Natural Product Communications 2019; 14(1) 63 - 66
Fungus-Growing Ant’s Microbial Interaction of Streptomyces sp. and
Escovopsis sp. through Molecular Networking and MALDI Imaging
Cristopher A. Boya P., Martin H. Christian, Hermógenes Fernández-Marín, Marcelino Gutiérrez.
Microbes associated with fungus-growing ants represent a poorly explored source of natural products. In this study, we used mass spectrometry-based dereplication techniques for identifying a set of secondary metabolites produced during the microbial interaction between Streptomyces sp. (CB0028) and Escovopsis sp. (CBAcro424). Both microorganisms were isolated from the nest of the fungus-growing ant Acromyrmex echinatior. Through MALDI imaging and MS/MS molecular networking, we annotated the siderophores: desferrioxamine B (1), ferrioxamine B (2), ferrioxamine E (3) and the N-formylated peptide SCO-2138/SLI-2138 (4). MALDI imaging experiments suggest that siderophores occurred during the microbial interactions in the fungus-growing ants – microbes symbioses. This is the first report on the production of compounds 1-4 by bacteria associated with fungus-growing ants.
Preprint submitted on 07.08.2019, 10:27 and posted on 08.08.2019, 14:42
Reproducible Molecular Networking Of Untargeted Mass Spectrometry Data Using GNPS.
Allegra T. Aron Emily Gentry Kerry L. McPhail Louis Felix Nothias Mélissa Nothias-Esposito Amina Bouslimani Daniel Petras Julia M. Gauglitz Nicole Sikora Fernando Vargas Justin J. J. van der Hooft Madeleine Ernst Kyo Bin Kang Christine M. Aceves Andrés Mauricio Caraballo-Rodríguez Irina Koester Kelly C. Weldon Samuel BERTRAND Catherine Roullier Kunyang Sun Richard M. Tehan Cristopher A. Boya Christian Martin H. Marcelino Gutiérrez Aldo Moreno Ulloa Javier Andres Tejeda Mora Randy Mojica-Flores Johant Lakey-Beitia Victor Vásquez-Chaves Angela I. Calderón Nicole Tayler Robert A. Keyzers Fidele Tugizimana Nombuso Ndlovu Alexander A. Aksenov Alan K. Jarmusch Robin Schmid Andrew W. Truman Nuno Bandeira Mingxun Wang Pieter Dorrestein.
Herein, we present a protocol for the use of Global Natural Products Social (GNPS) Molecular Networking, an interactive online chemistry-focused mass spectrometry data curation and analysis infrastructure. The goal of GNPS is to provide as much chemical insight for an untargeted tandem mass spectrometry data set as possible and to connect this chemical insight to the underlying biological questions a user wishers to address. This can be performed within one experiment or at the repository scale. GNPS not only serves as a public data repository for untargeted tandem mass spectrometry data with the sample information (metadata), it also captures community knowledge that is disseminated via living data across all public data. One or the main analysis tools used by the GNPS community is molecular networking. Molecular networking creates a structured data table that reflects the chemical space from tandem mass spectrometry experiments via computing the relationships of the tandem mass spectra through spectral similarity. This protocol provides step-by-step instructions for creating reproducible high-quality molecular networks. For training purposes, the reader is led through the protocol from recalling a public data set and its sample information to creating and interpreting a molecular network. Each data analysis job can be shared or cloned to disseminate the knowledge gained, thus propagating information that can lead to the discovery of molecules, metabolic pathways, and ecosystem/community interactions.
PeerJ. 2019; doi:10.7717/peerj.7536
A comparison of inducible, ontogenetic, and interspecific sources of variation in the foliar metabolome in tropical trees
Brian E. Sedio, Armando Durant Archibold, Juan Camilo Rojas Echeverri, Chloé Debyser, Cristopher A. Boya.
S. Joseph Wright
Plant interactions with other organisms are mediated by chemistry, yet chemistry varies among conspecific and within individual plants. The foliar metabolome—the suite of small-molecule metabolites found in the leaf—changes during leaf ontogeny and is influenced by the signaling molecule jasmonic acid. Species differences in secondary metabolites are thought to play an important ecological role by limiting the host ranges of herbivores and pathogens, and hence facilitating competitive coexistence among plant species in species-rich plant communities such as tropical forests. Yet it remains unclear how inducible and ontogenetic variation compare with interspecific variation, particularly in tropical trees. Here, we take advantage of novel methods to assemble mass spectra of all compounds in leaf extracts into molecular networks that quantify their chemical structural similarity in order to compare inducible and ontogenetic chemical variation to among-species variation in species-rich tropical tree genera. We ask (i) whether young and mature leaves differ chemically, (ii) whether jasmonic acid-inducible chemical variation differs between young and mature leaves, and (iii) whether interspecific exceeds intraspecific chemical variation for four species from four hyperdiverse tropical tree genera. We observed significant effects of the jasmonic acid treatment for three of eight combinations of species and ontogenetic stage evaluated. Three of the four species also exhibited large metabolomic differences with leaf ontogenetic stage. The profound effect of leaf ontogenetic stage on the foliar metabolome suggests a qualitative turnover in secondary chemistry with leaf ontogeny. We also quantified foliar metabolomes for 45 congeners of the four focal species. Chemical similarity was much greater within than between species for all four genera, even when within-species comparisons included leaves that differed in age and jasmonic acid treatment. Despite ontogenetic and inducible variation within species, chemical differences among congeneric species may be sufficient to partition niche space with respect to chemical defense.
Sci Rep. 2019;9(1):3019
Viscosin-like lipopeptides from frog skin bacteria inhibit Aspergillus fumigatus and Batrachochytrium dendrobatidis detected by imaging mass spectrometry and molecular networking
Christian Martin H., Roberto Ibáñez, Louis-Félix Nothias, Cristopher A. Boya P., Laura K. Reinert, Louise A. Rollins-Smith, Pieter C. Dorrestein,
Amphibian populations worldwide have declined and in some cases become extinct due to chytridiomycosis, a pandemic disease caused by the fungus Batrachochytrium dendrobatidis; however, some species have survived these fungal epidemics. Previous studies have suggested that the resistance of these species is due to the presence of cutaneous bacteria producing antifungal metabolites. As our understanding of these metabolites is still limited, we assessed the potential of such compounds against human-relevant fungi such as Aspergillus. In this work we isolated 201 bacterial strains from fifteen samples belonging to seven frog species collected in the highlands of Panama and tested them against Aspergillus fumigatus. Among the 29 bacterial isolates that exhibited antifungal activity, Pseudomonas cichorii showed the greatest inhibition. To visualize the distribution of compounds and identify them in the inhibition zone produced by P. cichorii, we employed MALDI imaging mass spectrometry (MALDI IMS) and MS/MS molecular networking. We identified viscosin and massetolides A, F, G and H in the inhibition zone. Furthermore, viscosin was isolated and evaluated in vitro against A. fumigatus and B. dendrobatidis showing MIC values of 62.50 µg/mL and 31.25 µg/mL, respectively. This is the first report of cyclic depsipeptides with antifungal activity isolated from frog cutaneous bacteria.
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