Database : MEDLINE
Search on : D02.886.740.703 [DeCS Category]
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  1 / 183 MEDLINE  
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PMID:29238765
Author:Varade V; Markus T; Vankayala K; Friedman N; Sheves M; Waldeck DH; Naaman R
Address:Department of Chemical and Biological Physics, Weizmann Institute of Science, Rehovot, Israel. ron.naaman@weizmann.ac.il.
Title:Bacteriorhodopsin based non-magnetic spin filters for biomolecular spintronics.
Source:Phys Chem Chem Phys; 20(2):1091-1097, 2018 Jan 03.
ISSN:1463-9084
Country of publication:England
Language:eng
Abstract:We discuss spin injection and spin valves, which are based on organic and biomolecules, that offer the possibility to overcome some of the limitations of solid-state devices, which are based on ferromagnetic metal electrodes. In particular, we discuss spin filtering through bacteriorhodopsin in a solid state biomolecular spin valve that is based on the chirality induced spin selectivity (CISS) effect and shows a magnetoresistance of ∼2% at room temperature. The device is fabricated using a layer of bacteriorhodopsin (treated with n-octyl-thioglucoside detergent: OTG-bR) that is adsorbed on a cysteamine functionalized gold electrode and capped with a magnesium oxide layer as a tunneling barrier, upon which a Ni top electrode film is placed and used as a spin analyzer. The bR based spin valves show an antisymmetric magnetoresistance response when a magnetic field is applied along the direction of the current flow, whereas they display a positive symmetric magnetoresistance curve when a magnetic field is applied perpendicular to the current direction.
Publication type:JOURNAL ARTICLE
Name of substance:0 (Thioglucosides); 53026-44-1 (Bacteriorhodopsins); 7440-57-5 (Gold); 85618-21-9 (n-octyl-beta-D-thioglucopyranoside)


  2 / 183 MEDLINE  
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PMID:28343387
Author:Pagnotta E; Agerbirk N; Olsen CE; Ugolini L; Cinti S; Lazzeri L
Address:Council for Agricultural Research and Economics, Research Centre for Industrial Crops, CREA-CIN , via di Corticella 133, 40128 Bologna, Italy.
Title:Hydroxyl and Methoxyl Derivatives of Benzylglucosinolate in Lepidium densiflorum with Hydrolysis to Isothiocyanates and non-Isothiocyanate Products: Substitution Governs Product Type and Mass Spectral Fragmentation.
Source:J Agric Food Chem; 65(15):3167-3178, 2017 Apr 19.
ISSN:1520-5118
Country of publication:United States
Language:eng
Abstract:A system of benzylic glucosinolates was found and characterized in common pepperweed, Lepidium densiflorum Schrad. The major glucosinolate was the novel 4-hydroxy-3,5-dimethoxybenzylglucosinolate (3,5-dimethoxysinalbin), present at high levels in seeds, leaves, and roots. Medium-level glucosinolates were 3,4-dimethoxybenzylglucosinolate and 3,4,5-trimethoxybenzylglucosinolate. Minor glucosinolates included benzylglucosinolate, 3-hydroxy- and 3-methoxybenzylglucosinolate, 4-hydroxybenzylglucosinolate (sinalbin), the novel 4-hydroxy-3-methoxybenzylglucosinolate (3-methoxysinalbin), and indole-type glucosinolates. A biosynthetic connection is suggested. NMR, UV, and ion trap MS/MS spectral data are reported, showing contrasting MS fragmentation of p-hydroxyls and p-methoxyls. Additional investigations by GC-MS focused on glucosinolate hydrolysis products. Whereas glucosinolates generally yielded isothiocyanates, the dominating 3,5-dimethoxysinalbin with a free p-hydroxyl group produced the corresponding alcohol and syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde). After thermal deactivation of the endogenous myrosinase enzyme, massive accumulation of the corresponding nitrile was detected. This case study points out how non-isothiocyanate glucosinolate hydrolysis products are prevalent in nature and of interest in both plant-pathogen interactions and human health.
Publication type:JOURNAL ARTICLE
Name of substance:0 (Isothiocyanates); 0 (Plant Extracts); 0 (Thiocyanates); 0 (Thioglucosides); 0 (benzylglucosinolic acid); 3129-90-6 (isothiocyanic acid)


