Nukuhivensiums, Indolo[2,3-a]quinoliziniums from the Marquesan Plant Rauvolfia nukuhivensis 英文参考文献.docVIP

Molecules 2012, 17, 12015-12022; doi:10.3390/molecules171012015 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Nukuhivensiums, Indolo[2,3-a]quinoliziniums from the Marquesan Plant Rauvolfia nukuhivensis Nicolas J. Martin 1, Soizic Prado 2, Gael Lecellier 1, Olivier P. Thomas 3,* and Phila Raharivelomanana 1,* 1 EIMS Laboratory UMR 241 EIO, University of French Polynesia, 98702 Faaa, Tahiti, French Polynesia; E-Mails: Nicolas.martin@upf.pf (N.J.M.); Gael.lecellier@upf.pf (G.L.) 2 MCAM Laboratory UMR 7245 CNRS, National Museum of Natural History, 63 rue Buffon, 75005 Paris, France; E-Mail: Sprado@mnhn.fr 3 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; E-Mails: olivier.thomas@unice.fr (O.P.T.); phila.raharivelomanana@upf.pf (P.R.); Tel.: +33-04-9207-6134 (O.P.T.); Fax: +33-04-9207-6189 (O.P.T.); Tel.: +689-803-813 (P.R.); Fax: +689-803-804 (P.R.). 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  Molecules 2012, 17