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Toxins 2017, 9(1), 35; doi:10.3390/toxins9010035

Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus flavus by UHPLC Triple-TOF HRMS

1
Laboratory of Food Analysis, Faculty of Pharmaceutical Sciences, Ghent University, Ottergemsesteenweg 460, 9000 Ghent, Belgium
2
Department of Pharmacy, Faculty of Medicine, University of Prishtina, Rrethi i Spitalit p.n, 10000 Prishtina, Kosovo
3
Southern Regional Research Center, Agricultural Research Service, United States Department of Agriculture (ARS-USDA), New Orleans, 70124 LA, USA
4
Department of Analytical Chemistry, Faculty of Sciences, University of Granada, Campus Fuentenueva s/n, E-18071 Granada, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Massimo Reverberi
Received: 9 November 2016 / Revised: 20 December 2016 / Accepted: 10 January 2017 / Published: 13 January 2017
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Abstract

Cyclopiazonic acid (α-cyclopiazonic acid, α-CPA) is an indole-hydrindane-tetramic acid neurotoxin produced by various fungal species, including the notorious food and feed contaminant Aspergillus flavus. Despite its discovery in A. flavus cultures approximately 40 years ago, its contribution to the A. flavus mycotoxin burden is consistently minimized by our focus on the more potent carcinogenic aflatoxins also produced by this fungus. Here, we report the screening and identification of several CPA-type alkaloids not previously found in A. flavus cultures. Our identifications of these CPA-type alkaloids are based on a dereplication strategy involving accurate mass high resolution mass spectrometry data and a careful study of the α-CPA fragmentation pattern. In total, 22 CPA-type alkaloids were identified in extracts from the A. flavus strains examined. Of these metabolites, 13 have been previously reported in other fungi, though this is the first report of their existence in A. flavus. Two of our metabolite discoveries, 11,12-dehydro α-CPA and 3-hydroxy-2-oxo CPA, have never been reported for any organism. The conspicuous presence of CPA and its numerous derivatives in A. flavus cultures raises concerns about the long-term and cumulative toxicological effects of these fungal secondary metabolites and their contributions to the entire A. flavus mycotoxin problem. View Full-Text
Keywords: cyclopiazonic acid; ergot-like alkaloid; dereplication; HRMS cyclopiazonic acid; ergot-like alkaloid; dereplication; HRMS
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Uka, V.; Moore, G.G.; Arroyo-Manzanares, N.; Nebija, D.; De Saeger, S.; Diana Di Mavungu, J. Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus flavus by UHPLC Triple-TOF HRMS. Toxins 2017, 9, 35.

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