• Title/Summary/Keyword: ginsenoside hydrolysis

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Studies on the Manufacturing of Ginseng Soft Drink II. Effect of pH and heat treatment on the stability of panaxadiol saponins (인삼청량음료 제조에 관한 연구 (제2보) pH 및 처리조건이 Panaxadiol Saponin의 안정성에 미치는 영향)

  • 양재원;도재호
    • Journal of Ginseng Research
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    • v.6 no.1
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    • pp.25-29
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    • 1982
  • This investigation was carried out to study the influence of pH and heat treatment on the ginsenosides in the white ginseng extract. Changes in ginsenosides (Rb1, Rb2, ,Rc, Rd) and free sugar were measured by the peak area variation of HPLC chromatogram during 25 hours heat treatment at the various level of pH. It was found that :(1) The peak areas of Rb1. Rb2, Rc and Rd on the HPLC chromatogram were decreased remarkably below pH 4.0 and more decrease was found as the temperature and heating time increased. (2) Those of glucose and arabinose were increased remarkably. It is considrered that the increase of glucose and the formation of arabinose result from the hydrolysis of ginsenoside( Rb1, Rb2, Rc, Rd) linked with sugars.

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Bioconversion of Ginsenosides in Red Ginseng Extract by Saccharomycescerevisiae and Saccharomyces carlsbergensis (홍삼농축액에서 Saccharomyces cerevisiae와 Saccharomyces carlsbergensis에 의한 Ginsenosides의 bioconversion)

  • Jang, Mi;Min, Jin-Woo;Kim, Ju-Han;Kim, Se-Young;Yang, Deok-Chun
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2010.05a
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    • pp.16-16
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    • 2010
  • Ginseng(Panax ginseng C.A. Meyer) is reported to have many pharmaceutical activities. The minor ginsenosides(Rd, Rg3, Rh2 and compound K) display pharmaceutical properties superior to those of the major ginsenosides. These minor ginsenosides, which contribute a very small percentage, are produced by hydrolysis of the sugar moieties of the major ginsenosides. The pH of red ginseng extracts fermented with S. cerevisiae and S. carlsbergensis decreased rapidly during 3 days of fermentation, with no further significant change thereafter. After 20 days of fermentation, a relatively small difference remained in the acidity of extracts fermented with S. cerevisiae (0.54%) and S. carlsbergensis (0.58%). Reducing sugar in the S. cerevisiae and S. carlsbergensis extracts decreased from 25.86 to 4.54 mg/ml and 4.32 mg/ml glucose equivalents, respectively; and ethanol contents increased from 1.5% at day 0 to 16.0 and 15.0%, respectively, at 20 days. Ginsenosides Rb1, Rb2, Rc, Re, Rf, and Rg1 decreased during the fermentation with S. cerevisiae, but Rd and Rg3 increased by 12 days. Ginsenosides Rb1, Rb2, Rc, Re and Rg1 decreased gradually in the extract with S. carlsbergensis, but Rd and Rg3 were increased at 6 days and 9 days.

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Multicomponent assessment and ginsenoside conversions of Panax quinquefolium L. roots before and after steaming by HPLC-MSn

  • Huang, Xin;Liu, Yan;Zhang, Yong;Li, Shuai-Ping;Yue, Hao;Chen, Chang-Bao;Liu, Shu-Ying
    • Journal of Ginseng Research
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    • v.43 no.1
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    • pp.27-37
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    • 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.

Characteristics of Functional Components of Red Ginseng Concentrate First Extracted at Low Temperature I - Focused on Ginsenoside - (저온에서 1차 추출한 홍삼농축액의 기능성분 특성 I - Ginsenoside 위주로 -)

  • Su Hyun Lee;Keon Shin;Seon Yeung Jo;Young Sig Park
    • Journal of Food Hygiene and Safety
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    • v.38 no.3
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    • pp.176-183
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    • 2023
  • The extraction and filtration of red ginseng with a mixed solvent of water and alcohol-a common processing method-and the production of a concentrate through heat treatment, such as steaming, leads to its hydrolysis or polymerization. Approximately 200 ginsenosides have consequently been detected in small amounts, in addition to the identification of the functions of approximately 30 major ginsenosides. This complicates the identification of the functionality of red ginseng and its efficacy, and has negative effects as a functional food, as the astringent taste becomes stronger with an increase in the number of extractions. The red ginseng concentrate was, therefore, extracted at a low temperature (less than 40 ℃) and processed to eliminate these negative aspects, with a specific focus on the characteristics of the functional components of ginsenosides.

