• Title/Summary/Keyword: 3,7-di-O-{\beta}-_D-glucopyranoside$

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Chlorogenic Acid, an Antioxidant Principle from the Aerial Parts of Artemisia iwayomogi that Acts on 1,1-Diphenyl-2-picrylhydrazyl Radical

  • Kim, Soon-Shin;Lee, Chung-Kyu;Sam, Sik-Kang;Jung, Hyun-Ah;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.20 no.2
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    • pp.148-154
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    • 1997
  • The antioxidant activity of Artemisia iwayomogi was determined by measuring the radical scavenging effect on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical. The methanol extract of A. iwayomogi showed strong antioxidant activity, and thus fractionated with several solvents. The antioxidant activity potential of the individual fraction was in the order of ethyl acetate > n-butanol > water > chloroform > n-hexane fraction. The ethyl acetate and n-butanol soluble fractions exhibiting strong antioxidant activity were further purified by repeated sitica get and Sephadex LH-20 column chromatography. Antioxidant chlorogenic acid was isolated as one of the active principles from the n-butanol fraction, together with the inactive components, 1octacosanol, scopoletin, scopolin, apigenin $7, 4^{I}$-di-O-methylether, luteolin $6, 3^{I}$-di-O-methylether (jaceosidin), apigenin methylether (genkwanin), 2, 4-dihydroxy-6-methoxyacetophenone $4-O-{\beta}-$D-glucopyranoside and quebrachitol. The antioxidant activity of chlorogenic acid was comparable to that of L-ascorbic acid, which is a well known antioxidant.

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Hepatoprotective constituents from Beta vulgaris var. cycla

  • Kim, In-Kyum;Chin, Young-Won;Song, Won-Lim;Yang, Hye-Kyung;Kim, Young-Choong;Kim, Jin-Woong
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.259.1-259.1
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    • 2003
  • In the course of hepatoprotective screening for domestic plants. the aerial parts of B. vulgaris var. cycla exhibited hepatoprotective activity which was determined by using the primary cultures of rat hepatocytes injured by H2O2. Bioactivity-guided separation for this plant gave a new flavonoid (1) and the known compounds (2-4), which structures were elucidated by 1H-NMR, HMQC, 1H-1H COSY and HMBC as compound 1, apigenin 8-C-, 7-O-di-$\beta$-D-glucopyranoside, compound 2, vitexin 2"-O-$\beta$-D-glucopyranoside, compound 3, (+)-dehydrovomifoliol, and compound 4, 3-hydroxy-5$\alpha$, 6$\alpha$-epoxy-$\beta$-ionone.

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Nitric Oxide Inhibitory Constituents from Fruits of Opuntia humifusa

  • Kang, You-Jeng;Kim, Hae-Young;Lee, Chul;Park, So-Young
    • Natural Product Sciences
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    • v.20 no.3
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    • pp.211-215
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    • 2014
  • Opuntia humifusa, also called as Cheonnyuncho, is a cactus widely cultivated in southern regions of Korea. It has been known to have diverse biological activities, but most of the studies were performed with the MeOH extracts or solvent-partitioned fractions. Furthermore, the efforts to identify the responsible compounds for the biological activities are very limited. In this study, we tested the inhibitory effect of extracts and solvent-partitioned fractions of O. humifusa against LPS-induced nitric oxide (NO) production in Raw264.7 cells. The butanol fractions of O. humifusa efficiently inhibited the production of NO in Raw264.7 cells, but it was not due to the reduction of cell viability. Bioassay-guided isolation of butanol fractions of O. humifusa allowed the isolation of three flavonoids isorhamnetin 3-O-${\beta}$-$\small{D}$-galactosyl-4'-O-${\beta}$-$\small{D}$-glucoside (1), isorhamnetin 3,4'-di-O-${\beta}$-$\small{D}$-glucoside (2) and isorhamnetin 3-O-${\beta}$-$\small{D}$-(6-O-${\alpha}$-$\small{L}$-rhamnosyl)glucoside (3), and one lignan syringaresinol O-${\beta}$-$\small{D}$-glucopyranoside (4). Among them, isorhamnetin 3-O-${\beta}$-$\small{D}$-galactosyl-4'-O-${\beta}$-$\small{D}$-glucoside (1) and isorhamnetin 3,4'-di-O-${\beta}$-$\small{D}$-glucoside (2) exhibited the moderate inhibitory effects against LPS-induced NO production. This is the first time to report anti-inflammatory effects of these compounds.

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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    • v.15 no.4
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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.

Phenolic Constituents from Juncus diastrophanthus (별날개골풀의 페놀성 성분)

  • Tao, Chao;Xing, Ming Ming;Ahn, Dalrae;Lee, Eun Byeol;Lee, So Yeon;Kim, Ban Ji;Lee, Jae Hyeok;Park, Jeong-Suk;Bae, Jong Jin;Kim, Dae Keun
    • Korean Journal of Pharmacognosy
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    • v.44 no.4
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    • pp.368-371
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    • 2013
  • Five phenolic compounds were isolated from the whole plants of Juncus diastrophanthus (Juncaceae) through repeated column chromatography. Their chemical structures were elucidated as methyl 3,5-di-O-caffeoylquinate (1), luteolin-7-O-${\beta}$-D-glucopyranoside (2), methyl 4,5-di-O-caffeoylquinate (3), quercetin-3-O-${\beta}$-D-arabinopyranoside (4), and methyl 3,4-di-O-caffeoylquinate (5) by spectroscopic techniques. These compounds were isolated for the first time from this plant.

