Carboxyatractyloside (dipotassium)

Carboxyatractyloside dipotassium is a diterpenoid. Carboxyatractyloside dipotassium can be isolated from plants of the genus Xanthium. Carboxyatractyloside dipotassium is an ADP/ATP carrier inhibitor, inhibiting mitochondrial ADP/ATP transport. Carboxyatractyloside dipotassium promotes ROS production, induces Ca2+ release, and leads to mitochondrial dysfunction. Carboxyatractyloside dipotassium induces lethargy, weakness, and epileptic seizures in rats[1][2][3][4][5][6].

Product Specifications

CAS Number

[33286-30-5]

Product Name Alternative

Gummiferin (dipotassium)

UNSPSC

12352005

Hazard Statement

H301+H311+H331

Target

Calcium Channel; Mitochondrial Metabolism; Reactive Oxygen Species (ROS)

Type

Natural Products

Related Pathways

Immunology/Inflammation; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB

Field of Research

Neurological Disease

Assay Protocol

https://www.medchemexpress.com/carboxyatractyloside-dipotassium.html

Purity

99.57

Solubility

DMSO : 25 mg/mL (ultrasonic; warming; heat to 60°C) |H2O : 100 mg/mL (ultrasonic)

Smiles

C=C([C@H](CC1)C2)[C@H](O)[C@@]32CC[C@]4([H])C(C(O)=O)(C(O)=O)C[C@@H](O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)OS(=O)(O[K])=O)OS(=O)(O[K])=O)OC(CC(C)C)=O)C[C@@]4(C)[C@@]31[H]

Molecular Formula

C31H44K2O18S2

Molecular Weight

847.00

Precautions

H301+H311+H331

References & Citations

[1]Pebay-Peyroula E, et al. Structure of mitochondrial ADP/ATP carrier in complex with carboxyatractyloside. Nature. 2003 Nov 6;426 (6962) :39-44.|[2]Ri M, et al. Identification of Toyocamycin, an agent cytotoxic for multiple myeloma cells, as a potent inhibitor of ER stress-induced XBP1 mRNA splicing. Blood Cancer J. 2012 Jul;2 (7) :e79.|[3]Belosludtseva NV, et al. ANT-Mediated Inhibition of the Permeability Transition Pore Alleviates Palmitate-Induced Mitochondrial Dysfunction and Lipotoxicity. Biomolecules. 2024 Sep 15;14 (9) :1159.|[4]García N, et al. Cyclosporin A is unable to inhibit carboxyatractyloside-induced permeability transition in aged mitochondria. Comp Biochem Physiol C Toxicol Pharmacol. 2009 Apr;149 (3) :374-81. |[5]Luciani S, et al. Effects of carboxyatractyloside a structural analogue of atractyloside on mitochondrial oxidative phosphorylation. Life Sci II. 1971 Sep 8;10 (17) :961-8.|[6]Hatch RC, et al. Toxicologic study of carboxyatractyloside (active principle in cocklebur--Xanthium strumarium) in rats treated with enzyme inducers and inhibitors and glutathione precursor and depletor. Am J Vet Res. 1982 Jan;43 (1) :111-6.