Molecular networking as a tool to annotate the metabolites of Bacillus sp. and Serratia marcescens isolates and evaluate their fungicidal effects against Magnapothe oryzae and Bipolaris oryzae

Arriel-Elias MT, de Carvalho Barros Côrtes MV, de Sousa TP, Chaibub AA, de Filippi MCC (2019) Induction of resistance in rice plants using bioproducts produced from Burkholderia pyrrocinia BRM 32113. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-019-05238-3 Arriel-Elias MT, Oliveira MIS, Silva-Lobo VL, Filippi MCC, Babana AH, Conceição EC, Cortes MVCB (2018) Shelf life enhancement of PGPRs using a simple formulation screening method. Afr J Microbiol Res 12(5):1156–2126. https://doi.org/10.5897/AJMR2017.8787 Arriel-Elias MT, de Carvalho Barros Côrtes MV, de Sousa TP, Chaibub AA, Filippi M (2019) Induction of resistance in rice plants using bioproducts produced from Burkholderia pyrrocinia BRM 32113. Environ Sci Pollut Res 26:19705–19718. https://doi.org/10.1007/s11356-019-05238-3 Batista BD (2017) Promoção de crescimento vegetal por Bacillus Sp. RZ2MS9: Dos Genes ao Campo. https://doi.org/10.11606/T.11.2017.tde-15082017-170543 Bazioli JM, Amaral LS, Fill TP, Rodrigues-Filho E (2017) Insights into Penicillium brasilianum secondary metabolism and its biotechnological potential. Molecules 22(6):858. https://doi.org/10.3390/molecules22060858 Brakhage AA (2013) Regulation of fungal secondary metabolism. Nat Rev Microbiol 11(1):21–32. https://doi.org/10.1038/nrmicro2916 Claus D, Berkeley RCW (1986) Genus Bacillus Cohn, 1872. In: Sneath, P.H.A., Mair, N.S., Sharpe, M.E. and J.G. Holt., Ed., Bergey’s Manual of Systematic Bacteriology, The Williams & Wilkins Co., Baltimore, v.2 Côrtes ACAS, Sousa TP, Barros MV, Rodrigues FA, Silva GB, Filippi MCC (2015) Enzyme-induced defense response in the suppression of rice leaf blast (Magnaporthe oryzae) by silicon fertilization and bioagents. Int J Res Stud Biosci 3:22–32 Costa JH, Bazioli JM, Barbosa LD, dos Santos Júnior PLT, Reis FCG, Klimeck T, Crnkovic CM, Berlinck RGS, Sussulini A, Rodrigues ML, Fill TP (2021) Phytotoxic tryptoquialanines produced in vivo by Penicillium digitatum are exported in extracellular vesicles. Mbio 12(1):e03393–e03420. https://doi.org/10.1128/mBio.03393-20 D’Ávila LS, De Filippi MCC, Café-Filho AC (2021) Sensitivity of Pyricularia oryzae populations to fungicides over a 26-year time frame in Brazil. Plant Dis 105(6):1771–1780. https://doi.org/10.1094/pdis-08-20-1806-re Degtyarenko IM, Nieminen RM (2010) Chapter 15—dynamics of biomolecules from first principles. Sci Technol Atom Mol Condens Matter Biol Syst 1:557–573. https://doi.org/10.1016/B978-0-444-53440-8.00015-X Ernst M, Kang KB, Caraballo-Rodríguez AM, Nothias LF, Wandy J, Chen C, Wang M, Rogers S, Medema MH, Dorrestein PC, Van der Hooft JJJ (2019) MolNetEnhancer: enhanced molecular networks by integrating metabolome mining and annotation tools. Metabolites 9(7):144. https://doi.org/10.3390/metabo9070144 Filippi MCC, Silva GB, Silva-Lobo V, Côrtes MVCB, Moraes AJG, Prabhu AS (2011) Leaf blast (Magnaporthe oryzae) suppression and growth promotion by rhizobacteria on aerobic rice in Brazil. Biol Control 58:160–166. https://doi.org/10.1016/j.biocontrol.2011.04.016 Gwinn KD (2018) Bioactive natural products in plant disease control. Stud Nat Prod Chem. https://doi.org/10.1016/B978-0-444-64058-1.00007-8 Hisien-Chun Kim L, Entwistle R, Guo CJ, Ahuja M, Szewczyk E, Hung JH, Chiang YM, Oakley BR, Wang CC (2012)Two separate gene clusters encode the biosynthetic pathway for the meroterpenoids austinol and dehydroaustinol in Aspergillus nidulans. J Am Chem Soc 134(10):4709–4720. https://doi.org/10.1021/ja209809t Ibrahim D (2015) Antimicrobial activity of Penicillium minioluteum ED24, an endophytic fungus residing in Orthosiphon stamineus Benth. World J Pharm Pharm Sci 3(3):121–132 Jamie H (2002) The medicinal chemistry of the isomers of the