• Title/Summary/Keyword: glucoside

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Isolation of Phytochemicals from Salvia plebeia Using Countercurrent Chromatography Coupled with Reversed-phase HPLC

  • Kil, Hyun Woo;Rho, Taewoong;Seo, Young Ju;Yu, Aram;Yoon, Kee Dong
    • Natural Product Sciences
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    • v.26 no.3
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    • pp.236-243
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    • 2020
  • Salvia plebeia R. Br. is a plant which has been used as an edible crop and traditional medicine in Asian countries. In this study, HPLC-PDA analysis and countercurrent chromatography (CCC) coupled with reversed-phase (RP) HPLC method were applied to isolate ten isolates from 3.3 g of n-butanol soluble extract from hot-water extract of S. plebeia. The use of CCC enabled us to efficiently fractionate the starting material with less sample loss and facilitate the isolation of compounds from S. plebeia extract using RP-HPLC. The isolates were determined to be caffeic acid (1), 6-hydroxyluteolin 7-O-β-D-glucoside (2), eudebeiolide B (3), (R)-rosmarinic acid (4), homoplantaginin (5), eudebeiolide D (6), plebeiolide C (7), salpleflavone (8), eupafolin (9) and hispidulin (10) based on the spectroscopic evidence.

Biochemical Characterization of an ABC Transporter Gene Involved in Cephabacin Biosynthesis in Lysobacter lactamgenus

  • Park, Myoung-Jin;Yon, Jei-Oh;Lim, Si-Kyu;Ryu, Dewey D.-Y.;Nam, Doo-Hyun
    • Journal of Microbiology and Biotechnology
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    • v.14 no.3
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    • pp.635-638
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    • 2004
  • An ATP-binding-cassette (ABC) transporter gene in the cephabacin biosynthetic gene cluster of Lysobacter lactamgenus was characterized. The amplified orf10 (cpbJ) gene was subcloned into pET-28a(+) vector and expressed in E. coli BL21(DE3) strain by 0.5 mM IPTG at $30^{\circ}C$. The membrane fraction of recombinant E. coli cells was separated by ultracentrifugation, and solubilized using 2.5% octyl-$\beta$-D-glucoside. Using the solubilized membrane fraction, the artificial proteoliposomes were reconstituted and analyzed for the biological activity of CpbJ protein. Upon measuring ATPase activity, the proteoliposome made from recombinant E. coli membrane proteins showed slightly higher activity than that from host E. coli membrane proteins. In the measurement of membrane transport activity, the reconstituted proteoliposome of recombinant E. coli membrane proteins exhibited higher activity when both substrates of cephalosporin C and L-Ala-L-Ser were applied, compared to the case of cephalosporin C or L-Ala-L-Ser only. It implies that the CpbJ protein is an ABC transporter secreting cephabacin antibiotics synthesized in cytoplasm.

Anti-Oxidative and Anti-Inflammatory Effects of QGC in Cultured Feline Esophageal Epithelial Cells

  • Lee, Myeong Jae;Song, Hyun Ju;Jeong, Jun Yeong;Park, Sun Young;Sohn, Uy Dong
    • The Korean Journal of Physiology and Pharmacology
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    • v.17 no.1
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    • pp.81-87
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    • 2013
  • Quercetin-3-O-${\beta}$-D-glucuronopyranoside (QGC) is a flavonoid glucoside extracted from Rumex Aquaticus Herba. In the present study, anti-oxidative and anti-inflammatory effects of QGC were tested in vitro. Epithelial cells obtained from cat esophagus were cultured. When the cells were exposed to acid for 2 h, cell viability was decreased to 36%. Pretreatment with 50 ${\mu}M$ QGC for 2 h prevented the reduction in cell viability. QGC also inhibited the productions of intracellular ROS by inflammatory inducers such as acid, lipopolysaccharide, indomethacin and ethanol. QGC significantly increased the activities of superoxide dismutase (SOD) and catalase, and also induced the expression of SOD2, while it restored the decrease of catalase expression in cells exposed to acid. QGC inhibited NF-${\kappa}B$ translocation, cyclooxygenase-2 expression and $PGE_2$ secretion in cells exposed to acid, which plays an important role in the pathogenesis of esophagitis. The data suggest that QGC may well be one of the promising substances to attenuate oxidative epithelial cell injury and inflammatory signaling in esophagus inflammation.

