• Korean Journal of Medicinal Crop Science
• /
• v.22 no.1
• /
• pp.23-31
• /
• 2014

This study was carried out to investigate change of ginsenoside contents in red and fresh ginseng according to root part and age by hydrolysis. Neutral total ginsenoside contents by hydrolysis in 6-year main root and lateral root were significantly increased than those by non-hydrolysis, as 41.6 and 32.8%, respectively. However, there was no significant difference in red ginseng. In fresh ginseng, ginsenoside contents of the protopanaxatriol group such as Re, Rf, $Rg_1$, $Rg_2$, and $Rh_1$ were not significantly different, but $Rb_1$, $Rb_2$, $Rb_3$, Rc, and Rd showed significant difference. The increase rate of neutral total ginsenoside content by hydrolysis was higher in epidermis-cortex than stele. Also, the neutral total ginsenoside content was fine root > rhizome > lateral root > main root, respectively. While there was no tendency towards the increase of ginsenoside by hydrolysis with the increase of root age in fine root and rhizome, there was significant decrease in main root and lateral root.

• Korean Journal of Pharmacognosy
• /
• v.47 no.1
• /
• pp.84-91
• /
• 2016

Korean ginseng (Panax ginseng C. A. Meyer) has been used as a traditional herbal medicine in East Asia and is very popular in the world, because of its health benefits. To comparison of pharmacological components and physiochemical properties between white and red ginseng from same body, we analyzed ginsenoside and malonyl ginsenoside, ash, crude lipid/protein, fatty acid, mineral contents, total/reducing sugar, and total phenolic and acidic polysaccharide contents. The general components did not show any significant difference between white and red ginseng. Whereas, the content of neutral ginsenoside $Rb_1$, $Rb_2$, Rc and Rd were higher in red ginseng than those of white ginseng. However, malonyl ginsenoside such as $m-Rb_1$, $m-Rb_2$, m-Rc and m-Rd in white ginseng were similar to neutral ginsenoside $Rb_1$, $Rb_2$, Rc and Rd in white ginseng and far higher than those of red ginseng. These results exhibit that malonyl ginsenosides were converted to neutral ginsenosides in steaming process for red ginseng. So, we suggest that malonyl ginsenoside are necessary to applies in ginsenoside analysis of Korean ginseng.

• Natural Product Sciences
• /
• v.20 no.2
• /
• pp.119-125
• /
• 2014

According to the results of my study on the chromatographic analysis of fresh ginseng (Panax ginseng C. A. Meyer) roots, most of the contents of protopanxadiol ginsenosides $Rb_1$, Rc, $Rb_2$, and Rd are derived from the corresponding malonyl ginsenosides in fresh ginseng by a heat process. Also, I confirmed that acetyl ginsenosides are naturally occurring constituents in fresh ginseng, not decarboxylates from malonyl ginsenosides. Seven neutral ginsenosides $Rg_1$, Re, Rf, Rc, $Rb_1$, $Rb_2$, and Rd were transformed to specific conversions in red ginseng preparation conditions. The conversion paths progress by three rules concluded from my study. These conversion rules are I: the ether bond is stable at positions 3 and 6 in the dammarane skeleton, II: the ether bond between sugars is stable in glycosides, and III: the ether bond to glycosides is unstable at position 20 in the dammarane skeleton.

