Steroidal glycosides from the marine sponge Pandaros acanthifolium |
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Authors: | Nadja Cachet,Erik L. Regalado,Gré gory Genta-Jouve,Philippe Amade |
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Affiliation: | a Laboratoire de Chimie des Molécules Bioactives et des Arômes UMR 6001 CNRS, University of Nice-Sophia Antipolis, Faculté des Sciences Parc Valrose, 06108 Nice Cedex 2, France b Department of Chemistry, Center of Marine Bioproducts, Loma y 37 Alturas del Vedado, C.P. 10400 Havana, Cuba |
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Abstract: | The chemical composition of the Caribbean sponge Pandaros acanthifolium was investigated and led to the isolation of seven new steroidal glycosides namely pandarosides A-D (1, 3, 4 and 6) along with the three methyl esters of pandarosides A, C, and D (2, 5 and 7). Their structures were characterized as 3β-[β-glucopyranosyl-(1→2)-β-glucopyranosyloxyuronic acid]-16-hydroxy-5α,14β-poriferast-16-ene-15,23-dione (1) and its methyl ester (2), 3β-[β-glucopyranosyloxyuronic acid]-16-hydroxy-5α,14β-poriferast-16-ene-15,23-dione (3), 3β-[β-glucopyranosyl-(1→2)-β-glucopyranosyloxyuronic acid]-16-hydroxy-5α,14β-cholest-16-ene-15,23-dione (4) and its methyl ester (5), 3β-(β-glucopyranosyloxyuronic acid)-16-hydroxy-5α,14β-cholest-16-ene-15,23-dione (6) and its methyl ester (7) on the basis of detailed spectroscopic analyses, including 2D NMR and HRESIMS studies. Pandarosides A-D and their methyl esters (1-7) are all characterized by a rare 2-hydroxycyclopentenone D-ring with a 14β configuration. The absolute configuration of the aglycon part of pandaroside A (1) was assigned by comparison between experimental and TDDFT calculated circular dichroism spectra on the more stable conformer. |
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Keywords: | Marine sponge Pandaros Steroidal glycosides Structure elucidation Stereochemistry |
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