• 제목/요약/키워드: C-glycosides

검색결과 183건 처리시간 0.023초

한국인삼론(韓國人蔘論) (Current Status of Korean Ginseng Research)

  • 한병훈
    • 생약학회지
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    • 제3권3호
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    • pp.151-160
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    • 1972
  • Recent achievements of scientific research on the pharmacologic activities and the chemical problems of dammalene glycosides, which are considered to be effective principles of Korean ginseng, are reviewed and analyzed in view of structure-activity relationship. 1) S. Shibata and his co-workers detected 12 glycoside spots of dammalene series on the two dimensional T.L.C. of total glycoside fraction from Japanese ginseng, and designated them Ginsenoside Rx(x=a, b, c, g, h, etc.) in the order of increasing Rf-value. The aglycones of those glycosides were characterized to be protopanaxadiol for the Ginsenoside $Rx(x=a,\;b_{1},\;b_{2},\;c,\;d,\;e,\;f)$ and protopanaxatriol for the Ginsenoside $Rx(x=g_{1},\;g_{2},\;g_{3},\;h_{1}\;'h_{2})$. Using Korean ginseng as the material for our study, the author and his coworkers isolated a new dammalene glycoside(Panax Saponin C), which comes under the category of protopanaxadiol glycosides based on the classification of S. Shibata et al., and characterized this saponin to be the glycoside of protopanaxatriol series. Furthermore, Panax Saponin C dissociated into $two\;components(C_{1}\;and\;C_{2}-acetate)$ by acetylation, both of which returned to original Panax Saponin C by deacetylation. Based on this result, more than 13 glycoside components of dammalene series will be expected in the Korean ginseng. 2) The structures of protopanaxadiol and protopanaxatriol, the genuine aglycones of dammalene glycosides, are fully established to be structural analogues by S. Shibata and his co-workers, therefore antagonistic and/or analogical activities will be expected for the pharmacologic activities of these glycoside series of structural analogues. K. Takaki and his co-workers found central nervous system (CNS) stimmulant activity from the glycosides of protopanaxatriol series and CNS-depressant activity from the glycosides of protopanaxadiol series. On the other hand, the author and his co-workers found stimmulating activity on the protein synthesis from both the series of dammalene glycosides with delayed and long-lasting characteristics. This delayed and long-lasting characteristics were also observed in the anti-inflammatory activity of glycosides of protopanaxatriol series on their time course tendency. For the convenience's sake of argument, pluralistic pharmacologic activities of dammalene glycosides, which were observed by many workers at various pharmacologic site, may be classified into two main categories; one is pan-cellular activity and the other is organ specific activity to the certain tissue which is a mass of cells differentiated to a certain direction for their special functions in the body. Based on the data of K. Takaki and those of the authors, following assumption will be probable; Pharmacologic activities of both series of glycosides of protopanaxadiol and protopanaxatriol aglycones may be antagonistic on their tissue-specific activities and analogic on their pan-cellular activities. Therefore, the mixture of these two series of glycosides in an appropriate ratio, as the case of total extract of Korean ginseng, will be probably beneficial to the host by increasing the synthesis of some functional proteins, due to the additive action of pan-cellular activity, and with the disappearance of any significant behavioral symptoms due to the antagonism of tissue specific activity. This fact will probably be the main reason why classical trials of pharmacologists failed in re-discovering the efficacy of Korean ginseng with their behavioral test. 3) The author and his co-workers achieved the synthesis of $C^{14}-labelled\;Panax\;Saponin\;A\;on\;C_{25}-C_{27}\;position\;of\;aglycone$ in the interest of tracer studies in vivo. The method will be applicable to other dammalene glycosides regardless of their chemical structure. 4) The author and his co-workers converted chemically betulafolienetriol, a triterpene component of Betula platyphylla, to the protopanaxadiol, one of genuine aglycone of dammalene glycosides.

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Stability of Soybean Isoflavone Isomers According to Extraction Conditions

