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Njaoaminiums A, B, and C: Cyclic 3-Alkylpyridinium Salts from the Marine Sponge Reniera sp.
Laboratoire de Chimie des Molécules Bioactives et des Arômes, Institut de Chimie de Nice, Faculté des Science, Université de Nice-Sophia Antipolis, UMR 6001 CNRS, Parc Valrose, 06108 Nice Cedex 02, France
Medicinal Chemistry Department, PharmaMar S.A., Pol. Ind. La Mina Norte, Avenida de los Reyes 1, 28770 (Colmenar Viejo) Madrid, Spain
* Authors to whom correspondence should be addressed.
Received: 9 October 2009; in revised form: 3 November 2009 / Accepted: 17 November 2009 / Published: 19 November 2009
Abstract: Three novel cyclic 3-alkylpyridinium salts, named njaoaminiums A, B, and C (1-3), were isolated from the marine sponge Reniera sp., collected off the coasts of Pemba Island, Tanzania. The structural determination of the compounds was based on 1D and 2D NMR studies and mass spectral determinations. Njaoaminiums B (2) and C (3) are the first examples of cyclic 3-alkylpyridinium salts bearing a methyl substituent on the alkyl chains. These compounds are assumed to be biosynthetic precursors of the njaoamines, previously isolated from the same sponge. The absolute configurations of the methyls of 2 and 3 were assigned by comparison between experimental and TDDFT calculated circular dichroism spectra on the most stable conformer. Compound 2 showed weak cytotoxicity against the three human tumor cell lines MDA-MB-231, A549, and HT29.
Keywords: marine natural products; marine sponge; Reniera; alkylpyridinium; circular dichroism; absolute configuration
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Laville, R.; Genta-Jouve, G.; Urda, C.; Fernández, R.; Thomas, O.P.; Reyes, F.; Amade, P. Njaoaminiums A, B, and C: Cyclic 3-Alkylpyridinium Salts from the Marine Sponge Reniera sp.. Molecules 2009, 14, 4716-4724.
Laville R, Genta-Jouve G, Urda C, Fernández R, Thomas OP, Reyes F, Amade P. Njaoaminiums A, B, and C: Cyclic 3-Alkylpyridinium Salts from the Marine Sponge Reniera sp.. Molecules. 2009; 14(11):4716-4724.
Laville, Remi; Genta-Jouve, Grégory; Urda, Carlos; Fernández, Rogelio; Thomas, Olivier P.; Reyes, Fernando; Amade, Philippe. 2009. "Njaoaminiums A, B, and C: Cyclic 3-Alkylpyridinium Salts from the Marine Sponge Reniera sp.." Molecules 14, no. 11: 4716-4724.