CN106892958A - A kind of exocyclic double bond Ursane triterpene saponin componds and its preparation method and application - Google Patents
A kind of exocyclic double bond Ursane triterpene saponin componds and its preparation method and application Download PDFInfo
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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
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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- C—CHEMISTRY; METALLURGY
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C07H1/08—Separation; Purification from natural products
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- 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
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Abstract
The present invention relates to a kind of exocyclic double bond Ursane triterpene saponin componds, 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 pentacyclic triterpenoid and the compound are preparing treatment inflammation
Application in disease property vascular diseases medicine.
Background technology
Ilex pubescens is Aquifoliaceae (Aquifoliaceae) Holly Ilex pubescensHook.etArn., alias
Black 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,
It is south China conventional Chinese medicine.Its medicinal part be root, with promoting blood circulation and removing obstruction in channels, swelling and pain relieving, it is clearing heat and detoxicating the effect of, clinically
It is widely used in treatment coronary heart diseases and angina pectoris, Buerger's disease etc..
There is document report to cross antiinflammatory action (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 the Ursane triterpene saponin componds for having document report therefrom isolated have it is antitumor (ZhouY,
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 (the chivalrous Ilexsaponins B3 of Xiong Tianqin, Chen Yuanyuan, Li Hong anti thrombotic action research, 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.
Ursane triterpene saponin componds are distributed more widely in plant kingdom, according to the literature from 1996 to 2012 terms
Between, Ursane triterpene compound about more than 250 is found from nature altogether, (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 on such compound anti-inflammatory activity is simultaneously
It is not a lot, isolated 1 Ursane triterpenoid saponin from the leaf of Gotu Kola (Centellaasiatica) in 2011
asiaticoside G(Nhiem NX,Tai BH,Kim YH.A new ursane-type triterpenoid
glycoside from Centellaasiatica leaves modulates the production of nitric
oxide and secretion of TNF-αin activated RAW264.7 cells.Bioorg Med Chem
Lett.2011,21:1777-1781), and it is found under 100 μM of concentration conditions, in the RAW264.7 cell models of LPS inductions
In, the inhibiting rate to NO and TNF-α is respectively 77.3% and 69.0%.2014 from Vitex negundo var cannabifolia (Vitexnegundo
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 Vitexnegundo
var.cannabifolia.J Nat Prod,2014,77:2248-2254.), it is respectively cannabifolin C, 2 α, 3 α-
Dihydroxyurs-12,20 (30)-dien-28-oic acid and tormentic acid, and it was found that they can suppress LPS
The expression of NO, its IC in induction RAW26437 cells50Respectively 34.0,24.9 and 26.1 μM of value, but three triterpene soaps of gained
The anti-inflammatory activity of glycoside compound is still undesirable.
The content of the invention
The technical problem to be solved in the present invention provides a kind of exocyclic double bond Ursane triterpene saponin componds, the chemical combination
Thing treats the effect is significant of inflammatory vascular diseases.
The invention solves the problems that the technical scheme of above mentioned problem is：
A kind of exocyclic double bond Ursane triterpene saponin componds, its molecular structure is as shown in formula I：
The molecular formula C of exocyclic double bond Ursane triterpene saponin componds of the present invention47H74O17, HR-ESI-MS
m/z[M+Na]+:910.4930, chemical name is 3-O- [β-D- glucopyranosyls-(1 → 2)-β-D- xylopyranosyls] -3
(29)-diene -28- acid-O- β-D- glucopyranosides of beta-hydroxy ursane -12,19.
Exocyclic double bond Ursane triterpene saponin componds of the present invention can be by the method for chemical synthesis.This
The technical staff in field can determine synthesis step and process conditions by the knowledge of this area.Exocyclic double bond of the present invention
Ursane triterpene saponin componds can also be separated from ilex pubescens (Ilex pubescens Hook et Arn.)
