• Title/Summary/Keyword: 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).

Content Analysis and Classification for Polygonati Odorati Rhizoma and Polygonati Rhizoma by Steroidal Saponin (Steroidal Saponin을 이용한 위유, 황정의 분류 및 함량 분석법 개발)

  • Kim, Sun-Gun;Shin, So-Young;Moon, Ye-Ji;Seo, Ji-Yoon;Kim, Ho-Kyoung;Whang, Wan-Kyunn
    • YAKHAK HOEJI
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    • v.54 no.6
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    • pp.441-448
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    • 2010
  • In present study, classification and quality control of Genus Polygonatum were developed using the isolated from Polygonati Odorati Rhizoma and Polygonati Rhizoma. 3 components were isolated from Butanol fractions of Polygonati Rhizoma, and 2 components were isolated from Hexane and Butanol fractions of Polygonati Odorati Rhizoma. All the components were obtained using silica gel and ODS column chromatography. The compounds were identified as adenosine, 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside, 22-O-methyl-14-hydrocxyfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-Dgalactopyranosyl-26-O-${\beta}$-D-glucopyranoside, ${\beta}$-Sitosteryl-3-O-${\beta}$-D-D-glucopyranoside, 14-hydoxylfurost-5-ene-3-O-${\beta}$-Dglucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-($1{\rightarrow}3$)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranoside through physicochemical data, spectroscopic methods ($^1H$-NMR, $^{13}C$-NMR, Mass) according references. The quality control of genus Polygonatum were conducted using HPLC quantitative analysis of 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\beta}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside, 14-hydoxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-($1{\rightarrow}3$)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranoside in 30 samples collected throughout Korea and China. This method provided a tool for standardization of mix or misusing the commercial Odorati Rhizoma and Polygonati Rhizoma. As a result, contained quantity of 14-hydroxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-D-galactopyranosyl-26-O-${\beta}$-D-glucopyranoside was measured $0.008{\pm}0.006%$ and 14-hydoxylfurost-5-ene-3-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}2$)-O-[${\beta}$-D-xylopyranosyl-(13)]-O-${\beta}$-D-glucopyranosyl-($1{\rightarrow}4$)-O-${\beta}$-Dgalactopyranoside was measured $0.026{\pm}0.012%$.

Isolation and Identification of Antioxidants from Methanol Extract of Sword Bean (Canavalia gladiata) (작두콩의 메탄올 추출물로부터 항산화 활성 화합물의 분리 및 동정)

  • Kim, Jong-Pil;Lee, Hyang-Hee;Moon, Jae-Hak;Ha, Dong-Ryong;Kim, Eun-Sun;Kim, Jin-Hwan;Seo, Kye-Won
    • Korean Journal of Food Science and Technology
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    • v.45 no.6
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    • pp.777-784
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    • 2013
  • The ethyl acetate (EtOAc) layer of Canavalia gladiata (sword bean) methanol extracts showed higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity than other layers. Four phenolic compounds were isolated from the EtOAc layer by silica gel column chromatography and prep-HPLC using a guided DPPH radical-scavenging assay. The isolated compounds were identified as methyl gallate (1), gallic acid (2), 1,6-di-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (3), and 1,4,6-tri-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (4) based on MS and NMR analyses. Among the four compounds, no. 4 was isolated from this plant for the first time. Their DPPH radical-scavenging activities based on $SC_{50}$ decreased in the following order: 4 (6.9 ${\mu}M$)>3 (8.3 ${\mu}M$)>2 (10.0 ${\mu}M$)>1 (10.3 ${\mu}M$).

Antioxidant Flavonoids from the Twigs of Stewartia koreana

  • Lee, Sa-Im;Yang, Jae-Heon;Kim, Dae-Keun
    • Biomolecules & Therapeutics
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    • v.18 no.2
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    • pp.191-196
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    • 2010
  • In the course of screening for antioxidant compounds by measuring the radical scavenging effect on 1,1-diphenyl- 2-picrylhydrazyl (DPPH), a total extract of the twigs of Stewartia koreana (Theaceae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of six phenolic compounds, ampelopsin (1), catechin (2), proanthocyanidin-A2 (3), fraxin (4), (2R, 3R)-taxifolin-3-${\beta}$-D-glucopyranoside (5), and (2S, 3S)-taxifolin-3-${\beta}$-D-glucopyranoside (6), as active principles. Their structures were elucidated by spectroscopic studies. Compounds 1-6 were isolated for the first time from this plant. Among them, three compounds 1-3 showed the significant antioxidative effects on DPPH, and riboflavin originated superoxide quenching activity. In riboflavin-nitrobluetetrazolium (NBT)-light system, compound 1 showed better superoxide quenching activity than vitamin C.

