• Journal of Ginseng Research
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• 제37권4호
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• pp.457-467
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• 2013

A quick and simple method for simultaneous determination of the 30 ginsenosides (ginsenoside Ro, Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, 20(S)-Rg2, 20(R)-Rg2, 20(S)-Rg3, 20(R)-Rg3, 20(S)-Rh1, 20(S)-Rh2, 20(R)-Rh2, F1, F2, F4, Ra1, Rg6, Rh4, Rk3, Rg5, Rk1, Rb3, Rk2, Rh3, compound Y, compound K, and notoginsenoside R1) in Panax ginseng preparations was developed and validated by an ultra performance liquid chromatography photo diode array detector. The separation of the 30 ginsenosides was efficiently undertaken on the Acquity BEH C-18 column with gradient elution with phosphoric acids. Especially the chromatogram of the ginsenoside Ro was dramatically enhanced by adding phosphoric acid. Under optimized conditions, the detection limits were 0.4 to 1.7 mg/L and the calibration curves of the peak areas for the 30 ginsenosides were linear over three orders of magnitude with a correlation coefficients greater than 0.999. The accuracy of the method was tested by a recovery measurement of the spiked samples which yielded good results of 89% to 118%. From these overall results, the proposed method may be helpful in the development and quality of P. ginseng preparations because of its wide range of applications due to the simultaneous analysis of many kinds of ginsenosides.

• 고려인삼학회:학술대회논문집
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• 고려인삼학회 1998년도 Advances in Ginseng Research - Proceedings of the 7th International Symposium on Ginseng -
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• pp.115-126
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• 1998

Four new dammarnae-glycosides named ginsenosides Rgs, Rh4, RsB and Rf2 have been isolated 1'rom Korean red ginseng, the root of Panax ginseng C. A. Meyer (Araliaceae) and their chemical structures have been elucidated by chemical and spectroscopic methods, including'H-'H COSY, HMQC, HMBC, NOESY, as 3-0- [$\beta$-D-glucopyranosyl(1 ~2)-$\beta$-D-glucopyranosyl] dammar-20(22) , B4-diene-3P,12P-diol (ginsenoside Rgs),6-0-$\beta$-D-glucopyranosyl-dammar-20(22),24-diene-3P,6P, 12P-triol (ginsenoside Rh4),3-0- [6" -0-acetyl-D-glucopyranosyl(1 ~2)--D-glucopyranosyl] 20(5)- protopanaxadiol (ginsenoside Rs3) and 6-0- [u-L-rhamno-pyranosyl(1 ~2)-$\beta$-D-glucopyranosyl] dammarane -3$\beta$, 6a, 12 $\beta$, 20(R),25-pentol(ginsenoslde Rfa). The absolute stereo structure of a double bond at C-20(22) was determined as entgegen type by applying NOESY.OESY.

• Journal of Applied Biological Chemistry
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• 제62권4호
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• pp.315-322
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• 2019

Seasonal ginsenoside flux in the leaves of 5-year-old Panax ginseng was analyzed from the field-grown ginseng, for the first time, to study possible biosynthesis and translocation of ginsenosides. The concentrations of nine major ginsenosides, Rg1, Re, Rh1, Rg2, R-Rh1, Rb1, Rc, Rb2, and Rd, were determined by UHPLC during the growth in between April and November. It was confirmed total ginsenoside content in the dried ginseng leaves was much higher than the roots by several folds whereas the composition of ginsenosides was different from the roots. The ginsenoside flux was affected by ginseng growth. It quickly increased to 10.99±0.15 (dry wt%) in April and dropped to 6.41±0.14% in May. Then, it slowly increased to 9.71±0.14% in August and maintained until October. Ginsenoside Re was most abundant in the leaf of P. ginseng, followed by Rd and Rg1. Ginsenosides Rf and Ro were not detected from the leaf. When compared to the previously reported root data, ginsenosides in the leaf appeared to be translocated to the root, especially in the early vegetative stage even though the metabolite translocated cannot be specified. The flux of ginsenoside R-Rh1 was similar to the other (20S)-PPT ginsenosides. When the compositional changes of each ginsenoside in the leaf was analyzed, complementary relationship was observed from ginsenoside Rg1 and Re, as well as from ginsenoside Rd and Rb1+Rc. Accordingly, ginsenoside Re in the leaf was proposed to be synthesized from ginsenoside Rg1. Similarly, ginsenosides Rb1 and Rc were proposed to be synthesized from Rd.

