• 제목/요약/키워드: methyl $\alpha$-D-glucopyranoside

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사방오리 잎의 Triterpenoid 및 Flavonoid 화합물 (Triterpenoids and Flavonoids Isolated from the Leaves of Alnus firma)

  • 유영법;;;;박종철
    • 생약학회지
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    • 제38권1호
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    • pp.76-83
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    • 2007
  • In this study, three triterpenoids, two steroids and nine flavonoids were isolated from the leaves of Alnus firma Sieb. et Zucc. On the basis of spectroscopic evidences, the structures of these compounds were established as ${\beta}$-amyrin acetate, ${\beta}$-amyrin, ${\beta}$-sitosterol, alnustic acid methyl ester, ${\beta}$-sitosterol glucoside, pinocembrin, alnustinol, quercetin, quercetin-3-O-${\alpha}$-L-arabinofuranoside, quercetin-3-O-${\alpha}$-L -rhamnopyranoside, quercetin-3-O-${\beta}$-D-glucopyranoside, myricetin-3-O-${\beta}$-D-galac-topyranoside, (+)-catechin and (-)-epicatechin.

Complete Assignment of the $^H1$ and $^{13}C$ NMR Spectra of a Sucrose Ester from Euphorbia Lathyris L.

  • Jung, Min-Hwan;Kim, Hyun-Sik;Sangdoo Ahn;Kim, Cheong-Taek;Jin, Mu-Hyun;Yim, Yong-Hyeon;Kim, Young-Kook;Jong hoa Ok
    • 한국자기공명학회논문지
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    • 제4권2호
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    • pp.125-132
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    • 2000
  • The detailed $^1$H and $^{13}$ C NMR assignments of a novel sucrose isovaleryl ester isolated from the seed of Euphorbia Lathyris L., were achieved by one-and two-dimensional techniques. The new sucrose ester was characterized as an $\alpha$-D-glucopyranoside, 3,4,6-tris-O-(3-methyl-1-oxobutyl)-$\beta$-D-fructofuranosyl, 2,6-bis(3-methylbutanoate); sucrose 4,7,8,11,12-pentaisovalerate by MS and NMR experiments.

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A New Sesquiterpene Hydroperoxide from the Aerial Parts of Aster oharai

  • Choi, Sang-Zin;Lee, Sung-Ok;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • 제26권7호
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    • pp.521-525
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    • 2003
  • Phytochemical works on the aerial parts of Aster oharai (Compositae) led to the isolation of a new sesquiterpene hydroperoxide, 7$\alpha$-hydroperoxy-3, 11-eudesmadiene (2) and seven known compounds, teucdiol B (1), $\alpha$-spinasterol (3), oleanolic acid (4), $\alpha$-spinasterol 3-Ο-$\beta$-D-glucopyranoside (5), methyl 3,5-di-Ο-caffeoyl quinate (6), 3,5-di-Ο-caffeoylquinic acid (7), 3,4-di-Ο-caffeoylquinic acid (8). The chemical structures of 1-8 were established by chemical and spectroscopic methods. Compound 2 showed cytotoxicity against cultured human tumor cell lines in vitro, SK-OV-3 (ovarian), SK-MEL-2 (skin melanoma), and HCT15 (colon) with $ED_{50}$ values ranging from 3.86-17.21 $\mu$g/mL.

애기땅빈대의 화학적 성분 (Chemical constituents from the whole plants of Euphorbia supina Rafin)

  • 안인파;권지웅;권태오;정완태;이혜숙;김윤철
    • 생약학회지
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    • 제38권3호통권150호
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    • pp.291-295
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    • 2007
  • Eight compounds were isolated from the whole plants of Euphorbia supina (Euphorbiaceae) through repeated silica gel, YMC gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as 7-hydroxy-6-methoxycoumarin (scopoletin) (1), p-hydroxybenzaldehyde (2), methyl gallate (3), gallic acid (4), quercetin (5), quercetin $3-O-{\alpha}-L-arabinofuranoside$ (avicularin) (6), kaempferol $3-O-{\alpha}-L-arabinofuranoside$ (juglanin) (7) and kaempferol $3-O-{\beta}-D-glucopyranoside$ (astragaline) (8) by spectroscopic (NMR and MS) analysis.

