• Journal of Applied Biological Chemistry
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• 제62권4호
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• pp.375-384
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• 2019

고려인삼(Panax ginseng C.A. Meyer)을 70% EtOH 수용액으로 저온 추출한 뒤, 감압 농축한 추출물을SiO₂, ODS column chromatograph 및 중압분취(MPLC) 장비를 반복 실시하여 4종의 인삼 사포닌 화합물을 분리 및 정제하였다. NMR 및 고분해능 질량분석 장비를 이용하여 malonyl ginsenoside Rd (1), Rc (2), Rb2 (3), 및 Rb1 (4)로 구조 동정하였다. 분리한 4종의 화합물에 대하여 UPLC-MS/MS 질량분석기를 이용하여 수삼의 5년 및 6년근 뿌리의 동체를 정량분석 하였으며, malonyl ginsenoside의 총 함량의 합은 각각 6.62 및 2.34 mg/g으로 5년근이 약 2.8배 높은 것을 확인하였다. 인삼으로부터 분리된 화합물 중 malonyl ginsenoside Rd의 경우, 알코올에 의해 저해된 HepG2세포에 대해서 간세포를 보호하는 효과가 있음을 확인하였다.

• 생약학회지
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• 제48권1호
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• pp.82-87
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• 2017

Malonyl ginsenoside content of the Panax ginseng C.A. Meyer is known to account for 35% to 60% of total ginsenosides content. However, its distribution by ginseng part has not been studied. In this study, four kinds of malonyl ginsenosides were compared in Korean white ginseng part using the purified malonyl ginsenoside standards in our laboratory. White ginseng was prepared by the freeze drying ($-70^{\circ}C$, 48 h) or air drying ($50^{\circ}C$, 48 h) methods form 4-year-old ginseng. Malonyl ginsenoside content of main, lateral, and fine root, and of the main root without skin and its skin was compared. Malonyl ginsenosides (m-Rb1, m-Rb2, m-Rc and m-Rd) content (58%, 19.17 mg/g) in total ginsenosides of air dried white ginseng was decreased about 4% compared to its content of freeze dried white ginseng (62%, 20.40 mg/g). Malonyl ginsenoside content was the highest in fine root, compared to the main or lateral root. Malonyl ginsenosides content in skin of main root was 20.08 mg/g, while its content of the main root without skin was 2.58 mg/g. These results are expected to help establishment of quality specification and processing process in Korean white ginseng.

• 생약학회지
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• 제47권1호
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• pp.84-91
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• 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.

• Journal of Ginseng Research
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• 제40권3호
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• pp.245-250
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• 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.

• Natural Product Sciences
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• 제20권2호
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• pp.119-125
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• 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.

• Journal of Ginseng Research
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• 제40권4호
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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.

• 한국식품과학회지
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• 제33권3호
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• pp.282-287
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• 2001

인삼 조사포닌을 기존의 고온 MeOH 추출/n-BuOH 분획법 및 고온 MeOH 추출/Diaion HP-20 흡착/MeOH 용출법과 새로이 시도된 고온 MeOH 추출/cation AG 50W흡착/$H_2O$ 용출/n-BuOH 추출법(AG 50W법), 상온 MeOH 추출/Diaion HP-20 흡착/MeOH 용출법(상온추출법)과 EtOAc/n-BuOH 직접 추출법으로 분리한 다음 기존의 HPLC/RI 방법으로 ginsenoside조성을 비교한 결과 EtOAc/n-BuOH 직접 추출법을 제외하고는 큰 차이가 없었으나 분리능과 감도가 우수한 HPLC/ELSD방법을 사용한 결과, ginsenoside $Rb_2$, Rf, $Rg_1$ 및 $Rh_1$ 등을 뚜렷이 식별할 수 있었고 추출 및 분획방법에 따라 조사포닌간 ginsenoside의 현저한 조성차이를 볼 수 있었다. 특히 AG 50W법에 의해 분리된 조사포닌에서 뚜렷한 prosapogenin 피크를 볼 수 있었으며 LC/MS의 결과, ginsenoside $Rb_1$, $Rb_2$ 등의 7종의 주종 사포닌 이외에도 5종의 prosapogenin과 1종의 chikusetsusaponin을 포함한 총 13종의 ginsenoside를 동정하였다. 새로이 정립한 HPLC 분석조건, 즉 $NH_2$ 대신에 $C_{18}$ column을 사용하고 $KH_2PO_4/CH_3CN$ gradient로 상온추출법으로 분리한 조사포닌을 분석한 결과, malonyl ginsenoside 피크를 용이하게 확인할 수 있었다.

