Evaluation of the anti-parasitary and insecticidal activities of benzofuran derivatives, and study of their gas-phase fragmentation reactions using tandem mass spectrometry

• Grant number: 13/20094-0
• Support Opportunities: Regular Research Grants
• Start date: March 01, 2014
• End date: February 29, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antônio Eduardo Miller Crotti
• Grantee: Antônio Eduardo Miller Crotti
• Host Institution: Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (FFCLRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
• Associated researchers: Daniele da Silva Ferreira ; Edson Luiz Lopes Baldin ; Lizandra Guidi Magalhães ; Paulo Marcos Donate ; Renato Luis Tame Parreira ; Ricardo Vessecchi Lourenço ; Viviane Rodrigues Esperandim

Abstract

Neglected tropical diseases are a group of diseases that affect poor areas in Africa, Asia and Latin America. These include schistosomiasis, leishmaniasis and Chagas disease that represent major public health problems in Brazil. In agriculture, the silverleaf whitefly (Bemisia tabaci biotype B) is one of the major pests in tomato crops. Studies have reported the anti-parasitic and insecticidal potential of various benzofuran derivatives, such as dihydrobenzofuran neolignans. Reactions between ortho-hydroxyaldehydes or ortho -hydroxy-ketones and ±-halogenated aldehydes or ketones are the most used synthetic methods for constructing the benzofuran system. In the case of the synthesis of dihydrobenzofuran neolignans, the oxidative coupling between phenylpropanoids units is the most widely used, and the regioselectivity of such coupling depends on the oxidizing agent employed. However, no detailed studies on the intermediates involved in these reactions were found in the literature nor systematic studies on the fragmentation pathways of these compounds in the gas phase using electrospray ionization tandem mass spectrometry (ESI-EM/EM). The goal of this project is the synthesis of some dihydrobenzofuran neolignans by oxidative coupling, as well as other benzofuran compounds employing various routes.. The obtained compounds will be evaluated for their schistosomicidal, leishmanicidal, trypanocidal and insecticidal activities. The mechanisms of the oxidative coupling of phenylpropanoid will be investigated by ESI-MS/MS. The ESI-MS/MS technique also will be used in combination with data obtained from Computational Chemistry for the elucidation of fragmentation pathways of dihydrobenzofuran neolignans and other benzofuran compounds, aiming to obtain structure-fragmentation correlations that could make enable the identification/dereplication of these compounds in complex mixtures in complex mixtures by ESI-MS/MS or HPLC-ESI-MS/MS. (AU)

Scientific publications

(22)

(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)

MEDEIROS, TALITA C. T.; DIAS, HERBERT J.; SILVA, ELIANE O.; FUKUI, MURILO J.; SOARES, ANA CAROLINA F.; KAR, TAPAS; HELENO, VLADIMIR C. G.; DONATE, PAULO M.; PARREIRA, RENATO L. T.; CROTTI, ANTONIO E. M.. Detailed H-1 and C-13 NMR Spectral Data Assignment for Two Dihydrobenzofuran Neolignans. Journal of the Brazilian Chemical Society, v. 27, n. 1, p. 136-143, JAN 2016. (13/20094-0, 11/07623-8, 09/12202-1)

CREVELIN, EDUARDO J.; CROTTI, ANTONIO E. M.; ZUCCHI, TIAGO D.; MELO, ITAMAR S.; MORAES, LUIZ A. B.. Dereplication of Streptomyces sp AMC 23 polyether ionophore antibiotics by accurate-mass electrospray tandem mass spectrometry. Journal of Mass Spectrometry, v. 49, n. 11, p. 1117-1126, NOV 2014. (13/20094-0, 09/51145-3)

VIEIRA, TATIANA M.; DOS SANTOS, ISABELLA A.; SILVA, THAYNA S.; MARTINS, CARLOS H. G.; CROTTI, ANTONIO E. M.. Antimicrobial Activity of Monoketone Curcuminoids Against Cariogenic Bacteria. CHEMISTRY & BIODIVERSITY, v. 15, n. 8, AUG 2018. (13/20094-0, 16/19272-9)

CREVELIN, EDUARDO J.; SALAMI, FERNANDA H.; ALVES, MARCELA N. R.; DE MARTINIS, BRUNO S.; CROTTI, ANTNIO E. M.; MORAES, LUIZ A. B.. Direct Analysis of Amphetamine Stimulants in a Whole Urine Sample by Atmospheric Solids Analysis Probe Tandem Mass Spectrometry. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, v. 27, n. 5, p. 944-947, MAY 2016. (13/50729-7, 13/20094-0, 12/06931-3)