Phenolic Compounds from Fruits of Amorpha fruticosa L.

  • Lee, hak-Ju;Lee, Hyun-Jung;Park, Il-Kwon;Shin, Sang-Chul;Lee, Myung-Koo;Paik, Ki-Hyon
    • 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.190.4-191
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    • 2003
  • This study was carried out to examine the constituents of Amorpha fruticosa (Leguminosae), a shrub originated from North Africa. Dried and ground fruit of A. fruticosa were extracted with methanol and then concentrated to give the crude extracts. The crude extracts was successively fractioned with organic sovents, such as n-hexane, CH$_2$Cl$_2$ and EtOAc. Seven compounds were isolated from the fruits of A. fruticosa. On the basis of spectrosopic data, the structures of these compounds were determined as: kaempferol 7-O-${\alpha}$-L-rhamnopyranoside (I), methyl 3,4,5- trihydroxybenzoate (methyl gallate, II), tephrosin (III), dalbinol (IV), gallic acid (V), 2",4",5",7-tetramethoxyisofavone (Ⅵ) and Dalbinol 2"-O-${\beta}$-D-Glucopyranoside (Ⅶ) respectively. (omitted)

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Chemical Constituents from Artemisia iwayomogi Increase the Function of Osteoblastic MC3T3-E1 Cells

  • Ding, Yan;Liang, Chun;Choi, Eun-Mi;Ra, Jeong-Chan;Kim, Young-Ho
    • Natural Product Sciences
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    • 제15권4호
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    • pp.192-197
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    • 2009
  • Chemical investigation of the aerial parts of Artemisia iwayomogi has afforded five glycoside compounds. Their chemical structures were characterized by spectroscopic methods to be turpinionoside A (1), (Z)-3-hexenyl O-${\alpha}$-arabinopyranosyl-(1${\rightarrow}$6)-O-${\beta}$-D-glucopyranoside (2), (Z)-5'-hydroxyjasmone 5'-O-${\beta}$-Dglucopyranoside (3), (-)-syringaresinol-4-O-${\beta}$-D-glucopyranoside (4), and methyl 3,5-di-O-caffeoyl quinate (5). All of them were isolated for the first time from Artemisia species. The effect of compounds 1 - 5 on the function of osteoblastic MC3T3-E1 cells was examined by checking the cell viability, alkaline phosphatase (ALP) activity, collagen synthesis, and mineralization. Turpinionoside A (1) significantly increased the function of osteoblastic MC3T3-E1 cells. Cell viability, ALP activity, collagen synthesis, and mineralization were increased up to 117.2% (2 ${\mu}M$), 110.7% (0.4 ${\mu}M$), 156.0% (0.4 ${\mu}M$), and 143.0 % (2 ${\mu}M$), respectively.

Lipid Peroxidation Inhibitory Activity of Some Constituents isolated from the Stem Bark of Eucalyptus globulus

  • Yun, Bong-Sik;Lee, In-Kyoung;Kim, Jong-Pyung;Chung, Sung-Hyun;Shim, Gyu-Seop;Yoo, Ick-Dong
    • Archives of Pharmacal Research
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    • 제23권2호
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    • pp.147-150
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    • 2000
  • Twelve compounds with lipid peroxidation inhibitory activity were isolated from the stem bark of E. globulus. Their structures were assigned as a new aromatic monoterpene (1) and eleven known compounds, pinoresinol (2), vomifoliol (3), 3,4,5-trimethoxyphenol 1-O-$\beta$-D-(6'-O-galloyl)glucopyranoside (4), methyl gallate (5), rhamnazin (6), rhamnetin (7), eriodictyol (8), quercetin (9), taxifolin (10), engelitin (11), and catechin (12) on the basis of UV, mass, and NMR spectroscopic analyses. These compounds except vomifoliol significantly inhibited lipid peroxidation in rat liver microsome.

