compounds I emulsion injection that pharmaceutical solutions is chemical compounds I.
The excipient and auxiliary material of oral formulations include but are not limited to filler or diluent, lubricant or glidant or
Anti stickness agent, dispersant, wetting agent, adhesive, conditioning agent, solubilizer, antioxidant, bacteriostatic agent, emulsifying agent etc..Adhesive, example
Such as syrup, Arabic gum, gelatin, sorbierite, tragacanth, cellulose and its derivates, gelatine size, syrup, starch slurry or poly- second
Alkene pyrrolidone, preferable cellulose derivative are microcrystalline cellulose, sodium carboxymethylcellulose, ethyl cellulose, hydroxypropyl
Cellulose；Filler, such as lactose, Icing Sugar, dextrin, starch and its derivative, cellulose and its derivates, inorganic calcium salt, mountain
Pears alcohol or glycine, preferably inorganic calcium salt are calcium sulfate, calcium phosphate, calcium monohydrogen phosphate, precipitated calcium carbonate；Lubricant, such as micro mist
Silica gel, magnesium stearate, talcum powder, aluminium hydroxide, boric acid, hydrogenated vegetable oil, polyethylene glycol；Disintegrant, such as starch and its spread out
Biology, polyvinylpyrrolidone or microcrystalline cellulose, preferable starch derivatives be sodium carboxymethyl starch, Explotab,
Pregelatinized starch, modified starch, hydroxypropul starch, cornstarch；Wetting agent, such as lauryl sodium sulfate, water or alcohol etc..
The usual excipients or auxiliary material of the injection preparation include but are not limited to：Antioxidant, such as sodium thiosulfate,
Sodium sulfite, sodium hydrogensulfite, dibutyl benzoic acid or sodium pyrosulfate etc.；Bacteriostatic agent, for example, 0.5% phenol, 0.3% cresols,
0.5% anesin；PH adjusting agent, such as potassium hydroxide (sodium), sodium citrate and buffer sodium dihydrogen phosphate and phosphoric acid hydrogen
Disodium；Emulsifying agent, such as polysorbate -80, do not have that sour sorb is smooth, pluronic gram F-68, lecithin, Fabaceous Lecithin；Solubilizer,
Such as Tween-80, glycerine etc..
Active component and pharmaceutically acceptable slow controlled release carrier can also be mixed by its preparation requirement in addition, by
According to the preparation method of sustained-release preparation well known in the art, such as add retarding agent coating or will be made again after active principle microcapsules
Micropill, such as sustained release pellet or controlled release micro pill；Described slow controlled release carrier includes but are not limited to oil dopant, hydrophilic colloid
Or coating retarding agent etc., described oil dopant are glycerin monostearate, rilanit special, Dormant oils, polysiloxanes, two
Methylsiloxane；Described hydrophilic colloid is the fibers such as sodium carboxymethylcellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose
Plain derivative, or PVP, Arabic gum, tragcanth or carbopol etc.；Described coating retarding agent is ethyl cellulose, hydroxypropyl
Methylcellulose, polyvinylpyrrolidone, cellulose acetate-phthalate, acrylic resin etc..
A kind of oleanane-type triterpene saponin class compound provided by the invention, shows, chemical combination of the present invention through effect experiment
Thing can be to amyloid-beta 25-35 (A β25-35) damage of PC12 cells of induction has good protective effect.It can make
For the potential medicine of prevention of neurodegenerative diseases, a kind of new selection is provided for clinic.
Obviously, according to the above of the present invention, according to the ordinary technical knowledge and customary means of this area, do not departing from
Under the premise of the above-mentioned basic fundamental thought of the present invention, the modification, replacement or change of other diversified forms can also be made.
Below by way of the embodiment of example forms, the above of the present invention is remake further specifically
It is bright.But the scope that this should not be interpreted as to the above-mentioned theme of the present invention is only limitted to following example.It is all to be based on the above of the present invention
The technology realized belongs to the scope of the present invention.
Brief description of the drawings
Fig. 1 is the neat honest fruit alkane type triterpenoid saponins compound pre-administration shown in formula (I) to A β 25-35 induced damages
The influence of the survival rate of PC12 cells.
