Journal of Chemical Ecology

, Volume 32, Issue 1, pp 97–123 | Cite as

Activated Chemical Defense in Aplysina Sponges Revisited

  • Carsten Thoms
  • Rainer Ebel
  • Peter Proksch


Sponges of the genus Aplysina accumulate brominated isoxazoline alkaloids in concentrations that sometimes exceed 10% of their dry weight. We previously reported a decrease in concentrations of these compounds and a concomitant increase in concentrations of the monocyclic nitrogenous compounds aeroplysinin-1 and dienone in Aplysina aerophoba following injury of the sponge tissue. Further investigations indicated a wound-induced enzymatic cleavage of the former compounds into the latter, and demonstrated that these reactions also occur in other Aplysina sponges. A recent study on Caribbean Aplysina species, however, introduced doubt regarding the presence of a wound-induced bioconversion in sponges of this genus. This discrepancy motivated us to reinvestigate carefully the fate of brominated alkaloids in A. aerophoba and in other Aplysina sponges following mechanical injury. As a result of this study we conclude that (1) tissue damage induces a bioconversion of isoxazoline alkaloids into aeroplysinin-1 and dienone in Aplysina sponges, (2) this reaction is likely catalyzed by enzymes, and (3) it may be ecologically relevant as the bioconversion products possibly protect the wounded sponge tissue from invasion of bacterial pathogens.

Key Words

Wound-induced bioconversion chemical defense biotransformation brominated alkaloids enzymatic cleavage marine sponge 



We acknowledge Prof. Werner E.G. Müller, Prof. Renato Batel, and the staff of the Ruder Boscovic Center for Marine Research for assistance during organization of sample collections and laboratory work at Rovinj, Croatia. We also thank Sabine Borstel for help in isolating the sponge metabolites and Arno Kunze for samples from Caribbean Aplysina sponges. Carsten Thoms acknowledges support with a Fedodor Lynen Fellowship from the Alexander von Humboldt Foundation, Bonn. This work was supported by the Bundesministerium für Bildung und Forschung (project: Center of Excellence BIOTECmarin). Finally, we thank two anonymous referees who helped to improve this manuscript.


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Copyright information

© Springer Science + Business Media, Inc. 2006

Authors and Affiliations

  1. 1.Institut für Pharmazeutische BiologieUniversität DüsseldorfDüsseldorfGermany
  2. 2.University of Guam Marine LaboratoryMangilaoUSA

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