CARRAO, DANIEL BLASCKE; PEREZ DE ALBUQUERQUE, NAYARA CRISTINA; MAURIZ MARQUES, LUCAS MACIEL; MILLER CROTTI, ANTONIO EDUARDO; PILON, ALAN CESAR; BOLZANI, VANDERLAN DA SILVA; BERRETTA, ANDRESA APARECIDA; MORAES DE OLIVEIRA, ANDERSON RODRIGO. In Vitro Metabolism of Artepillin C by Rat and Human Liver Microsomes. Planta Medica, v. 83, n. 8, p. 737-745, MAY 2017. (13/17658-9, 16/07597-0, 13/20094-0)

DIAS, HERBERT J.; VIEIRA, TATIANA M.; CREVELIN, EDUARDO J.; DONATE, PAULO M.; VESSECCHI, RICARDO; CROTTI, ANTONIO E. M.. Fragmentation of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry, v. 52, n. 12, p. 809-816, DEC 2017. (13/20094-0, 14/23604-1)

CREVELIN, EDUARDO J.; POSSATO, BRUNA; LOPES, JOAO L. C.; LOPES, NORBERTO P.; CROTTI, ANTONIO E. M.. Precursor Ion Scan Mode-Based Strategy for Fast Screening of Polyether lonophores by Copper-Induced Gas-Phase Radical Fragmentation Reactions. Analytical Chemistry, v. 89, n. 7, p. 3929-3936, APR 4 2017. (14/50265-3, 13/20094-0)

DIAS, HERBERT JUNIOR; STEFANI, RICARDO; TOMAZ, JOSE CARLOS; VESSECCHI, RICARDO; MILLER CROTTI, ANTONIO EDUARDO. Differentiation between 3,4-and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry. JOURNAL OF ANALYTICAL METHODS IN CHEMISTRY, v. 2017, p. 9-pg., 2017-01-01. (13/20094-0, 14/23604-1)

ALVES, BRUNA GOMES; DE MAGALHAES RODRIGUES MARTINS, CRISTIAN MARLON; FERRANTI PETI, ANA PAULA; BERALDO DE MORAES, LUIZ ALBERTO; DOS SANTOS, MARCOS VEIGA. In vitro evaluation of novel crude extracts produced by actinobacteria for modulation of ruminal fermentation. REVISTA BRASILEIRA DE ZOOTECNIA-BRAZILIAN JOURNAL OF ANIMAL SCIENCE, v. 48, p. 11-pg., 2019-01-01. (13/20094-0, 14/08905-5)

TALITA C. T. MEDEIROS; HERBERT J. DIAS; ELIANE O. SILVA; MURILO J. FUKUI; ANA CAROLINA F. SOARES; TAPAS KAR; VLADIMIR C. G. HELENO; PAULO M. DONATE; RENATO L. T. PARREIRA; ANTÔNIO E. M. CROTTI. Detailed 1H and 13C NMR Spectral Data Assignment for Two Dihydrobenzofuran Neolignans. Journal of the Brazilian Chemical Society, v. 27, n. 1, p. 136-143, 2016-01-00. (11/07623-8, 09/12202-1, 13/20094-0)

BRUNA GOMES ALVES; CRISTIAN MARLON DE MAGALHÃES RODRIGUES MARTINS; ANA PAULA FERRANTI PETI; LUIZ ALBERTO BERALDO DE MORAES; MARCOS VEIGA DOS SANTOS. In vitro evaluation of novel crude extracts produced by actinobacteria for modulation of ruminal fermentation. REVISTA BRASILEIRA DE ZOOTECNIA-BRAZILIAN JOURNAL OF ANIMAL SCIENCE, v. 48, 2019-11-11. (14/08905-5, 13/20094-0)

DIAS, HERBERT JUNIOR; STEFANI, RICARDO; TOMAZ, JOSE CARLOS; VESSECCHI, RICARDO; MILLER CROTTI, ANTONIO EDUARDO. Differentiation between 3,4-and 4,15-Epoxyeudesmanolides by Electrospray Ionization Tandem Mass Spectrometry. JOURNAL OF ANALYTICAL METHODS IN CHEMISTRY, 2017. (13/20094-0, 14/23604-1)

DIAS, HERBERT J.; RODRIGUES, MATHEUS L.; CROTTI, ANTONIO E. M.. Optimization of the Reaction Conditions for the Synthesis of Dihydrobenzofuran Neolignans. Journal of the Brazilian Chemical Society, v. 32, n. 1, p. 20-28, JUL 2021. (13/20094-0)