Embodiment
Instrument and reagent
HPLC-UV systems (Japanese Shimadzu Corporation), NMR (Bruker ARX-300, AV600, German Bruker
Company), RE-52 Rotary Evaporators (Shanghai Yarong Biochemical Instrument Plant), column chromatography silica gel (100-200 mesh, 200-300 mesh) (green grass or young crops
Island marine chemical industry factory), thin-layer chromatography silica G F 254 (Haiyang Chemical Plant, Qingdao), D101Macroreticular resin (Cangzhou treasured grace sorbing material
Science and Technology Ltd.).
Shinyleaf yellowhorn fruit shell picks up from Inner Mongolia Autonomous Region Chifeng City.
Extraction separation：
The shell (7.5kg) that shiny-leaved yellowhorn is dried crushes, and (measures) refluxing extraction for 8 times every time 3 times with 70% ethanol, each 2h.Merge
Extract solution, solvent is recovered under reduced pressure to without alcohol taste, obtains concentrate.The concentrate is splined on to the D pre-processed101Macroporous absorption tree
It is respectively that mobile phase carries out gradient elution with water, 30% alcohol-water, 70% alcohol-water, 95% alcohol-water in fat, finally
To 4 flow points, the eluent eluted with 70% alcohol-water is collected, after solvent concentration is recovered under reduced pressure, obtains shiny-leaved yellowhorn
The crude extract of triterpenoid saponin about 100g.The crude extract is splined in silicagel column.With methylene chloride-methanol 100:0~0:100
Gradient elution is carried out, obtains 11 flow points, flow point 8 again passes by silica gel column chromatography, methylene chloride-methanol 100:5~0:100 carry out ladder
Degree elution, obtains 8 flow points, and flow point 5 prepares liquid phase through half.Sample introduction after flow point D processing is prepared into liquid phase to through half, in 205nm inspection
Survey under wavelength and detect, with acetonitrile-water (28:72) compound (30.8mg, purity 95.5%) has been afforded for mobile phase.
The compound is white needles (methanol), is developed the color with 10% ethanol solution of sulfuric acid and shows purple, high resolution mass spectrum provides
Molecular ion peak (being detected under positive ion mode)：m/z 1373.6705[M+Na]+(calcd.for C65H106O29Na,
1373.6712), with reference to its NMR data, thus it is speculated that its molecular formula is C65H106O29.Its1The high field region of H-NMR spectrums provides 7 features
Angular methyl signal：δ 0.93 (3H, s), δ 0.95 (3H, s), δ 1.07 (3H, s), δ 1.20 (3H, s), δ 1.22 (6H, s), δ
It may be Triterpenoids sapogenins that 1.23 (3H, s), δ 1.25 (3H, s), which prompt it,；One group of angeloyl groups signal：δ1.88
(3H, s), δ 1.93 (3H, dd, J=7.2,1.2Hz), δ 5.81 (1H, dq, J=7.2,1.3Hz)；In addition H-3 ' is to low field position
Move, illustrate that angeloyl groups are connected to H-3 ' positions.Five sugared anomeric proton signals：δ 4.85 (1H, d, J=7.2Hz, H-1 '), δ
5.10 (1H d, J=7.8Hz, H-1 "), δ 4.72 (1H, d, J=7.2Hz, H-1 " '), δ 5.04 (1H, d, J=8.4Hz, H-
1 " "), δ 6.53 (1H, s, H-1 " " '), prompts four grape bglii fragments and a sandlwood bglii fragment in the compound be present, and by
Its coupling constant understands that the glycosidic bond configuration of glucose is β types, and this is assumed at it13It is proven in C-NMR spectrums.The chemical combination
Thing13C-NMR composes the end group carbon signal for also giving five bglii fragments：δ 105.6 (C-1 '), δ 104.5 (C-1 "), δ 102.5
(C-1 " '), δ 104.6 (C-1 " " '), δ 99.8 (C-1 " ").In addition13C-NMR spectrum give a carbonyl signals δ 167.0 and
The carbon signal δ 128.7 and δ 135.8 of a pair of alkene, also demonstrate the presence of an angeloyl groups.By comparing itself and document report
Road1H-NMR and13C-NMR modal datas, the two is basically identical, and therefore, it is 3-O- β-D- to identify the compound
glucopyranosyl(1→6)-(3′-angeloyl)-β-D-glucopyranosyl-28-O-β-D-glucopyranosyl
(1→6)[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-16-deoxybarringtogenol C。
The aglycon part of the compound is neat honest fruit alkane type triterpenoid, and its general structure is as follows：
R1=3-O- (3-O-angeloyl-6-O- β-D-glucopyranosyl)-β-D-glucopyranosyl R2=
28-O-(2-α-L-rhamnopyranosyl-6-O-β-D-glucopyranosyl)-β-D-glucop yranosyl
Concrete structure formula is as follows：
Chemical compounds I has following spectroscopic properties：
Beneficial effects of the present invention are proved below by way of experimental example.
