title: Thelepamide: an unprecedented ketide-amino acid from Thelepus crispus, a marine annelid worm.
abstract: Thelepamide (1) was characterized during a program to study cytotoxic substances from an unusual source, the tidal zone-derived annelid Thelephus crispus. Its structure contains a tetraketide and a tripeptide subunit and possesses striking atom diversity, consisting of 17 carbons and 8 heteroatoms. The relative configurations at four chiral sites were elucidated via ROESY, J-based configurational analysis, and DFT calculations. It was modestly active against leukemia cells (IC50 = 5 μg/mL) and inactive against solid tumor cell lines.
authors.affiliation: Departamento de Química Fundamental, Facultade de Ciencias and Centro de Investigaciones Científicas Avanzadas (CICA), Universidade da Coruña , 15071 A Coruña, Spain.
authors.forename: Jaime
authors.initials: J
authors.lastname: Rodríguez
authors.forename: Rosa M
authors.initials: RM
authors.lastname: Nieto
authors.forename: María
authors.initials: M
authors.lastname: Blanco
authors.forename: Frederick A
authors.initials: FA
authors.lastname: Valeriote
authors.forename: Carlos
authors.initials: C
authors.lastname: Jiménez
authors.forename: Phillip
authors.initials: P
authors.lastname: Crews
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D005260:Female; D045325:HCT116 Cells; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011077:Polychaeta / Q000737:chemistry*; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D061065:Polyketides; C000589877:thelepamide