• Title/Summary/Keyword: $ethyl-{\beta}-D-glucopyranoside$

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Sterols from the Seed of Cowpea (Vigna sinensis K.) (동부로부터 sterol의 분리 동정)

  • Cui, En-Ji;Park, Hee-Jung;Wu, Qian;Chung, In-Sik;Kim, Ji-Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.53 no.2
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    • pp.77-81
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    • 2010
  • The seed of cowpea (Vigna sinensis K.) was extracted with 80% aqueous methanol (MeOH). And the concentrated extract was partitioned with ethyl acetate (EtOAc), n-butanol (n-BuOH) and $H_2O$, successively. The repeated silica gel and octadecyl silica gel (ODS) column chromatographic separations for the EtOAc and n-BuOH fractions led to isolation of four sterols. And the chemical structures of the compounds were determined as a mixture of stigmasterol and $\beta$-sitosterol with the ratio of 4 to 3 (1), 7-ketositosterol (2), and stigmasterol 3-O-$\beta$D-glucopyranoside (3) from the interpretation of spectroscopic data including nuclear magnetic resonance (NMR) spectrum metric, mass (MS) spectrum metric and infrared (IR) spectroscope. This study reports the first isolation of $\beta$-sitosterol, 7-ketositosterol, and stigmasterol 3-O-$\beta$-D-glucopyranoside from the seed of Vigna sinensis K. In addition, compound 2, 7-ketositosterol, is rarely occurred in natural source including plant.

DPPH Free Radical Scavenging Effect of the Aerial Parts of Desmodium oldhami (큰도둑놈의갈고리 지상부의 DPPH Free Radical 소거효과)

  • Yang, Seo-Kwon;Park, Sae-Rom;Ahn, Dal-Rae;Yang, Jae-Heon;Cho, Chong-Hyeon;Hwang, Yong-Hun;Park, Jong-Han;Kim, Dae-Keun
    • Korean Journal of Pharmacognosy
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    • v.41 no.3
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    • pp.180-184
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    • 2010
  • The antioxidant activity of Desmodium oldhami (Leguminosae) was determined by measuring the radical scavenging effect on DPPH (1,1-diphenyl-2-picrylhydrazyl). The methanolic extract of D. oldhami showed the strong antioxidant activity. Five compounds, kaempferol-3-O-rhamnopyranoside (afzeline) (1), quercetin-3-O-[$\alpha$-L-rhamnopyranosyl($1{\rightarrow}6$)-$\beta$-Dglucopyranoside] (rutin) (2), kaempferol-3-O-glucopyranoside (astragalin) (3), genistein-7-O-$\beta$-D-glucopyranoside (genistin) (4), kaempferol-3-O-rutinoside (5) were isolated from the active ethyl acetate soluble fraction of D. oldhami through repeated silica gel and Sephadex LH-20 column chromatography. Among them, compound 2 showed the most significant antioxidative effect on DPPH free radical scavenging test. Compounds 1-5 are reported for the first time from this plant.

Studies on the Chemical Constituents Biological Activities of Mulberry Extracts (오디(Mulberry) 추출물의 성분분석 및 생리활성에 관한 연구)

  • Lee, Sang-Keug;Lee, Hak-Ju;Kang, Ha-Youg;Choi, Don-Ha;Jo, Hyun-Jin;Lee, Tae-Seong
    • Journal of the Korean Wood Science and Technology
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    • v.37 no.1
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    • pp.105-113
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    • 2009
  • The freezed Mulberry (10 kg) was extracted with 80% EtOH, concentrated, and fractionated with a series of n-hexane, ethyl acetate, and water on a separatory funnel. A portion of ethyl acetate soluble (22 g) was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol as eluents. The isolated compounds were identified by cellulose TLC, $^1H-$,$^{13}C$-NMR, FAB, and EI-MS. Quercetin-3-O-${\beta}$-D-glucopyranoside (Compound I), protocatechuic acid (Compound II), p-hydroxybenzoic acid (Compound III) were isolated from the ethyl acetate soluble fraction. In antioxidative activities of the fractionated extractives using DPPH radical scavenging test, EtOAc and water soluble fractions indicated better than BHT as contro and in in vitro tests using MTT assay, there was no cytotoxicity. Also, tyrosinase inhibition and anticancer activities were not so good, but there may be a potential as a cosmetic raw material because the cell extension effect was excellent.

