CN104546819A - Use of dicaffeoylquinic acid in treatment of systemic autoimmune disease - Google Patents
Use of dicaffeoylquinic acid in treatment of systemic autoimmune disease Download PDFInfo
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- CN104546819A CN104546819A CN201310468188.8A CN201310468188A CN104546819A CN 104546819 A CN104546819 A CN 104546819A CN 201310468188 A CN201310468188 A CN 201310468188A CN 104546819 A CN104546819 A CN 104546819A
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- dicaffeoylquinic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
Abstract
The invention discloses a use of dicaffeoylquinic acid represented by the formula 1 and a dicaffeoylquinic acid derivative in treatment of systemic autoimmune disease. Preferably, the systemic autoimmune disease is selected from systemic lupus erythematosus, rheumatoid arthritis, systemic sclerosis, Sjogren's syndrome, polymyositis and the like.
Description
Technical field
Invention relates to dicaffeoylquinic acid (Dicaffeoylquinic Acid, the DCQA) novelty teabag in the systemic autoimmune disease such as systemic lupus erythematosus, containing the pharmaceutical composition of dicaffeoylquinic acid.
Background technology
Systemic autoimmune disease refers to, body produces autoantibody to self component generation immunne response, and combines and form antigen antibody complex and be deposited on blood vessel wall etc., causes the many tissues of whole body and organ injury or dysfunction.Comprise systemic lupus erythematosus (sle) (Systemic Lupus Erythematosus, SLE), rheumatoid arthritis (RA), systemic sclerosis (SSc), mouth xerophthalmia scheorma syndrome (SS) etc.
For comparatively serious systemic lupus erythematosus (sle).SLE is a kind of autoimmune disease involving skin and whole body multisystem, and the definite cause of disease is still not clear.Primary disease is common with young women, and China's prevalence is about 70,/10 ten thousand, and the important organs such as confirmed cases more than 50% liver, kidney are impaired.Think that bone-marrow-derived lymphocyte overactivity is bred at present, producing autoantibody and forming immune complex deposit is one of important paathogenic factor of primary disease.Conventional medicine has at present: 1) oxychloroquine; 2) glucocorticoid; 3) immunosuppressant.Though can effective mitigate the disease but still can not effect a radical cure through treatment.And existing medicine also exists certain deficiency, as existing immunosuppressant life-time service can produce bone marrow depression, human body resistance infection reduces, and also usually affects glucose-lipid metabolism to some extent.The target biology medicines such as comparatively safe monoclonal antibody are expensive.Therefore, mechanism of action clear and definite, high-efficiency low-toxicity, cheap new small molecule therapeutic has obvious clinical value.
Summary of the invention
The object of this invention is to provide a kind of medicine for the treatment of autoimmune disease newly, it has excellent curative effect and toxic and side effects is low.
Dicaffeoylquinic acid (DCQA) has entered II clinical trial phase as antiviral drugs.The present inventor finds when carrying out research extensively and profoundly, DCQA has obvious inhibitory action to B lymphocyte proliferation, obviously can reduce the level of anti-dsDNA antibody in systemic lupus erythematosus (sle) syndrome sample mice serum, reduce the deposition of immune complex in nephridial tissue, improve renal pathology damage.The present invention is based on above-mentioned discovery to be accomplished.
If the present invention's first object relates to formula 1(when there is enantiomer, comprise two enantiomer) dicaffeoylquinic acid derivant and the purposes of analog in the medicine for the preparation of transplantation in treating systemic autoimmune disease, described systemic autoimmune diseases is including but not limited to systemic lupus erythematosus (sle), rheumatoid arthritis, systemic sclerosis, sjogren syndrome, polymyositis.
