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.
CITATION STYLE
Choi, H. Y., Kim, B. M., Morgan, A. M. A., Kim, J. S., & Kim, W. G. (2017). Improvement of the pharmacological activity of menthol via enzymatic β-anomer-selective glycosylation. AMB Express, 7(1). https://doi.org/10.1186/s13568-017-0468-0
Mendeley helps you to discover research relevant for your work.