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

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)

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Scientific publications (20)
(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)
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, . (09/12202-1, 13/20094-0, 11/07623-8)
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, . (13/20094-0, 09/12202-1)
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, . (13/20094-0, 14/23604-1)
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, . (13/20094-0)
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, . (14/20302-4, 13/20094-0, 14/23604-1, 14/50265-3, 14/18052-0)
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, . (13/20094-0, 11/13630-7, 14/23604-1, 12/22832-5)
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, . (13/20094-0)
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, . (13/11164-4, 16/24456-1, 13/20094-0, 09/12202-1, 14/50265-3)
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, . (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, . (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, p. -, . (13/20094-0, 14/08905-5)
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, . (16/16957-0, 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, . (14/23604-1, 13/20094-0)
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, . (13/20094-0, 16/19272-9)
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, . (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, . (13/20094-0, 09/51145-3)
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, . (13/20094-0, 12/06931-3, 13/50729-7)
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, . (14/50265-3, 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, . (13/20094-0, 14/23604-1)
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, . (13/20094-0, 13/17658-9, 16/07597-0)

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