Echinocystic acidCAS# 510-30-5 |
Quality Control & MSDS
3D structure
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| Cas No. | 510-30-5 | SDF | Download SDF |
| PubChem ID | 73309 | Appearance | White powder |
| Formula | C30H48O4 | M.Wt | 472.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 100 mg/mL (211.55 mM) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid | ||
| SMILES | CC1(CCC2(C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)O)C)C(=O)O)C | ||
| Standard InChIKey | YKOPWPOFWMYZJZ-PRIAQAIDSA-N | ||
| Standard InChI | InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)19(16-25)18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,6)29(18,7)17-23(30)32/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21+,22-,23+,27-,28+,29+,30+/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 | Echinocystic acid has cardioprotective, hypolipidemic, anti-tumor, anti-inflammatory and antioxidant effects, it displays substantial inhibitory activity on HCV entry.Orally administered lancemaside A may be metabolized to echinocystic acid, which may be absorbed into the blood and ameliorate memory and learning deficits by inhibiting AChE activity and inducing BDNF and p-CREB expressions.Orally administered lancemaside A may be metabolized to echinocystic acid, which may be absorbed into the blood and ameliorate memory and learning deficits by inhibiting AChE activity and inducing BDNF and p-CREB expressions. |
| Targets | COX | NOS | TNF-α | IL Receptor | LDL | Akt | NF-kB | IkB | p65 | NO | TLR | PGE | Bcl-2/Bax | Caspase | ROS | HMG-CoA reductase | HCV | IKK |
| In vitro | Echinocystic acid isolated from Eclipta prostrata suppresses lipopolysaccharide-induced iNOS, TNF-α, and IL-6 expressions via NF-κB inactivation in RAW 264.7 macrophages.[Pubmed: 23877917]Planta Med. 2013 Aug;79(12):1031-7In this study, we aimed to identify the compounds in Eclipta prostrata responsible for its anti-inflammatory effects using an in vitro bioassay. Echinocystic acid, isolated from Gleditsia sinensis fruit, protects endothelial progenitor cells from damage caused by oxLDL via the Akt/eNOS pathway.[Pubmed: 25086379 ]Life Sci. 2014 Oct 2;114(2):62-9.Our previous studies revealed that Echinocystic acid (EA) showed obvious attenuation of atherosclerosis in rabbits fed a high-fat diet. However, the underlying mechanisms remain to be elucidated. Considering the importance of endothelial progenitor cells (EPCs) in atherosclerosis, we hypothesise that EPCs may be one of the targets for the anti-atherosclerotic potential of EA.
|
| In vivo | Protective effects of echinocystic acid isolated from Gleditsia sinensis Lam. against acute myocardial ischemia.[Pubmed: 19573579 ]Fitoterapia. 2010 Jan;81(1):8-10.Echinocystic acid (EA), a pentacyclic triterpene, was isolated and identified from the fruits of Gleditsia sinensis Lam. |
| Kinase Assay | Deciphering molecular mechanism underlying hypolipidemic activity of echinocystic Acid.[Pubmed: 24669228 ]Echinocystic acid induces apoptosis in HL-60 cells through mitochondria-mediated death pathway.[Pubmed: 15246558 ]Cancer Lett. 2004 Aug 20;212(1):21-32.Echinocystic acid (EA) is a natural triterpone enriched in various herbs and used for medicinal purpose in many Asian countries. Evid Based Complement Alternat Med. 2014;2014:823154.Our previous study showed that a triterpene mixture, consisting of Echinocystic acid (EA) and oleanolic acid (OA) at a ratio of 4 : 1, dose-dependently ameliorated the hyperlipidemia and atherosclerosis in rabbits fed with high fat/high cholesterol diets. |
| Animal Research | Osteoprotective Effect of Echinocystic Acid, a Triterpone Component from Eclipta prostrata, in Ovariectomy-Induced Osteoporotic Rats.[Pubmed: 26317835 ]Lancemaside A isolated from Codonopsis lanceolata and its metabolite echinocystic acid ameliorate scopolamine-induced memory and learning deficits in mice.[Pubmed: 23079229 ]Phytomedicine. 2012 Dec 15;20(1):84-8.The rhizome of Codonopsis lanceolata (family Campanulaceae), which contains lancemaside A as a main constituent, has been used as herbal medicine to treat inflammation, insomnia, and hypomnesia. PLoS One. 2015 Aug 28;10(8):e0136572.Echinocystic acid (EA) is a natural triterpone enriched in various herbs and has been used for medicinal purposes in China. |
