CN106892957B - A kind of oleanane-type triterpene saponin class compound and its preparation method and application - Google Patents
A kind of oleanane-type triterpene saponin class compound and its preparation method and application Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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Abstract
The present invention relates to a kind of oleanane-type triterpene saponin class compounds, shown in the molecular structure of the compound such as following formula (I).Compound of the present invention is extracted by RADIX ILICIS PUBESCENTIS alcohol reflux and column chromatography separating purification obtains.Compound of the present invention has anti-inflammatory activity, can be used for preparing the drug for preventing and treating inflammatory vascular diseases.
Description
Technical field
The present invention relates to steroids, and in particular to pentacyclic triterpenoid and the compound are scorching in preparation treatment
Application in disease property vascular diseases drug.
Background technique
Ilex pubescens is Aquifoliaceae (Aquifoliaceae) Holly Ilex pubescens Hook.et Arn., not
The black tail fourth of name, frost in June, spire Chinese ilex, hair drape over one's shoulders tree, extreme misery medicine, fire and iron wood etc., and main product is in Guangdong, Jiangxi, Fujian, Guangxi etc.
Ground is south China conventional Chinese medicine.Its medicinal part is root, has the effect of promoting blood circulation and removing obstruction in channels, swelling and pain relieving, clearing heat and detoxicating, faces
Treatment coronary heart diseases and angina pectoris, Buerger's disease etc. are widely used on bed.
There is document report to cross anti-inflammatory effect (Wang JR, Zhou H, Jiang ZH, the Wong YF, Liu at ilex pubescens position
L.In vivo anti-inflammatory and analgesic activities of a purified saponon
fraction derived from the root of Ilex pubescens.Biol.Pharm.Bull.2008,21,643-
650.), at the same have document report therefrom isolated triterpene saponin componds have it is antitumor (Zhou Y, Chai XY,
Zeng K,Zhang JY,Li N,Jiang Y,Tu PF,llexpublesnins C-M,eleven new triterpene
Saponins from the roots of Ilex pubescens.Planta.Med.2013,79,70-77.), antithrombotic
(anti thrombotic action of the chivalrous Ilexsaponin B3 of Xiong Tianqin, Chen Yuanyuan, Li Hong is studied, Chinese herbal medicine .2012,43,1758-1788)
With inhibition xanthine oxidase (Zhou Z L, Feng Z C, Yin W Q, Zhang H L.A new triterpene
saponin from the leaves of Ilex pubescens and its XOD inhibitory
activity.Chem.Nat.Compd.2013,49(4):682-684.) act on.
Oleanane-type triterpene saponin class compound is distributed more widely in plant kingdom, according to the literature from 1996 to 2012 year
Period is more than altogether thousands of (Dinda B, Debnath S, Mohanta from nature discovery oleanane type triterpene class compound
BC,Harigaya Y.Naturally Occurring Triterpenoid Saponins.Chemistry
Biodiversity.2010,2327-2580.Hill RA,Connolly
JD.Triterpenoids.Nat.Prod.Rep.2015,32:273-327).Report about such compound anti-inflammatory activity is simultaneously
It is not especially more, foreign scholar Son (Kwak WJ, Son KH.Loniceroside C, an Antiinflammatory
Saponin from Lonicera japonica.Chem.Pharm.Bull.2003,51:333-335.) from honeysuckle
The isolated two oleanane type triterpenes class compound of the aerial part of (Lonicera japonica) is respectively
Loniceroside A and Loniceroside C, and with its anti-inflammatory activity of croton oil inducing mouse dropsy of ear experimental evaluation, knot
Fruit is shown under the dosage of 100mg/kg, and inhibiting rate is respectively 30.2% and 31.0%.There are scholar (Wang HL, Yu
BY.Two New Triterpenoid Saponins Isolated from Polygala
japonica.Chem.Pharm.Bull.2006,54:1739-1742.) from polygala Japanese polygala (Polygala
Japonica 6 oleanane type type triterpene compounds are found in), in the acute pedal swelling model of carrageenan inducing mouse
In, saponin(e 3,4,5 shows more significant anti-inflammatory activity under the dosage of 0.1mol/kg.There are scholar (Wei F, Lin