Effects of the Constituents of Melonis Pedicellus in the Animal Models of Hepatic Diseases (과체 성분의 간질환 모델에서의 효과)

  • 최선희;이석용;조태순
    • YAKHAK HOEJI
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    • v.44 no.1
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    • pp.87-94
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    • 2000
  • In order to investigate the hepatoprotective constituents, Melonis Pedicellus was systematically extracted and fractionated with n-hexane, ethyl acetate, butanol and water Treatment of rats with ethyl acetate fraction reduced hepatic injuries induced by $\alpha$-naphthylisothiocyanate or D-galactosamine, whereas the components in water fraction showed protective effect only against D-galactosamine-induced hepatitis in rats. Two cucurbitacins and three sterols were isolated from ethylacetate fraction and their chemical structures were identified as cucurbitacin B, isocucurbitacin B, $\alpha$-spinasterol, stigmast-7-en-3-ol and stigmast-7-en-3-ol-0-$\beta$-D-glucopyranoside. Cucurbitacin B at the dose of 1 mg/kg (p.o.) signifcantly increased in bile flow in rats with ANIT-induced cholestasis. Isocucurbitacin B at 5 mg/hg (p.o.) showed signilicant protective effects against ANIT-induced cholestasis. These results showed that cucurbitacin B and isocucurbitacin B from Melonis Pedicellus may have hepatoprotective effect in rats with experimental cholestasis.

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Quantitative Determination of Compounds from Akebia quinata by High-Performance Liquid Chromatography

  • Yen, Nguyen Thi;Thu, Nguyen Van;Zhao, Bing Tian;Lee, Jae Hyun;Kim, Jeong Ah;Son, Jong Keun;Choi, Jae Sui;Woo, Eun Rhan;Woo, Mi Hee;Min, Byung Sun
    • Bulletin of the Korean Chemical Society
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    • v.35 no.7
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    • pp.1956-1964
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    • 2014
  • To provide the scientific corroboration of the traditional uses of Akebia quinata (Thunb.) Decne., a detailed analytical examination of A. quinata stems was carried out using a reversed-phase high performance liquid chromatography (RP-HPLC) method coupled to photodiode array detector (PDA) for the simultaneous determination of four phenolic substances; cuneataside D (1), 2-(3,4-dihydroxyphenyl)ethyl-O-${\beta}$-D-glucopyranoside (2), 3-caffeoylquinic acid (3) and calceolarioside B (4). Particular attention was focused on the main compound, 3-caffeoylquinic acid (3), which has a range of biological functions. In addition, 2-(3,4-dihydroxyphenyl)ethyl-O-${\beta}$-D-glucopyranoside (2) was considered as a discernible marker of A. quinata from its easy confuse plants. The contents of compounds 2 and 3 ranged from 0.72 to 2.68 mg/g and from 1.66 to 5.64 mg/g, respectively. The validation data indicated that this HPLC/PDA assay was used successfully to quantify the four phenolic compounds in A. quinata from different locations using relatively simple conditions and procedures. The pattern-recognition analysis data from 53 samples classified them into two groups, allowing discrimination between A. quinata and comparable herbs. The results suggest that the established HPLC/PDA method is suitable for quantitation and pattern-recognition analyses for a quality evaluation of this medicinal herb.

