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      Ulososides and Urabosides — Triterpenoid Saponins from the Caribbean Marine Sponge Ectyoplasia ferox

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          Abstract

          Three new triterpene glycosides, named ulososide F ( 1), urabosides A ( 2) and B ( 3), together with the previously reported ulososide A ( 4), were isolated from the Caribbean marine sponge Ectyoplasia ferox. Their structures were elucidated using extensive interpretation of 1D and 2D-NMR data, as well as HRESIMS. The aglycon of all compounds is a rare 30-norlonastane and the sugar residues were identified after acid hydrolysis and GC analyses. Cytotoxicities of the isolated compounds were evaluated against Jurkat and CHO cell lines by a MTT in vitro assay as well as a hemolysis assay. Unexpectedly, all these saponin derivatives showed very low activity in our bioassays.

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          Most cited references30

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          Marine natural products.

          Covering: 2010. Previous review: Nat. Prod. Rep., 2011, 28, 196. This review covers the literature published in 2010 for marine natural products, with 895 citations (590 for the period January to December 2010) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1003 for 2010), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.
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            NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides.

            The potential of one- and two-dimensional NMR techniques for the identification of individual sugar residues, their anomeric configuration, interglycosidic linkages, sequencing and the site of any appended group, in establishing the structures of naturally occurring oligosaccharides and glycosides is presented.
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              Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations.

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                Author and article information

                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                27 February 2013
                March 2013
                : 18
                : 3
                : 2598-2610
                Affiliations
                [1 ]Grupo de Investigación Productos Naturales Marinos, Facultad de Química Farmacéutica, Universidad de Antioquia, A.A 1226, Medellín, Colombia; E-Mails: dmarquez@ 123456farmacia.udea.edu.co (D.M.); amart@ 123456farmacia.udea.edu.co (A.M.)
                [2 ]Unidad de Investigación e Innovación, Humax Pharmaceutical S.A. Itagüí, Colombia
                [3 ]Grupo de Biotecnología Animal, Universidad Nacional de Colombia, Medellín, Colombia; E-Mails: ingbiodianacaro@ 123456gmail.com (D.M.); memarque@ 123456unal.edu.co (M.E.M.); jblopez@ 123456unal.edu.co (J.L.)
                [4 ]Nice Institute of Chemistry – PCRE, UMR 7272 CNRS, University of Nice Sophia-Antipolis, Faculté des Sciences, Parc Valrose 06108 Nice, France
                Author notes
                [* ] Authors to whom correspondence should be addressed; E-Mails: jhonnycolorado@ 123456humax.com.co (J.C.); olivier.thomas@ 123456unice.fr (O.P.T.); Tel.: +57-4-377-07-43 (J.C.); Fax: +57-4-372-12-40 (J.C.); Tel.: +33-492-076-134 (O.P.T.); Fax: +33-492-076-189 (O.P.T.).
                Article
                molecules-18-02598
                10.3390/molecules18032598
                6270507
                23446917
                c2ad1238-3ae1-45ff-a15c-a49f127a139c
                © 2013 by the authors; licensee MDPI, Basel, Switzerland.

                This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                : 21 January 2013
                : 07 February 2013
                : 18 February 2013
                Categories
                Article

                ectyoplasia ferox,marine sponge,saponins,urabosides,ulososides

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