Journal of Chemical Ecology

, Volume 6, Issue 1, pp 57–70

Alarm pheromones from the marine opisthobranchNavanax inermis

  • Howard L. Sleeper
  • Valerie J. Paul
  • William Fenical


When molested, the marine opisthobranchNavanax inermis secretes into its slime trail, a bright yellow mixture of three major compounds and several closely related minor substances. Collectively, these compounds induce an avoidance-alarm response in a trail-followingNavanax at the concentration limits of 1 × 10−5 M. The three major compounds have been isolated and identified as 10-(3′-pyridyl)-3E,5E,7E,9E-decatetraen-2-one (navenone A), 10-phenyl-3E,5E,7E,9E-decatetraen-2-one (navenone B) and 10-(4′-hydroxyphenyl)-3E,5E,7E,9E-decatetraen-2-one (navenone C). The minor constituents of the mixture are proposed as the 3Z,5Z,7E,9E-isomers and the 3-methyl homologs of navenones A and B. The navenones appear to be produced in a specialized gland referred to in earlier studies as the “yellow gland” and to communicate the presence of predators within the species.

Key words

Navanax inermis (syn.Chelidonura inermismarine-alarm pheromones navenones A-C chemical defense 


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Copyright information

© Plenum Publishing Corporation 1980

Authors and Affiliations

  • Howard L. Sleeper
    • 1
  • Valerie J. Paul
    • 1
  • William Fenical
    • 1
  1. 1.Institute of Marine ResourcesScripps Institution of OceanographyLa Jolla

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