Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from Parageobacillus galactosidasius DSM 18751

Mangiferin is a natural antioxidant C-glucosidic xanthone originally isolated from the Mangifera indica (mango) plant. Mangiferin exhibits a wide range of pharmaceutical activities. However, mangiferin’s poor solubility limits its applications. To resolve this l...

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Autores principales:	Jiumn-Yih Wu, Hsiou-Yu Ding, Tzi-Yuan Wang, Yu-Li Tsai, Huei-Ju Ting, Te-Sheng Chang
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	mangiferin maltogenic amylase glycosylation glucoside <i>Parageobacillus galactosidasius</i> Therapeutics. Pharmacology RM1-950
Acceso en línea:	https://doaj.org/article/96971701406a42b68a5b0ee593b3fa5d
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spelling	oai:doaj.org-article:96971701406a42b68a5b0ee593b3fa5d2021-11-25T16:29:00ZImproving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 1875110.3390/antiox101118172076-3921https://doaj.org/article/96971701406a42b68a5b0ee593b3fa5d2021-11-01T00:00:00Zhttps://www.mdpi.com/2076-3921/10/11/1817https://doaj.org/toc/2076-3921Mangiferin is a natural antioxidant <i>C</i>-glucosidic xanthone originally isolated from the <i>Mangifera indica</i> (mango) plant. Mangiferin exhibits a wide range of pharmaceutical activities. However, mangiferin’s poor solubility limits its applications. To resolve this limitation of mangiferin, enzymatic glycosylation of mangiferin to produce more soluble mangiferin glucosides was evaluated. Herein, the recombinant maltogenic amylase (MA; E.C. 3.2.1.133) from a thermophile <i>Parageobacillus galactosidasius</i> DSM 18751<sup>T</sup> (<i>Pg</i>MA) was cloned into <i>Escherichia coli</i> BL21 (DE3) via the expression plasmid pET-Duet-1. The recombinant <i>Pg</i>MA was purified via Ni<sup>2+</sup> affinity chromatography. To evaluate its transglycosylation activity, 17 molecules, including mangiferin (as sugar acceptors), belonging to triterpenoids, saponins, flavonoids, and polyphenol glycosides, were assayed with β-CD (as the sugar donor). The results showed that puerarin and mangiferin are suitable sugar acceptors in the transglycosylation reaction. The glycosylation products from mangiferin by <i>Pg</i>MA were isolated using preparative high-performance liquid chromatography. Their chemical structures were glucosyl-<i>α</i>-(1→6)-mangiferin and maltosyl-<i>α</i>-(1→6)-mangiferin, determined by mass and nucleic magnetic resonance spectral analysis. The newly identified maltosyl-<i>α</i>-(1→6)-mangiferin showed 5500-fold higher aqueous solubility than that of mangiferin, and both mangiferin glucosides exhibited similar 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activities compared to mangiferin. <i>Pg</i>MA is the first MA with glycosylation activity toward mangiferin, meaning mangiferin glucosides have potential future applications.Jiumn-Yih WuHsiou-Yu DingTzi-Yuan WangYu-Li TsaiHuei-Ju TingTe-Sheng ChangMDPI AGarticlemangiferinmaltogenic amylaseglycosylationglucoside<i>Parageobacillus galactosidasius</i>Therapeutics. PharmacologyRM1-950ENAntioxidants, Vol 10, Iss 1817, p 1817 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	mangiferin maltogenic amylase glycosylation glucoside <i>Parageobacillus galactosidasius</i> Therapeutics. Pharmacology RM1-950
spellingShingle	mangiferin maltogenic amylase glycosylation glucoside <i>Parageobacillus galactosidasius</i> Therapeutics. Pharmacology RM1-950 Jiumn-Yih Wu Hsiou-Yu Ding Tzi-Yuan Wang Yu-Li Tsai Huei-Ju Ting Te-Sheng Chang Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 18751
description	Mangiferin is a natural antioxidant <i>C</i>-glucosidic xanthone originally isolated from the <i>Mangifera indica</i> (mango) plant. Mangiferin exhibits a wide range of pharmaceutical activities. However, mangiferin’s poor solubility limits its applications. To resolve this limitation of mangiferin, enzymatic glycosylation of mangiferin to produce more soluble mangiferin glucosides was evaluated. Herein, the recombinant maltogenic amylase (MA; E.C. 3.2.1.133) from a thermophile <i>Parageobacillus galactosidasius</i> DSM 18751<sup>T</sup> (<i>Pg</i>MA) was cloned into <i>Escherichia coli</i> BL21 (DE3) via the expression plasmid pET-Duet-1. The recombinant <i>Pg</i>MA was purified via Ni<sup>2+</sup> affinity chromatography. To evaluate its transglycosylation activity, 17 molecules, including mangiferin (as sugar acceptors), belonging to triterpenoids, saponins, flavonoids, and polyphenol glycosides, were assayed with β-CD (as the sugar donor). The results showed that puerarin and mangiferin are suitable sugar acceptors in the transglycosylation reaction. The glycosylation products from mangiferin by <i>Pg</i>MA were isolated using preparative high-performance liquid chromatography. Their chemical structures were glucosyl-<i>α</i>-(1→6)-mangiferin and maltosyl-<i>α</i>-(1→6)-mangiferin, determined by mass and nucleic magnetic resonance spectral analysis. The newly identified maltosyl-<i>α</i>-(1→6)-mangiferin showed 5500-fold higher aqueous solubility than that of mangiferin, and both mangiferin glucosides exhibited similar 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activities compared to mangiferin. <i>Pg</i>MA is the first MA with glycosylation activity toward mangiferin, meaning mangiferin glucosides have potential future applications.
format	article
author	Jiumn-Yih Wu Hsiou-Yu Ding Tzi-Yuan Wang Yu-Li Tsai Huei-Ju Ting Te-Sheng Chang
author_facet	Jiumn-Yih Wu Hsiou-Yu Ding Tzi-Yuan Wang Yu-Li Tsai Huei-Ju Ting Te-Sheng Chang
author_sort	Jiumn-Yih Wu
title	Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 18751
title_short	Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 18751
title_full	Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 18751
title_fullStr	Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 18751
title_full_unstemmed	Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 18751
title_sort	improving aqueous solubility of natural antioxidant mangiferin through glycosylation by maltogenic amylase from <i>parageobacillus galactosidasius</i> dsm 18751
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/96971701406a42b68a5b0ee593b3fa5d
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Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from <i>Parageobacillus galactosidasius</i> DSM 18751

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