CN102304158B - Acylated flavonoid glycoside compounds and application thereof in preparation of complement inhibitor medicines - Google Patents
Acylated flavonoid glycoside compounds and application thereof in preparation of complement inhibitor medicines Download PDFInfo
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Abstract
The invention discloses acylated flavonoid glycoside compounds shown as a formula I and application thereof in preparation of complement inhibitor medicines. Acylated flavonoid glycosides extracted and separated from cudweed herb are proved to inhibit hemolysis caused by activation of a complement system in a classical pathway through in vitro experiments, and have complement inhibition effect; the activity of each monomericcompound is higher than that of a total extract of cudweed herb; and the acylated flavonoid glycoside compounds are good complement inhibitors and have low effective concentration, can serve as active ingredients to prepare novel complement inhibitor medicines for treating various diseases caused by abnormal activation of complements, are low in toxicity, safe in administration and rich in raw material sources and have great clinical application value. The structure of the formula I is shown as the specifications, wherein R1 and R2 are same or different, and respectively H, OH or OCH3; and R3 and R4 are respectively H or groups shown in the specifications.
Description
Technical field
The present invention relates to complement inhibitor medicine, be specifically related to acylated flavonoid glycoside compounds and in the application of preparing in anticomplement medicament.
Background technology
Complement system is one of immune defense system of wanting of body weight for humans.Under normal physiological condition, the function of complement is mainly attack external cause of disease and remove immunocomplex, and maintains organism balance.But the improper activation of complement system can cause human immune system's overreaction, cause damage and the inflammatory reaction of human body self healthy tissues, be the important medium of autoimmune inflammation reaction.More and more evidence shows, generation, the development of inflammatory disease are relevant with the activation of complement.Therefore, how to disturb and to suppress the damage that complement activation produces, becoming one of focus of pharmaceutical research.
Prove at present, the various diseases such as rheumatoid arthritis, cerebral apoplexy, ephritis, systemic lupus erythematous, senile dementia, ischemic damage and reperfusion, acute myocardial infarction, acute respiratory distress syndrome are all relevant to the excessive activation of complement.Multiple complement inhibitor just under study for action, is applied to clinically in the monoclonal antibody of the existing complement receptor (CR) of the U.S. and anti-C5a, obtain good curative effect.Although but these systemic complement inhibitors have improved inflammatory reaction, because complement system has important defense reaction in body, produce general complement and suppress simultaneously, therefore, prolonged application can reduce the defence capability of body, produces multiple complications, also causes the potential side effects such as infection.In order to give full play to the curative effect of complement inhibitor, reduce untoward reaction, people are trying to explore the novel complement inhibitor of high-efficiency low-toxicity in natural product.
The progress of anticomplementary activity composition in natural product in recent years, be not difficult to find out the anticomplementary activity composition that has separated various structures type from natural product, mainly contain flavones, polysaccharide and terpenoid, wherein acylated flavonoid glycoside has significant restraining effect to complement system, and widely distributed in natural phant, at feverfew Baikal Gnaphalium affine (Gnaphalium uliginosum) (Phytochemistry Letters, 2010, 3:45-47), polygonaceae plant pale persicaria (Persicaria lapathifolia) (Chem.Pharm.Bull.1999, 47 (10): 1484-1486), Magnoliacea plant Flos Magnoliae (Magnolia fargesii) (Biol.Pharm.Bull.1998, 21 (10): 1077-1078), leguminous plants donkey food grass (Onobrychis viciifolia) (Phytochemistry, 2011, 72:423-429) with Kent basic note Chinese scholartree (Cladrastis kentukea) (Phytochemistry, 2011, 72:372-384) and pinaceae plant newveitch spruce (Picea neoveitchii) (Phytochemistry, 2011, 72:490-494) etc. in plant, all there is distribution.The pharmacological actions such as that this compounds has is antimycotic, cell toxicant, but the acylated flavonoid glycoside anticomplement of so far there are no Flavone aglycone-4 '-sugar-aromatic ring structure or Flavone aglycone-7-sugar-aromatic ring structure and prepare the report of complement suppressive drug.
