• Title/Summary/Keyword: (20S)-ginsenoside $Rh_2$

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Transformation Techniques for the Large Scale Production of Ginsenoside Rg3 (Ginsenoside Rg3의 함량증가를 위한 변환 기술)

  • Nam, Ki Yeul;Choi, Jae Eul;Park, Jong Dae
    • Korean Journal of Medicinal Crop Science
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    • v.21 no.5
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    • pp.401-414
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    • 2013
  • Ginsenoside Rg3 (G-Rg3) contained only in red ginseng has been found to show various pharmacological effects such as an anticancer, antiangiogenetic, antimetastastic, liver protective, neuroprotective immunomodulating, vasorelaxative, antidiabetic, insulin secretion promoting and antioxidant activities. It is well known that G-Rg3 could be divided into 20(R)-Rg3 and 20(S)-Rg3 according to the hydroxyl group attached to C-20 of aglycone, whose structural characteristics show different pharmacological activities. It has been reported that G-Rg3 is metabolized to G-Rh2 and protopanaxadiol by the conditions of the gastric acid or intestinal bacteria, thereby these metabolites could be absorbed, suggesting its absolute bioavailability (2.63%) to be very low. Therefore, we reviewed the chemical, physical and biological transformation methods for the production on a large scale of G-Rg3 with various pharmacological effects. We also examined the influence of acid and heat treatment-induced potentials on for the preparation method of higher G-Rg3 content in ginseng and ginseng products. Futhermore, the microbial and enzymatic bio-conversion technologies could be more efficient in terms of high selectivity, efficiency and productivity. The present review discusses the available technologies for G-Rg3 production on a large scale using chemical and biological transformation.

A Structure-Function Relationship Exists for Ginsenosides in Reducing Cell Proliferation and Inducing Apoptosis in THP-1 Cells

  • Popovich David G.;Kitts David D.
    • Proceedings of the Ginseng society Conference
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    • 2002.10a
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    • pp.545-555
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    • 2002
  • Ginsenosides of 20(S)-protopanaxadiol and 20(S)-protopanaxatriol classification including the aglycones, PD, PI and ginsenosides Rh2, Rhl were shown to posses characteristic effects on proliferation of THP-l human leukaemia cells. A similar result was not apparent for ginsenoside Rg3 or dexamathasone. The concentration to inhibit $50\%$ of cells $(LC_{50})$ for PD, Rh2, PI and Rhl were 13 ${\mu}g/mL,\;15{\mu}g/mL,\;19{\mu}g/mL\;and\;210\;{\mu}g/mL$ respectively. Cell cycle analysis showed apoptosis with PD and PI treatment of THP-1 cells resulting in a build up of sub-G1 cells after 24, 48 and 72 hours of treatment. Rh2, and dexamathasone treatments also increased apoptotic cells after 24 hours, where as Rhl did not. After 48 and 72 hours Rh2, Rhl and dexamathasone similarly increased apoptosis, but these effects were significantly (P<0.05) lower than observed for both PD and PI treatments. Furthermore, treatments that produced the largest build up of apoptotic cells were also found to have the largest release of lactate dehydrogenase (LDH). It can be concluded from these studies that the presence of sugars to PD and PI aglycone structure reduces the potency to induce apoptosis, and alternately alter membrane integrity. These cytotoxic effects to THP-l cells were different from dexamethasone.

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A new validated analytical method for the quality control of red ginseng products

  • Kim, Il-Woung;Cha, Kyu-Min;Wee, Jae Joon;Ye, Michael B.;Kim, Si-Kwan
    • Journal of Ginseng Research
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    • v.37 no.4
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    • pp.475-482
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    • 2013
  • The main active components of Panax ginseng are ginsenosides. Ginsenoside Rb1 and Rg1 are accepted as marker substances for quality control worldwide. The analytical methods currently used to detect these two compounds unfairly penalize steamed and dried (red) P. ginseng preparations, because it has a lower content of those ginsenosides than white ginseng. To manufacture red ginseng products from fresh ginseng, the ginseng roots are exposed to high temperatures for many hours. This heating process converts the naturally occurring ginsenoside Rb1 and Rg1 into artifact ginsenosides such as ginsenoside Rg3, Rg5, Rh1, and Rh2, among others. This study highlights the absurdity of the current analytical practice by investigating the time-dependent changes in the crude saponin and the major natural and artifact ginsenosides contents during simmering. The results lead us to recommend (20S)- and (20R)-ginsenoside Rg3 as new reference materials to complement the current P. ginseng preparation reference materials ginsenoside Rb1 and Rg1. An attempt has also been made to establish validated qualitative and quantitative analytical procedures for these four compounds that meet International Conference of Harmonization (ICH) guidelines for specificity, linearity, range, accuracy, precision, detection limit, quantitation limit, robustness and system suitability. Based on these results, we suggest a validated analytical procedure which conforms to ICH guidelines and equally values the contents of ginsenosides in white and red ginseng preparations.