  • Choi, Yeon-Bae;Kim, Kang-Sung
    • 한국환경보건학회지
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    • 제31권6호
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    • pp.498-503
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    • 2005
  • Stability of soybean isoflavone isomers according to extraction conditions such as temperature, pH, and extracting solvents was investigated. Heating induced three chemical reactions to occur for malony1 derivatives of isoflavones, namely decarboxylation of malony1 groups into acety1 derivatives, deesterification of malony1 residues, and hydrolysis of $\beta$-glycosidic bonds. Among the twelve isoflavone isomers, change in concentrations of acety1glycosides were most pronounced: Acety1 derivatives were present only in trace amounts in unheated hypocotyls, but the content increased dramatically during heating. As for the glycosides, concentrations of daidzin and glycitin increased due to heat treatment, though that of genistin remained almost unchanged. Heat decomposition rates and the patterns differed among the three malony1 derivatives. After 120 min at $80^{circ}C$, the relative concentrations of daidzin, glycitin and genistin were increased from $9.2\%$, $12.4\%$ and $3.3\%$ to $19.3\%$, $21.9\%$ and $6.2\%$, respectively. When crude isoflavones were solubilized in glycine buffer (pH 10.0) and incubated at $80^{circ}C$, deesterification occurred faster than at pH 7.0. When the pH of isoflavone solution was increased, the malony1glycosides were hydrolyzed to their respective glycosides at increased rate. Both acetyl and aglycone forms were unchanged and only de-esterification reactions occurred. At the acidic pH, malonylglycosides were much stable both at 60 and $80^{circ}C$. However at pH 10, $80^{circ}C$ and 1 hr, $75-80\%$ of malonylglycosides were transformed to their deesterified glycosides. When isoflavones were extracted with $60\%$ aqueous ethanol at $60^{circ}C$, isoflavone isomers were stable and the deesterification reactions did not occur in these conditions. However, at $80^{circ}C$ deesterification of malonyiglycosides occurred significantly with $15-20\%$ of malonylglycosides being hydrolyzed into their respective glycosides. This experiment showed that malonylglycosides undergo decomposition when heated or exposed to alkaline conditions. Also, aqueous ethanol was preferred to aqueous methanol as solubilizing media for obtaining extract with minimum degradation of malonylglycosides.

은행잎 플라보놀배당체에 대한 셀루라제류의 영향 (The Effect of Cellulases on Flavonolglycosides of Ginkgo Leaf)

  • 배기환;민병선;백흠영;안병준
    • 약학회지
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    • 제35권4호
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    • pp.271-276
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    • 1991
  • The extractability and stability of ginkgoflavonolglycosides under presence of several cellulose preparations were investigated. The enzymes used were macerosin, cellulose C and cellulase NC. The content variation of the glycosides was measured with HPLC method, using caffeic acid as an internal standard. The methanol extract of ginkgo leaf, containing the total flavonolglycosides of 4.46%, was used for the content comparison. By extraction with the enzymes, each or mixed, the peak levels of all the glycosides began to decrease after 1 or 2 hours. After 24 hour extraction, most of the glycosides were degraded to minor components. The flavonolglycosides in ginkgo leaf were also hydrolysed simply by the water extraction. After 24 hour extraction with water at $40^{\circ}C$, the peak levels of major glycosides were distinctly decreased. Rutin was hydrolysed by enzyme treatment or by ginkgo leaf itself. As a result, it was concluded that the commercially available cellulases and the ginkgo leaf itself contain the activities of $\beta$-glycosidase and $\alpha$-rhamnosidase. Kaempferol-3-O-(6'"-O-p-coumaroylglucosyl)-rhamnoside and four other ginkgo flavonolglycosides were not hydrolysed under the same condition.tion.

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나무수국 꽃의 Secoiridoid, Iridoid 및 Flavonol 배당체의 골격근세포 비대 유도 효능 (Secoiridoids, Iridoids and Flavonol Glycosides from Hydrangea paniculata Flowers and their C2C12 Myotube Hypertrophic Activity)

  • 고은미;김철영
    • 생약학회지
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    • 제53권2호
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    • pp.57-63
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    • 2022
  • Five secoiridoids (1-3, 5, 10), a iridoid (4) three flavonol glycosides (7-9) and a coumarin (6), were isolated from the flowers of Hydrangea paniculata. Their chemical structures were elucidated as kingiside (1), morroniside (2), sweroside (3), loganin (4), vogeloside (5), umbelliferone (6), quercetin-3-O-sambubioside (7), quercetin-3-O-neohesperidoside (8), kaempferol 3-O-sambubioside (9) and secologanin dimethyl acetal (10), respectively, by spectroscopic analysis. All isolated compounds 1-10 were assessed for their ability to induce C2C12 myotube hypertrophy. Among them, loganin (4) and kaempferol 3-O-sambubioside (9) increase the diameter of C2C12 myotubes. All isolated compounds 1-10 were firstly reported from the flowers of Hydrangea paniculata, and the skeletal muscle hypertrophic activity of 4 and 9 was also reported for the first time.

C-Flavonoidal Glycosides from Erythrina caffra Flowers

  • El-Masry, Sawsan;Hammoda, Hala M.;Radwan, Mohamed M.;Ross, Samir A.;Zaatout, Hala H.
    • Natural Product Sciences
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    • 제16권4호
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    • pp.217-222
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    • 2010
  • A phytochemical investigation of the ethanolic extract of Erythrina caffra flowers from an Egyptian origin yielded three C-flavonoidal glycosides; 5,7,4'-trihydroxyflavone-8-C-$\beta$-D-glucopyranoside (vitexin) (1), 5,7,4'-trihydroxyflavone-6-C-$\beta$-D-glucopyranosyl-(1 $\rightarrow$ 2)-$\beta$-D-glucopyranoside (isovitexin-2"-$\beta$-D-glucopyranoside) (2), 5, 7, 4'-trihydroxyflavone-6, 8-di-C-$\beta$-D-glucopyranoside (vicenin-2) (3) and one O-flavonoidal glycoside; kaempferol-3-O-$\beta$-D.glucopyranosyl) (1 $\rightarrow$ 2)-$\beta$-D-glucopyranoside (4). The structures of the isolated compounds (1 - 4) were elucidated using different spectral techniques (UV, 1D and 2D NMR and HRESIMS). This is the first report for the isolation of flavonoidal glycosides from Erythrina caffra. The antibacterial, antifungal, antimalarial, and antileishmanial activities of the isolates were evaluated. In addition, the cytotoxic activity of the ethanolic extract and the main fractions were tested using brine shrimp bioassay.