Arrive, 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, 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；Collecting Lv Fang ︰ methyl alcohol is
The eluent of 85 ︰ 15 crosses Sephadex LH-20 posts, with methyl alcohol as eluent, ODS posts is crossed after collecting eluent concentration, receives
Collection methyl alcohol：Water is 7：3 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 Aquifoliaceae (Aquifoliaceae) Ilex (Ilex) vegetable hair winter
Blue or green dry root.
Exocyclic double bond Ursane triterpene saponin componds of the present invention, with antiinflammatory action, can be used to prepare
The medicine of the inflammatory vascular diseases of prevention and treatment treatment.Described medicine is the exocyclic double bond Ursane three as shown in (I) formula
Terpene saponins compound and the pharmaceutically conventional formulation of acceptable auxiliary material composition, e.g., injection, tablet or capsule
Deng.The weight percentage of the compound in the preparation shown in (I) formula is 10%~50%.
The skill that exocyclic double bond Ursane triterpene saponin componds shown in (I) formula have is proved below by experiment
Art effect.The RAW264.7 cell models induced using lipopolysaccharides (LPS), nitric oxide synthetase in research compound on intracellular
(iNOS) and cyclooxygenase-2 (COX-2) expressing quantity influence, investigate the antiinflammatory action of compound of the present invention, it is specific real
Proved recipe method is as described below.
1st, sample 1 derives 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 Vitexnegundo var.cannabifolia.J Nat Prod,2014,77:2248-
2254.) compound is reported, shown in concrete structure formula such as following formula (II).Positive control drug DEX is dexamethasone.
2nd, macrophage RAW264.7 in mouse source is purchased from American Type Culture Collection, is stored in and contains 10%FBS, 100units/ml
In Benzylpenicillin, 100mg/ml streptomysins and 2mM L- l-glutamine nutrient solutions, in saturated humidity, 37 DEG C, 5%CO2Condition
Lower culture.
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 cell is by test sample and sun
Property (0.5 μM) pretreatment 1h of comparison medicine dexamethasone, then stimulate 18h with the LPS of 100ng/ml, if blank combination normal group.
5th, Western Blot methods：It is with the RIPA lysates containing protease inhibitors that cell is total after LPS stimulates
Protein extraction out, concentration is measured by Bio-Rad protein quantitative methods, and transferring film after gel electrophoresis, 5% skim milk is carried out
Closing, then with iNOS, COX-2 primary antibody and mouse specific antibody under the conditions of 4 DEG C overnight incubation, room temperature secondary antibody be incubated, albumen
Expression contents are analyzed with Odyssey v3.0 softwares.
6th, statistical analysis：Above-mentioned testing result represents that sample combination blank control group data carry out statistics with X ± S
Credit is analysed, and P ＜ 0.05 are represented has significant difference.
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
The expression of COX-2 albumen.Show that the compound is respectively provided with preferably section antiinflammatory action.Simultaneously with reported compound
Tormentic acid are compared, although two compounds are more or less the same to iNOS inhibiting rates, but suppression of the compound 1 to COX-2
Rate processed is substantially greater than tormentic acid.
Brief description of the drawings
Fig. 1 compounds of the present invention1H-NMR schemes (500MHz).
Fig. 2 compounds of the present invention13C-NMR schemes (150MHz).
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, is merged ethanol and is carried
Liquid is taken, ethanol is 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, 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 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, with chloroform-methanol as solvent press the imitative ︰ methyl alcohol of chlorine be 100 ︰ 1~
The gradient of 0 ︰ 1 is eluted；Sephadex LH-20 posts are crossed after collecting the eluent concentration that Lv Fang ︰ methyl alcohol is 85 ︰ 15, with first
Alcohol is eluent, and ODS posts are crossed after collecting eluent concentration, collects methyl alcohol：Water is 7：3 eluent, obtains white after concentration
The powdered crystallization 116mg of color.