cyclic dipeptide: cyclo (TRP-PRO). Submitted in fulfilment of the requirements for the degree of PHILOSOPHIAE DOCTOR in the Faculty of Health Sciences, at the University of Port Elizabeth Kanzaki H, Mizuta N, Nitoda T, Kawazu K (2000) Novel diketopiperazine metabolism in a microorganism: two-step hydrolysis of cyclo(Gly-Leu) to amino acids and preliminary characterization of cyclo(Gly-Leu) hydrolase and dipeptidase. J Biosci Bioeng 89(6):602–605. https://doi.org/10.1016/S1389-1723(00)80064-X Katz L, Baltz RH (2016) Natural product discovery: past, present, and future. J Ind Microbiol Biotechnol 43(2–3):155–176. https://doi.org/10.1007/s10295-015-1723-5 Khaldi N, Seifuddin FT, Turner G, Haft D, Nierman WC, Wolfe KH, Fedorova ND (2010) SMURF: Genomic mapping of fungal secondary metabolite clusters. Fungal Genet Biol 47:736–741. https://doi.org/10.1016/j.fgb.2010.06.003 Krithika K, Geetha Ramani D (2013) Screening of Serratia marcescens isolated from soil for secondary metabolites of therapeutic importance. Int J Bioassays 02(08):1162–1165 Lee W, Lee SH, Kim M, Moon JS, Kim GK, Jung HW, Kim IH, Oh JE, Jung HE, Lee HK, Ku KB, Ahn DG, Kim SJ, Kim KS, Oh JW (2018) Vibrio vulnificus quorum-sensing molecule cyclo(Phe-Pro) inhibits RIG-I-mediated antiviral innate immunity. Nat Commun 23(1):1606. https://doi.org/10.1038/s41467-018-04075-1 Lenz G, Balardin RS, Corte GD, Marques LN, Debona D (2010) Diagrammatic scale for assessment of rice brown spot severity. Ciência Rural 40:752–758 (in Portuguese). Levenfors JJ, Hedmana R, Thaningb C, Gerhardsonb B, Welcha CJ (2004) Broad-spectrum antifungal metabolites produced by the soil bacterium Serratia plymuthica A 153. Soil Biol Biochem 36(4):677–685. https://doi.org/10.1016/j.soilbio.2003.12.008 Li Y, Yuana S, Yonga S, Zhaoa T, Liua J (2020) Research progress on small peptides in Chinese Baijiu. J Funct Foods 72:104081. https://doi.org/10.1016/j.jff.2020.104081 Liu S, Su M, Song SJ, Jung JH (2018) Marine-derived Penicillium species as producers of cytotoxic metabolites. Mar Drugs 15(10):329. https://doi.org/10.3390/md15100329 Lo HC, Entwistle R, Guo CJ, Ahuja M, Szewczyk E, Hung JH, Chiang YM, Oakley BR, Wang CC (2012) Two separate gene clusters encode the biosynthetic pathway for the meroterpenoids austinol and dehydroaustinol in Aspergillus nidulans. J Am Chem Soc 134(10):4709–4720. https://doi.org/10.1021/ja209809t Martins BEM, Chaibub AA, Cortes MVCB, Silva-Lobo VL, Filippi MCC (2020) Characterization of bacterial isolates for sustainable rice blast control. Rev Caatinga 33:702–712. https://doi.org/10.1590/1983-21252020v33n313rc Matteoli FP, Passarelli-Araujo HP, Reis RJA, Rocha LO, Souza EM, Aravind L, Olivares FL, Venancio TM (2018) Genome sequencing and assessment of plant growth-promoting properties of a Serratia marcescens strain isolated from vermicompost. BMC Genom 19(1):750. https://doi.org/10.1186/s12864-018-5130-y Melo FMP (2005) Atividade antifúngica de metabólitos secundários produzidos pelo endófito de mandioca Bacillus pumilus MAIII4a. Dissertação. Escola Superior de Agricultura Luiz de Queiroz. Universidade de São Paulo (USP), Piracicaba McInroy JA, Kloepper JW (1995) Survey of indigenous bacterial endophytes from cotton and sweet corn. Plant and Soil 173(2):337–342. https://doi.org/10.1007/BF00011472 Morais JM, Yoshimoto M, Rhoden SA, Pamphile JA (2014) Bioprospecção de microrganismos produtores de compostos bioativos comatividade antitumoral. Uningá Rev 17(1):27–34 Morbach S, Sahm H, Eggeling L (1996) l-Isoleucine production with Corynebacterium glutamicum: Further flux increase and limitation of export. Appl Environ Microbiol 62(12):4345–4351. https://doi.org/10.1128/aem.62.12.4345-4351.1 Nascente AS, Filippi MCC, Lanna AC, Souza ACA, Silva-Lobo VL, Silva GB (2017) Biomass, gas exchange, and nutrient contents in upland rice plants affected by application forms of microorganism growth