Benzyl Sulfide, Sulfoxide and Sulfinate Metabolites from Gastrodia elata and Their Synthesis, Derivatization and Anti-inflammatory Activity

Five new sulfur-bearing benzyl metabolites, designated as gastrabenzylsulfoxides A and B (1 and 2), gastrabenzylsulfinate A (3) and gastrabenzylsulfides A and B (4 and 5), together with four known ones (6−9), were isolated from the aqueous extracts of Gastrodia elata. 1 and 4 are 4-hydroxy-3-(4′-hydroxybenzyl)benzyl-substituted sulfoxide and sulfide, respectively, which are unprecedented in natural products. And 3 is a rare sulfinate. Some isolates and their sulfone and disulfide analogs (10−13) were synthesized for anti-inflammatory activity evaluation. The synthesized sulfone 10 can significantly alleviate symptoms in multiple in vivo inflammatory models.