Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: root
NCBI PubMed ID: 22805203Publication DOI: 10.1111/j.1365-2672.2012.05400.xJournal NLM ID: 9706280Publisher: Oxford: Blackwell Publishing for the Society for Applied Bacteriology
Correspondence: sungchangkeun
126.com
Institutions: Department of Food Science and Technology, College of Agriculture and Biotechnology, Chungnam National University, Taejeon, South Korea, Key Laboratory of Systematic Mycology and Lichenology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, College of Chinese Medicinal Material, Jilin Agricultural University, Jilin, China
This study examined the biotransformation pathway of ginsenoside Rb1 by the fungus Esteya vermicola CNU 120806. Ginsenosides Rb1 and Rd were extracted from the root of Panax ginseng. Liquid fermentation and purified enzyme hydrolysis were employed to investigate the biotransformation of ginsenoside Rb1. The metabolites were identified and confirmed using NMR analysis as gypenoside XVII and gypenoside LXXV. A mole yield of 95.4% gypenoside LXXV was obtained by enzymatic conversion (pH 5.0, temperature 50°C). Ginsenoside Rd was used to verify the transformation pathway under the same reaction condition. The product Compound K (mole yield 49.6%) proved a consecutive hydrolyses occurred at the C-3 position of ginsenoside Rb1. Conclusions: Strain CNU 120806 showed a high degree of specific β-glucosidase activity to convert ginsenosides Rb1 and Rd to gypenoside LXXV and Compound K, respectively. The maximal activity of the purified glucosidase for ginsenosides transformation occurred at 50°C and pH 5.0. Compared with its activity against pNPG (100%), the β-glucosidase exhibited quite lower level of activity against other aryl-glycosides. Enzymatic hydrolysate, gypenoside LXXV and Compound K were produced by consecutive hydrolyses of the terminal and inner glucopyranosyl moieties at the C-3 carbon of ginsenoside Rb1 and Rd, giving the pathway: ginsenoside Rb1 → gypenoside XVII → gypenoside LXXV; ginsenoside Rd → F2 → Compound K, but did not hydrolyse the 20-C, β-(1-6)-glucoside of ginsenoside Rb1 and Rd. Significance and Impact of the Study: The results showed an important practical application on the preparation of gypenoside LXXV. Additionally, this study for the first time provided a high efficient preparation method for gypenoside LXXV without further conversion, which also gives rise to a potential commercial enzyme application.
β-glucosidase, compound K, Esteya vermicola CNU120806, ginsenoside Rb 1, gypenoside LXXV, gypenoside XVII
Structure type: monomer
Location inside paper: Fig.1, Rh2
Trivial name: ginsenoside Rh2, (20S)-ginsenoside Rh2, ginsenoside
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, gel filtration, SDS-PAGE, ESI-MS, HPLC, extraction, CC, cell growth, enzymatic assay, precipitation
Related record ID(s): 44242, 44243, 44244, 44245, 44246, 44247, 44248, 44250, 44251, 44501, 47981
NCBI Taxonomy refs (TaxIDs): 4054
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There is only one chemically distinct structure:
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