Cytotoxic Chemical Constituents from the Mushroom of Pholiota adiposa

  • Chung, Ill-Min;Kong, Won-Sik;Lee, Oh-Kyu;Park, Jeong-Sik;Ahmad, Ateeque
    • Food Science and Biotechnology
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    • v.14 no.2
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    • pp.255-258
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    • 2005
  • The compounds, 1-Linoleic-2-olein (1), stigmasterol (2), 1,4-glucopyranosyl-1',4'-glucopyranosyl-1",4"-glucopyranoside (3), 2',3'-diphosphoryl-1'-propanoxy-${\beta}$-D-glucopyranoside (4), 1-Linoleic-3-olein (5), l-(N,N,N-trimethyl ethyl amino phosphoryl)-2,3-dilinolein ion (6) and glyceryl phosphate (7) were isolated and identified from the Mushroom of Pholiota adiposa for the first time by column chromatography, TLC, UV, IR, $^1H$ and $^{13}C$ NMR, EI-MS, and FAB-MS. The compounds 1 and 2 were found to have weak cytotoxicity against P388 murine leukemia cells. However, the compounds 6 and 7 did not show any cytotoxicity.

Isolation and Characterization of Antioxidative Compounds from the Aerial Parts of Angelica keiskei

  • Kim, So-Joong;Cho, Jeong-Yong;Wee, Ji-Hyang;Jang, Mi-Young;Kim, Cheol;Rim, Yo-Sup;Shin, Soo-Cheol;Ma, Seung-Jin;Moon, Jae-Hak;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.14 no.1
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    • pp.58-63
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    • 2005
  • Ethyl acetate-soluble neutral fraction of hot water extracts from the aerial parts of Angelica keiskei showed a 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity. Six antioxidative compounds were purified and isolated by various chromatographic procedures. Based on the analyses of FAB-MS and NMR, the isolated compounds were structurally elucidated as luteolin 7-O-${\beta}$-D-glucopyranoside (1), quercetin 3-O-${\beta}$-D-galactopyranoside (2), quercetin 3-O-${\beta}$-D-glucopyranoside (3), quercetin 3-O-${\alpha}$-D-arabinopyranoside (4), kaempferol 3-O-${\alpha}$-D-arabinopyranoside (5), and luteolin 7-O-rutinoside (6). The glycosides of flavonols and luteolin showed DPPH radical-scavenging activity. One molecule of 2, 3, 4, 6, 1, and 5 scavenged 4.2, 4.2, 4.1, 2.5, 2.2, and 1.4 molecules of DPPH radical, respectively.

Cyclofarnesane sesquiterpene glucoside from the whole plant of Loranthus tanakae and its cytotoxicity ('꼬리겨우살이'(Loranthus tanakae) 전초로부터 cyclofarnesane sesquiterpene glucoside의 분리 동정 및 세포독성)

  • Joo, Sun-Woo;Kim, Hyoung-Geun;Oh, Eun-Ji;Ko, Jung-Hwan;Lee, Yeong-Geun;Kang, Se-Chan;Lee, Dae Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.62 no.1
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    • pp.7-10
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    • 2019
  • The whole plants of Loranthus tanakae were repeatedly extracted with 80% aqueous MeOH and the concentrate was partitioned into ethyl acetate (EtOAc), n-butyl alcohol (n-BuOH) and $H_2O$ fractions. The repeated silica gel ($SiO_2$), octadecyl $SiO_2$ (ODS), and Sephadex LH-20 column chromatographies for the n-BuOH fraction led to isolation of a cyclofarnesane sesquiterpene glucoside. The chemical structure including stereo structure was determined to be a (1'R,3'S,5'R,8'S,2E,4E)-dihydrophaseic acid $3^{\prime}-O-{\beta}-{\text\tiny{D}}$-glucopyranoside on the basis of spectroscopic analyses. This compound was isolated for the first time from L. tanakae in this study. Compound 1 showed a moderate dose-dependent cytotoxicity against human Caucasian gastric adenocarcinoma cells and human hepatocyte cari-noma cells cell lines at higher than $50{\mu}g/mL$.

