Chebulagic acid

Names

[ Name ]:
Chebulagic acid

[Synonym ]:
Chebulagic acid
[(4R,5S,7R,25S,26R,29S,30S,31S)-13,14,15,18,19,20,31,35,36-Nonahydroxy-2,10,23,28,32-pentaoxo-5-[(3,4,5-trihydroxybenzoyl)oxy]-3,6,9,24,27,33-hexaoxaheptacyclo[28.7.1.0.0.0.0 .0]octatriaconta-1(38),11,13,15,17,19,21,34,36-nonaen-29-yl]acetic acid
10,24-(Epoxymethano)-11H-4,9,12,23,25-pentaoxadibenzo[5',6':7',8']cyclododeca[1',2':7,8]cycloundeca[1,2,3-de]naphthalene-7-acetic acid, 5,6,6a,7,8,9a,10,13,22,23a,24,26-dodecahydro-2,3,6,15,16,17,18,19,20-nonahydroxy-5,8,13,22,26-pentaoxo-27-[(3,4,5-trihydroxybenzoyl)oxy]-, (6S,6aS,7S,9aR,10R,23aS,24R,27S)-
CHEBULAGIC ACID(RG)

Biological Activity

[Description]:

Chebulagic acid is a COX-LOX dual inhibitor isolated from the fruits of Terminalia chebula Retz, on angiogenesis.target: COX-LOX [1]In vitro: Chebulagic acid can enhance the autophagy. Chebulagic acid exert anti-inflammatory and anti-infective effects. [1] [2] Chebulagic acid also show a protective effect against 1-methyl-4-phenylpyridinium (MPP+) - induce cytotoxicity which mimics the pathological symptom of Parkinson's disease. Chebulagic acid inhibit the LPS-induced upregulation of TNF-α and IL-1β in a dose- and time-dependent manner. Furthermore, LPS-activated MAPK signaling is inhibited by CA treatment in the EA.hy926 cells. [3]

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Natural Products >> Phenols

[References]

[1]. Kim HJ et al. Neuroprotective Effect of Chebulagic Acid via Autophagy Induction in SH-SY5Y Cells. Biomol Ther (Seoul). 2014 Jul;22(4):275-81.

[2]. Liu Y et al. Chebulagic acid inhibits the LPS-induced expression of TNF-α and IL-1β in endothelial cells by suppressing MAPK activation. Exp Ther Med. 2015 Jul;10(1):263-268.

[3]. Athira AP et al. Inhibition of Angiogenesis In Vitro by Chebulagic Acid: A COX-LOX Dual Inhibitor. Int J Vasc Med. 2013;2013:843897.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Boiling Point ]:
1610.6±65.0 °C at 760 mmHg

[ Melting Point ]:
>300℃

[ Molecular Formula ]:
C₄₁H₃₀O₂₇

[ Molecular Weight ]:
954.661

[ Flash Point ]:
480.0±27.8 °C

[ Exact Mass ]:
954.097473

[ PSA ]:
447.09000

[ LogP ]:
2.25

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

[ Index of Refraction ]:
1.876

[ Storage condition ]:
-20°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

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...

[Analysis of tannins in Fructus Chebulae and its confusion varieties by HPCE].

Yao Xue Xue Bao 36(4) , 292-5, (2001)

To analyze the hydrolyzable tannins-chebulinic acid (I) and chebulagic acid(II) in Fructus Chebulae and its confusion varieties by using high performance capillary electrophoresis (HPCE) method.Using ...

[Assay of three hydrolyzable tannins in Fructus Chebulae from different habitats by RP-HPLC].

Zhong Yao Cai 23(6) , 328-30, (2000)

Three hydrolyzable tannins chebulinic acid (I), chebulagic acid(II) and 1,3, 6-tri-O-galloyl-beta-D-glucose (III) in Fructus Chebulae from different habitats were determined by RP-HPLC method. The con...