{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,11]],"date-time":"2026-02-11T17:40:22Z","timestamp":1770831622651,"version":"3.50.1"},"reference-count":90,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2022,7,25]],"date-time":"2022-07-25T00:00:00Z","timestamp":1658707200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Microbiol."],"abstract":"<jats:p>Fungal secondary metabolites constitute a rich source of yet undiscovered bioactive compounds. Their production is often silent under standard laboratory conditions, but the production of some compounds can be triggered simply by altering the cultivation conditions. The usage of an organic salt \u2013 ionic liquid \u2013 as growth medium supplement can greatly impact the biosynthesis of secondary metabolites, leading to higher diversity of compounds accumulating extracellularly. This study examines if such supplements, specifically cholinium-based ionic liquids, can support the discovery of bioactive secondary metabolites across three model species: <jats:italic>Neurospora crassa, Aspergillus nidulans<\/jats:italic>, and <jats:italic>Aspergillus fumigatus<\/jats:italic>. Enriched organic extracts obtained from medium supernatant revealed high diversity in metabolites. The supplementation led apparently to increased levels of either 1-aminocyclopropane-1-carboxylate or \u03b1-aminoisobutyric acid. The extracts where bioactive against two major foodborne bacterial strains: <jats:italic>Staphylococcus aureus<\/jats:italic> and <jats:italic>Escherichia coli<\/jats:italic>. In particular, those retrieved from <jats:italic>N. crassa<\/jats:italic> cultures showed greater bactericidal potential compared to control extracts derived from non-supplemented cultures. An untargeted mass spectrometry analysis using the Global Natural Product Social Molecular Networking tool enabled to capture the chemical diversity driven by the ionic liquid stimuli. Diverse macrolides, among other compounds, were putatively associated with <jats:italic>A. fumigatus<\/jats:italic>; whereas an unexpected richness of cyclic (depsi)peptides with <jats:italic>N. crassa<\/jats:italic>. Further studies are required to understand if the identified peptides are the major players of the bioactivity of <jats:italic>N. crassa<\/jats:italic> extracts, and to decode their biosynthesis pathways as well.<\/jats:p>","DOI":"10.3389\/fmicb.2022.946286","type":"journal-article","created":{"date-parts":[[2022,7,26]],"date-time":"2022-07-26T13:07:04Z","timestamp":1658840824000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":5,"title":["Untargeted Metabolomics Sheds Light on the Secondary Metabolism of Fungi Triggered by Choline-Based Ionic Liquids"],"prefix":"10.3389","volume":"13","author":[{"given":"Patr\u00edcia","family":"Sequeira","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maika","family":"Rothkegel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Patr\u00edcia","family":"Domingos","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Isabel","family":"Martins","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"C\u00e9line C.","family":"Leclercq","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jenny","family":"Renaut","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gustavo H.","family":"Goldman","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cristina","family":"Silva Pereira","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1965","published-online":{"date-parts":[[2022,7,25]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","DOI":"10.1186\/s12864-016-2577-6","article-title":"Transcriptomic and metabolomic profiling of ionic liquid stimuli unveils enhanced secondary metabolism in Aspergillus nidulans.","volume":"17","author":"Alves","year":"2016","journal-title":"BMC Genomics"},{"key":"B2","doi-asserted-by":"publisher","first-page":"548","DOI":"10.1021\/ac901790q","article-title":"Sensitive and rapid method for amino acid quantitation in malaria biological samples using AccQ Tag ultra performance liquid chromatography-electrospray ionization-MS\/MS with multiple reaction monitoring.","volume":"82","author":"Armenta","year":"2010","journal-title":"Anal. Chem."