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Unravelling the diversity of the cyclopiazonic acid family of mycotoxins in Aspergillus flavus by UHPLC triple-TOF HRMS

(2017) TOXINS. 9(1).
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Abstract
Cyclopiazonic acid (alpha-cyclopiazonic acid, alpha-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 alpha-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 alpha-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.
Keywords
REDUCE AFLATOXIN CONTAMINATION, GENE-CLUSTER, PENICILLIUM-CYCLOPIUM, OXINDOLE ALKALOIDS, MASS-SPECTROMETRY, PKS-NRPS, SECONDARY METABOLITES, BIOSYNTHESIS, ORYZAE, RECOMBINATION, cyclopiazonic acid, ergot-like alkaloid, dereplication, HRMS

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Chicago
Uka, Valdet, Geromy G Moore, Natalia Arroyo Manzanares, Dashnor Nebija, Sarah De Saeger, and José Diana Di Mavungu. 2017. “Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus Flavus by UHPLC triple-TOF HRMS.” Toxins 9 (1).
APA
Uka, V., Moore, G. G., Arroyo Manzanares, N., Nebija, D., De Saeger, S., & Diana Di Mavungu, J. (2017). Unravelling the diversity of the cyclopiazonic acid family of mycotoxins in Aspergillus flavus by UHPLC triple-TOF HRMS. TOXINS, 9(1).
Vancouver
1.
Uka V, Moore GG, 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(1).
MLA
Uka, Valdet, Geromy G Moore, Natalia Arroyo Manzanares, et al. “Unravelling the Diversity of the Cyclopiazonic Acid Family of Mycotoxins in Aspergillus Flavus by UHPLC triple-TOF HRMS.” TOXINS 9.1 (2017): n. pag. Print.
@article{8518151,
  abstract     = {Cyclopiazonic acid (alpha-cyclopiazonic acid, alpha-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 alpha-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 alpha-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.},
  articleno    = {35},
  author       = {Uka, Valdet and Moore, Geromy G and Arroyo Manzanares, Natalia and Nebija, Dashnor and De Saeger, Sarah and Diana Di Mavungu, Jos{\'e}},
  issn         = {2072-6651},
  journal      = {TOXINS},
  language     = {eng},
  number       = {1},
  pages        = {21},
  title        = {Unravelling the diversity of the cyclopiazonic acid family of mycotoxins in Aspergillus flavus by UHPLC triple-TOF HRMS},
  url          = {http://dx.doi.org/10.3390/toxins9010035},
  volume       = {9},
  year         = {2017},
}

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