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Thonningianin A

CAS# 271579-11-4

Thonningianin A

2D Structure

Catalog No. BCN2774----Order now to get a substantial discount!

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Quality Control of Thonningianin A

3D structure

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Thonningianin A

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Chemical Properties of Thonningianin A

Cas No. 271579-11-4 SDF Download SDF
PubChem ID 10328286 Appearance Powder
Formula C42H34O21 M.Wt 874.7
Type of Compound Chalcones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES C1C2C(C(C(C(O2)OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC=CC=C4)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6C7=C(C(=C(C=C7C(=O)O1)O)O)O)O)O)O
Standard InChIKey XQVKQEFQGYTUAR-VHBRHXFYSA-N
Standard InChI InChI=1S/C42H34O21/c43-20(7-6-15-4-2-1-3-5-15)30-21(44)10-17(11-22(30)45)60-42-36(55)38(63-39(56)16-8-23(46)31(50)24(47)9-16)37-27(61-42)14-59-40(57)18-12-25(48)32(51)34(53)28(18)29-19(41(58)62-37)13-26(49)33(52)35(29)54/h1-5,8-13,27,36-38,42,44-55H,6-7,14H2/t27-,36-,37-,38-,42-/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 Thonningianin A

The herbs of Penthorum chinense Pursh

Biological Activity of Thonningianin A

DescriptionThonningianin A represents a new potent glutathione S-transferase in vitro inhibitor. Thonningianin A has anti-cancer and antioxidant properties, involves radical scavenging, anti-superoxide formation and metal chelation.
TargetsCaspase | CDK | ERK | NF-kB | p38MAPK | NADPH-oxidase
In vitro

Effects of thonningianin A in natural foods on apoptosis and cell cycle arrest of HepG-2 human hepatocellular carcinoma cells.[Pubmed: 26119846]

Food Funct. 2015 Aug;6(8):2588-97.


METHODS AND RESULTS:
The anti-cancer activities of Thonningianin A on the HepG-2 human hepatocellular carcinoma cell line were evaluated by MTT assay, flow cytometry, quantitative real-time PCR and western blotting. Results showed that Thonningianin A effectively inhibited the proliferation of HepG-2 cells by inducing apoptosis, as evidenced by increase in the sub-G1 cell population, DNA fragmentation, and increase in the content of reactive oxygen species. Activation of caspase-9 and the subsequent activation of caspase-3 indicated that Thonningianin A-induced apoptosis is caspase-dependent. Thonningianin A also disrupted the mitochondrial membrane potential (Δψm) and down-regulated the Bcl-xL mRNA expression in HepG-2 cells. Thonningianin A induced cell cycle arrest by changing the cyclin D1 and CDK4 mRNA expression levels. Moreover, western blotting showed that Thonningianin A significantly down-regulated the NF-kappa-B cell survival pathway, along with up-regulation of the expression level of phosphorylated P38 and down-regulation of the expression level of phosphorylated ERK.
CONCLUSIONS:
The anti-cancer activity of Thonningianin A was confirmed by the characteristic patterns of DNA fragmentation and cell cycle arrest, suggesting that Th A is an effective antitumor ingredient in natural plant foods, and is worthy of further study.

Antioxidant properties of Thonningianin A, isolated from the African medicinal herb, Thonningia sanguinea.[Pubmed: 12007576]

Biochem Pharmacol. 2002 May 1;63(9):1725-37.

