Constituents of the sponge Thorecta reticulata

Cambie, R. C.; Lal, Allick R.; Rutledge, P. S.; Wellington, Keri D.

doi:10.1016/s0305-1978(00)00034-x

Cited by 1 publication

(4 citation statements)

References 9 publications

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“…As a result of that re-isolation of 5, it was found that the NMR data was identical to that previously reported by Capon and co-workers [23,24]. However, Cambie et al [23,24] showed that the signals of a terminal methyl group and the terminal olefinic proton in the 1 H NMR spectrum of 5 were incorrectly assigned on the basis of a COSY NMR experiment. In the original assignment by Capon and co-workers [23] the terminal methyl group was assigned at d (ppm) = 1.75 and the terminal olefinic proton was assigned at d (ppm) = 5.30 [23].…”

Section: Resultssupporting

confidence: 76%

“…In this way the proton chemical shifts for 5 were assigned but the carbon chemical shifts remained unassigned. In 2001, 5 was also isolated and reported from the sponge Thorecta reticulata, collected from the Kaikoura Peninsula, New Zealand [24]. As a result of that re-isolation of 5, it was found that the NMR data was identical to that previously reported by Capon and co-workers [23,24].…”

Section: Resultssupporting

confidence: 61%

“…In 2001, 5 was also isolated and reported from the sponge Thorecta reticulata, collected from the Kaikoura Peninsula, New Zealand [24]. As a result of that re-isolation of 5, it was found that the NMR data was identical to that previously reported by Capon and co-workers [23,24]. However, Cambie et al [23,24] showed that the signals of a terminal methyl group and the terminal olefinic proton in the 1 H NMR spectrum of 5 were incorrectly assigned on the basis of a COSY NMR experiment.…”

Section: Resultsmentioning

confidence: 99%

“…In the original assignment by Capon and co-workers [23] the terminal methyl group was assigned at d (ppm) = 1.75 and the terminal olefinic proton was assigned at d (ppm) = 5.30 [23]. Cambie et al [24] re-assigned the terminal methyl group to d (ppm) = 1.60 and the terminal olefinic proton to d (ppm) = 5.11, respectively, which is in full agreement with our 2-D COSY observations. As a result of our study, we are able to report the first complete assignment of the Signals overlapped.…”

Section: Resultsmentioning

confidence: 99%

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Application of HPLC‐NMR for the Rapid Chemical Profiling of a Southern Australian Sponge, Dactylospongia sp.

Dias

Urban²

2009

J of Separation Science

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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.

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