RC.Antiinflammatory Triterpenoid Saponins from the Seeds of Aesculus
chinensis.Chem.Pharm.Bull.2004,52:1246-1248.) from the kind of horse chestnut (Aesculus chinensis)
In son find four oleanane type triterpene class compounds, they be respectively escin 1a, escin 1b, isoescin 1a and
Isoescin 1b, in dimethylbenzene inducing mouse dropsy of ear model, inhibiting rate is 67.3%- under the dosage of 30mg/kg
79.3%.There is scholar (Shi SP, Tu PF.Triterpene Saponins from Clematis
mandshurica.J.Nat.Prod.2006,69:Two oleananes 1591-1595) are found from the rhizome of polygonum flaccidum clematis
Type triterpene compound is clematomandshurica saponins A and B respectively, and in LPS inducing mouse abdominal cavity, macrophage is thin
In born of the same parents' model, they inhibit the IC of COX-250Value is respectively 2.66 and 2.58 μM.There are scholar (Wu C, Li
YL.Triterpenoid Saponins from the stem Barks of Schefflera heptaphylla.Planta
Med.2013,79:Two oleanane type triterpene class compounds 1348-1355) are found from the bark of Ivy Tree Bark
Heptoleoside B and C under 40 μM of concentration, distinguish the inhibiting rate of NO in LPS induction RAW264.7 cell model
For 22.5% and 45.2%, but the anti-inflammatory activity of two oleanane-type triterpene saponin compounds of gained is still undesirable.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of oleanane-type triterpene saponin class compound, compound treatment
The significant effect of inflammatory vascular diseases.
Technical solution the invention solves the above problem is：
A kind of oleanane-type triterpene saponin class compound, molecular structure is as shown in formula I：
The molecular formula C of oleanane-type triterpene saponin class compound of the present invention41H64O14, HR-ESI-MS m/z [M
+Na]+:803.4190, chemical name is -3 β of 3-O- β-D- glucopyranosyl, 19 alpha-dihydroxy oleanane -24- aldehyde radicals -
12- alkene -28- acid-O- β-D- glucopyranoside.
Oleanane-type triterpene saponin class compound of the present invention can pass through chemically synthesized method.This field
Technical staff can determine synthesis step and process conditions by the knowledge of this field.Oleanane type triterpene of the present invention
Saponins compound can also be isolated from ilex pubescens (Ilex pubescens Hook et Arn.), specific separation side
Method is made of lower step：
(1) RADIX ILICIS PUBESCENTIS is taken, successively extracts 2h with the alcohol reflux that 12,10 and 8 times of concentration are 70%, merges ethyl alcohol and extracts
Liquid recycles ethyl alcohol and is concentrated under reduced pressure into no alcohol taste, obtains total medicinal extract；
(2) total medicinal extract is dissolved in water, crosses D-101 type macroporous resin column, successively the ethyl alcohol with concentration for 30%, concentration
The ethanol elution that ethyl alcohol and concentration for 60% are 95%；Collect the silicon that the ethanol eluate that concentration is 60% crosses 200~300 mesh
Rubber column gel column is eluted by solvent of chloroform-methanol by the gradient that Lv Fang ︰ methanol is 100 ︰, 1~0 ︰ 1；Collection Lv Fang ︰ methanol is 9 ︰
1 eluent crosses Sephadex LH-20 column, using methanol as eluent, crosses ODS column after collecting eluent concentration, collects first
Alcohol：Water is 52：48 eluent obtains white powder crystallization after concentration.
The concentration of ethyl alcohol described in above-mentioned separation method is volumetric concentration.
Ilex pubescens described in above-mentioned separation method is Aquifoliaceae (Aquifoliaceae) Ilex (Ilex) vegetable hair winter
Green dry root.
Oleanane-type triterpene saponin class compound of the present invention, have anti-inflammatory effect, can be used for preparing prevention and
Treat the drug for treating inflammatory vascular diseases.The drug is the oleanane-type triterpene saponin class chemical combination as shown in (I) formula
Object and the pharmaceutically common dosage form of acceptable auxiliary material composition, e.g., injection, tablet or capsule etc..In the preparation
(I) weight percentage of formula compound represented is 10%~50%.
