An Aminopyrimidone and Aminoimidazoles Alkaloids from the Rodrigues Calcareous Marine Sponge Ernsta naturalis

• Published in: Marine drugs 2022-10, Vol.20 (10), p.637
• Main Authors: Campos, Pierre-Eric, Herbette, Gaëtan, Fougère, Laetitia, Clerc, Patricia, Tintillier, Florent, de Voogd, Nicole J, Le Goff, Géraldine, Ouazzani, Jamal, Gauvin-Bialecki, Anne
• Format: Article
• Language: English
• Subjects: Alkaloids; Alkaloids - chemistry; aminoimidazolones alkaloids; aminopyrimidone alkaloid; Analytical chemistry; Animals; Carbon; Chemical Sciences; Clusters; Dichloromethane; Ernsta naturalis; Marine invertebrates; marine sponge; Metabolomics; molecular network; Molecular Structure; Networking; NMR; Nuclear magnetic resonance; Phenols; Porifera - chemistry; Spectra; Symmetry; Tandem Mass Spectrometry; Thymidine; Two dimensional analysis
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md20100637

A chemical study of the CH Cl -MeOH (1:1) extract from the sponge collected in Rodrigues (Mauritius) based on a molecular networking dereplication strategy highlighted one novel aminopyrimidone alkaloid compound, ernstine A ( ), seven new aminoimidazole alkaloid compounds, phorbatopsins D-E ( , ), calcaridine C ( ), naamines H-I ( , ), naamidines J-K ( , ), along with the known thymidine ( ). Their structures were established by spectroscopic analysis (1D and 2D NMR spectra and HRESIMS data). To improve the investigation of this unstudied calcareous marine sponge, a metabolomic study by molecular networking was conducted. The isolated molecules are distributed in two clusters of interest. Naamine and naamidine derivatives are grouped together with ernstine in the first cluster of twenty-three molecules. Phorbatopsin derivatives and calcaridine C are grouped together in a cluster of twenty-one molecules. Interpretation of the MS/MS spectra of other compounds of these clusters with structural features close to the isolated ones allowed us to propose a structural hypothesis for 16 compounds, 5 known and 11 potentially new.