Application of HPLC-NMR for the rapid chemical profiling of a Southern Australian Sponge, Dactylospongia sp

Dias, D and Urban, S 2009, 'Application of HPLC-NMR for the rapid chemical profiling of a Southern Australian Sponge, Dactylospongia sp', Journal of Separation Science, vol. 32, no. 4, pp. 542-548.


Document type: Journal Article
Collection: Journal Articles

Title Application of HPLC-NMR for the rapid chemical profiling of a Southern Australian Sponge, Dactylospongia sp
Author(s) Dias, D
Urban, S
Year 2009
Journal name Journal of Separation Science
Volume number 32
Issue number 4
Start page 542
End page 548
Total pages 6
Publisher Wiley - VCH Verlag GmbH and Co. KGaA
Abstract Rapid chemical profiling of the antitumour active crude dichloromethane extract of the marine sponge, Dactylospongia sp. was undertaken. A combination of both offline (HPLC followed by NMR and MS) and on-line (on-flow and stop-flow HPLC-NMR) chemical profiling approaches was adopted to establish the exact nature of the major constituents present in the dichloromethane extract of this sponge. On-flow HPLC-NMR analysis was employed to initially identify components present in the dichloromethane extract, while stop-flow HPLC-NMR experiments were then conducted on the major component present, resulting in the partial identification of pentaprenylated p-quinol (5). Subsequent off-line RP semi-preparative HPLC isolation of 5 followed by detailed spectroscopic analysis using NMR and MS permitted the complete structure to be established. This included the first complete carbon NMR chemical shift assignment of 5 based on the heteronuclear 2-D NMR experiments, together with the first report of its antitumour activity. This study represents one of the few reports describing the application of HPLC-NMR to chemically profile secondary metabolites from a marine organism.
Subject Natural Products Chemistry
Keyword(s) biological activity
dereplication
HPLC-NMR
natural products
Pentaprenylated p-quinol
DOI - identifier 10.1002/jssc.200800548
Copyright notice © 2009 Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim.
ISSN 1615-9306
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