Tormentic acidCAS# 13850-16-3 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 13850-16-3 | SDF | Download SDF |
| PubChem ID | 73193 | Appearance | White powder |
| Formula | C30H48O5 | M.Wt | 488.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Synonyms | 2α,19α-Dihydroxyursolic acid; Tormentolic acid | ||
| Solubility | Soluble in DMF, methanol and pyridine; insoluble in water | ||
| Chemical Name | (1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid | ||
| SMILES | CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C)O)O)C)C)C2C1(C)O)C)C(=O)O | ||
| Standard InChIKey | OXVUXGFZHDKYLS-BLIWDXROSA-N | ||
| Standard InChI | InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23+,26+,27-,28-,29-,30+/m1/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. Tormentic acid has anti-allodynic action, can inhibit markedly the neuropathic allodynia induced by partial ligation of the sciatic nerve. 2. Tormentic acid has anti-inflammatory activity, it potently inhibits the production of nitric oxide (NO) in RAW 264.7 cells, also suppresses the LPS-stimulated degradation and phosphorylation of inhibitor of kappa B-α (IκB-α), suggests that the anti-inflammatory activity of TA is associated with the down-regulation of iNOS, COX-2, and TNF-α through the negative regulation of the NF-κB pathway in RAW 264.7 cells. 3. Tormentic acid has anticancer, anti-atherogenic properties and minimal toxicity in vivo, it also can reduce vascular smooth muscle cell proliferation and survival. 4. Tormentic acid has protective effect against lipopolysaccharide/D-galactosamine induced fulminant hepatic failure in mice. |
| Targets | NO | HO-1 | GLUT | NOS | NF-kB | Bcl-2/Bax | Caspase | COX | IL Receptor | PGE | PPAR | TNF-α | AMPK |
Tormentic acid Dilution Calculator
Tormentic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0462 mL | 10.2312 mL | 20.4625 mL | 40.9249 mL | 51.1561 mL |
| 5 mM | 0.4092 mL | 2.0462 mL | 4.0925 mL | 8.185 mL | 10.2312 mL |
| 10 mM | 0.2046 mL | 1.0231 mL | 2.0462 mL | 4.0925 mL | 5.1156 mL |
| 50 mM | 0.0409 mL | 0.2046 mL | 0.4092 mL | 0.8185 mL | 1.0231 mL |
| 100 mM | 0.0205 mL | 0.1023 mL | 0.2046 mL | 0.4092 mL | 0.5116 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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Tormentic acid, a major component of suspension cells of Eriobotrya japonica, suppresses high-fat diet-induced diabetes and hyperlipidemia by glucose transporter 4 and AMP-activated protein kinase phosphorylation.[Pubmed:25317836]
J Agric Food Chem. 2014 Nov 5;62(44):10717-26.
This study was designed to evaluate the effects and mechanism of Tormentic acid (PTA) on diabetes and dyslipidemia in high-fat (HF)-fed mice. Feeding C57BL/6J mice with a HF diet for 12 weeks induced type 2 diabetes and hyperlipidemia. During the last 4 weeks, the mice were given orally PTA (at two dosages) or rosiglitazone (Rosi) or water. In this study, the HF diet increased glucose, triglyceride, insulin, and leptin levels, whereas PTA effectively prevented these phenomena and ameliorated insulin resistance. PTA reduced visceral fat mass and hepatic triacylglycerol contents; moreover, PTA significantly decreased both the area of adipocytes and ballooning degeneration of hepatocytes. PTA caused increased skeletal muscular AMP-activated protein kinase (AMPK) phosphorylation and Akt phosphorylation and glucose transporter 4 (GLUT4) proteins, but reduced the hepatic expressions of phosphenolpyruvate carboxykinase (PEPCK) and glucose-6-phosphatase (G6 Pase) genes. PTA enhanced skeletal muscular Akt phosphorylation and increased insulin sensitivity. PTA also enhanced phospho-AMPK in the liver. Therefore, it is possible that the activation of AMPK by PTA results in decreasing hepatic glucose production while increasing skeletal muscular GLUT4 contents, thus contributing to attenuating the diabetic state. Moreover, PTA exhibits an antihyperlipidemic effect by down-regulations of the hepatic sterol regulatory element binding protein-1c (SREBP-1c) and apolipoprotein C-III (apo C-III) and an increased peroxisome proliferator activated receptor (PPAR)-alpha expression, thus resulting in decreases in blood triglycerides. These findings demonstrated that PTA was effective for the treatment of diabetes and hyperlipidemia in HF-fed mice.
Tormentic acid reduces inflammation in BV-2 microglia by activating the liver X receptor alpha.[Pubmed:25497374]
Neuroscience. 2015 Feb 26;287:9-14.
Tormentic acid (TA) has been reported to have anticancer, anti-inflammatory and anti-atherogenic properties. However, the effects of TA on neuroinflammation have not been reported. In this study, we investigated whether TA inhibited lipopolysaccharide (LPS)-induced inflammatory response in BV2 microglia cells. BV2 microglia cells were treated with TA for 1h before exposure to LPS. The expression of inducible nitric oxide synthase (iNOS), Cyclooxygenase-2 (COX-2), Nuclear factor kappaB (NF-kappaB) and liver X receptor alpha (LXRalpha) was detected by western blotting. The expression of cytokines Tumor necrosis factor-alpha (TNF-alpha) and interleukin 1beta (IL-1beta) was detected by enzyme-linked immunosorbent assays (ELISA). Results showed that TA inhibited nitric oxide (NO), prostaglandin E2 (PGE2) production by inhibiting iNOS and COX-2 expression. TA also inhibited LPS-induced inflammatory cytokines TNF-alpha and IL-1beta expression. Furthermore, TA could activate LXRalpha and inhibit LPS-induced NF-kappaB activation. Knowdown of LXRalpha reversed the anti-inflammatory effects of TA. In conclusion, our results indicate that TA exerts an anti-inflammatory effect on LPS-stimulated BV2 microglia cells by activating LXRalpha.
