An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods

Carlos Areche, Aurelio San-Martín, Juana Rovirosa, Jorge Soto-Delgado, Renato Contreras

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1315-1320
Number of pages6
JournalPhytochemistry
Volume70
Issue number10
DOIs
Publication statusPublished - Jul 2009

Keywords

  • Dictyotaceae
  • GIAO/DFT
  • Meroditerpenoids
  • Seaweeds
  • Stypopodium flabelliforme
  • Stypotriol

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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