Amino Acid-Coupled Bromophenols and a Sulfated Dimethylsulfonium Lanosol from the Red Alga Vertebrata lanosa

Mar Drugs. 2022 Jun 27;20(7):420. doi: 10.3390/md20070420.

Abstract

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.

Keywords: Vertebrata lanosa; amino acid derivatives; bromophenol; dimethyl sulfonium; sulfate.

MeSH terms

  • Amino Acids*
  • Catechols
  • Rhodophyta* / chemistry
  • Sulfates

Substances

  • Amino Acids
  • Catechols
  • Sulfates
  • lanosol

Grants and funding

Marthe Schmitt received financial support from the Erasmus+ programme for student traineeship. The APC was funded by the Open Access Publication Fund of the University of Münster.