CN106892956B - A kind of Ursane triterpene saponin componds and its preparation method and application - Google Patents
A kind of Ursane triterpene saponin componds and its preparation method and application Download PDFInfo
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- CN106892956B CN106892956B CN201510953613.1A CN201510953613A CN106892956B CN 106892956 B CN106892956 B CN 106892956B CN 201510953613 A CN201510953613 A CN 201510953613A CN 106892956 B CN106892956 B CN 106892956B
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- C—CHEMISTRY; METALLURGY
- 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
- C07J63/002—Expansion of ring A by one atom, e.g. A homo steroids
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
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Abstract
The present invention relates to a kind of Ursane triterpene saponin componds, 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 Ursane 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) and inhibit 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.
Ursane triterpene saponin componds are distributed more widely in plant kingdom, according to the literature the term from 1996 to 2012
Between, altogether from nature discovery Ursane triterpene compound about more than 250, (Dinda B, 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 about such compound anti-inflammatory activity is simultaneously
It is not very much, isolated 1 Ursane triterpenoid saponin from the leaf of Gotu Kola (Centella asiatica) in 2011
asiaticoside G(Nhiem NX,Tai BH,Kim YH.A new ursane-type triterpenoid
glycoside from Centella asiatica leaves modulates the production of nitric
oxide and secretion of TNF-αin activated RAW264.7cells.Bioorg Med Chem
Lett.2011,21:1777-1781), and it is found under 100 μM of concentration conditions, in the RAW264.7 cell model of LPS induction
In, the inhibiting rate to NO and TNF-α is respectively 77.3% and 69.0%.2014 from Vitex negundo var cannabifolia (Vitex negundo
Var.cannabifolia three Ursane triterpene saponin compounds (Li MM, Su XQ, Tu are found in leaf)
PF.Anti-inflammatory Ursane-and Oleanane-Type Triterpenoids from Vitex
negundo var.cannabifolia.J Nat Prod,2014,77:2248-2254.), be respectively cannabifolin C,
2 α, 3 α-dihydroxyurs-12,20 (30)-dien-28-oic acid and tormentic acid, and it was found that their energy
Inhibit the expression of NO in LPS induction RAW26437 cell, IC50Value is respectively 34.0,24.9 and 26.1 μM, but gained three
The anti-inflammatory activity of triterpene saponin compound is still undesirable.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of Ursane triterpene saponin componds, and compound treatment is scorching
The significant effect of disease property vascular diseases.
Technical solution the invention solves the above problem is：
A kind of Ursane triterpene saponin componds, molecular structure is as shown in formula I：
The molecular formula C of Ursane triterpene saponin componds of the present invention47H74O17, HR-ESI-MS m/z [M+
Na]+:910.4931, chemical name is 3-O- [β-D- glucopyranosyl-(1 → 2)-β-D- xylopyranosyl] -3 beta-hydroxies
Ursane -12,19 (20)-diene -28- acid-O- β-D- glucopyranoside.
Ursane triterpene saponin componds of the present invention can pass through chemically synthesized method, the skill of this field
Art personnel can determine synthesis step and process conditions by the knowledge of this field.Ursane triterpenoid saponin of the present invention
Class compound can also be isolated from ilex pubescens (Ilex pubescens Hook et Arn.), specific separation method by
Lower step composition：
(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；Collecting Lv Fang ︰ methanol is
The eluent of 85 ︰ 15 crosses Sephadex LH-20 column, using methanol as eluent, crosses ODS column after collecting eluent concentration, receives
Collect the eluent that Jia Chun ︰ water is 66 ︰ 34, white powder crystallization is obtained 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.
Ursane triterpene saponin componds of the present invention have anti-inflammatory effect, can be used for preparing prevention and control
Treat the drug for treating inflammatory vascular diseases.The drug be the Ursane triterpene saponin componds as shown in (I) formula and
The pharmaceutically common dosage form of acceptable auxiliary material composition, e.g., injection, tablet or capsule etc..(I) formula in the preparation
The weight percentage of compound represented is 10%~50%.
Technical effect possessed by Ursane triterpene saponin componds shown in (I) formula is proved below by experiment.
The RAW264.7 cell model induced using lipopolysaccharides (LPS) studies nitric oxide synthetase (iNOS) in compound on intracellular
With the influence of cyclooxygenase-2 (COX-2) expressing quantity, the anti-inflammatory effect of compound of the present invention, specific experiment method are investigated
As described below.
1, sample 1 is from preparation method shown in specific embodiment 1.Reference substance tormentic acid (tormentic acid) is
Document (Li MM, Su XQ, Tu PF.Anti-inflammatory Ursane-and Oleanane-Type
Triterpenoids from Vitex negundo var.cannabifolia.J Nat Prod,2014,77:2248-
2254.) reported compound, shown in concrete structure formula such as following formula (II).Positive control drug DEX is dexamethasone.
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
Tormentic acid is compared, although two compounds are not much different to iNOS inhibiting rate, suppression of the compound 1 to COX-2
Rate processed is obviously greater than tormentic acid.