Wherein:
Q
1be a valence link, or CH
2, CHOH, CH
2cH
2, CH
2cHOH, CHOHCH
2, CHCOOH, CH
2cH
2cHOH, CHOHCH
2cH
2, CH
2cHOHCH
2, CH
2cHOHCHOH or CHOHCHOHCH
2;
Q
2and Q
3h can be respectively or be combined and represent CH
2cH
2, CH
2cHOH, CHOHCH
2, CH
2cH
2cHOH, CHOHCH2CH2, CH
2cHOHCH
2, CH
2cHOHCHOH, CHOHCHOHCH
2, CH
2cOH (COOH) CH
2, CH
2cH
2cOH (COOH) CH
2or CH
2cOH (COOH) CH
2cH
2, thus form circulus,
X
1for O, NH, CH
2or CHCOOH;
X
2for O, NH, CH
2or CHCOOH;
Y
1, Y
2, Y
3and Y
4be respectively a valence link, O or NH;
Work as Y
1, Y
2, Y
3when being respectively a valence link with Y4, R
1, R
2, R
3, R
4for CH
2cOOH, CH
2cH
2cOOH or CH
2cH
2cH
2cOOH;
Work as Y
1, Y
2, Y
3and Y
4when being respectively O or NH, R
1, R
2, R
3, R
4for H, CH
3, CH
3cO, CH
3cH
2cO or CH
3cH
2cH
2cO;
Y
5, Y
6, Y
7, Y
8, Y
9, Y
10for H, Cl, Br or I;
Z
1and Z
2for H, COOH, COOM, wherein M represents H, C
1-6alkyl, benzyl, alkali metal or alkaline-earth metal.
When formula 1 exists two enantiomer, comprise two enantiomer.
Preferred dicaffeoylquinic acid derivant is selected from 1; 3-bis--O-caffeoylquinic acids, 1; 4-bis--O-caffeoylquinic acids, 1; 5-bis--O-caffeoylquinic acids, 3; 4-bis--O-caffeoylquinic acids, 3; 5-bis--O-caffeoylquinic acids, 4,5-bis--O-caffeoylquinic acids, their acetyl derivatives and corresponding salt thereof.
Another object of the present invention relates to the pharmaceutical composition containing formula 1 compound, and this pharmaceutical composition has significant inhibitory action to systemic lupus erythematosus (sle) or diseases related.According to the present invention, in this pharmaceutical composition, various pharmaceutical excipient, additive and carrier can be added with.
According to the present invention, pharmaceutical composition of the present invention can be made into the preparation of intestinal or parenterai administration by means known in the art, as tablet, capsule, granule, injection, spray, ointment, nasal drop etc.
Accompanying drawing explanation
Fig. 11,5-dicaffeoylquinic acid reduces SLE syndrome sample kidney of mouse damage figure
A1 normal group animal nephridial tissue; A2 ~ A3 model group animal nephridial tissue diffuse damage, messangial cell hypertrophy, blood capillary are downright bad, diffuse crescent formation, moderate renal tubules pathological changes, renal interstitial monokaryon, lymphocytic infiltration, Renal vascular fibrosis; B1 prednisolone 5mg/Kg group, Renal tissues damage effectively improves; B2 ~ B31,5--dicaffeoylquinic acid 0.22mg/Kg group and 1.1mg/Kg group, Renal tissues damage obviously improves
Fig. 21,5-dicaffeoylquinic acid reduces SLE syndrome sample kidney of mouse IgG immune complex deposit figure
A1 intact animal organizes A2 ~ A3 animal pattern group, nephridial tissue diffuse damage, and IgG is deposited on glomerular mesangium district, renal tubular basement membrane and renal interstitial in a large number and infiltrates inflammatory cell; B1 prednisolone 5mg/Kg group, the slight fluorescence of glomerule, renal tubules; B2 ~ B31,5--dicaffeoylquinic acid 0.22mg/Kg group and 1.1mg/Kg group, IgG immune complex deposit obviously reduces
Detailed description of the invention
The dependent interaction of the dicaffeoylquinic acid by having found is set forth the present invention further below.
