Tagetnoic acid, a new lipoxygenase inhibitor peroxy fatty acid from Tagetes minuta growing in Saudi Arabia.

A new peroxy fatty acid, tagetnoic acid ( 5 ) [4-((3 S ,6 S )-6-((3 E ,8 E )-octadeca-3,8-dien-1-yl)-3,6-dihydro-1,2-dioxin-3-yl)butanoic acid] and four known metabolites: ecliptal (5-formyl- α -terthiophene) ( 1 ), 5-(4-hydroxybut-1-ynyl)-2,2'-bithiophene ( 2 ), 22,23-dihydrospinasterone ( 3 ), and stigmasterol ( 4 ) were separated from the n -hexane fraction of the aerial parts of Tagetes minuta L. (Asteraceae). Their chemical structures were verified using IR, UV, 2D and 1D NMR, and HRMS. Compounds 3-5 displayed potent lipoxygenase inhibitory potential with IC ₅₀ s 2.26, 1.83, and 1.17 μM, respectively compared to indomethacin (IC ₅₀ 0.89 μM). Moreover, molecular docking study revealed that the potent activity of 5 is due to H-bonding and hydrophobic interaction. The results of this study suggested that Tagetes minuta dietary consumption would be useful for the individuals at risk of acute and chronic inflammatory disorders.