Inventorying secondary metabolism applying metabolomic strategies: contribution to the Brazilian biodiversity valuation

• Grant number: 20/02207-5
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
• Start date: December 01, 2021
• End date: November 30, 2026
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Norberto Peporine Lopes
• Grantee: Norberto Peporine Lopes
• Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
• Pesquisadores principais: Paulo Cézar Vieira
• Associated researchers: Alan William Meerow ; Andrés Eduardo Brunetti ; Andrés Sergio Moreira Muñoz ; Antonio Campos Rocha Neto ; Célio Fernando Baptista Haddad ; Diego German Gutierrez ; Giuliano Cesar Clososki ; Guilherme Corrêa de Oliveira ; Ingrid Koch ; Jennifer Mandel ; Jimi Naoki Nakajima ; João Luis Callegari Lopes ; Juliana Massimino Feres ; Leticia Veras Costa Lotufo ; Marcelo Monge Egea ; Mariana Andrea Grossi ; Mariana Lúcio Lyra ; Pieter C Dorrestein ; Rafael Borges da Silva Valadares ; Ricardo Roberto da Silva ; Ricardo Vessecchi Lourenço ; Thais Guaratini ; Túlio Marcos Nunes
• Associated research grant(s): 24/03447-0 - EMU granted in process 2020/02207-5: high resolution mass spectrometer with electrospray ionizing source (ESI-QTOF), AP.EMU; 24/02286-3 - Integrating Metabolome Evolution and Systematics of Stifftioideae (Asteraceae), AP.R
• Associated scholarship(s): 25/05777-0 - Anticancer potential in extracts produced by bacteria from Brazilian caves, BP.IC; 24/09302-4 - Chemical characterization of a new species of Lychnophora: a tribute to Professor Pirani, BP.IC; 24/06864-1 - Training in phytochemical and spectrometric processes, BP.TT; + associated scholarships 23/18392-4 - Use of mass spectrometry and metabolomic tools in the analysis of populations of plant species from Brazilian biodiversity, BP.PD; 23/03346-7 - Metabolomic analysis of the chemodiversity present in the Amaryllidaceae family and prospection of anticholinesterase activity, BP.DR; 23/03842-4 - Impact of anthropization on chemical and biological biodiversity in caves. What we're losing?, BP.PD; 23/00837-0 - Inventorying secondary metabolism through metabolomics: contribution to the valuation of brazilian biodiversity, BP.DD; 22/05378-0 - Chemical prospection and metabolomics studies in the microbiological diversity in caves, BP.DR; 22/11212-8 - Caracterização de metabólitos secundários de alta polaridade de Asteraceae, BP.IC; 22/01073-0 - Metabolic diversity of anurans in the context of symbiotic interactions using integrative omics approaches, BP.PD - associated scholarships

Abstract

Plants and living organisms emit, detect and respond to chemical stimuli, thus creating an almost unlimited number of interactions through chemical signals. Most of these molecules are classified as secondary metabolites and are an important area of research in our country. Technological and intellectual advances in the last two decades have allowed the development of analyzes of natural products at various molecular levels, including molecular diversity and taxonomy, chemical ecology, understanding of circadian rhythms, among others. These advances have also deepened our understanding of nature to encompass interactions at various levels of organisms at different rates. Mass spectrometry instruments are important tools for investigating the incredibly diverse chemistry that is associated with these biological systems. Our ability to inventory this chemistry, using modern tools, has increased our understanding of the function of secondary metabolism. In this project, we intend to develop computer and spectrometry strategies in the universal analysis of small molecules, seeking to establish a comprehensive understanding of natural products in different biological models and seeking to add value to these substances through pharmacological evaluation. (AU)

Scientific publications

(28)

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

FERNANDEZ-BOBEY, ANTONIO; FERREIRA PINTO, MERI EMILI; DE ALMEIDA, LARISSA COSTA; DE SOUZA, BIBIANA MONSON; DIAS, NATHALIA BAPTISTA; DE PAULA-SOUZA, JULIANA; CILLI, EDUARDO MAFFUD; LOPES, NORBERTO PEPORINE; COSTA-LOTUFO, LETICIA VERAS; PALMA, MARIO SERGIO; et al. Cytotoxic Cyclotides from Anchietea pyrifolia, a South American Plant Species. Journal of Natural Products, v. 85, n. 9, p. 8-pg., 2022-08-31. (14/50926-0, 19/04381-5, 20/02207-5, 14/25222-9, 13/07600-3, 19/26550-3, 17/17098-4, 16/16212-5)