Embodiment 1. dicaffeoylquinic acid obviously suppresses the mice spleen B lymphocyte proliferation of In vitro culture
1.1 materials and methods
Cleaning grade BALB/c mouse, male, body weight (19 ± 2) g, purchased from Chinese Academy of Medical Sciences's Experimental Animal Center.LPS, ConA, DMSO, MTT Sigma product.RPMI1640 complete medium is containing penicillin 100U/L, streptomycin 100U/L, glutamine 2mM and 10% hyclone.De-neck puts to death mice, asepticly gets spleen, prepares Pi lymphocyte suspension routinely, with RPMI1640 complete medium adjustment cell 4 × 10
9/ L, 0.1ml/ inoculate in hole 96 orifice plates.Adding LPS(final concentration is 10mg/L), and 1,5-Dicaffeoylquinic acid or 1,3-Dicaffeoylquinic acid (final concentration is 1 × 10
-13– 1 × 10
-6mol/L), the multiple hole of each concentration 6.37 DEG C, 5%CO
2cultivate in incubator.After 44 hours, every hole adds MTT (5g/L) 10 μ L, continues to hatch 4h, inhales gently and abandons supernatant, add acidify isopropyl alcohol 120 μ L, measure 540nm place absorbance by microplate reader after centrifugal.
1.2 result of the test
(1) the 1,5-Dicaffeoylquinic acid mice Pi B lymphocyte proliferation of inducing LPS is inhibited, and 1 × 10
-13-10
-12mol/L and 1 × 10
-6under concentration, inhibitory action significantly (p<0.05, table 1).
Table 11,5-dicaffeoyl quinic acid is on the impact of the mice spleen B-lymphproliferation response that LPS induces
(* p<0.05, p<0.01vs matched group)
(2) the 1,3-Dicaffeoylquinic acid mice Pi B lymphocyte proliferation of inducing LPS is inhibited, and 1 × 10
-12with 1 × 10
-7under mol/L concentration, inhibitory action obviously (p<0.05, table 2).
Table 21,3-dicaffeoylquinic acid is on the impact of the mice spleen B-lymphproliferation response that LPS induces
(* p<0.05, p<0.01vs matched group)
Embodiment 2. dicaffeoylquinic acid obviously reduces systemic lupus erythematosus (sle) syndrome sample mouse antibodies level and the immune complex deposit of active dna induction, improves Renal tissues damage
2.1 materials and methods
BALB/c mouse is put to death in the extraction of splenocyte activation and genomic DNA, and asepticly get spleen, routine prepares splenocyte suspension, and trypan blue counting (survival rate >95%) adjusts cell 2 × 10 with RPMI1640-20% hyclone
9/ L, add Con A and make final concentration be 3mg/L, every bottle of 20mL adds in culture bottle, in 37 DEG C, uprightly cultivates, take out after 48h in 5%CO2 incubator, collected by centrifugation activating cell.Utilize Animal genome DNA a large amount of rapid extraction test kit (the vast Tyke biological gene technology company in Beijing), carry out the preparation of active dna according to test kit operating procedure.Systemic lupus erythematosus (sle) syndrome sample mouse model set up BALB/c mouse, 6wk, female.Mice random packet, often organizes 6, and model group and the immunity of medicine group row, blank group is left intact.Immune programme for children is: Intradermal multi-point injection, and every 2 weeks once, each 0.1mg/0.2mL, amounts to 3 times.DNA dry powder is added normal saline to 2mg/mL by first immunisation, rear injection fully emulsified with equal-volume Freund's complete adjuvant.2nd inoculation DNA and incomplete Freund's adjuvant emulsifying agent; 3rd immunity is DNA suspension.In sensitization process, eye socket is got blood examination and is surveyed anti-ds-DNA antibody level.After administration the 3rd immunity the 8th day starts gastric infusion every day, 0.2mL/10g body weight, totally 15 times.Dosage is respectively 1,5-Dicaffeoylquinic acid 0.22, and 1.1,3.3 and 10mg/Kg body weight; Positive control drug prednisolone acetate 5mg/Kg; Model group and Normal group give 0.5% carboxymethyl cellulose.After last administration, get blood and put to death animal; Get serum test antibodies; Get thymus, spleen, liver weigh calculating organ index; Get kidney and fixedly carry out pathological examination with 4% formalin.Detection 