Uncarinic acid ECAS# 277751-61-8 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 277751-61-8 | SDF | Download SDF |
| PubChem ID | 10746421 | Appearance | Powder |
| Formula | C39H54O6 | M.Wt | 618.84 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-hydroxy-6a-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid | ||
| SMILES | CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)COC(=O)C=CC6=CC=C(C=C6)O)C(=O)O)C | ||
| Standard InChIKey | ZPBONBNZOMMCQS-PBGJSAINSA-N | ||
| Standard InChI | InChI=1S/C39H54O6/c1-34(2)19-20-38(33(43)44)21-22-39(24-45-32(42)14-9-25-7-10-26(40)11-8-25)27(28(38)23-34)12-13-30-36(5)17-16-31(41)35(3,4)29(36)15-18-37(30,39)6/h7-12,14,28-31,40-41H,13,15-24H2,1-6H3,(H,43,44)/b14-9+/t28-,29-,30+,31-,36-,37+,38-,39-/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. Uncarinic acid E shows moderate cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and Bt549) (IC50 < 20.0 uM). 2. Uncarinic acid E induces apoptosis in HepG2 cells via accumulation of p53, alters the Bax/Bcl-2 ratio, and activates caspases, resulting in cytochrome c release from the mitochondria. 3. Uncarinic acid E shows dose-dependent inhibitory activities against PLCgamma1 in vitro with the IC(50) value of 9.5-44.6 microM and inhibits the proliferation of human cancer cells with the IC(50) value of 0.5-6.5 microg/mL. 4. A mixture of uncarinic acid E and 27-O-p-(E)-coumaroyloxyursolic acid exhibits antiplasmodial activity, with the IC50 value of 2.9 microg/ml. |
| Targets | Bcl-2/Bax | Caspase | p53 | MEK | PI3K | Antifection |
Uncarinic acid E Dilution Calculator
Uncarinic acid E Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.6159 mL | 8.0796 mL | 16.1593 mL | 32.3185 mL | 40.3982 mL |
| 5 mM | 0.3232 mL | 1.6159 mL | 3.2319 mL | 6.4637 mL | 8.0796 mL |
| 10 mM | 0.1616 mL | 0.808 mL | 1.6159 mL | 3.2319 mL | 4.0398 mL |
| 50 mM | 0.0323 mL | 0.1616 mL | 0.3232 mL | 0.6464 mL | 0.808 mL |
| 100 mM | 0.0162 mL | 0.0808 mL | 0.1616 mL | 0.3232 mL | 0.404 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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Inhibition of phospholipase cgamma1 and cancer cell proliferation by triterpene esters from Uncaria rhynchophylla.[Pubmed:10869194]
J Nat Prod. 2000 Jun;63(6):753-6.
Investigation of the hooks of Uncaria rhynchophylla resulted in isolation of six phospholipase Cgamma1 (PLCgamma1) inhibitors (1-6). The structures of these compounds were elucidated as pentacyclic triterpene esters by spectroscopic and chemical analysis. Three of them, namely uncarinic acids C (1), D (2), and E (3), are newly reported as natural products. All the compounds showed dose-dependent inhibitory activities against PLCgamma1 in vitro with IC(50) values of 9.5-44.6 microM and inhibited the proliferation of human cancer cells with IC(50) values of 0.5-6.5 microg/mL.
The course of uncarinic acid E-induced apoptosis of HepG2 cells from damage to DNA and p53 activation to mitochondrial release of cytochrome c.[Pubmed:16880619]
Biol Pharm Bull. 2006 Aug;29(8):1639-44.
Uncarinic acid E, an active component isolated from Gelsemium elegans BENTH, has been reported to exhibit antitumor effects, but little is known about its molecular mechanisms of action. In this study, the growth-inhibitory activity of Uncarinic acid E for HepG2 cells is in time- and dose-dependent manner. HepG2 cells treated with Uncarinic acid E exhibited several typical characteristics of apoptosis through photomicroscopical observation, DNA agarose gel electrophoresis. The inhibitory effect of Uncarinic acid E on HepG2 cells was partially reversed by the inhibitors of pan-caspase, caspase-3 and caspase-6. The protein expression ratio of Bcl-xL/Bax and Bcl-2/Bax was down-regulated and Uncarinic acid E-induced apoptosis involves the initial phase mediated by the balance among Bcl-xL, Bcl-2 and Bax proteins, resulting in cytochrome c release from the mitochondria. Uncarinic acid E significantly increased the expression of p53 proteins indicates that p53 plays a pivotal role in the initiation phase of Uncarinic acid E-induced HepG2 cell apoptosis. The phoshatidylinositol 3-kinase (PI3-K) family inhibitor wortmanin and the MEK inhibitor (PD98059) rescued the viability loss induced by Uncarinic acid E through the expression of p53. Taken together, Uncarinic acid E induces apoptosis in HepG2 cells via accumulation of p53, alters the Bax/Bcl-2 ratio, and activates caspases, resulting in cytochrome c release from the mitochondria.
Cytotoxic Triterpenoids from the Barks of Betula platyphylla var. japonica.[Pubmed:28052515]
Chem Biodivers. 2017 Apr;14(4).
Phytochemical investigation on the barks of Betula platyphylla var. japonica (Betulaceae) was carried out, resulting in the isolation and identification of three new triterpenoids, 27-O-cis-caffeoylcylicodiscic acid (1), 27-O-cis-feruloylcylicodiscic acid (2), and 27-O-cis-caffeoylmyricerol (3), along with six known triterpenoids, obtusilinin (4), winchic acid (5), 27-O-trans-caffeoylcylicodiscic acid (6), Uncarinic acid E (7), myriceric acid B (8), and 3-O-trans-caffeoyloleanolic acid (9). The structures of the new compounds were elucidated by extensive spectroscopic methods, including 1D- and 2D-NMR, and HR-ESI-MS. All of the isolated compounds were evaluated for cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and Bt549). Compounds 2, 6, 8, and 9 exhibited potent cytotoxicity against all of the tumor cells tested (IC50 < 10.0 mum), while compounds 3, 4, 5, and 7 showed moderate cytotoxicity against all of the tumor cells tested (IC50 < 20.0 mum).
Antiplasmodial triterpenes from twigs of Gardenia saxatilis.[Pubmed:12963155]
J Ethnopharmacol. 2003 Oct;88(2-3):275-7.
Ten triterpenes (1-10) were isolated and identified from the twigs of Gardenia saxatilis (Rubiaceae) and were subjected to antiplasmodial evaluation against the parasite Plasmodium falciparum. The first six compounds, lupenone (1), lupeol (2), betulinic acid (3), oleanolic acid (4), ursolic acid (5), and winchic acid (27-O-feruloyloxybetulinic acid) (6) were inactive in the assay. The other four compounds, messagenic acid A (7) and messagenic acid B (8), the 27-O-p-(Z)- and 27-O-p-(E)-coumarate esters of betulinic acid, and a mixture of Uncarinic acid E (27-O-p-(E)-coumaroyloxyoleanolic acid) (9) and 27-O-p-(E)-coumaroyloxyursolic acid (10) exhibited antiplasmodial activity, with the IC50 values of 1.5, 3.8 and 2.9 microg/ml, respectively. The results indicated that the p-coumarate moieties at the 27-position, both the cis and trans isomers, contributed to antiplasmodial activity. Introduction of a methoxyl group to the 3-position of the p-coumarate moiety to give a ferulate moiety resulted in loss of activity.
