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Molecules 2013, 18(3), 2528-2538; doi:10.3390/molecules18032528

Identification of Alternaria alternata Mycotoxins by LC-SPE-NMR and Their Cytotoxic Effects to Soybean (Glycine max) Cell Suspension Culture

1
Laboratório de Bioquímica Micromolecular de Micro-organismos, Departamento de Química, Universidade Federal de São Carlos-UFSCar, Rodovia Washington Luiz, Km 235, 676 São Carlos-SP, Brazil
2
Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena D-07745, Germany
3
Accert Chemistry and Biotechnology Inc., Rua Alfredo Lopes 1717, São Carlos-SP, Brazil
4
Biosynthesis/NMR Research Group, Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, Jena D-07745, Germany
5
NMR Applications Group, Bruker Biospin GmbH, Silberstreifen 4, Rheinstetten 76287, Germany
*
Author to whom correspondence should be addressed.
Received: 13 December 2012 / Revised: 29 January 2013 / Accepted: 16 February 2013 / Published: 26 February 2013
(This article belongs to the Special Issue Bioassay-Guided Isolation of Natural Products)
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Abstract

This present work describes the application of liquid chromatograpy-solid phase extraction-nuclear magnetic resonance spectroscopy to analyse Alternaria alternata crude extracts. Altenusin (1), alternariol (2), 3'-hydroxyalternariol monomethyl ether (3), and alternariol monomethyl ether (4), were separated and identified. High-resolution mass spectrometry confirmed the proposed structures. The cytotoxic effects of these compounds towards plants were determined using soybean (Glycine max) cell cultures as a model. EC50 values which range from 0.11 (±0.02) to 4.69 (±0.47) μM showed the high cytotoxicity of these compounds.
Keywords: LC-NMR; LC-SPE-NMR; mass spectrometry; alternariol; Alternaria; soybean; Glycine max; cell cultures; cytotoxicity LC-NMR; LC-SPE-NMR; mass spectrometry; alternariol; Alternaria; soybean; Glycine max; cell cultures; cytotoxicity
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MDPI and ACS Style

de Souza, G.D.; Mithöfer, A.; Daolio, C.; Schneider, B.; Rodrigues-Filho, E. Identification of Alternaria alternata Mycotoxins by LC-SPE-NMR and Their Cytotoxic Effects to Soybean (Glycine max) Cell Suspension Culture. Molecules 2013, 18, 2528-2538.

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