96 hole ELISA Plate (COSTAR) of anti-ds-DNA antibody, every hole adds 100 μ L salmon dsDNA (Sigma, 50mg/L), 4 DEG C of bags are spent the night, PBS-0.5%Tween20 washes plate, 2mg/mL BSA-PBS adsorbs, 100 μ L dilute serums are added after washing plate, use goat anti-mouse IgG-HRP(eBioscience) and enzyme linked immunosorbent assay (ELISA) detection kit (Wuhan doctor's moral), 450nm OD value (microplate reader, Labsystems) is measured according to test kit operational approach.Renal tissue form and immunopathology check that mouse kidney is fixed with 4% formalin, 5 μm of paraffin sections.Conventional slicing treatment, 1) HE dyeing, om observation renal tissue morphological change, blind histological scores: 0=organizes normal; 1=other glomerular minimal change; 2=glomerular mesangial matrixes (< 30%), slight renal tubules pathological changes, slight renal interstitial monokaryon, lymphocytic infiltration; The glomerule performance activeness of 3=certain proportion (< 50%) and hardening, as proliferation of mesangial cells, blood capillary necrosis, microthrombusis, diffuse crescent formation, moderate renal tubules pathological changes, moderate renal interstitial monokaryon, lymphocytic infiltration, Renal vascular fibrosis; 4=> 50% glomerule is got involved, in-severe renal tubules pathological changes and renal interstitial monokaryon, lymphocytic infiltration, Renal vascular fiber-like is downright bad.2) goat anti-mouse IgG-FITC(eBioscience is used) carry out the fluoroscopy of nephridial tissue IgG immune complex, the basic unstressed configuration of blind histological scores: 0=; 1=the slight fluorescence of other glomerule; The light moderate fluorescence of glomerule of 2=some, the light moderate fluorescence of < 25% area renal tubules; The a large amount of glomerule of 3=, 25-50% area renal tubules, invade profit inflammatory cell in intensity fluorescent; 4=glomerule large area hyperfluorescence, > 50% area renal tubules IgG immune complex deposit.
Result of the test
After (1) the 3rd immunity the 7th day, all immune group mice serum anti-ds-DNA antibody levels, all apparently higher than blank group, showed modeling success.
(2) administration is after 15 days, and 0.22mg/Kg body weight dicaffeoylquinic acid administration group mice serum anti-ds-DNA antibody level is respectively 0.270 ± 0.048, compares reduce obviously (p<0.05, table 3) with model group 0.445 ± 0.110.
Table 31,5-dicaffeoylquinic acid is to the effect of SLE syndrome sample mice serum anti-ds-DNA antibody
(* p<0.05, * * p<0.01vs model control group)
(3) HE routine pathology check result shows: model group kidney of mouse diffuse damage, and lupus nephritis occurs obviously (table 4, Figure 1A 2, A3).1,5-Dicaffeoylquinic acid (0.22-10mg/Kg body weight) and prednisolone (5mg/Kg body weight) administration 15 days, all effectively can improve Pathological damage, wherein 1,5-dicaffeoylquinic acid 0.22,1.1mg/Kg body weight group is improved obviously (table 4, Figure 1B 1-3).
Table 41, the impact that 5-dicaffeoylquinic acid damages SLE syndrome sample kidney of mouse
(* p<0.05vs model control group)
(4) nephridial tissue IgG immune complex fluoroscopy result shows, model group kidney of mouse immunopathology scoring compared with normal matched group obviously raises (p<0.05, table 5, figure A2-A3), prednisolone (5mg/Kg body weight) and 1,5-Dicaffeoylquinic acid (0.22,1.1mg/Kg body weight) successive administration 15 days, obviously can reduce nephridial tissue IgG immune complex deposit (p<0.05, table 5, Fig. 2).
Table 51,5-dicaffeoylquinic acid is on the impact of SLE syndrome sample kidney of mouse immune complex deposit
(* p<0.05vs model control group)
Above result shows, 1,5-Dicaffeoylquinic acid obviously can reduce the systemic lupus erythematosus (sle) syndrome sample mice serum anti-ds-DNA antibody level of active dna induction, obviously reduces IgG immune complex at the deposition of nephridial tissue and Renal tissues damage.