Qualitative and quantitative analysis of the saponins in Panax notoginseng leaves using ultra-performance liquid chromatography coupled with time-of-flight tandem mass spectrometry and high performance liquid chromatography coupled with UV detector

  • Liu, Fang;Ma, Ni;He, Chengwei;Hu, Yuanjia;Li, Peng;Chen, Meiwan;Su, Huanxing;Wan, Jian-Bo
    • Journal of Ginseng Research
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    • v.42 no.2
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    • pp.149-157
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    • 2018
  • Background: Panax notoginseng leaves (PNL) exhibit extensive activities, but few analytical methods have been established to exclusively determine the dammarane triterpene saponins in PNL. Methods: Ultra-performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC/Q-TOF MS) and HPLC-UV methods were developed for the qualitative and quantitative analysis of ginsenosides in PNL, respectively. Results: Extraction conditions, including solvents and extraction methods, were optimized, which showed that ginsenosides Rc and Rb3, the main components of PNL, are transformed to notoginsenosides Fe and Fd, respectively, in the presence of water, by removing a glucose residue from position C-3 via possible enzymatic hydrolysis. A total of 57 saponins were identified in the methanolic extract of PNL by UPLC/Q-TOF MS. Among them, 19 components were unambiguously characterized by their reference substances. Additionally, seven saponins of PNL-ginsenosides Rb1, Rc, Rb2, and Rb3, and notoginsenosides Fc, Fe, and Fd-were quantified using the HPLC-UV method after extraction with methanol. The separation of analytes, particularly the separation of notoginsenoside Fc and ginsenoside Rc, was achieved on a Zorbax ODS C8 column at a temperature of $35^{\circ}C$. This developed HPLC-UV method provides an adequate linearity ($r^2$ > 0.999), repeatability (relative standard deviation, RSD < 2.98%), and inter- and intraday variations (RSD < 4.40%) with recovery (98.7-106.1%) of seven saponins concerned. This validated method was also conducted to determine seven components in 10 batches of PNL. Conclusion: These findings are beneficial to the quality control of PNL and its relevant products.

Effects of Ginseng Berry Water Extract on the Polysaccharide Hydrolysis of Extracellular Enzymes and Intracellular PTP1B and AKT1 (진생베리 열수 추출물의 다당체 분해 효소와 인슐린 신호전달 분자 PTP1B와 AKT1에 미치는 효과)

  • Kwon, Eun-Jeong;Hong, Sugyeong;Kim, Moon-Moo;Kim, Joo Wan;Kim, Deok Won;Chung, Kyung Tae
    • Journal of Life Science
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    • v.24 no.9
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    • pp.1006-1011
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    • 2014
  • Ginseng has been known to be highly effective for health as a traditional medicinal herb. Ginseng berry, or fruit of ginseng, contains ginsenoside, saponin, polyphenol, polyacetylene, alkaloid, etc. as the main compounds as does ginseng. The aim of this study is to evaluate any effect of ginseng berry water extract (GBE) on diabetic-associated molecules, such as enzymes, which are responsible for the glucose entry of the cells and the insulin receptor signaling molecules using HepG2 cells. Therefore, two enzymes, ${\alpha}$-amylase and ${\alpha}$-glucosidase, were selected and assayed for their activities in the presence of GBE in vitro. These two enzymes are responsible for producing glucose from dietary starch. Protein-tyrosine phosphatase 1B (PTP1B) and Akt1 are key proteins in the insulin receptor signaling pathway. These two intracellular signaling molecules were investigated for their expression levels in HepG2 cells after insulin and GBE treatment. GBE, at concentrations up to $1,000{\mu}g/ml$, did not exert any inhibitory effect on ${\alpha}$-amylase and ${\alpha}$-glucosidase. It was observed that the expression level of PTP1B was increased by insulin and the $25{\mu}g/ml$ GBE treatment enhanced the PTP1B level. However, GBE at a concentration of $200{\mu}g/ml$ reduced the expression level of PTP1B. In the case of Akt1, the Akt1 level by insulin was decreased by GBE treatment. These data suggest that the water extracts of ginseng berry have an influence on intracellular signaling by insulin.

Property and Inhibition of the Hydrolysis of Ginseng Saponins by Organic Acids Neutralization in Ginseng Extract Preparations (인삼(人蔘)의 가열추출(加熱抽出) 과정(過程) 중 사포닌의 가수분해(加水分解) 특성(特性) 및 유기산중화(有機酸中和)에 의한 분해억제(分解抑制))

  • Jeong, Seung-Ii;Lee, Yong-Gu;Kim, Cheon-Suk;Lee, Seong
    • Korean Journal of Medicinal Crop Science
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    • v.6 no.4
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    • pp.305-310
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    • 1998
  • Glucosidic bond at the $C_{20}$ position of the sapogenins was hydrolyzed easily in the lower pH, higher temperature and longer time to give prosapogenins and sugars. The glucosidic bond of saponin at the $C_3\;of\; ginsenoside-Rb_1\;$, which is secondary carbon, was relatively stable due to the low electron density of -0.2. But the bond of saponin at the $C_{20}$ position, which is tertiary carbon with the relatively high electron density of -0.3, was liable to be hydrolyzed even in weak acidic solution by the increase of heating time. On the other hand, fresh and white ginseng contained 4.12 mg/g, 13.05 mg/g of citric acid, 0.68 mg/g, 2.18 mg/g of malonic acid, 1.13 mg/g, 3.68 mg/g of oxalic acid, 2.68 mg/g, 8.62 mg/g of malic acid and 0.13 mg/g, 0.46 mg/g of succinic acid, respectively. Ginseng saponins were very stable in ginseng extract neutralized with sodium carbonate or sodium bicarbonate corresponding to the equivalent amount of the total organic acid in the ginseng.

