()-2-Carb-oxy-ethyl l-cysteinyl sulfone.

The title compound {systematic name: (2)-2-aza-niumyl-3-[(2-carb-oxy-ethane)-sulfon-yl]propano-ate}, CHNOS, forms enanti-opure crystals in the monoclinic space group 2 and exists as a zwitterion, with a protonated α-amino group and a deprotonated α-carboxyl group. Both the carboxyl groups and the amino group are involved in an extensive multicentered inter-molecular hydrogen-bonding scheme. In the crystal, the diperiodic network of hydrogen bonds propagates parallel to (101) and involves inter-connected heterodromic (10) rings.

1-Amino-1-deoxy-d-fructose ("fructosamine") and its derivatives.

Fructosamine has long been considered as a key intermediate of the Maillard reaction, which to a large extent is responsible for specific aroma, taste, and color formation in thermally processed or dehydrated foods. Since the 1980s, however, as a product of the Amadori rearrangement reaction between glucose and biologically significant amines such as proteins, fructosamine has experienced a boom in biomedical research, mainly due to its relevance to pathologies in diabetes and aging. In this chapter, we assess the scope of the knowledge on and applications of fructosamine-related molecules in chemistry, food, and health sciences, as reflected mostly in publications within the past decade.

1-Amino-1-deoxy-d-fructose ("fructosamine") and its derivatives: An update.

1-Amino-1-deoxy-d-fructose (fructosamine, FN) derivatives are omnipresent in all living organisms, as a result of non-enzymatic condensation and Amadori rearrangement reactions between free glucose and biogenic amines such as amino acids, polypeptides, or aminophospholipids. Over decades, steady interest in fructosamine was largely sustained by its role as a key intermediate structure in the Maillard reaction that is responsible for the organoleptic and nutritional value of thermally processed foods, and for pathophysiological effects of hyperglycemia in diabetes. New trends in fructosamine research include the discovery and engineering of FN-processing enzymes, development of advanced tools for hyperglycemia monitoring, and evaluation of the therapeutic potential of both fructosamines and FN-recognizing proteins.

Microglia Signaling Pathway Reporters Unveiled Manganese Activation of the Interferon/STAT1 Pathway and Its Mitigation by Flavonoids.

Neuroinflammatory responses to neurotoxic manganese (Mn) in CNS have been associated with the Mn-induced Parkinson-like syndromes. However, the framework of molecular mechanisms contributing to manganism is still unclear. Using an in vitro neuroinflammation model based on the insulated signaling pathway reporter transposon constructs stably transfected into a murine BV-2 microglia line, we tested effects of manganese (II) together with a set of 12 metal salts on the transcriptional activities of the NF-κB, activator protein-1 (AP-1), signal transducer and activator of transcription 1 (STAT1), STAT1/STAT2, STAT3, Nrf2, and metal-responsive transcription factor-1 (MTF-1) via luciferase assay, while concatenated destabilized green fluorescent protein expression provided for simultaneous evaluation of cellular viability.

2-Bromo-6-hydrazinyl-pyridine.

The title compound, CHBrN, crystallizes in the ortho-rhom-bic space group 222 with two mol-ecules with different conformations in the asymmetric unit. In the crystal, N-H⋯N and bifurcated N-H⋯(N,N) hydrogen bonds link the mol-ecules into [100] chains; a short Br⋯Br halogen bond and π-π stacking inter-actions are also observed.

β-d-Galacto-pyranosyl-(1→4)-2-amino-2-de-oxy-α-d-gluco-pyran-ose hydro-chloride monohydrate (lactosamine).

The title compound, CHNO ·Cl·HO, (), crystallizes in the monoclinic space group 2 and exists as a monohydrate of a monosubstituted ammonium chloride salt, with the reducing carbohydrate portion existing exclusively as the α-pyran-ose tautomer. The glycosidic bond geometry in () is stabilized by an intra-molecular hydrogen bond and is close to that found in crystalline α-lactose. All heteroatoms except gluco-pyran-ose ring O4 participate in an extensive hydrogen-bonding network, which propagates in all directions in the crystal structure of ().

Structural and Functional Studies of -(2-Carboxyethyl)-L-Cysteine and -(2-Carboxyethyl)-l-Cysteine Sulfoxide.

Insecticidal non-proteinogenic amino acid -(2-carboxyethyl)-L-cysteine (β-CEC) and its assumed metabolite, -(2-carboxyethyl)-l-cysteine sulfoxide (β-CECO), are present abundantly in a number of plants of the legume family. In humans, these amino acids may occur as a result of exposure to environmental acrylonitrile or acrylamide, and due to consumption of the legumes. The β-CEC molecule is a homolog of -carboxymethyl-l-cysteine (carbocisteine, CMC), a clinically employed antioxidant and mucolytic drug.