In sum, dicaffeoylquinic acid obviously can suppress the mice spleen B lymphocyte proliferation of In vitro culture, the systemic lupus erythematosus (sle) syndrome sample mice serum anti-ds-DNA antibody level of obvious reduction active dna induction, reduce IgG immune complex in the deposition of nephridial tissue, improve lupus nephritis pathology damage.Dicaffeoylquinic acid can be used as a kind of new medicine or drug regimen, for the treatment of the autoimmune diseasees such as systemic lupus erythematosus (sle).
Claims (4)
1. the purposes of dicaffeoylquinic acid derivant in the medicine of preparation system autoimmune disease as shown in Equation 1,
Wherein, Q
1be a valence link, or CH
2, CHOH, CH
2cH
2, CH
2cHOH, CHOHCH
2, CHCOOH, CHOHCH
2cH
2, CH
2cHOHCH
2, CH
2cH
2cHOH, CH
2cHOHCHOH or CHOHCHOHCH
2;
Q
2and Q
3h can be respectively or be combined and represent CH
2cH
2, CH
2cHOH, CHOHCH
2, CH
2cH
2cHOH, CHOHCH
2cH
2, CH
2cHOHCH
2, CH
2cHOHCHOH, CHOHCHOHCH
2, CH
2cOH (COOH) CH
2, CH
2cH
2cOH (COOH) CH
2or CH
2cOH (COOH) CH
2cH
2, thus form circulus,
X
1for O, NH, CH
2or CHCOOH;
X
2for O, NH, CH
2or CHCOOH;
Y
1, Y
2, Y
3and Y
4independently be selected from a valence link, O or NH;
Work as Y
1, Y
2, Y
3and Y
4when being independently selected from a valence link, R
1, R
2, R
3, R
4independently be selected from CH
2cOOH, CH
2cH
2cOOH or CH
2h
2cH
2cOOH;
Work as Y
1, Y
2, Y
3and Y
4when being independently selected from O or NH, R
1, R
2, R
3, R
4independently be selected from H, CH
3, CH
3cO, CH
3cH
2cO or CH
3cH
2cH
2cO;
Y
5, Y
6, Y
7, Y
8, Y
9, Y
10independently be selected from H, Cl, Br or I;
Z
1and Z
2independently be selected from H, COOH, COOM, wherein M represents H, C
1-6alkyl, benzyl, alkali metal or alkaline-earth metal.
2. the purposes of claim 1, when formula 1 exists two enantiomer, comprises two enantiomer.
3. purposes according to claim 1; it is characterized in that; described dicaffeoylquinic acid derivant is selected from 1; 3-bis--O-caffeoylquinic acids, Isosorbide-5-Nitrae-two-O-caffeoylquinic acids, 1,5-bis--O-caffeoylquinic acids, 3; 4-bis--O-caffeoylquinic acids, 3; 5-bis--O-caffeoylquinic acids, 4,5-bis--O-caffeoylquinic acids, their acetyl derivatives and corresponding salt thereof.
4. purposes according to claim 1, is characterized in that, described system autoimmune disease is selected from systemic lupus erythematosus (sle), rheumatoid arthritis, systemic sclerosis, mouth xerophthalmia scheorma syndrome, polymyositis.
