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Nukuhivensiums, Indolo[2,3-a]quinoliziniums from the Marquesan Plant Rauvolfia nukuhivensis
Laboratory UMR 241 EIO, University of French Polynesia, 98702 Faa'a, Tahiti, French Polynesia
Laboratory UMR 7245 CNRS, National Museum of Natural History, 63 rue Buffon, 75005 Paris, France
Nice Institute of Chemistry UMR 7272 CNRS-PCRE, University of Nice-Sophia Antipolis, Parc Valrose, 06108 Nice, France
* Authors to whom correspondence should be addressed.
Received: 13 September 2012; in revised form: 7 October 2012 / Accepted: 9 October 2012 / Published: 12 October 2012
Abstract: The first phytochemical inspection of the Marquesan endemic plant Rauvolfia nukuhivensis led to the isolation and structure characterization of two new indolo[2,3‑a]quinolizinium derivatives named nukuhivensium (1) and N12-methyl-nukuhivensium (2). They feature an aromatic indolo[2,3-a]quinolizinium core, substituted at C-2 by a n-propyl group, which is unusual in this family of alkaloid derivatives. The structure elucidation was performed on the basis of NMR spectroscopy and especially by interpretation of 2D HMBC correlations. A biosynthetic pathway is proposed on the basis of known enzymatic transformations for this family of natural products. These compounds exhibited low antimicrobial activities.
Keywords: alkaloid; Rauvolfia; antimicrobial; indoles; biosynthesis
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MDPI and ACS Style
Martin, N.J.; Prado, S.; Lecellier, G.; Thomas, O.P.; Raharivelomanana, P. Nukuhivensiums, Indolo[2,3-a]quinoliziniums from the Marquesan Plant Rauvolfia nukuhivensis. Molecules 2012, 17, 12015-12022.
Martin NJ, Prado S, Lecellier G, Thomas OP, Raharivelomanana P. Nukuhivensiums, Indolo[2,3-a]quinoliziniums from the Marquesan Plant Rauvolfia nukuhivensis. Molecules. 2012; 17(10):12015-12022.
Martin, Nicolas J.; Prado, Soizic; Lecellier, Gael; Thomas, Olivier P.; Raharivelomanana, Phila. 2012. "Nukuhivensiums, Indolo[2,3-a]quinoliziniums from the Marquesan Plant Rauvolfia nukuhivensis." Molecules 17, no. 10: 12015-12022.