• 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.

• Natural Product Sciences
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• v.23 no.4
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• pp.291-298
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• 2017

Six dammarane-type triterpenoids, dammar-24-en-$3{\beta}$-ol (1), $3{\beta}$-epicabraleahydroxy lactone (2), (E)-25-hydroperoxydammar-23-en-$3{\beta}$,20-diol (3), dammar-24-en-$3{\beta}$,20-diol (4), $3{\beta}$-acetyl-20S,24S-epoxy-25-hydroxydammarane (5), and $3{\beta}$-epiocotillol (6) were isolated from the methanolic extract of the bark of Aglaia elliptica. The chemical structure were identified on the basis of spectroscopic evidence and by comparison with those spectra previously reported. Compounds 1 - 6 were isolated first time from this plant. Compounds 1 - 6, along with a known synthetic analog, cabraleone (7) were evaluated their cytotoxic activity against P-388 murine leukimia cells in vitro. Among those compounds $3{\beta}$-acetyl-20S,24S-epoxy-25-hydroxydammarane (5) showed strongest cytotoxic activity with $IC_{50}$ value of $8.02{\pm}0.06{\mu}M$.

• Journal of Ginseng Research
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• v.43 no.3
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• pp.377-384
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• 2019

Background: Inflammation is widespread in the clinical pathology and closely associated to the progress of many diseases. Triterpenoid saponins as a key group of active ingredients in Panax notoginseng (Burk.) F.H. Chen were demonstrated to show antiinflammatory effects. However, the chemical structures of saponins in the leaves and stems of Panax notoginseng (PNLS) are still not fully clear. Herein, the isolation, purification and further evaluation of the antiinflammatory activity of dammarane-type triterpenoid saponins from PNLS were conducted. Methods: Silica gel and reversed-phase C8 column chromatography were used. Furthermore, preparative HPLC was used as a final purification technique to obtain minor saponins with high purities. MS, NMR experiments, and chemical methods were used in the structural identifications. The antiinflammatory activities of the isolated saponins were assessed by measuring the nitric oxide production in RAW 264.7 cells stimulated by lipopolysaccharides. Real-time reverse transcription polymerase chain reaction was used to measure the gene expressions of inflammation-related gene. Results: Eight new minor dammarane-type triterpene oligoglycosides, namely notoginsenosides LK1-LK8 (1-8) were obtained from PNLS, along with seven known ones. Among the isolated saponins, gypenoside IX significantly suppressed the nitric oxide production and inflammatory cytokines including tumor necrosis $factor-{\alpha}$, interleukin 10, interferon-inducible protein 10 and $interleukin-1{\beta}$. Conclusion: The eight saponins may enrich and expand the chemical library of saponins in Panax genus. Moreover, it is reported for the first time that gypenoside IX showed moderate antiinflammatory activity.

• 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.

• 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.

• Archives of Pharmacal Research
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• v.19 no.6
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• pp.551-553
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• 1996

A genuine dammarane glycoside, named ginsenoside $Rg_{5}$, has been isolated by repeated column chromatography and preparative HPLC from the MeOH extract of Korean red ginseng (Panax ginseng C.A. Meyer). The chemical structure of ginsenoside$ Rg_{5}$ was determined as $3-O-[{\beta}-D-glucopyranosyl (1{\rightarrow}2)-{\beta}-D-glucopyranosyl]$ dammar-20(22), $24-diene-3{\beta},12{\beta}-diol$ by spectral and chemical methods. The stereostructure of a double bond at C-20(22) of ginsenoside $Rg_{5}$ was characterized as (E) from the chemical shift of C-21 in the $^{13}C-NMR $and a NOESY experiment in the $^{1}H-NMR$.

• Natural Product Sciences
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• v.24 no.4
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• pp.229-234
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• 2018

Ginseng products available in different forms and preparations are reported to have varied bioactivities and chemical compositions. In our previous study, four new dammarane-type ginsenosides were isolated from Panax ginseng, which are ginsenoside Rg18 (1), 6-acetyl ginsenoside Rg3 (2), ginsenoside Rs11 (3), and ginsenoside Re7 (4). Accordingly, the goal of this study was to determine the distribution and content of these newly characterized ginsenosides in different ginseng products. The content of compounds 1 - 4 in different ginseng products was determined via HPLC-UV. The samples included ginseng roots from different ginseng species, roots harvested from different localities in Korea, and samples harvested at different cultivation ages and processed under different manufacturing methods. The four ginsenosides were present at varying concentrations in the different ginseng samples examined. The variations in their content could be attributed to species variation, and differences in cultivation conditions and manufacturing methods. The total concentration of compounds 1 - 4 were highest in ginseng obtained from Geumsan ($185{\mu}g/g$), white-6 yr ginseng ($150{\mu}g/g$), and P. quinquefolius ($186{\mu}g/g$). The results of this study provide a basis for the optimization of cultivation conditions and manufacturing methods to maximize the yield of the four new ginsenosides in ginseng.

