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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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    • v.21 no.2
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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.

Changes of Antioxidant Activity and Lignan Contents in Schisandra chinensis by Harvesting Times (수확시기에 따른 오미자의 항산화 활성과 리그난 성분 함량 변화)

  • Choi, So-Ra;Kim, Chang-Su;Kim, Jong-Yeob;You, Dong-Hyun;Kim, Jeong-Man;Kim, Young-Sun;Song, Eun-Ju;Kim, Young-Gook;Ahn, Young-Seob;Choi, Dong-Guen
    • Korean Journal of Medicinal Crop Science
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    • v.19 no.6
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    • pp.414-420
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    • 2011
  • We investigated antioxidant activity and lignan contents by harvesting times to expand use of Schisandra chinensis (Turcz.) Baillon. Total polyphenol and flavonoid contents of seed was higher than those of flesh but there is not much difference in harvesting times. As $RC_{50}$ value, that was, the concentration of sample required for 50% reduction of 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical, was 13.7~24.2 ${\mu}g/m{\ell}$ in seed thus it showed a high antioxidant activity. Among lignan components, schizandrin content was the highest and followed by gomisin N and gomisin A in all of flesh and seed. Also these components in seed were 4~9 times more contained than those of flesh. All of them were decreased by harvesting times in flesh. But the contents of schizandrin and gomisin N were high in August 3rd and September 15th in seed, respectively. As the results, the seed of S. chinensis had high antioxidant activity and lignan contents so it could be potentially developed as a resource.

Analytical Optimum of Ginsenosides according to the Gradient Elution of Mobile Phase in High Performance Liquid Chromatography (HPLC의 이동상 용매조건에 따른 인삼 Ginsenoside 분석)

  • Park, Ji-Yeong;Won, Jun-Yeon;Lee, Chung-Yeol
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.3
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    • pp.215-219
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    • 2007
  • This study was conducted to analyze not only for the quality guaranteed of red ginseng but also for the minor ginsenosides. Although several studies have reported to analyze ginseng saponins, those were focused to major saponins, including 6 to 7 ginsenosides. As increase of interest in medicinal effect of ginseng products, anasis of various ginsenosides in both red and white ginseng are strongly demanded. To perform optital condition of 12 ginsenoside analysis, We controlled HPLC conditions, such as the gradient elution of the mobile phase. We found the adequate separation method for 12 ginse-nosides. The optimum condition was as following : H$_2$O/CH$_3$CN ratios were 82/18, 70/30, 55/45 and 50/50, respectively. Sol-vent flow rate was 1.00 ma/min. Column temperature was kept to 35$^{\circ}$C. UV detector was set to 203 nm.

Comparison of Malonyl Ginsenoside Contents in Parts of Korean Ginseng (고려인삼의 부위별 Malonyl Ginsenoside 함량 비교 분석)

  • Park, Young Sik;Oh, Myeong Hwan;Lee, Hwan;Jung, Jong Tae;Jo, Yun Ho;Pyo, Mi Kyung
    • Korean Journal of Pharmacognosy
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    • v.48 no.1
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    • pp.82-87
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    • 2017
  • Malonyl ginsenoside content of the Panax ginseng C.A. Meyer is known to account for 35% to 60% of total ginsenosides content. However, its distribution by ginseng part has not been studied. In this study, four kinds of malonyl ginsenosides were compared in Korean white ginseng part using the purified malonyl ginsenoside standards in our laboratory. White ginseng was prepared by the freeze drying ($-70^{\circ}C$, 48 h) or air drying ($50^{\circ}C$, 48 h) methods form 4-year-old ginseng. Malonyl ginsenoside content of main, lateral, and fine root, and of the main root without skin and its skin was compared. Malonyl ginsenosides (m-Rb1, m-Rb2, m-Rc and m-Rd) content (58%, 19.17 mg/g) in total ginsenosides of air dried white ginseng was decreased about 4% compared to its content of freeze dried white ginseng (62%, 20.40 mg/g). Malonyl ginsenoside content was the highest in fine root, compared to the main or lateral root. Malonyl ginsenosides content in skin of main root was 20.08 mg/g, while its content of the main root without skin was 2.58 mg/g. These results are expected to help establishment of quality specification and processing process in Korean white ginseng.

일본의 과학 및 학술 정보 정책의 수립 과정과 실시 체제의 분석

  • 현규섭
    • Journal of the Korean Society for information Management
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    • v.5 no.1
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    • pp.31-52
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    • 1988
  • The information policy in Japan have bccir growing rapldlr 111 recent vttars. \'arioi~s level of govc~riimerital organrzatlons, ir~bt~tution arid agrircics have undt~rtak~~rr iriforrnatiori polrcy 111 order to i r l - crease information flow toward tlie society in Japan. At tlie same trme, computerized library systems also h a w uridergoirc rapid expansion. NACSIS(National Ceriter for- Science Informat~on System) wl~icl~ was cstablisl~ed bv Mirristr> of Etlr~c~arion, Sc~ence arid Culture haw witnessed dramatic adv;rnces i r i promoting for corrstructiori of database so as to provide their 11rf'3r.mat1orr nu nationwide scale. T l r i h articlr inrroduccs tlie actr\rtle> and ~mplcmeritat~o~~ of it format in^^ pol~cy wl~i(~li taktas a place hy goverrirnrlit of Japar~ aid arraly~c,.; thi~ ~ I . O I . P S I of deciiioii maltiiig iri polit~cal procedures. So far as b:ast-A\~ari riatioris art, ~ . n r i v t ~ r ~ ~ , e.;pc,ciall\. Kr,rc.an a~rd Japair !rave ,imilar cultural and liistorical backjir. ourii1, ard could t)t. tliif most a p p r o p r i a t ~ ~ caac stlldh for political ~nq~lerncritat~orr. Thus the topic of this artrclc will be useful to r t ~ a l l ~ t . Ore, trail ur~d c r r o r prorex, iri iiiior.matior~ pnlic\ulcorner.

