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

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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

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