  3 / 183 MEDLINE  
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PMID:27622707
Author:Guzmán-Pérez V; Bumke-Vogt C; Schreiner M; Mewis I; Borchert A; Pfeiffer AF
Address:Department of Clinical Nutrition, German Institute of Human Nutrition, Potsdam-Rehbrücke, Nuthetal, Germany.
Title:Benzylglucosinolate Derived Isothiocyanate from Tropaeolum majus Reduces Gluconeogenic Gene and Protein Expression in Human Cells.
Source:PLoS One; 11(9):e0162397, 2016.
ISSN:1932-6203
Country of publication:United States
Language:eng
Abstract:Nasturtium (Tropaeolum majus L.) contains high concentrations of benzylglcosinolate. We found that a hydrolysis product of benzyl glucosinolate-the benzyl isothiocyanate (BITC)-modulates the intracellular localization of the transcription factor Forkhead box O 1 (FOXO1). FoxO transcription factors can antagonize insulin effects and trigger a variety of cellular processes involved in tumor suppression, longevity, development and metabolism. The current study evaluated the ability of BITC-extracted as intact glucosinolate from nasturtium and hydrolyzed with myrosinase-to modulate i) the insulin-signaling pathway, ii) the intracellular localization of FOXO1 and, iii) the expression of proteins involved in gluconeogenesis, antioxidant response and detoxification. Stably transfected human osteosarcoma cells (U-2 OS) with constitutive expression of FOXO1 protein labeled with GFP (green fluorescent protein) were used to evaluate the effect of BITC on FOXO1. Human hepatoma HepG2 cell cultures were selected to evaluate the effect on gluconeogenic, antioxidant and detoxification genes and protein expression. BITC reduced the phosphorylation of protein kinase B (AKT/PKB) and FOXO1; promoted FOXO1 translocation from cytoplasm into the nucleus antagonizing the insulin effect; was able to down-regulate the gene and protein expression of gluconeogenic enzymes; and induced the gene expression of antioxidant and detoxification enzymes. Knockdown analyses with specific siRNAs showed that the expression of gluconeogenic genes was dependent on nuclear factor (erythroid derived)-like2 (NRF2) and independent of FOXO1, AKT and NAD-dependent deacetylase sirtuin-1 (SIRT1). The current study provides evidence that BITC might have a role in type 2 diabetes T2D by reducing hepatic glucose production and increasing antioxidant resistance.
Publication type:JOURNAL ARTICLE
Name of substance:0 (Antioxidants); 0 (FOXO1 protein, human); 0 (Forkhead Box Protein O1); 0 (Hypoglycemic Agents); 0 (Isothiocyanates); 0 (NF-E2-Related Factor 2); 0 (NFE2L2 protein, human); 0 (RNA, Small Interfering); 0 (Recombinant Fusion Proteins); 0 (Thiocyanates); 0 (Thioglucosides); 0 (benzylglucosinolic acid); 871J6YOR8Q (benzyl isothiocyanate); EC 2.7.11.1 (Proto-Oncogene Proteins c-akt); EC 3.1.3.9 (Glucose-6-Phosphatase); EC 3.5.1.- (SIRT1 protein, human); EC 3.5.1.- (Sirtuin 1); EC 4.1.1.49 (PCK2 protein, human); EC 4.1.1.49 (Phosphoenolpyruvate Carboxykinase (ATP)); WYQ7N0BPYC (Acetylcysteine)


