• Title/Summary/Keyword: }3-O-{\alpha}-_L-rhamnopyranosyl(1{\rightarrow} 2)-{\beta}-_D-glucopyranoside$

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Anti-cancer Activity of Flavonoids from Aceriphyllum rossii (돌단풍(Aceriphyllum rossii)에서 분리한 플라보노이드의 항암활성)

  • Ahn, Eun-Mi;Han, Jae-Taek;Kwon, Byoung-Mog;Kim, Sung-Hoon;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.51 no.4
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    • pp.309-315
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    • 2008
  • The methanol extract from the aerial parts of Aceriphyllum rossii was fractionated into ethyl acetate, n-BuOH and $H_2O$ layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc and n-BuOH layers afforded five flavonol glycosides. They were identified as astragalin (1), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (2), rutin (3), kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl 1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (4), and quercetin 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$4)-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$6)-${\beta}$-D-glucopyranoside (5) on the basis of spectroscopic data. All of them showed an inhibition in farnesyl protein tranferase (FPTase) activity, and rutin (3) inhibited the growth of rat H-ras cell and the cell migration of human umbilical vein endothelial cells (HUVECs).

A New Steroidal Glycoside from Allium macrostemon Bunge

  • Kim, Yun Sik;Cha, Joon Min;Kim, Dong Hyun;Lee, Tae Hyun;Lee, Kang Ro
    • Natural Product Sciences
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    • v.24 no.1
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    • pp.54-58
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    • 2018
  • A phytochemical investigation of Allium macrostemon Bunge (Liliaceae) afforded the new pregnane steroidal glycoside, named allimacroside F (1), along with three known glycosides, benzyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (2), phenylethyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (3), (Z)-3-hexenyl-O-${\alpha}-{\text\tiny{L}}$-rhamnopyranosyl-($1{\rightarrow}6$)-${\beta}-{\text\tiny{D}}$-glucopyranoside (4). The identification and structural elucidation of a new compound (1) was carried out based on spectral data analyses ($^1H-NMR$, $^{13}C-NMR$, $^1H-^1H$ COSY, HSQC, HMBC, and NOESY) and HR-FAB-MS.

Deveolopment of Biologically Active Compounds from Edible Plant Sources-XII. - Flavonol Glycosides from Trigonotis peduncularis Benth and its hACAT1 Inhibitory Activity - (식용식물자원으로부터 활성물질의 탐색-XII. - 꽃마리(Trigonotis peduncularis Benth.)로부터 Flavonol 배당체의 분리 및 hACAT1 저해활성 -)

  • Yang, Hye-Joung;Song, Myoung-Chong;Bang, Myun-Ho;Lee, Jin-Hee;Chung, In-Sik;Lee, Youn-Hyung;Jeong, Tae-Sook;Kwon, Byoung-Mog;Kim, Sung-Hoon;Kim, Dae-Keun;Park, Mi-Hyun;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.48 no.1
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    • pp.98-102
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    • 2005
  • The MeOH extracts obtained from whole plant of Trigonotis peduncularis Benth. were solvent fractionated using EtOAc, n-BuOH and water, successively. The EtOAc and n-BuOH fractions gave four flavonol glycosides through application of silica gel and octadecyl silica gel (ODS) column chromatographies. The chemical structures of the flavonol glycosides were determined by the interpretation of several spectral data including 2D-NMR as $kaempferol-3-O-{\beta}-{D}-glucopyranoside\;(astragalin,\;1),\;kaempferol-3-O-{\alpha}-{L}-rhamnopyranosyl\;(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(nicotiflorin,\;2),\;quercetin-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(rutin,\;3),\;quercetin-3-O-{\beta}-{D}-glucopyranoside\;(isoquercitrin,\;4)$. The flavonoids have been first isolated from this plant. Nicotiflorin $(100\;{\mu}g/ml)$ showed $68.3{\pm}1.2%$ of the inhibitory effect on hACAT1(human Acyl CoA: cholesterol transferase 1) activity.

