Title
New 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrimidinium alkaloids (phloeodictynes) from the New Caledonian shallow-water haplosclerid sponge Oceanapia fistulosa. Structural elucidation from mainly LC-tandem-MS-soft-ionization techniques and discovery of antiplasmodial activity
Date Issued
07 March 2004
Access level
metadata only access
Resource Type
journal article
Author(s)
Mancini I.
Guella G.
Debitus C.
Duigou A.G.
Ausseil F.
Menou J.L.
Pietra F.
Universidad Paul Sabatier
Abstract
We report here on new 6-hydroxy-l,2,3,4-tetrahydropyrrolo[l,2-a]pyrimidinium alkaloids, belonging to the phloeodictyne family, isolated from the haplosclerid sponge Oceanapia [= Phloeodictyon] fistulosa (Browerbank, 1873) from New Caledonian shallow waters. Online LC-ESI-MS analysis, coupled to tandem fragmentation experiments on the crude alkaloid mixture, allowed us to clarify their flat structures, including structural isomers. At least 25 different components, of which 17 are new members with variable terminus and length chains, were characterised, besides less abundant analogues bearing a thioethylguanidine side chain. Crude mixtures and HPLC enriched fractions proved active against chloroquine-resistant Plasmodiumfalciparum, with IC50 values ranging from 0.6 to 6 μM, while cytotoxicity against human A-549 cell line was low. This makes these alkaloids a good prospect as leads for novel antimalarial agents.
Start page
783
End page
787
Volume
2
Issue
5
Language
English
OCDE Knowledge area
Bioquímica, Biología molecular Química orgánica
Scopus EID
2-s2.0-1642325822
PubMed ID
Source
Organic and Biomolecular Chemistry
ISSN of the container
14770520
Sources of information: Directorio de Producción Científica Scopus