• Title/Summary/Keyword: C-glycosides

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Reaction mechanism of translated xylanase from Thermatoga maritima MSB 8 and preparation of propyl-glycosides

  • Park, Jun-Seong;Kitaoka, Motomitsu;Hayashi, Kiyoshi;Kim, Do-Man
    • 한국생물공학회:학술대회논문집
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    • 2002.04a
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    • pp.477-480
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    • 2002
  • A thermostable xylanase from Thermotoga maritima (Xyn B) cleaves several pNP-glycosides of monosaccharides. We found that the initial product of the cleavage of pNP-xyloside (pNP-Xy1) was a disaccharide, not xylose, indicating that xylosyl unit of pNP-Xyl was transglycosylated to another pNP-Xyl. We determined that the disaccharide was xylobiose which has the linkage of the ${\beta}$ 1-4, and described the reaction mechanism of the Xyn B. Also, we produced the several pNP-glycosides and propyl-disaccharides from the transglycosylation of Xyn B with varial glycosides and/or 1-propanol. All reaction products were purified by column chromatography (Toyo-pearl HW-40C, 45 cm${\times}$2.5 cm or 45 cm ${\times}$ 2.5 cm${\times}$ 2). The isolated products were analyzed by means of 1D and 2D NMR.

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Flavonoid Glycosides from the Flowers of Pulsatilla koreana Nakai

  • Seo, Kyeong-Hwa;Jung, Jae-Woo;Nhan, Nguyen Thi;Lee, Youn-Hyung;Baek, Nam-In
    • Natural Product Sciences
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    • v.22 no.1
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    • pp.41-45
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    • 2016
  • Extraction and fractionation of Pulsatilla koreana flowers followed by, repeated open column chromatography for EtOAc and n-BuOH fractions yielded four flavonoid glycosides, namely, astragalin (1), tiliroside (2), buddlenoide A (3), and apigenin-7-O-(3"-E-p-coumaroyl)-glucopyranoside (4). The chemical structures of these flavonoid glycosides were elucidated on the basis of various spectroscopic methods including electronic ionization mass spectrometry (EI-MS), 1D NMR ($^1H$, $^{13}C$, DEPT), 2D NMR (gCOSY, gHSQC, gHMBC), and infrared (IR) spectrometry. This study represents the first report of the isolation of the flavonoid glycosides from the flowers of P. koreana.

Two Biophenolic Glycosides from Portulaca oleracea (쇠비름에서 분리된 2개의 Biophenolic Glycosides)

  • Youngwan Seo;Jongheon Shin;Burm Jong Lee;Dong Seok Lee
    • Journal of the Korean Chemical Society
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    • v.47 no.1
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    • pp.43-46
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    • 2003
  • From Portulaca oleracea which is widely distributed in Korea and has long been used as a folk medicine, two biophenolic glycosides, 3-hydroxy-1-(2-hydroxyethyl)phenyl-4-O-${\beta}$-D-glucopyranoside (1) and 2-(3,4-dihydroxyphenyl) ethyl-O-${\beta}$-D-glucopyranoside (2) were isolated using column chromatography and reversed-phase HPLC. $^{13}C$ NMR spectral assignment for these compounds was revised by the extensive 2-D NMR experiments such as NOESY, HMQC, and HMBC. These compounds showed a considerable antioxidant effect in DPPH assay system.

Isolation and Identification of Stilbene glycosides from the Bark of Pinus koraiensis (잣나무 수피의 Stilbene glycosides의 분리 및 동정)

  • Song, Hong-Keun
    • Journal of the Korean Wood Science and Technology
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    • v.29 no.4
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    • pp.97-102
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    • 2001
  • EtOAc extract from the bark of Pinus koraiensis Sieb. et Zucc was isolated by column chromatography which was packed with Sephadex LH-20 or TSK-gel HW-40F. Several stilbene glycosides were identified by $^1H{\cdot}^{13}C$-NMR, HMQC, HMBC and $FAB^+$ MS. Three stilbene glycosides, Z-pinostilbenoside, E-desoxyrhaponticin, and E-resveratroloside, were identified.

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Coumarin Glycosides from the Root Bark of Flaxinus sieboldiana Blume(II) (쇠물푸레나무 근피(根皮)의 Coumarin배당체(配糖體) (제2보)(第2報))

  • Yook, Chang-Soo;Moon, Chang-Kiu
    • Korean Journal of Pharmacognosy
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    • v.12 no.3
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    • pp.143-145
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    • 1981
  • The methanol extract of the rootbark of Fraxinus sieboldiana Blume(Oleaceae) gave two coumarin glycosides, fraxin (fraxetin-8-glucoside), $C_{16}H_{18}O_{10},\;mp\;204^{\circ}\;and\;esculin\;(esculetin-6-glucoside),\;C_{15}H_{16}O_{9},\;mp\;204{\sim}205^{\circ}$. Beside, the methanol extract of the root bark was found to contain mannitol. ${\beta}-sitosterol$ is confirmed by massspectrometry.

