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Beilstein J Org Chem. 2017 Mar 13;13:502-519. doi: 10.3762/bjoc.13.50. eCollection 2017.

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia).

Author information

1
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
2
Institute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, Germany.
3
Zoologisches Forschungsmuseum Alexander Koenig, Adenauerallee 160, 53113 Bonn, Germany.

Abstract

Phyllodesmium longicirrum is 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., steroids 1-4, cembranoid diterpenes 5-13, complex biscembranoids 14 and 15, and the chatancin-type diterpenes 16-19. These compounds resemble those from soft corals of the genus Sarcophyton, of which to date, however, only S. trocheliophorum is described as a food source for P. longicirrum. Fish feeding deterrent activity was determined using the tropical puffer fish Canthigaster solandri, and showed activity for (2S)-isosarcophytoxide (10), cembranoid bisepoxide 12 and 4-oxochatancin (16). Determining the metabolome of P. longicirrum and its bioactivity, makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal.

KEYWORDS:

Nudibranchia; Phyllodesmium longicirrum; chemical defense; chemoecology; natural compounds

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