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

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

doi:10.3390/biom10040525

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.

Highlights

Ginsenosides—triterpene saponins composed of a dammarane skeleton with several glycosylation positions—are generally considered the main active components of ginseng, that has been used as a traditional herbal medicine in East Asian countries for thousands of years to stimulate physical and mental activity [1,2]
Six major kinds of ginsenoside (Rb1, Rb2, Rc, Re, Rd and Rg1), as shown in Figure S1, constitute >90% of the total ginsenosides in ginseng [2,8]. They are relatively abundant in ginseng and can be converted into minor ginsenosides, which naturally exist in smaller amounts and have higher chemical reactivities [9,10,11]
Ginsenoside Re Transformation of MT619 MT619 was purified by Ni column and DEAE column chromatography as described in a prevMioTu6s1s9tuwdays[p1u5]r.ifiTeodabnyalNyzi ecothluemtrnanansfdorDmEaAtiEoncopluamthnwcahyrso,mgiantsoegnroapsihdyesasRdeeasncrdibRegd2 iwn earperreevaicotueds satsudsuyb[s1t5r]a.tTeso wanitahlypzuertihfeietdraMnsTfo6r1m9 gatiinosnenpoasthidweaaynsd, gFin1 saenndosthideecsoRnevaenrsdioRng2prwoedruecrtesawcteedreassusbujbescttreadtetso wTiLthC paunraifilyesdisM

Summary

Introduction

Ginsenosides—triterpene saponins composed of a dammarane skeleton with several glycosylation positions—are generally considered the main active components of ginseng, that has been used as a traditional herbal medicine in East Asian countries for thousands of years to stimulate physical and mental activity [1,2]. Six major kinds of ginsenoside (Rb1, Rb2, Rc, Re, Rd and Rg1), as shown, constitute >90% of the total ginsenosides in ginseng [2,8]. They are relatively abundant in ginseng and can be converted into minor ginsenosides, which naturally exist in smaller amounts and have higher chemical reactivities [9,10,11]. Many enzymes have been explored to efficiently convert major ginsenosides into pharmacologically active, rare minor ginsenosides [5,13,14]. 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

Methods

Results

Discussion

Conclusion