Ethyl Glucoside Research Articles

NMR metabolomics demonstrates phenotypic plasticity of sea buckthorn (Hippophaë rhamnoides) berries with respect to growth conditions in Finland and Canada.

The berries of sea buckthorn (Hippophaë rhamnoides ssp. rhamnoides) cultivars 'Terhi' and 'Tytti' were studied with respect to their growth location, 60° and 68°N latitude in Finland and 46°N in Canada, using 1H NMR metabolomics. The berries of 'Terhi' were characterised by stronger signals of quinic acid, while 'Tytti' had higher levels of O-ethyl β-d-glucopyranoside. The metabolic profile of the northernmost berries was distinctly different from those grown in southern Finland or Canada. Berries from northern Finland had relatively higher levels of quinic acid, glucose, l-quebrachitol and ascorbic acid. Ethyl glucoside was shown to accumulate by several fold at the late stage of maturation in the south as it correlated with degree days (r=0.63) and global radiation (r=0.59), but not in the north. The variance in the composition of the sea buckthorn berries demonstrates plasticity in the acclimatisation to growth environments.

两种新型三甲基硅乙基葡萄糖苷的合成与表征

本文报道了化学方法高效合成两种新型三甲基硅乙基葡萄糖苷的策略，所合成的化合物结构分别经高分辨质谱、一维和二维核磁共振谱确证。该两种新型葡萄糖苷作为寡糖合成的单糖砌块，可为未来我们构建新的寡糖结构片段提供物质基础和技术参考。 Two novel 2-(trimethylsilyl)ethyl glucosides have been synthesized by a short and efficient route starting from D-Glucose. Their structures were elucidated by applying high-resolution mass spectra, one-dimensional and two-dimensional NMR techniques. These glucosides were prepared and used as intermediate building blocks in the scheme developed for oligosaccharide construction.

Alditols and monosaccharides from sorghum vinegar can attenuate platelet aggregation by inhibiting cyclooxygenase-1 and thromboxane-A2 synthase

Ethnopharmacological relevanceVinegar has been used as both a common seasoning and a traditional Chinese medicine. Sorghum vinegar is an excellent source of physiological substances with multiple health benefits. Aim of this studyTo evaluate the antiplatelet aggregation activity of alditols and monosaccharides extracted from sorghum vinegar and analysis its mechanism. Materials and methodsAlditol and monosaccharide extract (AME) from sorghum vinegar was first evaluated for antiplatelet activity using the turbidimetric method. Blood was collected from healthy volunteer donors. The platelet aggregation was induced by arachidonic acid (AA), collagen, adenosine diphosphate (ADP) and thrombin in vitro. AME was divided into three experimental groups with the concentration were 0.10, 0.25 and 0.50mg/mL. In order to determine the inhibitory activity of AME on COX1, TXS and TXA2 production experiments were conducted using the COX1, TXS and TXB2 EIA kit. Computational docking was used to find the docking pose of monosaccharides and alditols with COX1. ResultsAME showed significant induction of antiplatelet activity by arachidonic acid (AA), collagen, adenosine diphosphate (ADP) and thrombin in a concentration-dependent manner (p<0.05). AME (0.50mg/mL) reduced the AA-induced aggregation rate to 10.35%±0.46%, which was comparable to acetylsalicylic acid (aspirin, ASA) (0.50mg/mL, 6.35%±0.58%), a medical standard. Furthermore, AME strongly inhibited cyclooxygenase-1 (COX1) and thromboxane-A2 synthase (TXS), and subsequently attenuated thromboxane-A2 (TXA2) production. These findings indicated that AME attenuates platelet aggregation through the AA metabolism pathway. Computational docking showed that alditols (L-erythritol, L-arabitol, xylitol and D-sorbitol), monosaccharides (D-glucopyranose, D-fructofuranonse, D-xylopyranose, D-galactopyranose and D-ribose), ethyl glucoside and 3,4-(methylenedioxy) mandelic acid could dock directly into the active site of COX1. ConclusionAlditols and monosaccharides from sorghum vinegar inhibit multiple steps in the platelet aggregation pathway, and may be beneficial for the treatment of cardiovascular diseases.

