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

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Degradation of Lignin and Cellulose Model Compounds by Chlorine Dioxide

  • Yoon, Byung-Ho;Lee, Seon-Ho;Wang, Li-Jun
    • Journal of Korea Technical Association of The Pulp and Paper Industry
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    • v.31 no.2
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    • pp.1-7
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    • 1999
  • In this paper, five lignin model compounds (vanilly alcohol, veratryl alcohol, veratryl methyl carbinol, biseugenol) and three cellulose model compounds (${\alpha}$-D-glucos, methyl-${\beta}$-D-glucopyra-noside, D-cellobiose) were used to study the degradation rates of lignin and cellulose with chlorine dioxide. Biseugenol, which has unsaturated structure on the side chain of aromatic ring, was found to react with chlorine dioxide very quickly and consume large amount of chlorine dioxide. Phenolic structures, represented by veratryl alcohol and apocynol, react with chlorine dioxide much faster than nonphenolic structures represented by veratryl alcohol and veratryl methyl carbinol. The degradations of cellulose models were generally very slight, the corder of reaction rate being ${\alpha}$-D-glucose > D-cellobiose > methyl-${\alpha}$-D-glucopyranoside.

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Whitening and Anti-inflammatory Constituents from the Extract of Citrullus lanatus Vines (수박 덩굴 추출물 유래 미백 및 항염 활성 성분)

  • Jeon, Ah Lim;Kim, Jung Eun;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.43 no.1
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    • pp.53-60
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    • 2017
  • In this study, we investigated whitening and anti-inflammatory constituents from a watermelon (Citrullus lanatus, C. lanatus) vines (leaves and stems). As anti-melanogenesis and anti-inflammatory activities were screened for the ethanol extract and solvent fractions, n-hexane (n-Hex) and ethyl acetate (EtOAc) fractions showed the most potent activities. Three constituents were isolated from the n-Hex and EtOAc fractions of C. lanatus; ${\alpha}-linolenic$ acid (1), sigmast-7-en-O-${\beta}$-D-glucopyranoside (2), 1-feruloyl-${\beta}$-D-glucopyrinoside (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literature values. Whitening and anti-inflammatory effects were studied for the isolated compounds. Upon the anti-melanogenesis tests using ${\alpha}-MSH$ stimulated B16F10 melanoma cells, the compounds 1 and 3 inhibited the cellular melanogenesis and intracellular tyrosinase activities effectively. For the anti-inflammation tests using lipopolysaccharide (LPS)-induced RAW 264.7 cells, the isolates 1 and 3 were determined to decrease the production of nitric oxide (NO) and pro-inflammatory cytokines ($TNF-{\alpha}$, IL-6). Based on these results, C. lanatus vines extract could be potentially applicable as whitening and anti-inflammatory ingredients in cosmetic formulations.

Constituents of the Stems and Fruits of Opuntia ficus-indica var. saboten

  • Lee, Eun-Ha;Kim, Hyoung-Ja;Song, Yun-Seon;Jin, Chang-Bae;Lee, Kyung-Tae;Cho, Jung-Sook;Lee, Yong-Sup
    • Archives of Pharmacal Research
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    • v.26 no.12
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    • pp.1018-1023
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    • 2003
  • From the stems and fruits of Opuntia ficus-indica var. saboten, eight flavonoids, kaempferol (1), quercetin (2), kaempferol 3-methyl ether (3), quercetin 3-methyl ether (4), narcissin (5), (+)-dihydrokaempferol (aromadendrin, 6), (+)-dihydroquercetin (taxifolin, 7), eriodictyol (8), and two terpenoids, (6S,9S)-3-oxo-$\alpha-ionol-\beta$-D-glucopyranoside (9) and corchoionoside C (10) were isolated and identified by means of chemical and spectroscopic. Among these isolates, compounds 3∼5 and 8∼10 were reported for the first time from the stems and fruits of O. ficusindica var. saboten.

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.

