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Chun-Ying Liu,Rui-Xin Zhou,Chang-Kai Sun,Ying-Hua Jin,Hong-Shan Yu,Tian-Yang Zhang,Long-Quan Xu,Feng-Xie Jin 고려인삼학회 2015 Journal of Ginseng Research Vol.39 No.3
Background: Minor ginsenosides, those having low content in ginseng, have higher pharmacological activities. To obtain minor ginsenosides, the biotransformation of American ginseng protopanaxadiol (PPD)-ginsenoside was studied using special ginsenosidase type-I from Aspergillus niger g.848. Methods: DEAE (diethylaminoethyl)-cellulose and polyacrylamide gel electrophoresis were used in enzyme purification, thin-layer chromatography and high performance liquid chromatography (HPLC) were used in enzyme hydrolysis and kinetics; crude enzyme was used in minor ginsenoside preparation from PPD-ginsenoside; the products were separated with silica-gel-column, and recognized by HPLC and NMR (Nuclear Magnetic Resonance). Results: The enzyme molecular weight was 75 kDa; the enzyme firstly hydrolyzed the C-20 position 20- O-b-D-Glc of ginsenoside Rb1, then the C-3 position 3-O-b-D-Glc with the pathway Rb1/Rd/F2/C-K. However, the enzyme firstly hydrolyzed C-3 position 3-O-b-D-Glc of ginsenoside Rb2 and Rc, finally hydrolyzed 20-O-L-Ara with the pathway Rb2/C-O/C-Y/C-K, and Rc/C-Mc1/C-Mc/C-K. According to enzyme kinetics, Km and Vmax of MichaeliseMenten equation, the enzyme reaction velocities on ginsenosides were Rb1 > Rb2 > Rc > Rd. However, the pure enzyme yield was only 3.1%, so crude enzyme was used for minor ginsenoside preparation. When the crude enzyme was reacted in 3% American ginseng PPD-ginsenoside (containing Rb1, Rb2, Rc, and Rd) at 45C and pH 5.0 for 18 h, the main products were minor ginsenosides C-Mc, C-Y, F2, and C-K; average molar yields were 43.7% for CMc from Rc, 42.4% for C-Y from Rb2, and 69.5% for F2 and C-K from Rb1 and Rd. Conclusion: Four monomer minor ginsenosides were successfully produced (at low-cost) from the PPDginsenosides using crude enzyme.
Liu, Chun-Ying,Zhou, Rui-Xin,Sun, Chang-Kai,Jin, Ying-Hua,Yu, Hong-Shan,Zhang, Tian-Yang,Xu, Long-Quan,Jin, Feng-Xie The Korean Society of Ginseng 2015 Journal of Ginseng Research Vol.39 No.3
Background: Minor ginsenosides, those having low content in ginseng, have higher pharmacological activities. To obtain minor ginsenosides, the biotransformation of American ginseng protopanaxadiol (PPD)-ginsenoside was studied using special ginsenosidase type-I from Aspergillus niger g.848. Methods: DEAE (diethylaminoethyl)-cellulose and polyacrylamide gel electrophoresis were used in enzyme purification, thin-layer chromatography and high performance liquid chromatography (HPLC) were used in enzyme hydrolysis and kinetics; crude enzyme was used in minor ginsenoside preparation from PPD-ginsenoside; the products were separated with silica-gel-column, and recognized by HPLC and NMR (Nuclear Magnetic Resonance). Results: The enzyme molecular weight was 75 kDa; the enzyme firstly hydrolyzed the C-20 position 20-O-${\beta}$-D-Glc of ginsenoside Rb1, then the C-3 position 3-O-${\beta}$-D-Glc with the pathway $Rb1{\rightarrow}Rd{\rightarrow}F2{\rightarrow}C-K$. However, the enzyme firstly hydrolyzed C-3 position 3-O-${\beta}$-D-Glc of ginsenoside Rb2 and Rc, finally hydrolyzed 20-O-L-Ara with the pathway $Rb2{\rightarrow}C-O{\rightarrow}C-Y{\rightarrow}C-K$, and $Rc{\rightarrow}C-Mc1{\rightarrow}C-Mc{\rightarrow}C-K$. According to enzyme kinetics, $K_m$ and $V_{max}$ of Michaelis-Menten equation, the enzyme reaction velocities on ginsenosides were Rb1 > Rb2 > Rc > Rd. However, the pure enzyme yield was only 3.1%, so crude enzyme was used for minor ginsenoside preparation. When the crude enzyme was reacted in 3% American ginseng PPD-ginsenoside (containing Rb1, Rb2, Rc, and Rd) at $45^{\circ}C$ and pH 5.0 for 18 h, the main products were minor ginsenosides C-Mc, C-Y, F2, and C-K; average molar yields were 43.7% for C-Mc from Rc, 42.4% for C-Y from Rb2, and 69.5% for F2 and C-K from Rb1 and Rd. Conclusion: Four monomer minor ginsenosides were successfully produced (at low-cost) from the PPD-ginsenosides using crude enzyme.
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>
Quan, Lin-Hu,Piao, Jin-Ying,Min, Jin-Woo,Kim, Ho-Bin,Kim, Sang-Rae,Yang, Dong-Uk,Yang, Deok-Chun The Korean Society of Ginseng 2011 Journal of Ginseng Research Vol.35 No.3
Ginsenoside $Rb_1$ 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 $Rb_1$ 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 $30^{\circ}C$. Under optimal conditions, ginsenoside $Rb_1$ was 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 $Rb_1$ ${\rightarrow}$ gypenoside XVII and ginsenoside Rd${\rightarrow}$ginsenoside $F_2{\rightarrow}$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<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.
Bioconversion of Ginsenoside Rb1 to Compound K using Leuconostoc lactis DC201
Piao, Jin-Ying,Kim, Yeon-Ju,Quan, Lin-Hu,Yang, Dong-Uk,Min, Jin-Woo,Son, Seon-Heui,Kim, Sang-Mok,Yang, Deok-Chun The Plant Resources Society of Korea 2011 한국자원식물학회지 Vol.24 No.6
Ginseng (Panax ginseng) is frequently used in Asian countries as a traditional medicine. The major components of ginseng are ginsenosides. Among these, ginsenoside compound K has been reported to prevent the formation of malignancy and metastasis of cancer by blocking the formation of tumor and suppressing the invasion of cancer cells. In this study, ginsenoside $Rb_1$ was converted into compound K, via secreted ${\beta}$-glucosidase enzyme from the Leuconostoc lactis DC201 isolated, which was extracted from Kimchi. The strain DC201 was suspended and cultured in MRS broth at $37^{\circ}C$. Subsequently, the residue from the cultured broth supernatant was precipitated with EtOH and then dissolved in 20 mM sodium phosphate buffer (pH 6.0) to obtain an enzyme liquid. Meanwhile, the crude enzyme solution was mixed with ginsenoside $Rb_1$ at a ratio of 1:4 (v/v).The reaction was carried out at $30^{\circ}C$ and 190 rpm for 72 hours, and then analyzed by TLC and HPLC. The result showed that ginsenoside Rb1 was transformed into compound K after 72 hours post reaction.
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.