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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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    • v.21 no.10
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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.

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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    • v.28 no.4
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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.

Quality Control of Ginseng Products(Part I) - The saponins isolated from ginseng roots and leaves - (인삼제품(人蔘製品)의 품질개량(品質改良)에 관(關)한 연구(硏究) (제일보(第一報)) - 인삼근(人蔘根) 및 엽(葉) Saponin의 비교연구(比較硏究) -)

  • Cho, Han-Ok;Cho, Sung-Hwan;Kim, Soo-Ja
    • Applied Biological Chemistry
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    • v.22 no.1
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    • pp.10-17
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    • 1979
  • The saponins isolated form the herb of Panax ginseng C.A. Meyer were investigated as compared with ginseng root saponins. By adopting DEAE cellulose ion exchange chromatography the pure saponins were isolated from Korean ginseng roots and leaves. The ginseng root and leaf saponins showed some differences in the pattern of the two-dimensional thin layer chromatogram. The ratio of panaxadiol to panaxatriol in the saponins was 1.7 in the roots and 3.5 in the leaves. Infra-red spectrum of ginseng leaf saponins isolated by liquid chromatography was identical with that of root saponins.

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An Isolation of Crude Saponin from Red-Ginseng Efflux by Diaion HP-20 Resin Adsorption Method (홍삼유출액으로부터 Diaion HP-20 수지 흡착법에 의한 조사포닌의 분리)

  • 곽이성;경종수;김시관;위재준
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.30 no.1
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    • pp.1-5
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    • 2001
  • This study was carried out to isolate saponin compounds from red-ginseng efflux, which was produced during the industrial processing of red-ginseng from fresh ginseng. We isolated crude saponin from the efflux extract (moisture content 35.0%) by using Diaion HP-20 adsorption method. Non-saponin fraction, which was adsorbed on Diaion HP-20 resin, was removed by eluating with $H_{2}O$ and 25% spirit. Then crude saponin was eluated with 95% spirit, continuously. Saponin in the eluated fractions was confirmed by TLC analysis. Crude saponin isolated from red ginseng efflux extract contained 12.10% of saponin. whereas those of white ginseng and red-ginseng were 3.30 and 3.39%, respectively. Ginsenoside contents showed the highest contents kin crude saponin from red ginseng efflux extract. Expacilly, the ginsenoside-$Rb_{1}$ and Re showed the highest contents in red-ginseng efflux extract when compared with those of white ginseng and red ginseng crude saponins. And the other ginsenosides except ginsenoside-$Rb_{1}$ and -Re also showed the highest contents in red ginseng efflux extract. However, the ratio of PD saponin (Panaxadiol saponin: $Rb_{1}+Rb_{2}$+Rc+Rd) to PT saponin (panaxatriol: $Re+Rg_{1}$) showed almost the same level when compared with those of ginseng saponin fractions. Ratio of PD/PT from red ginseng efflux extract was 1.99. Ratios of PD/PT from white ginseng and red ginseng were 1.85 and 1.84, respectively. Saponin purity, which was calculated by ratio percent of total ginsenoside to curde saponin content, was 45.90%. In case of white ginseng and red ginseng, the purities were 35.50 and 36.00%, respectively. However, by PHLC analysis, we confirmed that crude saponin isolated from red ginsengs. It suggested that crude saponin isolated from red ginseng ellux also would be useful component as ginseng saponins.

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Protective effect of ginsenoside Rb1 against tacrolimus-induced apoptosis in renal proximal tubular LLC-PK1 cells

  • Lee, Dahae;Lee, Dong-Soo;Jung, Kiwon;Hwang, Gwi Seo;Lee, Hye Lim;Yamabe, Noriko;Lee, Hae-Jeong;Eom, Dae-Woon;Kim, Ki Hyun;Kang, Ki Sung
    • Journal of Ginseng Research
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    • v.42 no.1
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    • pp.75-80
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    • 2018
  • Background: The aim of the present study was to evaluate the potential protective effects of six ginsenosides (Rb1, Rb2, Rc, Rd, Rg1, and Rg3) isolated from Panax ginseng against tacrolimus (FK506)-induced apoptosis in renal proximal tubular LLC-PK1 cells. Methods: LLC-PK1 cells were treated with FK506 and ginsenosides, and cell viability was measured. Protein expressions of mitogen-activated protein kinases, caspase-3, and kidney injury molecule-1 (KIM-1) were evaluated by Western blotting analyses. The number of apoptotic cells was measured using an image-based cytometric assay. Results: Reduction in cell viability by $60{\mu}M$ FK506 was ameliorated significantly by cotreatment with ginsenosides Rg1 and Rb1. The phosphorylation of p38, extracellular signal-regulated kinases, and KIM-1, and cleavage of caspase-3, increased markedly in LLC-PK1 cells treated with FK506 and significantly decreased after cotreatment with ginsenoside Rb1. The number of apoptotic cells decreased by 6.0% after cotreatment with ginsenoside Rb1 ($10{\mu}M$ and $50{\mu}M$). Conclusion: The antiapoptotic effects of ginsenoside Rb1 on FK506-induced apoptosis were mediated by the inhibition of mitogen-activated protein kinases and caspase activation.