Simplexidine, a 4-Alkylpyridinium Alkaloid from the Caribbean Sponge Plakortis simplex 英文参考文献.docVIP

Molecules 2008, 13, 1465-1471; DOI: 10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /molecules Article Simplexidine, a 4-Alkylpyridinium Alkaloid from the Caribbean Sponge Plakortis simplex Ernesto Fattorusso, Adriana Romano, Fernando Scala and Orazio Taglialatela-Scafati* Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli “Federico II”, Via D. Montesano 49, 80131 Napoli, Italy.; E-mails: fattoru@nina.it; adromano@unina.it; fernando.scala@unina.it * Author to whom correspondence should be addressed. Tel. +39-081678509; E-mail: scatagli@unina.it Received: 25 June 2008 / Accepted: 16 July 2008 / Published: 17 July 2008 Abstract: Chemical analysis of the secondary metabolites of the Caribbean sponge Plakortis simplex, a source of many bioactive compounds, showed the presence of the new metabolite simplexidine (4), belonging to the extremely rare class of 4-alkyl-pyridinium alkaloids. The structural characterization of this molecule, based on spectroscopic methods, is reported. Keywords: Simplexidin, alkaloids, pyridinium, Plakortis, NMR. Introduction As part of an ongoing search for biologically active compounds from marine invertebrates, our research group has been devoting considerable efforts to the chemical investigation of the Caribbean sponge Plakortis simplex. This research project, started about ten years ago, has been strongly fostered by the discovery of a large array of structurally unique and biologically active metabolites. This richness of secondary metabolite production has been discussed in a review paper [1] and has been recently correlated to the wide presence of bacterial and fungal symbionts associated to the sponge host cells [2]. For example, P. simplex provided a series of promising lead compounds for drug development, including the immunosuppressive glycolipids plakosides [3] and simplexides [4] and a series of  Mo