• Archives of Pharmacal Research
• /
• v.27 no.1
• /
• pp.61-67
• /
• 2004

When ginseng water extract was incubated at $60^{\circ}C$ in acidic conditions, its protopanaxadiol ginsenosides were transformed to ginsenoside $Rg_3$ and ${\Delta}^{20}$-ginsenoside $Rg_3$. However, protopanaxadiol glycoside ginsenosides $Rb_1, Rb_2$ and Rc isolated from ginseng were mostly not transformed to ginsenoside $Rg_3$ by the incubation in neutral condition. The transformation of these ginsenosides to ginsenoside $Rg_3$ and ${\Delta}^{20}$-ginsenoside $Rg_3$ was increased by increasing incubation temperature and time in acidic condition: the optimal incubation time and temperature for this transformation was 5 h and $60^{\circ}C$ resepectively. The transformed ginsenoside $Rg_3$ and ${\Delta}^{20}$-ginsenoside $Rg_3$ were metabolized to ginsenoside $Rh_2$ and $\Delta^{20}$--ginsenoside $Rh_2$, respectively, by human fecal microflora. Among the bacteria isolated from human fecal microflora, Bacteroides sp., and Bifidobacterium sp. and Fusobacterium sp. potently transformed ginsenoside $Rg_3$ to ginsenoside $Rh_2$. Acid-treated ginseng (AG) extract, fermented AG extract, ginsenoside $Rh_2$ and protopanaxadiol showed potent cytotoxicity against tumor cell lines. AG extract, fermented AG extract and protopanaxadiol potently inhibited the growth of Helicobacter pylori.

• Journal of Ginseng Research
• /
• v.30 no.1
• /
• pp.1-7
• /
• 2006

Ceramide has been involved in celt death and acted as a lipid mediator of stress responses. Elevation of ceramide level was reported to occur in oxidative stress and lead to cell death in many cell types. This study was undertaken to elucidate a protective role of ginsenoside Rgl in cell death induced by oxidative stress. When LLC-PK1 cells were treated with $H_2O_2$ at a concentration of $400{\mu}M$ for 5 hr, cell death was observed and a released LDH activity indicative of cytotoxicity was Increased. $H_2O_2$ exposure to LLC-PK1 cells was shown to elevate the content of total ceramide by approximately 200% compared to control cells. Ceramide level was hypothesized to be a key to a reversal of cell death to survival. Ginsenoside Rgl at the concentrations ranging from 12.5 to $250{\mu}M$ protected LLC-PK1 cells from cell death induced by $H_2O_2\;at\;400{\mu}M$ for 5 hr, and decreased the ceramide level relative to $H_2O_2$. Ginsenoside Rgl inhibited neutral human ceramidase by 71% of controls, while sphingomyelinase was not inhibited. These results suggest that ginsenoside Rgl show the protection against cell death via the modulation of ceramide metabolism, and ceramide may be a promising therapeutic target for human diseases related to cell death.

• Journal of Ginseng Research
• /
• v.40 no.3
• /
• pp.245-250
• /
• 2016

Background: Ginsenosides are the major effective ingredients responsible for the pharmacological effects of ginseng. Malonyl ginsenosides are natural ginsenosides that contain a malonyl group attached to a glucose unit of the corresponding neutral ginsenosides. Methods: Medium-pressure liquid chromatography and semipreparative high-performance liquid chromatography were used to isolate purified compounds and their structures determined by extensive one-dimensional- and two-dimensional nuclear magnetic resonance (NMR) experiments. Results: A new saponin, namely malonyl-ginsenoside Re, was isolated from the fresh flower buds of Panax ginseng, along with malonyl-ginsenosides Rb1, Rb2, Rc, Rd. Some assignments for previously published $^1H$- and $^{13}C$-NMR spectra were found to be inaccurate. Conclusion: This study reports the complete NMR assignment of malonyl-ginsenoside Re, $Rb_1$, $Rb_2$, Rc, and Rd for the first time.

• Proceedings of the Ginseng society Conference
• /
• 2002.10a
• /
• pp.486-490
• /
• 2002

In different approaches ginsenosides were extracted from Korean ginseng roots by ammonia and for comparison with methanol-water and water. The extracts have been analyzed qualitatively and quantitatively to evaluate yield and selectivity of extractions of ginsenosides. Water supplied the lowest yield. The yields of extracts with liquid ammonia were higher than those with methanol-water. However, this is partly due to the conversion of malonyl ginsenoside to normal ginsenosides by ammonia. It was proved by HPLC that malonyl-ginsenosides $m-Rb_1,\;m-Rb_2,$ m-Rc and m-Rd were converted to the corresponding neutral ginsenosides. Furthermore, ginsenosides from ginseng roots were extracted by alkaline methanol-water $(60\%)$ solutions. Alternatively, the extracts of the methanol-water $(60\%)$ extraction were treated with sodium hydroxide solution. Both methods also convert the malonyl-ginsenosides to neutral ginsenosides.