| Structure Identification | Eur J Med Chem. 2013 Jun;64:160-8.Elucidation of the pharmacophore of echinocystic acid, a new lead for blocking HCV entry.[Pubmed: 23644199 ]
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Echinocystic acid Dilution Calculator
Echinocystic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.1155 mL | 10.5775 mL | 21.1551 mL | 42.3101 mL | 52.8877 mL |
| 5 mM | 0.4231 mL | 2.1155 mL | 4.231 mL | 8.462 mL | 10.5775 mL |
| 10 mM | 0.2116 mL | 1.0578 mL | 2.1155 mL | 4.231 mL | 5.2888 mL |
| 50 mM | 0.0423 mL | 0.2116 mL | 0.4231 mL | 0.8462 mL | 1.0578 mL |
| 100 mM | 0.0212 mL | 0.1058 mL | 0.2116 mL | 0.4231 mL | 0.5289 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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Echinocystic acid a pentacyclic triterpene isolated from the fruits of Gleditsia sinensis Lam, has potent antioxidant, anti-inflammatory and anti-tumor properties. In vitro: Echinocystic acid (EA) inhibit the formation of osteoclast. EA inhibit RANKL-induced NF-κB activation and ERK phosphorylation in BMMs. [1] EA inhibit IL-1β-induced inflammation in chondrocytes. [2] In vivo: Echinocystic acid reduces reserpine-induced pain/depression dyad in mice. [3]
References:
[1]. Yang JH et al. Echinocystic acid inhibits RANKL-induced osteoclastogenesis by regulating NF-κB and ERK signaling pathways. Biochem Biophys Res Commun. 2016 Sep 2;477(4):673-7.
[2]. Ma Z et al. Echinocystic Acid Inhibits IL-1β-Induced COX-2 and iNOS Expression in Human Osteoarthritis Chondrocytes. Inflammation. 2016 Apr;39(2):543-9.
[3]. Li S et al. Echinocystic acid reduces reserpine-induced pain/depression dyad in mice. Metab Brain Dis. 2016 Apr;31(2):455-63.
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Echinocystic acid, isolated from Gleditsia sinensis fruit, protects endothelial progenitor cells from damage caused by oxLDL via the Akt/eNOS pathway.[Pubmed:25086379]
Life Sci. 2014 Oct 2;114(2):62-9.
AIMS: Our previous studies revealed that Echinocystic acid (EA) showed obvious attenuation of atherosclerosis in rabbits fed a high-fat diet. However, the underlying mechanisms remain to be elucidated. Considering the importance of endothelial progenitor cells (EPCs) in atherosclerosis, we hypothesise that EPCs may be one of the targets for the anti-atherosclerotic potential of EA. MAIN METHODS: After in vitro cultivation, EPCs were exposed to 100 mug/mL of oxidised low-density lipoprotein (oxLDL) and incubated with or without EA (5 and 20 muM) for 48 h. An additional two groups of EPCs (oxLDL+20 muM EA) were pre-treated with either wortmannin, an inhibitor of the phosphoinositide 3-kinase (PI3K) pathway, or nitro-l-arginine methyl ester (l-NAME), an endothelial nitric oxide synthase (eNOS)-specific inhibitor. Assessment of EPC apoptosis, adhesion, migration, and nitric oxide (NO) release was performed using terminal deoxynucleotidyl transferase-mediated dUTP nick-end labelling (TUNEL) staining, cell counting, caspase-3 activity assay, transwell chamber assay, and Griess reagent, respectively. The protein expression of protein kinase B (Akt) and eNOS was detected using Western blot. KEY FINDINGS: Treatment of EPCs with oxLDL induced significant apoptosis and impaired adhesion, migration, and NO production. The deleterious effects of oxLDL on EPCs were attenuated by EA. However, when EPCs were pre-treated with wortmannin or l-NAME, the effects of EA were abrogated. Additionally, oxLDL significantly down-regulated eNOS protein expression as well as repression of eNOS and Akt phosphorylation. SIGNIFICANCE: The inhibitory effect of oxLDL on Akt/eNOS phosphorylation was attenuated by EA. Taken together, the results indicate that EA protects EPCs from damage caused by oxLDL via the Akt/eNOS pathway.
Protective effects of echinocystic acid isolated from Gleditsia sinensis Lam. against acute myocardial ischemia.[Pubmed:19573579]
Fitoterapia. 2010 Jan;81(1):8-10.
