Jasmonates from Chinese acorns (Quercus serrata var. brevipetiolata) exert pronounced anti-neuroinflammatory activities

Abstract 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.