• Title/Summary/Keyword: Ginsenoside F1

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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.

Enzymatic formation of compound-K from ginsenoside Rb1 by enzyme preparation from cultured mycelia of Armillaria mellea

  • Upadhyaya, Jitendra;Kim, Min-Ji;Kim, Young-Hoi;Ko, Sung-Ryong;Park, Hee-Won;Kim, Myung-Kon
    • Journal of Ginseng Research
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    • v.40 no.2
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    • pp.105-112
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    • 2016
  • Background: Minor saponins or human intestinal bacterial metabolites, such as ginsenosides Rg3, F2, Rh2, and compound K, are more pharmacologically active than major saponins, such as ginsenosides Rb1, Rb2, and Rc. In this work, enzymatic hydrolysis of ginsenoside Rb1 was studied using enzyme preparations from cultured mycelia of mushrooms. Methods: Mycelia of Armillaria mellea, Ganoderma lucidum, Phellinus linteus, Elfvingia applanata, and Pleurotus ostreatus were cultivated in liquid media at $25^{\circ}C$ for 2 wk. Enzyme preparations from cultured mycelia of five mushrooms were obtained by mycelia separation from cultured broth, enzyme extraction, ammonium sulfate (30-80%) precipitation, dialysis, and freeze drying, respectively. The enzyme preparations were used for enzymatic hydrolysis of ginsenoside Rb1. Results: Among the mushrooms used in this study, the enzyme preparation from cultured mycelia of A. mellea (AMMEP) was found to convert ginsenoside Rb1 into compound K with a high yield, while those from G. lucidum, P. linteus, E. applanata, and P. ostreatus produced remarkable amounts of ginsenoside Rd from ginsenoside Rb1. The enzymatic hydrolysis pathway of ginsenoside Rb1 by AMMEP was $Rb1{\rightarrow}Rd{\rightarrow}F2{\rightarrow}$ compound K. The optimum reaction conditions for compound K formation from ginsenoside Rb1 were as follows: reaction time 72-96 h, pH 4.0-4.5, and temperature $45-55^{\circ}C$. Conclusion: AMMEP can be used to produce the human intestinal bacterial metabolite, compound K, from ginsenoside Rb1 with a high yield and without food safety issues.

Ginsenoside F4 inhibits platelet aggregation and thrombus formation by dephosphorylation of IP3RI and VASP

  • Shin, Jung-Hae;Kwon, Hyuk-Woo;Lee, Dong-Ha
    • Journal of Applied Biological Chemistry
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    • v.62 no.1
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    • pp.93-100
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    • 2019
  • The root of Panax ginseng is used in ethnomedicine throughout eastern Asia and various recent studies have proved that Panax ginseng has inhibitory effects on cardiovascular disease. Each factor causing cardiovascular disease is known to have a very complex process which is achieved by a diverse number of mechanisms. Among these factors, platelets are the most important because they directly participate in thrombogenesis. Therefore, inhibiting the activity of platelets is an essential element for prevention of cardiovascular diseases. Our previous study showed the antiplatelet effects of Korean red ginseng extract and two of its components, ginsenoside Rg3 and ginsenoside Ro. However, the inhibitory mechanism of other ginsenosides remains unclear. Therefore, we investigated the inhibitory mechanism of ginsenoside F4 (G-F4) from Korean red ginseng on the regulation of signaling molecules involved in human platelet aggregation. With the use of G-F4, collagen-induced human platelet aggregation was inhibited in a dose-dependent manner, and it suppressed collagen-induced elevation of $[Ca^{2+}]_i$ mobilization through elevated phosphorylation of inositol 1, 4, 5-triphosphate receptor I ($Ser^{1756}$). In addition, G-F4 inhibited fibrinogen binding to ${\alpha}IIb/{\beta}_3$ during collagen-induced human platelet aggregation. Thus, in the present study, G-F4 showed an inhibitory effect on human platelet activation, suggesting its potential use as a new natural medicine for preventing platelet-mediated cardiovascular diseases.