Antiviral effects of Korean Red Ginseng on human coronavirus OC43

  • Chi Hwan Jeong;Jisu Kim;Bo Kyeong Kim;Kang Bin Dan;Hyeyoung Min
    • Journal of Ginseng Research
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    • v.47 no.2
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    • pp.329-336
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    • 2023
  • Background: Panax ginseng Meyer is a medicinal plant well-known for its antiviral activities against various viruses, but its antiviral effect on coronavirus has not yet been studied thoroughly. The antiviral activity of Korean Red Ginseng (KRG) and ten ginsenosides against Human coronavirus OC43 (HCoV-OC43) was investigated in vitro. Methods: The antiviral response and mechanism of action of KRG extract and ginsenoside Rc, Re, Rf, Rg1, Rg2-20 (R) and -20 (S), Rg3-20 (R) and -20 (S), and Rh2-20 (R) and -20 (S), against the human coronavirus strain OC43 were investigated by using plaque assay, time of addition assay, real-time PCR, and FACS analysis. Results: Virus plaque formation was reduced in KRG extract-treated and HCoV-OC43-infected HCT-8 cells. KRG extract decreased the viral proteins (Nucleocapsid protein and Spike protein) and mRNA (N and M gene) expression, while increased the expression of interferon genes. Conclusion: KRG extract exhibits antiviral activity by enhancing the expression of interferons and can be used in treating infections caused by HCoV-OC43.

20(S)-ginsenoside Rh2 induces caspase-dependent promyelocytic leukemia-retinoic acid receptor A degradation in NB4 cells via Akt/Bax/caspase9 and TNF-α/caspase8 signaling cascades

  • Zhu, Sirui;Liu, Xiaoli;Xue, Mei;Li, Yu;Cai, Danhong;Wang, Shijun;Zhang, Liang
    • Journal of Ginseng Research
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    • v.45 no.2
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    • pp.295-304
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    • 2021
  • Background: Acute promyelocytic leukemia (APL) is a hematopoietic malignancy driven by promyelocytic leukemia-retinoic acid receptor A (PML-RARA) fusion gene. The therapeutic drugs currently used to treat APL have adverse effects. 20(S)-ginsenoside Rh2 (GRh2) is an anticancer medicine with high effectiveness and low toxicity. However, the underlying anticancer mechanisms of GRh2-induced PML-RARA degradation and apoptosis in human APL cell line (NB4 cells) remain unclear. Methods: Apoptosis-related indicators and PML-RARA expression were determined to investigate the effect of GRh2 on NB4 cells. Z-VAD-FMK, LY294002, and C 87, as inhibitors of caspase, and the phosphatidylinositol 3-kinase (PI3K) and tumor necrosis factor-α (TNF-α) pathways were used to clarify the relationship between GRh2-induced apoptosis and PML-RARA degradation. Results: GRh2 dose- and time-dependently decreased NB4 cell viability. GRh2-induced apoptosis, cell cycle arrest, and caspase3, caspase8, and caspase9 activation in NB4 cells after a 12-hour treatment. GRh2-induced apoptosis in NB4 cells was accompanied by massive production of reactive oxygen species, mitochondrial damage and upregulated Bax/Bcl-2 expression. GRh2 also induced PML/PML-RARA degradation, PML nuclear bodies formation, and activation of the downstream p53 pathway in NB4 cells. Z-VAD-FMK inhibited caspase activation and significantly reversed GRh2-induced apoptosis and PML-RARA degradation. GRh2 also upregulated TNF-α expression and inhibited Akt phosphorylation. LY294002, an inhibitor of the PI3K pathway, enhanced the antitumor effects of GRh2, and C 87, an inhibitor of the TNF-α pathway, reversed NB4 cell viability, and GRh2-mediated apoptosis in a caspase-8-dependent manner. Conclusion: GRh2 induced caspase-dependent PML-RARA degradation and apoptosis in NB4 cells via the Akt/Bax/caspase9 and TNF-α/caspase8 pathways.

