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...
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Veröffentlicht in: | Phytochemistry (Oxford) 2006-05, Vol.67 (10), p.944-955 |
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Format: | Artikel |
Sprache: | eng |
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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. |
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ISSN: | 0031-9422 1873-3700 |
DOI: | 10.1016/j.phytochem.2006.03.011 |