title: Absolute Configuration of (-)-Centratherin, a Sesquiterpenoid Lactone, Defined by Means of Chiroptical Spectroscopy.
abstract: (-)-Centratherin is a bioactive sesquiterpenoid lactone, whose absolute configuration (AC) was not established, but has been proposed based on those of germacrane precursors. To verify this proposal, the experimental electronic circular dichroism (ECD), electronic dissymmetry factor (EDF), optical rotatory dispersion (ORD), vibrational circular dichroism (VCD), and vibrational dissymmetry factor (VDF) spectra of (-)-centratherin have been analyzed with the corresponding density functional theoretical predictions. These analyses suggest the AC of naturally occurring (-)-centratherin to be (6R,7R,8S,10R,2'Z).
authors.affiliation: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.|Department of Chemistry, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors.forename: Fernando M S
authors.initials: FM
authors.lastname: Junior
authors.affiliation: Department of Chemistry, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors.forename: Cody L
authors.initials: CL
authors.lastname: Covington
authors.affiliation: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors.forename: Ana Carolina F
authors.initials: AC
authors.lastname: de Albuquerque
authors.affiliation: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors.forename: Jonathas F R
authors.initials: JF
authors.lastname: Lobo
authors.affiliation: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors.forename: Ricardo M
authors.initials: RM
authors.lastname: Borges
authors.affiliation: Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro , 21941-902, Rio de Janeiro, RJ, Brazil.
authors.forename: Mauro B
authors.initials: MB
authors.lastname: de Amorim
authors.affiliation: Department of Chemistry, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors.forename: Prasad L
authors.initials: PL
authors.lastname: Polavarapu
mesh_terms: D002942:Circular Dichroism; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology; D008956:Models, Chemical; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009905:Optical Rotatory Dispersion; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D012717:Sesquiterpenes; C442701:centratherin