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

Resultado de la investigación: Article

22 Citas (Scopus)

Resumen

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.

Idioma originalEnglish
Páginas (desde-hasta)1315-1320
Número de páginas6
PublicaciónPhytochemistry
Volumen70
N.º10
DOI
EstadoPublished - 1 jul 2009

Huella dactilar

Phaeophyta
halogens
Halogens
Phaeophyceae
Methylene Chloride
methylene chloride
Algae
Metabolites
Computational methods
Discrete Fourier transforms
Isomers
isomers
Theoretical Models
Nuclear magnetic resonance
metabolites
Atoms
extracts
methodology
Stypopodium flabelliforme
Stypopodium

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Citar esto

Areche, Carlos ; San-Martín, Aurelio ; Rovirosa, Juana ; Soto-Delgado, Jorge ; Contreras, Renato. / An unusual halogenated meroditerpenoid from Stypopodium flabelliforme : Studies by NMR spectroscopic and computational methods. En: Phytochemistry. 2009 ; Vol. 70, N.º 10. pp. 1315-1320.
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An unusual halogenated meroditerpenoid from Stypopodium flabelliforme : Studies by NMR spectroscopic and computational methods. / Areche, Carlos; San-Martín, Aurelio; Rovirosa, Juana; Soto-Delgado, Jorge; Contreras, Renato.

En: Phytochemistry, Vol. 70, N.º 10, 01.07.2009, p. 1315-1320.

Resultado de la investigación: Article

TY - JOUR

T1 - An unusual halogenated meroditerpenoid from Stypopodium flabelliforme

T2 - Studies by NMR spectroscopic and computational methods

AU - Areche, Carlos

AU - San-Martín, Aurelio

AU - Rovirosa, Juana

AU - Soto-Delgado, Jorge

AU - Contreras, Renato

PY - 2009/7/1

Y1 - 2009/7/1

N2 - 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.

AB - 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.

KW - Dictyotaceae

KW - GIAO/DFT

KW - Meroditerpenoids

KW - Seaweeds

KW - Stypopodium flabelliforme

KW - Stypotriol

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U2 - 10.1016/j.phytochem.2009.07.017

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M3 - Article

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JO - Phytochemistry

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