Marine isocyano compounds

Chemical Defenses: From Compounds to Communities

“…Since then more than 150 isocyano terpenes have been structurally characterized; these are predominantly sesquiterpenes and diterpenes with at least one nitrogen that forms a cyanide functional group. The diversity of marine isocyano terpene structures has been reviewed (Edenborough and Herbert, 1988;Chang and Scheuer, 1993;Chang, 2000;Garson and Simpson, 2004), and here we briefly also discuss the structurally related isothiocyanates and formamides. Isocyano terpenes are found in a variety of organisms, including fungi, bacteria, cyanobacteria, sponges, and nudibranchs; however, for the purpose of this review, we focus on the compounds isolated from marine sponges and nudibranchs.…”

“…Phyllidiid nudibranchs can be brightly colored (aposematic coloration), and many of them contain isocyanide compounds (Fusetani et al, 1990a(Fusetani et al, , 1991, often the same isocyano terpenes as their prey sponges, suggesting a trophic transfer of these compounds (Chang and Scheuer, 1993;Avila, 1995;Garson et al, 2000). On Guam, Phyllidiella granulatus was observed feeding on the sponge Acanthella cavernosa, and both the nudibranch and its mucus contained the same isocyano diterpenes as the sponge (Ritson-Williams and Paul, 2007).…”

Marine benthic invertebrates use multimodal cues for defense against reef fish

“…1). Other studies have found isocyanide and isothiocyanate compounds in various species of phyllidiid nudibranchs and their host sponges (Chang & Scheuer 1993, Dumdei et al 1997. These compounds are toxic to some animals (Johannes 1963, Gunthorpe & Cameron 1987 and are components of the crude extracts that were deterrent in this study.…”

“…All 6 individual P. granulatus found feeding on A. cavernosa had similar GC-MS traces as their dietary sponge, but here we present only 1 example for clarity. The extracts contained kalihinol A and C (peaks at 25.9 and 22.8 min, respectively), 2 di-isocyano diterpenes previously isolated and characterized from Acanthella cavernosa , and a sesquiterpene isocyanide compound (peak at 12.4 min) with a mass spectrum indicating similarity to the epimaaliane series isolated from the sponge Axinella cannabina (Chang & Scheuer 1993). Individual A. cavernosa extract yields ranged from 0.7 to 6% of the sponge dry weight.…”

“…Most phyllidiid nudibranchs have contrasting color patterns, and many species (although most remain untested) sequester isocyanide terpenes and related compounds from their host sponges (Chang & Scheuer 1993, Dumdei et al 1997. Most phyllidiid species are uncommon on Guam, but we collected enough individuals of Phyllidia elegans and Phyllidiella pustulosa from Guam and Phyllidia varicosa and Phyllidiella pustulosa from Palau for replicated feeding assays.…”