Tetraprenyltoluquinols from the brown alga Cystophora fibrosa

Enantiomeric 4′-methoxyamentol, a tetracyclic tetraprenyltoluquinol, has been isolated from the South African marine brown alga Cystophora fibrosa as well as another five amentol derivatives with a further five stereoisomers. The stereochemistry of these compounds is discussed in relation to the res...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Phytochemistry (Oxford) 2006-05, Vol.67 (10), p.944-955
Hauptverfasser: Laird, Damian W., van Altena, Ian A.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Enantiomeric 4′-methoxyamentol, a tetracyclic tetraprenyltoluquinol, has been isolated from the South African marine brown alga Cystophora fibrosa as well as another five amentol derivatives with a further five stereoisomers. The stereochemistry of these compounds is discussed in relation to the results of a series of molecular modelling experiments. Six cyclised tetraprenyltoluquinols and five stereoisomers with the previously reported amentol skeleton have been isolated from the lipophilic extract of the South African brown alga Cystophora fibrosa. Structures and relative stereochemistry were determined using spectrometric techniques, particularly 1D and 2D NMR, and molecular modelling experiments. The compounds isolated appear to be enantiomeric to compounds with the same skeleton isolated from brown algae of the genus Cystoseira collected in northern Africa and the Mediterranean Sea. The isolation of tetraprenyltoluquinols with the amentol skeleton from this alga suggests that C. fibrosa should be moved from the genus Cystophora into the Cystoseira.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2006.03.011