Abstract
Alternariol and alternariol monomethyl ether are mycotoxins occasionally found in food and beverages that have been contaminated by certain fungi of the Alternaria genus. Conformers, tautomers, anions, and analogs of alternariol were geometry optimized using the Becke, three-parameter, Lee-Yang-Parr (B3LYP) density functional. Electronic structural analysis provided frontier orbitals, molecular electronic potential maps, and vibrational assignments. Optimized conformations of alternariol are within 5.2 kJ mol−1 of the most stable conformation and share very similar molecular orbital properties. Vibrational assignments for the calculated infrared and Raman spectra are reported and correspond with experimental spectra. Tautomers are 130–180 kJ mol−1 higher in energy and possess unique molecular orbital properties. Methylated and demethylated analogs shared similar properties to alternariol. Deprotonation of hydroxyl groups of alternariol, alternariol monomethyl ether, and methylated analogs influences the molecular orbital properties and molecular electrostatic potential maps.
Similar content being viewed by others
Data availability
The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.
References
Alassane-Kpembi I, Schatzmayr G, Taranu I, Marin D, Puel O, Iswald IP (2017) Crit Rev Food Sci Nutr 57:3489
Gruber-Dorninger C, Novak B, Nagl V, Berthiller F (2017) J Agric Food Chem 65:7052
Solfrizzo M (2017) Curr Opin Food Sci. https://doi.org/10.1016/j.cofs.2017.09.012
Escrivá L, Oueslati S, Font G, Manyes L (2017) J Food Qual. https://doi.org/10.1155/2017/1569748
Solhaug A, Eriksen GS, Holme JA (2016) Basic Clin Pharmacol Toxicol 119:533
European Commission (2012) Mandate for standardization addressed to CEN for thods of analysis for mycotoxins in food. In: Union E (ed) European Commission mandate (EC) M/520EN. Brussels, pp 221/223–221/236
Man Y, Liang G, Li A, Pan L (2017) Chromatographia 80:9
Rico-Yuste A, Walravens J, Urraca JL, Abou-Hany RAG, Descalzo AB, Orellana G, Rychlik M, De Saeger S, Moreno-Bondi MC (2018) Food Chem 243:357
Mirchi A, Sizochenko N, Leszczynski J (2018) Struct Chem 29:765
Kolesov G, Grånäs O, Hoyt R, Vinichenko D, Kaxiras E (2016) J Chem Theory Comput 12(2):466
Appell M, Evans KO, Compton DL, Wang LC, Bosma WB (2018) Struct Chem 29:715
Manojai N, Daengngern R, Kerdpol K, Ngaojampa C, Kungwan N (2017) J Lumin 188:275
Abuelela AM, Alodail FA, Al-Shihry SS, Prezhdo OV (2018) Struct Chem 29:1085
Li J, Luo Y, Zhang J (2018) Spectrochim Acta A 205:520
Cvijetić IN, Pešić MP, Todorov MD, DrakulićIvan BJ, Juranić IO, Verbić TZ, Zloh M (2018) Struct Chem 29:423
Garrido-Arandia M, Gómez-Casado C, Díaz-Perales A, Pacios LF (2014) J Mol Graph 53:140
Scharkoi O, Fackeldey K, Merkulow I, Andrae K, Weber M, Nehls I, Siegel D (2013) J Mol Model 19(6):2567
Andersson MP, Uvdal P (2015) J Chem Theory Comput 11:5371
Steward JJP (1989) Optimization of parameters for semiempirical methods II. Applications. J Comput Chem 10:221
Hypercube Inc. (2011) Hyperchem professional 8.0.10. Gainesville
O’Boyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR (2011) Open babel: an open chemical toolbox. J Cheminform 3(1):33
Liu J, Thiel W (2018) J Chem Phys 148(15):154103
Shao Y, Molnar LF, Jung Y et al (2006) Phys Chem Chem Phys 8:3172
Valiev M, Bylaska EJ, Govind N, Kowalski K, Straatsma TP, Van Dam HJJ, Wang D, Nieplocha J, Apra E, Windus TL, de Jong WA (2010) Comput Phys Commun 181:1477
Fischer SA, Ueltschi TW, El-Khoury PZ, Mifflin AL, Hess WP, Wang HF, Cramer CJ, Govind N (2016) J Phys Chem B 120(8):1429
Pan T-T, Sun D-W, Pu H, Wei Q (2018) J Agric Food Chem 66:2180
Jarolim K, Del Favero G, Ellmer D, Stark TD, Hofmann T, Sulyok M, Humpf H-U, Marko D (2017) Arch Toxicol 91:2007
Tiessen C, Gehrke H, Kropat C, Schwarz C, Bächler S, Fehr M, Pahlke G, Marko D (2013) World Mycotoxin J 6:233
Acknowledgments
Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the US Department of Agriculture (USDA). USDA is an equal opportunity provider and employer.
Funding
This research was funded by the Ministry of Science and Technology grant number 106-2917-I-564-017.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Ethical statement
All authors certify and assert that no animals or humans were used to obtain results reported in this research.
Additional information
Publisher’s note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
ESM 1
(DOCX 1358 kb)
Rights and permissions
About this article
Cite this article
Tu, YS., Tseng, Y.J. & Appell, M. Quantum chemical investigation of the detection properties of alternariol and alternariol monomethyl ether. Struct Chem 30, 1749–1759 (2019). https://doi.org/10.1007/s11224-019-01302-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-019-01302-3