• 제목/요약/키워드: Ginsenoside Rf

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Identification of Dammarane-type Triterpenoid Saponins from the Root of Panax ginseng

  • Lee, Dong Gu;Lee, Jaemin;Yang, Sanghoon;Kim, Kyung-Tack;Lee, Sanghyun
    • Natural Product Sciences
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    • 제21권2호
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    • pp.111-121
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    • 2015
  • The root of Panax ginseng, is a Korea traditional medicine, which is used in both raw and processed forms due to their different pharmacological activities. As part of a continued chemical investigation of ginseng, the focus of this research is on the isolation and identification of compounds from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, semi-preparative-high performance liquid chromatography, Fast atom bombardment mass spectrometric, and nuclear magnetic resonance. Dammarane-type triterpenoid saponins were isolated from Panax ginseng root by open column chromatography, medium pressure liquid chromatography, and semi-preparative-high performance liquid chromatography. Their structures were identified as protopanaxadiol ginsenosides [gypenoside-V (1), ginsenosides-Rb1 (2), -Rb2 (3), -Rb3 (4), -Rc (5), and -Rd (6)], protopanaxatriol ginsenosides [20(S)-notoginsenoside-R2 (7), notoginsenoside-Rt (8), 20(S)-O-glucoginsenoside-Rf (9), 6-O-[$\alpha$-L-rhamnopyranosyl(1$\rightarrow$2-$\beta$-D-glucopyranosyl]-20-O-$\beta$-D-glucopyranosyl-$3\beta$,$12\beta$, 20(S)-dihydroxy-dammar-25-en-24-one (10), majoroside-F6 (11), pseudoginsenoside-Rt3 (12), ginsenosides-Re (13), -Re5 (14), -Rf (15), -Rg1 (16), -Rg2 (17), and -Rh1 (18), and vinaginsenoside-R15 (19)], and oleanene ginsenosides [calenduloside-B (20) and ginsenoside-Ro (21)] through the interpretation of spectroscopic analysis. The configuration of the sugar linkages in each saponin was established on the basic of chemical and spectroscopic data. Among them, compounds 1, 8, 10, 11, 12, 19, and 20 were isolated for the first time from P. ginseng root.

A Novel Ginsenosidase from an Aspergillus Strain Hydrolyzing 6-O-Multi-Glycosides of Protopanaxatriol-Type Ginsenosides, Named Ginsenosidase Type IV

  • Wang, Dong-Ming;Yu, Hong-Shan;Song, Jian-Guo;Xu, Yu-Feng;Liu, Chun-Ying;Jin, Feng-Xie
    • Journal of Microbiology and Biotechnology
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    • 제21권10호
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    • pp.1057-1063
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    • 2011
  • Herein, a novel ginsenosidase, named ginsenosidase type IV, hydrolyzing 6-O-multi-glycosides of protopanaxatriol-type ginsenosides (PPT), such as Re, R1, Rf, and Rg2, was isolated from the Aspergillus sp. 39g strain, purified, and characterized. Ginsenosidase type IV was able to hydrolyze the 6-O-${\alpha}$-L-($1{\rightarrow}2$)-rhamnoside of Re and the 6-O-${\beta}$-D-($1{\rightarrow}2$)-xyloside of R1 into ginsenoside Rg1. Subsequently, it could hydrolyze the 6-O-${\beta}$-D-glucoside of Rg1 into F1. Similarly, it was able to hydrolyze the 6-O-$_{\alpha}$-L-($1{\rightarrow}2$)-rhamnoside of Rg2 and the 6-O-${\beta}$-D-($1{\rightarrow}2$)-glucoside of Rf into Rh1, and then further hydrolyze Rh1 into its aglycone. However, ginsenosidase type IV could not hydrolyze the 3-O- or 20-O-glycosides of protopanaxadiol-type ginsenosides (PPD), such as Rb1, Rb2, Rb3, Rc, and Rd. These exhibited properties are significantly different from those of glycosidases described in Enzyme Nomenclature by the NC-IUBMB. The optimal temperature and pH for ginsenosidase type IV were $40^{\circ}C$ and 6.0, respectively. The activity of ginsenosidase type IV was slightly improved by the $Mg^{2+}$ ion, and inhibited by $Cu^{2+}$ and $Fe^{2+}$ ions. The molecular mass of the enzyme, based on SDS-PAGE, was noted as being approximately 56 kDa.

