• Title/Summary/Keyword: ginsenoside glycoside

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Preparation and Structure Determination of a New Glycoside, (20E)-Ginsenoside $Rh_3$, and its isomer from Diol-type Ginseng Saponins (인삼의 diol계 사포닌으로부터 새로운 배당체 (20E)-Ginsenoside $Rh_3$ 및 그의 입체이성체의 제조와 구조결정)

  • 김동선;백남인;박종대;이유희;정소영;이천배;김신일
    • YAKHAK HOEJI
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    • v.39 no.1
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    • pp.85-93
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    • 1995
  • Acidic and alkaline hydrolysis of diol-type ginseng saponins produced a new glycoside, (20E)-ginsenoside Rh$_{3}$, and its stereoisomer (20Z)-, which were further subjected to alkaline by drolysis to give their aglycones, (20E)- and (20Z)-3$\beta$, 12$\beta$-dihydroxy-dammar-20(22),24-diene. The ratio of stereoisomeric mixtures was estimated to be ca. 5:1 from intensities of the peaks in $^{1}$H- and $^{13}$C-NMR spectra. The $^{1}$H- and $^{13}$C-NMR signals of ginsenoside Rh$_{3}$, which have remained unclarified, were completely assigned by the extensive application of modern NMR techniques.

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Ginsenoside $Rf_{2}$ , a New Dammarane Glycoside from Korean Red Ginseng(Panax ginseng)

  • Park, Jong-Dae;Lee, You-Hui;Kim, Shin-Il
    • Archives of Pharmacal Research
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    • v.21 no.5
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    • pp.615-617
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    • 1998
  • A new dammarane glycoside named ginsenoside $Rf_{2}$ has been isolated from Korean red ginseng (Panax ginseng) and its chemical structure has been elucidated as $6-O-[{\alpha}-L-rham-nopyranosyl (1{\rightarrow}2){\beta}-D-glucopyranosyl]$$dammarane-3{\beta}, 6{\alpa}, 12{\beta}$, 20(R), 25-pentol by chemical and spectral methods.

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Ginsenoside $Rg_5$, A Genuine Dammarane Glycoside from Korean Red Ginseng

  • Kim, Shin-Il;Park, Jeong-Hill;Ryu, Jae-Ha;Park, Jong-Dae;Lee, You-Hui;Park, Jae-Hyun;Kim, Tae-Hee;Kim, Jong-Moon;Baek, Nam-In
    • Archives of Pharmacal Research
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    • v.19 no.6
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    • pp.551-553
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    • 1996
  • A genuine dammarane glycoside, named ginsenoside $Rg_{5}$, has been isolated by repeated column chromatography and preparative HPLC from the MeOH extract of Korean red ginseng (Panax ginseng C.A. Meyer). The chemical structure of ginsenoside$ Rg_{5}$ was determined as $3-O-[{\beta}-D-glucopyranosyl (1{\rightarrow}2)-{\beta}-D-glucopyranosyl]$ dammar-20(22), $24-diene-3{\beta},12{\beta}-diol$ by spectral and chemical methods. The stereostructure of a double bond at C-20(22) of ginsenoside $Rg_{5}$ was characterized as (E) from the chemical shift of C-21 in the $^{13}C-NMR $and a NOESY experiment in the $^{1}H-NMR$.

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Regioselective Synthesis of Ginsenoside $Rh_2$ (진세노사이드 $Rh_2$의 방향선택적 합성)

  • 신명희;정지형;장은하;임광식
    • YAKHAK HOEJI
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    • v.45 no.4
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    • pp.328-333
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    • 2001
  • Ginsenoside Rh$_2$, a minor glycoside constituent of the red ginseng is known as an unique antitumor compound. Several attempts to prepare it in a large scale including semisynthesis from betulafolientriol, an 3-epimer of 20(S)-protopanaxadiol, has been reported. We have previously reported a synthesis of ginsenoside Rh$_2$from 20(S)-protopanaxadiol obtained by alkaline hydrolysis of total ginsenoside. The regioselective synthesis of this compound was achieved by protection of 12-OH group.

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Ginsenoside $Rs_3$, A genuine Dammarane-Glycoside from Korean Red Ginseng

  • Baek, Nam-In;Kim, Jong-Moon;Park, Jeong-Hill;Ryu, Jae-Ha;Kim, Dong-Seon;Lee, You-Hui;Park, Jong-Dae;Kim, Shin-Il
    • Archives of Pharmacal Research
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    • v.20 no.3
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    • pp.280-282
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    • 1997
  • A genuine dammarane-glycoside, named as ginsenoside $ Rs_3$, was isolated from the MeOH extracts of Korean red ginseng (Panax ginseng C.A. Meyer) through repeated silica gel column chromatographies and its chemical structure was determined as (20S)-protopanaxadiol $3-O-[6^{11}-O-acetyl-{\beta}-D-glucopyranosyl (1{\rightarrow2)-{\beta}-D-$glucopyranoside on the basis of several spectral and physical evidences including HMBC and FAB-MS.