Influences of Fusurium sozani and Phytophthoya cactorum on the Changes in Saponin Components of Korean Ginseng (Panax ginseng C.A. Meyer) (Fusarium solani와 Phytophlhora cactorum이 고려인삼의 사포닌 성분변화에 미치는 영향)

  • 조대휘;오승환
    • Journal of Ginseng Research
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    • v.10 no.1
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    • pp.66-75
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    • 1986
  • Influnces of Fuiarium solani and Phytophthora cactorum infection on the changes in saponin components of Korean ginseng (Panax ginseng C.A. Meyer)roots and some of the biology of those fungi in relation to ginseng root were investigated. Mycelial growth of F. solani was decreased as increasing concentration of the water extracts of fresh ginseng roots, while that of P. cactorum was increased as increasing the concentration of the water extracts and crude saponin. Mycelial growth of F. solani, however, was increased as increasing concentration of crude ginseng saponin upto 20 ppm, while it was tended to be decreased when the concentration was higher than 50 ppm. Nystatin also suppresed the growth of F. solani as increasing its concentration, but it did not affected on the growth of p. cactorum. Ginsenoside Ra and Ro components were not detected in ginseng roots inoculated with F. solani or P. cactorum. Panaxadiol gisenosides were increased by 3.0%, whereas panaxatriol ginsenosides were decreased by 34.9% in ginseng roots inoculated with F. iolani. In ginseng roots inoculated with P. cactorum panaxadiol ginsenosides were increased by 21.1%, but panaxatriol ginsenosides were decreased by 23.5%. PD/PT ratio in ginseng roots inoculated with F. solani or P. cactorum were equally increased by 58.4% in spite of differences in the change of panaxadiol and panaxatriol ginsenosides. The total saponin components of ginseng roots inoculated with F. solani or P. cactorum were decreased by 17.8% and 2.5%, respectively.

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Conversion of Ginsenosides by 9 Repetitive Steamings and Dryings Process of Korean Ginseng Root and Its Inhibition of BACE-1 Activity (인삼의 구증구포에 의한 Ginsenoside의 성분변화 및 BACE-1 억제효과)

  • Kim, Do-Wan;Kim, Yu-Jin;Lee, Yun-Jin;Min, Jin-Woo;Kim, Se-Young;Yang, Deok-Chun
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.22 no.6
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    • pp.1557-1561
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    • 2008
  • Red ginseng possibly has new ingredients converted during steaming and dry process from fresh ginseng. Kujeungkupo method which means 9 repetitive steamings and dryings process was used for the production of red ginseng from 6-year old ginseng roots. Saponin was extracted from each red ginseng produced at the 1st, 3rd, 5th, 7th, and 9th during the steaming and drying treatment, and we analyzed saponin content with TLC. Minor saponins, such as ginsenoside-Rg3, -Rh2, compound K, and F2, increased as the process time of steaming and drying, but major saponins (ginsenoside-Rb1, -Rb2, -Rc, -Rd, -Re, -Rf, -Rg1) were decreased. Major saponins were yet observed almost at the 1st process, then degraded as the increasing time of steaming and drying process. Especially, ginsenoside-Re and -Rg were observed as considerable amount after the 1st treatment, but there were no trace of them after the 9th treatment. Ginsenoside-Rg1, -Rb2, and -Rb1 were also reduced remarkedly by 96.6%, 96%, and 92.3%, respectively. Minor saponins were increased significantly, especially for ginsenoside-Rg3 and ginsenoside-F2. These results suggest that Kujeungkupo method is the very useful method for the production of minor ginsenoside-Rg3 and -Rh2.

Microbial conversion of major ginsenosides in ginseng total saponins by Platycodon grandiflorum endophytes

  • Cui, Lei;Wu, Song-quan;Zhao, Cheng-ai;Yin, Cheng-ri
    • Journal of Ginseng Research
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    • v.40 no.4
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    • pp.366-374
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    • 2016
  • Background: In this study, we screened and identified an endophyte JG09 having strong biocatalytic activity for ginsenosides from Platycodon grandiflorum, converted ginseng total saponins and ginsenoside monomers, determined the source of minor ginsenosides and the transformation pathways, and calculated the maximum production of minor ginsenosides for the conversion of ginsenoside Rb1 to assess the transformation activity of endophyte JG09. Methods: The transformation of ginseng total saponins and ginsenoside monomers Rb1, Rb2, Rc, Rd, Rg1 into minor ginsenosides F2, C-K and Rh1 using endophyte JG09 isolated by an organizational separation method and Esculin-R2A agar assay, as well as the identification of transformed products via TLC and HPLC, were evaluated. Endophyte JG09 was identified through DNA sequencing and phylogenetic analysis. Results: A total of 32 ${\beta}$-glucosidase-producing endophytes were screened out among the isolated 69 endophytes from P. grandiflorum. An endophyte bacteria JG09 identified as Luteibacter sp. effectively converted protopanaxadiol-type ginsenosides Rb1, Rb2, Rc, Rd into minor ginsenosides F2 and C-K, and converted protopanaxatriol-type ginsenoside Rg1 into minor ginsenoside Rh1. The transformation pathways of major ginsenosides by endophyte JG09 were as follows: $Rb1{\rightarrow}Rd{\rightarrow}F2{\rightarrow}C-K$; $Rb2{\rightarrow}C-O{\rightarrow}C-Y{\rightarrow}C-K$; $Rc{\rightarrow}C-Mc1{\rightarrow}C-Mc{\rightarrow}C-K$; $Rg1{\rightarrow}Rh1$. The maximum production rate of ginsenosides F2 and C-K reached 94.53% and 66.34%, respectively. Conclusion: This is the first report about conversion of major ginsenosides into minor ginsenosides by fermentation with P. grandiflorum endophytes. The results of the study indicate endophyte JG09 would be a potential microbial source for obtaining minor ginsenosides.