Phytochemical Components from the Whole Plants of Bothriospermum tenellum (꽃바지 전초의 식물화학적 성분)

  • Jang, Choon-Hee;Eun, Jae-Soon;Lim, Jong-Pil;Park, Hee-Wook;Kim, Jin-Wook;Shin, Tae-Yong;Eom, Dong-Ok;Baek, Nam-In;Kim, Dae-Keun
    • Korean Journal of Pharmacognosy
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    • v.34 no.2 s.133
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    • pp.119-122
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    • 2003
  • From the whole plants of Bothriospermum tenellum (Boraginaceae) four phenolic compounds, kaempferol, caffeic acid, $kaempferol-3-O-{\beta}-D-glucopyranoside$ and $kaempferol-3-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ have been isolated and characterized by physicochemical and spectral means.

A New Flavonoid from Carrichtera annua

  • Shahat, Abdelaaty A.;Abdel-Shafeek, Khaled A.;Husseiny, Husseiny A.;Claeys, Magda;Apers, Sandra;Pieters, Luc
    • Natural Product Sciences
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    • v.12 no.3
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    • pp.122-124
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    • 2006
  • Three flavonoid glycosides, $kaempferol-3-O-{\alpha}-L-rhamnopyranosyl-(1\;{\rightarrow}\;6)-{\beta}$-D-glucopyranoside$ or kaempferol-3-O-rutinoside (1), $isorhamnetic-3-O-{\alpha}-L-rhamnopyranosyl-(16)-{\beta}-D-glucopyranoside$ or isorhamnetin-3-O-rutinoside (2), and $quercetin-3-O-{\beta}-D-glucopyranosyl-(1 ${\rightarrow}\;2)-{\beta}-L-arabinopyranoside$ 3, the latter one being a new compound, were isolated from the methanolic extract of the aerial parts of Carrichtera annua. Mass spectrometry and 1D and 2D NMR spectroscopy allowed establishing the structure of these compounds.

Isolation of Anti-oxidant from Domestic Crataegus pinnatifida Bunge Leaves (국산 산사나무 잎으로부터 항산화 활성성분의 분리)

  • Kang, In-Ho;Cha, Ja-Hyun;Han, Jeong-Hun;Lee, Seong-Wan;Kim, Hon-Jin;Kwon, Suck-Hyung;Ham, In-Hye;Hwang, Bo-Sik;Whang, Wan-Kyunn
    • Korean Journal of Pharmacognosy
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    • v.36 no.2 s.141
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    • pp.121-128
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    • 2005
  • In order to find the antioxidative compounds, fractionation of the MeOH extract of the leaves of Crataegus pinnatifida guided by DPPH scavenging test furnished seven phenolic compounds, $quercetin-3-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (1), myricetin-3-O-rhamnose (2), $quercetin-3-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}6)-{\beta}-D-galctopyranoside$ (3), $quercetin-3-O-{\beta}-D-galactopyranoside$ (4), quercetin (5), $apigenin-8-C-{\beta}-L-rhamnopyranosyl-(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (2'-O-rhamnosylvitexin) (6) and (-)-epicatechin (7). All of isolated compounds showed the significant antioxidative effect on DPPH free radical scavenging test and TBARS assay.

Isolation of Flavonoids from Carthami Flos and their Antioxidative Activity (홍화의 플라보노이드 성분 분리 및 항산화 활성)