Echinocystic acid (EA), a pentacyclic triterpene, was isolated and identified from the fruits of Gleditsia sinensis Lam. The protective effects of EA were evaluated in rat models with acute myocardial ischemia induced by isoproterenol and vasopressin. In the electrocardiogram of anesthetized rats, EA prevented the ST-segment depression induced by isoproterenol or vasopressin in a dose-dependently manner. Furthermore, the mRNA expression of Bcl-2 was analyzed by RT-PCR. EA shows an elevation of Bcl-2 mRNA level in infarcted tissue induced by isoproterenol in rats. These results demonstrated for the first time EA has a cardioprotective effect and may be a natural drug.
Echinocystic acid isolated from Eclipta prostrata suppresses lipopolysaccharide-induced iNOS, TNF-alpha, and IL-6 expressions via NF-kappaB inactivation in RAW 264.7 macrophages.[Pubmed:23877917]
Planta Med. 2013 Aug;79(12):1031-7.
In this study, we aimed to identify the compounds in Eclipta prostrata responsible for its anti-inflammatory effects using an in vitro bioassay. Three triterpenoids, eclalbasaponin I, eclalbasaponin II, and Echinocystic acid, were isolated from an EtOAc fraction of the 70 % EtOH extract of E. prostrata by activity-guided fractionation based on the inhibition of nitric oxide release from lipopolysaccharide-induced RAW 264.7 macrophages. Of these three triterpenoids, Echinocystic acid inhibited lipopolysaccharide-induced production of nitric oxide and cytokines such as tumor necrosis factor-alpha and interleukin-6. Consistent with these observations, Echinocystic acid concentration-dependently inhibited lipopolysaccharide-induced inducible nitric oxide synthase expression at the protein level and inducible nitric oxide synthase, tumor necrosis factor-alpha, and interleukin-6 expression at the mRNA level, and inhibited lipopolysaccharide-induced iNOS promoter binding activity. In addition, Echinocystic acid suppressed the lipopolysaccharide-induced transcriptional activity of nuclear factor-kappaB by blocking the nuclear translocation of p65.
Osteoprotective Effect of Echinocystic Acid, a Triterpone Component from Eclipta prostrata, in Ovariectomy-Induced Osteoporotic Rats.[Pubmed:26317835]
PLoS One. 2015 Aug 28;10(8):e0136572.
Echinocystic acid (EA) is a natural triterpone enriched in various herbs and has been used for medicinal purposes in China. In the present study, we systematically examined the effects of EA on ovariectomy-induced osteoporosis in rats for the first time. Three-month-old female ovariectomy (OVX) Sprague-Dawley rats were used to evaluate the osteoprotective effect of EA. Results showed that administration of EA (5 or 15 mg/kg/day) for 12 weeks prevented lower levels of maximum stress and Young's modulus of femur induced by OVX. EA also recovered bone metabolic biomarkers levels in OVX rats, including osteocalcin, alkaline phosphatese, deoxypyridinoline, and urinary calcium and phosphorus. EA (5 and 15 mg/kg/day) could prevent the alteration of total bone mineral density in the femur caused by OVX. However, only high dose (15 mg/kg/day) of EA significantly improved trabecular architecture, as evidenced by higher levels of bone volume/tissue volume, trabecula number, and trabecula thickness, and lower levels of trabecula separation and structure model index compared with OVX rats. In addition, EA treatment decresed the serum levels of IL-1beta and TNF-alpha in OVX rats. In conclusion, EA could prevent reduction of bone mass and strength and improve the cancellous bone structure and biochemical properties in OVX rats. Hence, EA may serve as a new candidate or a leading compound for anti-osteoporosis.
Deciphering molecular mechanism underlying hypolipidemic activity of echinocystic Acid.[Pubmed:24669228]
Evid Based Complement Alternat Med. 2014;2014:823154.