Antiproliferative activities on renal, prostate and melanoma cancer cell lines of Sarcopoterium spinosum aerial parts and its major constituent tormentic acid.[Pubmed:23157592]
Anticancer Agents Med Chem. 2013 Jun;13(5):768-76.
The search for improved cytotoxic agents continues to be an important line in the discovery of modern anticancer drugs. Sarcopoterium spinosum (L.) Spach is mentioned in ethnobotanical surveys as a medicinal plant used for the treatment of cancer. The aim of this study is to investigate and to compare the aerial parts of S. spinosum collected in Italy and Lebanon for their chemical composition and their antiproliferative activity against ACHN, C32, A375, MCF-7, LNCaP and HeLa human cancer cell lines using SRB assay. The main constituent Tormentic acid was isolated by MPLC and characterized by spectroscopic techniques (NMR, MS). Non polar compounds were analyzed by GC and GC-MS. S. spinosum showed an interesting antiproliferative activity against ACHN and C32 cell lines with IC(50) values of 2.4 and 2.7 mug/ml for S. spinosum from Italy and Lebanon, respectively. Remarkable results were obtained also against A375 and LNCaP cell lines. The cytotoxicity against ACHN cell line could be partially attributed to Tormentic acid that demonstrated a higher cytotoxicity than the positive control vinblastine. Close association between the radical scavenging activity (evaluated by DPPH and ABTS assay) and cytotoxicity was also demonstrated. This investigation demonstrated the potential cytotoxic activity of S. spinosum taking into account also that none of the tested extracts, fractions and isolated compound affected the proliferation of normal cell line 142BR. Tormentic acid, the major constituent isolated from S. spinosum, play an important role in the cytotoxicity exhibited by the extract.
Anti-allodynic action of the tormentic acid, a triterpene isolated from plant, against neuropathic and inflammatory persistent pain in mice.[Pubmed:12398905]
Eur J Pharmacol. 2002 Oct 25;453(2-3):203-8.
Experiments were designed to address whether the pentacyclic triterpene Tormentic acid isolated from the stem bark of the plant Vochysia divergens exerts oral anti-allodynic properties in two models of chronic pain in mice: neuropathic pain caused by partial ligation of the sciatic nerve and inflammatory pain produced by intraplantar injection of Complete Freund's Adjuvant. Oral administration of Tormentic acid (30 mg/kg) twice a day for several consecutive days produced time-dependent and pronounced anti-allodynia effect in both ispsilateral and contralateral paws after plantar injection of Complete Freund's Adjuvant. The inhibition observed was 82+/-9% and 100+/-11%, respectively. Interestingly, Tormentic acid did not inhibit paw oedema formation following Complete Freund's Adjuvant plantar injection. Tormentic acid (30 mg/kg, p.o.) and gabapentin (70 mg/kg, p.o.), given twice a day, inhibited markedly the neuropathic allodynia induced by partial ligation of the sciatic nerve, with inhibition of 91+/-19% and 71+/-16%, respectively. The anti-allodynic action of Tormentic acid was not associated with impairment of the motor activity of the animals. Together, the present results indicate that Tormentic acid or its derivatives might be of potential interest in the development of new clinically relevant drugs for the management of persistent neuropathic and inflammatory allodynia.
Protective effect of tormentic acid from Potentilla chinensis against lipopolysaccharide/D-galactosamine induced fulminant hepatic failure in mice.[Pubmed:24560903]
Int Immunopharmacol. 2014 Apr;19(2):365-72.
A compound was isolated from Potentilla chinensis, and it was identified as Tormentic acid (TA) based on its physicochemical properties and spectral data. The hepatoprotective effect of TA was evaluated using an acute liver failure model induced by lipopolysaccharide (LPS)/D-galactosamine (D-GalN). The results revealed that TA significantly prevented LPS/D-GalN-induced fulminant hepatic failure, as evidenced by the decrease in serum aminotransferase and total bilirubin activities and the attenuation of histopathological changes. TA alleviated the pro-inflammatory cytokines including TNF-alpha and NO/iNOS by inhibiting nuclear factor-kappaB (NF-kappaB) activity. Moreover, TA strongly inhibited lipid peroxidation, recruited the anti-oxidative defense system, and increased HO-1 activity. In addition, TA significantly attenuated increases in TUNEL-positive hepatocytes through decreasing the levels of cytochrome c, as well as caspases-3, 8 and 9, while augmenting the expression of Bcl-2. In conclusion, TA protects hepatocytes against LPS/D-GalN-induced injury by blocking NF-kappaB signaling pathway for anti-inflammatory response and attenuating hepatocellular apoptosis. Consequently, TA is a potential agent for preventing acute liver injury and may be a major bioactive ingredient of Potentilla chinensis.
