Benzyl sulfide, sulfoxide and sulfinate metabolites from Gastrodia elata and their synthesis, derivatization and anti-inflammatory activity.

Five novel sulfur-containing benzyl metabolites, designated as gastrabenzylsulfoxides A and B (1 and 2), gastrabenzylsulfinate A (3) and gastrabenzylsulfides A and B (4 and 5), along with four known compounds (6-9), were isolated from the aqueous extracts of Gastrodia elata. Compounds 1 and 4 are 4-hydroxy-3-(4'-hydroxybenzyl)benzyl-substituted sulfoxide and sulfide, respectively, which are unprecedented in natural products. Compound 3 represents a rare sulfinate. Several isolates and their sulfone and disulfide analogs (10-13) were synthesized to evaluate their anti-inflammatory activity. Notably, the synthesized sulfone 10 demonstrated significant alleviation of symptoms in multiple in vivo inflammatory models.