Brominated arginine-derived alkaloids from the red sea sponge Suberea mollis

Abstract

Investigation of a new collection of the Red Sea sponge Suberea mollis afforded two new brominated arginine-derived alkaloids, subereamines A (1) and B (2), a new brominated phenolic compound, subereaphenol D (3), and the known compounds dichloroverongiaquinol (4), aerothionin (5), and purealdin L (6). The structures of the isolated compounds were assigned using one- and two-dimensional NMR spectra and HRFABMS data. The absolute configurations of subereamines A (1) and B (2) were determined by acid hydrolysis followed by chiral-phase LC-MS. The antimicrobial and antioxidant activities of the isolated compounds have been evaluated. Dichloroverongiaquinol and subereaphenol D displayed significant antimicrobial activity. Using the DPPH TLC autographic rapid screen for free radical scavenging effects, subereaphenol D displayed a significant antioxidant effect. In addition, the cytotoxic activities of the isolated compounds were investigated.