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The tropical marine sponge Dysidea herbacea (Keller) contains the filamentous unicellular cyanobacterium Oscillatoria spongeliae (Schulze) Hauck as an endosymbiont, plus numerous bacteria, both intracellular and extracellular. Archaeocytes and choanocytes are the major sponge cell types present. Density gradient centrifugation of glutaraldehyde-fixed cells with Percoll as the support medium has been used to separate the cyanobacterial symbiont from the sponge cells on the basis of their differing densities. The protocol also has the advantage of separating broken from intact cells of O. spongeliae. The lighter cell preparations contain archaeocytes and choanocytes together with damaged cyanobacterial cells, whereas heavier cell preparations contain intact cyanobacterial cells, with less than 1% contamination by sponge cells. Gas chromatography/mass spectrometry analysis has revealed that the terpene spirodysin is concentrated in preparations containing archaeocytes and choanocytes, whereas nuclear magnetic resonance analysis of the symbiont cell preparations has shown that they usually contain the chlorinated diketopiperazines, dihydrodysamide C and didechlorodihydrodysamide C, which are the characteristic metabolites of the sponge/symbiont association. However, one symbiont preparation, partitioned by a second Percoll gradient, has been found to be devoid of chlorinated diketopiperazines. The capability to synthesize secondary metabolites may depend on the physiological state of the symbiont; alternatively, there may be two closely related cyanobacterial strains within the sponge tissue.

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Chemical investigations of Cadlinaluteomarginata skin extracts, egg masses, and dietary sponges have led to the identification of the novel terpenoids cadlinaldehyde (30), spongian 32, seco-spongian 35, 20-acetoxy-12-marginatone (38), and lutenolide (39) from the nudibranch skin extracts, the new drimane sesquiterpenoid 1α,2α-diacetoxyalbicanyl acetate (40) from the nudibranch's egg mass, and the new sesquiterpenoids O-methyl-9-oxofurodysininlactone (47), 2-oxomicro-cionin-2-lactone (48), and O-methyl-2-oxomicrocionin-2-lactone (49), from the dietary sponge Pleraplysilla sp. The known terpenoids furodysinin (1), furodysin (16), marginatafuran (21), and 9,11-dihydrogracillin A (37), which have been frequently isolated from C. luteomarginata skin extracts, were found for the first time in extracts of the dietary sponges Pleraplysilla sp. and Aplysilla sp. One of the new terpenoids, cadlinaldehyde (30), has an unprecedented degraded sesterterpenoid skeleton. Keywords: nudibranch, sponge, terpenoids, structure elucidation.