Atypical Nitrogen-Containing Flavonoid in the Fruits of Cumin ( L.) with Anti-inflammatory Activity.

The dried seeds of L. have been traditionally used as food and medicine. To explore its chemical composition and anti-inflammatory activity, four new compounds (-) along with five known compounds (-) were isolated from the seeds in the present study. The chemical structures of the new compounds were identified as follows: methyl 3-((7-purin-2-yl) amino)-3-(4-isopropylphenyl) propanoate (), 8-(amino(4-isopropylphenyl)methyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4-chromene-6-carboxylic acid (), (3,4,5-trihydroxy-6-((4-isopropylbenzyl)oxy)tetrahydro-2-pyran-2-yl)methyl ()-3-(4-propoxyphenyl)acrylate (), and (3,4,5-trihydroxy-6-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4-chromen-7-yl)oxy)tetrahydro-2-pyran-2-yl)methyl 3-(4-isopropylphenyl)-2-methoxypropanoate (). Compound , an atypical nitrogen-containing flavonoid, exhibited the most active inhibitory effect on nitride oxide, with IC of 5.25 μM in the lipopolysaccharide-stimulated RAW264.7 cell assay. Compound was found to suppress the expression levels of inducible nitric oxide synthase and cyclooxygenase-2. Furthermore, it was revealed that both nuclear factor κB and mitogen-activated protein kinase were involved in the anti-inflammatory process of compound .