Phenolic Compounds from Capsiccum annuum Leaves Showing Radical Scavenging Effect (고추 잎에서 라디칼소거활성을 가지는 페놀성 화합물의 분리)

  • Choi, Jang-Gi;Hur, Jong-Moon;Cho, Hyun-Woo;Park, Jong-Cheol
    • Korean Journal of Pharmacognosy
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    • v.38 no.3 s.150
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    • pp.258-262
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    • 2007
  • In the present study, we investigated the antioxidant activity of methanol extract and its organic fractions (n-hexane, $CH_2Cl_2$, EtOAc, n-BuOH and $H_2O$) of Capsiccum annuum leaves against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. As results, methanol extract, and its ethyl acetate and n-butanol fractions showed good scavenging effect at 100 ${\mu}g/ml$. Four compounds were isolated from the ethyl acetate fraction through silica gel and Sephadex LH-20 column chromatographies. Their chemical structures were elucidated as apigenin (1), vanillic acid (2), uracil (3) and apigenin $7-O-{\beta}-D-apiofuranosyl(1{\rightarrow}2)-{\beta}-D-glucopyranoside$ (4) by comparison of spectral data with those in reference. $IC_{50}$ value of compound 2 was 14.7 ${\mu}g/ml$, while compounds 1, 3 and 4 had no effect on the DPPH radical.

Antioxidative Activity and Component Analysis of Cayratia japonica Extract (오렴매 추출물의 항산화 활성, 성분 분석)

  • Yang, Hee-Jung;Kim, Eun-Hee;Park, Soo-Nam
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.34 no.2
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    • pp.117-127
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    • 2008
  • In this study, the antioxidative effects, inhibitory effects on elastase, and components of Cayratia japonica extracts were investigated. The free radical(1,1-diphenyl-2-picrylhydrazyl, DPPH) scavenging activities($FSC_{50}$) of extract/fractions of Cayratia japonica were in the order: 50% ethanol extract(114.3 ${\mu}g/mL$)${\mu}g/mL$)${\mu}g/mL$). Reactive oxygen species(ROS) scavenging activities($OSC_{50}$) of some Cayratia japonica extracts in $Fe^{3+}-EDTA/H_2O_2$ system were investigated using the luminol-dependent chemiluminescence assay. The order of ROS scavenging activities were deglycosylated flavonoid aglycone fraction($OSC_{50},\;3.30{\mu}g/mL$)<50% ethanol extract(1.21 ${\mu}g/mL$)${\mu}g/mL$). Ethyl acetate fraction showed the most prominent scavenging activity. The protective effects of extract/fractions of Cayratia japonica on the rose-bengal sensitized photohemolysis of human erythrocytes were investigated. The Cayratia japonica extracts suppressed photohemolysis in a concentration dependent manner($1{\sim}25{\mu}g/mL$), particularly deglycosylated flavonoid aglycone fraction exhibited the most prominent celluar protective effect(${\tau}_{50}$, 175.05min at 25 ${\mu}g/mL$). Aglycone fractions obtained from the deglycosylation reaction of ethyl acetate fraction among the Cayratia japonica extracts, showed 2 bands in TLC and 2 peaks in HPLC experiments(360 nm). Two components were identified as luteolin(composition ratio, 47.50%), apigenin(52.50). TLC chromatogram of ethyl acetate fraction of Cayratia japonica extract revealed 3 bands and HPLC chromatogram showed 4 peaks, which were identified as luteolin-7-O-${\beta}$-D-glucopyranoside(composition ratio, 11.14%), apigenin-7-O-${\beta}$-D-glucuronopyranoside(15.38%), luteolin(23.55%) and apigenin(49.92%) in the order of elution time. The inhibitory effect of aglycone fraction on elastase($IC_{50},\;70.5{\mu}g/mL$) was very high. These results indicate that extract/fractions of Cayratia japonica can function as antioxidants in biological systems, particularly skin exposed to UV radiation by scavenging $^1O_2$ and other ROS, and protect cellular membranes against ROS. And component analysis of Cayratia japonica extract and antioxidative effects could be applicable to new cosmetics.