Conosiligins A-D, Ring-Rearranged Tremulane Sesquiterpenoids from Conocybe siliginea

Abstract

Conosiligins A-D (1-4), four ring-rearranged sesquiterpenoids, were isolated from cultures of the basidiomycete Conocybe siliginea. Their structures and absolute configurations were determined by detailed spectroscopic analyses and equivalent circulating density (ECD) calculations. Compounds 1 and 2 possess a 5/8-fused ring system, while 3 has a 5/6-fused backbone conjugated with a γ-lactone. Compound 4 is a 5,6-seco tremulane derivative with the loss of a skeletal carbon, featuring a tetracyclic system involving a pyranone moiety. Compounds 3 and 4 inhibited Con A-induced T cell proliferation with IC₅₀ values of 12.3 and 6.6 μM, respectively.