Trigonelline (chloride)

Trigonelline chloride is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline chloride is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline chloride also has anti-HSV-1, antibacterial, and antifungal activity, and induces ferroptosis.

Product Specifications

CAS Number

[6138-41-6]

Product Name Alternative

Trigonelline (hydrochloride)

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Apoptosis; Bacterial; Endogenous Metabolite; Ferroptosis; Fungal; HIV

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis; Metabolic Enzyme/Protease

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/Trigonelline_chloride.html

Concentration

10mM

Purity

99.89

Solubility

DMSO : 20.83 mg/mL (ultrasonic; warming; heat to 60°C) |H2O : 100 mg/mL (ultrasonic)

Smiles

C[N+]1=CC(C(O)=O)=CC=C1.[Cl-]

Molecular Formula

C7H8ClNO2

Molecular Weight

173.60

Precautions

H302, H315, H319, H335

References & Citations

[1]Ilavenil S, et al. Trigonelline protects the cardiocyte from hydrogen peroxide induced apoptosis in H9c2 cells. Asian Pac J Trop Med. 2015 Apr;8 (4) :263-8.|[2]Joanna Folwarczna, et al. Effects of Trigonelline, an Alkaloid Present in Coffee, on Diabetes-Induced Disorders in the Rat Skeletal System. Nutrients. 2016 Mar; 8 (3) : 133.|[3]A Arlt, et al. Inhibition of the Nrf2 transcription factor by the alkaloid trigonelline renders pancreatic cancer cells more susceptible to apoptosis through decreased proteasomal gene expression and proteasome activity. Oncogene. 2013 Oct;32 (40) :4825-35.|[4]Ozçelik B, et al. Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids. Pharm Biol. 2011 Apr;49 (4) :396-402.|[5]Su Y, et al. Ferroptosis, a novel pharmacological mechanism of anti-cancer drugs. Cancer Lett. 2020 Jul 28;483:127-136.