MENDONCA, JACQUELINE NAKAU; JABOR, VALQUIRIA A. POLISEL; ARINI, GABRIEL SANTOS; DA SILVA, RICARDO ROBERTO; DA SILVA, RAFAEL CARVALHO; VESSECCHI, RICARDO; DO NASCIMENTO, FABIO SANTOS; LOPES, NORBERTO PEPORINE. JUVENILE HORMONE III: SOURCE REACTIONS AND COLLISION-INDUCED DISSOCIATION IN ESI-MS/MS. Química Nova, v. N/A, p. 5-pg., 2023-08-21. (20/02207-5)

BORGES, LETICIA DA SILVA; CARVALHO BATISTA, JOAO HENRIQUE; BOZZINI, LEANDRO; LOURENCO JR, CELSO DONIZETE; LOPES, NORBERTO PEPORINE; CLOSOSKI, GIULIANO CESAR; VESSECCHI, RICARDO. Are benzoylium and nitrilium ions produced from substituted 2-arene-2-oxazolines during mass spectrometry? A study based on density functional theory calculations, quantum theory of atoms in molecules, and electrospray ionization tandem mass spectrometry. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, v. 37, n. 4, p. 11-pg., 2023-02-28. (17/04819-5, 09/51812-0, 09/08281-3, 14/50265-3, 20/02207-5, 18/14150-8, 14/23604-1)

PILON, ALAN CESAR; DEL GRANDE, MARCELO; SILVERIO, MAIRA R. S.; SILVA, RICARDO R.; ALBERNAZ, LORENA C.; VIEIRA, PAULO CEZAR; LOPES, JOAO LUIS CALLEGARI; ESPINDOLA, LAILA S.; LOPES, NORBERTO PEPORINE. Combination of GC-MS Molecular Networking and Larvicidal Effect against Aedes aegypti for the Discovery of Bioactive Substances in Commercial Essential Oils. Molecules, v. 27, n. 5, p. 17-pg., 2022-03-01. (20/02207-5)

NETO, FAUSTO CARNEVALE; CLARK, TREVOR N.; LOPES, NORBERTO P.; LININGTON, ROGER G.. Evaluation of Ion Mobility Spectrometry for Improving Constitutional Assignment in Natural Product Mixtures. Journal of Natural Products, v. 85, n. 3, p. 11-pg., 2022-03-25. (14/12343-2, 16/22573-0, 20/02207-5)

TOLLER-KAWAHISA, JULIANA ESCHER; HIROKI, CARLOS HIROJI; SILVA, CAMILA MEIRELLES DE SOUZA; NASCIMENTO, DANIELE CARVALHO; PUBLIO, GABRIEL AZEVEDO; MARTINS, TIMNA VARELA; DAMASCENO, LUIS EDUARDO ALVES; VERAS, FLAVIO PROTASIO; VIACAVA, PAULA RAMOS; SUKESADA, FABIO YUJI; et al. The metabolic function of pyruvate kinase M2 regulates reactive oxygen species production and microbial killing by neutrophils. NATURE COMMUNICATIONS, v. 14, n. 1, p. 16-pg., 2023-07-17. (13/08216-2, 19/25298-9, 17/01714-8, 20/02207-5)

BRUNETTI, ANDRES E.; BUNK, BOYKE; LYRA, MARIANA L.; FUZO, CARLOS A.; MARANI, MARIELA M.; SPROEER, CATHRIN; HADDAD, CELIO F. B.; LOPES, NORBERTO P.; OVERMANN, JOERG. olecular basis of a bacterial-amphibian symbiosis revealed by comparative genomics, modeling, and functional testin. ISME Journal, v. 16, n. 3, OCT 2021. (20/02207-5, 13/50954-0, 17/26162-8, 17/23725-1, 14/20915-6)