},{"key":"B3","doi-asserted-by":"publisher","first-page":"1954","DOI":"10.1038\/S41596-020-0317-5","article-title":"Reproducible molecular networking of untargeted mass spectrometry data using GNPS.","volume":"15","author":"Aron","year":"2020","journal-title":"Nat. Protoc."},{"key":"B4","doi-asserted-by":"publisher","first-page":"652","DOI":"10.1016\/B978-0-12-818731-9.00111-7","article-title":"Trends in antimicrobial resistance in healthcare-associated infections: a global concern","author":"Arslan","year":"2022","journal-title":"Encyclopedia of Infection and Immunity"},{"key":"B5","doi-asserted-by":"publisher","first-page":"1504","DOI":"10.1126\/science.1155888","article-title":"VelB\/VeA\/LaeA complex coordinates light signal with fungal development and secondary metabolism.","volume":"320","author":"Bayram","year":"2008","journal-title":"Science"},{"key":"B6","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1534\/genetics.119.302277","article-title":"Control of development, secondary metabolism and light-dependent carotenoid biosynthesis by the velvet complex of Neurospora crassa.","volume":"212","author":"Bayram","year":"2019","journal-title":"Genetics"},{"key":"B7","doi-asserted-by":"publisher","first-page":"419","DOI":"10.1007\/S13213-018-1351-1","article-title":"Current strategies to induce secondary metabolites from microbial biosynthetic cryptic gene clusters.","volume":"68","author":"Begani","year":"2018","journal-title":"Ann. Microbiol."},{"key":"B8","doi-asserted-by":"publisher","first-page":"213","DOI":"10.1038\/nchembio869","article-title":"Genomics-driven discovery of PKS-NRPS hybrid metabolites from Aspergillus nidulans.","volume":"3","author":"Bergmann","year":"2007","journal-title":"Nat. Chem. Biol."},{"key":"B9","doi-asserted-by":"publisher","first-page":"193","DOI":"10.1016\/bs.adgen.2020.11.006","article-title":"Fungal natural products galaxy: biochemistry and molecular genetics toward blockbuster drugs discovery.","volume":"107","author":"Bhattarai","year":"2021","journal-title":"Adv. Genet."},{"key":"B10","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1128\/microbiolspec.funk-0009-2016","article-title":"Biologically Active Secondary Metabolites from the Fungi.","volume":"4","author":"Bills","year":"2016","journal-title":"Microbiol. Spectr."},{"key":"B11","doi-asserted-by":"publisher","first-page":"619","DOI":"10.1002\/1439-7633(20020703)3:7<619::AID-CBIC619>3.0.CO;2-9","article-title":"Big effects from small changes: possible ways to explore nature\u2019s chemical diversity.","volume":"3","author":"Bode","year":"2002","journal-title":"Chembiochem"},{"key":"B12","doi-asserted-by":"publisher","first-page":"2207","DOI":"10.1021\/cr050952t","article-title":"Designing Small Molecules for Biodegradability.","volume":"107","author":"Boethling","year":"2007","journal-title":"Chem. Rev."},{"key":"B13","doi-asserted-by":"publisher","first-page":"21","DOI":"10.1038\/nrmicro2916","article-title":"Regulation of fungal secondary metabolism.","volume":"11","author":"Brakhage","year":"2012","journal-title":"Nat. Rev. Microbiol."},{"key":"B14","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.201900276","article-title":"Sequences of acretocins, peptaibiotics Containing the rare 1-aminocyclopropanecarboxylic acid, from Acremonium crotocinigenum CBS 217.70.","volume":"16","author":"Br\u00fcckner","year":"2019","journal-title":"Chem. Biodivers."},{"key":"B15","doi-asserted-by":"publisher","first-page":"2322","DOI":"10.1021\/cb400541z","article-title":"Complexity generation in fungal polyketide biosynthesis: a spirocycle-forming P450 in the concise pathway to the antifungal drug griseofulvin.","volume":"8","author":"Cacho","year":"2013","journal-title":"ACS Chem. Biol."},{"key":"B16","doi-asserted-by":"publisher","first-page":"16781","DOI":"10.1021\/ja307220z","article-title":"Identification and characterization of the echinocandin b biosynthetic gene cluster from Emericella rugulosa NRRL 11440.","volume":"134","author":"Cacho","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"B17","doi-asserted-by":"publisher","first-page":"447","DOI":"10.1128\/MMBR.66.3.447-459.2002","article-title":"Relationship between secondary metabolism and fungal development.","volume":"66","author":"Calvo","year":"2002","journal-title":"Microbiol. Mol. Biol. Rev."