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Issue 35, 2017
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Volatiles from the fungal microbiome of the marine sponge Callyspongia cf. flammea

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Abstract

The volatiles emitted by five fungal strains previously isolated from the marine sponge Callyspongia cf. flammea were captured with a closed-loop stripping apparatus (CLSA) and analyzed by GC-MS. Besides several widespread compounds, a series of metabolites with interesting bioactivities were found, including the quorum sensing inhibitor protoanemonin, the fungal phytotoxin 3,4-dimethylpentan-4-olide, and the insect attractant 1,2,4-trimethoxybenzene. In addition, the aromatic polyketides isotorquatone and chartabomone that are both known from Eucalyptus and a new O-desmethyl derivative were identified. The biosynthesis of isotorquatone was studied by feeding experiments with isotopically labeled precursors and its absolute configuration was determined by enantioselective synthesis of a reference compound. Bioactivity testings showed algicidal activity for some of the identified compounds, suggesting a potential ecological function in sponge defence.

Graphical abstract: Volatiles from the fungal microbiome of the marine sponge Callyspongia cf. flammea

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Supplementary files

Article information


Submitted
25 Jul 2017
Accepted
30 Aug 2017
First published
05 Sep 2017

Org. Biomol. Chem., 2017,15, 7411-7421
Article type
Paper

Volatiles from the fungal microbiome of the marine sponge Callyspongia cf. flammea

L. Barra, P. Barac, G. M. König, M. Crüsemann and J. S. Dickschat, Org. Biomol. Chem., 2017, 15, 7411
DOI: 10.1039/C7OB01837A

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