An experimental approach to study the biosynthesis of brominated metabolites by the red algal genus Laurencia

Abstract

The production of labeled brominated metabolites with radioactive 82 Br in Laurencia species was investigated as part of a study of the biosynthesis of halogenated metabolites from species belonging to the red algal genus Laurencia (Rhodomelaceae, Ceramiales Br-containing metabolites. In the case of the laurencin-producing race of L. nipponica, laurencin and deacetyllaurencin were found to be produced in approximately 1:1 ratio, though laurencin is the major metabolite in the wild sample. Furthermore, when cultured in the dark, the production rates of brominated metabolites in Laurencia spp. were found to be diminished. The present study strongly indicates that the use of radiobromine [ 82 Br] in combination with the TLC-ARLG method is an effective approach for investigating the biosynthesis of brominated metabolites in Laurencia.3

The Laurencia Paradox: An Endless Source of Chemodiversity

“…Furthermore, when Laurencia spp. specimens were cultured in the dark, the production rates of brominated metabolites were diminished [58].…”

Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology

“…495,496 In 1992, the same group described a single-step, LPO-catalyzed intramolecular cyclization of (3Z,6S,7S)-laurediol to produce laureatin (481) and its key intermediate prelaureatin (485). 497 The result also suggests that laurediols are the precursors of Laurencia derived ACGs, and that LPO has very low substrate specificity.…”

“…The work demonstrated that the use of 82 Br provides an effective approach to investigating the biosynthesis of brominated metabolites in Laurencia species, though the half-life of 82 Br is very short (35.3 h) as compared with those of the more commonly used tracers 14 C (5730 y) and 3 H (12.3 y). 485 …”

Phytochemical and Biological Properties of Sesquiterpene Constituents From the Marine Red Seaweed Laurencia: A Review

“…In particular, species of Laurencia are known to be the richest producers of halogenated secondary metabolites with diverse and unique structural features depending on species, localities and season [5]. Laurencia species produce bromine-containing compounds in much larger numbers than either chlorine-or iodine-containing ones whereas, the Clcontaining compounds usually also possess Br atom(s) [6]. A large number of these compounds have been obtained from Laurencia species having an intracellular, membrane-bound vesicles known as "corps en cerise" (cherry bodies) in the outer cell layer (the cortical layer) where, these inclusions are considered as a synthesis and/or storage sites of halogenated secondary metabolites [7].…”