},{"key":"B18","doi-asserted-by":"publisher","first-page":"739","DOI":"10.1055\/S-2002-33791","article-title":"In vitro inhibition of 1,3-\u03b2-Glucan synthase by glycolipids from convolvulaceous species.","volume":"68","author":"Castelli","year":"2002","journal-title":"Planta Med."},{"key":"B19","doi-asserted-by":"publisher","first-page":"1505","DOI":"10.1038\/jid.2014.371","article-title":"Unlocking Fungal Cryptic Natural Produts.","volume":"11","author":"Chiang","year":"2009","journal-title":"Nat. Prod. Commun."},{"key":"B20","year":"2018","journal-title":"Performance Standards for Antimicrobial Susceptibility Testing"},{"key":"B21","doi-asserted-by":"publisher","first-page":"1817","DOI":"10.1002\/cbdv.200890171","article-title":"Peptaibiomics: towards a myriad of bioactive peptides containing C(alpha)-dialkylamino acids?","volume":"5","author":"Degenkolb","year":"2008","journal-title":"Chem. Biodivers."},{"key":"B22","doi-asserted-by":"publisher","first-page":"666","DOI":"10.1002\/psc.497","article-title":"The occurrence of peptaibols and structurally related peptaibiotics in fungi and their mass spectrometric identification via diagnostic fragment ions.","volume":"9","author":"Degenkolb","year":"2003","journal-title":"J. Pept. Sci."},{"key":"B23","doi-asserted-by":"publisher","first-page":"1885","DOI":"10.1080\/14786419.2018.1478828","article-title":"A new pregnane steroid from cultures of Aspergillus versicolor.","volume":"33","author":"Ding","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"B24","doi-asserted-by":"publisher","first-page":"1207","DOI":"10.1007\/S00726-020-02890-9","article-title":"Impact of non-proteinogenic amino acids in the discovery and development of peptide therapeutics.","volume":"52","author":"Ding","year":"2020","journal-title":"Amino Acids"},{"key":"B25","doi-asserted-by":"publisher","first-page":"147","DOI":"10.1177\/1934578X1701200140","article-title":"The Rare Amino Acid Building Block 3-(3-furyl)-Alanine in the Formation of Non-ribosomal Peptides.","volume":"12","author":"El Maddah","year":"2017","journal-title":"Nat. Prod. Commun."},{"key":"B26","doi-asserted-by":"publisher","DOI":"10.7554\/eLife.40969","article-title":"Chromatin mapping identifies BasR, a key regulator of bacteria-triggered production of fungal secondary metabolites.","volume":"7","author":"Fischer","year":"2018","journal-title":"eLife"},{"key":"B27","doi-asserted-by":"publisher","first-page":"481","DOI":"10.1016\/j.mib.2008.10.007","article-title":"Secondary metabolism: regulation and role in fungal biology.","volume":"11","author":"Fox","year":"2008","journal-title":"Curr. Opin. Microbiol."},{"key":"B28","doi-asserted-by":"publisher","first-page":"267","DOI":"10.1038\/ja.2006.38","article-title":"Structure determination of neoefrapeptins A to N: peptides with insecticidal activity produced by the fungus Geotrichum candidum.","volume":"59","author":"Fredenhagen","year":"2006","journal-title":"J. Antibiot."},{"key":"B29","doi-asserted-by":"publisher","first-page":"5777","DOI":"10.1021\/jo982306i","article-title":"Nostophycin, a Novel Cyclic Peptide from the Toxic Cyanobacterium Nostoc sp. 152.","volume":"64","author":"Fujii","year":"1999","journal-title":"J. Org. Chem."},{"key":"B30","doi-asserted-by":"publisher","first-page":"3185","DOI":"10.2174\/138161210793292555","article-title":"Chemical Modifications Designed to Improve Peptide Stability: Incorporation of Non-Natural Amino Acids, Pseudo-Peptide Bonds, and Cyclization.","volume":"16","author":"Gentilucci","year":"2010","journal-title":"Curr. Pharm. Des."},{"key":"B31","doi-asserted-by":"publisher","DOI":"10.3390\/JOF7050387","article-title":"Aspergillus Metabolome Database for Mass Spectrometry Metabolomics.","volume":"7","author":"Gil-De-la-fuente","year":"2021","journal-title":"J. Fungi"},{"key":"B32","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1016\/j.bbagen.2017.08.014","article-title":"Marine natural product peptides with therapeutic potential: chemistry, biosynthesis, and pharmacology.","volume":"1862","author":"Gogineni","year":"2018","journal-title":"Biochim. Biophys. Acta Gen. Subj."