CN106892957A - 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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Abstract
The present invention relates to a kind of oleanane-type triterpene saponin class compound, shown in the molecular structure such as following formula (I) of the compound.Compound of the present invention is extracted by RADIX ILICIS PUBESCENTIS alcohol reflux and column chromatography separating purification is obtained.Compound of the present invention has anti-inflammatory activity, can be used to prepare the medicine of the inflammatory vascular diseases of prevention and treatment.
Description
Technical field
The present invention relates to steroid, and in particular to the application of pentacyclic triterpenoid and the compound in the inflammatory vascular diseases medicine for the treatment of is prepared.
Background technology
Ilex pubescens is Aquifoliaceae (Aquifoliaceae) Holly Ilex pubescens Hook.et Arn., alias crow tail fourth, June frost, spire Chinese ilex, hair drape over one's shoulders tree, extreme misery medicine, fire and iron wood etc., main product, in Guangdong, Jiangxi, Fujian, Guangxi and other places, is south China conventional Chinese medicine.Its medicinal part is root, with promoting blood circulation and removing obstruction in channels, swelling and pain relieving, it is clearing heat and detoxicating the effect of, be clinically widely used in treatment coronary heart diseases and angina pectoris, Buerger's disease etc..
There is document report to cross antiinflammatory action (the Wang JR at ilex pubescens position,Zhou H,Jiang ZH,Wong YF,Liu 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.),The triterpene saponin componds for having document report therefrom isolated simultaneously have 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 (Xiong Tianqin,Chen Yuanyuan,The anti thrombotic action research of the chivalrous Ilexsaponins B3 of Li Hong,Chinese herbal medicine .2012,43,1758-1788) with suppression 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 during 1996 to 2012, find that oleanane type triterpene class compound exceedes thousands of (Dinda B from nature altogether, Debnath S, Mohanta 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 on such compound anti-inflammatory activity is not especially many, foreign scholar Son (Kwak WJ, Son KH.Loniceroside C, an Antiinflammatory Saponin from Lonicera japonica.Chem.Pharm.Bull.2003,51:333-335.) from the isolated two oleanane type triterpenes class compound of aerial part of honeysuckle (Lonicera japonica), it is respectively Loniceroside A and Loniceroside C, and with its anti-inflammatory activity of croton oil inducing mouse dropsy of ear experimental evaluation, result is displayed under the dosage of 100mg/kg, and its 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.2006,54:6 oleanane type type triterpene compounds 1739-1742.) are found from polygala Japanese polygala (Polygala japonica), in the acute pedal swelling model of carrageenan inducing mouse, 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:Four oleanane type triterpene class compounds 1246-1248.) are found from the seed of horse chestnut (Aesculus chinensis), they are respectively escin 1a, escin 1b, isoescin 1a and isoescin 1b, in dimethylbenzene inducing mouse dropsy of ear model, inhibiting rate is 67.3%-79.3% under the dosage of 30mg/kg.There are scholar (Shi SP, Tu PF.Triterpene Saponins from Clematis mandshurica.J.Nat.Prod.2006,69:Two oleanane type triterpene class compounds 1591-1595) are found from the rhizome of polygonum flaccidum clematis, is respectively clematomandshurica saponins A and B, in LPS inducing mouse peritoneal macrophage models, they suppress 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 compound Heptoleoside B and C 1348-1355) are found from the bark of Ivy Tree Bark, in LPS induction RAW264.7 cell models, under 40 μM of concentration, inhibiting rate to NO is respectively 22.5% and 45.2%, but the anti-inflammatory activity of two oleanane-type triterpene saponin compounds of gained is still undesirable.
The content of the invention
The technical problem to be solved in the present invention provides a kind of oleanane-type triterpene saponin class compound, the effect is significant of the inflammatory vascular diseases of the compounds for treating.
The invention solves the problems that the technical scheme of above mentioned problem is：
A kind of oleanane-type triterpene saponin class compound, its 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 the β of 3-O- β-D- glucopyranosyls -3,19 alpha-dihydroxy oleanane -24- aldehyde radical -12- alkene -28- acid-O- β-D- glucopyranosides.