Chemical Constituents of the Leaves of Staphylea bumalda

  • Sohn, Soon-Joo;Kwon, Yong-Soo;Kim, Sung-Soo;Chun, Wan-Joo;Kim, Chang-Min
    • Natural Product Sciences
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    • v.10 no.4
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    • pp.173-176
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    • 2004
  • Six compounds were isolated from the BuOH soluble fraction of the leaves of Staphylea bumalda. On the basis of spectral data, they were identified as atragalin (1), $2-methyl-5,\;7-dihydroxy-chromone-7-O-{\beta}-D-glucopyranoside$ (2), isoquercitrin (3), nicotiflorin (4), kaempferol 3-neohesperidoside (5), kaempferol $3-O-[{\alpha}-rhamno-pyranosyl-(1\;{\to}\;4)-rhamnopyranosyl-(1\;{\to}\;6)-{\beta}-D-glucopyranoside]$ (6), respectively.

Chemical constituents of Synurus deltoides (Aiton)Nakai

  • Lee, Hyun-Yong;Jin, Wen-Yi;An, Ren-Bo;Na, Min-Kyun;Bae, Ki-Hwan
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.375.2-375.2
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    • 2002
  • S.deltoides (Compositae) distributed widely in Korea. China. It is edible as a food additive. but there has been no study on chemical constituents. Therefore. we isolated nine compounds from S.deltoldes. On the basis of spectroscopic evidence. the structure of these compounds were characterized as lupeol( 1), $\alpha$-amyrin(2).$\beta$-amyrin (3), ursolic acid(4), nonacosanol(5), nonacosanoic acid(6). mixture of $\beta$-sitosterol. stigmasterol and campesterol (7), $\beta$-sitosteryl-3-O-$\beta$-D-glucopyranoside(8), stigmasteryI-3-O-$\beta$-D-glucopyranoside(9). (omitted)

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Flavonoids from the Leaves of Alnus Maximowiczii Call (두메오리나무 잎의 플라보노이드 화합물)

  • 안경환;도상학;정동욱;김준식;조수민;이민원
    • YAKHAK HOEJI
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    • v.44 no.1
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    • pp.41-46
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    • 2000
  • Phytochemical examination of the leaves of Alnus maximowiczii Call, one of the indigenous Alnus species grows in Korea, has led to the isolation of three flavonoids. Structure of these flavonoids were elucidated as quercetin-3-O-$\beta$-D-glucopyranoside (1) , quercetin-3-O-$\alpha$-L-rhamnopyranoside (2) and myricetin-3-O-$\alpha$-L-rhamnopyranoside (3) respectively by means of physico-chemical and spectral evidences.

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Optimal Conditions and Substrate Specificity for Trehalose Production by Resting Cells of Arthrobacter crystallopoietes N-08

  • Seo, Yi-Seul;Shin, Kwang-Soon
    • Preventive Nutrition and Food Science
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    • v.16 no.4
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    • pp.357-363
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    • 2011
  • Recently, we found that Arthrobacter crystallopoietes N-08 isolated from soil directly produces trehalose from maltose by a resting cell reaction. In this study, the optimal set of conditions and substrate specificity for the trehalose production using resting cells was investigated. Optimum temperature and pH of the resting cell reaction were $55^{\circ}C$ and pH 5.5, respectively, and the reaction was stable for two hours at $37{\sim}55^{\circ}C$ and for one hour at the wide pH ranges of 3~9. Various disaccharide substrates with different glycosidic linkages, such as maltose, isomaltose, cellobiose, nigerose, sophorose, and laminaribiose, were converted into trehalose-like spots in thin layer chromatography (TLC). These results indicated broad substrate specificity of this reaction and the possibility that cellobiose could be converted into other trehalose anomers such as ${\alpha},{\beta}$- and ${\beta},{\beta}$-trehalose. Therefore, the product after the resting cell reaction with cellobiose was purified by ${\beta}$-glucosidase treatment and Dowex-1 ($OH^-$) column chromatography and its structure was analyzed. Component sugar and methylation analyses indicated that this cellobiose-conversion product was composed of only non-reducing terminal glucopyranoside. MALDI-TOF and ESI-MS/MS analyses suggested that this oligosaccharide contained a non-reducing disaccharide unit with a 1,1-glucosidic linkage. When this disaccharide was analyzed by $^1H$-NMR and $^{13}C$-NMR, it gave the same signals with ${\alpha}$-D-glucopyranosyl-(1,1)-${\alpha}$-D-glucopyranoside. These results suggest that cellobiose can be converted to ${\alpha},{\alpha}$-trehalose by the resting cells of A. crystallopoietes N-08.

