Malonyl-ginsenosides Rb1,Rb2,Rc, and Rd, four new malonylated dammarane-type triterpene oligoglycosides from ginseng radix.

Kitagawa, Isao; Taniyama, Tadayoshi; Hayashi, Teruaki; Yoshikawa, Masayuki

doi:10.1248/cpb.31.3353

Cited by 51 publications

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“…This finding suggests that the structures of aglycon can be recognized from the band color, and the Rf value is reflected by the sugar number. Using this result, we determined two bands under G-Rb1 as MG-Rb1 (Kitagawa et al, 1983) and 20-O-gentiobiosyl-chikusetsusaponin III (Shoji, 1990), which has five sugars in a molecule of P. ginseng, in good agreement with the Rf value previously reported (Kitagawa et al, 1983;Shoji, 1990). Finally, these two compounds were identified by comparing with authentic samples (data not shown).…”

Section: G-rb1 and -Rg1 Concentrations In Panax Spp Measured By Elisasupporting

confidence: 85%

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Quality Control of Panax Species by Monoclonal Antibody and DNA Analysis

Tanaka¹

2011

Quality Control of Herbal Medicines and Related Areas

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Section: G-rb1 and -Rg1 Concentrations In Panax Spp Measured By Elisasupporting

confidence: 85%

“…Kitagawa et al isolated malonyl ginsenosides from white ginseng, finding that non-processed ginseng contents are higher than in processed ginseng (Kitagawa et al, 1983). It is thought that MG-Rb1 influences ELISA since it is suggested that MG-Rb1 has similar cross-reactivity with G-Rb1.…”

Section: G-rb1 and -Rg1 Concentrations In Panax Spp Measured By Elisamentioning

confidence: 99%

Quality Control of Panax Species by Monoclonal Antibody and DNA Analysis

Tanaka¹

2011

Quality Control of Herbal Medicines and Related Areas

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“…The chemical structures of the individual ginsenosides have been identified. [6][7][8][9][10][11][12] Based on the ginsenoside aglycone, the ginsenosides can be classified into three groups: the protopanaxadiol-type; protopanaxatriol-type; and oleanolic acidtype saponins. …”

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confidence: 99%

Purification and Characterization of Ginsenoside-.BETA.-Glucosidase from Ginseng.

Zhang

Bao

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Ginseng, the root of Panax ginseng C. A. MEYER, is a medicinal plant used worldwide and has been reported to have various biological effects.1-3) Ginsenosides isolated from ginseng are the main pharmacoactive molecules of ginseng.4) They exhibit efficacy as anticancer, antistress, antihypertention, antidiabetes, and antinociception agents, and facilitate learning and improve weakness as tonics.5) More than 34 ginsenosides, triterpene-derivatives containing sugars, have been isolated from the ginseng saponin fraction. The chemical structures of the individual ginsenosides have been identified. [6][7][8][9][10][11][12] Based on the ginsenoside aglycone, the ginsenosides can be classified into three groups: the protopanaxadiol-type; protopanaxatriol-type; and oleanolic acidtype saponins. 13)Recently, ginsenoside Rh2, a rare saponin contained in wild ginseng and red ginseng, has attracted attention because of its high inhibition of cancer cell growth.14) The ginsenoside Rh2 inhibited the growth of B16 melanoma cells, 15,16) and inhibited the tumor growth of human ovarian cancer cells inoculated into nude mice to the same extent as cis-diamminedichloroplatinum. 17,18) However, it is very difficult to obtain the ginsenoside Rh2 from wild and red ginseng, because its content is low. We reported that ginsenoside Rh2 was obtained from ginsenoside-b-glucosidase from the newly isolated microorganism FFCDL-48 strain by hydrolyzing the other protopanaxadiol saponins such as ginsenoside Rg3 into ginsenoside Rh2,19) as shown in Fig. 1. In this study, the ginsenoside-b-glucosidase in the ginseng plant which hydrolyzes the b-(1→ 2)-glucoside bond of ginsenosides was isolated, purified, and characterized. ExperimentalMaterials The ginseng root used was 4-year-old ginseng from the No. 1 Ginseng Plant of Fusong, Jilin Province, China. The standard 20(S)-ginsenoside Rg3, 20(S)-ginsenoside Rh2, and other ginsenosides were obtained from the Academy of Science of D.P.R. Korea. The thin-layer chromatography (TLC) plate was a silica gel plate Merck).Enzyme Extraction from Ginseng The fresh ginseng was broken into pieces and added to a 3-fold volume of 20 mM acetate buffer, pH 5.0. It was extracted at 40°C for 2 h and the supernatant was obtained by centrifugation for use in saponin enzyme purification.Purification of Ginsenoside-b b-Glucosidase and Estimation of Molecular Weight Pellets of (NH 4 ) 2 SO 4 were slowly added to the supernatant extracted from fresh ginseng with shaking to 70% saturation and stored at 4°C overnight. The mixture was centrifuged to collect the protein precipitate. This crude protein was dissolved in distilled water and dialyzed against 20 mM acetate buffer, pH 5.0. After removing the nondissolved fraction by centrifugation, the enzyme solution was fractionated on a column (f1.5ϫ 10 cm) of DEAE-cellulose DE-52 (Whatman). The column was eluted stepwise with 60, 120, 180, and 240 mM KCl in 20 mM Tris-HCl buffer, pH 7.4. The purified enzyme was dried by freeze-drying and used for the study of enzyme properties. Th...

