• Title/Summary/Keyword: Protopanaxatriol

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Complete $^1H$-NMR and $^{13}C$-NMR spectral analysis of the pairs of 20(S) and 20(R) ginsenosides

  • Yang, Heejung;Kim, Jeom Yong;Kim, Sun Ok;Yoo, Young Hyo;Sung, Sang Hyun
    • Journal of Ginseng Research
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    • v.38 no.3
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    • pp.194-202
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    • 2014
  • Background: Ginsenosides, the major ingredients of Panax ginseng, have been studied for many decades in Asian countries as a result of their wide range of pharmacological properties. The less polar ginsenosides, with one or two sugar residues, are not present in nature and are produced during manufacturing processes by methods such as heating, steaming, acid hydrolysis, and enzyme reactions. $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the identification of the less polar ginsenosides are often unavailable or incomplete. Methods: We isolated 21 compounds, including 10 pairs of 20(S) and 20(R) less polar ginsenosides (1-20), and an oleanane-type triterpene (21) from a processed ginseng preparation and obtained complete $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the following compounds, referred to as compounds 1-21 for rapid identification: 20(S)-ginsenosides Rh2 (1), 20(R)-Rh2 (2), 20(S)-Rg3 (3), 20(R)-Rg3 (4), 6'-O-acetyl-20(S)-Rh2 [20(S)-AcetylRh2] (5), 20(R)-AcetylRh2 (6), 25-hydroxy-20(S)-Rh2 (7), 25-hydroxy-20(S)-Rh2 (8), 20(S)-Rh1 (9), 20(R)-Rh1 (10), 20(S)-Rg2 (11), 20(R)-Rg2 (12), 25-hydroxy-20(S)-Rh1 (13), 25-hydroxy-20(R)-Rh1 (14), 20(S)-AcetylRg2 (15), 20(R)-AcetylRg2 (16), Rh4 (17), Rg5 (18), Rk1 (19), 25-hydroxy-Rh4 (20), and oleanolic acid 28-O-b-D-glucopyranoside (21).

Ginsenoside Rg1 from Panax ginseng enhances myoblast differentiation and myotube growth

  • Go, Ga-Yeon;Lee, Sang-Jin;Jo, Ayoung;Lee, Jaecheol;Seo, Dong-Wan;Kang, Jong-Sun;Kim, Si-Kwan;Kim, Su-Nam;Kim, Yong Kee;Bae, Gyu-Un
    • Journal of Ginseng Research
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    • v.41 no.4
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    • pp.608-614
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    • 2017
  • Background: Ginsenoside Rg1 belongs to protopanaxatriol-type ginsenosides and has diverse pharmacological activities. In this report, we investigated whether Rg1 could upregulate muscular stem cell differentiation and muscle growth. Methods: C2C12 myoblasts, MyoD-transfected 10T1/2 embryonic fibroblasts, and HEK293T cells were treated with Rg1 and differentiated for 2 d, subjected to immunoblotting, immunocytochemistry, or immunoprecipitation. Results: Rg1 activated promyogenic kinases, p38MAPK (mitogen-activated protein kinase) and Akt signaling, that in turn promote the heterodimerization with MyoD and E proteins, resulting in enhancing myogenic differentiation. Through the activation of Akt/mammalian target of rapamycin pathway, Rg1 induced myotube growth and prevented dexamethasone-induced myotube atrophy. Furthermore, Rg1 increased MyoD-dependent myogenic conversion of fibroblast. Conclusion: Rg1 upregulates promyogenic kinases, especially Akt, resulting in improvement of myoblast differentiation and myotube growth.

Extraction of Ginseng Saponins in Supercritical Ammonia Fluids (초임계 암모니아 유체에서의 인삼 사포닌 추출)