},{"key":"B33","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0177050","article-title":"Temperature during conidiation affects stress tolerance, pigmentation, and trypacidin accumulation in the conidia of the airborne pathogen Aspergillus fumigatus.","volume":"12","author":"Hagiwara","year":"2017","journal-title":"PLoS One"},{"key":"B34","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1128\/AEM.03157-20","article-title":"Identification and predictions regarding the biosynthesis pathway of polyene macrolides produced by Streptomyces roseoflavus Men-myco-93-63.","volume":"87","author":"Han","year":"2021","journal-title":"Appl. Environ. Microbiol."},{"key":"B35","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2019.00864","article-title":"Ionic liquids chemical stress triggers sphingoid base accumulation in aspergillus nidulans.","volume":"10","author":"Hartmann","year":"2019","journal-title":"Front. Microbiol."},{"key":"B36","doi-asserted-by":"publisher","first-page":"4587","DOI":"10.1039\/C5GC01472G","article-title":"Plasma membrane permeabilisation by ionic liquids: a matter of charge.","volume":"17","author":"Hartmann","year":"2015","journal-title":"Green Chem."},{"key":"B37","doi-asserted-by":"publisher","first-page":"12191","DOI":"10.1021\/acs.analchem.9b01634","article-title":"Combination of isotope labeling and molecular networking of tandem mass spectrometry data to reveal 69 unknown metabolites produced by Penicillium nordicum.","volume":"91","author":"Hautbergue","year":"2019","journal-title":"Anal. Chem."},{"key":"B38","doi-asserted-by":"publisher","first-page":"4688","DOI":"10.1002\/anie.200806121","article-title":"The biosynthetic logic of polyketide diversity.","volume":"48","author":"Hertweck","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"B39","author":"Hoehn","year":"1990","journal-title":"Macrolide Antibiotics. European Patent No 0 398 588 A1"},{"key":"B40","doi-asserted-by":"publisher","first-page":"167","DOI":"10.1038\/s41579-018-0121-1","article-title":"Fungal secondary metabolism: regulation, function and drug discovery.","volume":"17","author":"Keller","year":"2019","journal-title":"Nat. Rev. Microbiol."},{"key":"B41","doi-asserted-by":"publisher","first-page":"937","DOI":"10.1038\/nrmicro1286","article-title":"Fungal Secondary Metabolism - From Biochemistry to Genomics.","volume":"3","author":"Keller","year":"2005","journal-title":"Nat. Rev. Microbiol."},{"key":"B42","doi-asserted-by":"publisher","first-page":"2534","DOI":"10.1093\/bioinformatics\/btn323","article-title":"ProteoWizard: open source software for rapid proteomics tools development.","volume":"24","author":"Kessner","year":"2008","journal-title":"Bioinformatics"},{"key":"B43","doi-asserted-by":"publisher","first-page":"736","DOI":"10.1016\/j.fgb.2010.06.003","article-title":"SMURF: genomic mapping of fungal secondary metabolite clusters.","volume":"47","author":"Khaldi","year":"2010","journal-title":"Fungal Genet. Biol."},{"key":"B44","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2019.01739","article-title":"Efomycins K and L from a termite-associated Streptomyces sp. M56 and their putative biosynthetic origin.","volume":"10","author":"Klassen","year":"2019","journal-title":"Front. Microbiol."},{"key":"B45","doi-asserted-by":"publisher","first-page":"435","DOI":"10.1007\/s00726-005-0275-9","article-title":"Peptaibiomics: an advanced, rapid and selective analysis of peptaibiotics\/peptaibols by SPE\/LC-ES-MS.","volume":"30","author":"Krause","year":"2006","journal-title":"Amino Acids"},{"key":"B46","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2019.02573","article-title":"Fungal cell wall: emerging antifungals and drug resistance.","volume":"10","author":"Lima","year":"2019","journal-title":"Front. Microbiol."},{"key":"B47","doi-asserted-by":"publisher","first-page":"4616","DOI":"10.1021\/ja312503y","article-title":"The fumagillin biosynthetic gene cluster in Aspergillus fumigatus encodes a cryptic terpene cyclase involved in the formation of \u03b2-trans-bergamotene.","volume":"135","author":"Lin","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"B48","doi-asserted-by":"publisher","DOI":"10.3389\/fbioe.2021.632230","article-title":"Recent advances in silent gene cluster activation in Streptomyces.","volume":"9","author":"Liu","year":"2021","journal-title":"Front. Bioeng. Biotechnol."