Transglycosylation to Ginseng Saponins by Cyclomaltodextrin Glucanotransferases

Kim, Young-Hoi; Lee, Young-Gu; Choi, Kang-Ju; Uchida, Kei; Suzuki, Yukio

doi:10.1271/bbb.65.875

Cited by 18 publications

(22 citation statements)

References 3 publications

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“…However, only a few reports have examined the unusual form of α-D-glucopyranosyl sugar linked with β sugar in ginsenosides [6,27]. The present study will provide additional support for the use of α-D-glucopyranosyl sugar in P. ginseng saponins.…”

Section: Discussionsupporting

confidence: 52%

“…Transglycosylation of Rg1 by cyclomaltodextrin glucanotransferases was specific at the C3'-and C4'-hydroxyl groups of the glucose moiety linked at the C6-hydroxyl group of aglycone [6], whereas rat intestinal homogenates produced glycosylation activity of the glucose moiety linked at the C20-hydroxyl group of aglycone in our study. In addition, α-D-glcp-(1→3)-β-D-glcp and α-D-glcp-(1→4)-β-D-glcp sugar chains on the C20-hydroxyl group in Rg1 were reported [27], whereas ours is the first report of the unusual α-D-glcp-(1→6)-β-D-glcp sugar chain.…”

Section: Discussioncontrasting

confidence: 43%

“…Glycosylation offers considerably enhanced solubility, increases sweetness [18], and decreases the bitterness of ginsenosides [6]. Similarly, our newly synthesized compounds are also expected to increase solubility and decrease bitterness compared with that of the source Rg1.…”

Section: Discussionmentioning

confidence: 82%

“…No other significant shifts were observed in the carbon signals of the β-glucose moiety linked at the C20-hydroxyl group of aglycone. It is known that acetic acid treatment (50 % aqueous) of ginsenosides leads to rapid hydrolysis and is accompanied by the consequent epimerization of the C20-hydroxyl group in the 20-O-glycosyl moiety of the aglycone, producing 20 (R & S)-prosapogenin and Δ 20 -prosapogenin [6]. The 50 % acetic acid hydrolysis leads to products with lower Rf values than those from ginsenoside Rg1 (Fig.…”

Section: Isolation and Identification Of Transglycosylated Compoundsmentioning

confidence: 99%

“…The formation of linkage bonds by enzymatic transglycosylation (transfer of a glucose molecule from a donor to the acceptor molecule) of active substances to enhance their physiological functions and properties on phenolic compounds [22], vitamins [10], sugars, and natural glycosides has gained special attention. Various reports have been published on the glycosylation of steroidal saponins and ginseng saponins by cyclodextrin glycosyltransferase (CGTase) [6], toruzyme [26], and glycosidase [4,7].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

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

Mathiyalagan

Kim

et al. 2015

Appl Biochem Biotechnol

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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, (1)H-NMR, and (13)C-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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Section: Discussionsupporting

confidence: 52%

Section: Discussioncontrasting

confidence: 43%

Section: Discussionmentioning

confidence: 82%

Section: Isolation and Identification Of Transglycosylated Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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

Mathiyalagan

Kim

et al. 2015

Appl Biochem Biotechnol

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Beta-Cyclomaltodextrin Glucanotransferase of a Species of Alkaliphilic Bacillus for the Production of Beta-Cyclodextrin

Nakamura

2011

Extremophiles Handbook

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Engineering of cyclodextrin glucanotransferases and the impact for biotechnological applications

Leemhuis

Kelly

Dijkhuizen

2009

Appl Microbiol Biotechnol

164

112

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Cyclodextrin glucanotransferases (CGTases) are industrially important enzymes that produce cyclic α-(1,4)-linked oligosaccharides (cyclodextrins) from starch. Cyclodextrin glucanotransferases are also applied as catalysts in the synthesis of glycosylated molecules and can act as antistaling agents in the baking industry. To improve the performance of CGTases in these various applications, protein engineers are screening for CGTase variants with higher product yields, improved CD size specificity, etc. In this review, we focus on the strategies employed in obtaining CGTases with new or enhanced enzymatic capabilities by searching for new enzymes and improving existing enzymatic activities via protein engineering.

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Transglycosylation to Ginseng Saponins by Cyclomaltodextrin Glucanotransferases

Cited by 18 publications

References 3 publications

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

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

Beta-Cyclomaltodextrin Glucanotransferase of a Species of Alkaliphilic Bacillus for the Production of Beta-Cyclodextrin

Engineering of cyclodextrin glucanotransferases and the impact for biotechnological applications

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