Re-evaluation of physicochemical and NMR data of triol ginsenosides Re, Rf, Rg2, and 20-gluco-Rf from Panax ginseng roots

  • Cho, Jin-Gyeong;In, Seo-Ji;Jung, Ye-Jin;Cha, Byeong-Ju;Lee, Dae-Young;Kim, Yong-Bum;Yeom, Myeonghun;Baek, Nam-In
    • Journal of Ginseng Research
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    • 제38권2호
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    • pp.116-122
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    • 2014
  • Ginseng roots were extracted with aqueous methanol, and extracts were suspended in water and extracted successively with ethyl acetate and n-butanol. Column chromatography using the n-butanol fraction yielded four purified triol ginseng saponins: the ginsenosides Re, Rf, Rg2, and 20-gluco-Rf. The physicochemical, spectroscopic, and chromatographic characteristics of the ginsenosides were measured and compared with reports from the literature. For spectroscopic analysis, two-dimensional nuclear magnetic resonance (NMR) methods such as $^1H$-$^1H$ correlation spectroscopy, nuclear Overhauser effect spectroscopy, heteronuclear single quantum correlation, and heteronuclear multiple bond connectivity were employed to identify exact peak assignments. Some peak assignments for previously published $^1H$-and $^{13}C$-NMR spectra were found to be inaccurate. This study reports the complete NMR assignment of 20-gluco-Rf for the first time.

HPLC SEPARATION AND QUANTITATIVE DETERMINATION OF GINSENOSIDES FROM PANAX GINSENG, PANAX QUINQUEFOLIUM AND FROM GINSENG DRUG PREPARATIONS

  • Soldati F
    • 고려인삼학회:학술대회논문집
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    • 고려인삼학회 1980년도 학술대회지
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    • pp.59-69
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    • 1980
  • A new HPLC-method for separation and quantitative determination of ginsenosides in Panax ginseng, Panax quinquefolium and in pharmaceutical drug preparations is elaborated. A reversed-phase-system with ${\mu}Bondapak\;C_{18}$ column (3.9 mm $I.D.{\times}30\;cm$) using acetonitrile-water (30:70) 2 ml/min and acetonitrile-water (18:82) 4 ml/min is suitable for the base-line separation of $Rb_1,\;Rb_2,\;Rc,\;Rd,\;Rf,\;Rg_2,\;respectively\;Re,\;Rg_1$ in 30 minutes. The ginsenosides are directly detected at 203 nm (without derivatization) with the LC-55 or LC-75 spectrophotometer (Perkin-Elmer) at $100\%$ transmission. Detection limit is 300 ng at a signal-to-noise ratio of 10:1. The ginsenosides-peak identification is carried out with HPTLC (high performance thin layer chromatography), with MIR-IR (multiple internal reflection-IR-spectros-copy) and with FD-MS (field desorption mass spectrometry). The calibration curve of each ginsenoside has a correlation coefficient very near to 1. Relative standard deviation for quantitative determinations depends upon the amount of ginsenosides and is approximately 1\%$ for ginsenoside contents of 1\%$. This method is adaptable for routine analysis in quality control laboratories.

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Antiviral effects of Korean Red Ginseng on human coronavirus OC43

  • Chi Hwan Jeong;Jisu Kim;Bo Kyeong Kim;Kang Bin Dan;Hyeyoung Min
    • Journal of Ginseng Research
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    • 제47권2호
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    • pp.329-336
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    • 2023
  • Background: Panax ginseng Meyer is a medicinal plant well-known for its antiviral activities against various viruses, but its antiviral effect on coronavirus has not yet been studied thoroughly. The antiviral activity of Korean Red Ginseng (KRG) and ten ginsenosides against Human coronavirus OC43 (HCoV-OC43) was investigated in vitro. Methods: The antiviral response and mechanism of action of KRG extract and ginsenoside Rc, Re, Rf, Rg1, Rg2-20 (R) and -20 (S), Rg3-20 (R) and -20 (S), and Rh2-20 (R) and -20 (S), against the human coronavirus strain OC43 were investigated by using plaque assay, time of addition assay, real-time PCR, and FACS analysis. Results: Virus plaque formation was reduced in KRG extract-treated and HCoV-OC43-infected HCT-8 cells. KRG extract decreased the viral proteins (Nucleocapsid protein and Spike protein) and mRNA (N and M gene) expression, while increased the expression of interferon genes. Conclusion: KRG extract exhibits antiviral activity by enhancing the expression of interferons and can be used in treating infections caused by HCoV-OC43.

