title: Isolation of thuridillins D-F, diterpene metabolites from the Australian sacoglossan mollusk Thuridilla splendens; relative configuration of the epoxylactone ring.
abstract: This 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 AgNO(3)-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 Δ(10,11)- and Δ(11,12)-isomers, respectively. HSQC-HECADE NMR data, together with conformational analysis, NOESY experiments, and (1)H-(1)H 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).
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Somerville
authors.forename: Peter L
authors.initials: PL
authors.lastname: Katavic
authors.forename: Lynette K
authors.initials: LK
authors.lastname: Lambert
authors.forename: Gregory K
authors.initials: GK
authors.lastname: Pierens
authors.forename: Joanne T
authors.initials: JT
authors.lastname: Blanchfield
authors.forename: Guido
authors.initials: G
authors.lastname: Cimino
authors.forename: Ernesto
authors.initials: E
authors.lastname: Mollo
authors.forename: Margherita
authors.initials: M
authors.lastname: Gavagnin
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Mary J
authors.initials: MJ
authors.lastname: Garson
mesh_terms: D000818:Animals; D001315:Australia; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D004852:Epoxy Compounds / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods
chemical_list: D004224:Diterpenes; D004852:Epoxy Compounds; D007783:Lactones; C576964:thuridillin D; C576965:thuridillin E; C576966:thuridillin F