Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
Hongbo Dong, Min Wu, Yingying Wang, Weihong Du, Yujiao He, Zheng Shi
Abstract
Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2–12, from a common starting material, syringaldehyde (13), 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 1–5, 7, and 9 exhibited different levels of anti-inflammatory activity.
Topics & Concepts
SyringaldehydeChemistryGlucosideTotal synthesisAnti-inflammatoryTraditional medicineStereochemistryPharmacognosyBiological activityBiologyBiochemistryPharmacologyIn vitroMedicineVanillinPathologyAlternative medicineNatural product bioactivities and synthesisPhytochemistry and Biological ActivitiesGenomics, phytochemicals, and oxidative stress