- Dammarane-type triterpene saponins from Panax japonicus
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Six new dammarane-type saponins (1-6), together with 11 known saponins (7-17), were isolated from Ye-Sanchi, the underground part of Panax japonicus collected in the South of Yunnan Province, China. Their structures were elucidated by chemical and spectroscopic means.
- Zou, Kun,Zhu, Shu,Tohda, Chihiro,Cai, Shaoqing,Komatsu, Katsuko
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- Glycoside Hydrolase Family 39 β-Xylosidases Exhibit β-1,2-Xylosidase Activity for Transformation of Notoginsenosides: A New EC Subsubclass
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β-1,2-Xylosidase activity has not been recorded as an EC subsubclass. In this study, phylogenetic analysis and multiple sequence alignments revealed that characterized β-xylosidases of glycoside hydrolase family (GH) 39 were classified into the same subgroup with conserved amino acid residue positions participating in substrate recognition. Protein-ligand docking revealed that seven of these positions were probably essential to bind xylose-glucose, which is linked by a β-1,2-glycosidic bond. Amino acid residues in five of the seven positions are invariant, while those in two of the seven positions are variable with low frequency. Both the wild-type β-xylosidase rJB13GH39 and its mutants with mutation at the two positions exhibited β-1,2-xylosidase activity, as they hydrolyzed o-nitrophenyl-β-d-xylopyranoside and transformed notoginsenosides R1 and R2 to ginsenosides Rg1 and Rh1, respectively. The results suggest that all of these characterized GH 39 β-xylosidases probably show β-1,2-xylosidase activity, which should be assigned an EC number with these β-xylosidases as representatives.
- Zhang, Rui,Li, Na,Xu, Shujing,Han, Xiaowei,Li, Chunyan,Wei, Xin,Liu, Yu,Tu, Tao,Tang, Xianghua,Zhou, Junpei,Huang, Zunxi
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- Characterization of metabolism and in vitro permeability study of notoginsenoside R1 from radix notoginseng
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As a main and characteristic constituent in Radix notoginseng, the fate of notoginsenoside R1 (NGR1) in human is largely unknown. The present study investigated, for the first time, NGR1 metabolism by human intestinal bacteria and liver subcellular fractions, and permeability properties of NGR1 and resultant metabolites on a Caco-2 model. Samples were qualitatively analyzed using HPLC-MS/MS and quantitatively determined using HPLC-UV. When incubated with pooled human intestinal bacteria anaerobically, NGR1 showed biphasic elimination: an insignificant decrease in the first 8 h followed by a rapid elimination during 8-48 h. Four metabolites, three unambiguously identified as ginsenosides Rg1, F1 and 20(S)-protopanaxatriol formed via stepwise deglycosylation, and one tentatively assigned as a dehydrogenated protopanaxatriol with transformation occurring at the tetracyclic triterpenoid skeleton, were produced sequentially. Rg1 and F1 were formed transiently at low apparent velocities, while 20(S)-protopanaxatriol was the major metabolite with a formation rate close to the rate of NGR1 elimination and a low elimination rate. NGR1 remained intact in human liver S9 or microsomes over 1 h. Transport study of NGR1 and its metabolites revealed an ascending permeability order with stepwise deglycosylation. Taken together, the results revealed a determinant role of intestinal bacteria in the overall disposition and potential bioactivity of NGR1 in human.
- Ruan, Jian-Qing,Leong, Weng-Im,Yan, Ru,Wang, Yi-Tao
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- Enzymatic preparation of ginsenosides Rg2, Rh1, and F1 from protopanaxatriol-type ginseng saponin mixture
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During investigations on the hydrolysis of a protopanaxatriol-type saponin mixture by various glycoside hydrolases, it was found that two minor saponins, ginsenosides Rg2 and Rh1, were formed in high yields by crude β-galactosidase from Aspergillus oryzae and crude lactase from Penicillium sp., respectively. Moreover, a crude preparation of naringinase from Penicillium decumbens readily hydrolyzed a protopanaxatriol-type saponin mixture to give an intestinal bacterial metabolite, ginsenoside F1 as the main product. A crude preparation of hesperidinase from Penicillium sp. selectively hydrolyzed ginsenoside Re into ginsenoside Rg1. This is the first report on the enzymatic preparation of minor saponins, ginsenosides Rg2 and Rh1, and of an intestinal bacterial metabolite, ginsenoside F1, with a high efficiency from a protopanaxatriol-type saponin mixture.
- Ko, Sung-Ryong,Choi, Kang-Ju,Uchida, Kei,Suzuki, Yukio
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- Glycoside Hydrolase Family 39 β-Xylosidases Exhibit β-1,2-Xylosidase Activity for Transformation of Notoginsenosides: A New EC Subsubclass
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β-1,2-Xylosidase activity has not been recorded as an EC subsubclass. In this study, phylogenetic analysis and multiple sequence alignments revealed that characterized β-xylosidases of glycoside hydrolase family (GH) 39 were classified into the same subgroup with conserved amino acid residue positions participating in substrate recognition. Protein-ligand docking revealed that seven of these positions were probably essential to bind xylose-glucose, which is linked by a β-1,2-glycosidic bond. Amino acid residues in five of the seven positions are invariant, while those in two of the seven positions are variable with low frequency. Both the wild-type β-xylosidase rJB13GH39 and its mutants with mutation at the two positions exhibited β-1,2-xylosidase activity, as they hydrolyzed o-nitrophenyl-β-d-xylopyranoside and transformed notoginsenosides R1 and R2 to ginsenosides Rg1 and Rh1, respectively. The results suggest that all of these characterized GH 39 β-xylosidases probably show β-1,2-xylosidase activity, which should be assigned an EC number with these β-xylosidases as representatives.
- Zhang, Rui,Li, Na,Xu, Shujing,Han, Xiaowei,Li, Chunyan,Wei, Xin,Liu, Yu,Tu, Tao,Tang, Xianghua,Zhou, Junpei,Huang, Zunxi
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p. 3220 - 3228
(2019/03/26)
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- Synthetic access toward the diverse ginsenosides
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All the possible types of the protopanaxatriol and protopanaxadiol glycosides, the major active yet extremely heterogeneous principles of ginsengs, could be accessed by the present sequence of transformations, including global removal of the sugar residue
- Yu, Jun,Sun, Jiansong,Niu, Yiming,Li, Rongyao,Liao, Jinxi,Zhang, Fuyi,Yu, Biao
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p. 3899 - 3905
(2013/09/23)
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- METHOD FOR PREPARING NOVEL PROCESSED GINSENG OR AN EXTRACT THEREOF, THE USUALLY MINUTE GINSENOSIDE CONTENT OF WHICH IS INCREASED
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The present invention relates to a method for preparing a processed ginseng or processed ginseng extract. Specifically, the invention relates to a method for preparing a processed ginseng or processed ginseng extract having increased ginsenoside contents. More specifically, the invention relates to a method of preparing a novel processed ginseng or processed ginseng extract having increased ginsenoside contents by preparing saponinase, fermenting ginseng or red ginseng with the prepared saponinase and hydrolyzing the fermented ginseng or red ginseng with an organic acid and to an anticancer supplement composition or pharmaceutical composition comprising the processed ginseng or processed ginseng extract prepared thereby.
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Paragraph 0049; 0050; 0051
(2013/03/28)
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