Prove that technology possessed by oleanane-type triterpene saponin class compound shown in (I) formula is imitated below by experiment
Fruit.The RAW264.7 cell model induced using lipopolysaccharides (LPS) studies nitric oxide synthetase in compound on intracellular
(iNOS) and the influence of cyclooxygenase-2 (COX-2) expressing quantity the anti-inflammatory effect of compound of the present invention, is investigated, it is specific real
Proved recipe method is as described below.
Material and method
1, sample 1 is from preparation method shown in specific embodiment 1.Reference substance clematomandshurica
Saponins B is document (Shi SP, Tu PF.Triterpene Saponins from Clematis
mandshurica.J.Nat.Prod.2006,69:1591-1595) reported compound, concrete structure formula such as following formula (II) institute
Show.Positive control drug DEX is dexamethasone.
clematomandshurica saponins B
2, source of mouse macrophage RAW264.7 is purchased from American Type Culture Collection, is stored in containing 10%FBS, 100units/ml
In Benzylpenicillin, 100mg/ml streptomysin and 2mM L- l-glutamine culture solution, in saturated humidity, 37 DEG C, 5%CO2Condition
Lower culture.
3, compound is dissolved in DMSO, and mother liquid concentration is made into 30mM, and working concentration is 30 μM.
4, RAW264.7 cell is with 8 × 104A/hole is inoculated in 24 orifice plates and cultivates for 24 hours, and cell passes through test sample and sun
Property comparison medicine (0.5 μM) pretreatment 1h of dexamethasone, then 18h is stimulated with the LPS of 100ng/ml, if blank combines normal group.
5, Western Blot method：It is with the RIPA lysate containing protease inhibitors that cell is total after LPS stimulation
Protein extraction comes out, and measures concentration, transferring film after gel electrophoresis by Bio-Rad protein quantitative methods, 5% skim milk carries out
Closing, is then incubated overnight under the conditions of 4 DEG C with iNOS, COX-2 primary antibody and mouse specific antibody, and room temperature secondary antibody is incubated for, albumen
Expression contents are analyzed with Odyssey v3.0 software.
6, it statisticallys analyze：Above-mentioned testing result indicates that sample combination blank control group data carry out statistical data with X ± S
Credit analysis, P < 0.05 indicate there is significant difference.
1 iNOS and COX-2 protein expression inhibiting rate of table
Above the experimental results showed that compound 1 can conspicuousness inhibit LPS induction RAW264.7 cell in iNOS and
The expression of COX-2 albumen.Show that the compound all has preferable section anti-inflammatory effect.Simultaneously with reported compound
Clematomandshurica saponins B is compared, although two compounds are not much different to COX-2 inhibiting rate, is changed
It closes object 1 and clematomandshurica saponins B is obviously greater than to the inhibiting rate of iNOS, that is to say, that compound 1 has
There is the characteristics of more targets.
Detailed description of the invention
Fig. 1 compound of the present invention1H-NMR schemes (400MHz).
Fig. 2 compound of the present invention13C-NMR schemes (100MHz).
The DEPT of Fig. 3 compound of the present invention schemes.
The COSY NMR of Fig. 4 compound of the present invention schemes.
The HSQC NMR of Fig. 5 compound of the present invention schemes.
The HMBC NMR of Fig. 6 compound of the present invention schemes.
The NOESY NMR of Fig. 7 compound of the present invention schemes.
Specific embodiment
Following experiments pick up from Conghua City of Guangdong Province with ilex pubescens (Ilex pubescens Hook et Arn.) root.
