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. 2020 Mar 31;10(4):525.
doi: 10.3390/biom10040525.

Characterization of a Novel Ginsenoside MT1 Produced by an Enzymatic Transrhamnosylation of Protopanaxatriol-Type Ginsenosides Re

Byeong-Min Jeon  1 , Jong-In Baek  1 , Min-Sung Kim  1 , Sun-Chang Kim  1   2   3 , Chang-Hao Cui  2
Affiliations

Characterization of a Novel Ginsenoside MT1 Produced by an Enzymatic Transrhamnosylation of Protopanaxatriol-Type Ginsenosides Re

Byeong-Min Jeon et al. Biomolecules. .

Abstract

Background: Ginsenosides, triterpene saponins of Panax species, are considered the main active ingredients responsible for various pharmacological activities. Herein, a new protopanaxatriol-type ginsenoside called "ginsenoside MT1" is described; it was accidentally found among the enzymatic conversion products of ginsenoside Re.

Method: We analyzed the conversion mechanism and found that recombinant β-glucosidase (MT619) transglycosylated the outer rhamnopyranoside of Re at the C-6 position to glucopyranoside at C-20. The production of MT1 by trans-rhamnosylation was optimized and pure MT1 was obtained through various chromatographic processes.

Results: The structure of MT1 was elucidated based on spectral data: (20S)-3β,6α,12β,20-tetrahydroxydammarene-20-O-[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranoside]. This dammarane-type triterpene saponin was confirmed as a novel compound.

Conclusion: Based on the functions of ginsenosides with similar structures, we believe that this ginsenoside MT1 may have great potential in the development of nutraceutical, pharmaceutical or cosmeceutical products.

Keywords: biotechnology; biotransformation; dammarane-type triterpene saponin; ginsenoside MT1; ginsenosides; transglycosylation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Thin layer chromatography of hydrolyzation products by MT619. C1, Re; 1, Re transformation products; 2, Re transformation products with F1 added; 3, Re transformation products with PPT added; C2, Rg2(S); 4, Rg2(S) transformation products; 5, Rg2(S) transformation products with F1 added; 6, Rg2(S) transformation products with PPT added.
Figure 2
Figure 2
Effects of the substrate Re concentrations (A) and remaining Re concentrations (B) in the reaction mixture.
Figure 3
Figure 3
The relative abundance of ginsenosides Re, MT1, F1 and PPT in a scaled-up production reactor over time.
Figure 4
Figure 4
HPLC analysis of purified MT1 from the product mixture. (STD1), ginsenoside Rg2(S) standard; (STD2), standards of ginsenosides Rg1, Re, F1 and PPT; (A), substrate ginsenoside Re before purification; (B), biotransformed products from the MT619 conversion mixture; (C), MT1 isolated using Recycling preparative high-performance liquid chromatography (RPHPLC).
Figure 5
Figure 5
The structure ginsenoside MT1 based on the spectral data.
Figure 6
Figure 6
Conversion pathways of ginsenosides Re and Rg2(S) by MT619.
See this image and copyright information in PMC

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