3-Alkylpyridinium salts from Haplosclerida marine sponges: Isolation, structure elucidations, and biosynthetic considerations

Laville, Rémi; Amade, Philippe; Thomas, Olivier P.

doi:10.1351/PAC-CON-08-11-14

Pure Appl. Chem., 2009, Vol. 81, No. 6, pp. 1033-1040

http://dx.doi.org/10.1351/PAC-CON-08-11-14

Published online 2009-04-24

3-Alkylpyridinium salts from Haplosclerida marine sponges: Isolation, structure elucidations, and biosynthetic considerations

Rémi Laville, Philippe Amade and Olivier P. Thomas*

Université de Nice-Sophia Antipolis, Laboratoire de Chimie des Molécules Bioactives et des Arômes, UMR 6001 CNRS, Faculté des Sciences, 28 Avenue Valrose, F-06108 Nice Cedex 2, France

Abstract: A very little studied marine sponge Callyspongia sp. collected off the coast of Martinique was chemically investigated. The study led to the isolation and structure characterization of two new 3-alkylpyridinium salts which belonged to the recently isolated pachychaline family. Structures were elucidated by 1D, 2D NMR and detailed high-resolution electron spray ionization mass spectra (HRESIMS)-MS studies. The use of HRESIMS-MS studies proved to be highly efficient to identify two other close derivatives in a mixture. Finally, these studies allowed us to propose a general biosynthetic pathway leading to important 3-alkylpyridinium salts.