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Recent Studies on the Chemical Constituents of Korean Ginseng (Panax ginseng C. A. Meyer) (고려인삼의 화학성분에 관한 고찰)

  • 박종대
    • Journal of Ginseng Research
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    • v.20 no.4
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    • pp.389-415
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    • 1996
  • Panax ginseng C.A. Meyer(Araliaceae) has been traditionally used as an expensive and precious medicine in oriental countries for more than 5, 000 years. Ginseng saponin isolated from the root of Panax ginseng have been regarded as the main effective components responsible for the pharmacological and biological activities. Such as antiaging effects. antidiabetic effects anticancer effects. Protection against physical and chemical stress. Analgesic and antipyretic effects. Effects on the central nervous system, tranquilizing action and others. Thirty kinds of ginsenosides have been so far isolated from ginseng saponin and their chemical structures have been elucidated since 1960's. Among which protopanaxadiol type is 19 kinds. protopanaxatriol type. 10 kinds and oleanane type, one. Since ginsenosides are generally labile under acidic conditions ordinary acid hydrolysis is always accompanied by many side reactions, such as epimerization. hydroxylation and cyclization of side chain of the sapogenins Especially. it is well known that C-20 glycosyl linkage of ginsenoside was hydrolysed on heating with acetic acid to give an equilibrated mixture of 20(S) and 20(R) epimers. And also, the chemical transformations of the secondary metabolites have appeared during the steaming process to prepare red ginseng. Indicating demalonylation of malonyl ginsenosides, elimination of glycosyl residue at C-20 and isomerization of hydroxyl configuration at C-20. But these studies have not provided a comprehensive picture in explaning how these ginsenosides showed val'iotas pharmacological activities of ginseng. Though some of them have been involved in the mechanism of pharmacological actions. Recently, non-saponin components have received a great deal of attention for their antioxidant, anticancer antidiabetic, immunomodulating. anticomplementary activities and so on. To meet the demand for such wide applications, studies on the non-saponin components play an important role in providing a good evidence of pharmacological and biol ogical activities. Among the non-saponin constituents of Korean ginseng, polyacetylenes, phenols. Sesquiterpenes, alkaloids. polysaccharides oligosaccharides, oligopeptides and aminoglycosides together with ginsenosides of terrestrial part are mainly described.

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Effect of hydrothermal processing on ginseng extract

  • Ryu, Jebin;Lee, Hun Wook;Yoon, Junho;Seo, Bumjoon;Kwon, Dong Eui;Shin, Un-Moo;Choi, Kwang-joon;Lee, Youn-Woo
    • Journal of Ginseng Research
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    • v.41 no.4
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    • pp.572-577
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    • 2017
  • Background: Panax ginseng Meyer is cultivated because of its medicinal effects on the immune system, blood pressure, and cancer. Major ginsenosides in fresh ginseng are converted to minor ginsenosides by structural changes such as hydrolysis and dehydration. The transformed ginsenosides are generally more bioavailable and bioactive than the primary ginsenosides. Therefore, in this study, hydrothermal processing was applied to ginseng preparation to increase the yields of the transformed ginsenosides, such as 20(S)-Rg3, Rk1, and Rg5, and enhance antioxidant activities in an effective way. Methods: Ginseng extract was hydrothermally processed using batch reactors at $100-160^{\circ}C$ with differing reaction times. Quantitative analysis of the ginsenoside yields was performed using HPLC, and the antioxidant activity was qualitatively analyzed by evaluating 2,2'-azino-bis radical cation scavenging, 2,2-diphenyl-1-picrylhydrazyl radical scavenging, and phenolic antioxidants. Red ginseng and sun ginseng were prepared by conventional steaming as the control group. Results: Unlike steaming, the hydrothermal process was performed under homogeneous conditions. Chemical reaction, heat transfer, and mass transfer are generally more efficient in homogeneous reactions. Therefore, maximum yields for the hydrothermal process were 2.5-25 times higher than those for steaming, and the antioxidant activities showed 1.6-4-fold increases for the hydrothermal process. Moreover, the reaction time was decreased from 3 h to 15-35 min using hydrothermal processing. Conclusion: Therefore, hydrothermal processing offers significant improvements over the conventional steaming process. In particular, at temperatures over $140^{\circ}C$, high yields of the transformed ginsenosides and increased antioxidant activities were obtained in tens of minutes.