title: Cadinane-Type Sesquiterpenoids from Heterotheca inuloides: Absolute Configuration and Anti-inflammatory Activity.
abstract: Eight cadinane-type sesquiterpenoids (1-8) together with some triterpenoids, flavonoids, and sterols were isolated from the aerial parts of Heterotheca inuloides. The structures of the new compounds (1-4) were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis. The structures of the new (1-3) and the known (5-7) sesquiterpenoids were confirmed by X-ray crystallography. The absolute configurations of metabolites 2-5 were determined by comparing their experimental and calculated electronic circular dichroism spectra and confirmed via refinement of the Flack parameter using anomalous X-ray scattering from the oxygen atoms and chemical correlation methods. The sesquiterpenoids were evaluated for their anti-inflammatory potential by applying the TPA-induced mouse ear edema model. The results revealed that some of these metabolites exhibit moderate anti-inflammatory activity. At a dose of 228 μg/ear compound 1 showed 43.14 ± 8.09% inhibition on ear edema, indicating an IC50 > 228 μg/ear.
authors.forename: Verónica
authors.initials: V
authors.lastname: Egas
authors.forename: Rubén A
authors.initials: RA
authors.lastname: Toscano
authors.forename: Edelmira
authors.initials: E
authors.lastname: Linares
authors.forename: Robert
authors.initials: R
authors.lastname: Bye
authors.affiliation: Instituto de Investigaciones en Ecosistemas y Sustentabilidad, Universidad Nacional Autónoma de México , Antigua carretera a Pátzcuaro No. 8701, Col. Ex-Hacienda de San José de la Huerta, 58190 Morelia, Michoacán, Mexico.
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Espinosa-García
authors.forename: Guillermo
authors.initials: G
authors.lastname: Delgado
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019659:Asteraceae / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004195:Disease Models, Animal; D004423:Ear; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy / Q000473:pathology; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013755:Tetradecanoylphorbol Acetate / Q000494:pharmacology
chemical_list: D000893:Anti-Inflammatory Agents; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C508039:cadinane; D013755:Tetradecanoylphorbol Acetate