Example 1：
One, the preparation of compound
(1) RADIX ILICIS PUBESCENTIS is taken, successively extracts 2h with the alcohol reflux that 12,10 and 8 times of concentration is 70%, merges ethyl alcohol and mentions
Liquid is taken, ethyl alcohol is recycled after filtering and is concentrated under reduced pressure into no alcohol taste, obtains total medicinal extract 2.2kg；
(2) total medicinal extract is dissolved in water, crosses D-101 type macroporous resin column, successively the ethyl alcohol with concentration for 30%, concentration
The ethanol elution that ethyl alcohol and concentration for 60% are 95%；It collects the ethanol eluate that concentration is 60% and solvent is recovered under reduced pressure, obtain
Thick medicinal extract 566g, the thick medicinal extract cross the silicagel column of 200~300 mesh, by solvent of chloroform-methanol by chlorine imitate ︰ methanol be 100 ︰ 1~
The gradient of 0 ︰ 1 is eluted；Sephadex LH-20 column is crossed after collecting the eluent concentration that Lv Fang ︰ methanol is 9 ︰ 1, is with methanol
Eluent crosses ODS column after collecting eluent concentration, collects methanol：Water is 52：48 eluent obtains white after concentration
Powdery crystal 16mg.
Two, the identification of compound
Obtained white powder crystallization Liebermann-Burchard reaction is positive, and finally shows aubergine, says
Bright its is triterpene compound.
Hydroxyl group absorption (3429cm is shown referring to Fig. 1~5, IR-1), carbonyl absorption (1705cm-1), double bond absorbs
(1632cm-1).High resolution mass spectrum provides molecular formula C41H64O14, [M+Na]+:803.4190 calculating the molecule according to molecular formula
Degree of unsaturation be 9.The compound passes through sour water solution, and TLC and HPLC analysis and the derivative with saccharide are used after derivatization
Control, it was demonstrated that its sugar unit is D- xylose and D-Glucose.Referring to table 1,1341 carbon signals are shown altogether in C-NMR spectrum, wherein 11
A to be attributed to sugar, being left 30 carbon signal prompts may be triterpene aglycon.Referring to table 1,16 angular methyls are shown in H-NMR spectrum
Signal [δH0.79,0.96,1.08,1.16,1.60,1.63].One group of three substitution double bond (δH 5.51,δC123.6,C-12；δC
144.2, C-13), an aldehyde radical (δH 10.38,δC206.4, CHO-24), an ester carbonyl group (δC177.6, COOR-28), one
Anomeric proton signal (the δ of a xyloseH 4.84,δC108.2, CH-Xyl-1) and the anomeric proton signal (δ of a glucoseH
6.36,δC96.2, CH-Glc-1), coupling constant is 7.2 and 8.0 prompt D- xyloses and D-Glucose is beta configuration.With
The upper information alert compound may be while have the oleanane-type triterpene saponin of carboxyl, aldehyde radical and hydroxyl.With knownization
It closes object ilexpublesnin L and compares carbon modal data, the two chemical shift is much like, and difference is 3 different sugar units.
Referring to Fig. 6, HMBC spectrum display alkene hydrogen δH5.51 (1H, br s, H-12) and δC 24.9(C-11)、δC 42.4(C-
And δ 14)C45.0 (C-18) have long-range correlation, and double bond is prompted to be between C-12 and C-13.HMBC spectrum display connects oxygen hydrogen δH
3.59 (1H, m, H-19) and δC46.8 (C-17) and δC29.1 (C-29) have long-range correlation, and hydroxyl is prompted to be in C-19.
HMBC spectrum display δH4.84 (d, J=7.2Hz, CH-xyl-1) and δC87.0 (C-3) have long-range related determining xylose to be connected to C-
On 3.
Referring to Fig. 7, ROESY spectrum shows that its relevant peaks has H-C (3)/H-C (5), H-C (5)/H-C (9), H-C (9)/H-C
(27), H-C (20)/H-C (27) prompts 19 oxygen to replace, 23-Me and 27-Me are in α, relevant peaks H-C (24)/H-C (25),
H-C (25)/H-C (26), H-C (19)/H-C (30) prompt 3 oxygen substitutions, 24-CHO, 25-Me, 26-Me and 30-Me to be in β
Position.The structure for sum up determining noval chemical compound is -3 β of 3-O- β-D- glucopyranosyl, 19 alpha-dihydroxy oleanane -24- aldehyde
Base -12- alkene -28- acid-O- β-D- glucopyranoside.
2 chemical compounds I of table1H NMR and13C NMR data (Pyridine-d5, J=Hz)
Example 2：(injection)
The compound 1000mg obtained using 1 the method for above-described embodiment is taken, adds the water for injection of 1000ml, uses carbonic acid
Sodium tune pH value is stirred to dissolve, degerming filtration, encapsulating is made every through 100 DEG C of 15 minutes flowing steam sterilizations to 7~7.5
The injection of 2mg/2ml is used for injection.