Oleanane-type triterpene saponin class compound of the present invention can be by the method for chemical synthesis.Those skilled in the art can determine synthesis step and process conditions by the knowledge of this area.Oleanane-type triterpene saponin class compound of the present invention can also be isolated from ilex pubescens (Ilex pubescens Hook et Arn.), and specific separation method is made up of lower step：
(1) RADIX ILICIS PUBESCENTIS is taken, 2h is extracted with the alcohol reflux that 12,10 and 8 times of concentration is 70% successively, merges ethanol extract, reclaimed ethanol and be simultaneously concentrated under reduced pressure into without alcohol taste, obtain total medicinal extract；
(2) total medicinal extract is dissolved in water, crosses D-101 type macroporous resin columns, successively with the ethanol that concentration is 30%, the ethanol that concentration is 60% and ethanol elution that concentration is 95%；The silicagel column that the ethanol eluate that concentration is 60% crosses 200~300 mesh is collected, is eluted by the gradient that the imitative ︰ methyl alcohol of chlorine is the ︰ 1 of 100 ︰ 1~0 by solvent of chloroform-methanol；Collect the eluent that Lv Fang ︰ methyl alcohol is 9 ︰ 1 and cross Sephadex LH-20 posts, with methyl alcohol as eluent, ODS posts are crossed after collecting eluent concentration, collect methyl alcohol：Water is 52：48 eluent, obtains white powder crystallization after concentration.
The concentration of the ethanol described in above-mentioned separation method is volumetric concentration.
Ilex pubescens described in above-mentioned separation method is the dry root of Aquifoliaceae (Aquifoliaceae) Ilex (Ilex) plant ilex pubescens.
Oleanane-type triterpene saponin class compound of the present invention, with antiinflammatory action, can be used to prepare the medicine of the prevention and treatment inflammatory vascular diseases for the treatment of.Described medicine oleanane-type triterpene saponin class compound and conventional formulation that pharmaceutically acceptable auxiliary material is constituted shown in (I) formula, e.g., injection, tablet or capsule etc..The weight percentage of the compound in the preparation shown in (I) formula is 10%~50%.
The technique effect that oleanane-type triterpene saponin class compound shown in (I) formula has is proved below by experiment.The RAW264.7 cell models induced using lipopolysaccharides (LPS), the influence of nitric oxide synthetase (iNOS) and cyclooxygenase-2 (COX-2) expressing quantity in research compound on intracellular, the antiinflammatory action of compound of the present invention is investigated, specific experiment method is as described below.
Material and method
1st, sample 1 derives from preparation method shown in specific embodiment 1.Reference substance clematomandshurica saponins B are document (Shi SP, Tu PF.Triterpene Saponins from Clematis mandshurica.J.Nat.Prod.2006,69:Compound 1591-1595) is reported, shown in concrete structure formula such as following formula (II).Positive control drug DEX is dexamethasone.
clematomandshurica saponins B
2nd, macrophage RAW264.7 in mouse source is purchased from American Type Culture Collection, in being stored in containing 10%FBS, 100units/ml Benzylpenicillin, 100mg/ml streptomysins and 2mM L- l-glutamine nutrient solutions, in saturated humidity, 37 DEG C, 5%CO2Under the conditions of cultivate.
3rd, compound is dissolved in DMSO, and mother liquid concentration is made into 30mM, and working concentration is 30 μM.
4th, RAW264.7 cells are with 8 × 10424h is cultivated in individual/hole in being inoculated in 24 orifice plates, and then cell stimulates 18h by (0.5 μM) pretreatment 1h of test sample and positive control drug dexamethasone with the LPS of 100ng/ml, if blank combination normal group.
5th, Western Blot methods：After LPS stimulates, total protein of cell is extracted with the RIPA lysates containing protease inhibitors, concentration is measured by Bio-Rad protein quantitative methods, transferring film after gel electrophoresis, 5% skim milk is closed, then iNOS, COX-2 primary antibody and mouse the specific antibody overnight incubation under the conditions of 4 DEG C are used, room temperature secondary antibody is incubated, and protein expression content is analyzed with Odyssey v3.0 softwares.
6th, statistical analysis：Above-mentioned testing result represents that sample combination blank control group data carry out statistics credit analysis, and P ＜ 0.05 are represented has significant difference with X ± S.
INOS the and COX-2 protein expression inhibiting rates of table 1
Above test result indicate that compound 1 can conspicuousness suppress LPS induction RAW264.7 cells in iNOS and COX-2 albumen expression.Show that the compound is respectively provided with preferably section antiinflammatory action.Simultaneously compared with compound clematomandshurica saponins B have been reported, although two compounds are more or less the same to COX-2 inhibiting rates, but compound 1 is substantially greater than clematomandshurica saponins B to the inhibiting rate of iNOS, that is to say, that the characteristics of compound 1 has many targets.
