title: An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: studies by NMR spectroscopic and computational methods.
abstract: Meroditerpenoids, 2-[2'(E)-3',7',11',15'-tetramethylhexadec-2-en-1'-yl]-6-methyl-1,4-benzohydroquinone diacetate and 4'-chlorostypotriol triacetate, along with eight known compounds isolated from the dichloromethane extract of the brown alga Stypopodium flabelliforme after peracetylation are reported. One of them, 2-(1-oxo-hexadecyl)-1,3,5-trihydroxybenzene, is described for the first time within this genus. Structural elucidation was carried out on the basis of spectroscopic data and theoretical studies using GIAO/DFT analysis at B3LYP/6-31G(d) and mPW1PW91/6-31G(d) levels of theory for 4'-chlorostypotriol. This isomer is the first metabolite from the Stypopodium genus possessing one halogen atom.
authors.affiliation: Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile.
authors.forename: Carlos
authors.initials: C
authors.lastname: Areche
authors.forename: Aurelio
authors.initials: A
authors.lastname: San-Martín
authors.forename: Juana
authors.initials: J
authors.lastname: Rovirosa
authors.forename: Jorge
authors.initials: J
authors.lastname: Soto-Delgado
authors.forename: Renato
authors.initials: R
authors.lastname: Contreras
mesh_terms: D019295:Computational Biology / Q000379:methods*; D004224:Diterpenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D000459:Phaeophyceae / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry
chemical_list: D004224:Diterpenes; D013729:Terpenes; C094447:stypotriol