• Title, Summary, Keyword: ginsenoside

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Specific Conversion of Ginseng Saponin by the Enzyme of Rhizopus japonicus (Rhizopus japonicus의 효소(酵素)에 의한 인삼(人蔘) 사포닌의 선택적(選擇的) 전환(轉換))

  • Kim, Sang-Dal;Seu, Jung-Hwn
    • The Korean Journal of Mycology
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    • v.14 no.3
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    • pp.195-200
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    • 1986
  • The enzyme produced by a strain of Rhizopus japonicus was able to covert selectively ginsenoside $Rb_1$ which was the most abundant ginseng saponin, into ginsenoside Rd which was known to be superior to ginsenoside $Rb_1$ pharmaceutically. This specific conversion of ginsenoside $Rb_1$ without any change of other ginsenoside patterns was confirmed by thin layer chromatography and high performance liquid chromatograpy quantitatively. The amount of ginsenoside Rd was increased to 4.8 and 34.7 folds by enzymatic conversion of ginsenoside $Rb_1$ in total saponin and ginsenoside Rb group saponin, respectively. The increased amount of ginsenoside Rd corresponded to total amount of released glucose and decreased amount of ginsenoside $Rb_1$ accurately.

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Conversion of Ginseng Saponin with the Enzyme Produced by Rhizopus sp. (Part 1) Confirmation of Conversion of Ginsenoside- Rb$_1$to Ginsenoside-Rd (Rhizopus sp.가 생산하는 효소에 의한 인삼 Saponin의 전환 (제1보) Ginsenoside-Rb$_1$에서 Ginsenoside-Rd로의 전환확인)

  • 김상달;서정훈
    • Microbiology and Biotechnology Letters
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    • v.10 no.4
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    • pp.267-273
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    • 1982
  • Among 12 kinds of ginsenosides in ginseng saponin, ginsenoside-Rb$_1$was contained the most abundantly. But ginsenoside-Rd which is similar to ginsenoside-Rb$_1$in structure, was known to be superior to ginsenoside-Rb$_1$pharmaceutically. In order to convert ginsenoside-Rb$_1$into ginsenoside-Rd by microbial enzyme treatment, a Rhizopus sp. was selected among various strais of molds found in rotten ginseng roots. Enzyme was prepared from the extract of wheat bran koji culture by ammonium sulfate precipitation (1.0 sat'd) and succeeding ammonium sulfate fractionation method (0.6-0.9 sat'd). For the purpose of use as substrate, saponins were purified by the several purification steps from alcohol extract of red ginseng roots. We obtained the total saponin which was composed of 36.5% of ginsenoside Rb$_1$, 12.2% of ginsenoside-Rd and other ginsenosides. For increase of ginsenoside-Rb$_1$ component ratio, we also obtained further purified ginsenoside-Rb group saponin containing 54.5% of ginsenoside-Rb$_1$, 1.1% of ginsenoside- Rd and other ginsenosides from purified the total saponin. In the enzymatic reaction system including the total saponin or the ginsenoside-Rb group saponin, we confirmed the specific conversion of ginsenoside-Rb$_1$to ginsenoside-Rd proportionally and no change of any other ginsenoside patterns by thin layer chromatography and high performance liquid chromatography.

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Transformation of Ginseng Saponins to Ginsenoside $Rh_2$ by Acids and Human Intestinal Bacteria Activities of Their Transformants

  • Bae, Eun-Ah;Han, Myung-Joo;Kim, Eun-Jin;Kim, Dong-Hyun
    • Archives of Pharmacal Research
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    • v.27 no.1
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    • pp.61-67
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    • 2004
  • When ginseng water extract was incubated at $60^{\circ}C$ in acidic conditions, its protopanaxadiol ginsenosides were transformed to ginsenoside $Rg_3$ and ${\Delta}^{20}$-ginsenoside $Rg_3$. However, protopanaxadiol glycoside ginsenosides $Rb_1, Rb_2$ and Rc isolated from ginseng were mostly not transformed to ginsenoside $Rg_3$ by the incubation in neutral condition. The transformation of these ginsenosides to ginsenoside $Rg_3$ and ${\Delta}^{20}$-ginsenoside $Rg_3$ was increased by increasing incubation temperature and time in acidic condition: the optimal incubation time and temperature for this transformation was 5 h and $60^{\circ}C$ resepectively. The transformed ginsenoside $Rg_3$ and ${\Delta}^{20}$-ginsenoside $Rg_3$ were metabolized to ginsenoside $Rh_2$ and $\Delta^{20}$--ginsenoside $Rh_2$, respectively, by human fecal microflora. Among the bacteria isolated from human fecal microflora, Bacteroides sp., and Bifidobacterium sp. and Fusobacterium sp. potently transformed ginsenoside $Rg_3$ to ginsenoside $Rh_2$. Acid-treated ginseng (AG) extract, fermented AG extract, ginsenoside $Rh_2$ and protopanaxadiol showed potent cytotoxicity against tumor cell lines. AG extract, fermented AG extract and protopanaxadiol potently inhibited the growth of Helicobacter pylori.

