Publication: An in silico investigation of menthol metabolism
Issued Date
2019-01-01
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19326203
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2-s2.0-85072702262
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Mahidol University
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SCOPUS
Bibliographic Citation
PLoS ONE. Vol.14, No.9 (2019)
Suggested Citation
Taweetham Limpanuparb, Wanutcha Lorpaiboon, Kridtin Chinsukserm An in silico investigation of menthol metabolism. PLoS ONE. Vol.14, No.9 (2019). doi:10.1371/journal.pone.0216577 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/49845
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Title
An in silico investigation of menthol metabolism
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Abstract
© 2019 Limpanuparb et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Prevalence of mentholated products for consumption has brought great importance to studies on menthol’s metabolic pathways to ensure safety, design more potent derivatives, and identify therapeutic benefits. Proposed pathways of (-)-menthol metabolism based on metabolites found experimentally in previous works by Yamaguchi, Caldwell & Farmer, Madyastha & Srivatsan and Hiki et al. were not in agreement. This in silico approach is based on the three in vivo studies and aims to resolve the discrepancies. Reactions in the pathways are conjugation with glucuronic acid/sulfate, oxidation to alcohol, aldehyde & carboxylic acid, and formation of a four-membered/five-membered ring. Gas-phase structures, standard Gibbs energies and SMD solvation energies at B3LYP/6-311++G(d,p) level were obtained for 102 compounds in the pathways. This study provides a more complete picture of menthol metabolism by combining information from three experimental studies and filling missing links in previously published pathways.