Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation

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Title
Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation
Author(s)
Ha Young Choi; Bo Min Kim; A M A Morgan; Joong Su KimWon Gon Kim
Bibliographic Citation
AMB Express, vol. 7, pp. 167-167
Publication Year
2017
Abstract
Menthol has a considerable cooling effect, but the use range of menthol is limited because of its extremely low solubility in water and inherent flavor. (-)-Menthol β-glucoside was determined to be more soluble in water (>27 times) than (-)-menthol α-glucoside; hence, β-anomer-selective glucosylation of menthol is necessary. The in vitro glycosylation of (-)-menthol by uridine diphosphate glycosyltransferase (BLC) from Bacillus licheniformis generated (-)-menthol β-glucoside and new (-)-menthol β-galactoside and (-)-menthol N-acetylglucosamine. The maximum conversion rate of menthol to (-)-menthol β-d-glucoside by BLC was found to be 58.9%. Importantly, (-)-menthol β-d-glucoside had a higher cooling effect and no flavor compared with menthol. In addition, (-)-menthol β-d-glucoside was determined to be a non-sensitizer in a skin allergy test in the human cell line activation test, whereas menthol was a sensitizer.
Keyword
CoolingGlycosyltransferaseMentholMenthol β-glycosidesSolubility
ISSN
2191-0855
Publisher
Springer
DOI
http://dx.doi.org/10.1186/s13568-017-0468-0
Type
Article
Appears in Collections:
Division of Bio Technology Innovation > SME Support Center > 1. Journal Articles
Division of Research on National Challenges > Infectious Disease Research Center > 1. Journal Articles
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