Ginsenoside Rg5, a genuine dammarane glycoside from Korean red ginseng

Kim, Shin Il; Park, Jeong Hill; Ryu, Jae‐Ha; Park, Jong Dae; Lee, You Hui; Park, Jae-Hyun; Kim, Tae-Hee; Kim, Jong Moon; Baek, Nam‐In

doi:10.1007/bf02986026

Cited by 59 publications

(30 citation statements)

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“…The residue was chromatographed on silica gel column, using CHCl3-MeOH-H2O (9:3:1) as solvent, to obtain ginsenoside Rg3 and Rg5 mixture. Ginsenoside Rg3 and Rg5 mixtures were subjected to HPLC (Waters 244, CLC-ODS, RI dectector), using acetonitril-water (60:40) as mobile phase, to analyze the ratio of ginsenoside Rg3 to Rg5 (2.6 g) (45,50).…”

Section: Anticarcinogenicity Of Various Ginseng Fractionsmentioning

confidence: 99%

Anticarcinogenic Effect of Panax ginseng C.A. Meyer and Identification of Active Compounds

Yun¹,

Lee²,

Lee³

et al. 2001

J Korean Med Sci

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206

138

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The failure to improve the five-year survival rate of cancer patients, from one in three in the 1960s to one in two in the 1970s, stimulated awareness of the importance of primary prevention of cancer. Korean investigators carried out extensive long-term anticarcinogenicity experiments with 2000 newborn mice to investigate whether Panax ginseng C.A. Meyer inhibited carcinogenesis induced by several chemical carcinogens in 1978. There was a 22% decrease (p <0.05) in the incidence of urethane induced lung adenoma by the combined use of red ginseng extract. In the group sacrificed at 56 weeks after the treatment with aflatoxin B1, the incidence of hepatoma significantly decreased to 75% by the addition of red ginseng extract (p <0.05). The result showed that natural products can provide hope for human cancer prevention. By the newly established '9 week mediumterm anticarcinogenicity test model of lung tumors in mice' (Yun' s model), we confirmed significant anticarcinogenic effects of powders and extracts of the 6-yr-old dried fresh ginseng, 5-and 6-yr old white ginsengs, and 4-, 5-, and 6-yr old red ginseng. We also demonstrated that the anticarcinogencity of ginseng was more prominent in aged or heat treated extracts of ginseng and red ginseng made by steaming. To investigate the active components for cancer prevention, several fractions of 6-yr old fresh ginseng and red ginseng, four semi-synthetic ginsenoside Rh1, Rh2, Rg3 and Rg5, major saponin components in red ginseng, were prepared. Among the ginsenosides, Rg3 and Rg5 showed statistically significant reduction of lung tumor incidence and Rh2 had a tendency of decreasing the incidence. Ginsenoside Rg3, Rg5 and Rh2 were found to be active anticarcinogenic compounds. Rg3, Rg5 and Rh2 are active components in red ginseng, and they prevent cancer either singularly or synergistically.

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Section: Anticarcinogenicity Of Various Ginseng Fractionsmentioning

confidence: 99%

Anticarcinogenic Effect of Panax ginseng C.A. Meyer and Identification of Active Compounds

Yun¹,

Lee²,

Lee³

et al. 2001

J Korean Med Sci

Self Cite

206

138

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“…A long-range correlation was observed between the anomeric proton signal at d 5.05 and the C-6 signal at d 80.1. Furthermore, the 13 C-NMR signals of 1 were found to be superimposable on those of ginsenosideRh 1 (8) except for the signals due to the side-chain part (C-22-C-27) of the aglycone which showed a signal of a terminal double bond at d 149.9 and 110.0, and two olefinic carbon signals at d 142.4 and 122.2. The structure of the sidechain part of the sapogenol moiety was elucidated by 13 Ginsenoside-Rh 6 (2) was isolated as a white powder.…”