The inventor once studied and had reported that Gnaphalium affine extract was for pharmacy (Chinese Patent Application No.: 201110059384.0); now further research finds that the monomer new compound acylated flavonoid glycoside that separation obtains from Gnaphalium affine has significant anticomplementary activity, and the activity of each monomeric compound is all better than the activity of Gnaphalium affine total extract.
Summary of the invention
Technical problem to be solved by this invention is to overcome above-mentioned weak point, and the acylated flavonoid glycoside that research and design is new is prepared complement suppressive drug.
The invention provides a kind of acylated flavonoid glycoside compounds in the application of preparing in anticomplement medicament.
Described acylated flavonoid glycoside compounds has the chemical structure of formula I:
Formula I
Wherein R
1, R
2can be identical or different, can be respectively H, OH or OCH
3;
R
3, R
4difference, can be respectively H or for following groups:
Acylated flavonoid glycoside compounds preferred for this invention comprises following compounds:
Apigenin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 1;
Luteolin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 2;
Quercetin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 3;
Apigenin-7-O-beta-D-(6 " E-coffee acyl)-glucose 4.
Wherein compound 1,2,3 for separating the new compound obtaining from Gnaphalium affine.
Above-claimed cpd by HR-ESI-MS, IR,
1h-NMR (DMSO-d
6, 600MHz),
13c-NMR (DMSO-d
6, 150MHz) etc. detection, confirmed their structure.
Acylated flavonoid glycoside compounds of the present invention, through in vitro tests, confirmation can suppress classical pathway of complement and activate the cell haemolysis causing; there is significant anticomplementary activity; the activity of each monomeric compound is all better than the activity of Gnaphalium affine total extract, thereby, can be used for preparing anticomplement medicament.
Above-claimed cpd of the present invention separates and obtains from Gnaphalium affine, prepares by following method:
Gnaphalium affine herb 25kg pulverizes, and 80% alcohol heat reflux extracts 3 times, obtains stepwise solvent extraction after medicinal extract, obtains sherwood oil, ethyl acetate, propyl carbinol and four parts of water liquid.Ethyl acetate extract is through silica gel (100～200 order) column chromatography, with methylene dichloride: methyl alcohol (70: 1,50: 1,30: 1,20: 1,10: 1,5: 1,3: 1,1: 1) gradient elution, collect methylene dichloride: methyl alcohol (10: 1) wash-out stream part is carried out repeatedly silica gel column chromatography, reversed-phase column chromatography purifying, separates and obtains compound 1,2,3,4.
The Gnaphalium affine that the present invention uses obtains by commercially available.
The pharmaceutical composition that medicine of the present invention is made up of as activeconstituents and pharmaceutical carrier formula I compound.
The pharmaceutical composition that medicine of the present invention is made up of as activeconstituents and pharmaceutical carrier apigenin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 1.
The pharmaceutical composition that medicine of the present invention is made up of as activeconstituents and pharmaceutical carrier luteolin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 2.
The pharmaceutical composition that medicine of the present invention is made up of as activeconstituents and pharmaceutical carrier Quercetin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside 3.
The pharmaceutical composition that medicine of the present invention is made up of as activeconstituents and pharmaceutical carrier apigenin-7-O-beta-D-(6 " E-coffee acyl)-glucose 4.
Pharmaceutical composition of the present invention has significant anticomplementary activity, can be used for the various diseases that the improper activation of complement causes.
Acylated flavonoid glycoside of the present invention; there is significant anticomplementary activity; the activity of each monomeric compound is all better than the activity of Gnaphalium affine total extract; be the good complement inhibitor of a class, can be used for the various diseases that the improper activation of complement causes, and effective concentration be low; toxicity is low; drug safety, raw material sources are abundant, have larger clinical value.
