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Enzymatic Formation of Novel Ginsenoside Rg1-α-Glucosides by Rat Intestinal Homogenates

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Abstract

The variation of linkage positions in ginsenosides leads to diverse pharmacological efficiencies. The hydrolysis and transglycosylation properties of glycosyl hydrolase family enzymes have a great impact on the synthesis of novel and structurally diversified compounds. In this study, six ginsenoside Rg1-α-glucosides were found to be synthesized from the reaction mixture of maltose as a donor and ginsenoside Rg1 as a sugar acceptor in the presence of rat small intestinal homogenates, which exhibit high α-glucosidase activities. The individual compounds were purified and were identified by spectroscopy (HPLC-MS, 1H-NMR, and 13C-NMR) as 6-O-[α-d-glcp-(1→4)-β-d-glcp]-20-O-(β-d-glcp)-20(S)-protopanaxatriol, 6-O-β-d-glcp-20-O-[α-d-glcp-(1→6)-(β-d-glcp)]-20(S)-protopanaxatriol, 6-O-β-d-glcp-20-O-[α-d-glcp-(1→4)-(β-d-glcp)]-20(S)-protopanaxatriol, 6-O-[α-d-glcp-(1→6)-β-d-glcp]-20-O-(β-glcp)-20(S)-protopanaxatriol, 6-O-[α-d-glcp-(1→3)-β-d-glcp]-20-O-(β-d-glcp)-20(S)-protopanaxatriol, and 6-O-β-d-glcp-20-O-[α-d-glcp-(1→3)-(β-d-glcp)]-20(S)-protopanaxatriol. Among these six, 6-O-β-d-glcp-20-O-α-d-glcp-(1→6)-(β-d-glcp)-20(S)-protopanaxatriol and 6-O-α-d-glcp-(1→6)-β-d-glcp-20-O-(β-d-glcp)-20(S)-protopanaxatriol are considered to be novel compounds of alpha-ginsenosidal saponins which pharmacological activities should be further characterized. This is the first report on the enzymatic elaboration of ginsenoside Rg1 derivatives using rat intestinal homogenates. To the best of our knowledge, it is also the first to reveal the sixth and 20th positions of an unusual α-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl sugar chain with 20(S)-protopanaxatriol saponins in Panax ginseng Mayer.

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Acknowledgments

This research was supported by Korea Institute of Planning & Evaluation for Technology in Food, Agriculture, Forestry & Fisheries (KIPET NO: 309019-03-3-SB010) and Next-Generation BioGreen 21 Program (SSAC, grant#: PJ00952903), Republic of Korea.

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Authors and Affiliations

  1. Graduate School of Biotechnology and Ginseng Bank, College of Life Science, Kyung Hee University, Yongin, 446-701, Republic of Korea

    Ramya Mathiyalagan & Deok Chun Yang

  2. Department of Food Science and Biotechnology, Chonbuk National University, Iksan, 570-752, Republic of Korea

    Young-Hoi Kim, Myung-Kon Kim & Min-Ji Kim

  3. Department of Oriental Medicinal Biotechnology, College of Life Science, Kyung Hee University, Yongin, 449-701, Republic of Korea

    Yeon Ju Kim

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  1. Ramya Mathiyalagan
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  2. Young-Hoi Kim
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  5. Min-Ji Kim
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Correspondence to Yeon Ju Kim or Deok Chun Yang.

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Ramya Mathiyalagan and Young-Hoi Kim contributed equally to this work.

Electronic supplementary material

Supplementary Fig. S1

Schematic representation of α-glucosyl-ginsenoside Rg1 synthesis. (JPEG 225 kb)

Supplementary Fig. S2

Effects of pH on the transglycosylation of G-Rg1 with rat small intestinal homogenates. The transglycosylation ratio was expressed as total peak area (%) of new six transglycosylation products by HPLC. (JPEG 116 kb)

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Mathiyalagan, R., Kim, YH., Kim, Y.J. et al. Enzymatic Formation of Novel Ginsenoside Rg1-α-Glucosides by Rat Intestinal Homogenates. Appl Biochem Biotechnol 177, 1701–1715 (2015). https://doi.org/10.1007/s12010-015-1847-0

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  • DOI: https://doi.org/10.1007/s12010-015-1847-0

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