Preparation of a 20(R)-Ginsenoside $Rh_2$ and the 20(S) Epimer from Protopanaxadiol Saponins of Panax ginseng C.A. Meyer (인삼의 Protopanaxadiol계 사포닌으로부터 20(R)-Ginsenoside $Rh_2$ 및 20(S) 이성체의 제조)

  • 김신일;백남인;김동선;이유희;강규상;박종대
    • YAKHAK HOEJI
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    • v.35 no.5
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    • pp.432-437
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    • 1991
  • A mixture of 20(R)- and 20(S)-ginsenoside Rg$_{3}$ was obtained under mild acidic hydrolysis from protopanaxadiol saponins, ginsenosides Rb$_{1}$, Rb$_{2}$, Rc and Rd. The product was acetylated to give the peracetates, which were further converted into 20(R)-ginsenoside Rg$_{3}$, 20(S)-ginsenoside Rg$_{3}$, 20(R)-ginsenoside Rh$_{2}$ and 20(S)-ginsenoside Rh$_{2}$ by the direct alkaline treatment depending upon two kinds of temperature conditions respectively. The structure and physicochemical properties of a prosapogenin, 20(R)-ginsenoside Rh$_{2}$, were investigated.

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Ginsenosides from the Roots of Korean Cultivated-Wild Ginseng

  • Yang, Min-Cheol;Seo, Dong-Sang;Hong, Jong-Ki;Hong, Sung-Hyun;Kim, Young-Choong;Lee, Kang-Ro
    • Natural Product Sciences
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    • v.14 no.3
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    • pp.171-176
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    • 2008
  • Column chromatographic separation of 70% EtOH extract of the roots of Korean cultivated-wild ginseng led to the isolation of ten ginsenosides (1 - 10). The isolated compounds were identified as ginsenoside $Rg_1$ (1), ginsenoside Re (2), ginsenoside Rc (3), ginsenoside $Rb_1$ (4), ginsenoside $Rb_2$ (5), ginsenoside Rd (6), ginsenoside $Rg_3$ (7), ginsenoside $F_2$ (8), ginsenoside $Rb_3$ (9), and ginsenoside $Rd_2$ (10) by physicochemical and spectroscopic methods. The compounds (1 - 10) were for the first time isolated from the roots of Korean cultivated-wild ginseng.

Biotransformation of Ginsenoside Rb1 to Prosapogenins, Gypenoside XVII, Ginsenoside Rd, Ginsenoside F2, and Compound K by Leuconostoc mesenteroides DC102

  • Quan, Lin-Hu;Piao, Jin-Ying;Min, Jin-Woo;Kim, Ho-Bin;Kim, Sang-Rae;Yang, Dong-Uk;Yang, Deok-Chun
    • Journal of Ginseng Research
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    • v.35 no.3
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    • pp.344-351
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    • 2011
  • 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.

Patterns and Contents of Ginsenoside in Normal Root Parts and Hairy Root Lines of Panax ginseng C. A. Meyer (인삼 뿌리 부위별 및 모상근 세포주간 ginsenoside 양상 및 함량)