2nd, the identification of compound
Resulting white sprills crystallization Liebermann-Burchard reactions are positive, and finally show aubergine, say
Bright its 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 C47H74O17, [M+Na]+:910.4930, the molecule is calculated according to molecular formula
Degree of unsaturation be 11.The compound analyzed with TLC and HPLC by sour water solution, after derivatization and with the derivative of saccharide
Control, it was demonstrated that its sugar unit is D- xyloses and D-Glucose.Referring to table 1,1347 carbon signals are shown altogether in C-NMR spectrums, wherein 17
Individual to be attributed to sugar, it may be triterpene aglycon to be left 30 carbon signal promptings.Referring to table 1,16 angular methyls are shown in H-NMR spectrums
Signal [δH0.87,1.05,1.06,1.08,1.24,1.25(3H,s)].One group end double bond (δC153.5,C-20；δH5.05,
δC113.0, C-29), one group of three substitution double bond (δH5.46,δC127.8,C-12；δC137.7, C-13), an ester carbonyl group (δC176.4, COOR-28), an anomeric proton signal (δ for xyloseH4.81,δC106.0, CH-Xyl-1) and two glucose
Anomeric proton signal (δH5.34,δC106.1,CH-Glc-1；δH6.28,δC96.1, CH-Glc-1), its coupling constant be 5.6,
7.2 and 8.0 prompting D- xyloses and D-Glucose are beta configuration.It may be while having carboxyl that information above points out the compound
With the exocyclic double bond Ursane triterpenoid saponin of hydroxyl.With known compound 3 β-hydroxyurs-12,19 (29)-dien-28-
Oic acid β-D-glucopyranosylester compare carbon modal data, and both chemical shifts are much like, and difference is the chemical combination
The many individual sugared side chains of thing.
Referring to Fig. 6, HMBC spectrum display alkene hydrogen δH5.46 (1H, br s, H-12) and δC24.1(C-11)、δC43.0(C-14)
And δC47.4 (C-18) have a long-range correlation, end alkene hydrogen δH5.05 (2H, br d, 7.6Hz, H-29) and δC47.4 (C-18) and
δC37.5 (C-20) have long-range correlation, point out two double bonds to be respectively between C-12 and C-13 and C-19 and C-29.End group
Hydrogen Proton δH4.81 (d, J=5.6Hz, CH-Xyl-1) and δC89.1 (C-3) have long-range correlation, and the chemical shift of C-3 is partial to
The sugared side chain of low field prompting is connected on C-3 positions.The connected mode of sugared side chain can be by δH5.34 (d, J=7.2Hz, CH-Glc-
And δ 1)CThe long-range related determination of 83.2 (Xyl-C-2), i.e. Glc (1 → 2) Xyl.
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) promptings 23-Me and 27-Me is in α, relevant peaks H-C (24)/H-C (25), H-C (25)/H-C
(26) 3 oxygen substitutions, 24-Me, 25-Me, 26-Me and 30-Me are pointed out to be in β.The structure for sum up determining noval chemical compound is 3-
O- [β-D- glucopyranosyls-(1 → 2)-β-D- xylopyranosyls] (29)-diene -28- of -3 beta-hydroxy ursane -12,19
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, use carbonic acid
Sodium adjusts pH value to 7~7.5, is stirred to dissolve, degerming filtration, embedding, through 100 DEG C of 15 minutes flowing steam sterilizations, is made every
The parenteral solution of 2mg/2ml is used for injection.
Example 3：(capsule)
Take the compound 5000mg and 4000mg microcrystalline celluloses, 500mg carboxylics obtained using the methods described of above-described embodiment 1
The auxiliary materials such as methyl starch sodium, 400mg lauryl sodium sulfate are sufficiently mixed, and dry granulation is carried out using roll-in method, then with right amount
Magnesium stearate is mixed, and is packed into 3# Capsuleses, is made the capsule that specification is 100mg/ and is supplied to orally use.