},{"key":"B49","doi-asserted-by":"publisher","first-page":"371","DOI":"10.1146\/annurev-genet-120215-035203","article-title":"Regulation and Role of Fungal Secondary Metabolites.","volume":"50","author":"Macheleidt","year":"2016","journal-title":"Annu. Rev. Genet."},{"key":"B50","doi-asserted-by":"publisher","first-page":"7592","DOI":"10.1002\/anie.201502452","article-title":"Epigenetic genome mining of an endophytic fungus leads to the pleiotropic biosynthesis of natural products.","volume":"54","author":"Mao","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"B51","doi-asserted-by":"publisher","DOI":"10.3390\/microorganisms6030085","article-title":"New 19-Residue Peptaibols from Trichoderma Clade Viride.","volume":"6","author":"Marik","year":"2018","journal-title":"Microorganisms"},{"key":"B52","doi-asserted-by":"publisher","first-page":"262","DOI":"10.1016\/j.jprot.2013.09.015","article-title":"Proteomic alterations induced by ionic liquids in Aspergillus nidulans and Neurospora crassa.","volume":"94","author":"Martins","year":"2013","journal-title":"J. Proteomics"},{"key":"B53","doi-asserted-by":"publisher","first-page":"2","DOI":"10.4172\/2161-1009.1000276","article-title":"Activation of Microbial Silent Gene Clusters: Genomics Driven Drug Discovery Approaches.","volume":"5","author":"Mathew Valayil","year":"2016","journal-title":"Biochem. Anal. Biochem."},{"key":"B54","doi-asserted-by":"publisher","first-page":"493","DOI":"10.1007\/S10295-018-02130-W","article-title":"Refining and expanding nonribosomal peptide synthetase function and mechanism.","volume":"46","author":"McErlean","year":"2019","journal-title":"J. Ind. Microbiol. Biotechnol."},{"key":"B55","doi-asserted-by":"publisher","DOI":"10.1186\/s40694-016-0024-8","article-title":"Current challenges of research on filamentous fungi in relation to human welfare and a sustainable bio-economy: a white paper.","volume":"3","author":"Meyer","year":"2016","journal-title":"Fungal Biol. Biotechnol."},{"key":"B56","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1038\/s41467-018-06082-8","article-title":"Dereplication of microbial metabolites through database search of mass spectra.","volume":"9","author":"Mohimani","year":"2018","journal-title":"Nat. Commun."},{"key":"B57","doi-asserted-by":"publisher","first-page":"490","DOI":"10.1002\/1439-7633(20020603)3:6<490::AID-CBIC490<3.0.CO;2-N","article-title":"Ways of assembling complex natural products on modular nonribosomal peptide synthetases.","volume":"3","author":"Mootz","year":"2002","journal-title":"ChemBioChem"},{"key":"B58","doi-asserted-by":"publisher","first-page":"4788","DOI":"10.1021\/acs.orglett.9b01674","article-title":"The discovery of fungal polyene macrolides via a postgenomic approach reveals a polyketide macrocyclization by trans-acting thioesterase in fungi.","volume":"21","author":"Morishita","year":"2019","journal-title":"Org. Lett."},{"key":"B59","doi-asserted-by":"publisher","first-page":"667","DOI":"10.1021\/np970544n","article-title":"Cyclotheonamides E2 and E3, New Potent Serine Protease Inhibitors from the Marine Sponge of the Genus Theonella.","volume":"61","author":"Nakao","year":"1998","journal-title":"J. Nat. Prod."},{"key":"B60","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2015.00299","article-title":"Microbial communication leading to the activation of silent fungal secondary metabolite gene clusters.","volume":"6","author":"Netzker","year":"2015","journal-title":"Front. Microbiol."},{"key":"B61","doi-asserted-by":"publisher","first-page":"770","DOI":"10.1021\/acs.jnatprod.9b01285","article-title":"Natural Products as Sources of New Drugs over the Nearly Four Decades from 01\/1981 to 09\/2019.","volume":"83","author":"Newman","year":"2020","journal-title":"J. Nat. Prod."},{"key":"B62","doi-asserted-by":"publisher","DOI":"10.3390\/jof6020061","article-title":"Diversity of linear non-ribosomal peptide in biocontrol fungi.","volume":"6","author":"Niu","year":"2020","journal-title":"J. Fungi"},{"key":"B63","doi-asserted-by":"publisher","first-page":"400","DOI":"10.1128\/IAI.70.1.400-402.2002","article-title":"Production of prostaglandins and leukotrienes by pathogenic fungi.","volume":"70","author":"Noverr","year":"2002","journal-title":"Infect. Immun."