대두와 인체생리(2)-대두 이소플라본의 체내흡수

  • Kim, Seong-Ran
    • Bulletin of Food Technology
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    • v.14 no.4
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    • pp.3-12
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    • 2001
  • 이소플라본은 대두와 대두가공제품에 들어있으며 화학적으로 두가지 형태 즉 아글리콘(aglycone)과 배당체(glucoside)로 존재한다. 본 논문은 사람에게 대두의 이소플라본이 흡수되는데 아글리콘과 배당체가 차이가 있는지를 연구하였다. 이소플라본을 저농도(0.11mmol)로 1회 투여했을 때 아글리콘형은 섭취 2시간 후에 혈장의 이소플라본 농도가 최고치에 도달하였으며 배당체형은 섭취 4시간 후에 최고치에 도달하였다: 이때 피험자는 4명의 남성(41세)과 4명의 여성(45세) 이었다. 또한 8명의 피험자〔남성 4명(40세), 여성 4명(47세)〕를 대상으로 고농도(1.7mmol) 이소플라본을 1회 섭취시킨 후 혈장의 이소플라본 농도 변화를 비교하였으며, 아글리콘 섭취 후 혈장 이소플라본의 최고 농도는 배당체로 섭취한 경우보다 5배가 높았다. 저농도와 고농도의 두 실험에서 모두, 제니스테인과 다이드제인의 섭취수준은 유사함에도 불구하고 혈장의 제니스테인의 농도가 다이드제인보다 유의적으로 높았다. 또한 8명의 남성(45세)을 대상으로 4주간의 장기간 이소플라본(0.30mmol/ 일)을 섭취시킨 후 혈장의 이소플라본 농도를 측정하였다. 2주와 4주째에 혈장내 농도는 배당체형보다 아글리콘 섭취 후에 100% 이상 높은 것으로 나타났다. 이소플라본 아글리콘은 배당체보다 사람에게 더 빠르고 더 많은 량이 흡수되었다. 이소플라본 아글리콘이 풍부한 제품은 이소플라본 배당체가 풍부한 제품보다 관상 심장질환 등 만성질환 예방에 더 효과적일 수 있을 것이다.

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Antioxidant Caffeic acid Derivatives from Leaves of Parthenocissus tricuspidata

  • Saleem, Muhammad;Kim, Hyoung-Ja;Jin, Changbae;Lee, Yong-Sup
    • Archives of Pharmacal Research
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    • v.27 no.3
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    • pp.300-304
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    • 2004
  • Five caffeic acid derivatives; methyl ester of caffeoylglycolic acid (1), dimethyl ester of caffeoyltartaric acid (2), dimethyl ester of caffeoyltartronic acid (3), monomethyl ester of caffeoyltartronic acid (4), methyl ester of caffeic acid (5), and some other secondary metabolites including; quercetin, quercetin 3-O-$\beta$-D-glucuronide methyl ester, kaempferol, 3,5,7,4'-O-tetramethylkaempferol, $\beta$-sitosterol glucoside, 2$\alpha$-hydroxyursolic acid and 2,24-dihydroxyursolic acid, have been isolated and characterized. All the isolated compounds were characterized with the help of NMR spectroscopy and mass spectrometry. Structure of compound 3 was also confirmed by a single X-ray crystallographic technique. Isolates were evaluated for anti-oxidant activities and most of the tested compounds were found to be potent in DPPH free radical scavenging ($IC_{50}{\;}={\;}4.56-14.17{\;}{\mu\textrm{g}}/mL$) and superoxide anion scavenging ($IC_{50}{\;}={\;}0.58-7.39{\;}{\mu\textrm{g}}/mL$) assays.

Cytotoxic Phenolic Constituents of Acer tegmentosum Maxim

  • Park, Ki-Myun;Yang, Min-Cheol;Lee, Kyu-Ha;Kim, Kyung-Ran;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.29 no.12
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    • pp.1086-1090
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    • 2006
  • The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.