Amyloglucosidase Catalyzed Syntheses of Bakuchiol Glycosides in Supercritical Carbon Dioxide

  • Manohar, Balaraman;Divakar, Soundar;Sankar, Kadimi Udaya
    • Bulletin of the Korean Chemical Society
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    • 제30권8호
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    • pp.1760-1766
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    • 2009
  • Enzymatic syntheses of water soluble Bakuchiol glycosides were carried out in di-isopropyl ether organic media using amyloglucosidase from Rhizopus mold. The reactions were carried out under conventional reflux conditions and in supercritical $CO_2$ atmospheric conditions. Out of the eleven carbohydrate molecules employed for the reaction, D-glucose, D-ribose and D-arabinose gave glycosides in yields of 9.0% to 51.4% under conventional reflux conditions. Under supercritical $CO_2$ atmosphere (100 bar pressure at 50 ${^{\circ}C}$), bakuchiol formed glycosides with Dglucose, D-galactose, D-mannose, D-fructose, D-ribose, D-arabinose, D-sorbitol and D-mannitol in yields ranging from 9% to 46.6%. Out of the bakuchiol glycosides prepared, 6-O-(6-D-fructofruranosyl)bakuchiol showed the best antioxidant (1.4 mM) and ACE inhibitory activities (0.64 mM).

Anti-Inflammatory Properties of Flavone di-C-Glycosides as Active Principles of Camellia Mistletoe, Korthalsella japonica

  • Kim, Min Kyoung;Yun, Kwang Jun;Lim, Da Hae;Kim, Jinju;Jang, Young Pyo
    • Biomolecules & Therapeutics
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    • 제24권6호
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    • pp.630-637
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    • 2016
  • The chemical components and biological activity of Camellia mistletoe, Korthalsella japonica (Loranthaceae) are relatively unknown compared to other mistletoe species. Therefore, we investigated the phytochemical properties and biological activity of this parasitic plant to provide essential preliminary scientific evidence to support and encourage its further pharmaceutical research and development. The major plant components were chromatographically isolated using high-performance liquid chromatography and their structures were elucidated using tandem mass spectrometry and nuclear magnetic resonance anlysis. Furthermore, the anti-inflammatory activity of the 70% ethanol extract of K. japonica (KJ) and its isolated components was evaluated using a nitric oxide (NO) assay and western blot analysis for inducible NO synthase (iNOS) and cyclooxygenase (COX)-2. Three flavone di-C-glycosides, lucenin-2, vicenin-2, and stellarin-2 were identified as major components of KJ, for the first time. KJ significantly inhibited NO production and reduced iNOS and COX-2 expression in lipopolysaccharide-stimulated RAW 264.7 cells at $100{\mu}g/mL$ while similar activity were observed with isolated flavone C-glycosides. In conclusion, KJ has a simple secondary metabolite profiles including flavone di-C-glycosides as major components and has a strong potential for further research and development as a source of therapeutic anti-inflammatory agents.

Carbon-13 NMR spectra of phytolaccagenin and its Glycosides

  • Woo, Won-Sick;Kang, Sam-Sik;Kazuo-Yamasaki;Osamu-Tanaka
    • Archives of Pharmacal Research
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    • 제1권1호
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    • pp.21-26
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    • 1978
  • In connection with structure studies on triterpenoid glycosides from Phytolacca plants, full assignments of $^{13}C-NMR signals of phytolaccagenin and its glycosides, phytolaccoside B and E, have been presented.

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초음파를 이용한 오죽으로부터 Flavone C-glycosioes의 추출 및 항산화활성분석 향상 (Enhanced extraction and Antioxidant activity analysis of Flavone C-glycosides from Black bamboo using Ultrasonic wave)

  • 최선도;이광진
    • KSBB Journal
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    • 제23권4호
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    • pp.297-302
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    • 2008
  • 오죽으로부터 HPLC On-line $ABTS^{+}$ screening기법을 사용하여 Flavone C-glycosides의 특성중의 하나인 항산화활성을 빠르게 분석하였으며, 오죽으로부터 homoorientin와 orientin의 추출을 다양한 초음파 주파수와 시간의 추출방법을 적용하였다. 전처리한 추출액에 포함된 오죽의 Flavone C-glycosides을 분석하고 최적의 추출조건을 실험적으로 모색하였다. 실험결과에 의하면 전체 수율에서는 Frequency 72 KHz, 60분에서 3.37 mg으로 추출 효율이 높았고, homoorientin와 orientin의 항산화활성은 Frequency 35 KHz, 30분으로 추출한 시료가 73.8%와 14.8%로 가장 우수하였다.