The antioxidant properties of Thonningianin A (Th A), an ellagitannin, isolated from the methanolic extract of the African medicinal herb, Thonningia sanguinea were studied using the NADPH and Fe2+/ascorbate-induced lipid peroxidation (LPO), electron spin resonance spectrometer and the deoxyribose assay.
METHODS AND RESULTS:
Thonningianin A at 10 microM inhibited both the NADPH and Fe2+/ascorbate-induced LPO in rat liver microsomes by 60% without inhibitory effects on cytochrome P450 activity. Thonningianin A was similar to the synthetic antioxidant, tannic acid, as an inhibitor of both the NADPH and Fe2+/ascorbate-induced LPO but potent than gallic acid, vitamin C and vitamin E. While Thonningianin A poorly scavenged the hydroxyl radical generated by the Fenton reaction it dose-dependently scavenged 1,1-diphenyl-2-picrylhydrazyl, superoxide anion and peroxyl radicals with IC50 of 7.5, 10 and 30 microM, respectively. Furthermore, Thonningianin A showed inhibitory effects on the activity of xanthine oxidase with an IC50 of 30 microM. In the deoxyribose assay both T. sanguinea and its methanolic component Thonningianin A showed only site-specific (Fe3+ + H2O2) but not non-site-specific (Fe3+ + EDTA + H2O2) hydroxyl radical scavenging suggesting chelating ability for iron ions.
CONCLUSIONS:
Spectroscopic studies showed that Thonningianin A enhanced absorbance in the visible region in the presence of Fe2+ ions. These results indicate that the antioxidant properties of Thonningianin A involve radical scavenging, anti-superoxide formation and metal chelation.

Protocol of Thonningianin A

Kinase Assay

Inhibition of glutathione S-transferases by thonningianin A, isolated from the African medicinal herb, Thonningia sanguinea, in vitro.[Pubmed: 15234070]

Food Chem Toxicol. 2004 Sep;42(9):1401-8.

There is evidence that increased expression of glutathione S-transferase (EC: 2.5.1.18, GST) is involved in resistance of tumor cells against chemotherapeutic agents. In this study we investigated the inhibitory effects of Thonningianin A (Th A), a novel antioxidant isolated from the medicinal herb, Thonningia sanguinea on uncharacterized rat liver GST and human GST P1-1.
METHODS AND RESULTS:
Using 1-chloro-2,4-dinitrobenzene (CDNB) as substrate, rat liver cytosolic GST activity was inhibited by Thonningianin A in a concentration dependent manner with 50% inhibition concentration (IC50) of 1.1 microM. When Thonningianin A was compared with known potent GST inhibitors the order of inhibition was tannic acid>cibacron blue>hematin>Th A>ethacrynic acid with CDNB as substrate. Thonningianin A also exhibited non-competitive inhibition towards both CDNB and glutathione. Furthermore, using 1,2-dichloro-4-nitrobenzene, ethacrynic acid and 1,2-epoxy-3-(p-nitrophenoxy) propane as substrates Thonningianin A at 1.0 microM inhibited cytosolic GST by 2%, 12% and 36% respectively. Human GST P1-1 was also inhibited by Thonningianin A with an IC50 of 3.6 microM.
CONCLUSIONS:
While Thonningianin A showed competitive inhibition towards CDNB it exhibited non-competitive inhibition towards GSH of the human GST P1-1. These results suggest that Thonningianin A represents a new potent GST in vitro inhibitor.

Thonningianin A Dilution Calculator

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Preparing Stock Solutions of Thonningianin A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.1432 mL 5.7162 mL 11.4325 mL 22.865 mL 28.5812 mL
5 mM 0.2286 mL 1.1432 mL 2.2865 mL 4.573 mL 5.7162 mL
10 mM 0.1143 mL 0.5716 mL 1.1432 mL 2.2865 mL 2.8581 mL
50 mM 0.0229 mL 0.1143 mL 0.2286 mL 0.4573 mL 0.5716 mL
100 mM 0.0114 mL 0.0572 mL 0.1143 mL 0.2286 mL 0.2858 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 Thonningianin A

Effects of thonningianin A in natural foods on apoptosis and cell cycle arrest of HepG-2 human hepatocellular carcinoma cells.[Pubmed:26119846]

Food Funct. 2015 Aug;6(8):2588-97.

The anti-cancer activities of Thonningianin A on the HepG-2 human hepatocellular carcinoma cell line were evaluated by MTT assay, flow cytometry, quantitative real-time PCR and western blotting. Results showed that Thonningianin A effectively inhibited the proliferation of HepG-2 cells by inducing apoptosis, as evidenced by increase in the sub-G1 cell population, DNA fragmentation, and increase in the content of reactive oxygen species. Activation of caspase-9 and the subsequent activation of caspase-3 indicated that Thonningianin A-induced apoptosis is caspase-dependent. Thonningianin A also disrupted the mitochondrial membrane potential (Deltapsim) and down-regulated the Bcl-xL mRNA expression in HepG-2 cells. Thonningianin A induced cell cycle arrest by changing the cyclin D1 and CDK4 mRNA expression levels. Moreover, western blotting showed that Thonningianin A significantly down-regulated the NF-kappa-B cell survival pathway, along with up-regulation of the expression level of phosphorylated P38 and down-regulation of the expression level of phosphorylated ERK. The anti-cancer activity of Thonningianin A was confirmed by the characteristic patterns of DNA fragmentation and cell cycle arrest, suggesting that Th A is an effective antitumor ingredient in natural plant foods, and is worthy of further study.

