Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii,a Mutualistic Fungus of French Guiana Termites |
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Authors: | Jonathan Sorres,Té o Hebra,Nicolas Elie,Charlotte Leman-Loubiè re,Tatyana Grayfer,Philippe Grellier,David Touboul,Didier Stien,Vé ronique Eparvier |
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Affiliation: | 1.CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, Université Paris-Saclay, 91198 Gif-sur-Yvette, France; (T.H.); (N.E.); (C.L.-L.); (T.G.); (D.T.);2.CNRS, Département RDDM, UMR 7245, Muséum National d’Histoire Naturelle CP52, 57 Rue Cuvier, 75005 Paris, France;3.Laboratoire de Biodiversité et Biotechnologie Microbiennes, CNRS, Sorbonne Université, Observatoire Océanologique, 66650 Banyuls-sur-Mer, France; |
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Abstract: | Social insects are in mutualism with microorganisms, contributing to their resistance against infectious diseases. The fungus Pseudallescheria boydii SNB-CN85 isolated from termites produces ovalicin derivatives resulting from the esterification of the less hindered site of the ovalicin epoxide by long-chain fatty acids. Their structures were elucidated using spectroscopic analysis and semisynthesis from ovalicin. For ovalicin, these compounds displayed antiprotozoal activities against Plasmodium falciparum and Trypanosoma brucei, with IC50 values of 19.8 and 1.1 µM, respectively, for the most active compound, i.e., ovalicin linoleate. In parallel, metabolomic profiling of a collection of P. boydii strains associated with termites made it possible to highlight this class of compounds together with tyroscherin derivatives in all strains. Finally, the complete genome of P. boydii strains was obtained by sequencing, and the cluster of potential ovalicin and ovalicin biosynthesis genes was annotated. Through these metabolomic and genomic analyses, a new ovalicin derivative named boyden C, in which the 6-membered ring of ovalicin was opened by oxidative cleavage, was isolated and structurally characterized. |
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Keywords: | Pseudallescheria boydii ovalicin molecular networking symbiotic fungus genome biosynthesis |
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