Mechanochemical generation of N,N-diglycated glycine and MS/MS characterization of its isomeric composition.

The formation of Schiff bases and Amadori rearrangement products (ARP) during the Maillard reaction in solutions is well documented, but their studies in solid-state are limited. Here we report mass-spectrometric characterization of N,N-diglycated Schiff bases and Amadori products obtained during ball milling of amino acids and glucose. Signal intensities of the diglycated adducts in mass-spectra depended on type of the amino acid and the MS ionization mode.

Bidirectional Responses of Eight Neuroinflammation-Related Transcriptional Factors to 64 Flavonoids in Astrocytes with Transposable Insulated Signaling Pathway Reporters.

Neuroinflammation is implicated in a variety of pathologies and is mechanistically linked to hyperactivation of glial cells in the central nervous system (CNS), predominantly in response to external stimuli. Multiple dietary factors were reported to alter neuroinflammation, but their actions on the relevant transcription factors in glia are not sufficiently understood. Here, an in vitro protocol employing cultured astroglial cells, which carry reporters of multiple signaling pathways associated with inflammation, was developed for screening environmental factors and synthetic drugs.

4-(Di-methyl-amino)-benzohydrazide.

The title compound, CHNO, crystallizes in the monoclinic space group 2/ and all non-hydrogen atoms are within 0.1 Å of the mol-ecular mean plane. In the crystal, the hydrogen-bonding pattern results in [001] chains built up from fused (6) and (10) rings; the former consists of N-H⋯N bonds and the latter N-H⋯O bonds.

Structure, Antioxidant and Anti-inflammatory Activities of the (4)- and (4)-epimers of -Carboxymethyl-L-cysteine Sulfoxide.

-Carboxymethyl-L-cysteine (CMC) is an antioxidant and mucolytic commonly prescribed to patients with chronic obstructive pulmonary disease. In humans, CMC is rapidly metabolized to -carboxymethyl-L-cysteine sulfoxide (CMCO). In this study, we assessed structural and functional similarities between CMC and CMCO.

Crystal structure of (,)-2-hy-droxy-4-(methyl-sulfan-yl)butanoic acid.

The title compound, a major animal feed supplement, abbreviated as HMTBA and alternatively called dl-me-thio-nine hy-droxy analogue, CHOS, (), was isolated in pure anhydrous monomeric form. The melting point is 302.5 K and the compound crystallizes in the monoclinic space group 2/, with two conformationally non-equivalent mol-ecules [( ) and ( )] in the asymmetric unit.

Intra-molecular 1,5-S⋯N σ-hole inter-action in ()-'-(pyridin-4-yl-methyl-idene)thio-phene-2-carbohydrazide.

The title compound, CHNOS, (), crystallizes in the monoclinic space group 2/. The mol-ecular conformation is nearly planar and features an intra-molecular chalcogen bond between the thio-phene S and the imine N atoms. Within the crystal, the strongest inter-actions between mol-ecules are the N-H⋯O hydrogen bonds, which organize them into inversion dimers.

Diagnostic MS/MS fragmentation patterns for the discrimination between Schiff bases and their Amadori or Heyns rearrangement products.

Schiff bases, the Amadori and Heyns rearrangement products are the most important isomeric intermediates involved in the early Maillard reaction; distinguishing between them by analytical mass spectroscopic techniques remains a challenge. Here we demonstrate that MS/MS fragmentation patterns can be used for the discrimination between glucose derived Schiff bases, Amadori, and Heyns compounds with glycine. An ESI-qTOF-MS system operated in the positive mode under both acidic and neutral conditions was employed to generate unique MS/MS fragmentation patterns of the molecules.

Bioactive components from garlic on brain resiliency against neuroinflammation and neurodegeneration.

Garlic () has been widely used for culinary and medicinal purposes. Aged garlic extract (AGE) and sulfur-containing compounds, including S-allylcysteine (SAC) are well documented botanical active components of garlic. AGE is prepared by the prolonged extraction of fresh garlic with aqueous ethanol and is considered a nutritional supplement with potential to promote human health.

Dried Fruit Intake and Cancer: A Systematic Review of Observational Studies.

Insufficient intake of total fruits and vegetables is linked to an increased cancer risk, but the relation is not understood for dried fruits. Dried fruits are generally perceived, by both consumers and researchers, as a less attractive but shelf-stable equivalent to fresh fruits and constitute a small but significant proportion of modern diets. Chemical compositions of raw and dried fruits, however, may differ substantially.

Multicentered hydrogen bonding in 1-[(1-de-oxy-β-d-fructo-pyranos-1-yl)aza-nium-yl]cyclo-pentane-carboxyl-ate ('d-fructose-cyclo-leucine').

