Sterols from the brown alga Cystoseira foeniculacea : Degradation of fucosterol into saringosterol epimers

The present study was carried out in order to determine the phytochemical composition of the marine brown alga Cystoseira foeniculacea collected off the coasts of Algeria. After a preliminary fractionation of its organic crude extracts by column chromatography, the resulting fractions were further analysed by 1H NMR. Even though algal species of the genus Cystoseira are commonly known to produce a wide variety of meroditerpenoids, in the case of C. foeniculacea none of the fractions were found to contain such compounds: most of the fractions showed typical 1H NMR signals of fatty acids and derivatives (mainly glycerolipids and glycolipids). Nevertheless, the thorough analysis of a sterol-enriched fraction by RP-C8 HPLC led to the isolation, for the first time from this species, of fucosterol (1) and a mixture of saringosterols (2 and 3). The NMR data of compounds 1–3 were fully determined with the help of 1D and 2D experiments which allowed the reassignment of some attributions in comparison with those reported in the literature. This work also confirms evidence of the oxidative degradation of fucosterol into a C-24 epimeric mixture of saringosterols.