Brief description of the drawings
Fig. 1 compounds of the present invention1H-NMR schemes (400MHz).
Fig. 2 compounds of the present invention13C-NMR schemes (100MHz).
The DEPT figures of Fig. 3 compounds of the present invention.
The COSY NMR figures of Fig. 4 compounds of the present invention.
The HSQC NMR figures of Fig. 5 compounds of the present invention.
The HMBC NMR figures of Fig. 6 compounds of the present invention.
The NOESY NMR figures of Fig. 7 compounds of the present invention.
Specific embodiment
Following experiments pick up from Conghua City of Guangdong Province with ilex pubescens (Ilex pubescens Hook et Arn.) root.
Example 1：
First, the preparation of compound
(1) RADIX ILICIS PUBESCENTIS is taken, 2h is extracted with the alcohol reflux that 12,10 and 8 times of concentration is 70% successively, merges ethanol extract, ethanol reclaimed after filtering and is concentrated under reduced pressure into without alcohol taste, obtain total medicinal extract 2.2kg；
(2) total medicinal extract is dissolved in water, crosses D-101 type macroporous resin columns, successively with the ethanol that concentration is 30%, the ethanol that concentration is 60% and ethanol elution that concentration is 95%；Collect the ethanol eluate that concentration is 60% and solvent is recovered under reduced pressure, obtain thick medicinal extract 566g, the thick medicinal extract crosses the silicagel column of 200~300 mesh, eluted by the gradient that the imitative ︰ methyl alcohol of chlorine is the ︰ 1 of 100 ︰ 1~0 by solvent of chloroform-methanol；Sephadex LH-20 posts are crossed after collecting the eluent concentration that Lv Fang ︰ methyl alcohol is 9 ︰ 1, with methyl alcohol as eluent, ODS posts is crossed after collecting eluent concentration, collect methyl alcohol：Water is 52：48 eluent, obtains white powder crystallization 16mg after concentration.
2nd, the identification of compound
Resulting white powder crystallization Liebermann-Burchard reactions are positive, and finally show aubergine, illustrate that it is triterpene compound.
Referring to Fig. 1~5, IR shows hydroxyl group absorption (3429cm-1), carbonyl absorption (1705cm-1), double bond absorbs (1632cm-1).High resolution mass spectrum provides molecular formula C41H64O14, [M+Na]+:803.4190, the degree of unsaturation for calculating the molecule according to molecular formula is 9.The compound is analyzed with TLC and HPLC after derivatization and compareed with the derivative of saccharide by sour water solution, it was demonstrated that its sugar unit is D- xyloses and D-Glucose.Referring to table 1,1341 carbon signals are shown altogether in C-NMR spectrums, wherein 11 are attributed to sugar, it may be triterpene aglycon to be left 30 carbon signal promptings.Referring to table 1,16 angular methyl signal [δ are shown in H-NMR spectrumsH0.79,0.96,1.08,1.16,1.60,1.63].One group of three substitution double bond (δH 5.51,δC123.6,C-12；δC144.2, C-13), an aldehyde radical (δH 10.38,δC206.4, CHO-24), an ester carbonyl group (δC177.6, COOR-28), an anomeric proton signal (δ for xyloseH 4.84,δC108.2, CH-Xyl-1) and an anomeric proton signal (δ for glucoseH 6.36,δC96.2, CH-Glc-1), its coupling constant is that 7.2 and 8.0 prompting D- xyloses and D-Glucose are beta configuration.It may be while having the oleanane-type triterpene saponin of carboxyl, aldehyde radical and hydroxyl that information above points out the compound.Compare carbon modal data with known compound ilexpublesnin L, both chemical shifts are much like, 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)、δC42.4 (C-14) and δC45.0 (C-18) have long-range correlation, point out double bond to be between C-12 and C-13.HMBC spectrum displays connect oxygen hydrogen δH3.59 (1H, m, H-19) and δC46.8 (C-17) and δC29.1 (C-29) have long-range correlation, point out hydroxyl to be in C-19.HMBC spectrum displays δH4.84 (d, J=7.2Hz, CH-xyl-1) and δC87.0 (C-3) have long-range related determination xylose to be connected on C-3 positions.
