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

Jeon, Byeong-Min; Baek, Jong-In; Kim, Min-Sung; Kim, Sun-Chang; Cui, Chang-hao

doi:10.3390/biom10040525

Open AccessArticle

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

by

Byeong-Min Jeon

^1,†

,

Jong-In Baek

^1,†

,

Min-Sung Kim

¹,

Sun-Chang Kim

^1,2,3,* and

Chang-hao Cui

^2,*

¹

Department of Biological Sciences, Korea Advanced Institute of Science and Technology, 291 Daehak-Ro, Yuseong-Gu, Daejeon 305-701, Korea

²

Intelligent Synthetic Biology Center, 291 Daehak-Ro, Yuseong-Gu, Daejeon 305-701, Korea

³

KAIST Institute for Biocentury, Korea Advanced Institute of Science and Technology, 291 Daehak-Ro, Yuseong-Gu, Daejeon 305-701, Korea

^*

Authors to whom correspondence should be addressed.

^†

These authors contributed equally to this work.

Biomolecules 2020, 10(4), 525; https://doi.org/10.3390/biom10040525

Submission received: 26 February 2020 / Revised: 25 March 2020 / Accepted: 26 March 2020 / Published: 31 March 2020

(This article belongs to the Special Issue Advances in Ginsenosides)

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

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MDPI and ACS Style

Jeon, B.-M.; Baek, J.-I.; Kim, M.-S.; Kim, S.-C.; Cui, C.-h. Characterization of a Novel Ginsenoside MT1 Produced by an Enzymatic Transrhamnosylation of Protopanaxatriol-Type Ginsenosides Re. Biomolecules 2020, 10, 525. https://doi.org/10.3390/biom10040525

AMA Style

Jeon B-M, Baek J-I, Kim M-S, Kim S-C, Cui C-h. Characterization of a Novel Ginsenoside MT1 Produced by an Enzymatic Transrhamnosylation of Protopanaxatriol-Type Ginsenosides Re. Biomolecules. 2020; 10(4):525. https://doi.org/10.3390/biom10040525

Chicago/Turabian Style

Jeon, Byeong-Min, Jong-In Baek, Min-Sung Kim, Sun-Chang Kim, and Chang-hao Cui. 2020. "Characterization of a Novel Ginsenoside MT1 Produced by an Enzymatic Transrhamnosylation of Protopanaxatriol-Type Ginsenosides Re" Biomolecules 10, no. 4: 525. https://doi.org/10.3390/biom10040525

APA Style

Jeon, B.-M., Baek, J.-I., Kim, M.-S., Kim, S.-C., & Cui, C.-h. (2020). Characterization of a Novel Ginsenoside MT1 Produced by an Enzymatic Transrhamnosylation of Protopanaxatriol-Type Ginsenosides Re. Biomolecules, 10(4), 525. https://doi.org/10.3390/biom10040525

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

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