title: Agelamadins C-E, bromopyrrole alkaloids comprising oroidin and 3-hydroxykynurenine from a marine sponge Agelas sp.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Hokkaido University , Sapporo 060-0812, Japan.
authors.forename: Taishi
authors.initials: T
authors.lastname: Kusama
authors.forename: Naonobu
authors.initials: N
authors.lastname: Tanaka
authors.forename: Kanae
authors.initials: K
authors.lastname: Sakai
authors.forename: Tohru
authors.initials: T
authors.lastname: Gonoi
authors.forename: Jane
authors.initials: J
authors.lastname: Fromont
authors.forename: Yoshiki
authors.initials: Y
authors.lastname: Kashiwada
authors.forename: Jun'ichi
authors.initials: J
authors.lastname: Kobayashi
mesh_terms: D047230:Agelas / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003455:Cryptococcus neoformans / Q000187:drug effects; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007737:Kynurenine / Q000031:analogs & derivatives / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000890:Anti-Infective Agents; D006842:Hydrocarbons, Brominated; D011758:Pyrroles; C000593347:agelamadin C; C000593348:agelamadin D; C000593349:agelamadin E; C005045:3-hydroxykynurenine; D007737:Kynurenine; C077209:oroidin