Chebulinic acid

Names

[ Name ]:
Chebulinic acid

[Synonym ]:
7,11-Methanopyrano[4,3,2-kl][2,5,8]benzotrioxacyclotridecin-4-acetic acid, 2,3,3a,4,5,7,8,10,11,13-decahydro-3,15,16-trihydroxy-2,5,13-trioxo-10,17-bis[(3,4,5-trihydroxybenzoyl)oxy]-8-[[(3,4,5-trihydroxybenzoyl)oxy]methyl]-, (3S,3aS,4S,7R,8R,10S,11R,17S)-
Eutannin
[(4R,5S,7R,8R,11S,12S,13S,21S)-13,17,18-Trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-{[(3,4,5-trihydroxybenzoyl)oxy]methyl}-3,6,9,15-tetraoxatetracyclo[10.7.1.1.0]hen icosa-1(20),16,18-trien-11-yl]acetic acid

Biological Activity

[Description]:

Chebulinic acid is a potent natural inhibitor of M. tuberculosis DNA gyrase, also can inhibit SMAD-3 phosphorylation, inhibit H+ K+-ATPase activity.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump

Signaling Pathways >> Stem Cell/Wnt >> TGF-beta/Smad

Signaling Pathways >> TGF-beta/Smad >> TGF-beta/Smad

Research Areas >> Infection

Natural Products >> Phenols

[Target]

target: M. tuberculosis DNA gyrase[1], SMAD-3 phosphorylation[2], H+ K+-ATPase activity.[3]IC50: 65.01 μg/ml ( H+ K+-ATPase ) [3]

[In Vitro]

In vitro: binding of Chebulinic acid causes displacement of catalytic Tyr129 away from its target DNA-phosphate molecule. [1] Chebulinic acid reduce the expression and activity of MMP-2 at an ED50 value of 100 μM. EMT (Epithelial to Mesenchymal Transition) is found to be induced in ARPE-19 cells, through SMAD-3 phosphorylation and it is inhibited by CA. [2] chebulinic acid significantly inhibited H+ K+-ATPase activity in vitrowith IC50 of 65.01 μg/ml. [3]

[References]

[1]. Patel K et al. Identification of chebulinic acid as potent natural inhibitor of M. tuberculosis DNA gyrase and molecular insights into its binding mode of action. Comput Biol Chem. 2015 Dec;59 Pt A:37-47.

[2]. Sivasankar S et al. Aqueous and alcoholic extracts of Triphala and their active compounds chebulagic acid and chebulinic acidprevented epithelial to mesenchymal transition in retinal pigment epithelial cells, by inhibiting SMAD-3 phosphorylation. PLoS One. 2015 Mar 20

[3]. Mishra V et al. Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers. Phytomedicine. 2013 Apr 15;20(6):506-11.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
1460.0±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₁H₃₂O₂₇

[ Molecular Weight ]:
956.677

[ Flash Point ]:
437.2±27.8 °C

[ Exact Mass ]:
956.113098

[ PSA ]:
447.09000

[ LogP ]:
4.14

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.837

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers.

Phytomedicine 20(6) , 506-11, (2013)

In continuation of our drug discovery program on Indian medicinal plants, the gastro protective mechanism of chebulinic acid isolated from Terminalia chebula fruit was investigated. Chebulinic acid wa...

Chemical changes during fermentation of Abhayarishta and its standardization by HPLC-DAD.

Nat. Prod. Commun. 5(4) , 575-9, (2010)

Abhayarishta is an Ayurvedic formulation prepared traditionally by the fermentation of the decoction of Terminalia chebula (pericarp), Vitis vinifera (fruits), Embelia ribes (fruits) and Madhuca indic...

A new phenolic compound, 4-dehydrochebulic acid-1,6-dimethyl ester from Sapium insigne leaves.

J. Nat. Med. 64(2) , 191-3, (2010)

A new phenolic compound, 4-dehydrochebulic acid-1,6-dimethyl ester (2) was isolated from the leaves of Sapium insigne (Royle) Benth. ex Hook. fil. (Euphorbiaceae) along with three known compounds gall...