• Title/Summary/Keyword: minor ginsenosides

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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.

Oleanolic acid 3-acetate, a minor element of ginsenosides, induces apoptotic cell death in ovarian carcinoma and endometrial carcinoma cells via the involvement of a reactive oxygen species-independent mitochondrial pathway

  • Jo, Hantae;Oh, Jeong-Hyun;Park, Dong-Wook;Lee, Changho;Min, Churl K.
    • Journal of Ginseng Research
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    • v.44 no.1
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    • pp.96-104
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    • 2020
  • Objectives: Oleanolic acid, a minor element of ginsenosides, and its derivatives have been shown to have cytotoxicity against some tumor cells. The impact of cytotoxic effect of oleanolic acid 3-acetate on ovarian cancer SKOV3 cells and endometrial cancer HEC-1A cells were examined both in vivo and in vitro to explore the underlying mechanisms. Methods: Cytotoxic effects of oleanolic acid 3-acetate were assessed by cell viability, phosphatidylserine exposure on the cell surface, mitochondrial release of cytochrome C, nuclear translocation of apoptosis-inducing factor, depolarization of mitochondrial transmembrane potential (∆Ψm), and generation of reactive oxygen species (ROS). In vivo inhibition of tumor growth was also assessed with xenografts in immunocompromised mice. Results: Oleanolic acid 3-acetate exhibited potent cytotoxicity toward SKOV3 and HEC-1A cells by decreasing cell viability in a concentration-dependent manner. Importantly, oleanolic acid 3-acetate effectively suppressed the growth of SKOV3 cell tumor xenografts in immunocompromised mice. Furthermore, oleanolic acid 3-acetate induced apoptotic cell death as revealed by loss of ∆Ψm, release of cytochrome c, and nuclear translocation of apoptosis-inducing factor with a concomitant activation of many proapoptotic cellular components including poly(ADP-ribose) polymerase, Bcl-2, and caspases-8, caspase-3, and caspase-7. Oleanolic acid 3-acetate, however, caused a decrease in ROS production, suggesting the involvement of an ROS-independent pathway in oleanolic acid 3-acetate-induced apoptosis in SKOV3 and HEC-1A cells. Conclusion: These findings support the notion that oleanolic acid 3-acetate could be used as a potent anticancer supplementary agent against ovarian and endometrial cancer. Oleanolic acid 3-acetate exerts its proapoptotic effects through a rather unique molecular mechanism that involves an unconventional ROS-independent but mitochondria-mediated pathway.

Metabolism of Ginsenoside Rg5, a Main Constituent Isolated from Red Ginseng, by Human Intestinal Microflora and Their Antiallergic Effect

  • Shin, Yong-Wook;Bae, Eun-Ah;Han, Myung-Joo;Kim, Dong-Hyun
    • Journal of Microbiology and Biotechnology
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    • v.16 no.11
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    • pp.1791-1798
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    • 2006
  • When ginsenoside Rg5, a main component isolated from red ginseng, was incubated with three human fecal microflora for 24 h, all specimens showed hydrolyzing activity: all specimens produced ginsenoside Rh3 as a main metabolite, but a minor metabolite $3{\beta},12{\beta}$-dihydroxydammar-21(22),24-diene (DD) was observed in two specimens. To evaluate the antiallergic effect of ginsenoside Rg5 and its metabolites, the inhibitory effect of ginsenoside Rg5 and its metabolite ginsenoside Rh3 against RBL-2H3 cell degranulation, mouse passive cutaneous anaphylaxis (PCA) reaction induced by the IgE-antigen complex, and mouse ear skin dermatitis induced by 12-O-tetradecanoilphorbol-13-acetate (TPA) were measured. Ginsenosides Rg5 and Rh3 potently inhibited degranulation of RBL-2H3 cells. These ginsenosides also inhibited mRNA expression of proinflammatory cytokines IL-6 and $TNF-{\alpha}$ in RBL-2H3 cells stimulated by IgE-antigen. Orally and intraperitoneally administered ginsenoside Rg3 and orally administered ginsenoside Rg5 to mice potently inhibited the PCA reaction induced by IgE-antigen complex. However, intraperitoneally administered ginsenoside Rg5 nearly did not inhibit the PCA reaction. These ginsenosides not only suppressed the swelling of mouse ears induced by TPA, but also inhibited mRNA expression of cyclooxygenase-2, $TNF-{\alpha}$, and IL-4 and activation of transcription factor NF-kB. These inhibitions of ginsenoside Rh3 were more potent than those of ginsenoside Rg5. These findings suggest that ginsenoside Rg5 may be metabolized in vivo to ginsenoside Rh3 by human intestinal microflora, and ginsenoside Rh3 may improve antiallergic diseases, such as rhinitis and dermatitis.

