title: seco-Briarellinone and briarellin S, two new eunicellin-based diterpenoids from the Panamanian octocoral Briareum asbestinum.
abstract: Two new eunicellin-based diterpenes, seco-briarellinone (1) and briarellin S (2), and a known seco-asbestinin (3) have been isolated from the methanolic extract of the common octocoral Briareum asbestinum collected in Bocas del Toro, Caribbean of Panama. The structures and relative stereochemistry of the compounds were defined using extensive spectroscopic analysis including 1D, 2D-nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). Compounds 1 and 2 displayed anti-inflammatory properties inhibiting nitric oxide (NO) production induced by lipopolisacharide (LPS) in macrophages with an Inhibitory concentration 50% (IC₅₀) of 4.7 μM and 20.3 μM, respectively. This is the first report of briarellin diterpenes containing a ketone group at C-12.
authors.affiliation: Center for Drug Discovery and Biodiversity, Institute for Scientific Research and Technology Services-INDICASAT, Clayton, City of Knowledge, P.O. Box 0843-01103, Panama.
authors.forename: José Félix
authors.initials: JF
authors.lastname: Gómez-Reyes
authors.forename: Ana
authors.initials: A
authors.lastname: Salazar
authors.forename: Héctor M
authors.initials: HM
authors.lastname: Guzmán
authors.forename: Yisett
authors.initials: Y
authors.lastname: González
authors.forename: Patricia L
authors.initials: PL
authors.lastname: Fernández
authors.forename: Armando
authors.initials: A
authors.lastname: Ariza-Castolo
authors.forename: Marcelino
authors.initials: M
authors.lastname: Gutiérrez
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000893:Anti-Inflammatory Agents / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D004224:Diterpenes / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000633:toxicity; D008264:Macrophages / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008810:Mice, Inbred C57BL; D009569:Nitric Oxide / Q000378:metabolism; D010176:Panama
chemical_list: D000893:Anti-Inflammatory Agents; D004224:Diterpenes; D008070:Lipopolysaccharides; C580977:briarellin S; C476503:eunicellin; C580976:seco-briarellinone; D009569:Nitric Oxide