Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in Water
Baicalin is a biologically active flavone glucuronide with poor water solubility that can be enhanced via glucosylation. In this study, the transglucosylation of baicalin was successfully achieved with CGTases from <i>Thermoanaerobacter</i> sp. and <i>Bacillus macerans</i> us...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/9/3891 |
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| author | Carole Lambert Perrine Lemagnen Eglantine Don Simoni Jane Hubert Alexis Kotland Chantal Paulus Audrey De Bizemont Sylvie Bernard Anne Humeau Daniel Auriol Romain Reynaud |
| author_facet | Carole Lambert Perrine Lemagnen Eglantine Don Simoni Jane Hubert Alexis Kotland Chantal Paulus Audrey De Bizemont Sylvie Bernard Anne Humeau Daniel Auriol Romain Reynaud |
| author_sort | Carole Lambert |
| collection | DOAJ |
| description | Baicalin is a biologically active flavone glucuronide with poor water solubility that can be enhanced via glucosylation. In this study, the transglucosylation of baicalin was successfully achieved with CGTases from <i>Thermoanaerobacter</i> sp. and <i>Bacillus macerans</i> using α-cyclodextrin as a glucosyl donor. The synthesis of baicalin glucosides was optimized with CGTase from <i>Thermoanaerobacter</i> sp. Enzymatically modified baicalin derivatives were α-glucosylated with 1 to 17 glucose moieties. The two main glucosides were identified as Baicalein-7-<i>O</i>-α-D-Glucuronidyl-(1→4′)-<i>O</i>-α-D-Glucopyranoside (BG<sub>1</sub>) and Baicalein-7-<i>O</i>-α-D-Glucuronidyl-(1→4′)-<i>O</i>-α-D-Maltoside (BG<sub>2</sub>), thereby confirming recent findings reporting that glucuronyl groups are acceptors of this CGTase. Optimized conditions allowed for the attainment of yields above 85% (with a total glucoside content higher than 30 mM). BG<sub>1</sub> and BG<sub>2</sub> were purified via centrifugal partition chromatography after an enrichment through deglucosylation with amyloglucosidase. Transglucosylation increased the water solubility of BG<sub>1</sub> by a factor of 188 in comparison to that of baicalin (molar concentrations), while the same value for BG<sub>2</sub> was increased by a factor of 320. Finally, BG<sub>1</sub> and BG<sub>2</sub> were evaluated using antioxidant and anti-glycation assays. Both glucosides presented antioxidant and anti-glycation properties in the same order of magnitude as that of baicalin, thereby indicating their potential biological activity. |
| first_indexed | 2024-03-11T04:11:49Z |
| format | Article |
| id | doaj.art-1587e849cd4942b091145b4d3616e5e2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T04:11:49Z |
| publishDate | 2023-05-01 |
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| spelling | doaj.art-1587e849cd4942b091145b4d3616e5e22023-11-17T23:24:51ZengMDPI AGMolecules1420-30492023-05-01289389110.3390/molecules28093891Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in WaterCarole Lambert0Perrine Lemagnen1Eglantine Don Simoni2Jane Hubert3Alexis Kotland4Chantal Paulus5Audrey De Bizemont6Sylvie Bernard7Anne Humeau8Daniel Auriol9Romain Reynaud10Givaudan France SAS, 31400 Toulouse, FranceGivaudan France SAS, 31400 Toulouse, FranceGivaudan France SAS, 31400 Toulouse, FranceNATEXPLORE SAS, 51140 Prouilly, FranceNATEXPLORE SAS, 51140 Prouilly, FranceGivaudan France SAS, 31400 Toulouse, FranceGivaudan France SAS, 22560 Pleumeur-Bodou, FranceGivaudan France SAS, 22560 Pleumeur-Bodou, FranceGivaudan France SAS, 22560 Pleumeur-Bodou, FranceGivaudan France SAS, 31400 Toulouse, FranceGivaudan France SAS, 31400 Toulouse, FranceBaicalin is a biologically active flavone glucuronide with poor water solubility that can be enhanced via glucosylation. In this study, the transglucosylation of baicalin was successfully achieved with CGTases from <i>Thermoanaerobacter</i> sp. and <i>Bacillus macerans</i> using α-cyclodextrin as a glucosyl donor. The synthesis of baicalin glucosides was optimized with CGTase from <i>Thermoanaerobacter</i> sp. Enzymatically modified baicalin derivatives were α-glucosylated with 1 to 17 glucose moieties. The two main glucosides were identified as Baicalein-7-<i>O</i>-α-D-Glucuronidyl-(1→4′)-<i>O</i>-α-D-Glucopyranoside (BG<sub>1</sub>) and Baicalein-7-<i>O</i>-α-D-Glucuronidyl-(1→4′)-<i>O</i>-α-D-Maltoside (BG<sub>2</sub>), thereby confirming recent findings reporting that glucuronyl groups are acceptors of this CGTase. Optimized conditions allowed for the attainment of yields above 85% (with a total glucoside content higher than 30 mM). BG<sub>1</sub> and BG<sub>2</sub> were purified via centrifugal partition chromatography after an enrichment through deglucosylation with amyloglucosidase. Transglucosylation increased the water solubility of BG<sub>1</sub> by a factor of 188 in comparison to that of baicalin (molar concentrations), while the same value for BG<sub>2</sub> was increased by a factor of 320. Finally, BG<sub>1</sub> and BG<sub>2</sub> were evaluated using antioxidant and anti-glycation assays. Both glucosides presented antioxidant and anti-glycation properties in the same order of magnitude as that of baicalin, thereby indicating their potential biological activity.https://www.mdpi.com/1420-3049/28/9/3891baicalinpolyphenolglucuronidecyclodextrin glucanotransferaseα-cyclodextrinenzymatic glucosylation |
| spellingShingle | Carole Lambert Perrine Lemagnen Eglantine Don Simoni Jane Hubert Alexis Kotland Chantal Paulus Audrey De Bizemont Sylvie Bernard Anne Humeau Daniel Auriol Romain Reynaud Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in Water Molecules baicalin polyphenol glucuronide cyclodextrin glucanotransferase α-cyclodextrin enzymatic glucosylation |
| title | Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in Water |
| title_full | Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in Water |
| title_fullStr | Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in Water |
| title_full_unstemmed | Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in Water |
| title_short | Enzymatic Synthesis of α-Glucosyl-Baicalin through Transglucosylation via Cyclodextrin Glucanotransferase in Water |
| title_sort | enzymatic synthesis of α glucosyl baicalin through transglucosylation via cyclodextrin glucanotransferase in water |
| topic | baicalin polyphenol glucuronide cyclodextrin glucanotransferase α-cyclodextrin enzymatic glucosylation |
| url | https://www.mdpi.com/1420-3049/28/9/3891 |
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