Identification of mountain-cultivated ginseng and cultivated ginseng using UPLC/oa-TOF MSE with a multivariate statistical sample-profiling strategy

  • Xu, Xin-fang;Cheng, Xian-long;Lin, Qing-hua;Li, Sha-sha;Jia, Zhe;Han, Ting;Lin, Rui-chao;Wang, Dan;Wei, Feng;Li, Xiang-ri
    • Journal of Ginseng Research
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    • v.40 no.4
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    • pp.344-350
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    • 2016
  • Background: Mountain-cultivated ginseng (MCG) and cultivated ginseng (CG) both belong to Panax ginseng and have similar ingredients. However, their pharmacological activities are different due to their significantly different growth environments. Methods: An ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS/MS)-based approach was developed to distinguish MCG and CG. Multivariate statistical methods, such as principal component analysis and supervised orthogonal partial-least-squares discrimination analysis were used to select the influential components. Results: Under optimized UPLC-QTOF-MS/MS conditions, 40 ginsenosides in both MCG and CG were unambiguously identified and tentatively assigned. The results showed that the characteristic components of CG and MCG included ginsenoside Ra3/isomer, gypenoside XVII, quinquenoside R1, ginsenoside Ra7, notoginsenoside Fe, ginsenoside Ra2, ginsenoside Rs6/Rs7, malonyl ginsenoside Rc, malonyl ginsenoside Rb1, malonyl ginsenoside Rb2, palmitoleic acid, and ethyl linoleate. The malony ginsenosides are abundant in CG, but higher levels of the minor ginsenosides were detected in MCG. Conclusion: This is the first time that the differences between CG and MCG have been observed systematically at the chemical level. Our results suggested that using the identified characteristic components as chemical markers to identify different ginseng products is effective and viable.

Anticancer activity of ginsenosides Rh2 on various cancer cells

  • Seun Eui Kim;Myoung-Hoon Lee;Hye-Myoung Jang;Wan-Taek Im;Joontaik Lee;Sang-Hwan Kim;Gwang Joo Jeon
    • Journal of Animal Reproduction and Biotechnology
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    • v.38 no.3
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    • pp.131-142
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    • 2023
  • Background: This study has mainly focused on finding pharmacological effects of ginsenosides that can reduce the unwanted side effects of the cytotoxic anticancer drugs and are highly effective on prostate cancer, colorectal cancer, liver cancer, hormone-dependent breast cancer, triple-negative breast cancer, and brain cancer (neuroblastoma). Methods: Minor and rare ginsenosides (GS) of Rh2 which have a high absorption ability and excellent pharmacological actions were treated with the 6 different types of cancer cell lines and their anticancer activities were investigated by analyzing gene expressions associated with various cancers through qPCR and other relevant methods. Results: In cancer cells exposed to Rh2, cell viability and cell migration were reduced, and apoptosis was induced. Each cancer cell was divided into three groups according to the cell proliferation response by Rh2; 1) A group in which the cell viability decreases inversely to an increase in Rh2 treatment concentration; 2) A group in which the cell viability rapidly decreases in Rh2 treatment above a certain level of concentration; 3) A group in which the cell viability was not suppressed below 20-30% even with 100 μL of Rh2, the highest concentration used in this study. Conclusions: It was shown that Rh2 has a significant effect on inhibiting the proliferation of prostate cancer cells and hormone-dependent breast cancer cells.

