Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues.

Syringin (), a natural bioactive glucoside isolated from the root of (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (), along with its natural analogues -, from a common starting material, syringaldehyde (), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds -, , and exhibited different levels of anti-inflammatory activity.