• 고려인삼학회:학술대회논문집
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• 고려인삼학회 2002년도 학술대회지
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• pp.486-490
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• 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
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• 제41권3호
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• pp.361-369
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• 2017

Background: The chemical constituents of Panax ginseng are changed by processing methods such as steaming or sun drying. In the present study, the chemical change of Panax ginseng induced by steaming was monitored in situ. Methods: Samples were separated from the same ginseng root by incision during the steaming process, for in situ monitoring. Sampling was sequentially performed in three stages; FG (fresh ginseng) ${\rightarrow}$ SG (steamed ginseng) ${\rightarrow}$ RG (red ginseng) and 60 samples were prepared and freeze dried. The samples were then analyzed to determine 43 constituents among three stages of P. ginseng. Results: The results showed that six malonyl-ginsenoside (Rg1, Rb1, Rb3, Rc, Rd, Rb2) and 15 amino acids were decreased in concentration during the steaming process. In contrast, ginsenoside-Rh1, 20(S)-Rg2, 20(S, R)-Rg3 and Maillard reaction product such as AF (arginine-fructose), AFG (arginine-fructose-glucose), and maltol were newly generated or their concentrations were increased. Conclusion: This study elucidates the dynamic changes in the chemical components of P. ginseng when the steaming process was induced. These results are thought to be helpful for quality control and standardization of herbal drugs using P. ginseng and they also provide a scientific basis for pharmacological research of processed ginseng (Red ginseng).

• Journal of Ginseng Research
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• 제44권2호
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• pp.215-221
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• 2020

Background: Panax ginseng has been used for a variety of medical purposes in eastern countries for more than two thousand years. From the extensive experiences accumulated in its long medication use history and the substantial strong evidence in modern research studies, we know that ginseng has various pharmacological activities, such as antitumor, antidiabetic, antioxidant, and cardiovascular system-protective effects. The active chemical constituents of ginseng, ginsenosides, are rich in structural diversity and exhibit a wide range of biological activities. Methods: Ginsenoside constituents from P. ginseng flower buds were isolated and purified by various chromatographic methods, and their structures were identified by spectroscopic analysis and comparison with the reported data. The 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H- tetrazolium bromide method was used to test their cytotoxic effects on three human cancer cell lines. Results: Six ginsenosides, namely 6'-malonyl formyl ginsenoside F₁ (1), 3β-acetoxyl ginsenoside F₁ (2), ginsenoside Rh₂₄ (6), ginsenoside Rh₂₅ (7), 7β-hydroxyl ginsenoside Rd (8) and ginsenoside Rh₂₆ (10) were isolated and elucidated as new compounds, together with four known compounds (3-5 and 9). In addition, the cytotoxicity of these isolated compounds was shown as half inhibitory concentration values, a tentative structure-activity relationship was also discussed based on the results of our bioassay. Conclusion: The study of chemical constituents was useful for the quality control of P. ginseng flower buds. The study on antitumor activities showed that new Compound 1 exhibited moderate cytotoxic activities against HL-60, MGC80-3 and Hep-G2 with half inhibitory concentration values of 16.74, 29.51 and 20.48 μM, respectively.