Conversion of Ginsenoside $Rb_1$ by Ginseng Soil Bacterium Cellulosimicrobium sp. Gsoil 235 According to Various Culture Broths (인삼 토양 미생물 Cellulosimicrobium sp. Gsoil 235의 배지조성에 따른 Ginsenoside $Rb_1$ 전환)

  • Na, Ju-Ryun;Kim, Yu-Jin;Kim, Se-Hwa;Kim, Ho-Bin;Shim, Ju-Sun;Kim, Se-Young;Yang, Deok-Chun
    • Microbiology and Biotechnology Letters
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    • v.37 no.1
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    • pp.55-61
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    • 2009
  • Ginseng saponins (a secondary metabolite, termed ginsenosides) are the principal bioactive ingredients of ginseng, and modification of the sugar chains may markedly change the its biological activity. One of soil bacteria having $\beta$-glucosidase (to transform ginsenoside $Rb_1$) activity was isolated from soil of a ginseng field in Daejeon. 16S rRNA gene sequence analysis revealed that the isolate belonged to the genus Cellulosimicrobium, with highest sequence similarity (99.7%) to Cellulosimicrobium funkei ATCC BAA-$886^T$. The strain, Gsoil 235, could transform ginsenoside $Rb_1$ into Rd, $Rg_3$ and 3 of un-known ginsenosides by the analyses of TLC, HPLC. By investigating its deglycosylation progress, the optimal broth for, $\beta$-glucosidase was nutrient broth (In 48 hours, almost ginsenoside $Rb_1$ could be transformed into minor ginsenosides). On the contrary, the optimal broth for growth was determined as trypic soy broth (TSB).

Conversion of Ginsenoside Rd to Compound K by Crude Enzymes Extracted from Lactobacillus brevis LH8 (Lactobacillus brevis LH8이 생산하는 효소에 의한 Ginsenoside Rd의 Compound K로의 전환)

  • Quan, Lin-Hu;Liang, Zhiqi;Kim, Ho-Bin;Kim, Se-Hwa;Kim, Se-Young;Noh, Yeong-Deok;Yang, Deok-Chun
    • Journal of Ginseng Research
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    • v.32 no.3
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    • pp.226-231
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    • 2008
  • Ginsenosides have been regarded as the principal components responsible for the pharmacological and biological activities of ginseng. Absorption of major ginsenosides from the gastrointestinal tract is extremely low, when ginseng is orally administered. In order to improve absorption and its bioavailability, conversion of major ginsenosides into more active minor ginsenoside is very much required. Here, we isolated lactic acid bacterium (Lactobacillus brevis LH8) having ${\beta}-glucosidase$ activity from Kimchi. Bioconversion ginsenoside Rd by this bacterium in different temperatures was investigated. The maximum activities of crude enzymes precipitated by ethanol were shown in $30^{\circ}C$ and then gradually decreased. In order to compare the effect of pH, the crude enzymes of L. brevis LH8 were mixed in 20mM sodium phosphate buffer (pH 3.5 to pH 8.0) and reacted ginsenoside Rd. Ginsenoside Rd was almost hydrolyzed between pH 6.0 and pH 12.0, but not hydrolyzed under pH 5.0 and above pH 13.0. Ginsenoside Rd was hydrolyzed after 48 h incubation, whereas ginsenoside F2 appeared from 48 h to 72 h, and ginsenoside Rd was almost converted into compound K after 72 h.

