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Vertebrata lanosa is a red alga that can commonly be found along the shores of Europe and North America. Its composition of bromophenols has been studied intensely. The aim of the current study was therefore to further investigate the phytochemistry of this alga, focusing more on the polar components. In total, 23 substances were isolated, including lanosol-4,7-disulfate (4) and the new compounds 3,5-dibromotyrosine (12), 3-bromo-5-sulfodihydroxyphenylalanine (13), 3-bromo-6-lanosyl dihydroxyphenylalanine (14), 3-(6¢-lanosyl lanosyl) tyrosine (15) and 5-sulfovertebratol (16). In addition, 4-sulfo-7-dimethylsulfonium lanosol (7) was identified. While, in general, the dimethylsulfonium moiety is widespread in algae, its appearance in bromophenol is unique. Moreover, the major glycerogalactolipids, including the new ((5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid 3′-[(6′’-O-α-galactopyranosyl-β-D-galactopyranosyl)]-1-glycerol ester (23), and mycosporine-like amino acids, porphyra-334 (17), aplysiapalythine A (18) and palythine (19), were identified.

Marine algae are the source of a plethora of halogenated compounds, in particular brominated phenols, possessing various bioactivities. Since these natural products are typically unavailable commercially, isolation is usually indispensable for biological activity testing. However, targeted isolation may be challenging due to difficulties in identifying desired compounds via high-resolution LC–MS in crude extracts or fractions. While bromophenols have been extensively reviewed regarding their bioactivities, less attention has been given to their distribution and chemotaxonomic relevance among marine algae. Knowledge of the distribution of bromophenols may aid species identification and also point to species containing potentially novel compounds. To facilitate targeted and untargeted isolation of bromophenols from marine algae, an overview of the distribution and chemotaxonomic relevance of algal bromophenols considering recent phylogenetic findings is presented along with key analytical features of bromophenols relevant for mass spectrometric identification. Additionally, a comprehensive database listing brominated phenols from marine algae and their key analytical properties has been constructed.

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