Referring to Fig. 7, ROESY spectrums show 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) to point out 19 oxygen substitutions, 23-Me and 27-Me to be in α, and relevant peaks H-C (24)/H-C (25), H-C (25)/H-C (26), H-C (19)/H-C (30) point out 3 oxygen substitutions, 24-CHO, 25-Me, 26-Me and 30-Me to be in β.The structure for sum up determining noval chemical compound is the β of 3-O- β-D- glucopyranosyls -3,19 alpha-dihydroxy oleanane -24- aldehyde radical -12- alkene -28- acid-O- β-D- glucopyranosides.
The chemical compounds I of table 21H NMR and13C NMR datas (Pyridine-d5, J=Hz)
Example 2：(injection)
Take the compound 1000mg obtained using the methods described of above-described embodiment 1, plus 1000ml water for injection, adjust pH value to 7~7.5 with sodium carbonate, it is stirred to dissolve, degerming filtration, embedding, through 100 DEG C of 15 minutes flowing steam sterilizations, the parenteral solution for being made every 2mg/2ml is used for injection.
Example 3：(capsule)
The auxiliary materials such as the compound 5000mg and 4000mg microcrystalline celluloses, 500mg sodium carboxymethyl starches, the 400mg lauryl sodium sulfate that are obtained using the methods described of above-described embodiment 1 are taken to be sufficiently mixed, dry granulation is carried out using roll-in method, mixed with appropriate magnesium stearate again, 3# Capsuleses are packed into, the capsule that specification is 100mg/ are made and are supplied to orally use.
Example 4：(tablet)
The compound 5000mg obtained using the methods described of above-described embodiment 1 is taken to be well mixed with 4000mg starch, 200mg cross-linked pvps, 300mg sodium carboxymethyl starches, with 75% ethanol solution of 5%PVP as adhesive, softwood processed, pelletized with 18 mesh sieves, 1h after 60 DEG C of dryings, adds appropriate talcum powder after 20 mesh whole grains, mix, compressing tablet, is made the tablet that specification is 100mg/ pieces and supplies to orally use.
Claims (5)
1. a kind of oleanane-type triterpene saponin class compound, shown in its molecular structure such as following formula (I)：
2. the preparation method of the oleanane-type triterpene saponin class compound described in claim 1, the method is made up of lower step：
(1) RADIX ILICIS PUBESCENTIS is taken, 2h is extracted with the alcohol reflux that 12,10 and 8 times of concentration is 70% successively, is merged ethanol and is carried
Liquid is taken, ethanol is reclaimed and is concentrated under reduced pressure into without alcohol taste, obtain total medicinal extract；
(2) total medicinal extract is dissolved in water, D-101 type macroporous resin columns is crossed, successively with the ethanol, concentration that concentration is 30%
For 60% ethanol and concentration be 95% ethanol elution；Collect the silicon that the ethanol eluate that concentration is 60% crosses 200~300 mesh
Glue post, is eluted by solvent of chloroform-methanol by the gradient that Lv Fang ︰ methyl alcohol is the ︰ 1 of 100 ︰ 1~0；Collect Lv Fang ︰ methyl alcohol
For the eluent of 9 ︰ 1 crosses Sephadex LH-20 posts, with methyl alcohol as eluent, ODS is crossed after collecting eluent concentration
Post, collects methyl alcohol：Water is 52：48 eluent, obtains white amorphous powder after concentration.
3. the oleanane-type triterpene saponin class compound described in claim 1 is preparing the inflammatory vascular diseases medicine of prevention and treatment
Application in thing.
4. a kind of medicine for preventing and treating inflammatory vascular diseases, the medicine is as the oleanane type triterpene described in claim 1
Saponins compound and pharmaceutically acceptable auxiliary material composition, wherein the weight of described oleanane-type triterpene saponin class compound
Amount percentage composition is 10%~50%.
5. the medicine of the inflammatory vascular diseases of prevention and treatment according to claim 4, it is characterised in that described medicine
It is injection, oral tablet or capsule.
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Cited By (2)
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| WO2020126627A1 (en) * | 2018-12-21 | 2020-06-25 | Sapreme Technologies B.V. | Improved cell-targeting binding molecule |
| CN113683657A (en) * | 2021-09-26 | 2021-11-23 | 中国中医科学院中药研究所 | Oleanolic alkyl type triterpenoid saponin and preparation method and application thereof |
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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 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2020126627A1 (en) * | 2018-12-21 | 2020-06-25 | Sapreme Technologies B.V. | Improved cell-targeting binding molecule |
| CN113683657A (en) * | 2021-09-26 | 2021-11-23 | 中国中医科学院中药研究所 | Oleanolic alkyl type triterpenoid saponin and preparation method and application thereof |
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