Trigonelline

Trigonelline, an alkaloid with potential antidiabetic activity, is present in considerable amounts in coffee. Trigonelline is an efficient Nrf2 inhibitor capable of blocking Nrf2-dependent proteasome activity and thereby apoptosis protection in pancreatic cancer cells.

Product information

CAS Number: 535-83-1

Molecular Weight: 137.14

Formula: C7H7NO2

Synonym:

Trigenolline

Chemical Name: 1-methylpyridin-1-ium-3-carboxylate

Smiles: C[N+]1=CC(=CC=C1)C([O-])=O

InChiKey: WWNNZCOKKKDOPX-UHFFFAOYSA-N

InChi: InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 7.14 mg/mL (52.06 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

It is found that Trigonelline (TG) significantly rescues the morphology of the H9c2 cells. Treatment of cells with Trigonelline attenuates H2O2 induced cell deaths and improves the antioxidant activity. In addition, Trigonelline regulates the apoptotic gene caspase-3, caspase-9 and anti-apoptotic gene Bcl-2, Bcl-XL during H2O2 induced oxidative stress in H9c2 cells. For evident, flow cytometer results also confirms that Trigonelline significantly reduces the H2O2 induced necrosis and apoptosis in H9c2 cells. However, further increment of Trigonelline concentration against H2O2 can induce the necrosis and apoptosis along with H2O2.

In Vivo:

Trigonelline decreases bone mineralization and tends to worsen bone mechanical properties in streptozotocin-induced diabetic rats. In nicotinamide/streptozotocin-treated rats, Trigonelline significantly increases bone mineral density (BMD) and tends to improve cancellous bone strength. Trigonelline differentially affects the skeletal system of rats with streptozotocin-induced metabolic disorders, intensifying the osteoporotic changes in streptozotocin-treated rats and favorably affecting bones in the non-hyperglycemic (nicotinamide/streptozotocin-treated) rats.

References:

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.

Products are for research use only. Not for human use.