TY - JOUR
T1 - Njaoaminiums A, B, and C
T2 - Cyclic 3-alkylpyridinium salts from the marine sponge Reniera sp.
AU - Laville, Remi
AU - Genta-Jouve, Grégory
AU - Urda, Carlos
AU - Fernández, Rogelio
AU - Thomas, Olivier P.
AU - Reyes, Fernando
AU - Amade, Philippe
PY - 2009/11
Y1 - 2009/11
N2 - 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.
AB - 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.
KW - Absolute configuration
KW - Alkylpyridinium
KW - Circular dichroism
KW - Marine natural products
KW - Marine sponge
KW - Reniera
UR - http://www.scopus.com/inward/record.url?scp=73349116533&partnerID=8YFLogxK
U2 - 10.3390/molecules14114716
DO - 10.3390/molecules14114716
M3 - Article
SN - 1420-3049
VL - 14
SP - 4716
EP - 4724
JO - Molecules
JF - Molecules
IS - 11
ER -