Physico-Chemical Properties of Pseudoceramide in Relation to Bilayer-Forming

  • Jeong, Min-Woo;Oh, Seong-Geun;Kim, Do-Hoon;Kang, Hak-Hee
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.27 no.1
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    • pp.3-15
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    • 2001
  • The bilayer forming ability of pseudo-ceramide PC104 in octanoic acid/water/n-octyl $\beta$-D-glucoside mixtures was investigated through the phase diagram. Because of its low solubility in water and of its crystallization, pseudoceramide PC104 was dissolved in octanoic acid, which is nontoxic additive for foods and cosmetics. The mixtures formed four different phases (L1, L2, LC and two phases). Depending on the concentration of PC104 in octanoic acid, the region of each phase was extended or contracted. On the contrary to the region of L2, regions of lamellar phase and L1 phase were expanded. The bilayer-forming ability of PC104 was explained on the basis of concentration of PC104 at interface and interaction between PC104 and octanoic acid. From FT-IR results, it was found that the interactions of PC104’s polar head group with octanoic acid increased as the amount of PC104 in octanoic acid increased. Also emulsion size and size distribution have been studied depending upon the emulsification path. droplets of emulsion prepared from lamellar phase were smaller and more homogeneous compared to those of emulsions formed from L2 phase.

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Isolation of Isoprenoidal Compounds from the Stems of Acer tegmentosum Max (산겨릅나무 줄기에서 이소프렌계 화합물의 분리)

  • Hur, Jong-Moon;Jun, Mi-Ra;Yang, Eun-Ju;Choi, Sun-Ha;Park, Jong-Cheol;Song, Kyung-Sik
    • Korean Journal of Pharmacognosy
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    • v.38 no.1
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    • pp.67-70
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    • 2007
  • The stems of Acer tegmentosum Max were extracted with MeOH and then partitioned with $CH_2Cl_2$, n-BuOH, and $H_2O$, successively. Three compounds were isolated from the $CH_2Cl_2$ fraction through repeated column chromatographic separation. Their chemical structures were elucidated as ${\beta}$-sitosterol, ${\beta}$-sitosterol-3-O-${\beta}$-D-glucoside, and epifriedelinol by comparison of spectral data with those in references. These three compounds were firstly isolated from this plant.

Simultaneous Quantitation of Nine Constituents of Fraxinus rhynchophylla using High Performance Liquid Chromatography - Diode Array Detector

  • Ahn, Jong Hoon;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Natural Product Sciences
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    • v.19 no.3
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    • pp.236-241
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    • 2013
  • A high-performance liquid chromatography-diode array detector (HPLC-DAD) method was established for quantitative evaluation of nine constituents of Fraxinus rhynchophylla such as four coumarins, esculin (1), fraxin (2), esculetin (3), fraxetin (4), three lignans, syringaresinol 4,4'-O-${\beta}$-diglucoside (5), pinoresinol 4-O-${\beta}$-glucoside (6), pinoresinol (9), one secoiridoid, oleuropein (7), and one coumarinolignan, cleomiscosin C (8). The preferred chromatographic condition was obtained on Phenomenex Gemini-NX (3 ${\mu}m$, C18 110A, $150{\times}4.60$ mm) and the mobile phase was composed of water and acetonitrile using a gradient elution. The wavelength was set at 220 nm. Extraction condition of these constituents in F. rhynchophylla was also optimized through extraction time, extraction solvent and extraction method using established method. From this study, extraction at $70^{\circ}C$ with the mixture of ethanol and water for more than 12 h was suggested to be good extraction condition for these constituents. Quantitation of nine constituents in different F. rhynchophylla samples was also successfully accomplished with the newly established method.

Phytochemical Constituents of Phyllanthus urinaria

  • Cha, Joon Min;Park, Jong Eel;Choi, Sang Un;Lee, Kang Ro
    • Natural Product Sciences
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    • v.26 no.2
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    • pp.151-157
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    • 2020
  • Extensive column chromatography separation of the MeOH extract from the aerial parts of Phyllanthus urinaria afforded seventeen compounds (1 - 17). The structures of the compounds were elucidated by physicochemical and spectroscopic methods to be 5'-β-D-glucopyranosyloxyjasmonic butyl ester (1), (+)-cucurbic acid (2), dendranthemoside B (3), boscialin 4'-O-β-D-glucoside (4), 4,5-dihydroblumenol A (5), (6R,9R)-megastigman-4-ene-9,13-diol (6), (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (7), (6S,9R)-roseoside (8), mallophenol B (9), icariside B5 (10), corchoinoside B (11), canangaionoside (12), 5,6-epoxy-3-hydroxy-7-megastigmen-9-one (13), icariside B2 (14), (7E)-2β,3β-dihydroxy-megastigm-7-en-9-one (15), betulalbuside A (16), and loliolide (17). The compounds 1, and 3 - 16 were isolated for the first time from this plant. The absolute stereochemistry of compound 1 was newly determined. The isolated compounds were tested for cytotoxic activity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay, but all the compounds showed weak cytotoxic activities.