promoters. Environ Sci Pollut Res Int 24(3):2956–2965. https://doi.org/10.1007/s11356-016-8013-2 Nelson DL, Cox MM (2014) Princípios de bioquímica de lehninger, 6th edn. ARTMED, Porto Alegre Notteghem JL (1981) Cooperative experiment on horizontal resistance to rice blast. In: Blast and upland rice: report and recommendations from the meeting for international collaboration in upland rice improvement. IRRI, Los Baños, pp 43–51 Oliveira SC, Castroagudin VL, Maciel JLN, Pereira DAS, Ceresini PC (2015) Cross-resistance to QoI fungicides azoxystrobin and pyraclostrobin in the wheat blast pathogen Pyricularia oryzae in Brazil. Summa Phytopathol 41:298–304. https://doi.org/10.1590/0100-5405/2072 Prabhu AS, Filippi MC (2006) Brusone em arroz: controle genética, progresso e perspectivas. Santo Antônio de Goiás, Embrapa Rezende CC, Frasca LLM, Silva MA, Pires RAC, Lanna AC, Filippi MCC, Nascente AS (2021) Physiological and agronomic characteristics of the common bean as affected by multifunctional microorganisms. Semina Ciênc Agrárias 42(2):599–618. https://doi.org/10.5433/1679-0359.2021v42n2p599 Sangappillai V, Nadarajah K (2020) Fatty acid synthase beta dehydratase in the lipid biosynthesis pathway is required for conidiogenesis, pigmentation and appressorium formation in Magnaporthe oryzae S6. Int J Mol Sci 21:7224. https://doi.org/10.3390/ijms21197224 Sansinenea E, Ortiz A (2011) Secondary metabolites of soil Bacillus spp. Biotechnol Lett 33(8):1523–1538. https://doi.org/10.1007/s10529-011-0617-5 Santos RMG, Rodrigues-Filho E (2003) Structures of meroterpenes produced by Penicillium sp., an endophytic fungus found associated with Melia azedarach. J Braz Chem Soc 14(5):722–727. https://doi.org/10.1590/S0103-50532003000500004 Schürmann BTM (2010) Austin, dehydroaustin and other metabolites from Penicillium brasilianum. Quim Nova 33(5):1044–1046 Shaner G, Finney RF (1977) The effects of nitrogen fertilization on the expression slowmildewing in Knox wheat. Phytopathology 67:1051–1055 Silva MA, Nascente AS, Filippi MCC, Lanna AC, Silva GB, Fernandes JPT, Arriel-Elias MT (2020) Screening of beneficial microorganisms to improve soybean growth and yield. Braz Arch Biol Technol 63(2):e20190463. https://doi.org/10.1590/1678-4324-2020190463 Sousa TP, Souza ACA, Cortes MVCB, Lanna AC, Pinheiro HA, Filippi MCC, Silva GB (2017) Bioagents and silicon promoting fast early upland rice upland rice growth. Environ Sci Pollut Res 25:3657–3668. https://doi.org/10.1007/s11356-017-0753-0 Sperandio EM, Vale HMM, Reis MS, Cortes MVCB, Lanna AC, Filippi MCC (2017) Evaluation of rhizobacteria in upland rice in Brazil: growth promotion and interaction of induced defense responses against leaf blast (Magnaporthe oryzae). Acta Physiol Plant 39:259. https://doi.org/10.1007/s11738-017-2547-x Ström K, Sjögren J, Broberg A, Schnürer J (2002) Lactobacillus plantarum MiLAB 393 produces the antifungal cyclic dipeptides cyclo(L-Phe-L-Pro) and cyclo(L-Phe-trans-4-OH-L-Pro) and 3-phenyllactic acid. Appl Environ Microbiol 68(9):4322–4327. https://doi.org/10.1128/AEM.68.9.4322-4327.2002 Sumner LW, Amberg A, Barrett D et al (2007) Proposed minimum reporting standards for chemical analysis Chemical Analysis Working Group (CAWG) Metabolomics Standards Initiative (MSI). Metabolomics 3(3):211–221. https://doi.org/10.1007/s11306-007-0082-2 Sumner LW et al (2013) Proposed quantitative and alphanumeric metabolite identification metrics. Metabolomics 10:1047–1049 Vicente CSL, Nascimento FX, Ikuyo Y, Cock PJA, Mota M, Hasegawa K (2016) The genome and genetics of a high oxidative stress tolerant Serratia sp. LCN16 isolated from the plant parasitic nematode Bursaphelenchus xylophilus. BMC Genom 17:301. https://doi.org/10.1186/s12864-016-2626-1 Vogel J, Quax WJ (2019) Chapter 7—enzymatic quorum quenching in biofilms. Molecular mechanism and biotechnological application. Academic Press, New York, pp 173–193