Somerville, Michael JKatavic, Peter LLambert, Lynette KPierens, Gregory KBlanchfield , Joanne ThereseCimino, GuidoMollo, ErnestoGavagnin, MargheritaBanwell, MartinGarson, Mary J2015-12-100163-3864http://hdl.handle.net/1885/67135This first chemical study of the sacoglossan mollusk Thuridilla splendens from Mooloolaba, South East Queensland, has resulted in the isolation of three new metabolites, thuridillins D-F (1-3), and one known metabolite, thuridillin A (4). Thuridillin D (1) was isolated by conventional flash chromatography on silica gel, while a mixture of thuridillins E (2) and F (3) was obtained by PTLC on AgNO3-impregnated silica gel. Thuridillins D-F were determined to be structurally related to thuridillin B (5); 1 possessed a hydroxy group at C-11, and 2 and 3 were Δ10,11- and Δ11,12- isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and 1H-1H coupling studies enabled assignment of the individual relative configurations of the epoxylactone, the 2,5-diacetoxy-2,5-dihydrofuran, and cyclohexyl moieties within thuridillin D (1).Keywords: diterpene; epoxide; hydroxyl group; lactone; silica gel; silver nitrate; thuridillin d; thuridillin e; thuridillin f; unclassified drug; article; carbon nuclear magnetic resonance; chromatography; drug conformation; drug isolation; drug structure; heteron201210.1021/np300442s2016-02-24