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| CN201310468188.8A CN104546819A (en) | 2013-10-09 | 2013-10-09 | Use of dicaffeoylquinic acid in treatment of systemic autoimmune disease |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108003027A (en) * | 2017-12-25 | 2018-05-08 | 北京微医智慧信息技术有限责任公司 | 1-O- caffeoylquinic acids, its derivative, preparation method and its usage |
| WO2019059511A3 (en) * | 2017-09-25 | 2019-05-09 | 제주대학교 산학협력단 | Cosmetic composition containing 3,4-dicaffeoylquinic acid for skin protection against reactive oxygen species, ultraviolet radiation, or fine dust |
| CN110740648A (en) * | 2016-12-30 | 2020-01-31 | 延世大学校产学协力团 | Composition containing 3, 5-dicaffeoylquinic acid or flos Chrysanthemi extract for preventing and treating muscle diseases or improving muscle function |
| CN114848649A (en) * | 2022-04-24 | 2022-08-05 | 黑龙江中医药大学 | Pharmaceutical composition containing caffeoylquinic acid compounds and application thereof in treating rheumatoid arthritis |
| WO2023090781A1 (en) * | 2021-11-22 | 2023-05-25 | 바이오스펙트럼 주식회사 | Composition for preventing and improving skin rosacea comprising isochlorogenic acid or salt thereof as active ingredient |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101222900A (en) * | 2005-05-20 | 2008-07-16 | 杰克·阿比瑟 | Proteasome inhibitors and uses thereof |
| EP2324840A1 (en) * | 2009-11-18 | 2011-05-25 | I.R.B. Istituto Di Ricerche Biotecnologiche S.r.l. | Production of caffeoylquinic acids from plant cell cultures of echinacea angustifolia |
| CN102266318A (en) * | 2011-05-23 | 2011-12-07 | 中国人民解放军第二军医大学 | Application of caffeoylquinic acid and derivatives thereof in preparing anticomplementary medicines |
-
2013
- 2013-10-09 CN CN201310468188.8A patent/CN104546819A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101222900A (en) * | 2005-05-20 | 2008-07-16 | 杰克·阿比瑟 | Proteasome inhibitors and uses thereof |
| EP2324840A1 (en) * | 2009-11-18 | 2011-05-25 | I.R.B. Istituto Di Ricerche Biotecnologiche S.r.l. | Production of caffeoylquinic acids from plant cell cultures of echinacea angustifolia |
| CN102266318A (en) * | 2011-05-23 | 2011-12-07 | 中国人民解放军第二军医大学 | Application of caffeoylquinic acid and derivatives thereof in preparing anticomplementary medicines |
Non-Patent Citations (1)
| Title |
|---|
| 朱乃亮等: "植物中常见咖啡酰奎宁酸类化合物研究进展", 《中华中医药学会中药化学分会第八届学术年会论文集》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110740648A (en) * | 2016-12-30 | 2020-01-31 | 延世大学校产学协力团 | Composition containing 3, 5-dicaffeoylquinic acid or flos Chrysanthemi extract for preventing and treating muscle diseases or improving muscle function |
| US11160840B2 (en) * | 2016-12-30 | 2021-11-02 | Industry-Academic Cooperation Foundation, Yonsei University | Composition for improvement of muscle function containing 3,5-dicaffeoylquinic acid or chrysanthemum extract |
| WO2019059511A3 (en) * | 2017-09-25 | 2019-05-09 | 제주대학교 산학협력단 | Cosmetic composition containing 3,4-dicaffeoylquinic acid for skin protection against reactive oxygen species, ultraviolet radiation, or fine dust |
| CN108003027A (en) * | 2017-12-25 | 2018-05-08 | 北京微医智慧信息技术有限责任公司 | 1-O- caffeoylquinic acids, its derivative, preparation method and its usage |
| WO2019128113A1 (en) * | 2017-12-25 | 2019-07-04 | 北京微医智慧信息技术有限责任公司 | 1-o-caffeoylquinic acid, derivative thereof, preparation method thereof, and application thereof |
| CN108003027B (en) * | 2017-12-25 | 2021-07-06 | 北京微医智慧信息技术有限责任公司 | 1-O-caffeoylquinic acid, its derivative, preparation method and use thereof |
| WO2023090781A1 (en) * | 2021-11-22 | 2023-05-25 | 바이오스펙트럼 주식회사 | Composition for preventing and improving skin rosacea comprising isochlorogenic acid or salt thereof as active ingredient |
| CN114848649A (en) * | 2022-04-24 | 2022-08-05 | 黑龙江中医药大学 | Pharmaceutical composition containing caffeoylquinic acid compounds and application thereof in treating rheumatoid arthritis |
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Application publication date: 20150429 |