  4 / 183 MEDLINE  
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PMID:27058294
Author:Lourenço EC; Ventura MR
Address:Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. Da República, EAN, 2780-157 Oeiras, Portugal.
Title:Improvement of the stereoselectivity of the glycosylation reaction with 2-azido-2-deoxy-1-thioglucoside donors.
Source:Carbohydr Res; 426:33-9, 2016 May 13.
ISSN:1873-426X
Country of publication:Netherlands
Language:eng
Abstract:2-Azido-2-deoxy-1-thioglucoside donors with an electron withdrawing group at position 6 were employed to study the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered small primary alcohols to other sugars and steroids, using NIS/TfOH as promoter. p-Tolyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α/ß-D-glucopyranoside afforded the higher α-selectivity, showing that a stronger electron withdrawing ester at O-6 influenced the anomeric selectivity towards the 1,2-cis glucosides. The anomeric stereoselectivity was highly dependent on the acceptor.
Publication type:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
Name of substance:0 (2-azido-2-deoxy-1-thioglucoside); 0 (Alcohols); 0 (Carbohydrates); 0 (Steroids); 0 (Thioglucosides)


  5 / 183 MEDLINE  
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PMID:26795632
Author:Feng WS; Li CG; Zheng XK; Li LL; Chen WJ; Zhang YL; Cao YG; Gong JH; Kuang HX
Address:a School of Pharmacy , Henan University of Traditional Chinese Medicine , Zhengzhou , P.R. China.
Title:Three new sulphur glycosides from the seeds of Descurainia sophia.
Source:Nat Prod Res; 30(15):1675-81, 2016 Aug.
ISSN:1478-6427
Country of publication:England
Language:eng
Abstract:Three new sulphur glycosides, raphanuside B-D (1-3), together with a known sulphur glycoside, raphanuside (4) were isolated from the decoction of the seeds of Descurainia sophia (L.) Webb ex Prantl, and the compound 4 was reported for the first time from this plant. Their structures were identified by means of UV, IR, 1D, 2D NMR (HSQC, HMBC and NOESY) and HR-ESI-MS spectroscopic data.
Publication type:JOURNAL ARTICLE
Name of substance:0 (Glycosides); 0 (Thioglucosides); 0 (raphanuside); 01Y4A2QXY0 (Pyrogallol)


  6 / 183 MEDLINE  
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PMID:26610401
Author:Platz S; Kühn C; Schiess S; Schreiner M; Kemper M; Pivovarova O; Pfeiffer AF; Rohn S
Address:Hamburg School of Food Science, Institute of Food Chemistry, University of Hamburg, Hamburg, Germany.
Title:Bioavailability and metabolism of benzyl glucosinolate in humans consuming Indian cress (Tropaeolum majus L.).
Source:Mol Nutr Food Res; 60(3):652-60, 2016 Mar.
ISSN:1613-4133
Country of publication:Germany
Language:eng
Abstract:SCOPE: Benzyl isothiocyanate (BITC), which occurs in Brassicales, has demonstrated chemopreventive potency and cancer treatment properties in cell and animal studies. However, fate of BITC in human body is not comprehensively studied. Therefore, the present human intervention study investigates the metabolism of the glucosinolate (GSL) glucotropaeolin and its corresponding BITC metabolites. Analyzing BITC metabolites in plasma and urine should reveal insights about resorption, metabolism, and excretion. METHODS AND RESULTS: Fifteen healthy men were randomly recruited for a cross-over study and consumed 10 g freeze-dried Indian cress as a liquid preparation containing 1000 µmol glucotropaeolin. Blood and urine samples were taken at several time points and investigated by LC-ESI-MS/MS after sample preparation using SPE. Plasma contained high levels of BITC-glutathione (BITC-GSH), BITC-cysteinylglycine (BITC-CysGly), and BITC-N-acetyl-L-cysteine (BITC-NAC) 1-5 h after ingestion, with BITC-CysGly appearing as the main metabolite. Compared to human plasma, the main urinary metabolites were BITC-NAC and BITC-Cys, determined 4-6 h after ingestion. CONCLUSION: This study confirms that consumption of Indian cress increases the concentration of BITC metabolites in human plasma and urine. The outcome of this human intervention study supports clinical research dealing with GSL-containing innovative food products or pharmaceutical preparations.
Publication type:JOURNAL ARTICLE
Name of substance:0 (Isothiocyanates); 0 (Thiocyanates); 0 (Thioglucosides); 0 (benzylglucosinolic acid); 499-26-3 (glucotropeolin)


