oroidin and 3-hydroxykynurenine

Three structurally unique bromopyrrole alkaloids, agelamadins C-E (1-3), were isolated from a marine sponge Agelas sp. Agelamadin C (1) possesses a hybrid structure of oroidin and 3-hydroxykynurenine connected through a dihydro-1,4-oxazine moiety. Agelamadins D (2) and E (3) are a C-9/C-10 diastereomer and a 10-epimer of 1, respectively. The structures of 1-3 were elucidated on the basis of spectroscopic analysis as well as application of a PGME method and a TDDFT ECD calculation. Antimicrobial activity of 1-3 was evaluated.

Topics: Agelas; Alkaloids; Animals; Anti-Infective Agents; Cryptococcus neoformans; Hydrocarbons, Brominated; Kynurenine; Microbial Sensitivity Tests; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pyrroles