• 제목/요약/키워드: 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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    • 제25권4호
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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.

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

  • Kim, Yu.A.;Park, Kyeong-Mee;Park, Hwa-Jin
    • Journal of Ginseng Research
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    • 제20권1호
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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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    • 제20권2호
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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.

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

  • 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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    • 제20권3호
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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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인삼 사포닌의 체내 대사에 관한 연구(I) 동위원소 표지 사포닌의 흡수, 체내 분포 및 배설에 관하여 (Metabolisrrt of Dammarane Triterpene Glycosides of Korean Ginseng(I))

  • 한병훈;장일무
    • Journal of Ginseng Research
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    • 제2권1호
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    • pp.17-33
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    • 1977
  • 1. 인삼증에 함유된 danlmarane계 glycoside 성분들 중의 한 성분인 panax saponin A(ginsenoside Rgl)(약자 : PSA)에 $^{14}C$ 또는 $^{3}H$를 도입한 방사능 표지 사포닌을 합성하였다. 2. $^{3}H$-PSA의 방사능을 생체내 에서 추적한 결과 PSA는 위장관내에서 쉽게 흡수되어 생체 내 전장기에 골고루 분포된다. 3. 각 장기에 분포된 PSA는 세포 내에 섭취되며 세포 내에 섭취 되는 양은 일정한 포화점이 있다. 4. 포화점을 초과하여 섭취된 PSA는 즉시 뇨를 통하여 배설되며 섭취된 PSA는 세포 내에 장기간 잔유한다.

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

  • 우린근;한병훈;박대성;나운용
    • 생약학회지
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    • 제4권4호
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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
    • 약학회지
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    • 제21권3호
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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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Seven new dammarane glycosides from heat processed ginseng

  • Kwon, Sung-Won;Kim, Na-Young;Park, Il-Ho;Han, Sang-Beom;Kim, Jong-Moon;Park, Jeong-Hill;Park, Man-Ki
    • 대한약학회:학술대회논문집
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    • 대한약학회 2000년도 NEW STRATEGY FOR DRUG DEVELOPMENT IN POST-GENOMIC ERA(대한약학회)
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    • pp.254.3-255
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    • 2000
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SYNTHESIS OF THE GINSENG GLYCOSIDES AND THEIR ANALOGS

  • Elyakov G. B.;Atopkina L. N.;Uvarova N. I.
    • 고려인삼학회:학술대회논문집
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    • 고려인삼학회 1993년도 학술대회지
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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
    • 한국응용약물학회:학술대회논문집
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    • 한국응용약물학회 1998년도 Proceedings of UNESCO-internetwork Cooperative Regional Seminar and Workshop on Bioassay Guided Isolation of Bioactive Substances from Natural Products and Microbial Products
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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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