title: Additional Insights into the Obtusallene Family: Components of Laurencia marilzae.
abstract: The obtusallenes are a significant subset of C15-halogenated acetogenins that incorporate 12-membered cyclic ethers. We have recently reported the isolation from Laurencia marilzae of 12-epoxyobtusallene IV (1) and its related α,β-unsaturated carboxylate ester (2), both of special biogenetic relevance. Here we describe the final step of our study, the isolation of three new analogues (3-5), among these, the first bromopropargylic derivative (3) of this class of macrocyclic C15-acetogenins. The structures were elucidated by analysis of NMR and X-ray data. 12-Epoxyobtusallene IV (1), its new isomer 4, and known obtusallene IV (6) were evaluated for their apoptosis-inducing activities in a human hepatocarcinoma cell line.
authors.affiliation: Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna (ULL) , Avenida Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.|Departamento de Química, Instituto de Química, Facultad de Ciencias, Universidad Autónoma de Santo Domingo , Ciudad Universitaria, 1355 Santo Domingo, Dominican Republic.
authors.forename: Adrián
authors.initials: A
authors.lastname: Gutiérrez-Cepeda
authors.affiliation: Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna (ULL) , Avenida Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: José J
authors.initials: JJ
authors.lastname: Fernández
authors.affiliation: Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna (ULL) , Avenida Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: Manuel
authors.initials: M
authors.lastname: Norte
authors.affiliation: Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna (ULL) , Avenida Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: Matías
authors.initials: M
authors.lastname: López-Rodríguez
authors.affiliation: Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna (ULL) , Avenida Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.|Departamento de Química, Universidad de Antofagasta , Avenida Angamos 601, Antofagasta, Chile.
authors.forename: Iván
authors.initials: I
authors.lastname: Brito
authors.affiliation: Laboratoire d'Innovation Thérapeutique, UMR 7200 CRNS, Faculté de Pharmacie, Université de Strasbourg , 67401 Illkirch, France.
authors.forename: Christian D
authors.initials: CD
authors.lastname: Muller
authors.affiliation: Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna (ULL) , Avenida Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: María L
authors.initials: ML
authors.lastname: Souto
mesh_terms: D054378:Acetogenins / Q000737:chemistry / Q000302:isolation & purification*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D006528:Carcinoma, Hepatocellular / Q000628:therapy; D018360:Crystallography, X-Ray; D004988:Ethers, Cyclic / Q000737:chemistry*; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D044722:Laurencia / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D013030:Spain
chemical_list: C000610791:12-epoxyobtusallene IV; D054378:Acetogenins; D000970:Antineoplastic Agents; D004988:Ethers, Cyclic; D006842:Hydrocarbons, Brominated; C522877:obtusallene