  • Chung, Sung-Hee;Moon, Ye-Ji;Kim, Sung-Gun;Kim, Kyoung-Young;Lee, Kyoung-Tae;Kim, Ho-Kyoung;Whang, Wan-Kyunn
    • YAKHAK HOEJI
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    • v.52 no.4
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    • pp.241-251
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    • 2008
  • In this study, isolation of antioxidative compounds was performed for development of anti-oxidizing agent. $CHCl_{3}$, $H_{2}O$, 30%, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH method, TBARS assay, and SOD like activity. It was revealed that 30%, 60% MeOH fractions had significant antioxidative activity. From 30%, 60% MeOH fraction, nine compounds were isolated and elucidated kaempferol $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (1), quercetin $7-O-{\beta}-D-glucopyranoside$ (II), quercetin $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)$ ${\beta}-D-glucopyranoside(rutin)$ (III), 6-hydroxykaempferol $3-O-{\beta}-D-glucopyranoside$ (lV), kaempferol $3-O-{\beta}-D-glucopyranosyl$ $(1{\rightarrow}2)$ ${\beta}-D-glucopyranoside$ (V), kaempferol $3-O-{\beta}-D-glucopyranoside$ (VI), luteolin (VII), quercetin $3-O-{\beta}-D-glucopyranoside$ (VIII), apigenin $7-O-{\beta}-D-glucuronopyranoside$ (IX) through physicochemical data and spectroscopic methods (Negative FAB-MS, $^1H-NMR$, $^{13}C-NMR$). Entirely, all compounds had similar antioxidative activity, but more OH group had more antioxidative activity.

Isolation of Toxic Saponins from the Roots of Patrinia scabiosaefolia

  • Woo, Won-Sick;Choi, Jae-Sue;Shin, Kuk-Hyun
    • Korean Journal of Pharmacognosy
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    • v.16 no.4
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    • pp.248-252
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    • 1985
  • During the biological screening of Chinese drugs, it was found that alcoholic extract of the roots of Patrinia scabiosaefolia (Valerianaceae) caused a significant prolongation of hexobarbital-induced sleeping time and elevation of serum transaminase activities accompanied by severe histopathological changes in the hepatic tissues in mice on three day pretreatments. The systematic fractionation of the methanol extract monitoring by bioassay led to isolation of toxic saponins such as $3-O-{\alpha}-{_L}-arabinopyranosyl$ hederagenin $28-O-{\beta}-{_D}-glucopyranosyl\;(1{\rightarrow}6)-{\beta}-{_D}-glucopyranoside$ and its 2'-acetate and $3-O-{\beta}-{_D}-glucopyranosyl\;(1{\rightarrow}3)-{\alpha}-{_L}-rhamnopyranosyl\;(1{\rightarrow}2)-{\alpha}-{_L}-arabinopyranosyl$ oleanolic acid and its $28-O-{\beta}-{_D}-glucopyranosyl\;(1{\rightarrow}6)-{\beta}-{_D}-glucopyranoside$.

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Constituents of the Herb of Isodon excisus var. coreanus

  • Kim, Ho-Kyoung;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.20 no.3
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    • pp.291-296
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    • 1997
  • The studies were carried out to evaluate the constituents in the aerial part of Isodon excisus var. coreanus (Labiatae). From the aqueous fraction of methanol extract, compound I (${\alpha}$-[[3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-benzenepropanoic acid), compound II (9-methyl-dihydroferulic acid-4-O-.betha.-D-glucopyranosyl $(1{\rightarrow}2)$-${\alpha}$-L- rhamnopyranosyl (1.rarw.4)-.betha.-D-glucopyranoside), compound III (ent-7.alpha., 11${\alpha}$,15.betha.-trihydroxy-kaur-16-en-1-O-.betha.-D-glucopyranoside) and compound IV ($2{\alpha}$,3${\beta}$,$7{\alpha}$,23-tetrahydroxy-olean-12 -en-28-oic acid 28-O-${\beta}$-D-glucopyranoside) were isolated and identified on the basis of their physicochemical and spectroscopic evidences[IR, FAB(-)MS,$^{1}H-NMR,$$^{13}C-NMR,$$ HMQC$$^{1}H-^{1}H $COSY and HMBC (Heteronuclear Multiple Bond Connectivity)]. Especially, New compounds II and III were named Isodonin A and Isodonin B respectively.

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