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confidence: 93%

“…The stereochemistry of the double bond at C-20 (22) was proposed to be (E) since the signal for C-21 was observed at d 13.2 in the 13 C-NMR spectrum of 1, while the methyl carbon of a (Z)-type structure is usually observed at about d 20-30. 7,8) From the above results, the structure of 1 was determined as 3b,6a,12b,24x-tetrahydroxy-dammar-20 (22) …”

mentioning

confidence: 99%

“…The total saponins were chromatographed on silica gel, a reversed-phase column and finally on HPLC to afford ginsenoside-Rh 5 (1, 8 mg), -Rh 6 (2, 9 mg), -Rh 7 (3, 10 mg), -Rh 8 (4, 5 mg), -Rh 9 (5, 9 mg), -Rg 7 (6, 10 mg), majoroside-F 2 (7, 9 mg), ginsenoside-Rh 1 (8, 100 mg), chikusetsusaponin-L 8 3) (9, 15 mg), notoginsenoside-Fe 4) (10, 10 mg), majoroside- allow only one molecule of glucose to be linked to the aglycone. On acid hydrolysis, it yielded a glucose which was identified by TLC comparison with authentic sample, suggesting 1 was a glycoside.…”

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confidence: 99%

“…Compound 6 was therefore deduced to be the corresponding 24(R) counterpart of 7 and was formulated as 3-O-b-D-glucopyranosyl 3b,12b,20(S),24(R)-tetrahydroxy-dammar-25-ene 20-O-b-D-glucopyranoside, which is a new compound and named as ginsenoside-Rg 7 . The 14 known saponins (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) were identified by comparison of their spectral data with literature values.…”

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Six New Dammarane-type Triterpene Saponins from the Leaves of Panax ginseng

et al. 2001

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Panax ginseng, an ancient and famous herbal drug in traditional chinese medicines, has been used in Chinese folklore for more than 4000 years. In the course of our studies to find bioactive saponins from natural medicines, a number of dammarane-type triterpene oligoglycosides having anti-cancer, anti-arrhythmia and inhibitory effects on reducing sideeffects of steroid hormones were found.1,2) In a continuing study, further systematic research on chemical constituents from the leaves of P. ginseng, we now report the isolation and structural elucidation of six new saponins, together with 14 known ones among which, majoroside-F 2 was the first isolated from P. ginseng.The 70% EtOH extract from the dried leaves of P. ginseng were separated by a macro-reticular resin column to give the 50% EtOH eluates which upon drying afforded the total saponins. The total saponins were chromatographed on silica gel, a reversed-phase column and finally on HPLC to afford ginsenoside-Rh 5 (1, 8 mg), -Rh 6 (2, 9 mg), -Rh 7 (3, 10 mg), -Rh 8 (4, 5 mg), -Rh 9 (5, 9 mg), -Rg 7 (6, 10 mg), majoroside-F 2 (7, 9 mg), ginsenoside-Rh 1 (8, 100 mg), chikusetsusaponin-L 8 3) (9, 15 mg), notoginsenoside-Fe 4) (10, 10 mg), majoroside- H COSY and HMBC experiments of 1. In the HMBC spectrum, a methyl proton signal at d 1.83 showed long-range correlations between d 51.0 (C-17), d 142.4, and 122.2. So this methyl signal can be assigned to the proton of C-21, and the two olefinic carbon signals can be assigned for C-20 and C-22, respectively. Similarly, the HMBC spectrum also revealed long-range correlations between the following protons and carbons: H-23 and C-20, 22, 24; H-27 and C-24, 25, 26 (Fig. 1). In addition, in the 1 H-1 H COSY spectrum, the signals at d 2.41, 2.55 (H-23) showed a correlation with each other, and the correlations between H-23 with d 5.69 (t like, Jϭ7.5 Hz, H-22) and d 4.37 (dd, Jϭ3.5, 8.5 Hz,. The stereochemistry of the double bond at C-20 (22) was proposed to be (E) since the signal for C-21 was observed at d 13.2 in the 13 C-NMR spectrum of 1, while the methyl carbon of a (Z)-type structure is usually observed at about d 20-30. 7,8) From the above results, the structure of 1 was determined as 3b,6a,12b,24x-tetrahydroxy-dammar-20 (22)

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Panax Species

2020

Secondary Metabolites of Medicinal Plants

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Ginsenoside Rg5, a genuine dammarane glycoside from Korean red ginseng

Cited by 59 publications

References 1 publication

Anticarcinogenic Effect of Panax ginseng C.A. Meyer and Identification of Active Compounds

Anticarcinogenic Effect of Panax ginseng C.A. Meyer and Identification of Active Compounds

Six New Dammarane-type Triterpene Saponins from the Leaves of Panax ginseng

Panax Species

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