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 85 ︰ 15, with methanol
For eluent, ODS column is crossed after collecting eluent concentration, collects methanol：Water is 66：34 eluent obtains white after concentration
Color powdery crystal 15mg.
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 C47H74O17, [M+Na]+:910.4931 calculating the molecule according to molecular formula
Degree of unsaturation be 11.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 1,1347 carbon signals are shown altogether in C-NMR spectrum, wherein 17
A to be attributed to sugar, being left 30 carbon signal prompts may be triterpene aglycon.Referring to table 1,17 angular methyls are shown in H-NMR spectrum
Signal [δH0.89,1.09,1.11(6H),1.27,1.60,1.65].One group of four substitution double bond (δC129.0,C-19；δC124.0,
C-20), one group of three substitution double bond (δH5.66,δC128.1,C-12；δC138.1, C-13), an ester carbonyl group (δC176.6,
COOR-28), the anomeric proton signal (δ of an xyloseH4.83,δC106.1, CH-Xyl-1) and the anomeric proton of two glucose
Signal (δH5.37,δC106.3,CH-Glc-1；δH6.34,δC96.1, CH-Glc-1), coupling constant 4.8,7.6 and 8.0
It prompts D- xylose and D-Glucose is beta configuration.Information above prompts the compound that may be while have carboxyl and hydroxyl
Ursane triterpenoid saponin.The carbon modal data compared with known compound oblonganoside B, the two chemical shift is much like,
A glucose signals that difference has been the compound mostly.
Pass through δH5.37 (d, J=7.6Hz, CH-Glc-1) and δCThe long-range related determining carbohydrate side chain of 83.4 (Xyl-C-2) connects
Connecing mode is Glc (1 → 2) Xyl.The structure for sum up determining noval chemical compound is 3-O- [β-D- glucopyranosyl-(1 → 2)-β-
D- xylopyranosyl] -3 beta-hydroxy ursanes -12,19 (20)-diene -28- acid-O- β-D- glucopyranoside.
Referring to Fig. 6, HMBC spectrum display alkene hydrogen δH5.66 (1H, br s, H-12) and δC24.9(C-11)、δC42.4(C-14)
And δC45.0 (C-18) have long-range correlation, methyl δH1.60 (3H, s, H-30) and δC129.0 (C-19) and δC28.9(C-21)
There is long-range correlation, two double bonds is prompted to be respectively between C-12 and C-13 and C-19 and C-20.End group Hydrogen Proton δH4.83
(d, J=4.8Hz, CH-Xyl-1) and δC89.1 (C-3) have long-range correlation, and low field prompt sugar is biased in the chemical shift of C-3
Side chain is connected on the position C-3.The connection type of carbohydrate side chain can pass through δH5.37 (d, J=7.6Hz, CH-Glc-1) and δC83.4
(Xyl-C-2) long-range related determining, i.e. Glc (1 → 2) Xyl.
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) prompt 23-Me and 27-Me is in α, and relevant peaks H-C (24)/H-C (25), H-C (25)/H-C (26) prompt 3 oxygen to take
Generation, 24-Me, 25-Me and 26-Me are in β.The structure for sum up determining noval chemical compound is 3-O- [β-D- glucopyranosyl-(1
→ 2)-β-D- xylopyranosyl] -3 beta-hydroxy ursanes -12,19 (20)-diene -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 Ursane triterpene saponin componds, shown in molecular structure such as following formula (I)：
2. the preparation method of Ursane triterpene saponin componds described in claim 1, this method comprise the steps of：
(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 85 ︰ 15 is collected, Sephadex LH-20 column is crossed after concentration, is to wash with methanol
De- agent elution, crosses ODS column after collecting eluent concentration, collects the eluent that Jia Chun ︰ water is 66 ︰ 34, white powder is obtained after concentration
Last shape crystallization.
3. Ursane triterpene saponin componds described in claim 1 prevent and treat inflammatory vascular diseases medicine in preparation
Application in object.
4. a kind of drug for preventing and treating inflammatory vascular diseases, the drug is by Ursane triterpene described in claim 1
Saponins compound and pharmaceutically acceptable auxiliary material form, wherein the weight of the Ursane triterpene saponin componds
Measuring percentage composition is 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101224215A (en) * | 2007-01-16 | 2008-07-23 | 成都地奥九泓制药厂 | Uses of ursolic acid saponin and oleanolic acid saponin in preparing medicine for increasing white blood cell and/or blood platelet |
| 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 |
| CN102068447A (en) * | 2011-01-10 | 2011-05-25 | 武汉道一堂医药研究院 | Application of triterpenoid saponin compound in preparation of medicaments for treating autoimmune diseases |
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| CN101224215A (en) * | 2007-01-16 | 2008-07-23 | 成都地奥九泓制药厂 | Uses of ursolic acid saponin and oleanolic acid saponin in preparing medicine for increasing white blood cell and/or blood platelet |
| 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 |
| CN102068447A (en) * | 2011-01-10 | 2011-05-25 | 武汉道一堂医药研究院 | Application of triterpenoid saponin compound in preparation of medicaments for treating autoimmune diseases |
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