title: Structure and synthesis of a unique isonitrile lipid isolated from the marine mollusk Actinocyclus papillatus.
abstract: The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.
authors.affiliation: Consiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34, 80078 Pozzuoli (Na), Italy.
authors.forename: Emiliano
authors.initials: E
authors.lastname: Manzo
authors.forename: Marianna
authors.initials: M
authors.lastname: Carbone
authors.forename: Ernesto
authors.initials: E
authors.lastname: Mollo
authors.forename: Carlo
authors.initials: C
authors.lastname: Irace
authors.forename: Antonio
authors.initials: A
authors.lastname: Di Pascale
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.forename: Maria Letizia
authors.initials: ML
authors.lastname: Ciavatta
authors.forename: Guido
authors.initials: G
authors.lastname: Cimino
authors.forename: Yue-Wei
authors.initials: YW
authors.lastname: Guo
authors.forename: Margherita
authors.initials: M
authors.lastname: Gavagnin
mesh_terms: D000818:Animals; D002942:Circular Dichroism; D008055:Lipids / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D008055:Lipids; D009570:Nitriles; C558885:actisonitrile