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Highly Selective Production of Compound K from Ginsenoside Rd by Hydrolyzing Glucose at C-3 Glycoside Using β-Glucosidase of Bifidobacterium breve ATCC 15700

  • Zhang, Ru;Huang, Xue-Mei;Yan, Hui-Juan;Liu, Xin-Yi;Zhou, Qi;Luo, Zhi-Yong;Tan, Xiao-Ning;Zhang, Bian-Ling
    • Journal of Microbiology and Biotechnology
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    • v.29 no.3
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    • pp.410-418
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    • 2019
  • To investigate a novel ${\beta}$-glucosidase from Bifidobacterium breve ATCC 15700 (BbBgl) to produce compound K (CK) via ginsenoside $F_2$ by highly selective and efficient hydrolysis of the C-3 glycoside from ginsenoside Rd, the BbBgl gene was cloned and expressed in E. coli BL21. The recombinant BbBgl was purified by Ni-NTA magnetic beads to obtain an enzyme with specific activity of 37 U/mg protein using pNP-Glc as substrate. The enzyme activity was optimized at pH 5.0, $35^{\circ}C$, 2 or 6 U/ml, and its activity was enhanced by $Mn^{2+}$ significantly. Under the optimal conditions, the half-life of the BbBgl is 180 h, much longer than the characterized ${\beta}$-glycosidases, and the $K_m$ and $V_{max}$ values are 2.7 mM and $39.8{\mu}mol/mg/min$ for ginsenoside Rd. Moreover, the enzyme exhibits strong tolerance against high substrate concentration (up to 40 g/l ginsenoside Rd) with a molar biotransformation rate of 96% within 12 h. The good enzymatic properties and gram-scale conversion capacity of BbBgl provide an attractive method for large-scale production of rare ginsenoside CK using a single enzyme or a combination of enzymes.

Ginsenoside Rh2 Induces Apoptosis via Activation of Caspase-1 and -3 and Up-Regulation of Bax in Human Neuroblastoma

  • Kim, Young-Soak;Jin, Sung-Ha
    • Archives of Pharmacal Research
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    • v.27 no.8
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    • pp.834-839
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    • 2004
  • In human neuroblastoma SK-N-BE(2) cells undergoing apoptotic death induced by ginsenos-ide Rh2, a dammarane glycoside that was isolated from Panax ginseng C. A. Meyer, caspase-1 and caspase-3 were activated. The expression of Bax was increased in the cells treated with ginsenoside Rh2, whereas Bcl-2 expression was not altered. Treatment with caspase-1 inhibi-tor, Ac-YVAD-CMK, or caspase-3 inhibitor, Z-DEVD-FMK, partially inhibited ginsenoside Rh2-induced cell death but almost suppressed the cleavage of the 116 kDa PARP into a 85 kDa fragment. When the levels of p53 were examined in this process, p53 accumulated rapidly in the cells treated early with ginsenoside Rh2. These results suggest that activation of caspase-1 and -3 and the up-regulation of Bax are required in order for apoptotic death of SK-N-BE(2) cells to be induced by ginsenoside Rh2, and p53 plays an important role in the pathways to promote apoptosis.

Synthesis of $^3H$-Labeled dammarane triterpene glycosides of Korean ginseng

  • Han, Byung-Hoon;Woo, Lin-Keun
    • Archives of Pharmacal Research
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    • v.1 no.1
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    • pp.27-32
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    • 1978
  • A procedure of $^3H$-radio labeling synthesis for the dammarane triterpene glycosides of Korean ginseng was established by using the ginsenoside $Rg_1$ as starting material. The protons in $C-{11}$ and $C_{13}$ of the aglycone moiety of the glycoside were exchanged with tritium by keto-enol tautomerization of 12-keto-ginsenoside $Rg_1$ which was prepared by partial acetylation, Sarett oxidation and saponification, producing nona-acetate, nonaside $Rg_1$. The acety1-ketone and 12-keto-derivative of ginsenotritated ketone was reduced by metallic sodium and isoproponol to produce the end product $^3H$-ginsenoside $Rg_1$ with 3% radio-chemical recovery in one experiment.

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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.

The Effect of Ginsenosides on Galactosamine-induced Hepatotoxicity (인삼 사포닌이 간세포 독성에 미치는 영향)

  • kim, Sun-Yeou;Kim, Young-Choong;Byun, Soon-Jung;Kim, Eun
    • Korean Journal of Pharmacognosy
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    • v.22 no.4
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    • pp.219-224
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    • 1991
  • Liver protective effects of ginsenosides as well as fractions of dammarane glycosides of Panax ginseng were studied using galactosamine (GalN)-induced cytotoxicity in primary cultured rat hepatocytes. Preventing effects on GalN-induced hepatotoxicity were found both microscopic observation and determination of GPT level with total dammarane glycosides fraction and $20(S)-ginsenoside-Rb_1$ as well as $20(S)-ginsenoside-Rg_1$ at the concentration of $50{\mu}g/ml$. The syntheses of both protein and RNA were significantly increased by the treatment of $50{\mu}g/ml$ of total dammarane glycoside fraction, $20(S)-ginsenoside-Rb_1$, -Rc, -Re and $-Rg_1$, respectively in both normal and GalN-induced cytotoxic hepatocytes.

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