  • O, Sang O;Seok, Hwi Yeong
    • Journal of the Korean Chemical Society
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    • v.34 no.6
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    • pp.663-672
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    • 1990
  • The extraction of ginseng saponins with near critical or supercritical ammonia(SCF-NH$_3$) was carried out at 80$^{\circ}C$-160$^{\circ}C$ and ammonia densities of 339.8-525 $mg/cm^3$. In order to evaluate brownish color of white ginseng extracts, a spetrophotometric method was applied in ultraviolet and visible range. The extractibilities of ginseonoside $Rb_1$, -$Rb_2$, -Rc, -Rd, -Re, -Rf, $-Rg_1$, and $-Rg_2$ were determined by high performance liquid choromatography. The best extractability was 7.36% at 133$^{\circ}C$ and 403 $\pm$ 24.605 $mg/cm^3$. In the case of the high extraction temperature, it is thought that extraction times can be reduced and the selectivity of protopanaxatriol can be increased. The brownish color of extracts is affected by temperature and extractability. When extraction temperature is between 132$^{\circ}C$ and 140$^{\circ}C$, it is shown that the range is the retrograde region where extractablility decrease with increasing temperature.

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Photosynthesis rates, growth, and ginsenoside contents of 2-yr-old Panax ginseng grown at different light transmission rates in a greenhouse

  • Jang, In-Bae;Lee, Dae-Young;Yu, Jin;Park, Hong-Woo;Mo, Hwang-Sung;Park, Kee-Choon;Hyun, Dong-Yun;Lee, Eung-Ho;Kim, Kee-Hong;Oh, Chang-Sik
    • Journal of Ginseng Research
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    • v.39 no.4
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    • pp.345-353
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    • 2015
  • Background: Ginseng is a semishade perennial plant cultivated in sloping, sun-shaded areas in Korea. Recently, owing to air-environmental stress and various fungal diseases, greenhouse cultivation has been suggested as an alternative. However, the optimal light transmission rate (LTR) in the greenhouse has not been established. Methods: The effect of LTR on photosynthesis rate, growth, and ginsenoside content of ginseng was examined by growing ginseng at the greenhouse under 6%, 9%, 13%, and 17% of LTR. Results: The light-saturated net photosynthesis rate ($A_{sat}$) and stomatal conductance ($g_{s}$) of ginseng increased until the LTR reached 17% in the early stage of growth, whereas they dropped sharply owing to excessive leaf chlorosis at 17% LTR during the hottest summer period in August. Overall, 6-17% of LTR had no effect on the aerial part of plant length or diameter, whereas 17% and 13% of LRT induced the largest leaf area and the highest root weight, respectively. The total ginsenoside content of the ginseng leaves increased as the LTR increased, and the overall content of protopanaxatriol line ginsenosides was higher than that of protopanaxadiol line ginsenosides. The ginsenoside content of the ginseng roots also increased as the LTR increased, and the total ginsenoside content of ginseng grown at 17% LTR increased by 49.7% and 68.3% more than the ginseng grown at 6% LTR in August and final harvest, respectively. Conclusion: These results indicate that 13-17% of LTR should be recommended for greenhouse cultivation of ginseng.

Effects of pH and High Temperature Treatment on the Changes of Major Ginsenosides Composition in Korean Red Ginseng Water Extract (pH 및 고온 열처리가 홍삼물추출물의 주종 사포닌 성분변화에 미치는 영향)

  • Choi, Keum-Hee;Kwak, Yi-Seong;Rhee, Man-Hee;Hwang, Mi-Sun;Kim, Seok-Chang;Park, Chae-Kyu;Han, Gyeong-Ho;Song, Kyung-Bin
    • Journal of Ginseng Research
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    • v.32 no.2
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    • pp.127-134
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    • 2008
  • This study was carried out to investigate the changes of ginsenosides composition in Korean red ginseng water extract (RGWE) after heated with high temperatures above $100^{\circ}C$. RGWEs were adjusted with pH 3.0, pH 7.0 and pH 10.0, respectively, and then heated at 100,110 and $120^{\circ}C$ for 30 minutes by using autoclave. Total ginsenosides of RGWE treated with heating showed decreasing tendency when compared with control. By TLC analysis, decreasing effect of ginsenosides in RGWE were significantly observed in the acidic condition of pH 3.0, particulary. By HPLC analysis, total ginsenoside of control showed 1.89%, while those of RGWE treated with 100, 110 and $120^{\circ}C$ showed 1.22, 1.05 and 0.97%, respectively. The ratio of protopanaxadiol (PD) to protopanaxatriol (Pr) saponins in control was 1.89, while that of PD/PT in treated RGWEs were level of 1.33 to 1.47. By the result of decreased ratio of PD/PT in RGWE, it was considered that PD type saponin such as ginsenoside$-Rb_{1}$, $-Rb_{1}$, -Rc and -Rd was more unstable than PT type saponin such as ginsenoside-Re and Rg against high temperature heating above $100^{\circ}C$.

