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通过酶促β-端基异构体选择性糖基化改善薄荷醇的药理活性。

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

作者信息

Choi Ha-Young, Kim Bo-Min, Morgan Abubaker M A, Kim Joong Su, Kim Won-Gon

机构信息

Superbacteria Research Center, Korea Research Institute of Bioscience and Biotechnology, Yusong, Daejeon, 305-806, Republic of Korea.

Department of Bio-Molecular Science, KRIBB School of Bioscience, Korea University of Science and Technology (UST), Yusong, Daejeon, Republic of Korea.

出版信息

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

DOI:10.1186/s13568-017-0468-0
PMID:28853018
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5574827/
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.

摘要

薄荷醇具有显著的清凉效果，但由于其在水中的溶解度极低且具有固有风味，薄荷醇的使用范围受到限制。已确定（-）-薄荷醇β-葡萄糖苷在水中的溶解度比（-）-薄荷醇α-葡萄糖苷高（>27倍）；因此，薄荷醇的β-异头物选择性糖基化是必要的。地衣芽孢杆菌的尿苷二磷酸糖基转移酶（BLC）对（-）-薄荷醇进行体外糖基化反应，生成了（-）-薄荷醇β-葡萄糖苷以及新的（-）-薄荷醇β-半乳糖苷和（-）-薄荷醇N-乙酰葡糖胺。发现BLC将薄荷醇转化为（-）-薄荷醇β-D-葡萄糖苷的最大转化率为58.9%。重要的是，与薄荷醇相比，（-）-薄荷醇β-D-葡萄糖苷具有更高的清凉效果且无风味。此外，在人体细胞系激活试验的皮肤过敏试验中，（-）-薄荷醇β-D-葡萄糖苷被确定为非致敏剂，而薄荷醇是致敏剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/9c27d46bf64a/13568_2017_468_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/040f0221c187/13568_2017_468_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/6a0f4cbea659/13568_2017_468_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/24b38fec0d76/13568_2017_468_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/84e4c9bb8d40/13568_2017_468_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/9c27d46bf64a/13568_2017_468_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/040f0221c187/13568_2017_468_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/6a0f4cbea659/13568_2017_468_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/24b38fec0d76/13568_2017_468_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/84e4c9bb8d40/13568_2017_468_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/83db/5574827/9c27d46bf64a/13568_2017_468_Fig5_HTML.jpg

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