Antiprotozoal Steroidal Saponins from the Marine SpongePandaros acanthifolium

Regalado, E.L., Tasdemir, D., Kaiser, M., Cachet, N., Amade, P. and Thomas, O.P. (2010) Antiprotozoal Steroidal Saponins from the Marine SpongePandaros acanthifolium. Journal of Natural Products, 73 (8). pp. 1404-1410. 10.1021/np100348x.

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DOI: 10.1021/np100348x

Abstract

The chemical composition of the Caribbean sponge Pandaros acanthifolium was reinvestigated and led to the isolation of 12 new steroidal glycosides, namely, pandarosides E-J (1-6) and their methyl esters (7-12). Their structures were determined on the basis of extensive spectroscopic analyses, including two-dimensional NMR and HRESIMS data. Like the previously isolated pandarosides A-D (13-16), the new compounds 1-12 share an unusual oxidized D-ring and a cis C/D ring junction. The absolute configurations of the aglycones were assigned by interpretation of CD spectra, whereas the absolute configurations of the monosaccharide units were determined by chiral GC analyses of the acid methanolysates. The majority of the metabolites showed in vitro activity against three or four parasitic protozoa. Particularly active were the compounds 3 (pandaroside G) and its methyl ester (9), which potently inhibited the growth of Trypanosoma brucei rhodesiense (IC50 values 0.78 and 0.038 μM, respectively) and Leishmania donovani (IC50's 1.3 and 0.051 μM, respectively).

Item Type:Article
Departments, units and centres:Department of Pharmaceutical and Biological Chemistry > Department of Pharmaceutical and Biological Chemistry
ID Code:2955
Journal or Publication Title:Journal of Natural Products
Deposited By:Library Staff
Deposited On:09 Mar 2012 17:03
Last Modified:09 Mar 2012 17:03

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