Effect of Panax ginseng on the Development and Loss of Morphine Tolerance and Dependence (인삼이 몰핀의 내성 및 의존성 형성에 미치는 영향)

  • Kim Hack Seang;Oh Ki Wan
    • Proceedings of the Ginseng society Conference
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    • 1988.08a
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    • pp.151-155
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    • 1988
  • The present study was undertaken to determine the inhibitory effects of orally administered ginseng saponins(SP), protopanaxadiol saponins (PD), and protopanaxatriol saponins(PT) on the development of morphine-induced tolerance and physical dependence in mice. The study also sought to determine the hepatic glutathione contents. which are closely related to the degree of detoxification of mine the effects of GS on morphine 6-dehydrogenase, which catalyzes the production of morphinone from morphine, and the roles of spinal descendign inhibitory systems in the production of antagonism. The results of the present study showed that GS, PD and PT administered orally inhibited the development of morphine induced tolerance and dependence. GS. PD and PT inhibited the reduction of hepatic glutathione concentration in mice treated chronically with morphine and the activity of morphine 6-dehydrogenase, and the activation of spinal descending inhibitory systems was inhibited by GS. So we hypothesized that the results were partially due to the dual action of the test drugs, the inhibition of morphinone production and the activated formation of morphinone-glutathinone conjugation, and the inhibition of the activatin of apinal descending inhibitory systems and the others.

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Growth Characteristics of Ginseng Seedling Transplanting by Self Soil Nusery, Nursery or Hydroponic Culture on Main Field (토직, 상토 및 양액육묘에 의해 생산된 묘삼의 본포 이식 후 생장특성)

  • Park, Hong Woo;Song, Jeong Ho;Kwon, Ki Bum;Lee, Ueong Ho;Son, Ho Jun
    • Korean Journal of Medicinal Crop Science
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    • v.25 no.4
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    • pp.238-243
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    • 2017
  • Background: The production method of ginseng seedlings for ginseng cultivation is very important to ensure healthy rooting system as well as high quality, and yield of the resultant plants. This study was carried out to compare the growth characteristics of 2-year-old ginseng plants that were produced from seedlings grown in self soil nursery (SSN), nursery soil (NS) or hydroponic culture (HC). Methods and Results: The shading prop used was composed of four-layered 4 polyethylene (blue 3 + black 1) shade screen. The management of main field was done by inserting oil cake (1,200 kg/10 a) and then allowing Sudan grass to grow for a year. Seedling transplantation was carried out on April 6. Root growth was measured on October 25. Root weight was observed to be excellent at 6.0 g, following SSN transplantation. Root length was 21.2 cm for HC seedlings, but these plants had a physiological disorder (i.e., rusty root), in 83.5% plants of this treatment. The ratio of PD/PT (protopanaxadiol saponins / protopanaxatriol saponins) was higher in NS seedlings. Plant analysis revealed that Fe content was lower in HC seedlings with high rustiness. The growth of 2-years-old ginseng was different following these varying seedling cultivation methods, but seedlings from NS were not different from those grown in SSN. Conclusions: For the propagation of 2-year-old ginseng plants, NS seedlings may be a good substitute for SSN seedlings.

Multicomponent assessment and ginsenoside conversions of Panax quinquefolium L. roots before and after steaming by HPLC-MSn