BALDIN, EDSON L. L.; DIAS, HERBERT J.; DE SOUZA, CAMILA M.; SOARES, MURIEL C. E.; GRUNDMAN, CARLISMARI O.; SANTOS, THAIS L. B.; CROTTI, ANTONIO E. M.. Insecticidal and inhibitory effects of dihydrobenzofuran neolignans on Bemisia tabaci. JOURNAL OF PEST SCIENCE, v. 92, n. 2, p. 861-869, MAR 2019. (16/16957-0, 13/20094-0)

DIAS, HERBERT J.; BENTO, MARIANA V. B.; DA SILVA, EDER H.; SATURNINO-JUNIOR, ANDRADE; DE OLIVEIRA, MARCELO F.; VESSECCHI, RICARDO; PARREIRA, RENATO L. T.; CROTTI, ANTONIO E. M.. Gas-phase fragmentation reactions of protonated cocaine: New details to an old story. Journal of Mass Spectrometry, v. 53, n. 3, p. 203-213, MAR 2018. (13/20094-0)

SILVA, MARCIO L. A. E; PEREIRA, ANA C.; FERREIRA, DANIELE S.; ESPERANDIM, VIVIANE R.; SIMARO, GUILHERME V.; LIMA, THAIS C.; JANUARIO, ANA H.; PAULETTI, PATRICIA M.; REHDER, VERA L. G.; CREVELIN, EDUARDO J.; et al. In vitro Activities of Pfaffia glomerata Root Extract, Its Hydrolyzed Fractions and Pfaffic Acid Against Trypanosoma cruzi Trypomastigotes. CHEMISTRY & BIODIVERSITY, v. 14, n. 1, JAN 2017. (13/20094-0)

AGUIAR, GABRIELA P.; CREVELIN, EDUARDO J.; DIAS, HERBERT J.; AMBROSIO, SERGIO R.; BASTOS, JAIRO K.; HELENO, VLADIMIR C. G.; VESSECCHI, RICARDO; CROTTI, ANTONIO E. M.. Electrospray ionization tandem mass spectrometry of labdane-type acid diterpenes. Journal of Mass Spectrometry, v. 53, n. 11, p. 1086-1096, NOV 2018. (13/20094-0, 11/13630-7, 12/22832-5, 14/23604-1)

DIAS, HERBERT J.; CREVELIN, EDUARDO J.; PALARETTI, VINICIUS; VESSECCHI, RICARDO; CROTTI, ANTONIO E. M.. Electrospray ionization tandem mass spectrometry of deprotonated dihydrobenzofuran neolignans. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, v. 35, n. 3, FEB 15 2021. (13/20094-0)

DIAS, HERBERT J.; BAGUENARD, MANON; CREVELIN, EDUARDO J.; PALARETTI, VINICIUS; GATES, PAUL J.; VESSECCHI, RICARDO; CROTTI, ANTONIO E. M.. Gas-phase fragmentation reactions of protonated benzofuran- and dihydrobenzofuran-type neolignans investigated by accurate-mass electrospray ionization tandem mass spectrometry. Journal of Mass Spectrometry, v. 54, n. 1, p. 35-46, JAN 2019. (14/23604-1, 13/20094-0)

FUKUI, MURILO J.; DIAS, HERBERT J.; SEVERIANO, MARCELA E.; DE SOUZA, MARIA G. M.; DE OLIVEIRA, POLLYANNA F.; AMBROSIO, SERGIO R.; MARTINS, CARLOS H. G.; TAVARES, DENISE C.; CROTTI, ANTONIO E. M.. Antimicrobial and Cytotoxic Activity of Dihydrobenzofuran Neolignans. CHEMISTRYSELECT, v. 3, n. 6, p. 1836-1839, FEB 14 2018. (13/20094-0, 09/12202-1)

DIAS, HERBERT J.; PATROCINIO, ANDRESSA B.; PAGOTTI, MARIANA C.; FUKUI, MURILO J.; RODRIGUES, VANDERLEI; MAGALHAES, LIZANDRA G.; CROTTI, ANTONIO E. M.. Schistosomicidal Activity of Dihydrobenzofuran Neolignans. CHEMISTRY & BIODIVERSITY, v. 15, n. 7, JUL 2018. (13/20094-0, 09/12202-1, 13/11164-4, 16/24456-1, 14/50265-3)

DEMARQUE, DANIEL P.; CROTTI, ANTONIO E. M.; VESSECCHI, RICARDO; LOPES, JOAO L. C.; LOPES, NORBERTO P.. Fragmentation reactions using electrospray ionization mass spectrometry: an important tool for the structural elucidation and characterization of synthetic and natural products. NATURAL PRODUCT REPORTS, v. 33, n. 3, p. 432-455, 2016. (13/20094-0, 14/23604-1, 14/20302-4, 14/18052-0, 14/50265-3)