An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: studies by NMR spectroscopic and computational methods.
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.
Areche
Carlos
C
Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile.
San-Martín
Aurelio
A
Rovirosa
Juana
J
Soto-Delgado
Jorge
J
Contreras
Renato
R
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
D004224:Diterpenes; D013729:Terpenes; C094447:stypotriol