인삼 1차 부산물의 생산량 및 기능성 성분 특성 (Yield and Quality Characteristics of Ginseng's First Byproducts)

  • 김관후;성봉재;김선익;한승호;김현호;이가순
    • 한국약용작물학회지
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    • 제19권5호
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    • pp.313-318
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    • 2011
  • This study was carried out to utilize the byproducts (flower, immature and mature berry, leaf and stem) of ginseng. Yield of byproducts were $32.7{\pm}9.8g$ in flower, $68.2{\pm}2.2g$ in immature berry, $48.5{\pm}4.3g$ in mature berry, $316.2{\pm}20.5g$ in leaf, and $296.6{\pm}15.4g$ in stem per $3.3m^2$ ($180{\times}90cm$, ginseng root $675.5{\pm}35.7g$/drybasis. The total saponin contents of ginseng byproducts and root are $52.36{\pm}1.24$, $68.71{\pm}1.98$, $168.89{\pm}0.57$, $68.26{\pm}1.32$, $7.85{\pm}0.61$ and $35.08{\pm}0.96$ mg/g, respectively. The main ginsenoside of all byproducts was Re and the highest content was $132.23{\pm}1.56$ mg/g in mature berry. But flower and berry was not detected Rf and Rh1, respectively. Total polyphenolic compound content on mature berry was the highest, $2.242{\pm}0.140%$, after, immature berry > leaf > flower > root > stem order. The DPPH radical scavenging activity on mature berry was the highest, $0.115{\pm}0.004$ mg/mL($IC_{50}$), and the others were the same order of polyphenolic compound and ginsenoside content on byproducts.

Use of Gold Nanoparticle Fertilizer Enhances the Ginsenoside Contents and Anti-Inflammatory Effects of Red Ginseng

  • Kang, Hee;Hwang, Yun-Gu;Lee, Taek-Guen;Jin, Cheng-Ri;Cho, Chi Heung;Jeong, Hee-Yeong;Kim, Dae-Ok
    • Journal of Microbiology and Biotechnology
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    • 제26권10호
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    • pp.1668-1674
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    • 2016
  • Red ginseng, a steamed and sun-dried ginseng, is a popular health-promoting food in Korea and other Asian countries. We introduced nanofertilizer technology using gold nanoparticles in an effort to develop red ginseng with an elevated level of ginsenosides, the main active compounds of ginseng. Shoots of 6-year-old ginseng plants were fertilized three times with colloidal gold nanoparticle sprays. Red ginseng extract was prepared from the main roots. The concentrations of gold and ginsenosides were measured following gold nanoparticle treatment. To evaluate the anti-inflammatory effects, mouse peritoneal macrophages of male BALB/c mouse were stimulated with lipopolysaccharide plus interferon-γ in the presence of extracts from red ginseng with or without gold nanoparticle treatment. The content of ginsenosides, such as Rg1, Re, Rf, and Rb1, increased in ginseng treated with gold nanofertilizer whereas the steaming process increased only the levels of Rd and Rg3. The levels of nitric oxide, inducible nitric oxide synthase, and interleukin-6, but not tumor necrosis factor-α, were more suppressed in macrophages treated with extract from gold nanoparticle-treated red ginseng. Our results show that the use of a colloidal gold nanoparticle fertilizer improved the synthesis of ginsenosides in ginseng and enhanced the anti-inflammatory effects of red ginseng. Further research is required to elucidate the causal factors for the gold-induced change in ginsenoside synthesis and to determine the in vivo effect of gold nanoparticle-treated ginseng.

Carbohydrate and Ginsenoside Changes in Ginseng Roots Grown in the Bay of Plenty, New Zealand