The title compound, CHNO, (), is conformationally unstable; the predominant form present in its solution is the β-pyran-ose form (74.3%), followed by the β- and α-furan-oses (12.1 and 10.

Crystal structure of the acyclic form of 1-de-oxy-1-[(4-methoxyphenyl)(methyl)amino]-d-fructose.

The title compound, CHNO, (I), crystallizes exclusively in the acyclic form. In solution of (I), the acyclic tautomer represents only 10% of the population in equilibrium, with the other 90% consisting of β-pyran-ose, β-furan-ose, α-pyran-ose, and α-furan-ose cyclic forms. The carbohydrate chain in (I) has a zigzag conformation and the aromatic amine group has a transitional / geometry.

Interaction of Bacterial Phenazines with Colistimethate in Bronchial Epithelial Cells.

Multidrug-resistant bacterial infections are being increasingly treated in clinics with polymyxins, a class of antibiotics associated with adverse effects on the kidney, nervous system, or airways of a significant proportion of human and animal patients. Although many of the resistant pathogens display enhanced virulence, the hazard of cytotoxic interactions between polymyxin antibiotics and bacterial virulence factors (VFs) has not been assessed, to date. We report here the testing of paired combinations of four VF phenazine toxins, pyocyanin (PYO), 1-hydroxyphenazine (1-HP), phenazine-1-carboxylic acid (PCA), and phenazine-1-carboxamide (PCN), and two commonly prescribed polymyxin drugs, colistin-colistimethate sodium (CMS) and polymyxin B, in three human airway cell lines, BEAS-2B, HBE-1, and CFT-1.

Crystal structure and hydrogen bonding in -(1-de-oxy-β-d-fructo-pyranos-1-yl)-2-amino-isobutyric acid.

The title compound, alternatively called d-fructose-2-amino-isobutyric acid (FruAib), CHNO, (I), crystallizes exclusively in the β-pyran-ose form, with two conformationally non-equivalent mol-ecules [(I) and (I)] in the asymmetric unit. In solution, FruAib establishes an equilibrium, with 75.6% of the population consisting of β-pyran-ose, 10.

Development of a Method and Validation for the Quantitation of FruArg in Mice Plasma and Brain Tissue Using UPLC-MS/MS.

Aged garlic extract (AGE) is a popular nutritional supplement and is believed to promote health benefits by exhibiting antioxidant and anti-inflammatory activities and hypolipidemic and antiplatelet effects. We have previously identified -α-(1-deoxy-d-fructos-1-yl)-l-arginine (FruArg) as a major contributor to the bioactivity of AGE in BV-2 microglial cells whereby it exerted a significant ability to attenuate lipopolysaccharide-induced neuroinflammatory responses and to regulate the Nrf2-mediated antioxidant response. Here, we report on a sensitive ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) protocol that was validated for the quantitation of FruArg in mouse plasma and brain tissue samples.

Effects of aged garlic extract and FruArg on gene expression and signaling pathways in lipopolysaccharide-activated microglial cells.

Aged garlic extract (AGE) is widely used as a dietary supplement on account of its protective effects against oxidative stress and inflammation. But less is known about specific molecular targets of AGE and its bioactive components, including N-α-(1-deoxy-D-fructos-1-yl)-L-arginine (FruArg). Our recent study showed that both AGE and FruArg significantly attenuate lipopolysaccharide (LPS)-induced neuroinflammatory responses in BV-2 microglial cells.

Transient Proteotoxicity of Bacterial Virulence Factor Pyocyanin in Renal Tubular Epithelial Cells Induces ER-Related Vacuolation and Can Be Efficiently Modulated by Iron Chelators.

Persistent infections of biofilm forming bacteria, such as Pseudomonas aeruginosa, are common among human populations, due to the bacterial resistance to antibiotics and other adaptation strategies, including release of cytotoxic virulent factors such as pigment pyocyanin (PCN). Urinary tract infections harbor P. aeruginosa strains characterized by the highest PCN-producing capacity, yet no information is available on PCN cytotoxicity mechanism in kidney.

Protective Effects of AGE and Its Components on Neuroinflammation and Neurodegeneration.

Garlic (Allium sativum) is used for culinary and medicinal purposes in diverse cultures worldwide. When fresh garlic is soaked in aqueous ethanol under ambient environment over 4 months or longer, the majority of irritating taste and odor is eliminated and the antioxidant profile in the resulting aged garlic extract (AGE) changes significantly. Recently, AGE and its components have been demonstrated to exert neuroprotective effects in neurodegenerative diseases, including Alzheimer's disease, Parkinson's disease, Huntington's disease, and cerebral ischemia.