Our previous study showed that a triterpene mixture, consisting of Echinocystic acid (EA) and oleanolic acid (OA) at a ratio of 4 : 1, dose-dependently ameliorated the hyperlipidemia and atherosclerosis in rabbits fed with high fat/high cholesterol diets. This study was aimed at exploring the mechanisms underlying antihyperlipidemic effect of EA. Molecular docking simulation of EA was performed using Molegro Virtual Docker (version: 4.3.0) to investigate the potential targets related to lipid metabolism. Based on the molecular docking information, isotope labeling method or spectrophotometry was applied to examine the effect of EA on the activity of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase, acyl-CoA:cholesterol acyltransferase (ACAT), and diacylglycerol acyltransferase (DGAT) in rat liver microsomes. Our results revealed a strong affinity of EA towards ACAT and DGAT in molecular docking analysis, while low binding affinity existed between EA and HMG-CoA reductase as well as between EA and cholesteryl ester transfer protein. Consistent with the results of molecular docking, in vitro enzyme activity assays showed that EA inhibited ACAT and DGAT, with IC50 values of 103 and 139 mu M, respectively, and exhibited no significant effect on HMG-CoA reductase activity. The present findings suggest that EA may exert hypolipidemic effect by inhibiting the activity of ACAT and DGAT.
Echinocystic acid induces apoptosis in HL-60 cells through mitochondria-mediated death pathway.[Pubmed:15246558]
Cancer Lett. 2004 Aug 20;212(1):21-32.
Echinocystic acid (EA) is a natural triterpone enriched in various herbs and used for medicinal purpose in many Asian countries. In the present study, we reported that EA can induce apoptosis in human promyelocytic leukemia cells (HL-60), as characterized by DNA fragmentation, poly (ADP) ribose polymerase cleavage. The efficacious induction of apoptosis was observed at 100 microM for 6 h. Further molecular analysis showed that EA induced the cleavage of Bid protein, the loss of mitochondrial membrane potential (DeltaPsim) cytochrome c release from mitochondria into cytosol, and activation of caspase-3, -8 and -9. However, EA did not generate reactive oxygen species (ROS), and antioxidants including N-acetyl cysteine and catalase could not block EA-induced apoptosis in the HL-60 cells. These data suggest that EA induces apoptosis in HL-60 cells through ROS-independent mitochondrial dysfunction pathway.
Elucidation of the pharmacophore of echinocystic acid, a new lead for blocking HCV entry.[Pubmed:23644199]
Eur J Med Chem. 2013 Jun;64:160-8.
To elucidate the pharmacophore of Echinocystic acid (EA), an oleanane-type triterpene displaying substantial inhibitory activity on HCV entry, two microbial strains, Rhizopus chinensis CICC 3043 and Alternaria alternata AS 3.4578, were utilized to modify the chemical structure of EA. Eight new metabolites with regio- and stereo-selective introduction of hydroxyl and lactone groups at various inert carbon positions were obtained. The anti-HCV entry activity of the metabolites 2-13, along with their parental compound EA and other analogs 14-15, were evaluated. Most of the metabolites showed no improvement but detrimental effect on potency except compound 5 and 6, which showed similar and even a litter higher anti-HCV entry activity than that of EA. The results demonstrated that ring A, B, C and the left side of ring E of EA are highly conserved, while ring D and the right side of ring E of EA are flexible. Introduction of a hydroxyl group at C-16 enhanced the triterpene potency. Further analysis indicated that the hemolytic effect of EA disappeared upon such modifications.
Lancemaside A isolated from Codonopsis lanceolata and its metabolite echinocystic acid ameliorate scopolamine-induced memory and learning deficits in mice.[Pubmed:23079229]
Phytomedicine. 2012 Dec 15;20(1):84-8.
The rhizome of Codonopsis lanceolata (family Campanulaceae), which contains lancemaside A as a main constituent, has been used as herbal medicine to treat inflammation, insomnia, and hypomnesia. Lancemaside A and Echinocystic acid, which is its metabolite by intestinal microflora, potently inhibited acetylcholinesterase activity in a dose-dependent manner, with IC(5)(0) value 13.6 muM and 12.2 muM, respectively. Its inhibitory potency is comparable with that of donepezil (IC(5)(0)=10.9 muM). Lancemaside A and Echinocystic acid significantly reversed scopolamine-induced memory and learning deficits on passive avoidance task. Lancemaside A orally administered 5h before treatment with scopolamine reversed scopolamine-induced memory and learning deficits more potently than one orally administered 1h before. Echinocystic acid more potently reversed it than lancemaside A. Lancemaside A and Echinocystic acid significantly reversed scopolamine-induced memory and learning deficits on the Y-maze and Morris water maze tasks. Lancemaside A and Echinocystic acid also increased the expression of brain-derived neurotrophic factor (BDNF) and phosphorylated cAMP response element binding protein (p-CREB). Based on these findings, orally administered lancemaside A may be metabolized to Echinocystic acid, which may be absorbed into the blood and ameliorate memory and learning deficits by inhibiting AChE activity and inducing BDNF and p-CREB expressions.