},{"key":"B64","doi-asserted-by":"publisher","first-page":"1416","DOI":"10.7164\/antibiotics.34.1416","article-title":"Studies on SF=1902 A2 A5, minor components of SF-1902 (globomycin).","volume":"34","author":"Omoto","year":"1981","journal-title":"J. Antibiot."},{"key":"B65","doi-asserted-by":"publisher","first-page":"77","DOI":"10.1139\/w00-128","article-title":"Determination of 1-aminocycopropane-1-carboxylic acid (ACC) to assess the effects of ACC deaminase-containing bacteria on roots of canola seedlings.","volume":"47","author":"Penrose","year":"2001","journal-title":"Can. J. Microbiol."},{"key":"B66","doi-asserted-by":"publisher","first-page":"643","DOI":"10.1039\/B922247B","article-title":"Novel biocompatible cholinium-based ionic liquids\u2014toxicity and biodegradability.","volume":"12","author":"Petkovic","year":"2010","journal-title":"Green Chem."},{"key":"B67","doi-asserted-by":"publisher","first-page":"889","DOI":"10.1039\/b823225c","article-title":"Exploring fungal activity in the presence of ionic liquids.","volume":"11","author":"Petkovic","year":"2009","journal-title":"Green Chem."},{"key":"B68","doi-asserted-by":"publisher","first-page":"1891","DOI":"10.1021\/np800409z","article-title":"Isolation of aerucyclamides C and D and structure revision of microcyclamide 7806A: Heterocyclic ribosomal peptides from Microcystis aeruginosa PCC 7806 and their antiparasite evaluation.","volume":"71","author":"Portmann","year":"2008","journal-title":"J. Nat. Prod."},{"key":"B69","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2015.00573","article-title":"Secondary metabolites in fungus-plant interactions.","volume":"6","author":"Pusztahelyi","year":"2015","journal-title":"Front. Plant Sci."},{"key":"B70","doi-asserted-by":"publisher","DOI":"10.1016\/j.jprot.2020.103798","article-title":"The effects of improving low dietary protein utilization on the proteome of lamb tissues.","volume":"223","author":"Ribeiro","year":"2020","journal-title":"J. Proteomics"},{"key":"B71","doi-asserted-by":"publisher","first-page":"15862","DOI":"10.1021\/acs.analchem.0c03208","article-title":"Automatic Annotation and Dereplication of Tandem Mass Spectra of Peptidic Natural Products.","volume":"92","author":"Ricart","year":"2020","journal-title":"Anal. Chem."},{"key":"B72","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1016\/B978-0-444-63505-1.00006-3","article-title":"Secondary Metabolism and Antimicrobial Metabolites of Aspergillus","author":"Rodrigues","year":"2016","journal-title":"New and Future Developments in Microbial Biotechnology and Bioengineering: Aspergillus System Properties and Applications"},{"key":"B73","doi-asserted-by":"publisher","first-page":"122","DOI":"10.7164\/antibiotics.34.122","article-title":"The structure of roflamycoin, a new polyene macrolide antifungal antibiotic.","volume":"34","author":"Schlegel","year":"1981","journal-title":"J. Antibiot."},{"key":"B74","doi-asserted-by":"publisher","first-page":"2498","DOI":"10.1101\/gr.1239303","article-title":"Cytoscape: a software environment for integrated models of biomolecular interaction networks.","volume":"13","author":"Shannon","year":"2003","journal-title":"Genome Res."},{"key":"B75","doi-asserted-by":"publisher","first-page":"12368","DOI":"10.3390\/molecules190812368","article-title":"Cyclodepsipeptides: A Rich Source of Biologically Active Compounds for Drug Research.","volume":"19","author":"Sivanathan","year":"2014","journal-title":"Molecules"},{"key":"B76","doi-asserted-by":"publisher","first-page":"2710","DOI":"10.1128\/aac.40.12.2710","article-title":"In vitro antifungal and fungicidal activities and erythrocyte toxicities of cyclic lipodepsinonapeptides produced by Pseudomonas syringae pv. syringae.","volume":"40","author":"Sorensen","year":"1996","journal-title":"Antimicrob. Agents Chemother."},{"key":"B77","doi-asserted-by":"publisher","first-page":"577","DOI":"10.1016\/j.bbamem.2016.08.013","article-title":"Therapeutic design of peptide modulators of protein-protein interactions in membranes.","volume":"1859","author":"Stone","year":"2017","journal-title":"Biochim. Biophys. Acta Biomembr."