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

作者: Valdet Uka , Geromy Moore , Natalia Arroyo-Manzanares , Dashnor Nebija , Sarah De Saeger

DOI: 10.3390/TOXINS9010035

关键词:

摘要: Cyclopiazonic acid (α-cyclopiazonic acid, α-CPA) is an indole-hydrindane-tetramic 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, contribution to mycotoxin burden consistently minimized our focus on more potent carcinogenic aflatoxins also this fungus. Here, we report screening identification of several CPA-type alkaloids not previously found cultures. Our identifications these are based a dereplication strategy involving accurate mass high resolution spectrometry data careful study α-CPA fragmentation pattern. In total, 22 were identified extracts from strains examined. Of metabolites, 13 have been reported other fungi, though first their existence Two metabolite discoveries, 11,12-dehydro 3-hydroxy-2-oxo CPA, never for any organism. The conspicuous presence CPA numerous derivatives raises concerns about long-term cumulative toxicological effects secondary metabolites contributions entire problem.

参考文章(65)
MARÍA J. SOSA, JUAN J. CÓRDOBA, CARMEN DÍAZ, MAR RODRÍGUEZ, ELENA BERMÚDEZ, MIGUEL A. ASENSIO, FÉLIX NÚÑEZ, Production of cyclopiazonic acid by Penicillium commune isolated from dry-cured ham on a meat extract-based substrate. Journal of Food Protection. ,vol. 65, pp. 988- 992 ,(2002) , 10.4315/0362-028X-65.6.988
O. V. Nevzglyadova, A. A. Gaivoronskii, A. V. Artemov, T. I. Smirnova, T. R. Soidla, Detection of Concealed “Illegitimate” Nuclei in Tetrad Analysis of the Diploid Progeny of Heterokaryons in Saccharomyces cerevisiae Russian Journal of Genetics. ,vol. 37, pp. 617- 623 ,(2001) , 10.1023/A:1016665022488
J W Dorner, Production of cyclopiazonic acid by Aspergillus tamarii Kita. Applied and Environmental Microbiology. ,vol. 46, pp. 1435- 1437 ,(1983) , 10.1128/AEM.46.6.1435-1437.1983
K C Luk, B Kobbe, J M Townsend, Production of cyclopiazonic acid by Aspergillus flavus Link. Applied and Environmental Microbiology. ,vol. 33, pp. 211- 212 ,(1977) , 10.1128/AEM.33.1.211-212.1977
Norbert W Seidler, I Jona, M Vegh, Anthony Martonosi, None, Cyclopiazonic acid is a specific inhibitor of the Ca2+-ATPase of sarcoplasmic reticulum. Journal of Biological Chemistry. ,vol. 264, pp. 17816- 17823 ,(1989) , 10.1016/S0021-9258(19)84646-X
J. Lytton, M. Westlin, M.R. Hanley, Thapsigargin inhibits the sarcoplasmic or endoplasmic reticulum Ca-ATPase family of calcium pumps. Journal of Biological Chemistry. ,vol. 266, pp. 17067- 17071 ,(1991) , 10.1016/S0021-9258(19)47340-7
Masafumi Tokuoka, Tomoki Kikuchi, Yasutomo Shinohara, Akifumi Koyama, Shin-ichiro Iio, Takaaki Kubota, Jun’ichi Kobayashi, Yasuji Koyama, Akira Totsuka, Hitoshi Shindo, Kazuo Sato, Cyclopiazonic acid biosynthesis gene cluster gene cpaM is required for speradine A biosynthesis Bioscience, Biotechnology, and Biochemistry. ,vol. 79, pp. 2081- 2085 ,(2015) , 10.1080/09168451.2015.1065167
Jeffrey W. Cary, Valdet Uka, Zheng Han, Dieter Buyst, Pamela Y. Harris-Coward, Kenneth C. Ehrlich, Qijian Wei, Deepak Bhatnagar, Patrick F. Dowd, Stacey L. Martens, Ana M. Calvo, José C. Martins, Lynn Vanhaecke, Tom Coenye, Sarah De Saeger, José Diana Di Mavungu, An Aspergillus flavus secondary metabolic gene cluster containing a hybrid PKS–NRPS is necessary for synthesis of the 2-pyridones, leporins Fungal Genetics and Biology. ,vol. 81, pp. 88- 97 ,(2015) , 10.1016/J.FGB.2015.05.010
N. Arroyo-Manzanares, J. Diana Di Mavungu, V. Uka, L. Gámiz-Gracia, A.M. García-Campaña, S. De Saeger, An integrated targeted and untargeted approach for the analysis of ergot alkaloids in cereals using UHPLC – hybrid quadrupole time-of-flight mass spectrometry World Mycotoxin Journal. ,vol. 8, pp. 653- 666 ,(2015) , 10.3920/WMJ2015.1900
Hucheng Zhu, Chunmei Chen, Jianping Wang, Xiao‐Nian Li, Guangzheng Wei, Yi Guo, Guangmin Yao, Zengwei Luo, Jinwen Zhang, Yongbo Xue, Yonghui Zhang, Penicamedine A, a Highly Oxygenated Hexacyclic Indole Alkaloid from Penicillium camemberti Chemistry & Biodiversity. ,vol. 12, pp. 1547- 1553 ,(2015) , 10.1002/CBDV.201400412