Antioxidant properties of Thonningianin A, isolated from the African medicinal herb, Thonningia sanguinea.[Pubmed:12007576]

Biochem Pharmacol. 2002 May 1;63(9):1725-37.

The antioxidant properties of Thonningianin A (Th A), an ellagitannin, isolated from the methanolic extract of the African medicinal herb, Thonningia sanguinea were studied using the NADPH and Fe2+/ascorbate-induced lipid peroxidation (LPO), electron spin resonance spectrometer and the deoxyribose assay. Th A at 10 microM inhibited both the NADPH and Fe2+/ascorbate-induced LPO in rat liver microsomes by 60% without inhibitory effects on cytochrome P450 activity. Th A was similar to the synthetic antioxidant, tannic acid, as an inhibitor of both the NADPH and Fe2+/ascorbate-induced LPO but potent than gallic acid, vitamin C and vitamin E. While Th A poorly scavenged the hydroxyl radical generated by the Fenton reaction it dose-dependently scavenged 1,1-diphenyl-2-picrylhydrazyl, superoxide anion and peroxyl radicals with IC50 of 7.5, 10 and 30 microM, respectively. Furthermore, Th A showed inhibitory effects on the activity of xanthine oxidase with an IC50 of 30 microM. In the deoxyribose assay both T. sanguinea and its methanolic component Th A showed only site-specific (Fe3+ + H2O2) but not non-site-specific (Fe3+ + EDTA + H2O2) hydroxyl radical scavenging suggesting chelating ability for iron ions. Spectroscopic studies showed that Th A enhanced absorbance in the visible region in the presence of Fe2+ ions. These results indicate that the antioxidant properties of Th A involve radical scavenging, anti-superoxide formation and metal chelation.

Inhibition of glutathione S-transferases by thonningianin A, isolated from the African medicinal herb, Thonningia sanguinea, in vitro.[Pubmed:15234070]

Food Chem Toxicol. 2004 Sep;42(9):1401-8.

There is evidence that increased expression of glutathione S-transferase (EC: 2.5.1.18, GST) is involved in resistance of tumor cells against chemotherapeutic agents. In this study we investigated the inhibitory effects of Thonningianin A (Th A), a novel antioxidant isolated from the medicinal herb, Thonningia sanguinea on uncharacterized rat liver GST and human GST P1-1. Using 1-chloro-2,4-dinitrobenzene (CDNB) as substrate, rat liver cytosolic GST activity was inhibited by Th A in a concentration dependent manner with 50% inhibition concentration (IC50) of 1.1 microM. When Th A was compared with known potent GST inhibitors the order of inhibition was tannic acid>cibacron blue>hematin>Th A>ethacrynic acid with CDNB as substrate. Th A also exhibited non-competitive inhibition towards both CDNB and glutathione. Furthermore, using 1,2-dichloro-4-nitrobenzene, ethacrynic acid and 1,2-epoxy-3-(p-nitrophenoxy) propane as substrates Th A at 1.0 microM inhibited cytosolic GST by 2%, 12% and 36% respectively. Human GST P1-1 was also inhibited by Th A with an IC50 of 3.6 microM. While Th A showed competitive inhibition towards CDNB it exhibited non-competitive inhibition towards GSH of the human GST P1-1. These results suggest that Th A represents a new potent GST in vitro inhibitor.

Description

Thonningianin A, an ellagitannin, is isolated from the methanolic extract of the African medicinal herb, Thonningia sanguinea. The antioxidant properties of Th A involve radical scavenging, anti-superoxide formation and metal chelation. Anti-cancer activities.

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