  • Huang, Xin;Liu, Yan;Zhang, Yong;Li, Shuai-Ping;Yue, Hao;Chen, Chang-Bao;Liu, Shu-Ying
    • Journal of Ginseng Research
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    • v.43 no.1
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    • pp.27-37
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    • 2019
  • Background: The structural conversions in ginsenosides induced by steaming or heating or acidic condition could improve red ginseng bioactivities significantly. In this paper, the chemical transformations of red American ginseng from fresh Panax quinquefolium L. under steaming were investigated, and the possible mechanisms were discussed. Methods: A method with reversed-phase high-performance liquid chromatography coupled with linear ion trap mass spectrometry ($HPLC-MS^n$)-equipped electrospray ionization ion source was developed for structural analysis and quantitation of ginsenosides in dried and red American ginseng. Results: In total, 59 ginsenosides of protopanaxadiol, protopanaxatriol, oleanane, and ocotillol types were identified in American ginseng before and after steaming process by matching the molecular weight and/or comparing $MS^n$ fragmentation with that of standards and/or known published compounds, and some of them were determined to be disappeared or newly generated under different steaming time and temperature. The specific fragments of each aglycone-type ginsenosides were determined as well as aglycone hydrated and dehydrated ones. The mechanisms were deduced as hydrolysis, hydration, dehydration, and isomerization of neutral and acidic ginsenosides. Furthermore, the relative peak areas of detected compounds were calculated based on peak areas ratio. Conclusion: The multicomponent assessment of American ginseng was conducted by $HPLC-MS^n$. The result is expected to provide possibility for holistic evaluation of the processing procedures of red American ginseng and a scientific basis for the usage of American ginseng in prescription.

Non-clinical pharmacokinetic behavior of ginsenosides

  • Won, Hyo-Joong;Kim, Hyun Il;Park, Taejun;Kim, Hyeongmin;Jo, Kanghee;Jeon, Hyojin;Ha, Seo Jun;Hyun, Jung Min;Jeong, Aeri;Kim, Jung Sik;Park, Ye Jin;Eo, Yun Ho;Lee, Jaehwi
    • Journal of Ginseng Research
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    • v.43 no.3
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    • pp.354-360
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    • 2019
  • Ginsenosides, the major active ingredients of ginseng and other plants of the genus Panax, have been used as natural medicines in the East for a long time; in addition, their popularity in the West has increased owing to their various beneficial pharmacological effects. There is therefore a wealth of literature regarding the pharmacological effects of ginsenosides. In contrast, there are few comprehensive studies that investigate their pharmacokinetic behaviors. This is because ginseng contains the complicated mixture of herbal materials as well as thousands of constituents with complex chemical properties, and ginsenosides undergo multiple biotransformation processes after administration. This is a significant issue as pharmacokinetic studies provide crucial data regarding the efficacy and safety of compounds. Moreover, there have been many difficulties in the development of the optimal dosage regimens of ginsenosides and the evaluation of their interactions with other drugs. Therefore, this review details the pharmacokinetic properties and profiles of ginsenosides determined in various animal models administered through different routes of administration. Such information is valuable for designing specialized delivery systems and determining optimal dosing strategies for ginsenosides.

Quantitative aspects of the hydrolysis of ginseng saponins: Application in HPLC-MS analysis of herbal products

  • Abashev, Mikhail;Stekolshchikova, Elena;Stavrianidi, Andrey
    • Journal of Ginseng Research
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    • v.45 no.2
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    • pp.246-253
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    • 2021
  • Background: Ginseng is one of the most valuable herbal supplements. It is challenging to perform quality control of ginseng products due to the diversity of bioactive saponins in their composition. Acid or alkaline hydrolysis is often used for the structural elucidation of these saponins and sugars in their side chains. Complete transformation of the original ginsenosides into their aglycones during the hydrolysis is one of the ways to determine a total saponin group content. The main hurdle of this approach is the formation of various by-products that was reported by many authors. Methods: Separate HPLC assessment of the total protopanaxadiol, protopanaxatriol and ocotillol ginsenoside contents is a viable alternative to the determination of characteristic biomarkers of these saponin groups, such as ginsenoside Rf and pseudoginsenoside F11, which are commonly used for authentication of P. ginseng Meyer and P. quinquefolius L. samples respectively. Moreover, total ginsenoside content is an ideal aggregated parameter for standardization and quality control of ginseng-based medicines, because it can be directly applied for saponin dosage calculation. Results: Different hydrolysis conditions were tested to develop accurate quantification method for the elucidation of total ginsenoside contents in herbal products. Linearity, limits of quantification, limits of detection, accuracy and precision were evaluated for the developed HPLC-MS method. Conclusion: Alkaline hydrolysis results in fewer by-products than sugar elimination in acidic conditions. An equimolar response, as a key parameter for quantification, was established for several major ginsenosides. The developed approach has shown acceptable results in the analysis of several different herbal products.