Heteropolyacid catalyzed conversion of fructose, sucrose, and inulin to 5-ethoxymethylfurfural, a liquid biofuel candidate

The heteropolyacid H3PW12O40 has been used as a catalyst for the production of 5-ethoxymethylfurfural (EMF), a viable liquid biofuel, from fructose, sucrose, and inulin. An EMF yield of 65% can be obtained from fructose within 30min at 130°C in ethanol under microwave heating. The introduction of tetrahydrofuran as a co-solvent improved the yield of EMF to 76%. Longer reaction time, higher reaction temperature and higher catalyst amount lead to the decomposition of EMF to ethyl levulinate. The fructose moieties in sucrose and inulin are converted to EMF selectively. However, glucose moieties cannot be converted to EMF by this heteropolyacid catalyst. Instead ethyl glucoside is formed.

Direct transformation of cellulose into methyl and ethyl glucosides in methanol and ethanol media catalyzed by heteropolyacids

The alcoholysis of cellulose in methanol and ethanol media has been studied in the presence of various kinds of acid catalysts. Keggin-type tungstosilicious and tungstophosphoric acids (H 4SiW 12O 40 and H 3PW 12O 40) were found to be highly efficient for the alcoholysis of cellulose. Methyl and ethyl glucosides (both containing α and β isomers) could be obtained in methanol and ethanol with yields as high as 57% and 63%, respectively. The ratio of α and β isomers was ∼1.4–1.6 in both methyl or ethyl glucosides, suggesting the intermolecular transformations between α and β isomers. Our comparative studies show that the alcoholysis of cellulose in methanol or ethanol proceeds more efficiently than the hydrolysis of cellulose in water medium. Glucose yields of only about 5–10% were obtained in water in the presence of an acid catalyst under similar reaction conditions.

Plasma Kinetics and Urine Profile of Ethyl Glucosides after Oral Administration in the Rat

In this in vivo study, the time course of plasma concentration and the urinary excretion of ethyl alpha-D-glucoside (alpha-EG) and ethyl beta-D-glucoside (beta-EG) were investigated in rats after a single oral dose of 4 mmol/kg body weight. Maximal plasma concentrations of both alpha-EG and beta-EG (EGs) reached approximately 3 mM at 1 h after oral administration and then decreased rapidly. Approximately 80% of EGs administered were excreted into the urine during the first 6 h. Within 24 h, cumulative urinary alpha-EG and beta-EG excretions were estimated to be 87.2+/-7.9% and 85.4+/-5.0%, respectively. Traces of both EGs were detected in plasma and urine 24 h after oral ingestion. The results of this study indicate that almost all of both EGs was rapidly absorbed into the blood stream and easily excreted into the urine after oral administration, and that a small amount of them remained in the rat body 24 h after administration.

Structures, Biogenesis, and Biological Activities of Pyrano[4,3-c]isochromen-4-one Derivatives from the Fungus Phellinus igniarius

Further chemical investigation of the Chinese medicinal fungus Phellinus igniarius has resulted in the isolation and structural elucidation of three pyrano[4,3-c]isochromen-4-one derivatives, phelligridins H (1), I (2), and J (3), together with the known compounds davallialactone (4), scopolin, nebularine, uridine, trehalose, glucitol, and ethyl glucoside. The structures of 1-3 were elucidated by spectroscopic methods. Phelligridins H (1) and I (2) possess unprecedented carbon skeletons, and phelligridin J (3) is an oxidative derivative of the co-occurring phelligridin A. Compounds 1 and 2 inhibited protein tyrosine phosphatase 1B (PTP1B) and rat liver microsomal lipid peroxidation, while compound 3 exhibited cytotoxic activity against several human cancer cell lines.

Global systems biology, personalized medicine and molecular epidemiology

Mol Syst Biol. 2: 52 One of the great challenges for 21st century medicine is to deliver effective therapies that are tailored to the exact biology or biological state of an individual to enable so‐called ‘personalized healthcare solutions’. Ideally, this would involve a system of patient evaluation that would tell clinicians the correct drug, dose or intervention for any individual before the start of therapy. A practical approach to this evaluation is the concept of patient stratification in which individuals are biologically subclassified (classically according to some genetic features) and biofeatures modelled in relation to outcome. In principle, such stratification for personalized therapy can be applied to drug safety and efficacy modelling and to more general healthcare paradigms involving optimized nutrition and lifestyle management. Of course, truly personalized treatments, even if they can be developed and applied widely, will lamentably always be a luxury of the worlds' richest citizens and nations. So in some respects, personalized healthcare might appear to be at the opposite end of the medical spectrum to the subject of epidemiology in which disease risk factors and disease incidence are studied in populations rich and poor alike. Systems biology provides us with a common language for both describing and modelling the integrated action of regulatory networks at many levels of biological organization from the subcellular through cell, tissue and organ right up to the whole organism. The relatively new science of molecular epidemiology concerns the measurement of the fundamental biochemical factors that underlie population disease demography and understanding ‘the health of nations’ and this subject naturally lends it to systems biology approaches. Hence, systems biology is certain to have in future a major role in both the development of personalized medicine and in molecular epidemiological studies. Populations are, of course, made up of individuals and, in …