LOPES, NORBERTO PEPORINE; KATO, NATALIA NAOMI; BUQUI, GABRIELA AMARAL; MENDONCA, JACQUELINE NAKAU; LOPES, JOAO LUIS CALLEGARI; LOPEZ, RENATA FONSECA VIANNA. Mapping Cutaneous Tissue Distribution of Sesquiterpene Lactone Goyazensolide Using MALDI Imaging. REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY, v. 34, n. 6, p. 6-pg., 2024-06-27. (22/05378-0, 20/02207-5, 22/11454-1)

ARINI, GABRIEL SANTOS; MENCUCINI, LUIZ GABRIEL SOUZA; DE FELICIO, RAFAEL; FEITOSA, LUIS GUILHERME PEREIRA; REZENDE-TEIXEIRA, PAULA; TSUJI, HENRIQUE MARCEL YUDI DE OLIVEIRA; PILON, ALAN CESAR; PINHO, DANIELLE ROCHA; LOTUFO, LETICIA VERAS COSTA; LOPES, NORBERTO PEPORINE; et al. A complementary approach for detecting biological signals through a semi-automated feature selection tool. RONTIERS IN CHEMISTR, v. 12, p. 11-pg., 2024-10-25. (17/18922-2, 21/10401-9, 20/02207-5)

ZAVATIN, DANILO ALVARENGA; RAMOS, RENATO; MONGE, MARCELO; HARLEY, RAYMOND MERVYN. A new species of Hypenia (Lamiaceae, Hyptidinae) from the Espinhaço Range, Brazil. PHYTOTAXA, v. 682, n. 1, p. 10-pg., 2025-01-16. (22/03949-0, 24/02286-3, 20/02207-5)

DA COSTA, BRUNO RUIZ BRANDAO; DA SILVA, RICARDO ROBERTO; BIGAO, VITOR LUIZ CALEFFO PIVA; PERIA, FERNANDA MARIS; DE MARTINIS, BRUNO SPINOSA. Hybrid volatilomics in cancer diagnosis by HS-GC-FID fingerprinting. JOURNAL OF BREATH RESEARCH, v. 17, n. 2, p. 15-pg., 2023-04-01. (19/05026-4, 20/02207-5, 17/18922-2)

NETO, FAUSTO CARNEVALE; VESSECCHI, RICARDO. Structural elucidation of 14-membered ring macrolide antibiotics using electrospray ionization tandem mass spectrometry and density functional theory calculations. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, v. 38, n. 24, p. 12-pg., 2024-12-30. (20/02207-5, 14/23604-1)

DA SILVA, RODRIGO MOREIRA; BARBIERI, JESSICA GUASTALLI; MURIE, VALTER EDUARDO; SILVERIO, MAIRA ROSATO SILVEIRA; SOLDI, RAFAEL AUGUSTO; ALBERNAZ, LORENA CARNEIRO; ESPINDOLA, LAILA SALMEN; VIEIRA, PAULO CEZAR; CLOSOSKI, GIULIANO CESAR; VESSECCHI, RICARDO; et al. Characterization of the fragmentation mechanisms in electrospray ionization tandem mass spectrometry of chloroquinoline derivatives with larvicidal activity against Aedes aegypti. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, v. 38, n. 12, p. 10-pg., 2024-06-30. (14/23604-1, 20/02207-5)

FEITOSA, LUIS GUILHERME PEREIRA; FERES, JULIANA MASSIMINO; GODINHO, CAMILA CAPEL; ALBERNAZ, LORENA CARNEIRO; ESPINDOLA, LAILA SALMEN; VESSECCHI, RICARDO; GUARATINI, THAIS; LOPES, NORBERTO PEPORINE. Characterization of Larvicidal Diterpene Resin Acids in Melipona quadrifasciata Geopropolis via LC-ESI-MS/MS, GC-MS and Computational Analysis. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, v. 39, n. 12, p. 13-pg., 2025-04-30. (19/22357-4, 20/02207-5)

DALLAGNOL, ANDREA MICAELA; DALLAGNOL, VERONICA CROSTOMA; VIGNOLO, GRACIELA MARGARITA; LOPES, NORBERTO PEPORINE; BRUNETTI, ANDRES EDUARDO. Flavonoids and Phenylethylamides Are Pivotal Factors Affecting the Antimicrobial Properties of Stingless Bee Honey. Journal of Agricultural and Food Chemistry, v. 70, n. 39, p. 8-pg., 2022-09-26. (20/02207-5)