Embodiment
The present invention is further described to use indefiniteness embodiment below.
Embodiment 1 prepares acylated flavonoid glycoside compounds
Gnaphalium affine is dried herb (being purchased from medicinal material market, Chinese Hui nationality) 25kg and pulverizes, 80% alcohol heat reflux extracts three times (200L × 3), united extraction liquid reclaims ethanol, 60 DEG C are evaporated to dry, obtain Gnaphalium affine total extract medicinal extract 2.9kg, get total extract 2.5kg water (15L) suspendible, use successively isopyknic sherwood oil, ethyl acetate, n-butanol extraction 3 times, concentrated 60 DEG C of combined ethyl acetate extraction liquid is decompressed to dryly, obtains acetic acid ethyl ester extract 450g.Get acetic acid ethyl ester extract 400g through silicagel column (4kg, 100～200 orders, 10cm × 100cm) chromatogram is with methylene dichloride: methyl alcohol (70: 1, 50: 1, 30: 1, 20: 1, 10: 1, 5: 1, 3: 1, 1: 1) gradient elution, each gradient elution 20L, collect methylene dichloride: methyl alcohol (10: 1) wash-out stream part 20L, 60 DEG C are evaporated to dry, obtain 80g medicinal extract, again through silicagel column (1kg, 200～300 orders, 10cm × 60cm) chromatography, with methylene dichloride: methyl alcohol (30: 1, 20: 1, 15: 1, 10: 1, 5: 1, 3: 1, 1: 1, 0: 1) wash-out, each gradient elution 10L, obtain 8 stream part (Fr
1-Fr
8).Stream part Fr
7(23.3g) through reverse phase silica gel post (125g, 5cm × 20cm) methanol/water (1: 4, 1: 2, 1: 1, 3: 2, 4: 1, pure methyl alcohol) gradient elution, each gradient elution 2L, obtain I-VI6 stream part, wherein stream part III (4.5g) is again through reverse phase silica gel post (100g, 5cm × 15cm) methanol/water (2: 3) purifying 2 times repeatedly, each purifying eluting solvent amount is 1.5L, 60 DEG C of decompression and solvent recoveries, obtain compound 1 (118.1mg), stream part IV (6.4g) is through silicagel column (70g, 5cm × 20cm) methylene dichloride: methyl alcohol (10: 1) purifying 3 times repeatedly, each purifying eluting solvent amount is 1.5L, 60 DEG C of decompression decompression and solvent recoveries, obtain compound 2 (315.6mg), stream part V (5.7g) and stream part VI (1.6g) are respectively through reverse phase silica gel post (100g, 5cm × 15cm) methanol/water (2: 3) purifying 3 times repeatedly, each purifying eluting solvent amount is 1.5L, 60 DEG C of decompression and solvent recoveries, obtain compound 3 (245.3mg) and 4 (29.4mg).
The detected result of the compound 1,2,3,4 obtaining is as follows:
Apigenin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside compounds 1, C
30h
26o
13, yellow powder.HR-ESI-MS(m/z 594.1450[M+H]
+).IR：3356，1701，1654，1606，1506。
1H-NMR(DMSO-d
6，600MHz)δppm：6.77(1H，s，H-3)，6.20(1H，d，J＝1.8Hz，H-6)，6.46(1H，d，J＝1.8Hz，H-8)，7.98(2H，d，J＝8.4Hz，H-2′，H-6′)，7.20(2H，d，J＝8.4Hz，H-3′，H-5′)，5.16(1H，d，J＝7.2Hz，H-1″)，7.03(1H，d，J＝1.8Hz，H-2″′)，6.73(1H，d，J＝8.4Hz，H-5″′)，6.99(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.46(1H，d，J＝15.6Hz，H-7″′)，6.27(1H，d，J＝15.6Hz H-8″′).
