• 제목/요약/키워드: Epimers

검색결과 16건 처리시간 0.021초

Quantitative Determination of Amygdalin Epimers from Armeniacae Semen by High Performance Liquid Chromatography.

  • Koo, Ja-Yong;Hwang, Eun-Young;Lee, Je-Hyun;Hong, Seon-Pyo
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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    • pp.223.1-223.1
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    • 2003
  • D-Amygdalin and its conversion product, neoamygdalin, were clearly separated on reverse-phase column chromatography by an optimized eluent of 10 mM sodium phosphate buffer (pH 3.5) containing 8.5% acetonitrile. Linearity for analyzing D-amygdalin and neoamygdalin was observed in the range from 0.05 to 0.5 mM. The detection limits for D-amygdalin and neoamygdalin were ca. 5 uM per injected amount. When extracting amygdalin from a whole piece of Armeniacae Semen in the boiling aqueous solution, there was almost no influence of emulsin; it resulted in higher extraction yield. (omitted)

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

  • 박종대
    • Journal of Ginseng Research
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    • 제20권4호
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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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Stereospecific anticancer effects of ginsenoside Rg3 epimers isolated from heat-processed American ginseng on human gastric cancer cell

  • Park, Eun-Hwa;Kim, Young-Joo;Yamabe, Noriko;Park, Soon-Hye;Kim, Ho-Kyong;Jang, Hyuk-Jai;Kim, Ji Hoon;Cheon, Gab Jin;Ham, Jungyeob;Kang, Ki Sung
    • Journal of Ginseng Research
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    • 제38권1호
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    • pp.22-27
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    • 2014
  • Background: Research has been conducted with regard to the development of methods for improving the pharmaceutical effect of ginseng by conversion of ginsenosides, which are the major active components of ginseng, via high temperature or high-pressure processing. Methods: The present study sought to investigate the anticancer effect of heat-processed American ginseng (HAG) in human gastric cancer AGS cells with a focus on assessing the role of apoptosis as an important mechanistic element in its anticancer actions. Results and Conclusion: HAG significantly reduced the cancer cell proliferation, and the contents of ginsenosides Rb1 and Re were markedly decreased, whereas the peaks of less-polar ginsenosides [20(S,R)-Rg3, Rk1, and Rg5] were newly detected. Based on the activity-guided fractionation of HAG, ginsenoside 20(S)-Rg3 played a key role in inducing apoptosis in human gastric cancer AGS cells, and it was generated mainly from ginsenoside Rb1. Ginsenoside 20(S)-Rg3 induced apoptosis through activation of caspase-3, caspase-8, and caspase-9, as well as regulation of Bcl-2 and Bax expression. Taken together, these findings suggest that heat-processing serves as an increase in the antitumor activity of American ginseng in AGS cells, and ginsenoside 20(S)-Rg3, the active component produced by heat-processing, induces the activation of caspase-3, caspase-8, and caspase-9, which contributes to the apoptotic cell death.

Chemical transformation and target preparation of saponins in stems and leaves of Panax notoginseng

  • Wang, Ru-Feng;Li, Juan;Hu, Hai-Jun;Li, Jia;Yang, Ying-Bo;Yang, Li;Wang, Zheng-Tao
    • Journal of Ginseng Research
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    • 제42권3호
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    • pp.270-276
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    • 2018
  • Background: Notoginsenoside Ft1 is a promising potential candidate for cardiovascular and cancer disease therapy owing to its positive pharmacological activities. However, the yield of Ft1 is ultralow utilizing reported methods. Herein, an acid hydrolyzing strategy was implemented in the acquirement of rare notoginsenoside Ft1. Methods: Chemical profiles were identified by ultraperformance liquid chromatography coupled with quadruple-time-of-flight and electrospray ionization mass spectrometry (UPLC-Q/TOF-ESI-MS). The acid hydrolyzing dynamic changes of chemical compositions and the possible transformation pathways of saponins were monitored by ultrahigh-performance LC coupled with tandem MS (UHPLC-MS/ MS). Results and conclusion: Notoginsenoside Ft1 was epimerized from notoginsenoside ST4, which was generated through cleaving the carbohydrate side chains at C-20 of notoginsenosides Fa and Fc, and vinaginsenoside R7, and further converted to other compounds via hydroxylation at C-25 or hydrolysis of the carbohydrate side chains at C-3 under the acid conditions. High temperature contributed to the hydroxylation reaction at C-25 and 25% acetic acid concentration was conducive to the preparation of notoginsenoside Ft1. C-20 epimers of notoginsenoside Ft1 and ST4 were successfully separated utilizing solvent method of acetic acid solution. The theoretical preparation yield rate of notoginsenoside Ft1 was about 1.8%, which would be beneficial to further study on its bioactivities and clinical application.

