Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from Plants
Menthol is a cyclic monoterpene alcohol of the essential oils of plants of the genus <i>Mentha</i>, which is in demand by various industries due to its diverse sensorial and physiological properties. However, its poor water solubility and its toxic effect limit possible applications. Gly...
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doaj-65171cfd719c4f93a9be82923ade6d8d2021-09-26T00:46:05ZengMDPI AGMolecules1420-30492021-09-01265511551110.3390/molecules26185511Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from PlantsElisabeth Kurze0Victoria Ruß1Nadia Syam2Isabelle Effenberger3Rafal Jonczyk4Jieren Liao5Chuankui Song6Thomas Hoffmann7Wilfried Schwab8Biotechnology of Natural Products, School of Life Sciences, Technical University of Munich, Liesel-Beckmann-Str. 1, 85354 Freising, GermanyBiotechnology of Natural Products, School of Life Sciences, Technical University of Munich, Liesel-Beckmann-Str. 1, 85354 Freising, GermanyBiotechnology of Natural Products, School of Life Sciences, Technical University of Munich, Liesel-Beckmann-Str. 1, 85354 Freising, Germany4GENE, Lise-Meitner-Straße 30, 85354 Freising, GermanyBiotechnology of Natural Products, School of Life Sciences, Technical University of Munich, Liesel-Beckmann-Str. 1, 85354 Freising, GermanyBiotechnology of Natural Products, School of Life Sciences, Technical University of Munich, Liesel-Beckmann-Str. 1, 85354 Freising, GermanyState Key Laboratory of Tea Plant Biology and Utilization, International Joint Laboratory on Tea Chemistry and Health Effects, Anhui Agricultural University, Hefei 230036, ChinaBiotechnology of Natural Products, School of Life Sciences, Technical University of Munich, Liesel-Beckmann-Str. 1, 85354 Freising, GermanyBiotechnology of Natural Products, School of Life Sciences, Technical University of Munich, Liesel-Beckmann-Str. 1, 85354 Freising, GermanyMenthol is a cyclic monoterpene alcohol of the essential oils of plants of the genus <i>Mentha</i>, which is in demand by various industries due to its diverse sensorial and physiological properties. However, its poor water solubility and its toxic effect limit possible applications. Glycosylation offers a solution as the binding of a sugar residue to small molecules increases their water solubility and stability, renders aroma components odorless and modifies bioactivity. In order to identify plant enzymes that catalyze this reaction, a glycosyltransferase library containing 57 uridine diphosphate sugar-dependent enzymes (UGTs) was screened with (±)-menthol. The identity of the products was confirmed by mass spectrometry and nuclear magnetic resonance spectroscopy. Five enzymes were able to form (±)-menthyl-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside in whole-cell biotransformations: UGT93Y1, UGT93Y2, UGT85K11, UGT72B27 and UGT73B24. In vitro enzyme activity assays revealed highest catalytic activity for UGT93Y1 (7.6 nkat/mg) from <i>Camellia sinensis</i> towards menthol and its isomeric forms. Although UGT93Y2 shares 70% sequence identity with UGT93Y1, it was less efficient. Of the five enzymes, UGT93Y1 stood out because of its high in vivo and in vitro biotransformation rate. The identification of novel menthol glycosyltransferases from the tea plant opens new perspectives for the biotechnological production of menthyl glucoside.https://www.mdpi.com/1420-3049/26/18/5511<i>Camellia sinensis</i>UDP-glucosyltransferaseUGT93Y1mentholmenthyl glucoside |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Elisabeth Kurze Victoria Ruß Nadia Syam Isabelle Effenberger Rafal Jonczyk Jieren Liao Chuankui Song Thomas Hoffmann Wilfried Schwab |
spellingShingle |
Elisabeth Kurze Victoria Ruß Nadia Syam Isabelle Effenberger Rafal Jonczyk Jieren Liao Chuankui Song Thomas Hoffmann Wilfried Schwab Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from Plants Molecules <i>Camellia sinensis</i> UDP-glucosyltransferase UGT93Y1 menthol menthyl glucoside |
author_facet |
Elisabeth Kurze Victoria Ruß Nadia Syam Isabelle Effenberger Rafal Jonczyk Jieren Liao Chuankui Song Thomas Hoffmann Wilfried Schwab |
author_sort |
Elisabeth Kurze |
title |
Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from Plants |
title_short |
Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from Plants |
title_full |
Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from Plants |
title_fullStr |
Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from Plants |
title_full_unstemmed |
Glucosylation of (±)-Menthol by Uridine-Diphosphate-Sugar Dependent Glucosyltransferases from Plants |
title_sort |
glucosylation of (±)-menthol by uridine-diphosphate-sugar dependent glucosyltransferases from plants |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2021-09-01 |
description |
Menthol is a cyclic monoterpene alcohol of the essential oils of plants of the genus <i>Mentha</i>, which is in demand by various industries due to its diverse sensorial and physiological properties. However, its poor water solubility and its toxic effect limit possible applications. Glycosylation offers a solution as the binding of a sugar residue to small molecules increases their water solubility and stability, renders aroma components odorless and modifies bioactivity. In order to identify plant enzymes that catalyze this reaction, a glycosyltransferase library containing 57 uridine diphosphate sugar-dependent enzymes (UGTs) was screened with (±)-menthol. The identity of the products was confirmed by mass spectrometry and nuclear magnetic resonance spectroscopy. Five enzymes were able to form (±)-menthyl-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside in whole-cell biotransformations: UGT93Y1, UGT93Y2, UGT85K11, UGT72B27 and UGT73B24. In vitro enzyme activity assays revealed highest catalytic activity for UGT93Y1 (7.6 nkat/mg) from <i>Camellia sinensis</i> towards menthol and its isomeric forms. Although UGT93Y2 shares 70% sequence identity with UGT93Y1, it was less efficient. Of the five enzymes, UGT93Y1 stood out because of its high in vivo and in vitro biotransformation rate. The identification of novel menthol glycosyltransferases from the tea plant opens new perspectives for the biotechnological production of menthyl glucoside. |
topic |
<i>Camellia sinensis</i> UDP-glucosyltransferase UGT93Y1 menthol menthyl glucoside |
url |
https://www.mdpi.com/1420-3049/26/18/5511 |
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