Damipipecolin and damituricin, novel bioactive bromopyrrole alkaloids from the Mediterranean sponge Axinella damicornis.
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.
Aiello
Anna
A
Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli Federico II, via D Montesano 49, Napoli, Italy.
Fattorusso
Ernesto
E
Giordano
Antonella
A
Menna
Marialuisa
M
Müller
Werner E G
WE
Perović-Ottstadt
Sanja
S
Schröder
Heinz C
HC
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
D000470:Alkaloids; D011758:Pyrroles; C523025:damipipecolin; C523026:damituricin; D018698:Glutamic Acid; D016202:N-Methylaspartate; D001966:Bromine; D002118:Calcium