약산성 다당의 선택적 분해 과정에서 얻어진 특이당 함유 Oligo당의 구조적 분석 (Structural Analysis of the Unusual Sugar-Containing Oligosaccharides Formed by the Selective Cleavage of Weakly Acidic Polysaccharide)

  • 신광순;이호
    • 한국식품과학회지
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    • 제29권6호
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    • pp.1105-1112
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    • 1997
  • 약산성 다당 GL-4IIb2'에 대해 연속적 부분 산가수 분해 과정을 거쳐, 2종의 oligo당 획분 PA-2' 및 PA-1-III를 분리하고 그들의 구조분석을 행하였다. PA-2'는 주요 구성당으로 Rha 와 특이당 Kdo를 동일한 비율로 함유하고 있었으며, permethylated oligosaccharide-alditol로 전환시켜, GC-MS로 분석한 결과, m/z 189$(bA_1)$및 m/z 308 $(aJ_2)$에서 6-deoxyhexose와 Kdo에 기인하는 fragment ion이 관찰되었다. 이 peak는 m/z 162에서 특징적인 ion을 나타낸 반면 m/z 177 ion이 관찰되지 않음으로써 Kdo의 C4위치가 아닌 C5위치가 치환되어 있음을 알 수 있었다. 한 methyl화 분석 결과, PA-2'은 환원말단 Rhap와 5-substituted Kdo가 높은 비율로 검출되었으며 환원 형태의 PA-2'를 대상으로 $^1M-NMR$ 분석을 하였을 때 ${\delta}$ 5.09 ppm에서 ${\alpha}-L-Rha$의 anomeric proton에 기인한 단일 signal이 관찰되었다. 이상의 결과로 부터 PA-2'는 주로 ${\alpha}-L-Rhap-(1{\rightarrow}5)-Kdo$로 구성되었다는 사실을 알 수 있었다 한편. PA-1-III는 소량의 Ara 믹 Dha와, 다량의 Rha 및 Kdo가 주요 구성당으로 나타났으며, PA-1-III 획분의 permethylated oligosaccharide-alditol 유도체는 GC상에서 3개의 peak (1P, 2P 및 3P)로 분리되었다. 이들의 MS 분석 결과, 높은 비율로 검출된 1P는 $Rhap-(1{\rightarrow}5)-Kdo$의 구조로 나타났으며 반면 낮은 비율의 2P및 3P는 $Araf-(1{\rightarrow}5)-Dha$의 동일구조를 갖는 것으로 확인되었는데 이는 Dha의 carbonyl 환원과정 중 생성된 epimer로 판단되었다.

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LC-MS/MS를 이용한 식품 중 맥각 알칼로이드 시험법 개발 (Development of Analytical Method for Ergot Alkaloids in Foods Using Liquid Chromatoraphy-Tandem Mass Spectrometry)

  • 천소영;정은아;이봄내;권진욱;박혜영;김신희;강길진
    • 한국식품위생안전성학회지
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    • 제34권2호
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    • pp.158-169
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    • 2019
  • 우리나라의 해외 곡류 수입량과 수입국가의 다변화를 고려 해 볼 때, 호밀, 밀, 귀리 등 맥류에서 주로 발생하는 것으로 알려져 있는 맥각알칼로이드의 노출가능성도 배제할 수 없다. 따라서 본 연구는 곡류 및 곡류가공품 중 맥각알칼로이드에 대한 선제적 안전관리를 위해 호밀 및 가공품 (크래커, 맥주) 으로 부터 에르고메트린을 포함한 12종 맥각알칼로이드의 공인 시험법을 개발하고자 하였다. 아세토니트릴이 함유된 2 mM 탄산암모늄용액 추출과 Mycocep catridge를 이용한 정제 농축이 전처리 방법으로 적합함이 확인되었고, 기기분석을 통해 표준물질 첨가 검량선의 직선성이 12개 알칼로이드 모두 $R^2$ >0.99 이상이었으며, 정량한계는 $0.01{\sim}0.05{\mu}g/kg$수준이었다. 시험법 검증을 통해 대상 품목간의 차이는 있으나, 12개 맥각 알칼로이드 모두 회수율은 72~113% 수준이었으며, 반복성은 2~10% 수준으로 적합성이 확인되었다.