Acanthifoliosides, minor steroidal saponins from the Caribbean sponge Pandaros acanthifolium

Regalado, E.L., Jiménez-Romero, C., Genta-Jouve, G., Tasdemir, D., Amade, P., Nogueiras, C. and Thomas, O.P. (2011) Acanthifoliosides, minor steroidal saponins from the Caribbean sponge Pandaros acanthifolium. Tetrahedron, 67 (5). pp. 1011-1018. 10.1016/j.tet.2010.11.103.

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DOI: 10.1016/j.tet.2010.11.103

Abstract

Seven novel steroid glycosides, acanthifoliosides A-F (1-6), and the methyl ester of 6 (7), were isolated from the marine sponge Pandaros acanthifolium as minor components. Acanthifoliosides are characterized by a rare C-15 and C-16 oxidized D ring, which was previously found in saponins produced by starfishes. Very uncommon is the presence of additional sugar residues at C-15 or C-16. Their structures were determined on the basis of extensive spectroscopic analyses, including two-dimensional NMR and HRESIMS data. The absolute configurations of the aglycones were assigned by comparison between experimental and TDDFT calculated CD spectra of 1, whereas the absolute configurations of the monosaccharide units were determined by chiral GC analyses of the acid methanolysates. Some of the acanthifoliosides exhibit moderate antiprotozoal activity but to a lesser extent than the most potent pandarosides.

Item Type:Article
Departments, units and centres:Department of Pharmaceutical and Biological Chemistry > Department of Pharmaceutical and Biological Chemistry
ID Code:2953
Journal or Publication Title:Tetrahedron
Deposited By:Library Staff
Deposited On:09 Mar 2012 16:39
Last Modified:09 Mar 2012 16:39

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