title: Defensive sesquiterpenes from Senecio candidans and S. magellanicus, and their structure-activity relationships.
abstract: Eleven eremophilanolides, 1-3 and 6-13, and two eremophilanes, 24 and 25, were isolated from Senecio candidans and S. magellanicus from the Magallanes Region (Chile). Compounds 2, 3, 9, and 10 have not been previously reported as natural products. Their structures were established by NMR spectroscopic analysis and chemical transformations. The X-ray analysis of compounds 11, 13, and 17 were also performed. Different semisynthetic analogs from eremophilanolide 11 were generated to carry out a structure-activity relationship study. Their possible plant defensive role was tested against herbivorous insects (Spodoptera littoralis, Rhopalosiphum padi, and Myzus persicae) and plants (Lactuca sativa). Additionally, their effects on insect (Sf9) and mammalian (CHO) cell lines were tested.
authors.affiliation: Instituto de Productos Naturales y Agrobiología (IPNA), CSIC, ES-38206 La Laguna, Tenerife. mreina@ipna.csic.es
authors.forename: Matías
authors.initials: M
authors.lastname: Reina
authors.forename: Omar
authors.initials: O
authors.lastname: Santana
authors.forename: Dulce M
authors.initials: DM
authors.lastname: Domínguez
authors.forename: Luis
authors.initials: L
authors.lastname: Villarroel
authors.forename: Víctor
authors.initials: V
authors.lastname: Fajardo
authors.forename: Matías L
authors.initials: ML
authors.lastname: Rodríguez
authors.forename: Azucena
authors.initials: A
authors.lastname: González-Coloma
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D018360:Crystallography, X-Ray; D035264:Flowers / Q000737:chemistry; D007306:Insecticides / Q000737:chemistry; D008968:Molecular Conformation; D012674:Senecio / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D018411:Spodoptera / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D012717:Sesquiterpenes