New terpenoid metabolites from the skin extracts, an egg mass, and dietary sponges of the Northeastern Pacific dorid nudibranch Cadlinaluteomarginata

Authors:
  • EDEric J. Dumdei
    Eric J. Dumdei
  • JKJulia Kubanek
    Julia Kubanek
  • JCJohn E. Coleman
    John E. Coleman
  • JPJana Pika
    Jana Pika
  • RARaymond J. Andersen
    Raymond J. Andersen
  • JSJorge Rios Steiner
    Jorge Rios Steiner
  • JCJon Clardy
    Jon Clardy
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Abstract
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.