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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A New Alkyl Alcohol Glycoside from Chrysanthemi Flos (감국(Chrysanthemi Flos)의 새로운 알킬알콜배당체 성분에 관한 연구)

  • Jung, Keun-Young;Oh, Sei-Ryang;Kim, Chun-Suk;Kim, Jung-Hee;Lee, Hyeong-Kyu
    • Korean Journal of Pharmacognosy
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    • v.27 no.1
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    • pp.15-19
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    • 1996
  • In the course of phytochemical studies of Chrysanthermi Flos(Chrysanthemum indicum L., Compositae), two compounds were isolated by repeated column chromatography. Compound 1 is identified as adenosine on the basis of spectroscopic means and comparison with an authentic standard. Compound 2 is determined to be a new alkyl alcohol glycoside, 1-octen-3-ol $3-O-{\beta}-D-xylopyranosyl(1{\rightarrow} 6)-{\beta}-D-glucopyranoside$ on the spectroscopic evidence. Compounds 1 and 2 are reported for the first time from this plant.

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Phytochemical Constituents from Aconitum pseudolaeve Var. erectum (진범의 식물화학적 성분)

  • Kim, Dae-Keun;Kwak, Jong-Hwan;Song, Ki-Won;Kwon, Hack-Cheol;Zee, Ok-Pyo;Lee, Kang-Ro
    • Korean Journal of Pharmacognosy
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    • v.27 no.1
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    • pp.75-79
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    • 1996
  • Four steroids and one flavonol glycoside were isolated from the ethanol extract of the whole plant of Aconitum pseudolaeve var. erectum. Their structures were identified as ${\beta}-sitost-4-en-3-one$, 22-dihydro-stigmast-4-en-3,6-dione, ${\beta}-sitosterol$, ${\beta}-sitosterol-3-O-{\beta}-D-glucopyranoside$ and $kaempferol-3-O-{\beta}-D-glucopyranoside(astragalin)$ on the basis of spectral data.

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Superoxide Quenching Activity of Phenolic Compounds from the Whole Plant of Galium verum var. asiaticum

  • Kim, Dae-Keun
    • Natural Product Sciences
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    • v.17 no.4
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    • pp.261-266
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    • 2011
  • During the process of screening for antioxidative effects of natural plants in Korea, by measuring the superoxide quenching activity, methanol extract of the whole plant, Galium verum var. asiaticum (Rubiaceae), was found to show potent antioxidant activity. Subsequent activity-guided fractionation of methanol extract of Galium verum var. asiaticum led to the isolation of five phenolic compounds. Using spectroscopic techniques, the chemical structures were elucidated as: caffeic acid (1), narcissin (2), rutin (3), luteolin-7-O-${\alpha}$-L-rhamnopyranosyl (1 ${\rightarrow}$ 2)-${\beta}$-D-glucopyranoside (4), and luteolin-7-O-${\beta}$-D-glucopyranoside (5). These compounds were isolated for the first time from this plant. Among them, compound 1 showed the most significant riboflavin-originated superoxide and xanthine-originated superoxide quenching activities. Compounds 3 and 4 exhibited mild superoxide quenching effects compared with vitamine C.

Phytochemical Constituents of Thesium chinense TURCZ and Their Cytotoxic Activities In Vitro

  • Lee, Il-Kyun;Kim, Ki-Hyun;Choi, Sang-Un;Lee, Jae-Hyun;Lee, Kang-Ro
    • Natural Product Sciences
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    • v.15 no.4
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    • pp.246-249
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    • 2009
  • Column chromatographic separation of the MeOH extract from the aerial parts of Thesium chinense TURCZ led to the isolation of two norsesquiterpenes (1 - 2), two phenylpropanes (3 - 4) and four flavonoids (5 - 8). Their structures were determined by spectroscopic means to be 5,6-epoxy-3-hydroxy-7-megastigmen-9-ene (1), (-)-loliolide (2), methyl-p-hydroxycinnamate (3), methyl caffeate (4), kaempferol (5), kaempferol-3-O-${\beta}$-Dglucopyranoside (6), kaepmferol-3,7-di-O-${\beta}$-D-glucopyranoside (7) and kaempferol-3-O-${\beta}$-D-glucopyranoside-6''-(3-hydroxy-3-methylglutarate) (8). Compounds 1 - 4, 7 and 8 were first isolated from this source. The isolated compounds were evaluated for their cytotoxicty in vitro using the sulforhodamin B bioassay (SRB).