title: Secondary metabolome and its defensive role in the aeolidoideanPhyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia).
abstract: Phyllodesmium longicirrumis the largest aeolidoidean species known to date, and extremely rich in terpenoid chemistry. Herein we report the isolation of a total of 19 secondary metabolites from a single specimen of this species, i.e., steroids1-4, cembranoid diterpenes5-13, complex biscembranoids14and15, and the chatancin-type diterpenes16-19. These compounds resemble those from soft corals of the genusSarcophyton, of which to date, however, onlyS. trocheliophorumis described as a food source forP. longicirrum. Fish feeding deterrent activity was determined using the tropical puffer fishCanthigaster solandri, and showed activity for (2S)-isosarcophytoxide (10), cembranoid bisepoxide12and 4-oxochatancin (16). Determining the metabolome ofP. longicirrumand its bioactivity, makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal.
authors.affiliation: Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
authors.forename: Alexander
authors.initials: A
authors.lastname: Bogdanov
authors.affiliation: Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
authors.forename: Cora
authors.initials: C
authors.lastname: Hertzer
authors.affiliation: Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Kehraus
authors.affiliation: Institute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, Germany.
authors.forename: Samuel
authors.initials: S
authors.lastname: Nietzer
authors.affiliation: Institute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, Germany.
authors.forename: Sven
authors.initials: S
authors.lastname: Rohde
authors.affiliation: Institute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, Germany.
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Schupp
authors.affiliation: Zoologisches Forschungsmuseum Alexander Koenig, Adenauerallee 160, 53113 Bonn, Germany.
authors.forename: Heike
authors.initials: H
authors.lastname: Wägele
authors.affiliation: Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
authors.forename: Gabriele M
authors.initials: GM
authors.lastname: König
keywords: Nudibranchia; Phyllodesmium longicirrum; chemical defense; chemoecology; natural compounds