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Microbial transformation of ginsenoside Rb1 to compound K by Lactobacillus paralimentarius.
Quan, Lin-Hu,Kim, Yeon-Ju,Li, Guan Hao,Choi, Kwang-Tea,Yang, Deok-Chun Springer 2013 World journal of microbiology biotechnology Vol.29 No.6
<P>In this study, the major ginsenoside Rb1 was transformed into the more pharmacologically active minor compound K by food grade Lactobacillus paralimentarius LH4, which was isolated from kimchi, a traditional Korean fermented food. The enzymatic reaction was analyzed by TLC, HPLC, and NMR. Using the cell-free enzyme of Lactobacillus paralimentarius LH4 at optimal conditions for 30?C at pH 6.0, 1.0?mg?ml(-1) ginsenoside Rb1 was transformed into 0.52?mg?ml(-1) compound K within 72?h, with a corresponding molar conversion yield of 88?%. The cell-free enzyme hydrolyzed the two glucose moieties attached to the C-3 position and the outer glucose moiety attached to the C-20 position of the ginsenoside Rb1. The cell-free enzyme hydrolyzed the ginsenoside Rb1 along the following pathway: ginsenoside Rb1??gypenoside XVII and ginsenoside Rd??ginsenoside F2??compound K. Our results indicate that Lactobacillus paralimentarius LH4 has the potential to be applied for the preparation of compound K in the food industry.</P>
Quan, Lin-Hu,Min, Jin-Woo,Yang, Dong-Uk,Kim, Yeon-Ju,Yang, Deok-Chun Springer International 2012 Applied microbiology and biotechnology Vol.94 No.2
<P>Microbacterium esteraromaticum was isolated from ginseng field. The beta-glucosidase gene (bgp1) from M. esteraromaticum was cloned and expressed in Escherichia coli BL21 (DE3). The bgp1 gene consists of 2,496 bp encoding 831 amino acids which have homology to the glycosyl hydrolase family 3 protein domain. The recombinant beta-glucosidase enzyme (Bgp1) was purified and characterized. The molecular mass of purified Bgp1 was 87.5 kDa, as determined by SDS-PAGE. Using 0.1 mg ml(-1) enzyme in 20 mM sodium phosphate buffer at 37A degrees C and pH 7.0, 1.0 mg ml(-1) ginsenoside Rb1 was transformed into 0.444 mg ml(-1) ginsenoside Rg3 within 6 h. The Bgp1 sequentially hydrolyzed the outer and inner glucose attached to the C-20 position of ginsenosides Rb1. Bgp1 hydrolyzed the ginsenoside Rb1 along the following pathway: Rb1 -> aEuro parts per thousand Rd -> aEuro parts per thousand 20(S)-Rg3. This is the first report of the biotransformation of ginsenoside Rb1 to ginsenoside 20(S)-Rg3 using the recombinant beta-glucosidase.</P>
Lin-Hu Quan,Jin-Ying Piao,Jin-Woo Min,Ho-Bin Kim,Sang-Rae Kim,Dong-Uk Yang,Deok Chun Yang 고려인삼학회 2011 Journal of Ginseng Research Vol.35 No.3
Ginsenoside Rb<sub>1</sub>is the main component in ginsenosides. It is a protopanaxadiol-type ginsenoside that has a dammarane-type triterpenoid as an aglycone. In this study, ginsenoside Rb<sub>1</sub> was transformed into gypenoside XVII, ginsenoside Rd, ginsenoside F<sub>2</sub> and compound K by glycosidase from Leuconostoc mesenteroides DC102. The optimum time for the conversion was about 72 h at a constant pH of 6.0 to 8.0 and the optimum temperature was about 30℃. Under optimal conditions, ginsenoside Rb<sub>1</sub> was decomposed and converted into compound K by 72 h post-reaction (99%). The enzymatic reaction was analyzed by high-performance liquid chromatography, suggesting the transformation pathway: ginsenoside Rb<sub>1</sub>→gypenoside XVII and ginsenoside Rd→ginsenoside F<sub>2</sub>→compound K.