Simultaneous Quantification of 13 Ginsenosides by LC-MS/MS and its Application in Diverse Ginseng Extracts

  • Jo, Jung Jae;Cho, Pil Joung;Lee, Sangkyu
    • Mass Spectrometry Letters
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    • v.9 no.2
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    • pp.41-45
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    • 2018
  • Ginseng (Panax ginseng Meyer) has been used as traditional herbal drug in Asian countries. Ginsenosides are major components having pharmacological and biological efficacy like anti-inflammatory, anti-diabetic and anti-tumor effects. To control the quality of the components in diverse ginseng products, we developed a new quantitative method using LC-MS/MS for 13 ginsenosides; Rb1, Rb2, Rc, Rd, Re, Rf, 20(S)-Rh1, 20(S)-Rh2, Rg1, 20(S)-Rg3, F1, F2, and compound K. This method was successfully validated for linearity, precision, and accuracy. This quantification method applied in four representative ginseng products; fresh ginseng powder, white ginseng powder, red ginseng extract powder, and red ginseng extract. Here the amounts of the 13 ginsenosides in the various type of ginseng samples could be analyzed simultaneously and expected to be suitable for quality control of ginseng products.

Changes of Ginsenosides and Physiochemical Properties in Ginseng by New 9 Repetitive Steaming and Drying Process (새로운 자동 구증구포방법에 의한 인삼사포닌의 변환 및 이화학적 특성)

  • Jin, Yan;Kim, Yeon-Ju;Jeon, Ji-Na;Wang, Chao;Min, Jin-Woo;Jung, Sun-Young;Yang, Deok-Chun
    • Korean Journal of Plant Resources
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    • v.25 no.4
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    • pp.473-481
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    • 2012
  • This study was conducted to investigate the contents of ginsenosides and physiochemical properties of Panax ginseng after 9 times steaming and drying treatment by using the new auto steamer which is more fast and simple than previous report. In the process of steaming and drying, the content of six major ginsenosides such as Rg1, Re, Rb1, Rc, Rb2 and Rd were gradually decreased. On the other hand, the content of seven minor ginsenosides includes Rh1, 20(S)-Rg2, 20(R)-Rg2, 20(S)-Rg3, 20(R)-Rg3, Rk1 and Rg5 were gradually increased. We observed the protopanxadiol ginsenosides such as Rb1, Rb2, Rc and Rd were converted into 20(S)-Rg3, 20(R)-Rg3, Rk1 and Rg5; similarly protopanxatriol ginsenosides of Rg1 and Re were converted into Rh1, 20(S)-Rg2 and 20(R)-Rg2. Based on the result of fresh ginseng, the contents of reducing sugar, acidic polysaccharide and total phenolic compounds were gradually increased and reached to maximum at 7 times repetitive steaming process of the fresh ginseng. Whereas DPPH radical scavenging activities were gradually decreased to 68% at 7 times steaming. New auto 9 repetitive steaming and drying process has similar production with original methods, but content of benzo(a)pyrene were not almost detected comparatively taking less time. The present results suggested that this method is best for the development of value-added ginseng industry related products.

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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Production of Minor Gisenosides from Gypenoside V (Gypenoside V로부터 minor ginsenosides의 생산)

  • Son, Na-Ri;Min, Jin-Woo;Jang, Mi;Kim, Hyo-Yeon;Jeon, Ji-Na;Yang, Deok-Chun
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2010.10a
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    • pp.20-20
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    • 2010
  • Panax ginseng C.A Meyer is frequently taken orally as a traditional herbal medicine in Asian countries. The major components of ginseng are ginsenoside, which are pharmaceutical activity. The six major ginsenosides, including Rb1, Rb2, Rc, Rd, Re and Rg1 account for 90% of total ginsenosides. Even though the minor ginsenosides, including Rg3, Rh2 and compound K has high pharmacetical activities, the price of minor ginsenosides is too high. Therefore we isolated the gypenoside V and made it converted to minor ginsenosides. In the plant Gynostemma pentaphyllum Makino, gypenosdie V was presented as dominant saponin (content about 2.4%), and was similar to protopanaxadol type ginsenosides such as ginsenoside Rb1. In this study, we confirmed that the coversion of gypenoside V to minor ginsenosides after using the various treatment such as heating, acid treatment, commercial edible enzyme, and lactobacillus. Consequently, we optimizied the transformation of gypenoside V to minor ginsenoside using Thin Layer Chromatography (TLC), High Performance Liquid Chromatography (HPLC), Time-of-flight Mass Spectrometry (LC/TOF/MS).

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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.