Three novel tetraphenolic bis-spiroketals, prunolides A-C (1, 3, and 4) have been isolated from the Australian ascidian Synoicum prunum. The structures were determined from NMR spectroscopic data and from an X-ray analysis of prunolide A. The prunolides contain a unique 1,6,8-trioxadispiro[4.1.4.2]trideca-3,10,12-triene-2,9-dione carbon skeleton. The known compound rubrolide A (5) was also isolated.

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A robust method was developed to cluster similar NMR spectra from partially purified extracts obtained from a range of marine sponges and a plant biota. The NMR data were acquired using microtiter plate NMR (VAST) in protonated solvents. A sample data set which contained several clusters was used to optimize the protocol. The evaluation of the robustness was performed using three different clustering methods: tree clustering analysis, K-means clustering and multidimensional scaling. These methods were compared for consistency using the sample data set and the optimized methodology was applied to clustering of a set of spectra from partially purified biota extracts.

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