Clematichinenoside ARCAS# 761425-93-8 |
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| Cas No. | 761425-93-8 | SDF | Download SDF |
| PubChem ID | 11434888 | Appearance | Powder |
| Formula | C82H134O43 | M.Wt | 1807.93 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4S,5R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate | ||
| SMILES | CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3C(OC(C(C3O)O)OC4COC(C(C4O)O)OC5C(C(OC(C5O)OC6C(C(COC6OC7CCC8(C(C7(C)C)CCC9(C8CC=C1C9(CCC2(C1CC(CC2)(C)C)C(=O)OC1C(C(C(C(O1)COC1C(C(C(C(O1)CO)OC1C(C(C(C(O1)C)O)O)O)O)O)O)O)O)C)C)C)O)O)C)O)CO)O)O)O)O)O)O | ||
| Standard InChIKey | JFLCHMJGYAFQIU-AOXNNHMFSA-N | ||
| Standard InChI | InChI=1S/C82H134O43/c1-28-42(86)49(93)56(100)67(112-28)109-25-36-46(90)51(95)58(102)72(118-36)122-64-35(23-84)116-71(61(105)54(64)98)117-38-27-111-69(55(99)48(38)92)123-65-44(88)30(3)114-74(62(65)106)124-66-45(89)33(85)24-108-75(66)120-41-14-15-79(8)39(78(41,6)7)13-16-81(10)40(79)12-11-31-32-21-77(4,5)17-19-82(32,20-18-80(31,81)9)76(107)125-73-59(103)52(96)47(91)37(119-73)26-110-68-60(104)53(97)63(34(22-83)115-68)121-70-57(101)50(94)43(87)29(2)113-70/h11,28-30,32-75,83-106H,12-27H2,1-10H3/t28-,29-,30-,32-,33-,34+,35+,36+,37+,38+,39-,40+,41-,42-,43-,44-,45-,46+,47+,48+,49+,50+,51-,52-,53+,54+,55+,56+,57+,58+,59+,60+,61+,62+,63+,64+,65+,66+,67+,68+,69-,70-,71-,72-,73-,74-,75-,79-,80+,81+,82-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Clematichinenoside AR exerts anti-inflammatory and immunosuppressive properties. 2. Clematichinenoside AR has antioxidant and anti-inflammatory cardioprotection effects against MI/R injury, it protects H9c2 cardiomyocytes against H/R-induced apoptosis through mitochondrial-mediated apoptotic signaling pathway. 3. Clematichinenoside AR could be used as an effective neuroprotective agent to protect against ischemic stroke after cerebral I/R injury through regulating both ERK1/2 and cPKC mediated p90RSK/CREB apoptotic pathways. 4. Clematichinenoside AR has anti-arthritic effects on PI3K/Akt signaling pathway and TNF-α associated with collagen-induced arthritis. |
| Targets | TGF-β/Smad | HIF | IL Receptor | TNF-α | gp120/CD4 | PI3K | Akt |
Clematichinenoside AR Dilution Calculator
Clematichinenoside AR Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 0.5531 mL | 2.7656 mL | 5.5312 mL | 11.0624 mL | 13.828 mL |
| 5 mM | 0.1106 mL | 0.5531 mL | 1.1062 mL | 2.2125 mL | 2.7656 mL |
| 10 mM | 0.0553 mL | 0.2766 mL | 0.5531 mL | 1.1062 mL | 1.3828 mL |
| 50 mM | 0.0111 mL | 0.0553 mL | 0.1106 mL | 0.2212 mL | 0.2766 mL |
| 100 mM | 0.0055 mL | 0.0277 mL | 0.0553 mL | 0.1106 mL | 0.1383 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Clematichinenoside AR induces immunosuppression involving Treg cells in Peyers patches of rats with adjuvant induced arthritis.[Pubmed:25063305]
J Ethnopharmacol. 2014 Sep 11;155(2):1306-14.
ETHNOPHARMACOLOGICAL RELEVANCE: Clematichinenoside AR (AR) has been defined as a major active ingredient of triterpenoid saponins extracted from Clematidis Radix et Rhizoma, which is a traditional Chinese herbal medicine that has long been used in the treatment of rheumatoid arthritis (RA). To further explore the mechanism of AR in the treatment of RA, we investigated whether its immunomodulatory effects are related to Treg-mediated suppression derived from Peyers patches (PPs) in adjuvant induced arthritis (AIA) rat model. MATERIALS AND METHODS: AR (8, 16, 32 mg/kg) was orally administered daily from Day 18 to Day 31 after immunization. The effect of AR on AIA rats was evaluated by hind paw swelling and histopathological examination. Percentages of CD4(+)CD25(+)Foxp3(+) T regulatory cells were determined by flow cytometry. Levels of IL-10, TGF-beta1, IL-17A and TNF-alpha were measured by ELISA. Expressions of Foxp3 and RORgamma in synovium were detected using immunohistochemical analysis. RESULTS: AR treatment significantly reduced paw swelling of AIA rats, and histopathological analysis confirmed it could suppress severity of established arthritis. AR treatment upregulated the percentages of CD4(+)CD25(+)Foxp3(+) Treg cells among CD4+ T cells in PPs lymphocytes, and increased the levels of IL-10 and TGF-beta1 secreted from ConA-activated PPs lymphocytes, whereas decreased the levels of IL-17 A and TNF-alpha. Similar tendency of circulating CD4(+)CD25(+)Foxp3(+) Treg cells percentages and serum cytokine levels were observed. Moreover, AR decreased the expression levels of Foxp3 and RORgamma in joint synovial membrane. CONCLUSIONS: In conclusion, these results suggested AR has a potent protective effect on the progression of AIA, probably by augmenting CD4(+)CD25(+)Foxp3(+) Treg cells in PPs to induce immunosuppression, and modulating the balance between Treg cells and Th17 cells systemically. These findings may help to develop AR as a potent immunosuppressive agent for the treatment of RA.