• Journal of Ginseng Research
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• 제37권1호
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• pp.124-134
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• 2013

The authentication of the physico-chemical properties of ginsenosides reference materials as well as qualitative and quantitative batch analytical data based on validated analytical procedures is a prerequisite for certifying good manufacturing practice (GMP). Ginsenoside Rb1 and Rg1, representing protopanaxadiol and protopanaxatriol ginsenosides, respectively, are accepted as marker substances in quality control standards worldwide. However, the current analytical methods for these two compounds recommended by Korean, Chinese, European, and Japanese pharmacopoeia do not apply to red ginseng preparations, particularly the extract, because of the relatively low content of the two agents in red ginseng compared to white ginseng. In manufacturing fresh ginseng into red ginseng products, ginseng roots are exposed to a high temperature for many hours, and the naturally occurring ginsenoside Rb1 and Rg1 are converted to artifact ginsenosides such as Rg3, Rg5, Rh1, and Rh2 during the heating process. The analysis of ginsenosides in commercially available ginseng products in Korea led us to propose the inclusion of the (20S)- and (20R)-ginsenoside Rg3, including ginsenoside Rb1 and Rg1, as additional reference materials for ginseng preparations. (20S)- and (20R)-ginsenoside Rg3 were isolated by Diaion HP-20 adsorption chromatography, silica gel flash chromatography, recrystallization, and preparative HPLC. HPLC fractions corresponding to those two ginsenosides were recrystallized in appropriate solvents for the analysis of physico-chemical properties. Documentation of those isolated ginsenosides was achieved according to the method proposed by Gaedcke and Steinhoff. The ginsenosides were subjected to analyses of their general characteristics, identification, purity, content quantification, and mass balance tests. The isolated ginsenosides showed 100% purity when determined by the three HPLC systems. Also, the water content was found to be 0.534% for (20S)-Rg3 and 0.920% for (20R)-Rg3, meaning that the net mass balances for (20S)-Rg3 and (20R)-Rg3 were 99.466% and 99.080%, respectively. From these results, we could assess and propose a full spectrum of physico-chemical properties of (20S)- and (20R)-ginsenoside Rg3 as standard reference materials for GMP-based quality control.

• 대한한의학방제학회지
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• 제30권3호
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• pp.175-182
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• 2022

Objective : This study aims to investigate the active ingredients and potential mechanisms of the beneficial herb on human cancers such as the liver by employing network pharmacology. Methods : Ingredients and their target information was obtained from various databases such as TM-MC, TTD, and Drugbank. Related protein for liver cancer was retrieved from the Comparative Toxicogenomics Database and literature. A hypergeometric test and gene set enrichment analysis were conducted to evaluate associations between protein targets of red ginseng (Panax ginseng C. A. Meyer) and liver cancer-related proteins and identify related signaling pathways, respectively. Network proximity was employed to identify active ingredients of red ginseng on liver cancer. Results : A compound-target network of red ginseng was constructed, which consisted of 363 edges between 53 ingredients and 121 protein targets. MAPK signaling pathway, PI3K-Akt signaling pathway, p53 signaling pathway, TGF-beta signaling pathway, and cell cycle pathway was significantly associated with protein targets of red ginseng. Network proximity results indicated that Ginsenoside Rg1, Acetic Acid, Ginsenoside Rh2, 20(R)-Ginsenoside Rg3, Notoginsenoside R1, Ginsenoside Rk1, 2-Methylfuran, Hexanal, Ginsenoside Rd, Ginsenoside Rh1 could be active ingredients of red ginseng against liver cancer. Conclusion : This study suggests that network-based approaches could be useful to explore potential mechanisms and active ingredients of red ginseng for liver cancer.

