6533b85bfe1ef96bd12ba262

RESEARCH PRODUCT

Damipipecolin and damituricin, novel bioactive bromopyrrole alkaloids from the Mediterranean sponge Axinella damicornis

Werner E. G. M�llerSanja Perović-ottstadtHeinz C. SchröderAntonella GiordanoMarialuisa MennaErnesto FattorussoAnna Aiello

subject

N-MethylaspartateCell SurvivalStereochemistryClinical BiochemistryGlutamic AcidPharmaceutical ScienceBiochemistryNatural productchemistry.chemical_compoundAlkaloidsAxinellaBromopyrrole alkaloidDrug DiscoverySerotonin receptor activityAnimalsHumansOrganic chemistryPyrrolesMolecular BiologyCells CulturedPyrroleMarine spongeNeuronsMolecular StructurebiologyMediterranean RegionAlkaloidOrganic ChemistryAxinellaBiological activityGlutamic acidBrominebiology.organism_classificationRatsAxinella damicorniSpongechemistryMolecular MedicineSerotonin receptor activity.CalciumSuberitesSuberites

description

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.

yearjournalcountryeditionlanguage
2007-01-30Bioorganic & Medicinal Chemistry
https://doi.org/10.1016/j.bmc.2007.05.074