• Title/Summary/Keyword: 20(R)-ginseng saponin

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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.

Separation of 20(R&S) Prosapogenin Isomers of Ginsenoside-$Rg_2$ and -$Rg_3$ from Ginseng Saponins by Reversed-Phase High Performance Liquid Chromatography (인삼 사포닌에서 Ginsenoside-$Rg_2$와 -$Rg_3$의 이성질체인 20(R&S) Prosapogenin들의 역상 고속 액체 크로마토그래피에 의한 분리)

  • Jeong, Seung-Il;Kim, Cheon-Suk;Lee, Yong-Gu;Lee, Ho-Sup;Kim, Il-Kwang
    • Analytical Science and Technology
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    • v.11 no.5
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    • pp.404-408
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    • 1998
  • Using a reversed-phase high performance liquid chromatography, the separation of 20(S)-, 20(R)-prosapogenin stereo-isomers of ginsenoside-$Rg_2$ and of ginsenoside-$Rg_3$ in ginseng saponins has been carried out with binary solvent system. The optimum conditions for the isomer separation are as following: Nova-$Pak^{(R)}C_{18}$ (Waters, $3.9{\times}150mm$) column, $CH_3CN/CH_3CN$ (100:8, v/v) binary solvent system and the flow rate was 1.7 mL/min. The stereoisomers were separated with change of the mixture ratio of the solvent system, the solvent elution by gradient program, and then detected at 203 nm of UV detector. The simultaneous separation of mixture that were the $Rg_2$, $Rg_3$ isomers was easily performed in nonpolar solvent for $Rg_2$, polar solvent for $Rg_3$ at the same optimum conditions.

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Complete Assignment of $^1H-$ and $^{13}C-NMR$ Signals for (20S)- and (20R)-ginsenoside $Rh_2$ by 2D-NMR Techniques (2D-NMR 기법을 이용한 (20S)-와 (20R)-ginsenoside $Rh_2$$^1H-$$^{13}C-NMR$ Signals의 완전 동정)

  • Kim, Dong-Seon;Lee, You-Hui;Park, Jong-Dae;Jeong, So-Young;Lee, Chun-Bae;Kim, Shin-Il;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.38 no.2
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    • pp.184-189
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    • 1995
  • (20S)- and (20R)-Ginsenoside $Rh_2$ were prepared from crude ginseng saponin by chemical treatments. The $^1H-$ and $^{13}C-NMR$ signals of these compounds were fully assigned by various NMR techniques such as DEPT, $^1H-^1H$ COSY, HMQC, HMBC and NOESY.

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Solubilization of IH-901, a Novel Intestinal Metabolite of Ginseng Saponin, in Aqueous Solution (인삼사포닌의 소장내 최종대사물인 IH-901의 수용액중 가용화)

  • Kwon, Oh-Seung;Chung, Youn-Bok
    • Journal of Pharmaceutical Investigation
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    • v.34 no.5
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    • pp.385-391
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    • 2004
  • The purpose of the present study was to formulate the aqueous solution of $20-O-{\beta}-D-glucopyranosyl-20(S)-protopanaxadiol\;(IH-901)$, an intestinal bacterial metabolic derivative from Ginseng protopanaxadiol saponin. For this purpose, the effects of various solubilization agents such as cosolvents [ethanol, propylene glycol (PG), polyethylene glycol 300 (PEG 300), polyethylene glycol 400 (PEG 400), glycerin], surfactants $(Tween\;80,\;Cremophor^{\circledR}\;RH40,\;Cremophor^{\circledR}\;EL,\;Poloxamer\;407,\;Poloxamer\;188)$ and a complexation agent $[hydroxypropyl-{\beta}-cyclodextrin\;(HPBCD)]$, on the solubility of IH-90l in aqueous solution were evaluated. The solubility of IH-901 in water was under $1\;{\mu}g/ml\;at\;20^{\circ}C$. Cosolvents such as ethanol, PG, PEG 300, PEG 400 and glycerin did not enhance the solubility of IH-901 at the 0 - 40% concentration range. The solubility of IH-901 was significantly elevated by the addition of cosolvents over the 80% concentration range. On the other hand, tween 80, $Cremophor^{\circledR}\;EL,\;Cremophor^{\circledR}\;RH40$ and HPBCD showed enhanced effects on the solubility of IH-901. The enhanced effects of Poloxamer 407 or Poloxamer 188 on the IH-901 solubility were less pronounced compared with $Cremophor^{\circledR}\;EL\;or\;Cremophor^{\circledR}\;RH40$. As a results, $Cremophor^{\circledR}$ aqueous solution was selected as an optimum solvent system. The aqueous solutions containing 10% $Cremophor^{\circledR}\;EL$ and 7% $Cremophor^{\circledR}\;RH40$ were formulated as dosing solutions containing 5.0 mg/ml of IH-901 for its intravenous and oral administration, respectively. The formular showed physical stability after stored for 7 days at $4^{\circ}C$.