  • Follett John M.;Proctor John T.A.;Walton Eric F.;Boldingh Helen L.;McNamara Catherine;Douglas James A.
    • Journal of Ginseng Research
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    • 제28권4호
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    • pp.165-172
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    • 2004
  • Ginseng is traditionally cultivated worldwide in cold continental climates. It is now also being cultivated in maritime environments such as New Zealandis. This paper reports a number of growth and quality parameters for plants grown under those conditions over two growing seasons and the intervening winter dormant period. While shoot biomass peaked mid-summer, in contrast, root biomass peaked late autumn/early winter. Starch, sucrose, fructose, glucose and inositol were detected in the roots. Starch concentrations were highest in early autumn (mean 470 mg $g^{-1}$ dry weight) and lowest in mid spring (218 mg $g^{-1}$ dry weight). Sucrose concentrations were low during early summer until late autumn but increased rapidly with the onset of winter and peaked during mid spring (168 mg $g^{-1}$ dry weight). Fructose and glucose concentrations were similar and peaked in late spring (5.3 and 6.2 mg $g^{-1}$ dry weight). Inositol concentrations peaked in mid summer (1.7 mg $g^{-1}$ dry weight). Starch/sugar ratios were high during summer and autumn and low during winter and spring. Ginsenoside concentrations and profiles showed that the six major ginsenosides, Rgl, Re, Rb1, Rc, Rb2 and Rd, were present, but Rf was absent. Concentrations did not vary with sampling date. The most abundant ginsenosides were Re (15.9 to 17.5 mg $g^{-1}$ dry weight) and Rb1 (10.7 to 18.1 mg $g^{-1}$ dry weight). Combined, they accounted for < $75{\%}$ of total ginsenoside concentrations. Limited taste tests indicated that highest root quality occurred during late autumn, after the shoots had senesced. However, quality could not be related to plant chemistry.

Comparison of Preparation Methods for the Quantification of Ginsenosides in Raw Korean Ginseng

  • Hong, Hee-Do;Sim, Eun-Mi;Kim, Kyung-Tack;Rho, Jeong-Hae;Rhee, Young-Kyung;Cho, Chang-Won
    • Food Science and Biotechnology
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    • 제18권2호
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    • pp.565-569
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    • 2009
  • This study was conducted to evaluate the effects of different preparation methods on the recovery and quantification of ginsenosides in raw Korean ginseng (Panax ginseng C.A. Meyer). Eight major ginsenosides ($Rb_1$, $Rb_2$, $Rb_3$, Rc, Rd, Re, Rf, and $Rg_1$) were analyzed by high performance liquid chromatography (HPLC), after which the recovery and repeatability of the extraction of those ginsenosides using 3 different preparation methods were compared [A. direct extraction (DE) method, hot MeOH extraction/evaporation/direct dissolution; B. solid phase extraction (SPE) method, hot MeOH extraction/evaporation/dissolution/$C_{18}$ cartridge adsorption/MeOH elution; C. liquid-liquid extraction (LLE) method, hot MeOH extraction/evaporation/dissolution/n-BuOH fractionation]. Use of the DE method resulted in a significantly higher recovery of total ginsenosides than other methods and a relatively clear peak resolution. Use of the SPE and LLE methods resulted in clearer peak resolution, but lower ginsenoside recovery than the DE method. The LLE method showed the lowest ginsenoside recovery and repeatability among the 3 methods. Given that the DE method employed only extraction, evaporation, and a dissolution step (avoiding complicate and time consuming purification), this technique may be an effective method for the preparation and quantification of ginsenosides from raw Korean ginseng.

Discrimination of white ginseng origins using multivariate statistical analysis of data sets

  • Song, Hyuk-Hwan;Moon, Ji Young;Ryu, Hyung Won;Noh, Bong-Soo;Kim, Jeong-Han;Lee, Hyeong-Kyu;Oh, Sei-Ryang
    • Journal of Ginseng Research
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    • 제38권3호
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    • pp.187-193
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    • 2014
  • Background: White ginseng (Panax ginseng Meyer) is commonly distributed as a health food in food markets. However, there is no practical method for distinguishing Korean white ginseng (KWG) from Chinese white ginseng (CWG), except for relying on the traceability system in the market. Methods: Ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry combined with orthogonal partial least squares discrimination analysis (OPLS-DA) was employed to discriminate between KWG and CWG. Results: The origins of white ginsengs in two test sets ($1.0{\mu}L$ and $0.2{\mu}L$ injections) could be successfully discriminated by the OPLS-DA analysis. From OPLS-DA S-plots, KWG exhibited tentative markers derived from ginsenoside Rf and notoginsenoside R3 isomer, whereas CWG exhibited tentative markers derived from ginsenoside Ro and chikusetsusaponin Iva. Conclusion: Results suggest that ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry coupled with OPLS-DA is an efficient tool for identifying the difference between the geographical origins of white ginsengs.