The neuroprotective activity of the anti-alzheimer disease of the compounds of this invention of example 1
Cell culture：PC12 cell lines, which are used, contains 10% hyclone, 100U/ml penicillin, the H- of 100U/ml streptomysins
DMEM culture medium inoculateds are in blake bottle, CO2The condition of culture of cell culture incubator is 37 DEG C, 5%CO2 concentration, saturated humidity, is treated
Cell length starts to pass on or is inoculated with to 80% or so.Inverted microscope observes cell growth condition, takes the logarithm growth period during experiment
Cell is tested.
PC12 cells are randomly divided into control group, model group, basic, normal, high 3 dosage experiments groups and positive controls.
After serum free medium inoculation 24h, start administration 1. Normal group：Normal PC12 cells；2. model group：Normal PC12 is thin
Born of the same parents；3. chemical compounds I low dose group：0.01mg/ml chemical compounds Is；4. chemical compounds I middle dose group：5. 0.05mg/ml chemical compounds Is are changed
The high dose group of compound I：0.1mg/ml chemical compounds Is.6. positive controls：0.242×10-3Mg/ml huperzines A.Act on 24h
Afterwards, in addition to Normal group, remaining each group adds 20 μM of A β25-35, after cultivating 24h, dimethyl sulfoxide (DMSO) and MTT are added, uses enzyme
Mark instrument determines optical density (OD) value at 490nm.
Data processing：Cell viability percentage expression, cellular control unit vigor is regarded as 100%, is as a result calculated：Cell is lived
Power=(experimental group OD values-blank group OD values)/(Normal group OD values-blank group OD values) × 100%.Using SPSS17.0 pairs
Statistical result is analyzed, and data use one-way analysis of variance, and P ＜ 0.05 represent there is significant difference, and P ＜ 0.01 are represented
With pole significant difference.Experimental result is shown in Fig. 1.
Experimental result：Compared with Normal group, model group cell viability substantially reduces (P ＜ 0.01)；If before modeling
The compounds of this invention is given, cell mortality significantly reduces, wherein each dosage group is relatively respectively provided with statistics meaning with model group
Adopted (P ＜ 0.05).
Test result indicates that, A β are secreted by cell produces very strong neurotoxicity after cellular matrix precipitation aggregation above,
Caused inflammatory reaction is the main reason for causing alzheimer disease patient neurons to lose after deposition.Aβ25-35It is that its is main
Toxicity center, nerve cell can be damaged, cause a large amount of apoptosis of PC12 cells, cell viability decline,；If given before modeling
The compounds of this invention, cell mortality significantly reduce, and show that the compound has the function that significantly to prevent alzheimer disease.
In summary, chemical compounds I provided by the invention can reduce A β25-35Caused by cellular damage, there is significant god
Through protective effect, and there is no obvious neurotoxicity under higher dosage, the god such as preventing and treating alzheimer disease can be used as
Potential medicine through degenerative disease, a kind of new medication selection is provided for clinic.
