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3-O-trans-p-Coumaroyltormentic acid

CAS# 121064-78-6

3-O-trans-p-Coumaroyltormentic acid

Catalog No. BCN4724----Order now to get a substantial discount!

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Chemical structure

3-O-trans-p-Coumaroyltormentic acid

3D structure

Chemical Properties of 3-O-trans-p-Coumaroyltormentic acid

Cas No. 121064-78-6 SDF Download SDF
PubChem ID 14335955 Appearance Powder
Formula C39H54O7 M.Wt 634.86
Type of Compound Triterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-1,11-dihydroxy-10-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-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)OC(=O)C=CC6=CC=C(C=C6)O)O)C)C)C2C1(C)O)C)C(=O)O
Standard InChIKey BZORLJPADUHVJE-QWBBESJSSA-N
Standard InChI InChI=1S/C39H54O7/c1-23-16-19-39(33(43)44)21-20-36(5)26(31(39)38(23,7)45)13-14-29-35(4)22-27(41)32(34(2,3)28(35)17-18-37(29,36)6)46-30(42)15-10-24-8-11-25(40)12-9-24/h8-13,15,23,27-29,31-32,40-41,45H,14,16-22H2,1-7H3,(H,43,44)/b15-10+/t23-,27-,28+,29-,31-,32+,35+,36-,37-,38-,39+/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.
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.
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.

Source of 3-O-trans-p-Coumaroyltormentic acid

The leaves of Eriobotrya japonica calli

Biological Activity of 3-O-trans-p-Coumaroyltormentic acid

Description1. 3-O-(E)-p-coumaroyl tormentic acid induces apoptotic cell death in human leukemia (HL60) via mainly mitochondrial pathway by, at least in part, Topo I inhibition, it may be promising lead compound for developing an effective drug for treatment of leukemia. 2. 3-O-trans-p-coumaroyltormentic acid shows cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) in vitro, the IC50 values of 13.72, 14.29,14.61, 14.04 uM, respectively. 3. 3beta-O-cis-p-Coumaroyltormentic acid, and 3beta-O-trans-p-coumaroyltormentic acid are weakly selective for vancomycin-resistant Enterococcus (VRE) compared with eukaryotic cells, with an MIC of 59.4microg/mL and a 50% inhibitory concentration (IC50) of 72.0microg/mL for monkey kidney epithelial (MA104) cells. 4. A mixture of 3-O-cis-p-coumaroyltormentic acid and 3-O-trans-p-coumaroyltormentic acid shows an inhibitory effect comparable to (-)-epigallocatechin gallate (EGCG) of green tea on the activation of Epstein-Barr virus early antigen (EBV-EA) induced by 12-O-tetradeca--noylphorbol-13-acetate (TPA).
TargetsAntifection | Caspase

3-O-trans-p-Coumaroyltormentic acid Dilution Calculator

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3-O-trans-p-Coumaroyltormentic acid Molarity Calculator

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Preparing Stock Solutions of 3-O-trans-p-Coumaroyltormentic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.5752 mL 7.8758 mL 15.7515 mL 31.503 mL 39.3788 mL
5 mM 0.315 mL 1.5752 mL 3.1503 mL 6.3006 mL 7.8758 mL
10 mM 0.1575 mL 0.7876 mL 1.5752 mL 3.1503 mL 3.9379 mL
50 mM 0.0315 mL 0.1575 mL 0.315 mL 0.6301 mL 0.7876 mL
100 mM 0.0158 mL 0.0788 mL 0.1575 mL 0.315 mL 0.3938 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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References on 3-O-trans-p-Coumaroyltormentic acid

Cytotoxic triterpenes from a Chinese medicine, Goreishi.[Pubmed:2752475]

Chem Pharm Bull (Tokyo). 1989 Mar;37(3):648-51.

Bioactivity-guided fractionation of the methanol extract of Goreishi (the feces of Trogopterus xanthipes Milne-Edwards) afforded one new and three known cytotoxic triterpenes, namely, 3-O-cis-p-coumaroyltormentic acid, pomolic acid, 2 alpha-hydroxyursolic acid, and jacoumaric acid. In the course of this investigation, six additional compounds having no cytotoxic activity were isolated, namely, maslinic acid, 3-O-trans-p-coumaroylmaslinic acid, ursolic acid, tormentic acid, euscaphic acid, and a new triterpene, 3-O-trans-p-Coumaroyltormentic acid. The structures of the new compounds were established on the basis of X-nucleus-proton correlation with fixed evolution time (XCORFE) and other spectroscopic evidence.

3-O-(E)-p-coumaroyl tormentic acid from Eriobotrya japonica leaves induces caspase-dependent apoptotic cell death in human leukemia cell line.[Pubmed:21372421]

Chem Pharm Bull (Tokyo). 2011;59(3):378-81.

Eleven triterpene acids, 1-11, isolated from the leaves of Eriobotrya japonica, were evaluated for inhibition of DNA topoisomerase (Topo) I and cytotoxicity against human leukemia (HL60) and melanoma cell lines (CRL1579). Among the compounds tested, four compounds, delta-oleanolic acid (4), ursolic acid (5), 3-O-(E)-p-coumaroyl tormentic acid (8), and betulinic acid (10), exhibited potent Topo I inhibitory activity (IC(50) 20.3-36.5 microM) and cytotoxicity against HL60 (EC(50) 5.0-8.1 microM). Upon assessing the apoptosis-inducing activity in HL60 cells, compound 8 exhibited induction of apoptosis detected by the observation of DNA fragmentation and membrane phospholipid exposure in flow cytometry. Western blot analysis showed that compound 8 markedly reduced the levels of procaspases-3 and 9, while being increased the levels of cleaved caspases-3 and 9. On the other hand, compound 8 exerted almost no influence on the expression of caspase-8. In addition, compound 8 increased significantly Bax/Bcl-2 ratio and activated caspase-2. These results suggested that compound 8 induced apoptotic cell death in HL60 via mainly mitochondrial pathway by, at least in part, Topo I inhibition. Therefore, compound 8 may be promising lead compound for developing an effective drug for treatment of leukemia.

Production of bioactive triterpenes by Eriobotrya japonica calli.[Pubmed:11830140]

Phytochemistry. 2002 Feb;59(3):315-23.

Callus tissue cultures induced from an axenic leaf of Eriobotrya japonica (Rosaceae) produced triterpenes in large amounts (ca. 50 mg/g dry wt). Nine triterpenes were characterized as ursolic acid, oleanolic acid, 2alpha-hydoxyursolic acid, maslinic acid, tormentic acid, 2alpha, 19alpha-dihydroxy-3-oxo-urs-12-en-28-oic acid, hyptadienic acid and a mixture of 3-O-cis-p-coumaroyltormentic acid and 3-O-trans-p-Coumaroyltormentic acid. The triterpene composition in the callus tissues was noticeably different from that in intact leaves. The contents of tormentic acid with antidiabetic action, and 2alpha, 19alpha-dihydroxy-3-oxo-urs-12-en-28-oic acid with anti-HIV activity, were much larger than those in the intact leaves. All of the triterpenes isolated from the callus tissues showed an inhibitory effect comparable to (-)-epigallocatechin gallate (EGCG) of green tea on the activation of Epstein-Barr virus early antigen (EBV-EA) induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). 2alpha, 19alpha-Dihydroxy-3-oxo-urs-12-en-28-oic acid was the most potent inhibitor among them and caused a significant delay of two-stage carcinogenesis on mouse skin.

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