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In vitro Free Radical Scavenging and Hepatoprotective Compound from Sanguisorbae Radix

  • An, Ren-Bo;Tian, Yu-Hua;Oh, Hyun-Cheol;Kim, Youn-Chul
    • Natural Product Sciences
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    • 제11권3호
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    • pp.119-122
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    • 2005
  • In the course of searching for hepatoprotective agents from natural products, four compounds were isolated from the MeOH extract of Sanguisorbae Radix, as guided by their DPPH free radical scavenging activity. The structures were determined as 4,5-dimethoxy-3-hydroxybenzoic acid methyl ester (1), (+)-gallocatechin (2), methyl $6-O-galloyl-{\beta}-D-glucopyranoside$ (3), and pomolic acid $3-O-[{\alpha}-L-arabinopyranoside]-28-O-[{\beta}-D-glucopyranosyl]$ ester (ziyu-glycoside I) (4). Compounds 2 and 3 showed significant DPPH free radical scavenging effects, exhibiting $IC_{50}$ values of 11.4 and $13.0\;{\mu}M$, respectively. L-Ascorbic acid was used as a positive control and exhibited the $IC_{50}$ value of $50.3\;{\mu}M$. In evaluation of the hepatoprotective activity of the isolated compounds on drug-induced cytotoxicity, compound 2 showed the significant hepatoprotective effect with the $EC_{50}$ value of $91.84\;{\pm}\;11.0\;{\mu}M$ on tacrine-induced cytotoxicity in Hep G2 cells, while silybin, a positive control, exhibited $EC_{50}$ value of $122.4\;{\pm}\;12.5\;{\mu}M$.

Isolation and Structural Determination of Free Radical Scavenging Compounds from Korean Fermented Red Pepper Paste (Kochujang)

  • Chung, Jin-Ho;Shin, Heung-Chule;Cho, Jeong-Yong;Kang, Seong-Koo;Lee, Hyoung-Jae;Shin, Soo-Cheol;Park, Keun-Hyung;Moon, Jae-Hak
    • Food Science and Biotechnology
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    • 제18권2호
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    • pp.463-470
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    • 2009
  • Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.

Effects of High Glucose Levels on the Protein Kinase C Signal Transduction Pathway in Primary Cultured Renal Proximal Tubule Cells

  • Han, Ho-Jae;Kang, Ju-Won;Park, Kwon-Moo
    • The Korean Journal of Physiology
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    • 제30권2호
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    • pp.257-267
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    • 1996
  • Diabetes mellitus is associated with a wide range of pathophysiologic changes in the kidney. This study was designed to examine the mechanisms by which glucose modulates the expression of polarized membrane transport functions in primary cultured rabbit renal proximal tubule cells. Results are as follows: The rate of 30 minute $Rb^{+}$ uptake was significantly higher($137.76{\pm}5.40%$) in primary renal tubular cell cultures treated with 20 mM glucose than that of 5 mM glucose. Not the level of mRNA for the ${\alpha}$ subunit of Na, K-ATPase but that of ${\beta}$ subunit was elevated in primary cultures treated with high glucose. The initial rate of methyl-${\alpha}$-D-glucopyranoside(${\alpha}$-MG) uptake was significantly lower($71.91{\pm}3.02%$) in monolayers treated with 20 mM glucose than that of 5 mM glucose. There was a tendency of an increase in phlorizin binding site in cells treated with 5 mM glucose. However, 3-O-methyl-D-glucose(3-O-MG) uptake was not affected by glucose concentration in culture media. TPA inhibited $Rb^{+}$ uptake by $63.61{\pm}1.94\;and\;45.80{\pm}1.36%$ and ${\alpha}$-MG uptake by $48.54{\pm}3.69\;and\;41.87{\pm}6.70%$ in the cells treated with 5 and 20 mM glucose, respectively. Also TPA inhibited mRNA expression of Na/glucose cotransporter in cells grown in 5mM glucose medium. cAMP significantly stimulated ${\alpha}$-MG uptake by $114.65{\pm}5.70%$ in cells treated with 5mM glucose, while it did not affect ${\alpha}$-MG uptake in cell treated with 20 mM glucose. However, cAMP inhibited $Rb^{+}$ uptake by $76.69{\pm}4.16\;and\;66.87{\pm}2.41%$ in cells treated with 5 and 20 mM glucose, respectively. In conclusion, the activity of the renal proximal tubular Na,K-ATPase is elevated in high glucose concentration. In contrast, the activity of the Na/glucose cotransport system is inhibited. High glucose may in part affect the activity of the Na,K-ATPase and the Na/glucose cotransport system by controlling the protein kinase C and/or A signal transduction pathway in primary cultured renal proximal tubule cells.

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