Application of HPLC-NMR for the rapid chemical profiling of a Southern Australian sponge, Dactylospongia sp.
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.
Dias
Daniel Anthony
DA
School of Applied Sciences (Discipline of Applied Chemistry), RMIT University, Melbourne, Victoria, Australia.
Urban
Sylvia
S
D000818:Animals; D001315:Australia; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D051379:Mice; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013997:Time Factors