Conversion of Ginsenosides by 9 Repetitive Steamings and Dryings Process of Korean Ginseng Root and Its Inhibition of BACE-1 Activity (인삼의 구증구포에 의한 Ginsenoside의 성분변화 및 BACE-1 억제효과)

  • Kim, Do-Wan;Kim, Yu-Jin;Lee, Yun-Jin;Min, Jin-Woo;Kim, Se-Young;Yang, Deok-Chun
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.22 no.6
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    • pp.1557-1561
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    • 2008
  • Red ginseng possibly has new ingredients converted during steaming and dry process from fresh ginseng. Kujeungkupo method which means 9 repetitive steamings and dryings process was used for the production of red ginseng from 6-year old ginseng roots. Saponin was extracted from each red ginseng produced at the 1st, 3rd, 5th, 7th, and 9th during the steaming and drying treatment, and we analyzed saponin content with TLC. Minor saponins, such as ginsenoside-Rg3, -Rh2, compound K, and F2, increased as the process time of steaming and drying, but major saponins (ginsenoside-Rb1, -Rb2, -Rc, -Rd, -Re, -Rf, -Rg1) were decreased. Major saponins were yet observed almost at the 1st process, then degraded as the increasing time of steaming and drying process. Especially, ginsenoside-Re and -Rg were observed as considerable amount after the 1st treatment, but there were no trace of them after the 9th treatment. Ginsenoside-Rg1, -Rb2, and -Rb1 were also reduced remarkedly by 96.6%, 96%, and 92.3%, respectively. Minor saponins were increased significantly, especially for ginsenoside-Rg3 and ginsenoside-F2. These results suggest that Kujeungkupo method is the very useful method for the production of minor ginsenoside-Rg3 and -Rh2.

Biotransformation of Ginsenoside by Lactobacillus brevis THK-D57 Isolated from Kimchi (김치에서 분리한 Lactobacillus brevis THK-D57에 의한 인삼 사포닌의 생물학적 전환)

  • Yi, Eun-Ji;Lee, Jung-Min;Yi, Tae-Hoo;Cho, Seok-Cheol;Park, Yong-Jin;Kook, Moo-Chang
    • The Korean Journal of Food And Nutrition
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    • v.25 no.3
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    • pp.629-636
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    • 2012
  • Ginsenosides, ginseng saponin, are the principal components responsible for the pharmacological and biological activities of ginseng. In order to improve absorption and biological activities, the biotransformation of major ginsenoside to minor ginsenoside, as the more active compound, is required. In this study, we isolated Lactobacillus brevis THK-D57, which has high ${\beta}$-glycosidase activity, from Kimchi. The major ginsenoside Rb1 was converted to the minor ginsenoside 'compound K' during the fermentation of L. brevis THK-D57. The results propose that the biotransformation pathway to produce compound K is as follows: ginsenoside $Rb_1{\rightarrow}ginsenoside$ $Rd{\rightarrow}ginsenoside$ $F_2{\rightarrow}ginsenoside$ compound K.

High Performance Liquid Chromatographic Isolation of Ginsenoside $-Rf,\;-Rg_2\;and\;-Rh_1$ (고속액체(高速液體) Chromatography에 의(依)한 $Ginsenoside-Rf,\;Rg_2$$Rh_1$의 분리(分離))

  • Choi, Jin-Ho;Kim, Woo-Jung;Hong, Soon-Keun;Oh, Sung-Ki;Oura, Hikokichi
    • Applied Biological Chemistry
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    • v.23 no.4
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    • pp.206-210
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    • 1980
  • The minor components of $saponin-ginsenoside-Rf,\;-Rg_2\;and\;-Rh_1$ were isolated from Panax ginseng C.A. Meyer by preparative, semi-preparative and analtical high performance liquid chromatography. The rapid method developed in this work was proved to be very effective in separation and isolation of these minor ginsenosides. A further isolation was achieved by using the recycling technique.

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