BORELLI, TIAGO CABRAL; ARINI, GABRIEL SANTOS; FEITOSA, LUIS G. P.; DORRESTEIN, PIETER C.; LOPES, NORBERTO PEPORINE; DA SILVA, RICARDO R.. Improving annotation propagation on molecular networks through random walks: introducing ChemWalker. Bioinformatics, v. 39, n. 3, p. 2-pg., 2023-03-01. (21/08235-3, 20/02207-5, 17/18922-2, 19/05026-4, 21/10401-9)

MINDER, BASIL; MENDONCA, JACQUELINE N.; GRANT, TARAN; LOPES, NORBERTO P.. Gas-Phase Fragmentation Reactions of Protonated Pumiliotoxin (+)-251D and Allopumiliotoxin (+)-267A in ESI-MS/MS. Journal of the Brazilian Chemical Society, v. N/A, p. 5-pg., 2023-06-20. (21/03515-8, 20/02207-5, 18/15425-0)

BRUNETTI, ANDRES E.; FUZO, CARLOS A.; AGUILAR, SILVANA; RIVERA-CORREA, MAURICIO; MARANI, MARIELA M.; LOPES, NORBERTO P.. The Significance of Hypervariability and Conserved Motifs in Antimicrobial Peptides from Tree Frogs. Journal of Natural Products, v. 86, n. 7, p. 9-pg., 2023-05-23. (17/23725-1, 20/02207-5, 14/20915-6)

DE SOUZA, AMANDA ALVARENGA; DIAS VIEGAS, FLAVIA PEREIRA; GONTIJO, VANESSA SILVA; VIEIRA DOMINGUES, JADINA SANTOS; GIUSTI-PAIVA, ALEXANDRE; VILELA, FABIANA CARDOSO; DA SILVA, GERALDO ALVES; AMARAL, JULIANO GERALDO; LOPES, NORBERTO PEPORINE; VIEGAS JR, CLAUDIO. Antinociceptive Effect of Dillenia indica (Linn.) Mediated by Opioid and Cannabinoid Systems: Pharmacological and Chemical Studies. CHEMISTRY & BIODIVERSITY, v. 21, n. 3, p. 14-pg., 2024-03-01. (20/02207-5, 14/50265-3)

ZUFFA, SIMONE; SCHMID, ROBIN; BAUERMEISTER, ANELIZE; GOMES, PAULO WENDER P.; CARABALLO-RODRIGUEZ, ANDRES M.; EL ABIEAD, YASIN; ARON, ALLEGRA T.; GENTRY, EMILY C.; ZEMLIN, JASMINE; MEEHAN, MICHAEL J.; et al. microbeMASST: a taxonomically informed mass spectrometry search tool for microbial metabolomics data. NATURE MICROBIOLOGY, v. 9, n. 2, p. 10-pg., 2024-02-01. (20/02207-5, 19/03008-9, 20/06430-0, 15/17177-6, 22/12654-4, 18/24865-4)

RABICO, FRANCIENE; BORELLI, TIAGO CABRAL; ALNOCH, ROBSON CARLOS; POLIZELI, MARIA DE LOURDES TEIXEIRA DE MORAES; DA SILVA, RICARDO R.; SILVA-ROCHA, RAFAEL; GUAZZARONI, MARIA-EUGENIA. Novel Pseudomonas Species Prevent the Growth of the Phytopathogenic Fungus Aspergillus flavus. BIOTECH, v. 13, n. 2, p. 20-pg., 2024-06-01. (20/02207-5, 21/01748-5, 19/05026-4, 17/18922-2, 21/08235-3)

MONGE, MARCELO; MARQUES, DANILO; LEONI, LUCIO DE SOUZA; NAKAJIMA, JIMI NAOKI. A new species of Lepidaploa (Cass.) Cass. (Vernonieae, Asteraceae) from Mantiqueira range, southeastern Brazil. BRITTONIA, v. 75, n. 2, p. 10-pg., 2023-04-12. (11/51290-3, 20/02207-5)

