Journal of Chemical Ecology

, Volume 32, Issue 1, pp 97–123

Activated Chemical Defense in Aplysina Sponges Revisited


DOI: 10.1007/s10886-006-9355-x

Cite this article as:
Thoms, C., Ebel, R. & Proksch, P. J Chem Ecol (2006) 32: 97. doi:10.1007/s10886-006-9355-x


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 

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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