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EnglishThe structural peculiarity of saraines A, B and C, wherein a zwitterionic-like form is present due to the coordination of a nitrogen atom to the C-2 aldehyde by a strong proximity effect, has been further extended by experimental and theoretical evidences. They include the detection of [2M + H]+ clusters in electrospray ionization mass spectrometry in the positive ion mode of a water/acetonitrile solution, whereas only signals corresponding to [M + H]+ ions are detectable after addition of trifluoroacetic acid to the same solution. The zwitterionic form can be trapped to give O-methyl derivatives only by reaction with a strong alkylating agent such as Meerwein's reagent. DFT calculations carried out on the core structural model suggest that the nucleophilic N-1 atom in the minimized conformation is at a suitable distance from the carbonyl group and also defines an approach angle in good agreement with the Bürgi-Dunitz model. Antibacterial and hemolytic activities and inhibition of acetylcholinesterase (AChE) assays have been evaluated for saraines A-C in comparison to those of saraines 1-3 and isosaraine 1, all the metabolites isolated from the sponge Reniera (Haliclona) sarai collected in the Northern Adriatic sea
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| Titolo: | New structural insights into saraines A, B and C, macrocyclic alkaloids from the mediterranean sponge Reniera (Haliclona) sarai |
| Autori: | Defant, Andrea; Mancini, Ines; L., Raspor; Guella, Graziano; T., Turk; K., Sepcic |
| Autori Unitn: | |
| Titolo del periodico: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
| Anno di pubblicazione: | 2011 |
| Codice identificativo Scopus: | 2-s2.0-79960317854 |
| Codice identificativo ISI: | WOS:000293440900023 |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/ejoc.201100434 |
| Handle: | http://hdl.handle.net/11572/88118 |
| Appare nelle tipologie: | 03.1 Articolo su rivista (Journal article) |
File in questo prodotto:
| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| EJOC2011saraines.pdf | Versione editoriale (Publisher’s layout) | Tutti i diritti riservati (All rights reserved) | Administrator |
http://hdl.handle.net/11572/88118
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