6-C-(E-phenylethenyl)naringenin

6-C-(E-phenylethenyl)naringenin (6-CEPN) is a **styryl flavonoid** compound that represents a hybrid molecule combining stilbene with a flavonoid structure. It is a semi-natural derivative of naringenin that can be found in naringenin-fortified fried beef formed during thermal processing. The compound was identified through computational ligand docking as a **selective cyclooxygenase-1 (COX-1) inhibitor**. 6-CEPN demonstrates multiple mechanisms of action including selective COX-1 inhibition, inhibition of isoprenylcysteine carboxyl methyltransferase (Icmt) leading to RAS pathway suppression, and modulation of Wnt/β-catenin signaling through GSK3β upregulation. The compound has shown anticancer properties in preclinical studies, particularly against colorectal cancer and hepatocellular carcinoma, by inducing cell cycle arrest, autophagy, and inhibiting cancer cell stemness. It also exhibits anti-inflammatory effects through upregulation of the Nrf2 signaling pathway and inhibition of advanced glycation end product (AGE)-induced inflammation. Notably, 6-CEPN possesses higher bioavailability than its parent compound naringenin and has been well-tolerated in animal studies without significant gastrointestinal or systemic toxicity.

Other names

6-C-(E-phenylethenyl)-naringenin