Claims (10)
1. neat honest application of the fruit alkane type triterpenoid saponins compound in the medicine of neuroprotection is prepared shown in formula (I),
Characterized in that, the general structure of described neat honest fruit alkane type triterpenoid saponins compound is as follows：
3-O-β-D-glucopyranosyl(1→6)-(3′-angeloyl)-β-D-glucopyranosyl-28-O-β-D-
glucopyranosyl(1→6)[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-16-
deoxybarringtogenol C
Wherein：
R1=3-O- (3-O-angeloyl-6-O- β-D-glucopyranosyl)-β-D-glucopyranosyl
R2=28-O- (2- α-L-rhamnopyranosyl-6-O- β-D-glucopyranosyl)-β-D-
glucopyranosyl。
2. neat honest fruit alkane type triterpenoid saponins compound the answering in treatment nerve degenerative diseases medicine is prepared shown in formula (I)
With, it is characterised in that the general structure of described neat honest fruit alkane type triterpenoid saponins compound is as follows：
3-O-β-D-glucopyranosyl(1→6)-(3′-angeloyl)-β-D-glucopyranosyl-28-O-β-D-
glucopyranosyl(1→6)[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-16-
deoxybarringtogenol C
Wherein：
R1=3-O- (3-O-angeloyl-6-O- β-D-glucopyranosyl)-β-D-glucopyranosyl
R2=28-O- (2- α-L-rhamnopyranosyl-6-O- β-D-glucopyranosyl)-β-D-
glucopyranosyl。
3. application as claimed in claim 2, it is characterised in that described nerve degenerative diseases refer to neuroinflamation, A Erzi
The silent disease in sea, Parkinson, Huntington disease, mostly occur hardening, vascular dementia, cerebral ischemia, epilepsy, amyotrophic lateral sclerosis, no
Same type spinocerebellar ataxia or Pick diseases.
4. the application as described in claim 1-3 any one, it is characterised in that
(1) shell for drying shiny-leaved yellowhorn crushes is extracted with alcohol reflux, is filtered, is merged extract solution, solvent is recovered under reduced pressure to nothing
Alcohol taste, obtain concentrate；
(2) concentrate is splined on to the D pre-processed101In macroporous absorbent resin, respectively with water, 20-30% ethanol-
Water, 60-70% alcohol-water, 85-95% alcohol-waters are that mobile phase carries out gradient elution, finally obtain 4 flow points, collect and use
The eluent that 60-70% alcohol-water elutes, after solvent concentration is recovered under reduced pressure, obtain shiny-leaved yellowhorn triterpenoid saponin
Crude extract；
(3) crude extract is splined in silicagel column, carrying out gradient as mobile phase with methanol using dichloromethane/chloroform washes
It is de-, obtain dichloromethane/chloroform and methanol=100:30~100:Flow point D under 50 gradients, by sample introduction after flow point D processing
Liquid phase is prepared to half, is detected under 205nm Detection wavelength, with acetonitrile-water (27:73~29:71) afforded for mobile phase
Chemical compounds I.
5. application as claimed in claim 4, it is characterised in that the ethanol that the ethanol described in step (1) is 70-80% is molten
Liquid；The volume of the ethanol solution is 6-8 times that shiny-leaved yellowhorn dries shell, refluxing extraction 2-3 times, each 1-2h, merges extraction
Liquid.
6. application as claimed in claim 4, it is characterised in that using silica gel column chromatography twice in step (3), use for the first time
Methylene chloride-methanol 100:0~0:100 carry out gradient elution；Methylene chloride-methanol 100:50 parts carry out second and eluted,
Use methylene chloride-methanol 100 for the second time:5~0:100 carry out gradient elution.
7. the application as described in claim 1-3 any one, it is characterised in that described compound I can be with pharmaceutically may be used
The auxiliary material of receiving is prepared into clinically acceptable preparation.
8. application as claimed in claim 7, it is characterised in that described preparation includes oral formulations and injection.
9. application as claimed in claim 8, it is characterised in that described oral agents are tablet, pill, liquid preparation, powder
Or granule.
10. application as claimed in claim 8, it is characterised in that described injection includes injection powder pin and injection
Use solution.
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| CN113072608A (en) * | 2020-01-03 | 2021-07-06 | 沈阳药科大学 | Triterpenoid saponin compound and application thereof |
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