• 한국식품저장유통학회지
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• 제20권4호
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• pp.573-582
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• 2013

본 연구에서는 ${\beta}$-glucosidase 활성이 있는 유산균주를 이용하여 발효인삼의 ginsenoside 유용 유도체의 전환 검토 및 품질특성 알아보고자 하였다. ${\beta}$-glucosidase 활성 유산균주를 검색하여 인삼 및 홍삼 발효에 따른 TLC 패턴, ginsenoside 함량 변화, 총 페놀성 화합물 함량, 전자공여능 및 총당 함량을 분석하였다. $37^{\circ}C$에서 65시간 발효 후 Rg2r, Rh2s, Rh2r은 모두 불검출되었으며, 인삼 및 홍삼 추출물 발효에서 발효전과 비교하여 Rg1, Re는 감소한 반면, Rh1, Rg2s, Rd, Rg3r, Rg3s는 발효 후 모두 증가한 것으로 나타났다. 홍삼에서 대표적인 성분으로 알려져 있는 Rg3의 경우 홍삼액 발효전 $104.56{\mu}g/mL$에서 발효 후 균주 종류에 따라 $114.83{\sim}131.68{\mu}g/mL$으로 증가하였다. 7일간 발효 후 홍삼액의 총 페놀성 화합물 및 전자공여능은 일부 균주에서는 발효전과 비교하여 감소하다가 다시 증가하는 경향을 나타내기도 하였으나, 발효가 0~7일차까지 진행됨에 따라 전반적으로 약간 감소되는 경향을 나타내었다. 전자공여능은 인삼 추출물 발효액은 발효 후 균주 종류에 따라 증가하는 경향을 보였으나, 홍삼 추출액은 발효 후 낮아지는 경향을 보였다. 인삼 및 홍삼 추출액을 첨가하여 유산균주별로 발효를 실시한 결과 총당 함량은 발효에 따라 감소하는 것으로 나타났다.

• Journal of Ginseng Research
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• 제35권1호
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• pp.60-68
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• 2011

The chemical and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity changes of ginsenoside $Rb_1$-glycine and ginsenoside $Rg_1$-glycine mixtures by Maillard reaction were investigated to identify the role of Maillard reaction in the increased antioxidant activity of ginseng by heat-processing. The DPPH radical scavenging activity of $Rg_1$-glycine mixture was more strongly increased by heat-processing than that of $Rb_1$-glycine mixture. From the analyses of ginsenosides, $Rb_1$ was gradually changed into 20(S)-$Rg_3$, 20(R)-$Rg_3$, $Rk_1$ and $Rg_5$ by heat-processing. $Rg_1$ was gradually changed into 20(S)-$Rh_1$, 20(R)-$Rh_1$, $Rk_3$ and $Rh_4$ by heat-processing. However, the generation of these less-polar ginsenosides was not related to the increased DPPH radical scavenging activity of $Rb_1$-glycine and $Rg_1$-glycine mixtures because their DPPH radical scavenging activities were already significantly increased when dried at $50^{\circ}C$, which temperature induce no structural changes of ginsenosides. In the comparison of browning compound levels of $Rg_1$-glycine and $Rb_1$-glycine mixtures, the extents of Maillard reaction were positively correlated with their increased free radical scavenging activities. Based on the chemical and DPPH radical scavenging activity changes of $Rg_1$-glycine and $Rb_1$-glycine mixtures by heat-processing, we clearly identified that the increased free radical scavenging activity of ginsenoside is mediated by the Maillard reaction between sugar moiety of ginsenoside and amino acid.

• Journal of Ginseng Research
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• 제47권2호
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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.

• 한국약용작물학회지
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• 제21권5호
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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.

• Journal of Ginseng Research
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• 제37권4호
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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.