},{"key":"B78","doi-asserted-by":"publisher","first-page":"155","DOI":"10.1021\/np960612q","article-title":"Dolabelides C and D, cytotoxic macrolides isolated from the sea hare Dolabella auricularia.","volume":"60","author":"Suenaga","year":"1997","journal-title":"J. Nat. Prod."},{"key":"B79","doi-asserted-by":"publisher","first-page":"211","DOI":"10.1007\/S11306-007-0082-2","article-title":"Proposed minimum reporting standards for chemical analysis Chemical Analysis Working Group (CAWG) Metabolomics Standards Initiative (MSI).","volume":"3","author":"Sumner","year":"2007","journal-title":"Metabolomics"},{"key":"B80","doi-asserted-by":"publisher","first-page":"2137","DOI":"10.1021\/np2004243","article-title":"Cyclodepsipeptides, Sesquiterpenoids, and Other Cytotoxic Metabolites from the Filamentous Fungus Trichothecium sp. (MSX 51320).","volume":"74","author":"Sy-Cordero","year":"2011","journal-title":"J. Nat. Prod."},{"key":"B81","doi-asserted-by":"publisher","first-page":"425","DOI":"10.2174\/1389203717666161128141438","article-title":"Chemical classification of cyclic depsipeptides.","volume":"18","author":"Taevernier","year":"2017","journal-title":"Curr. Protein Pept. Sci."},{"key":"B82","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.201800485","article-title":"How histone deacetylase inhibitors alter the secondary metabolites of Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana.","volume":"16","author":"Triastuti","year":"2019","journal-title":"Chem. Biodivers."},{"key":"B83","doi-asserted-by":"publisher","first-page":"109","DOI":"10.1016\/j.tim.2007.01.005","article-title":"Oxylipins as developmental and host\u2013fungal communication signals.","volume":"15","author":"Tsitsigiannis","year":"2007","journal-title":"Trends Microbiol."},{"key":"B84","doi-asserted-by":"publisher","first-page":"828","DOI":"10.1038\/nbt.3597","article-title":"Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking.","volume":"34","author":"Wang","year":"2016","journal-title":"Nat. Biotechnol."},{"key":"B85","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23010169","article-title":"Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi.","volume":"23","author":"Wang","year":"2018","journal-title":"Molecules"},{"key":"B86","doi-asserted-by":"publisher","first-page":"E1743","DOI":"10.1073\/pnas.1203689109","article-title":"Mass spectral molecular networking of living microbial colonies.","volume":"109","author":"Watrous","year":"2012","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"B87","year":"2021","journal-title":"Global Antimicrobial Resistance and Use Surveillance System (GLASS) Report: 2021."},{"key":"B88","doi-asserted-by":"publisher","first-page":"2153","DOI":"10.1021\/NP4006794","article-title":"Identification of elaiophylin derivatives from the marine-derived actinomycete Streptomyces sp. 7-145 using PCR-based screening.","volume":"76","author":"Wu","year":"2013","journal-title":"J. Nat. Prod."},{"key":"B89","doi-asserted-by":"publisher","first-page":"518","DOI":"10.1128\/AAC.49.2.518-524.2005","article-title":"Cholesterol import by Aspergillus fumigatus and its influence on antifungal potency of sterol biosynthesis inhibitors.","volume":"49","author":"Xiong","year":"2005","journal-title":"Antimicrob. Agents Chemother."},{"key":"B90","doi-asserted-by":"publisher","first-page":"1260","DOI":"10.1080\/14786419.2017.1342086","article-title":"A new antiviral pregnane from a gorgonian-derived Cladosporium sp. fungus.","volume":"32","author":"Yu","year":"2018","journal-title":"Nat. Prod. Res."}],"container-title":["Frontiers in Microbiology"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fmicb.2022.946286\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,7,26]],"date-time":"2022-07-26T13:07:10Z","timestamp":1658840830000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fmicb.2022.946286\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,7,25]]},"references-count":90,"alternative-id":["10.3389\/fmicb.2022.946286"],"URL":"https:\/\/doi.org\/10.3389\/fmicb.2022.946286","relation":{},"ISSN":["1664-302X"],"issn-type":[{"value":"1664-302X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,7,25]]},"article-number":"946286"}}