title: Damipipecolin and damituricin, novel bioactive bromopyrrole alkaloids from the Mediterranean sponge Axinella damicornis.
abstract: Two new bromopyrrole alkaloids, damipipecolin (1) and damituricin (2), have been isolated from the Mediterranean sponge Axinella damicornis, and their structures established through spectroscopic methods. Compounds 1 and 2 extend the structural variety of the so far known pyrrole alkaloids; in these compounds, the 4-bromopyrrole 2-carboxylic acid is directly condensed with a non-protein cyclic alpha-amino acid, the (2R, 4R)-trans-4-hydroxypipecolic acid and (2R, 4R)-cis-N,N'-dimethyl-4-hydroxyproline (D-turicine) in 1 and 2, respectively. Compounds 1 and 2 were found to display a modulating effect of the serotonin receptor activity in vitro.
authors.affiliation: Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, via D Montesano 49, Napoli, Italy.
authors.forename: Anna
authors.initials: A
authors.lastname: Aiello
authors.forename: Ernesto
authors.initials: E
authors.lastname: Fattorusso
authors.forename: Antonella
authors.initials: A
authors.lastname: Giordano
authors.forename: Marialuisa
authors.initials: M
authors.lastname: Menna
authors.forename: Werner E G
authors.initials: WE
authors.lastname: Müller
authors.forename: Sanja
authors.initials: S
authors.lastname: Perović-Ottstadt
authors.forename: Heinz C
authors.initials: HC
authors.lastname: Schröder
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D047089:Axinella / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D002118:Calcium / Q000378:metabolism; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D018698:Glutamic Acid / Q000494:pharmacology; D006801:Humans; D019083:Mediterranean Region; D015394:Molecular Structure; D016202:N-Methylaspartate / Q000494:pharmacology; D009474:Neurons / Q000187:drug effects / Q000378:metabolism; D011758:Pyrroles / Q000737:chemistry*; D051381:Rats; D047233:Suberites / Q000187:drug effects / Q000378:metabolism
chemical_list: D000470:Alkaloids; D011758:Pyrroles; C523025:damipipecolin; C523026:damituricin; D018698:Glutamic Acid; D016202:N-Methylaspartate; D001966:Bromine; D002118:Calcium