Gram-Scale Production of Ginsenoside F1 Using a Recombinant Bacterial β-Glucosidase

  • An, Dong-Shan;Cui, Chang-Hao;Siddiqi, Muhammad Zubair;Yu, Hong Shan;Jin, Feng-Xie;Kim, Song-Gun;Im, Wan-Taek
    • Journal of Microbiology and Biotechnology
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    • v.27 no.9
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    • pp.1559-1565
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    • 2017
  • Naturally occurring ginsenoside F1 (20-O-${\beta}$-$\text\tiny{D}$-glucopyranosyl-20(S)-protopanaxatriol) is rare. Here, we produced gram-scale quantities of ginsenoside F1 from a crude protopanaxatriol saponin mixture comprised mainly of Re and Rg1 through enzyme-mediated biotransformation using recombinant ${\beta}$-glucosidase (BgpA) cloned from a soil bacterium, Terrabacter ginsenosidimutans Gsoil $3082^T$. In a systematic step-by-step process, the concentrations of substrate, enzyme, and NaCl were determined for maximal production of F1. At an optimized NaCl concentration of 200 mM, the protopanaxatriol saponin mixture (25 mg/ml) was incubated with recombinant BgpA (20 mg/ml) for 3 days in a 2.4 L reaction. Following octadecylsilyl silica gel column chromatography, 9.6 g of F1 was obtained from 60 g of substrate mixture at 95% purity, as assessed by chromatography. These results represent the first report of gram-scale F1 production via recombinant enzyme-mediated biotransformation.

Preparation of minor ginsenosides C-Mc, C-Y, F2, and C-K from American ginseng PPD-ginsenoside using special ginsenosidase type-I from Aspergillus niger g.848

  • Liu, Chun-Ying;Zhou, Rui-Xin;Sun, Chang-Kai;Jin, Ying-Hua;Yu, Hong-Shan;Zhang, Tian-Yang;Xu, Long-Quan;Jin, Feng-Xie
    • Journal of Ginseng Research
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    • v.39 no.3
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    • pp.221-229
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    • 2015
  • 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.

Pharmacological studies of some oriental Medicinals (동양약물의 약리학적 연구)

  • Takagi, Keijiro
    • YAKHAK HOEJI
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    • v.17 no.1
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    • pp.1-8
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    • 1973
  • The pharmacological activities of paeoniflorin abtained from paeony roots, F$_M$100 from glycyrrhiza roots, crude saikosides from bupleurum roots, crude platycodin from platycodon roots, and bothj of ginsenoside Rb and ginsenoside Rg series from ginseng roots were investigated. Paeoniflorin, F$_M$ 100, crude saikosides, and crude platycodin exhibited sedative antipyretic, anlagesic and anti-ulcerative actions. In addition, crude saidosides and crude platycodin showed antitusaive and the potent anti-inflammatory action. An expectorant action was also observed with crude platycodin. These results coincided with the clinical applications of the aforementioned oriental medicinals. It also should be noted that crude saikosides nad crude platycodin are preferable to the other steroidal nad nonsteroidal drugs as an anti-inflammatory agent, because the drugs aggravate the digestive ulcer. In ginseng, G No3. and GNS frctions out of ginsenoside Rb series hsowed stimulant and antifatigue actions. The synergistic effects identified between paeoniflorin and F$_M$ 100 on the various pharmacological activities, have verified the reasonability of combined uses of two oriental drugs as Jakyak Gaqmcho-Tang.

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