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.