Structural Chemistry

, Volume 30, Issue 5, pp 1749–1759 | Cite as

Quantum chemical investigation of the detection properties of alternariol and alternariol monomethyl ether

  • Yi-Shu Tu
  • Yufeng J. Tseng
  • Michael AppellEmail author
Original Research


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.


Alternariol Computational chemistry Mycotoxins Density functional theory (DFT) 



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.


This research was funded by the Ministry of Science and Technology grant number 106-2917-I-564-017.

Compliance with ethical standards

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.

Supplementary material

11224_2019_1302_MOESM1_ESM.docx (1.3 mb)
ESM 1 (DOCX 1358 kb)


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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.The Postdoctoral Research Abroad ProgramMinistry of Science and TechnologyTaipeiTaiwan
  2. 2.Mycotoxin Prevention and Applied Microbiology Research, National Center of Agricultural Utilization ResearchUS Department of Agriculture, Agricultural Research ServicePeoriaUSA
  3. 3.Graduate Institute of Biomedical Electronics and BioinformaticsNational Taiwan UniversityTaipeiTaiwan
  4. 4.Department of Computer Science and Information EngineeringNational Taiwan UniversityTaipeiTaiwan

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