• Journal of Ginseng Research
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• v.47 no.6
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• pp.694-705
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• 2023

Panax ginseng Meyer is a traditional Chinese medicine that is widely used as tonic in Asia. The main pharmacologically active components of ginseng are the dammarane-type ginsenosides, which have been shown to have anti-cancer, anti-inflammatory, immunoregulatory, neuroprotective, and metabolic regulatory activities. Moreover, some of ginsenosides (eg, Rh2 and Rg3) have been developed into nutraceuticals. However, the utilization of ginsenosides in clinic is restrictive due to poor permeability in cells and low bioavailability in human body. Obviously, the dammarane skeleton and glycosyls of ginsenosides are responsible for these limitations. Therefore, improving the oral bioavailability of ginsenosides has become a pressing issue. Here, based on the structures of ginsenosides, we summarized the understanding of the factors affecting the oral bioavailability of ginsenosides, introduced the methods to enhance the oral bioavailability and proposed the future perspectives on improving the oral bioavailability of ginsenosides.

• Journal of Ginseng Research
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• v.47 no.5
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• pp.605-614
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• 2023

Ginsenosides are bioactive components of Panax ginseng with many functions such as anti-aging, anti-oxidation, anti-inflammatory, anti-fatigue, and anti-tumor. Ginsenosides are categorized into dammarane, oleanene, and ocotillol type tricyclic triterpenoids based on the aglycon structure. Based on the sugar moiety linked to C-3, C-20, and C-6, C-20, dammarane type was divided into protopanaxadiol (PPD) and protopanaxatriol (PPT). The effects of ginsenosides on skin disorders are noteworthy. They play antiaging roles by enhancing immune function, resisting melanin formation, inhibiting oxidation, and elevating the concentration of collagen and hyaluronic acid. Thus, ginsenosides have previously been widely used to resist skin diseases and aging. This review details the role of ginsenosides in the anti-skin aging process from mechanisms and experimental research.

• Journal of Ginseng Research
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• v.44 no.3
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• pp.405-412
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• 2020

Background: Root rot is a serious destructive disease of Panax notoginseng, a famous cultivated araliaceous herb called Sanqi or Tianqi in Southwest China. Methods: The chemical substances of Sanqi rot roots were explored by chromatographic techniques. MS, 1D/2D-NMR, and single crystal X-ray diffraction were applied to determine the structures. Murine macrophage RAW264.7 and five human cancer cell lines were used separately for evaluating the antiinflammatory and cytotoxic activities. Results and Conclusion: Thirty dammarane-type triterpenes and saponins were isolated from the rot roots of P. notoginseng. Among them, seven triterpenes, namely, 20(S)-dammar-25-ene-24(S)-hydroperoxyl-3β,6α,12β,20-tetrol (1), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-6α,12β,20-triol (2), 20(S)-dammar-12-oxo-23-ene-25-hydroperoxyl-3β,6α,20-triol (3), 20(S)-dammar-3-oxo-23-ene-25-hydroperoxyl-12β,20-diol (4), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid (5), 20(S),24(R)-epoxy-3,4-seco-dammar-25-hydroxy-12-one-3-oic acid methyl ester (6), and 6α-hydroxy-22,23,24,25,26,27-hexanordammar-3,12,20-trione (7), are new compounds. In addition, 12 known ones (12-16 and 19-25) were reported in Sanqi for the first time. The new Compound 1 showed comparable antiinflammatory activity on inhibition of NO production to the positive control, whereas the known compounds 9, 12, 13, and 16 displayed moderate cytotoxicities against five human cancer cell lines. The results will provide scientific basis for understanding the chemical constituents of Sanqi rot roots and new candidates for searching antiinflammatory and antitumor agents.