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Induction of Quinone Reductase and Glutathione S-Transferase in Murine Hepatoma Cells by Flavonoid Glycosides

  • Kim, Jung-Hyun;Lee, Jeong-Soon;Kim, Young-Chan;Chung, Shin-Kyo;Kwon, Chong-Suk;Kim, Young-Kyoon;Kim, Jong-Sang
    • Preventive Nutrition and Food Science
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    • v.8 no.4
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    • pp.365-371
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    • 2003
  • The potential of seven flavonoid glycosides to induce quinone reductase (QR), an anticarcinogenic marker enzyme, in murine hepatoma cells (hepalc1c7) and its mutant cells (BPRc1) was evaluated. Among test compounds, kaempferol-3-O-glucoside, luteolin-6-c-glucoside, and quercetin-3-O-glucoside (Q-3-G) induced QR in hepalc1c7 cells in a dose-dependent manner. However, in BPRc1 cells lacking arylhydrocarbon receptor nuclear translocator (ARNT), only Q-3-G caused a significant induction of quinone reductase at the concentration range of 0.5 to 8 ug/mL, suggesting that it is a monofunctional inducer. Q-3-G induced not only phase 2 enzymes, including QR and glutathione-S-transferase, but also nitroblue tetrazolium reduction activity in HL-60 cells, a biochemical marker for cell differentiation promoting agents. In conclusion, Q-3-G merits further study to evaluate its cancer chemopreventive potential.

The flavone glycosides of Sasa borealis (조릿대잎의 flavone 배당체 성분)

  • Yoon, Ki-Dong;Kim, Chul-Young;Huh, Hoon
    • Korean Journal of Pharmacognosy
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    • v.31 no.2
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    • pp.224-227
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    • 2000
  • As part of study of the constituents of bamboo grasses, the leaves of Sasa borealis (Hackel) Makino (Gramineae) were examined. Friedelin, glutinol, isoorientin and isovitexin have been reported as constituents of bamboo grasses. In this study, tricin and two flavone glycosides, tricin $7-O-{\beta}-D-glucopyranoside$ and luteolin $6-C-{\alpha}-L-arabinopyranoside$ have been isolated from EtOAc extract of S. borealis, by consecutive silica gel, Sephadex LH-20 column chromatography and a repetitive HPLC. The structures of these compounds were determined by IR, $^1H-NMR,\;^{13}C-NMR,\;^{13}C-^1H\;COSY,\;^1H-^1H\;COSY,\;HMBC$ and Mass spectral data.

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Structures of Dotorioside I and II Obtained from the Fruits of Quercus acutissima $C_{ARRUTHERS}$ (도토리에서 분리한 Dotorioside I, II의 구조)

  • Im, Kwang-Sik;Son, Mee-Jeong;Lee, See-Kang
    • YAKHAK HOEJI
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    • v.38 no.3
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    • pp.223-229
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    • 1994
  • From the methanolic extractive of the fruits of Quercus acutissima $C_{ARRUTHERS}$(Fagaceae) a mixture(QC-A saponin) of two ester glycosides, which were named as dotorioside I(3) and ll(4), was separated by silica gel column chromatography and HPLC. The structures of these two glycosides including their genuine aglycones(1,2) were elucidated as 1: $2{\alpha}$, $3{\beta}$, $19{\alpha}$, 23-tetrahydroxyolean-12-en-28-oic acid, 2: $2{\alpha}$, $3{\beta}$, $19{\alpha}$, 23-tetrahydroxyurs-12-en-28-oci acid, 3: 28-O-${\beta}$-D-glucopyranosyl ester of 1, 4: 28-O-${\beta}$-D-glucopyranosyl ester of 2, respectively, on the basis of chemical and spectral evidence.

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Phenolic glycosides from Pyrola japonica-(II)

  • Kim, Ju-Sun;Kang, Sam-Sik;Son, Kun-Ho;Chang, Hyeun-Wook;Kim, Hyun-Pyo
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.256.2-256.1
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    • 2003
  • Six known phenolic glycosides. hyperin(2), androsin(3), homoarbutin(4), isohomoarbutin(4a), pirolatin(7) and monotropein(6), together with two new compounds, (1)[mp. 215 - 217$^{\circ}C$, C$\sub$23/H$\sub$32/O$\sub$11/] and (5)[mp. 121 -123$^{\circ}C$, C$\sub$18/H$\sub$26/O$\sub$8/] were isolated from the BuOH fraction of Pyrola japonica(Pyrolaceae). The structures of the known compounds were determined by chemical and spectroscopic methods. (omitted)

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