13C-NMR(DMSO-d
6，150MHz)δppm：162.9(C-2)，103.7(C-3)，181.6(C-4)，161.3(C-5)，98.8(C-6)，164.2(C-7)，93.9(C-8)，157.2(C-9)，103.7(C-10)，124.0(C-1′)，128.0(C-2′)，116.5(C-3′)，159.9(C-4′)，116.5(C-5′)，128.0(C-6′)，99.6(C-1″)，73.0(C-2″)，73.7(C-3″)，69.7(C-4″)，76.2(C-5″)，63.1(C-6″)，125.3(C-1″′)，114.8(C-2″′)，145.5(C-3″′)，148.4(C-4″′)，115.7(C-5″′)，121.1(C-6″′)，145.3(C-7″′)，113.6(C-8″′)，166.3(C-9″′)。
Luteolin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside compounds 2, C
30h
26o
14, yellow powder.HR-ESI-MS(m/z 611.1382[M+H]
+).IR：3394，1657，1625，1509。
1H-NMR(DMSO-d
6，600MHz)δppm：6.69(1H，s，H-3)，6.20(1H，d，J＝2.4Hz，H-6)，6.44(1H，d，J＝1.8Hz，H-8)，7.49(1H，d，J＝2.4Hz，H-2′)，7.22(1H，d，J＝8.4Hz，H-5′)，7.42(1H，dd，J＝8.4，2.4Hz，H-6′)，4.99(1H，d，J＝7.2Hz，H-1″)，7.05(1H，d，J＝1.8Hz，H-2″′)，6.75(1H，d，J＝8.4Hz，H-5″′)，7.02(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.50(1H，d，J＝15.6Hz，H-7″′)，6.29(1H，d，J＝15.6Hz H-8″′)。
13C-NMR(DMSO-d
6，150MHz)δppm：163.0(C-2)，103.7(C-3)，181.6(C-4)，161.7(C-5)，98.9(C-6)，164.2(C-7)，93.9(C-8)，157.3(C-9)，103.9(C-10)，124.8(C-1′)，113.6(C-2′)，146.9(C-3′)，148.2(C-4′)，115.8(C-5′)，118.3(C-6′)，100.8(C-1″)，73.1(C-2″)，75.7(C-3″)，69.8(C-4″)，73.9(C-5″)，63.1(C-6″)，125.4(C-1″′)，114.9(C-2″′)，145.5(C-3″′)，148.4(C-4″′)，115.8(C-5″′)，121.2(C-6″′)，145.3(C-7″′)，113.7(C-8″′)，166.3(C-9″′)。
Quercetin-4 '-O-β-D-(6 " E-coffee acyl)-glucoside compounds 3, C
30h
26o
15, yellow powder.HR-ESI-MS (m/z 627.1350[M+H]
+).IR：3405，1686，1599，1506。
1H-NMR(DMSO-d
6，600MHz)δppm：6.20(1H，d，J＝2.4Hz，H-6)，6.39(1H，d，J＝1.8Hz，H-8)，7.71(1H，d，J＝1.8Hz，H-2′)，7.23(1H，d，J＝9.0Hz，H-5′)，7.59(1H，dd，J＝9.0，2.4Hz，H-6′)，4.96(1H，d，J＝7.2Hz，H-1″)，6.73(1H，d，J＝8.4Hz，H-5″′)，7.00(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.49(1H，d，J＝15.6Hz，H-7″′)，6.29(1H，d，J＝15.6Hz H-8″′)。
13C-NMR(DMSO-d
6，150MHz)δppm：145.8(C-2)，136.4(C-3)，176.0(C-4)，160.7(C-5)，98.2(C-6)，164.0(C-7)，93.5(C-8)，156.2(C-9)，103.1(C-10)，125.2(C-1′)，115.3(C-2′)，146.3(C-3′)，146.5(C-4′)，115.6(C-5′)，119.4(C-6′)，101.1(C-1″)，73.2(C-2″)，75.7(C-3″)，69.8(C-4″)，73.9(C-5″)，63.2(C-6″)，125.4(C-1″′)，114.9(C-2″′)，145.5(C-3″′)，148.4(C-4″′)，115.8(C-5″′)，121.2(C-6″′)，145.3(C-7″′)，113.7(C-8″′)，166.4(C-9″′)。
Apigenin-7-O-beta-D-(6 " E-coffee acyl)-glucoside compounds 4, C
30h
26o
13, yellow powder.