  • 양덕춘;양계진
    • Korean Journal of Plant Tissue Culture
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    • v.27 no.6
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    • pp.485-489
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    • 2000
  • The patterns and contents of ginsenosides were examined in normal root parts and hairy root lines of Panax ginseng C. A. Meyer. Ginsenoside-Rb$_1$, -Rb$_2$, -Rc, -Rd, -Re, -Rf, -Rg$_1$, -Rg$_2$ were detected in normal roots and hairy roots of ginseng. The patterns and contents of ginsenosides in that were very difference each other. The contents of total ginsenoside of hairy root (KGHR-1) was 17.42 mg/g dry wt, it's highest compared to others. Ginsenoside contents of hairy root (KGHR-1) was higher on ginsenoside-Rd, Rg$_1$, KGHR-5 was higher on ginsenoside-Rb$_1$, Rg$_1$, and KGHR-8 was higher on ginsenoside-Rd, Re than others. The contents of total ginsenosides on 6 years old ginseng cultured in the field were high in the order of main root, lateral root and fine roots, and content of ginsenosides in fine roots was 3.2 times higher than that in main root. The ratio of ginsenoside-Rg$_1$to total ginsenosides were about 3.43%, 8.68% and 14.18% respectively on fine root, lateral root and main root, it's very lower than that in hairy roots. It is suggested that specific ginsenosides can be produce in cultures of ginseng hairy roots.

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Metabolism of Ginsenoside Rg5, a Main Constituent Isolated from Red Ginseng, by Human Intestinal Microflora and Their Antiallergic Effect

  • Shin, Yong-Wook;Bae, Eun-Ah;Han, Myung-Joo;Kim, Dong-Hyun
    • Journal of Microbiology and Biotechnology
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    • v.16 no.11
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    • pp.1791-1798
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    • 2006
  • When ginsenoside Rg5, a main component isolated from red ginseng, was incubated with three human fecal microflora for 24 h, all specimens showed hydrolyzing activity: all specimens produced ginsenoside Rh3 as a main metabolite, but a minor metabolite $3{\beta},12{\beta}$-dihydroxydammar-21(22),24-diene (DD) was observed in two specimens. To evaluate the antiallergic effect of ginsenoside Rg5 and its metabolites, the inhibitory effect of ginsenoside Rg5 and its metabolite ginsenoside Rh3 against RBL-2H3 cell degranulation, mouse passive cutaneous anaphylaxis (PCA) reaction induced by the IgE-antigen complex, and mouse ear skin dermatitis induced by 12-O-tetradecanoilphorbol-13-acetate (TPA) were measured. Ginsenosides Rg5 and Rh3 potently inhibited degranulation of RBL-2H3 cells. These ginsenosides also inhibited mRNA expression of proinflammatory cytokines IL-6 and $TNF-{\alpha}$ in RBL-2H3 cells stimulated by IgE-antigen. Orally and intraperitoneally administered ginsenoside Rg3 and orally administered ginsenoside Rg5 to mice potently inhibited the PCA reaction induced by IgE-antigen complex. However, intraperitoneally administered ginsenoside Rg5 nearly did not inhibit the PCA reaction. These ginsenosides not only suppressed the swelling of mouse ears induced by TPA, but also inhibited mRNA expression of cyclooxygenase-2, $TNF-{\alpha}$, and IL-4 and activation of transcription factor NF-kB. These inhibitions of ginsenoside Rh3 were more potent than those of ginsenoside Rg5. These findings suggest that ginsenoside Rg5 may be metabolized in vivo to ginsenoside Rh3 by human intestinal microflora, and ginsenoside Rh3 may improve antiallergic diseases, such as rhinitis and dermatitis.

Inhibitory Effect of Ginsenoside Rg5 and Its Metabolite Ginsenoside Rh3 in an Oxazolone-Induced Mouse Chronic Dermatitis Model

  • Shin, Yong-Wook;Bae, Eun-Ah;Kim, Dong-Hyun
    • Archives of Pharmacal Research
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    • v.29 no.8
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    • pp.685-690
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    • 2006
  • The effect of a main constituent ginsenoside Rg5 isolated from red ginseng and its metabolite ginsenoside Rh3 in a chronic dermatitis model was investigated. Ginsenosides Rg5 and Rh3 suppressed swelling of oxazolone-induced mouse ear contact dermatitis. These ginsenosides also reduced mRNA expressions of cyclooxygenase-2, interleukin $(IL)-1{\beta}$, tumor necrosis factor $(TNF)-{\alpha}$ and interferon $(IFN)-{\gamma}$. The inhibition of ginsenoside Rh3 was more potent than that of ginsenoside Rg5. These findings suggest that ginsenoside Rh3 metabolized from ginsenoside Rg5 may improve chronic dermatitis or psoriasis by the regulation of $IL-1{\beta}$ and $TNF-{\alpha}$ produced by macrophage cells and of $IFN-{\gamma}$ produced by Th cells.