Agelamadins C–E, Bromopyrrole Alkaloids Comprising Oroidin and 3-Hydroxykynurenine from a Marine Sponge Agelas sp.

Organic Letters
2014.0

Abstract

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. © 2014 American Chemical Society.

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