1H-NMR(DMSO-d
6，600MHz)δppm：6.80(1H，s，H-3)，6.49(1H，d，J＝1.8Hz，H-6)，6.80(1H，d，J＝1.8Hz，H-8)，7.92(2H，d，J＝8.4Hz，H-2′，H-6′)，6.91(2H，d，J＝8.4Hz，H-3′，H-5′)，5.16(1H，d，J＝7.2Hz，H-1″)，6.96(1H，d，J＝1.2Hz，H-2″′)，6.65(1H，d，J＝8.4Hz，H-5″′)，6.84(1H，dd，J＝8.4，1.8Hz，H-6″′)，7.43(1H，d，J＝15.6Hz，H-7″′)，6.23(1H，d，J＝15.6Hz H-8″′)。
13C-NMR(DMSO-d
6，150MHz)δppm：164.2(C-2)，103.0(C-3)，181.8(C-4)，161.1(C-5)，99.3(C-6)，162.6(C-7)，94.7(C-8)，156.8(C-9)，105.3(C-10)，120.8(C-1′)，128.4(C-2′)，115.9(C-3′)，161.2(C-4′)，115.9(C-5′)，128.4(C-6′)，99.5(C-1″)，72.9(C-2″)，76.2(C-3″)，69.8(C-4″)，73.8(C-5″)，63.2(C-6″)，125.3(C-1″′)，114.9(C-2″′)，145.4(C-3″′，148.2(C-4″′)，115.6(C-5″′)，120.9(C-6″′)，145.2(C-7″′)，113.5(C-8″′)，166.3(C-9″′)(Phytochemistry，1995，47：865-874)。
Embodiment 2 classical pathway complement inhibition tests
1 instrument and reagent
Low-temperature and high-speed whizzer (Jouan MR22i), microplate reader (Thermo Labsystems, Well scanMK3), sheep red blood cell (SRBC), anti-sheep red blood cell (SRBC) antibody (sigma company), human serum, veronal-Veronal sodium buffering salt (BBS
2+, pH=7.4, containing 0.5mM Mg
2+with 0.15mM Ca
2+), tri-distilled water, heparin sodium, thermostat water bath.
2 trial drugs
Gnaphalium affine general extractive prepared by embodiment 1 with therefrom separate the acylated flavonoids glycosides compound obtaining
3 experimental techniques
Get human serum, with VBS
2+(barbitol buffer solution, pH=7.4, containing 0.5mM Mg for damping fluid
2+with 0.15mM Ca
2+) dilution be 1: 10, as classical pathway " complement " source.By the antibody of anti-sheep red blood cell with VBS
2+damping fluid dilution be 1: 1000 as hemolysin; By sheep red blood cell (SRBC) VBS
2+damping fluid is configured to 2% sheep red blood cell (SRBC).Acylated flavonoid glycoside compounds 1～4 sample 2mg that respectively prepared by precision weighing embodiment 1, adds VBS
2+damping fluid 1ml dissolves (add 1% methyl-sulphoxide hydrotropy), is made into the sample solution of 2mg/ml, then uses VBS
2+damping fluid two-fold dilution becomes 1mg/ml, 0.5mg/ml, 0.25mg/ml, 0.125mg/ml, 0.0625mg/ml, 0.03125mg/ml, 0.015625mg/ml, 8 different concns of 0.0078125mg/ml." complement " 0.2ml of the sample solution 0.2ml of different concns and 1: 10 is after 37 DEG C of preincubate 10min, add successively the anti-sheep red blood cell antibody of 0.1ml (1: 1000) and 0.1ml 2% sheep red blood cell (SRBC), after hatching 30min, 37 DEG C of water-baths put into low-temperature and high-speed whizzer, at 5000rpm, centrifugal 10min under 4 DEG C of conditions.Get respectively every pipe supernatant 0.2ml on enzyme plate, under microplate reader (Thermo Labsystems, Well scan MK3) 405nm, measure absorbancy.Experiment arranges sample control group simultaneously, and (sample solution of 0.2ml respective concentration adds 0.4ml VBS
2+damping fluid), complement control group is (with 0.2ml VBS
2+damping fluid replaces sample solution) and full haemolysis group (0.1ml 2% sheep red blood cell (SRBC) is dissolved in the water of tri-distillations of 0.5ml).To after the sample sets absorbance deduction respective sample control group absorbance of each concentration, calculate haemolysis inhibiting rate.Using the logarithm of sample concentration as X-axis, haemolysis inhibiting rate is mapped as Y-axis, the fitting a straight line calculation of half inhibitory concentration IC obtaining
50value.