Example 4：(tablet)
Take the compound 5000mg that is obtained using the methods described of above-described embodiment 1 and 4000mg starch, 200mg cross-linked pvps,
300mg sodium carboxymethyl starches are well mixed, with 75% ethanol solution of 5%PVP as adhesive, softwood processed, with 18 mesh sieve series
Grain, 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
Orally use.
Claims (5)
1. a kind of exocyclic double bond Ursane triterpene saponin componds, shown in its molecular structure such as following formula (I)：
2. the preparation method of the exocyclic double bond Ursane triterpene saponin componds described in claim 1, the method is by lower step
Rapid composition：
(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 extracted
Liquid, reclaims ethanol and is concentrated under reduced pressure into without alcohol taste, obtains total medicinal extract；
(2) total medicinal extract is dissolved in water, crosses D-101 type macroporous resin columns, be with the ethanol, concentration that concentration is 30% successively
60% ethanol and concentration are 95% ethanol elution；Collect the silica gel that the ethanol eluate that concentration is 60% crosses 200~300 mesh
Post, is eluted by solvent of chloroform-methanol by the gradient that Lv Fang ︰ methyl alcohol is the ︰ 1 of 100 ︰ 1~0；It is 85 ︰ to collect Lv Fang ︰ methyl alcohol
15 eluent crosses Sephadex LH-20 posts, with methyl alcohol as eluent, ODS posts is crossed after collecting eluent concentration, collects
Methyl alcohol：Water is 7：3 eluent, obtains white powder crystallization after concentration.
3. the exocyclic double bond Ursane triterpene saponin componds described in claim 1 are preparing the inflammatory blood of prevention and treatment
Application in pipe disease medicament.
4. a kind of medicine for preventing and treating inflammatory vascular diseases, the medicine is as the exocyclic double bond Usu described in claim 1
Alkane type triterpenoid saponins compound and pharmaceutically acceptable auxiliary material composition, wherein described exocyclic double bond Ursane triterpene
The weight percentage of saponins compound 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586563A (en) * | 2018-06-25 | 2018-09-28 | 广州中医药大学(广州中医药研究院) | A kind of Ursane triterpene saponin componds of E ring openings and preparation method thereof |
| CN111825739A (en) * | 2018-06-25 | 2020-10-27 | 广东药科大学 | Anti-inflammatory triterpenoid saponin compound and extraction method and application thereof |
| CN114380882B (en) * | 2021-12-22 | 2023-07-04 | 国珍健康科技（北京）有限公司 | Ursane type triterpene compound and preparation method and application thereof |
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| CN1593436A (en) * | 2003-09-08 | 2005-03-16 | 成都地奥制药集团有限公司 | Application of ursane type triterpenoid saponin in the preparing process of leucocyte and/or platelet increasing medicine |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1593436A (en) * | 2003-09-08 | 2005-03-16 | 成都地奥制药集团有限公司 | Application of ursane type triterpenoid saponin in the preparing process of leucocyte and/or platelet increasing medicine |
| 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 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586563A (en) * | 2018-06-25 | 2018-09-28 | 广州中医药大学(广州中医药研究院) | A kind of Ursane triterpene saponin componds of E ring openings and preparation method thereof |
| CN108586563B (en) * | 2018-06-25 | 2020-01-31 | 广州中医药大学(广州中医药研究院) | Ursolic triterpenoid saponin compounds with E-ring cleavage and preparation method thereof |
| CN111825739A (en) * | 2018-06-25 | 2020-10-27 | 广东药科大学 | Anti-inflammatory triterpenoid saponin compound and extraction method and application thereof |
| CN111825739B (en) * | 2018-06-25 | 2022-06-10 | 广东药科大学 | Anti-inflammatory triterpenoid saponin compound and extraction method and application thereof |
| CN114380882B (en) * | 2021-12-22 | 2023-07-04 | 国珍健康科技（北京）有限公司 | Ursane type triterpene compound and preparation method and application thereof |
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