Abstract
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 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 Parageobacillus galactosidasius DSM 18751T (PgMA) was cloned into Escherichia coli BL21 (DE3) via the expression plasmid pET-Duet-1. The recombinant PgMA was purified via Ni2+ 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 PgMA were isolated using preparative high-performance liquid chromatography. Their chemical structures were glucosyl-α-(1→6)-mangiferin and maltosyl-α-(1→6)-mangiferin, determined by mass and nucleic magnetic resonance spectral analysis. The newly identified maltosyl-α-(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. PgMA is the first MA with glycosylation activity toward mangiferin, meaning mangiferin glucosides have potential future applications.
Highlights
Mangiferin is a natural C-glucosidic xanthone originally isolated from the Mangifera indica plant
The results showed that only puerarin (Figure 5a) and mangiferin
The results showed that only puerarin (Figure 5a) and mangiferin (Figure 5b) could be glycosylated by PgMA
Summary
Mangiferin is a natural C-glucosidic xanthone originally isolated from the Mangifera indica (mango) plant. Mangiferin has been reported to possess diverse health-promoting activities, such as antioxidant [1,2], anticancer [3,4], anti-inflammatory [5], and anti-osteoarthritis pain activities [6], allowing it to prevent memory impairment [7], neurodegeneration [8], and organ fibrosis [9]. It offers protection from the deleterious effects of heavy metals [10]. As the glycosylates of small molecules have been proven to have better aqueous solubility and bioavailability than the original molecules [13,14], the glycosylation of mangiferin should be further improved for better usage. 4.0/).
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