• Journal of Ginseng Research
• /
• v.44 no.3
• /
• pp.424-434
• /
• 2020

Background: Amino acids are one of the major constituents in Panax ginseng, including neutral amino acid, acidic amino acid, and basic amino acid. However, whether these amino acids play a role in ginsenoside conversion during the steaming process has not yet been elucidated. Methods: In the present study, to elucidate the role of amino acids in ginsenoside transformation from fresh ginseng to red ginseng, an amino acids impregnation pretreatment was applied during the steaming process at 120℃. Acidic glutamic acid and basic arginine were used for the acid impregnation treatment during the root steaming. The ginsenosides contents, pH, browning intensity, and free amino acids contents in untreated and amino acid-treated P. ginseng samples were determined. Results: After 2 h of steaming, the concentration of less polar ginsenosides in glutamic acid-treated P. ginseng was significantly higher than that in untreated P. ginseng during the steaming process. However, the less polar ginsenosides in arginine-treated P. ginseng increased slightly. Meanwhile, free amino acids contents in fresh P. ginseng, glutamic acid-treated P. ginseng, and arginine-treated P. ginseng significantly decreased during steaming from 0 to 2h. The pH also decreased in P. ginseng samples at high temperatures. The pH decrease in red ginseng was closely related to the decrease in basic amino acids levels during the steaming process. Conclusion: Amino acids can remarkably affect the acidity of P. ginseng sample by altering the pH value. They were the main influential factors for the ginsenoside transformation. These results are useful in elucidating why and how steaming induces the structural change of ginsenoside inP. ginseng and also provides an effective and green approach to regulate the ginsenoside conversion using amino acids during the steaming process.

• Journal of Ginseng Research
• /
• v.48 no.4
• /
• pp.366-372
• /
• 2024

Background: The biological activity and pharmacological effects of rare ginsenosides have been proven to be superior to those of the major ginsenosides, but they are rarely found in ginseng. Methods: Ginsenoside Rb1 was chemically transformed with the involvement of methanol molecules by a synthesized heterogeneous catalyst 12-HPW@MeSi, which was obtained by the immobilization of 12-phosphotungstic acid on a mesoporous silica framework. High-performance liquid chromatography coupled with mass spectrometry was used to identify the transformation products. Results: A total of 18 transformation products were obtained and identified. Methanol was found to be involved in the formation of 8 products formed by the addition of methanol molecules to the C-24 (25), C-20 (21) or C-20 (22) double bonds of the aglycone. The transformation pathways of ginsenoside Rb1 involved deglycosylation, addition, elimination, cycloaddition, and epimerization reactions. These pathways could be elucidated in terms of the stability of the generated carbenium ion. In addition, 12-HPW@MeSi was able to maintain a 60.5% conversion rate of Rb1 after 5 cycles. Conclusion: Tandem and high-resolution mass spectrometry analysis allowed rapid and accurate identification of the transformation products through the characteristic fragment ions and neutral loss. Rare ginsenosides with methoxyl groups grafted at the C-25 and C-20 positions were obtained for the first time by chemical transformation using the composite catalyst 12-HPW@MeSi, which also enabled cyclic heterogeneous transformation and facile centrifugal separation of ginsenosides. This work provides an efficient and recyclable strategy for the preparation of rare ginsenosides with the involvement of organic molecules.

• Journal of Ginseng Research
• /
• v.43 no.1
• /
• pp.27-37
• /
• 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.