Example 3：(capsule)
Take the compound 5000mg and 4000mg microcrystalline cellulose, 500mg carboxylic obtained using 1 the method for above-described embodiment
The auxiliary materials such as methyl starch sodium, 400mg lauryl sodium sulfate are sufficiently mixed, using roll-in method carry out dry granulation, then in right amount
Magnesium stearate mixes, and is packed into 3# Capsules, and the capsule that specification is 100mg/ is made and supplies to be administered orally.
Example 4：(tablet)
Take the compound 5000mg obtained using 1 the method for above-described embodiment and 4000mg starch, 200mg cross-linked pvp,
300mg sodium carboxymethyl starch is uniformly mixed, and uses 75% ethanol solution of 5%PVP as adhesive, softwood processed, with 18 mesh Shai Zhi
Appropriate talcum powder is added after 20 mesh whole grains in grain, 1h after 60 DEG C of drying, mixes, tabletting, and the tablet confession that specification is 100mg/ piece is made
It is administered orally.
Claims (5)
1. a kind of oleanane-type triterpene saponin class compound, shown in molecular structure such as following formula (I)：
2. the preparation method of oleanane-type triterpene saponin class compound described in claim 1, this method is by following steps group
At：
(1) RADIX ILICIS PUBESCENTIS is taken, successively 2h is extracted with the alcohol reflux that 12,10 and 8 times of concentration are 70%, merges ethanol extract,
Recycling ethyl alcohol is simultaneously concentrated under reduced pressure into no alcohol taste, obtains total medicinal extract；
(2) total medicinal extract is dissolved in water, crosses D-101 type macroporous resin column, the ethyl alcohol for being successively 30% with concentration, concentration are
The ethanol elution that 60% ethyl alcohol and concentration is 95%；It collects the ethanol eluate that concentration is 60% and solvent is recovered under reduced pressure, obtain thick
Medicinal extract, the thick medicinal extract cross the silicagel column of 200~300 mesh, and imitating ︰ methanol by chlorine by solvent of chloroform-methanol is 100 ︰, 1~0 ︰ 1
Gradient is eluted；The eluent that Lv Fang ︰ methanol is 9 ︰ 1 is collected, Sephadex LH-20 column is crossed after concentration, is elution with methanol
Agent elution crosses ODS column after collecting eluent concentration, collects methanol：Water is 52：48 eluent obtains white without fixed after concentration
Shape powder.
3. oleanane-type triterpene saponin class compound described in claim 1 prevents and treats inflammatory vascular diseases in preparation
Application in drug.
4. a kind of drug for preventing and treating inflammatory vascular diseases, the drug is by oleanane type three described in claim 1
Terpene saponins compound and pharmaceutically acceptable auxiliary material form, wherein the oleanane-type triterpene saponin class compound
Weight percentage be 10%~50%.
5. the drug according to claim 4 for preventing and treating inflammatory vascular diseases, which is characterized in that the drug
It is injection, oral tablet or capsule.
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| CN1709903A (en) * | 2005-06-17 | 2005-12-21 | 中国人民解放军第二军医大学 | Saponin compound and use of its glucoside in preparing medicine for treating neure injure |
| CN101590134A (en) * | 2009-06-30 | 2009-12-02 | 沈阳药科大学 | Has total triterpene of garden burnet root of anti-inflammatory and analgesic effect and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1709903A (en) * | 2005-06-17 | 2005-12-21 | 中国人民解放军第二军医大学 | Saponin compound and use of its glucoside in preparing medicine for treating neure injure |
| CN101590134A (en) * | 2009-06-30 | 2009-12-02 | 沈阳药科大学 | Has total triterpene of garden burnet root of anti-inflammatory and analgesic effect and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| Two New Antiinflammatory Triterpene Saponins from the Egyptian Medicinal Food Black Cumin (Seeds of Nigella sativa);Mohamed Elbandy et al.;《Bull.Korean Chem.Soc.》;20091231;第30卷(第8期);1811-1816 * |
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