α-Glucosylated 6-gingerol: chemoenzymatic synthesis using α-glucosidase from Halomonas sp. H11, and its physical properties

6-Gingerol [(S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one] is a biologically active compound and is abundant in the rhizomes of ginger (Zingiber officinale). It has some beneficial functions in healthcare, but its use is limited because of its insolubility in water and its heat-instability. To improve these physical properties, the glucosylation of 6-gingerol was investigated using α-glucosidases (EC. 3.2.1.20) from Aspergillus niger, Aspergillus nidulans ABPU1, Acremonium strictum, Halomonas sp. H11, and Saccharomyces cerevisiae, and cyclodextrin glucanotransferases (CGTase, EC. 2.4.1.19) from Bacillus coagulans, Bacillus sp. No. 38-2, Bacillus clarkii 7364, and Geobacillus stearothermophilus. Among these, only α-glucosidase from Halomonas sp. H11 (HaG) transferred a glucosyl moiety to 6-gingerol, and produced glucosylated compounds. The chemical structure of the reaction product, determined by nuclear magnetic resonance spectroscopy and mass spectrometry, was (S)-5-(O-α-d-glucopyranosyl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one (5-α-Glc-gingerol). Notably, the regioisomer formed by glucosylation of the phenolic OH was not observed at all, indicating that HaG specifically transferred the glucose moiety to the 5-OH of the β-hydroxy keto group in 6-gingerol. Almost 60% of the original 6-gingerol was converted into 5-α-Glc-gingerol by the reaction. In contrast to 6-gingerol, 5-α-Glc-gingerol, in the form of an orange powder prepared by freeze-drying, was water-soluble and stable at room temperature. It was also more stable than 6-gingerol under acidic conditions and to heat.

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► Chemoenzymatic synthesis of α-glucosylated 6-gingerol.
► α-Glucosidases and cyclodextrin glucanotransferases from various microorganisms were evaluated.
► α-Glucosidase from Halomonas sp. H11 site specifically glucosylated 6-gingerol.
► Glucosylated 6-gingerol was water-soluble and more stable than 6-gingerol.