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• de Souza, GD.
• Mithöfer, A
• Daolio, C
• Schneider, B
• Rodrigues-Filho, E
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• de Souza, GD.
• Mithöfer, A
• Daolio, C
• Schneider, B
• Rodrigues-Filho, E
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• de Souza, GD.
• Mithöfer, A
• Daolio, C
• Schneider, B
• Rodrigues-Filho, E

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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

Gezimar D. de Souza ^1,2,3,* , Axel Mithöfer ² , Cristina Daolio ^4,5 , Bernd Schneider ⁴  and Edson Rodrigues-Filho 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; in revised form: 29 January 2013 / Accepted: 16 February 2013 / Published: 26 February 2013

(This article belongs to the Special Issue Bioassay-Guided Isolation of Natural Products)

Download PDF Full-Text [484 KB, uploaded 26 February 2013 08:26 CET]

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

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