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AMB Express. 2017 Aug 29;7(1):167. doi: 10.1186/s13568-017-0468-0.

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

Author information

1
Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology, Yusong, Daejeon, 305-806, Republic of Korea.
2
Department of Bio-Molecular Science, KRIBB School of Bioscience, Korea University of Science and Technology (UST), Yusong, Daejeon, Republic of Korea.
3
Infection Control Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup-si, Jeollabuk-do, 56212, Republic of Korea.
4
Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology, Yusong, Daejeon, 305-806, Republic of Korea. wgkim@kribb.re.kr.
5
Department of Bio-Molecular Science, KRIBB School of Bioscience, Korea University of Science and Technology (UST), Yusong, Daejeon, Republic of Korea. wgkim@kribb.re.kr.

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.

KEYWORDS:

Cooling; Glycosyltransferase; Menthol; Menthol β-glycosides; Solubility

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