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

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

1,2,3,* , 2
,
4,5
,
4
 and
1
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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