Inhibitory Activity of Aralia elata Leaves on Protein Tyrosine Phosphatase 1B and α-Glucosidase (참두릅 잎의 Protein Tyrosine Phosphatase 1B와 α-Glucosidase 저해 활성)

  • Cho, Yoon Sook;Seong, Su Hui;Bhakta, Himanshu Kumar;Jung, Hee Jin;Moon, Kyung Ho;Choi, Jae Sue
    • Korean Journal of Pharmacognosy
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    • v.47 no.1
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    • pp.29-37
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    • 2016
  • Anti-diabetic potential of the leaves of A. elata through the inhibitory activity on PTP1B and ${\alpha}$-glucosidase has not been reported. In this study, the EtOAc fraction of methanolic extract from the leaves of A. elata showed potent inhibitory activity against the PTP1B and ${\alpha}$-glucosidase with $IC_{50}$ value of $96.29{\pm}0.3$ and $264.71{\pm}14.87{\mu}g/mL$, respectively. Three known triterpenoids, oleanolic acid, oleanolic acid-28-O-${\beta}$-D-glucopyranoside and oleanolic acid-3-O-${\beta}$-D-glucopyranoside were isolated from the most active EtOAc fraction. We determined the chemical structure of these triterpenoids through comparisons of published nuclear magnetic resonance (NMR) spectroscopic data. Furthermore, we screened these triterpenoids for their ability to inhibit PTP1B and ${\alpha}$-glucosidase over a range of concentrations ($12.5-50{\mu}M$). All three terpenoids significantly inhibited PTP1B in a concentration dependent manner and oleanolic acid effectively inhibited ${\alpha}$-glucosidase. In addition, these compounds revealed potent inhibitory activity with negative binding energies toward PTP1B, showing high affinity and tight binding capacity in the molecular docking studies. Therefore, the results of the present study clearly demonstrate that A. elata leaves and its triterpenoid constituents might be beneficial in the prevention or treatment of diabetic disease.

Cloning of $\beta$-Glucosidase Gene from Streptomyces coelicolor A3(2) and Characterization of the Recombinant $\beta$-Glucosidase Expressed in Escherichia coli (Streptomyces coelicolor A3(2)로 부터 $\beta$-Glucosidase 유전자 클로닝 및 재조합 효소의 특성)

  • Kim, Jae-Young;Kim, Bong-Kyu;Yi, Yong-Sub;Kang, Chang-Soo;Ahn, Joong-Hoon;Lim, Yoong-Ho
    • Microbiology and Biotechnology Letters
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    • v.37 no.2
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    • pp.99-104
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    • 2009
  • The $\beta$-glucosidase gene from Streptomyces coelicolor A3(2) was cloned and expressed in Escherichia coli. The ORF consisted of 1377 nucleotides encoding 51 kDa in a predicted molecular weight. Effects of pH indicated that the $\beta$-glucosidase showed similar activity using $\alpha$-pNPG($\rho$-nitrophenyl-$\alpha$-D-glucopyranoside), $\beta$-pNPG($\rho$-nitrophenyl-$\beta$-D-glucopyranoside), and $\beta$-pNPF($\rho$-nitrophenyl-$\beta$-D-fucopyranoside) at range of pH 3 to 10, and high activity using $\beta$-pNPGA ($\rho$-nitrophenyl-$\beta$-D-galactopyranoside) from pH 5 to 10, especially, 3.3 times higher activity at pH 9. Effects of temperature indicated that the $\beta$-glucosidase showed low activity using $\alpha$-pNPG, $\beta$-pNPG, and $\beta$-pNPF from $20^{\circ}C$ to $70^{\circ}C$, and increased activity using $\beta$-pNPGA from $30^{\circ}C$ to $50^{\circ}C$, 1.8 times higher activity at $50^{\circ}C$ than at $30^{\circ}C$. According to activity determination of other substrates, the enzyme was active on daidzin, genistin, and glycitin, inactive on esculin and apigenin-7-glucose. The EDTA and DTT as reducing agents inhibited $\beta$-glucosidase activity, but SDS and mercaptoethanol did not inhibit. Monovalent or divalent metal ions such as $MnSO_4$, $CaCl_2$, KCl, and $MgSO_4$ did not inhibited $\beta$-glucosidase activity. $CuSO_4$ and NaCl showed low inhibition, and $ZnSO_4$ inhibited 3.3 times higher than control.