  7 / 183 MEDLINE  
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PMID:26202908
Author:Bertrand B; Citta A; Franken IL; Picquet M; Folda A; Scalcon V; Rigobello MP; Le Gendre P; Casini A; Bodio E
Address:Institut de Chimie Moléculaire, UMR 6302 CNRS Université de Bourgogne Franche Comté, 9 Avenue A. Savary, 21078, Dijon, France.
Title:Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents.
Source:J Biol Inorg Chem; 20(6):1005-20, 2015 Sep.
ISSN:1432-1327
Country of publication:Germany
Language:eng
Abstract:While N-heterocyclic carbenes (NHC) are ubiquitous ligands in catalysis for organic or industrial syntheses, their potential to form transition metal complexes for medicinal applications has still to be exploited. Within this frame, we synthesized new homo- and heterobimetallic complexes based on the Au(I)-NHC scaffold. The compounds were synthesized via a microwave-assisted method developed in our laboratories using Au(I)-NHC complexes carrying a pentafluorophenol ester moiety and another Au(I) phosphane complex or a bipyridine ligand bearing a pendant amine function. Thus, we developed two different methods to prepare homo- and heterobimetallic complexes (Au(I)/Au(I) or Au(I)/Cu(II), Au(I)/Ru(II), respectively). All the compounds were fully characterized by several spectroscopic techniques including far infrared, and were tested for their antiproliferative effects in a series of human cancer cells. They showed moderate anticancer properties. Their toxic effects were also studied ex vivo using the precision-cut tissue slices (PCTS) technique and initial results concerning their reactivity with the seleno-enzyme thioredoxin reductase were obtained.
Publication type:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
Name of substance:0 (Antineoplastic Agents); 0 (Enzyme Inhibitors); 0 (Organogold Compounds); 0 (Saccharomyces cerevisiae Proteins); 0 (Thioglucosides); 789U1901C5 (Copper); EC 1.8.1.7 (Glutathione Reductase); EC 1.8.1.9 (Thioredoxin Reductase 1); EC 1.8.1.9 (Thioredoxin Reductase 2); EC 1.8.1.9 (Txnrd1 protein, rat); EC 1.8.1.9 (Txnrd2 protein, rat)


  8 / 183 MEDLINE  
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PMID:25600688
Author:Shroff R; Schramm K; Jeschke V; Nemes P; Vertes A; Gershenzon J; Svatos A
Address:Research Group on Mass Spectrometry/Proteomics, Max Planck Institute for Chemical Ecology, D-07745, Jena, Germany.
Title:Quantification of plant surface metabolites by matrix-assisted laser desorption-ionization mass spectrometry imaging: glucosinolates on Arabidopsis thaliana leaves.
Source:Plant J; 81(6):961-72, 2015 Mar.
ISSN:1365-313X
Country of publication:England
Language:eng
Abstract:The localization of metabolites on plant surfaces has been problematic because of the limitations of current methodologies. Attempts to localize glucosinolates, the sulfur-rich defense compounds of the order Brassicales, on leaf surfaces have given many contradictory results depending on the method employed. Here we developed a matrix-assisted laser desorption-ionization (MALDI) mass spectrometry protocol to detect surface glucosinolates on Arabidopsis thaliana leaves by applying the MALDI matrix through sublimation. Quantification was accomplished by spotting glucosinolate standards directly on the leaf surface. The A. thaliana leaf surface was found to contain approximately 15 nmol of total glucosinolate per leaf with about 50 pmol mm(-2) on abaxial (bottom) surfaces and 15-30 times less on adaxial (top) surfaces. Of the major compounds detected, 4-methylsulfinylbutylglucosinolate, indol-3-ylmethylglucosinolate, and 8-methylsulfinyloctylglucosinolate were also major components of the leaf interior, but the second most abundant glucosinolate on the surface, 4-methylthiobutylglucosinolate, was only a trace component of the interior. Distribution on the surface was relatively uniform in contrast to the interior, where glucosinolates were distributed more abundantly in the midrib and periphery than the rest of the leaf. These results were confirmed by two other mass spectrometry-based techniques, laser ablation electrospray ionization and liquid extraction surface analysis. The concentrations of glucosinolates on A. thaliana leaf surfaces were found to be sufficient to attract the specialist feeding lepidopterans Plutella xylostella and Pieris rapae for oviposition. The methods employed here should be easily applied to other plant species and metabolites.
Publication type:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T; RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
Name of substance:0 (4-methylthiobutylglucosinolate); 0 (Butyrates); 0 (Glucosinolates); 0 (Thioglucosides)