4 experimental results
Using heparin sodium as positive control drug, result shows that acylated flavonoid glycoside 1～4 prepared by above embodiment can suppress classical pathway of complement and activate the cell haemolysis causing, and has significant anticomplementary activity.The results are shown in Table 1
The restraining effect of table 1 compound 1-4 to complement system classical pathway
5 experiment brief summaries
Acylated flavonoid glycoside 1～4 has identical configuration: Flavone aglycone-sugar-aromatic ring side chain, can suppress classical pathway of complement and activate the cell haemolysis causing, have significant anticomplementary activity, the activity of each monomeric compound is all better than the activity of Gnaphalium affine total extract, and this compounds is the good complement inhibitor of a class as seen, can be used for the various diseases that the improper activation of complement causes, and effective concentration is low, toxicity is low, drug safety, wide material sources, and compound 1～3 is new compound; Acylated flavonoid glycoside can directly be digested and assimilated by body as a part for medicinal plant, and the complement inhibitor of developing from natural product also has the advantage that cost is low, is indicating that this compounds has a good application prospect.
Claims (6)
1. acylated flavonoid glycoside compounds, is characterized in that, described compound is:
Apigenin-4'-O-β-D-(6 " E-coffee acyl)-glucoside, following structural formula:
Luteolin-4'-O-β-D-(6 " E-coffee acyl)-glucoside, following structural formula:
; With
Quercetin-4'-O-β-D-(6 " E-coffee acyl)-glucoside, following structural formula:
2. acylated flavonoid glycoside compounds is in the application of preparing in anticomplement medicament; it is characterized in that, described acylated flavonoid glycoside compounds is apigenin-4'-O-β-D-(6 " E-coffee acyl)-glucoside, luteolin-4'-O-β-D-(6 "-E-coffee acyl)-glucoside, Quercetin-4'-O-β-D-(6 " E-coffee acyl)-glucoside or apigenin-7-O-beta-D-(6 "-E-coffee acyl)-glucoside.
3. application according to claim 2, is characterized in that, the pharmaceutical composition that described medicine is made up of as activeconstituents and pharmaceutical carrier apigenin-4'-O-β-D-(6 " E-coffee acyl)-glucoside.
4. application according to claim 2, is characterized in that, the pharmaceutical composition that described medicine is made up of as activeconstituents and pharmaceutical carrier luteolin-4'-O-β-D-(6 " E-coffee acyl)-glucoside.
5. application according to claim 2, is characterized in that, the pharmaceutical composition that described medicine is made up of as activeconstituents and pharmaceutical carrier Quercetin-4'-O-β-D-(6 " E-coffee acyl)-glucoside.
6. application according to claim 2, is characterized in that, the pharmaceutical composition that described medicine is made up of as activeconstituents and pharmaceutical carrier apigenin-7-O-beta-D-(6 " E-coffee acyl)-glucoside.
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