njaoaminiums a, b, and c cyclic 3-alkylpyridinium salts from the marine sponge reniera sp.njaoaminiums a、b和c循环3-alkylpyridinium盐从海军海绵reniera sp。.pdfVIP

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njaoaminiums a, b, and c cyclic 3-alkylpyridinium salts from the marine sponge reniera sp.njaoaminiums a、b和c循环3-alkylpyridinium盐从海军海绵reniera sp。.pdf

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njaoaminiums a, b, and c cyclic 3-alkylpyridinium salts from the marine sponge reniera sp.njaoaminiums a、b和c循环3-alkylpyridinium盐从海军海绵reniera sp。

Molecules 2009, 14, 4716-4724; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Njaoaminiums A, B, and C: Cyclic 3-Alkylpyridinium Salts from the Marine Sponge Reniera sp. Remi Laville 1, Grégory Genta-Jouve 1, Carlos Urda 2, Rogelio Fernández 2, Olivier P. Thomas 1,*, Fernando Reyes 2 and Philippe Amade 1,* 1 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 2 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; E-Mail: othomas@unice.fr (O.P.T.); amade@unice.fr (P.A.); Tel.: +33 492 076 134. Received: 9 October 2009; in revised form: 3 November / 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