Ethyl glucoside in human urine following dietary exposure: detection by 1H NMR spectroscopy as a result of metabonomic screening of humans.

Metabonomic screening of human urine samples using 1H NMR spectroscopy has revealed the presence of signals resulting from the excretion of ethyl glucoside. Experiments in volunteers have demonstrated that this ethyl glucoside results from dietary exposure to the compound, which is present in beverages such as rice wine and sake, rather than representing a new route for the metabolism of ethanol by humans. The limited studies undertaken in volunteers indicate that ethyl glucoside has a longer biological half life than ethanol itself. The potential problems associated with using this glucoside metabolite as a marker of ethanol consumption are considered.

Enzymatic synthesis of ethyl glucoside lactate in non-aqueous system

Ethyl glucoside lactate, a novel α-hydroxy acid derivative, was synthesized by transesterification in non-aqueous phase using immobilized lipase as biocatalyst. Parameters such as solvent type, substrate concentration, reaction temperature, and enzyme concentration were investigated to optimize the lipase-catalyzed transesterification. In solvent-free system with butyl lactate as both acyl donor and solvent, a 71% conversion was achieved. In order to investigate the effect of initial water content, the reactions were carried out in the mediums treated with molecular sieves. The results showed that conversion and initial rate decreased with the increase of water content. The conversion and initial rate reached to 95% and 67.4 mM/h, respectively, by carrying out the reaction under reduced pressure, which was employed to eliminate butanol and the initial water.

Ethyl Glucoside as a Multifunctional Initiator for Enzyme-Catalyzed Regioselective Lactone Ring-Opening Polymerization

The one-pot biocatalytic synthesis of novel amphiphilic products consisting of an ethyl glucopyranoside (EGP) headgroup and a hydrophobic chain is described. The porcine pancreatic lipase (PPL) catalyzed ring-opening polymerization of e-caprolactone (e-CL) by the multifunctional initiator EGP was carried out at 70 °C in bulk. Products of variable oligo(e-CL) chain length (Mn = 450, 2200) were formed by variation of the e-CL/EGP ratio. Extension of this approach using Candida antarctica lipase (Novozym-435) and EGP as the initiator for trimethylene carbonate (TMC) ring-opening polymerization also resulted in the formation of an EGP−oligo(TMC) conjugate (Mn = 7200). Structural analysis by 1H, 13C, and COSY (13C-13C) NMR experiments showed that the reaction was highly regiospecific; i.e., the oligo(e-CL)/oligo(TMC) chains formed were attached by an ester/carbonate link exclusively to the primary hydroxyl moiety of EGP.

Glucoside ester synthesis in microemulsions catalyzed by Candida antarctica component B lipase

AbstractThe surfactant, ethyl 6‐O‐decanoyl glucoside, was synthesized in microemulsion systems by lipase catalysis. The microemulsions were based on the two substrates for the reaction, ethyl glucoside and fatty acid, and either the sodium salt of the fatty acid or the glucoside ester was used as surfactant. The lipase used was component B from Candida antarctica. Reduced pressure was employed to eliminate the water of condensation. The reaction yield was good, with conversion of fatty acid and ethyl glucoside reaching 77 and 96%, respectively.

Purification of subunit B of Shiga toxin using a synthetic trisaccharide-based affinity matrix.

The blood group P1 antigenic trisaccharide (3), which is the receptor-binding ligand of Shiga-like toxins, is synthesized in a spacer-equipped form (32) from 2-(trimethylsilyl)ethyl glucoside 5 and the 1-thiogalactoside building blocks 10 and 22 in a stereocontrolled, stepwise fashion. Covalent attachment of 32 to hydrazine group-containing agarose gel by reductive amination provided the P1 trisaccharide-containing affinity sorbent which was used for preparative scale isolation of subunit B of Shiga toxin.