  9 / 183 MEDLINE  
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PMID:25098670
Author:Wang H; Zhu X
Address:College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China.
Title:Expedient synthesis of an α-S-(1→6)-linked pentaglucosyl thiol.
Source:Org Biomol Chem; 12(36):7119-26, 2014 Sep 28.
ISSN:1477-0539
Country of publication:England
Language:eng
Abstract:An α-S-(1→6)-linked pentaglucosyl thiol has been synthesized in a convenient and stereoselective way. Key steps of the synthesis involved thioglycosylation of 6-iodinated sugars with α-glycosyl thiols under phase transfer conditions. The α-configuration of glycosidic linkages was thus introduced prior to the coupling steps, and relied on the intrinsic configurational stability of α-glycosyl thiols. This work also demonstrated the great utility of MMTr as an effective anomeric S-protecting group.
Publication type:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
Name of substance:0 (Oligosaccharides); 0 (Sulfhydryl Compounds); 0 (Thioglucosides)


  10 / 183 MEDLINE  
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PMID:24998843
Author:Intanon S; Reed RL; Stevens JF; Hulting AG; Mallory-Smith CA
Address:Department of Crop and Soil Science, Oregon State University , 109 Crop Science Building, Corvallis, Oregon 97331, United States.
Title:Identification and phytotoxicity of a new glucosinolate breakdown product from Meadowfoam (Limnanthes alba) seed meal.
Source:J Agric Food Chem; 62(30):7423-9, 2014 Jul 30.
ISSN:1520-5118
Country of publication:United States
Language:eng
Abstract:Meadowfoam (Limnanthes alba Hartw. ex Benth.) is an oilseed crop grown in the Willamette Valley of Oregon. Meadowfoam seed meal (MSM), a byproduct after oil extraction, contains 2-4% glucosinolate (glucolimnanthin). Activated MSM, produced by adding freshly ground myrosinase-active meadowfoam seeds to MSM, facilitates myrosinase-mediated formation of glucosinolate-derived degradation products with herbicidal activity. In the activated MSM, glucolimnanthin was converted into 3-methoxybenzyl isothiocyanate ("isothiocyanate") within 24 h and was degraded by day three. 3-Methoxyphenylacetonitrile ("nitrile") persisted for at least 6 days. Methoxyphenylacetic acid (MPAA), a previously unknown metabolite of glucolimnanthin, appeared at day three. Its identity was confirmed by LC-UV and high resolution LC-MS/MS comparisons with a standard of MPAA. Isothiocyanate inhibited lettuce germination 8.5- and 14.4-fold more effectively than MPAA and nitrile, respectively. Activated MSM inhibited lettuce germination by 58% and growth by 72% compared with the control. Results of the study suggest that MSM has potential uses as a pre-emergence bioherbicide.
Publication type:JOURNAL ARTICLE
Name of substance:0 (Glucosinolates); 0 (Herbicides); 0 (Isothiocyanates); 0 (Thiocyanates); 0 (Thioglucosides); 111810-95-8 (glucolimnanthin); 75272-77-4 (3-methoxybenzyl isothiocyanate); EC 3.2.1.- (Glycoside Hydrolases); EC 3.2.1.147 (thioglucosidase)



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