• Title/Summary/Keyword: dammarane glycosides

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Three New Dammarane Glycosides from Heat Processed Ginseng

  • Park, Il-Ho;Kim, Na-Young;Han, Sang-Beom;Kim, Jong-Moon;Kwon, Sung-Won;Kim, Hyun-Jung;Park, Man-Ki;Park, Jeong-Hill
    • Archives of Pharmacal Research
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    • v.25 no.4
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    • pp.428-432
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    • 2002
  • Three new dammarane glycosides were isolated from the processed ginseng (SG; Sun Ginseng). Their structure were determined to be $3{\beta},{\;}12{\beta}-dihydroxydammar-20(21),24-diene-3-O-{\beta}-D-glucopyranosyl(1{\;}{\rightarrow}{\;}2)-{\beta}-D-glucopyranoside;{\;}3{\beta},{\;}12{\beta}-dihydroxydammar-20(21),24-diene-3-O-{\beta}-D-{\;}glucopyranoside{\;}and{\;}3{\beta},6{\alpha},12{\beta}-trihydroxydammar-20(21),24-diene-6-O-{\beta}-D-glucopyranoside$ based on spectroscopic evidences. The compounds were named as ginsenoside $Rk_1,{\;}Rk_2,{\;}and{\;}Rk_3$ respectively.

Effect of Triterpenoidal Glycosides of Dammarane Series and Their Aglycones on Phase Transitions of Dipalmitoylphosphatidylcholine (DPPC의 상전이에 미치는 Dammarane Series의 Triterpenoidal Glycoside와 그 Aglycone의 영향)

  • Kim, Yu.A.;Park, Kyeong-Mee;Park, Hwa-Jin
    • Journal of Ginseng Research
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    • v.20 no.1
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    • pp.23-29
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    • 1996
  • The effect of ginseng glycosides and their aglycones on the thermodynamic characteristics of membranes from dipalmitoylphosphatidylcholine (DPPC) was investigated. Total saponins (TS) from Korean red ginseng, Panax ginseng C.A. Meyer, interacted with the Eel Phase of lipid in the Polar region and did not penetrate the deeper glycerol backbone of lipid molecule. From the all investigated components of TS (aglycons and ginsenosides), only 20-(S)-panaxadiol (PD) had an effect similar to TS. High concentration of TS penetrated in hydrophobic Cl-C8 region. The presence of cholesterol did not influence the interaction of TS with DPPC. An elimination of transition, however, took place at 10~100 $\mu\textrm{g}$/ml of TS. DPPC had a low ability to interact with cholesterol (CHL) as compared with other lecithins except ethanolamine. From our results, only TS and PD, at high concentrations (100 mol%), influenced the phase transition of mixture of DPPC:CHL.

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Thermal Conversion Pathways of Ginsenosides in Red Ginseng Processing

  • Lee, Sang Myung
    • Natural Product Sciences
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    • v.20 no.2
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    • pp.119-125
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    • 2014
  • According to the results of my study on the chromatographic analysis of fresh ginseng (Panax ginseng C. A. Meyer) roots, most of the contents of protopanxadiol ginsenosides $Rb_1$, Rc, $Rb_2$, and Rd are derived from the corresponding malonyl ginsenosides in fresh ginseng by a heat process. Also, I confirmed that acetyl ginsenosides are naturally occurring constituents in fresh ginseng, not decarboxylates from malonyl ginsenosides. Seven neutral ginsenosides $Rg_1$, Re, Rf, Rc, $Rb_1$, $Rb_2$, and Rd were transformed to specific conversions in red ginseng preparation conditions. The conversion paths progress by three rules concluded from my study. These conversion rules are I: the ether bond is stable at positions 3 and 6 in the dammarane skeleton, II: the ether bond between sugars is stable in glycosides, and III: the ether bond to glycosides is unstable at position 20 in the dammarane skeleton.

Action of Dammarane-Type Triterpenoidal Glycosides and Their Aglycones on Lipid Membranes (지질막에 대한 Dammarane-Type Triterpenoidal Glycosides와 그 Aglycones의 작용)

  • Kim, Yu.A.;Park, Kyeong-Mee;Hyun, Hack-Chul;Song, Yong-Bum;Shin, Han-Jae;Park, Hwa-Jin
    • Journal of Ginseng Research
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    • v.20 no.3
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    • pp.269-273
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    • 1996
  • We investigated the effects of ginseng glycosides and their aglycones on processes of single ion channel formation and channel properties. The glycosides, Rg, and Rb, , and their aglycones, 20-(S)-protopanaxatriol (PT) and 20-(S)-protopanaxadiol (PD) increased the membrane permeability for ions. PT, PD, Rg1, and Rb1; at concentrations of 0.5, 3.0, 10.0 and 30.0 $\mu\textrm{g}$/ml respectively; Induced single ion channel fluctuations with the life times in the range of 0.1~1005 in open states and conductances from 5 to 30 pS in 1 M KCI. At high concentrations of these substances, rapid fluctuations of transmembrane ion current with amplitude from hundred pS to dozen nS were observed. Against other substances, ginsenoside Rbl began to increase the membrane conductance at concentration of about 60 $\mu\textrm{g}$/ml without fluctuation of single ion channel. Membranes treated with PT, PD, Rg1 and Rb1 are more permeable to K+, than to Cl while zero current membrane potentials with 10 gradients of KCI were 12, 16, 8, 25 mV respectively. Key words : Membrane conductance, single ion channel, ginsenosides.