Succinate/NLRP3 Inflammasome Induces Synovial Fibroblast Activation: Therapeutical Effects of Clematichinenoside AR on Arthritis.[Pubmed:28003810]
Front Immunol. 2016 Dec 7;7:532.
Clematichinenoside AR (C-AR) is a triterpene saponin isolated from the root of Clematis manshurica Rupr., which is a herbal medicine used in traditional Chinese medicine for the treatment of arthritis. C-AR exerts anti-inflammatory and immunosuppressive properties, but little is known about its action in the suppression of fibroblast activation. Low oxygen tension and transforming growth factor-beta (TGF-beta1) induction in the synovium contribute to fibrosis in arthritis. This study was designed to investigate the effect of C-AR on synovial fibrosis from the aspects of hypoxic TGF-beta1 and hypoxia-inducible transcription factor-1alpha (HIF-1alpha) induction. In the synovium of rheumatoid arthritis (RA) rats, hypoxic TGF-beta1 induction increased succinate accumulation due to the reversal of succinate dehydrogenase (SDH) activation and induced NLRP3 inflammasome activation in a manner dependent on HIF-1alpha induction. In response to NLRP3 inflammasome activation, the released IL-1beta further increased TGF-beta1 induction, suggesting the forward cycle between inflammation and fibrosis in myofibroblast activation. In the synovium of RA rats, C-AR inhibited hypoxic TGF-beta1 induction and suppressed succinate-associated NLRP3 inflammasome activation by inhibiting SDH activity, and thereby prevented myofibroblast activation by blocking the cross-talk between inflammation and fibrosis. Taken together, these results showed that succinate worked as a metabolic signaling, linking inflammation with fibrosis through NLRP3 inflammasome activation. These findings suggested that synovial succinate accumulation and HIF-1alpha induction might be therapeutical targets for the prevention of fibrosis in arthritis.
Anti-arthritic effects of clematichinenoside (AR-6) on PI3K/Akt signaling pathway and TNF-alpha associated with collagen-induced arthritis.[Pubmed:22994412]
Pharm Biol. 2013 Jan;51(1):13-22.
CONTEXT: Clematichinenoside (AR-6) is a triterpene saponin from an anti-arthritic herbal formula Wei-Ling-Xian in Chinese, which is an herbal medicine derived from the dried root and rhizome of Clematis chinensis Osbeck, C. hexapetala Pall., or C. manshurica Rupr. (Ranunculaceae). OBJECTIVE: To investigate the modulating effect and explored the potential mechanism of AR-6 in rheumatoid arthritis (RA), using collagen-induced arthritis (CIA) in a rat model. MATERIALS AND METHODS: CIA was evaluated by measuring body weight, paw swelling and organ index. Expression of TNF-alpha, PI3K and p-Akt in synovium tissue was measured by immunohistochemistry. Furthermore, expression of TNF-alpha mRNA, PI3K mRNA and p-Akt mRNA was measured with RT-PCR. RESULTS: The intragastric administration of AR-6 (32, 16 and 8 mg/kg), especially the high dose level of 32 mg/kg, significantly suppressed the swelling of hind paws of CIA rats (p < 0.01) and inhibited their body weight loss (p < 0.01). Based on histopathological observation, all AR-6 groups showed great amelioration compared with model group. Moreover, AR-6 significantly reduced the production of TNF-alpha, PI3K and p-Akt expression by immunohistochemistry (p < 0.01), and decreased TNF-alpha mRNA, PI3K mRNA and p-Akt mRNA in CIA rat synovium (p < 0.01). DISCUSSION: Our study indicates the mechanism of AR-6 is associated with PI3K/Akt signaling pathway and TNF-alpha. CONCLUSIONS: Such characteristics relating to AR-6 curing chronic inflammation of CIA, may be effectively applied to the therapeutic potential in patients with inactive RA.
Identification of the metabolites of anti-inflammatory compound clematichinenoside AR in rat intestinal microflora.[Pubmed:23852993]
Biomed Chromatogr. 2013 Dec;27(12):1767-74.
Clematichinenoside AR (C-AR), a pentacyclic triterpenoid saponin with anti-inflammatory and anti-rheumatoid activities, is the main active component of the traditional Chinese medicine Clematidis Radix et Rhizoma. However, its poor oral absorption indicated that not only the parent compound C-AR itself, but also its metabolites could be responsible for the pharmacological effects in rats. The present study aimed to investigate the metabolism of C-AR in rat intestinal microflora, where C-AR was extensively metabolized. C-AR was incubated with the content of the large intestine. The culture solution was collected at different time points and analyzed for the metabolites of C-AR. Eight metabolites were identified by liquid chromatography/quadrupole time-of-flight mass spectrometry. M1, M2 and M5 were the major metabolites. In addition, it was proposed that deglycosylation was the only pathway contributing to the biotransformation of C-AR in rat intestinal microflora.