Lin-Hu Quan,Jin-Ying Piao,Jin-Woo Min,Ho-Bin Kim,Sang-Rae Kim,Dong-Uk Yang,Deok Chun Yang 고려인삼학회 2011 Journal of Ginseng Research Vol.35 No.3
Ginsenoside Rb_1is the main component in ginsenosides. It is a protopanaxadiol-type ginsenoside that has a dammarane-type triterpenoid as an aglycone. In this study, ginsenoside Rb_1 was transformed into gypenoside XVII, ginsenoside Rd, ginsenoside F_2 and compound K by glycosidase from Leuconostoc mesenteroides DC102. The optimum time for the conversion was about 72 h at a constant pH of 6.0 to 8.0 and the optimum temperature was about 30°C. Under optimal conditions, ginsenoside Rb_1was decomposed and converted into compound K by 72 h post-reaction (99%). The enzymatic reaction was analyzed by highperformance liquid chromatography, suggesting the transformation pathway: ginsenoside Rb_1→ gypenoside XVII and ginsenoside Rd→ginsenoside F_2→compound K.
Quan, Lin-Hu,Piao, Jin-Ying,Min, Jin-Woo,Yang, Dong-Uk,Lee, Hee Nyeong,Yang, Deok Chun Sociedade Brasileira de Microbiologia 2011 Brazilian journal of microbiology Vol.42 No.3
<P>About 40 different types of ginsenoside (ginseng saponin), a major pharmacological component of ginseng, have been identified along with their physiological activities. Among these, compound K has been reported to prevent the development of and the metastasis of cancer by blocking the formation of tumors and suppressing the invasion of cancerous cells. In this study, ginsenoside Rb1 was converted into compound K via interaction with the enzyme secreted by β-glucosidase active bacteria, <I>Leuconostoc citreum</I> LH1, extracted from kimchi. The optimum time for the conversion of Rb1 to compound K was about 72 hrs at a constant pH of 6.0 and an optimum temperature of about 30°C. Under optimal conditions, ginsenoside Rb1 was decomposed and converted into compound K by 72 hrs post-reaction (99%). Both TLC and HPLC were used to analyze the enzymatic reaction. Ginsenoside Rb1 was consecutively converted to ginsenoside Rd, F2, and compound K via the hydrolyses of 20-C β-(1 → 6)-glucoside, 3-C β-(1 → 2)-glucoside, and 3-C β-glucose of ginsenoside Rb1.</P>
Bioconversion of Ginsenoside Rd into Compound K by Lactobacillus pentosus DC101 Isolated from Kimchi
Lin-Hu Quan,Le-Qin Cheng,Ho-Bin Kim,Ju-Han Kim,Na-Ri Son,Se-Young Kim,Hyun-O Jin,Deok-Chun Yang 고려인삼학회 2010 Journal of Ginseng Research Vol.34 No.4
Ginsenosides are the principal components responsible for the pharmacological and biological activities of ginseng. Ginsenoside Rd was transformed into compound K using cell-free extracts of food microorganisms, with Lactobacillus pentosus DC101 isolated from kimchi (traditional Korean fermented food) used for this conversion. The optimum time for the conversion was about 72 h at a constant pH of 7.0 and an optimum temperature of about 30°C. The transformation products were identified by thin-layer chromatography and high-performance liquid chromatography, and their structures were assigned using nuclear magnetic resonance analysis. Generally, ginsenoside Rd was converted into ginsenoside F2 by 36 h post-reaction. Consequently, over 97% of ginsenoside Rd was decomposed and converted into compound K by 72 h post-reaction. The bioconversion pathway to produce compound K is as follows: ginsenoside Rd→ginsenoside F2→compound K.
Bioconversion of Ginsenoside Rd into Compound K by Lactobacillus pentosus DC101 Isolated from Kimchi
Quan, Lin-Hu,Cheng, Le-Qin,Kim, Ho-Bin,Kim, Ju-Han,Son, Na-Ri,Kim, Se-Young,Jin, Hyun-O,Yang, Deok-Chun The Korean Society of Ginseng 2010 Journal of Ginseng Research Vol.34 No.4
Ginsenosides are the principal components responsible for the pharmacological and biological activities of ginseng. Ginsenoside Rd was transformed into compound K using cell-free extracts of food microorganisms, with Lactobacillus pentosus DC101 isolated from kimchi (traditional Korean fermented food) used for this conversion. The optimum time for the conversion was about 72 h at a constant pH of 7.0 and an optimum temperature of about $30^{\circ}C$. The transformation products were identified by thin-layer chromatography and high-performance liquid chromatography, and their structures were assigned using nuclear magnetic resonance analysis. Generally, ginsenoside Rd was converted into ginsenoside F2 by 36 h post-reaction. Consequently, over 97% of ginsenoside Rd was decomposed and converted into compound K by 72 h post-reaction. The bioconversion pathway to produce compound K is as follows: ginsenoside Rd$\rightarrow$ginsenoside F2$\rightarrow$compound K.