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“…More than 30 ginsenosides, which are triterpene derivatives that contain sugars, have been isolated from the ginseng saponin fraction. The chemical structures of the individual ginsenosides have been identified (Shibata et al, 1963(Shibata et al, , 1965Nagai et al, 1971;Kaku and Kawashima, 1980;Kitagawa et al, 1983;Shao, 1984;Baek et al, 1996). It was reported that ginsenosides Rb and Rc exhibited a sedative effect, whereas ginsenoside Rg showed stimulatory actions on the CNS (Takagi et al, 1972b;Saito et al, 1974).…”

Section: Introductionmentioning

confidence: 99%

Ginsenosides Rb1and Rg3protect cultured rat cortical cells from glutamate-induced neurodegeneration

et al. 1998

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Certain natural products and Asian herbal remedies have been used in Asia to attenuate neurodegenerative diseases, including senile dementia. We have examined derivatives of several natural products for potential neuroprotective activity in an in vitro test system. In the present study, we assayed a number of compounds that were isolated from Panax ginseng C.A. Meyer (Araliaceae) for an ability to protect rat cortical cell cultures from the deleterious effects of the neurotoxicant, glutamate. We found that ginsenosides Rb1 and Rg3 significantly attenuated glutamate-induced neurotoxicity. Brief exposure of cultures to excess glutamate caused extensive neuronal death. Glutamate-induced neuronal cell damage was reduced significantly by pretreatment with Rb1 and Rg3. Ginsenosides Rb1 and Rg3 inhibited the overproduction of nitric oxide, which routinely follows glutamate neurotoxicity, and preserved the level of superoxide dismutase in glutamate-treated cells. Furthermore, in cultures treated with glutamate, these ginsenosides inhibited the formation of malondialdehyde, a compound that is produced during lipid peroxidation, and diminished the influx of calcium. These results show that ginsenosides Rb1 and Rg3 exerted significant neuroprotective effects on cultured cortical cells. Therefore, these compounds may be efficacious in protecting neurons from oxidative damage that is produced by exposure to excess glutamate.

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Malonyl-ginsenosides Rb1,Rb2,Rc, and Rd, four new malonylated dammarane-type triterpene oligoglycosides from ginseng radix.

Cited by 51 publications

References 0 publications

Quality Control of Panax Species by Monoclonal Antibody and DNA Analysis

Quality Control of Panax Species by Monoclonal Antibody and DNA Analysis

Purification and Characterization of Ginsenoside-.BETA.-Glucosidase from Ginseng.

Ginsenosides Rb1and Rg3protect cultured rat cortical cells from glutamate-induced neurodegeneration

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