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Metabolisrrt of Dammarane Triterpene Glycosides of Korean Ginseng(I) (인삼 사포닌의 체내 대사에 관한 연구(I) 동위원소 표지 사포닌의 흡수, 체내 분포 및 배설에 관하여)

  • 한병훈;장일무
    • Journal of Ginseng Research
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    • v.2 no.1
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    • pp.17-33
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    • 1977
  • Panax Saponin A(PSA) , one of dammarane glycosides of Korean ginseng, was labeled with $^{3}H$ or $^{14}C$ by our Previously reported Procedures of organic synthesis. Tracer studies with $^{3}H$-PSA in wino yielded the following results: 1). Oral and intraperitoneal administration of $^{3}H$-PSA resulted in the rapid appearance and prolonged retention of $^{3}H$-PSA in all organs such as liver, brain, bone marrow and spleen of mice. 2). The amount pi cellular intake of $^{3}H$-PSA was shown to have a certain level of saturation ranging from 0.4mg to 0. 7mg Per 20gm body weight of mice. Administration of $^{3}H$-PSA within the dosage of the saturation point did net give urinary excretion of 3H-PSA. On the contrary, excessive administration of $^{3}H$-PSA resulted in rapid excretion of the substance in the urine of mice.

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Species Differences of Dammarane Aglycones of Ginsengs (한국산(韓國産) 및 외국산(外國産) 인삼(人蔘)의 성분(成分) 비교(比較))

  • Woo, Lin-Keun;Han, Byung-Hoon;Park, Dae-Sung;Lah, Woon-Lyong
    • Korean Journal of Pharmacognosy
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    • v.4 no.4
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    • pp.181-184
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    • 1973
  • In the light of quality comparison the ratio of panaxadiol and panaxatriol contents was assayed in the extract of various ginseng products, whose origin of production and species of the original plants are different. Aglycone compositions of other ginsengs were not comparable with Korean ginseng in their ratio of panaxadiol and panaxatriol contents of dammarane glycosides.

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Studies on the Analysis of Dammarane Aglycones of Korean Ginseng

  • Lee, Wang-Kyu;Kim, Byong-Kak;Kim, Hai-Jung
    • YAKHAK HOEJI
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    • v.21 no.3
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    • pp.163-166
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    • 1977
  • To establish a convenient quantitative method for dammarane glycosides in Korea ginseng, the ginseng roots harvested at the cultivation areas of Ga Pyeong, Geum San and Jeung Pyeong were dried, powered, extracted with methanol and hydrolyzed. The ginseng root obtained at Gang Hwa was divided into three parts: main root, laterial root and cortex, and then these were treated in the same manner as the above. The various hydrolysates thus obtained were subjected to the analysis by an instrument coupled with flame ionization detector. The results showed that panaxadiol contents in the ginsengs of the three different cultivation sites were similar. However, the lateral root of Gang Hwa ginseng was found to contain the largest amount of panaxadiol among the three parts of ginseng. This method of the analysis for panaxadiol in ginseng was found to be one with relative rapidity and ease.

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SYNTHESIS OF THE GINSENG GLYCOSIDES AND THEIR ANALOGS

  • Elyakov G. B.;Atopkina L. N.;Uvarova N. I.
    • Proceedings of the Ginseng society Conference
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    • 1993.09a
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    • pp.74-83
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    • 1993
  • In an attempt toward the synthesis of the difficulty accessible ginseng saponins the four dammarane glycosides identical to the natural $ginsenosides-Rh_2,$ - F2, compound K and chikusetsusaponin - LT8 have been prepared from betulafolienetriol(=dammar-24-ene-$3{\alpha},12{\beta}\;20(S)-triol).\;3-O-{\beta}-D-Glucopyranoside$ of 20(S) - protopanaxadiol $(=ginsenoside-Rh_2)$ have been obtained by the regio - and stereoselective glycosylation of the $12-O-acetyldammar-24-ene-3{\beta},\;12{\beta},$ 20(S)-triol. The 12-ketoderivative of 20(S)-protopanaxadiol has been used as aglycon in synthesis of chikusetsusaponin - LT8. Attempted regio - and stereoselective glycosylation of the less reactive tertiary C - 20 - hydroxyl group in order to synthesize the $20-O-{\beta}-D-glucopyranoside$ of 20(S)-protopanaxadiol(=compound K) using 3, 12 - di - O - acetyldammar - 24 - ene - $3{\beta},12{\beta},20(S)$-trial as aglycon was unsuccessful. Glycosylation of 3, 12 - diketone of betulafolienetriol followed by $NaBH_4$ reduction yielded the $20-O-{\beta}-D-glucopyranoside\;of\;dammar-24-ene-3{\beta},12{\alpha},$ 20(S)-triol, the $12{\alpha}-epimer$ of 20(S) - protopanaxadiol. Moreover, a number of semisynthetic ocotillol - type glucosides, analogs of natural pseudoginsenosides, have been prepared.

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In vivo Anti-metastatic Action of Ginseng Protopanaxadiol saponins is Based on Their Intestinal Bacterial Metabolites After Oral Administration

  • Saiki, Ikuo
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1998.11a
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    • pp.95-98
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    • 1998
  • Ginseng (the root of Panax ginseng C. A. MEYER, Araliaceae) has been used for traditional medicine in China, Korea, Japan and other Asian countries for the treatment of various diseases including psychiatric and neurologic diseases as well as diabetes mellitus. So far, ginseng saponins (ginsenosides) have been regarded as the principal components responsible for the pharmacological activities of ginseng. Ginsenosides are glycosides containing an aglycone (protopanaxadiol or protopanaxatriol) with a dammarane skeleton and have been shown to possess various biological activities including the enhancement of cholesterol biosynthesis, stimulation of serum protein synthesis, immuno- modulatory effects and anti-inflammatory activity. Several studies using ginsenosides have also reported anti-tumor effects, particularly the inhibition of tumor-induced angiogenesis, tumor invasion and metastasis, and the control of phenotypic expression and differentiation of tumor cells.

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