jasmonic-acid and Inflammation

Chinese oak (Quercus serrata var. brevipetiolata) belongs to the genus Quercus in Fagaceae family. Its seed, called as Chinese acorn, has been served as a traditional medicine and foodstuff in China. In this study, ten jasmonates were isolated and purified from Chinese acorn, including five new (1-5) and five known jasmonates (6-10). The new jasmonates were identified as butyl (1R,2R)-2-[(2'Z)-5'-hydroxy-penten-2'-enyl]-3-oxo-cyclopentane acetate (1), methyl {2-[4'-(β-d-glucopyranosyloxy)-pentyl}-3-oxo-cyclopentane acetate (2), methyl {(1R,2R)-2-[(2'Z,4'R)-4'-(β-d-glucopyransyloxy)-pent-2'-enyl]}-3-oxo-cyclopentane acetate (3), methyl {(1R,2R)-2-[(2'E,4'S)-4'-(β-d-glucopyransyloxy)-pent-2'-enyl]}-3-oxo-cyclopentane acetate (4), and methyl {(1R,2R)-2-[(2'S,3'E)-2'-(β-D-glucopyransyloxy)-pent-3'-enyl]}-3-oxo-cyclopentane acetate (5), respectively. The isolated jasmonates were evaluated for anti-neuroinflammatory activity, and some showed pronounced inhibitory effects on the production of nitric oxide (NO) induced by lipopolysaccharide (LPS) in BV-2 microglia cells. Some jasmonates could dose-dependently reduce the expression of LPS-induced pro-inflammatory factors (iNOS and COX-2) and could block NF-κB nuclear translocation. This study suggested that Chinese acorns could be served as a healthy product for neuroinflammatory related diseases, such as Alzheimer's disease.

Topics: Anti-Inflammatory Agents; Cyclopentanes; Humans; Inflammation; Inflammation Mediators; Molecular Structure; NF-kappa B; Oxylipins; Quercus; Structure-Activity Relationship