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Chebulinic acid

$610

  • Brand : BIOFRON

  • Catalogue Number : BD-P0618

  • Specification : 95.0%(HPLC)

  • CAS number : 18942-26-2

  • PUBCHEM ID : 72284

  • Volume : 25mg

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Catalogue Number

BD-P0618

Analysis Method

HPLC,NMR,MS

Specification

95.0%(HPLC)

Storage

-20℃

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Tannin derived from divi-divi (fruit of Caesalpinia coriaria) and myrobalans (fruit of Terminalia chebula). Also obtainable from Geranium thunbergii and the seeds of sal (Shorea robusta)

Structure Type

Phenols

Category

Standards;Natural Pytochemical;API

SMILES

C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C(C(C(=O)O3)CC(=O)O)C(C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O

Synonyms

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

IUPAC Name

2-[(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)oxymethyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.14,8.016,20]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

Applications

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

Density

2.0±0.1 g/cm3

Solubility

Methanol; Ethanol

Flash Point

437.2±27.8 °C

Boiling Point

1460.0±65.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30-,31+,33-,34+,41-/m0/s1

InChl Key

YGVHOSGNOYKRIH-FJPMMHPYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:18942-26-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29317168

Abstract

Glutamate-induced excitotoxicity and oxidative stress is a major causative factor in neuronal cell death in acute brain injuries and chronic neurodegenerative diseases. The prevention of oxidative stress is a potential therapeutic strategy. Therefore, in the present study, we aimed to examine a potential therapeutic agent and its protective mechanism against glutamate-mediated cell death. We first found that chebulinic acid isolated from extracts of the fruit of Terminalia chebula prevented glutamate-induced HT22 cell death. Chebulinic acid significantly reduced intracellular reactive oxygen species (ROS) production and Ca2+ influx induced by glutamate. We further demonstrated that chebulinic acid significantly decreased the phosphorylation of mitogen-activated protein kinases (MAPKs), including ERK1/2, JNK, and p38, as well as inhibiting pro-apoptotic Bax and increasing anti-apoptotic Bcl-2 protein expression. Moreover, we demonstrated that chebulinic acid significantly reduced the apoptosis induced by glutamate in HT22 cells. In conclusion, our results in this study suggest that chebulinic acid is a potent protectant against glutamate-induced neuronal cell death via inhibiting ROS production, Ca2+ influx, and phosphorylation of MAPKs, as well as reducing the ratio of Bax to Bcl-2, which contribute to oxidative stress-mediated neuronal cell death.

KEYWORDS

Calcium; Chebulinic acid; Glutamate; HT22 cells; Mitogen-activated protein kinase; Reactive oxygen species.

Title

Chebulinic Acid Attenuates Glutamate-Induced HT22 Cell Death by Inhibiting Oxidative Stress, Calcium Influx and MAPKs Phosphorylation

Author

Ji Hoon Song 1 , Myoung-Sook Shin 2 , Gwi Seo Hwang 2 , Seong Taek Oh 3 , Jung Jin Hwang 4 , Ki Sung Kang 5

Publish date

2018 Feb 15

PMID

28924208

Abstract

Excessive migration of vascular smooth muscle cells (VSMCs) after vascular injury contributes to the development of occlusive vascular disease. Inhibition of VSMC migration is a validated therapeutic modality for occlusive vascular diseases, such as atherosclerosis and restenosis. We investigated the inhibitory effect of chebulinic acid (CBA) on cell migration and matrix metalloproteinase (MMP)-2 activation in platelet-derived growth factor (PDGF)-BB-induced mouse and human VSMCs. CBA significantly inhibited PDGF-BB-induced migration in mouse and human VSMCs, without inducing cell death. Additionally, CBA significantly blocked PDGF-BB-induced phosphorylation of the PDGF receptor (PDGF-R), Akt, and extracellular signal-regulated kinase (ERK)1/2 by inhibiting the activation of the PDGF-BB signalling pathway. In both mouse and human VSMCs, CBA inhibited PDGF-induced MMP-2 mRNA and protein expression as well as the proteolytic activity of MMP-2. Moreover, CBA suppressed sprout outgrowth formation of VSMCs from endothelium-removed aortic rings as well as neointima formation following rat carotid balloon injury. Taken together, our findings indicated that CBA inhibits VSMC migration by decreasing MMP-2 expression through PDGF-R and the ERK1/2 and Akt pathways. Our data may improve the understanding of the antiatherogenic effects of CBA in VSMCs.

KEYWORDS

Calcium; Chebulinic acid; Glutamate; HT22 cells; Mitogen-activated protein kinase; Reactive oxygen species.

Title

Chebulinic Acid Inhibits Smooth Muscle Cell Migration by Suppressing PDGF-Rβ Phosphorylation and Inhibiting Matrix metalloproteinase-2 Expression

Author

In-Sung Song 1 2 , Yu Jeong Jeong 1 2 , Jung-Hyun Park 1 2 , Sungbo Shim 3 , Sung-Wuk Jang 4 5

Publish date

2017 Sep 18

PMID

30587184

Abstract

Background: Triphala is an Ayurvedic rasayana formulation reputed for its antitumour activities, and chebulinic acid and chebulagic acid, along with other phenolic acids, have been proposed to be responsible for its effects.
Methods: In this study, the anti-proliferative activities of these agents were evaluated in colorectal carcinoma cell lines with three phenotypes exposed to several batches of triphala samples with different quantities of chebulinic acid and chebulagic acid. The pro-apoptotic and anti-migratory activities and the probable antitumour mechanisms of the more potent anti-proliferative phytochemical were also investigated.
Results: The results demonstrated that chebulinic acid, which exerts potent anti-proliferative, pro-apoptotic and anti-migratory effects, is a key molecule for maintaining the antitumour efficacy of triphala. The antitumour mechanism of chebulinic acid is probably related to the PI3K/AKT and MAPK/ERK pathways.
Conclusions: Chebulinic acid is not only a critical component of the anticancer activities of triphala but also a promising natural multi-target antitumour agent with therapeutic potential.

KEYWORDS

Chebulagic acid; Chebulinic acid; Colon cancer; Triphala.

Title

Chebulinic Acid Derived From Triphala Is a Promising Antitumour Agent in Human Colorectal Carcinoma Cell Lines

Author

Min Wang 1 , Yanru Li 2 , Xianda Hu 3

Publish date

2018 Dec 27