Isolation, Synthesis, and Radical-Scavenging Activity of Rhodomelin A, a Ureidobromophenol from the Marine Red Alga Rhodomela confervoides

A novel ureidobromophenol, rhodomelin A (1)4 was characterized from Rhodomela confervoides. Its structure was elucidated by spectroscopic analysis. Both enantiomers of 1 were synthesized using a convergent strategy starting from D/L-pyroglutamic acids, respectively, allowing-assignment of the R-configuration for the naturally occurring isomer by chiral HPLC analysis. Rhodomelin A represents the first example of a naturally occurring ureidopyrrolidone alkaloid incorporating a gamma-arninobutyric acid unit. The scavenging activity of I toward DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS (2,2'-azinObis(3-ethylbenzothiazoline-6-sulfonate)) radicals was assayed.