Anti-inflammatory activity of synthetic and natural glucoraphanin

Glucoraphanin is one of the best known glucosinolates because of its health benefits. The compound is known to eliminate carcinogens in tissue and hence is frequently studied for its cancer preventative properties. In this work, the total synthesis of α- and β-glucoraphanin epimers was attempted. β-Glucoraphanin potassium salt was successfully synthesized in high overall yield, whereas the α-epimer was found to be unstable as it decomposed in the final step of the total synthesis. The anti-inflammatory activity of the synthetic glucoraphanin was determined by inhibition of the release of tumor necrosis factor alpha (TNF-α) secretion in lipopolysaccharide-stimulated THP-1 cells. It was shown that in the presence of either the synthetic or natural glucoraphanin, TNF-α secretion was significantly reduced (≈52 % inhibition) at a concentration of 15 μM.