Isolation of Phenolics, Nucleosides, Saccharides and an Alkaloid from the root of Aralia cordata

  • Hyun, Sook-Kyung;Jung, Hyun-Ah;Min, Byung-Sun;Jung, Jee-H.;Choi, Jae-Sue
    • Natural Product Sciences
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    • v.16 no.1
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    • pp.20-25
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    • 2010
  • Fourteen compounds were isolated from the n-BuOH fraction of the roots of Aralia cordata (syn. = A. continentalis). Through spectroscopic method, the chemical structures were elucidated as: caffeic acid (1), protocatechuic acid (2), thymidine (3), uridine (4), methyl-$\alpha$-D-fructofuranoside (5), a mixture (3 : 1) of $\beta$-D-fructopyranoside and $\beta$-D-fructofuranoside (6), 1-methyl 1,2,3,4-tetrahydro-$\beta$-carboline-3-carboxylic acid (7), methyl-$\beta$-D-fructofuranoside (8), sucrose (9), 5-caffeoylquinic acid (chlorogenic acid) (10), 3-caffeoylquinic acid (neochlorogenic acid) (11), 4-caffeoylquinic acid (cryptochlorogenic acid) (12), 3,5-di-O-caffeoylquinic acid (13), and 1-kestose [$\beta$-D-fructofuranosyl-($2{\rightarrow}1$)-$\beta$-D-fructofuranosyl-($2{\rightarrow}1$)-$\alpha$-D-glucopyranoside] (14). Among them, compounds 5, 7, 8, and 10 - 14 were isolated from this plant for the first time.

Chemical constituents of Dicentra spectabilis and their anti-inflammation effect

  • Kim, A Hyeon;Jang, Ji Hun;Woo, Kyeong Wan;Park, Jong Eel;Lee, Ki Ho;Jung, Ho Kyung;An, Byeongkwan;Jung, Won Seok;Ham, Seong Ho;Cho, Hyun Woo
    • Journal of Applied Biological Chemistry
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    • v.61 no.1
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    • pp.39-46
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    • 2018
  • Column chromatographic separation of the MeOH extract from the roots of Dicentra spectabilis yielded fourteen compounds, menisdaurin (1), menisdaurilide (2), trans-N-p-coumaroyltyramine (3), trans-N-p-feruloyltyramine (4), 4-O-feruloylquinicacid (5), chlorogenic acid (6), 3-O-feruloylquinicacid (7), ferulic acid (8), protopine (9), Kaempferol 3,7-di-O-${\beta}-{\text\tiny{D}}$-glucopyranoside (10), kaempferol 3-O-${\beta}-{\text\tiny{D}}$-glucopyranosyl-7-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranoside (11), ${\alpha}-rhamnoisorobin$ (12), astragalin (13), and nicotiflorin (14). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 1, 3-8, and 10-14 isolated from this plant were reported for the first time. The isolated compounds (1-14) were tested for nitric oxide (NO) inhibitory activity on lipopolysaccharide-stimulated RAW 264.7 cells. Compound 3, 4 and 12 significantly inhibited NO production. Moreover, Compound 3 suppressed pro-inflammatory cytokines ($TNF-{\alpha}$, $IL-1{\beta}$ and IL-6) in a dose- dependent manner. These data suggest that compound 3 possess anti-inflammatory activity and might be useful natural materials for development of anti-inflammatory agent.

Anti-inflammatory Activity of Flavonoids from Populus davidiana

  • Zhang, XinFeng;Hung, Tran Manh;Phuong, Phuong Thien;Ngoc, Tran Minh;Min, Byung-Sun;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Archives of Pharmacal Research
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    • v.29 no.12
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    • pp.1102-1108
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    • 2006
  • An in vitro bioassay-guide revealed that the methanol (MeOH) extract of the stem bark of Populus davidiana showed considerable inhibitory activity against cyclooxygenase (COX-1, COX-2). Continuous phytochemical study of the MeOH extract of this plant led to the isolation of ten flavonoids; sakuranetin (1), rhamnocitrin (2), 7-O-methylaromadendrin (3), naringenin (4), eriodictyol (5), aromadendrin (6), kaempferol (7), neosakuranin (8), sakuranin (9) and sakurenetin-5,4'-di-${\beta}$-D-glucopyranoside (10). Their structures were identified on the basis of their physicochemical and spectroscopic analyses. The isolated compounds, 1-10, were tested for their inhibitory activities against COX-1 and COX-2. Compound 7 was found to have potent inhibitory effect on COX-1 and a moderate effect on COX-2, meanwhile, compounds 1-6 showed moderate inhibition against COX-1 only. Moreover, compounds 5-8 exhibited suppressive effects on xanthine oxidase (XO). These results may explain, in part, the traditional uses of P. davidiana in ethnomedicine.

Chemical Constituents from the Bark of Phellodendron amurense and Their Cytotoxic Effects on HL-60 Human Leukemia Cells

  • Li, Wei;Sun, Ya Nan;Yan, Xi Tao;Yang, Seo Young;Choi, Chun Whan;Kim, Eun Ji;Kang, Hee Kyoung;Kim, Young Ho
    • Natural Product Sciences
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    • v.18 no.4
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    • pp.250-253
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    • 2012
  • Phellodendri Cortex, phellodendron bark, has been used as a stomachic for intestinal function control and as an antimicro and anti-inflammatory agent. In this phytochemical study, eight compounds, berberine (1), palmatine (2), syringin (3), (+)-syringaresinol di-O-${\beta}$-D-glucopyranoside (4), salvadoraside (5), citrusin B (6), osmanthuside H (7), and kelampayoside A (8), were isolated from the bark of Phellodendron amurense. Their structures were elucidated by comparing spectroscopic data with reported values. Compounds 1 - 8 were evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells in vitro. Among them, compounds 1 and 2 reduced the viability of HL-60 cells significantly, with $IC_{50}$ values of 26.0 and $18.5{\mu}M$, respectively.