CHACON, DAISY SOTERO; SANTOS, MARLON DIAS MARIANO; BONILAURI, BERNARDO; VILASBOA, JOHNATAN; DA COSTA, CIBELE TESSER; DA SILVA, IVANICE BEZERRA; TORRES, TAFFAREL DE MELO; DE ARAUJO, THIAGO FERREIRA; ROQUE, ALAN DE ARAUJO; PILON, ALAN CESAR; et al. Non-target molecular network and putative genes of flavonoid biosynthesis in Erythrina velutina Willd., a Brazilian semiarid native woody plant. FRONTIERS IN PLANT SCIENCE, v. 13, p. 22-pg., 2022-09-08. (20/02207-5, 14/50926-0)

BRUNETTI, ANDRES E.; LYRA, MARIANA L.; BAUERMEISTER, ANELIZE; BUNK, BOYKE; BOEDEKER, CHRISTIAN; MUESKEN, MATHIAS; NETO, FAUSTO CARNEVALE; MENDONCA, JACQUELINE NAKAU; CARABALLO-RODRIGUEZ, ANDRES MAURICIO; MELO, WEILAN G. P.; et al. Host macrocyclic acylcarnitines mediate symbiotic interactions between frogs and their skin microbiome. ISCIENCE, v. 26, n. 11, p. 20-pg., 2023-10-16. (17/26162-8, 21/10639-5, 20/02207-5, 17/23725-1, 12/21803-1, 14/50265-3, 14/20915-6, 17/17648-4, 14/01651-8, 15/01001-6, 13/50954-0)

ARINI, GABRIEL SANTOS; BORELLI, TIAGO CABRAL; FERREIRA, ELTHON GOIS; DE FELICIO, RAFAEL; REZENDE-TEIXEIRA, PAULA; PEDRINO, MATHEUS; RABICO, FRANCIENE; DE SIQUEIRA, GUILHERME MARCELINO VIANA; MENCUCINI, LUIZ GABRIEL; TSUJI, HENRIQUE; et al. A multi-omics reciprocal analysis for characterization of bacterial metabolism. FRONTIERS IN MOLECULAR BIOSCIENCES, v. 12, p. 15-pg., 2025-03-20. (20/02207-5, 21/09375-3, 19/25432-7, 21/08235-3, 21/01748-5, 17/18922-2, 21/10401-9)

BAUERMEISTER, ANELIZE; FURTADO, LUCIANA COSTA; FERREIRA, ELTHON G.; MOREIRA, EDUARDA ANTUNES; JIMENEZ, PAULA CHRISTINE; LOPES, NORBERTO PEPORINE; ARAUJO, WELINGTON LUIZ; OLCHANHESKI, LUIZ RICARDO; LOTUFO, TITO MONTEIRO DA CRUZ; COSTA-LOTUFO, LETICIA VERAS. Chemical and microbial diversity of a tropical intertidal ascidian holobiont. MARINE ENVIRONMENTAL RESEARCH, v. 194, p. 13-pg., 2023-12-26. (20/02207-5, 19/03008-9, 15/17177-6, 22/12654-4, 17/18235-5, 20/08987-2, 17/17648-4)

GARCIA, FABIOLA ALMEIDA; FUENTES, TALIA FROMETA; ALONSO, ISEL PASCUAL; BOSCH, ROBERTO ALONSO; BRUNETTI, ANDRES E.; LOPES, NORBERTO PEPORINE. A Comprehensive Review of Patented Antimicrobial Peptides from Amphibian Anurans. Journal of Natural Products, v. 87, n. 3, p. 17-pg., 2024-02-27. (20/02207-5, 23/00837-0)

DA SILVA, WALACE BRENO; HISPAGNOL, GABRIEL FELIPE; NUNES, EMANUEL VICTOR DOS SANTOS; CASTRO-GAMBOA, IAN; PILON, ALAN CESAR. Plant Sample Preparation for Metabolomics, Lipidomics, Ionomics, Fluxomics, and Peptidomics. SEPARATIONS, v. 12, n. 2, p. 21-pg., 2025-02-01. (19/15889-0, 20/02207-5, 14/50926-0, 20/11967-3)