Analysis of Ginsenosides of White and Red Ginseng Concentrates (백삼 및 홍삼 농축액의 사포닌 분석)

  • Ko, Sung-Kwon;Lee, Chung-Ryul;Choi, Yong-Eui;Im, Byung-Ok;Sung, Jong-Hwan;Yoon, Kwang-Ro
    • Korean Journal of Food Science and Technology
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    • v.35 no.3
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    • pp.536-539
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    • 2003
  • Commercial white and red ginseng concentrates were analysed for total ginsenoside contents, and compositions of ginsenosides $Rb_1,\;Rb_2,\;Rc,\;Re,\;Rf,\;Rg_1,\;20(S)\;Rg_3,\;20(S)\;Rh_1,\;and\;20(R)\;Rh_1$. The content of crude saponin and total ginsenosides of white ginseng concentrates (WGC) were about 2-3 times higher than those of red ginseng concentrates (RGC). HPLC showed that each ginsenoside content was higher in WGC, with those of $Rb_1,\;Rg_1,\;and\;Rb_2$ being over three times higher than that of RGC. 20(S)- and 20(R)-ginsenoside $Rg_3$, specific artifacts found only in red ginseng, were detected both in WGC and RGC by HPLC. differences in the contents of these specific ginsenosides between WGC and RGC were not significant. The contents of 20(S)-ginsenoside $Rg_1$, determined by HPLC were 0.40 and 0.53 in WGC, whereas 0.48% and 0.47%, and those of 20(R)-ginsenoside $Rg_3$, were 0.14 and 0.22% in WGC, and 0.10 and 0.11% in RGC using the methods of shibata and food Code, respectively.

Monitoring of Chemical Changes in Explosively Puffed Ginsengvand the Optimization of Puffing Conditions

  • Yoon, Sung-Ran;Lee, Gee-Dong;Kim, Hyun-Ku;Kwon, Joong-Ho
    • Journal of Ginseng Research
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    • v.34 no.1
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    • pp.59-67
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    • 2010
  • Response surface methodology was used to predict the optimum conditions of explosive puffing process for ginseng. A central composite design was used to monitor the effect of moisture content and puffing pressure on dependent variables such as functional compounds (extract yield, crude saponin, acidic polysaccharide, and total phenolic content) and sensory properties. Correlation coefficients $(R^2)$ of models for crude saponin, acidic polysaccharide, and total phenolic content were 0.9176 (p<0.05), 0.9494 (p<0.05), and 0.9878 (p<0.001), respectively. Functional compounds increased with decreasing moisture content and increasing puffing pressure. Overall palatability was high at 15-20% moisture content and 98-294 kPa of puffing pressure. On the basis of superimposed contour maps for functional compounds and overall palatability of puffed ginseng, the optimum ranges of puffing conditions were 10-17% moisture content and 294-392 kPa puffing pressure.

Effect of Blue and Red LED irradiation on Growth Characteristics and Saponin Contents in Panax Ginseng C. A. Meyer (청색과 적색 LED 처리가 인삼의 생육 및 사포닌 함량에 미치는 영향)

  • Kim, Min-Jeong;Li, Xiangguo;Han, Jin-Soo;Lee, Seong-Eun;Choi, Jae-Eul
    • Korean Journal of Medicinal Crop Science
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    • v.17 no.3
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    • pp.187-191
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    • 2009
  • This study was conducted to assess the response of LED (Light-emitting diode) irradiation on the growth characteristics and saponin contents of Panax ginseng C. A. Meyer. LED irradiation showed a positive effect for most of the parameters studied. The content of chlorophyll a in leaves was increased by 4.9$\sim$36.5%, under LED and fluorescent light conditions compared to the control. The content of chlorophyll b was also increased by 44.4$\sim$55.6% under blue and red LED compared to the control except under the red plus blue LED condition. The shoot and root weight were increased by $20\sim60%$ and $14.8\sim59.3%$, respectively under LED and fluorescent light conditions compared to the control. The total saponin content was increased by 1.8% under blue LED compared to the control, while total saponin content was decreased by 8.8$\sim$11.5% under red LED, red plus blue LED and fluorescent light conditions.

Effect of Ginseng Saponin on Hypothalamus-Pituitary- Adrenal Axis under Stress in Mice

  • Do Hoon Kim;Jun
    • Proceedings of the Ginseng society Conference
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    • 1998.06a
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    • pp.83-89
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    • 1998
  • Ginseng total saponins (GTS) injected intracerebroventricularly (i.c.v.) at doses from 0.1-1 vs inhibited the i.c.v. injection stress-induced plasma corticosterone levels in mice. The inhibitory action of GTS was blocked by co-administered NG-nitro-L-arginine methyl ester (L-NAME; 1.5 us, i.c.v.), an. inhibitor of nitric oxide synthase (NOS). Of the ginsenosides Rbl, Rba, Rc, Rd, Re, Rf, Rgl,20(S)-Rg3, and 20(R)-Rg3 injected i.c.v. at doses from 0.01 to 0.3ug(or 1 uE),20(5)-Rg3 and Rc significantly inhibited the o.c.v. injection stress-induced Plasma corticosterone levels. The inhibitory actions of 20(S)-Rg3 and Rc were blocked by co-administered L-NAME (1.5 n, i.c.v.). These results suggest that G75, 20(S)-Rg3 and Rc may inhibit the i.c.v. injection stress-induced hypothalamo-pituitary-adrenal response by inducing NO production in the brain.

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The Changes of Physicochemical Characteristics and Quality Stability of Korean Red Ginseng (Panax ginseng C.A. Meyer) Stored over 20 Years (20년 이상 장기저장된 홍삼의 이화학적 특성변화 및 품질안정성)

  • Kwak, Yi-Seong;Han, Min Woo;Bae, Bong-Seok;Ahn, Nam-Geun;Yu, Hye Young;Park, Chol-Soo;Baeg, In-Ho;Cho, Byung-Gu
    • Korean Journal of Pharmacognosy
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    • v.48 no.4
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    • pp.329-338
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    • 2017
  • This study was investigated the changes of quality stability and physicochemical characteristics of the Korean red ginsengs stored for a long times over 20 years. The Korean red ginsengs were stored for 4 to 22 years in canned packaging with polypropylene film and wooden box at room temperatures. The unusal phenomena such as discoloration and pin hole in packaging were not observed. General bacteria showed the vlaues of below 100 CFU/g, coliform groups and molds were not found in any samples stored for 22 year. Any samples also were not detected in mycotoxins. The contents of moisture, ash and crude saponin were the levels of 10.6~11.1%, 3.8~4.2% and 4.1~4.7% during the whole storage periods, respectively. The contents of maltol, which has been known as characteristic flavour and antioxidant of Korean red ginseng, showed remarkably increasing tendency from 0.10 mg/g for 4 years to 2.53 mg/g for 22 years during the storage. The contents of AFG (arginyl-fructosyl-glucose), arginine and free sugar were slightly decreased. Acidic polysaccharide and ginsenoside were not changed significantly during the storage periods. The contents of acidic polysaccharide and total ginsenosides were the 75.1~76.3 mg/g and 15.1~16.6 mg/g, respectively. The sums of ginsenoside-Rg1,-Rb1 and -Rg3s were the ranges of 9.3~9.9 mg/g and PD (ginsenoside-Rb1, -Rb2,-Rc,-Rd,-Rg3s,-Rg3r)/PT (ginsenoside-Rg1,-Rg2,-Re,-Rf,-Rh1) saponin ratios were the levels of 1.4~1.5. These results suggest that Korean red ginsengs stored for long periods show relatively stable quaility stabilities and not significantly changed the contents of ginsenoside and polysaccharide during the storage up to 22 years.

Seven New Ginsenosides From a New Processed Ginseng

  • Park, Jeong-Hill;Kim, Jong-Moon;Han, Sang-Beom;Kim, Na-Young;Lee, Seung-Ki;Kim, Nak-Doo;Park, Man-Ki;Han, Byung-Hoon
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1998.11a
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    • pp.175-175
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    • 1998
  • We reported a new processed ginseng with increased biological activities which is named as “sun ginseng (SG)”. Study on the saponin constituents of SG led to the isolation of seven new ginsenosides named as ginsenoside Rk$_1$, Rk$_2$, Rk$_3$, Rs$_4$, Rs$\_$5/, Rs$\_$6/ and Rs$\_$7/. Ginsenoside Rk$_1$, Rk$_2$ and Rk$_3$ were the Δ$\^$20(21),24(25)/-diene dammarane compounds, while ginsenoside Rs$_4$, Rs$\_$5/, Rs$\_$6/ and Rs$\_$7/ were mono-acetylated compounds. Many other ginsenosides which were reported as minor constituents of red ginseng were also isolated, which include 20(S)-Rg$_3$, 20(R)-Rg$_3$, Rg$\_$5/, Rg$\_$6/, F$_4$, Rh$_4$, 20(S)-Rs$_3$ and 20(R)-Rs$_3$. The major ginsenosides of SG were 20(S)-Rg$_3$, 20(R)-Rg$_3$, Rk$_1$ and Rg$\_$5/.

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