Intensive agricultural practices impact the health and nutrition of pollinators like honey bees (Apis mellifera). Rapeseed (Brassica napus L.) is widely cultivated, providing diverse nutrients and phytochemicals, including S-methyl-L-cysteine sulfoxide (SMCSO). While the nutritional impact of rapeseed on bees is known, SMCSO's effects remain unexplored. We examined SMCSO and its related metabolites-3-methylthiolactic acid sulfoxide and N-acetyl-S-methyl-L-cysteine sulfoxide-analysing their seasonal fluctuations, colony variations and distribution in body parts. Our findings showed that these compounds in bee gut vary among colonies, possibly due to the dietary preferences, and are highly concentrated in bodies during the summer. They are distributed differently within bee bodies, with higher concentrations in the abdomens of foragers compared with nurses. Administration of SMCSO in a laboratory setting showed no immediate toxic effects but significantly boosted bees' antioxidant capacity. Long-term administration decreased bee body weight, particularly in the thorax and head, and altered amino acid metabolism. SMCSO is found in the nectar and pollen of rapeseed flowers and highly accumulates in rapeseed honey compared with other types of honey. This study reveals the dual impact of SMCSO on bee health, providing a basis for further ecological and physiological research to enhance bee health and colony sustainability.

• Klíčová slova
• Apis mellifera, Brassicaceae, S-methyl-L-cysteine sulfoxide, phytochemical, rapeseed, toxicity,
• MeSH
• antioxidancia farmakologie   MeSH
• Brassica napus metabolismus   MeSH
• Brassicaceae chemie   MeSH
• cystein * analogy a deriváty   metabolismus   MeSH
• fytonutrienty farmakologie   MeSH
• med analýza   MeSH
• opylení MeSH
• pyl chemie   MeSH
• roční období MeSH
• včely účinky léků   fyziologie   MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antioxidancia MeSH
• cystein * MeSH
• fytonutrienty MeSH

Several families of 3,4-dimethylthiolane-based compounds spontaneously formed upon cutting of onion (Allium cepa) were studied. We report the isolation of the first known example of a naturally occurring dithiolactone, 5-hydroxy-3,4-dimethylthiolane-2-thione (cepadithiolactone A, C6H10OS2). Furthermore, on the basis of conceivable spectroscopic evidence (MS, NMR, IR), we could disprove the structure previously proposed for onionin A (C9H16O2S2), which is shown to be in fact (E)-3,4-dimethyl-5-(1-propenylsulfinyl)thiolane-2-ol. The identification of hitherto unknown methyl and propyl homologues of onionin A (dubbed onionins B and C, respectively) is also reported. Furthermore, the existence of the methyl and propyl homologues of cepathiolanes A (C9H16O2S3), trivially named cepathiolanes B and C, respectively, has been newly revealed. The organoleptic properties of these 3,4-dimethylthiolanes and their role in the formation of the pink discoloration of processed onion were also evaluated.

• Klíčová slova
• 3,4-dimethylthiolane, ajothiolane, allithiolane, cepadithiolactone, cepathiolane, discoloration, dithiolactone, garlicnin, isoalliin, onion, onionin, pinking, zwiebelane isomer,
• MeSH
• česneky chemie   MeSH
• cystein analogy a deriváty   chemie   MeSH
• molekulární struktura MeSH
• rostlinné extrakty chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• alliin MeSH Prohlížeč
• cystein MeSH
• rostlinné extrakty MeSH

Hereditary leiomyomatosis and renal cell carcinoma syndrome-associated renal cell carcinomas (RCC) are difficult to diagnose prospectively. We used immunohistochemistry (IHC) to identify fumarate hydratase (FH)-deficient tumors (defined as FH negative, 2-succinocysteine [2SC] positive) in cases diagnosed as "unclassified RCC, high grade or with papillary pattern," or "papillary RCC type 2," from multiple institutions. A total of 124 tumors (from 118 patients) were evaluated by IHC for FH and 2SC. An FH deficiency was found in 24/124 (19%) cases. An indeterminate result (only 1 marker abnormal) was found in 27/124 (22%) cases. In a tissue microarray of 776 RCCs of different types, only 2 (0.5%) tumors, initially considered papillary type 2, were FH deficient. FH mutations were found in 19/21 FH-deficient tumors (with confirmed germline mutations in 9 of 9 tumors in which germline status could be assessed) and in 1/26 FH-indeterminate tumors identified by IHC. No FH mutations were found in 2/21 FH-deficient RCCs, 25/26 FH-indeterminate RCCs, and 10/10 RCCs demonstrating FH expression by IHC. Patients with FH-deficient RCC had a median age of 44 years (range, 21 to 65 y). Average tumor size was 8.2 cm (range, 0.9 to 18 cm). FH-deficient RCCs were characterized by at least focal macronucleoli and demonstrated 2 or more growth patterns in 93% cases. Papillary was the most common (74%) and dominant (59%) pattern, whereas other common patterns included: solid (44%), tubulocystic (41%), cribriform (41%), and cystic (33%). At presentation, 57% were stage ≥pT3, 52% had positive nodes, and 19% had distant metastases. After a mean follow-up of 27 months (range, 1 to 114 mo), 39% of patients were dead of disease, and 26% had disease progression. We conclude that FH and 2SC are useful IHC ancillary tools, which allow recognition of FH-deficient RCC.

• MeSH
• čipová analýza tkání MeSH
• cystein analogy a deriváty   analýza   biosyntéza   MeSH
• dědičné nádorové syndromy diagnóza   genetika   patologie   MeSH
• dospělí MeSH
• fumarasa nedostatek   genetika   MeSH
• imunohistochemie MeSH
• karcinom z renálních buněk diagnóza   etiologie   MeSH
• leiomyomatóza diagnóza   genetika   patologie   MeSH
• lidé středního věku MeSH
• lidé MeSH
• mladý dospělý MeSH
• nádory dělohy diagnóza   genetika   patologie   MeSH
• nádory kůže diagnóza   genetika   patologie   MeSH
• nádory ledvin diagnóza   etiologie   MeSH
• psychomotorické poruchy komplikace   MeSH
• senioři MeSH
• svalová hypotonie komplikace   MeSH
• vrozené poruchy metabolismu komplikace   MeSH
• zárodečné mutace MeSH
• Check Tag
• dospělí MeSH
• lidé středního věku MeSH
• lidé MeSH
• mladý dospělý MeSH
• mužské pohlaví MeSH
• senioři MeSH
• ženské pohlaví MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• cystein MeSH
• fumarasa MeSH
• S-(2-succinyl)cysteine MeSH Prohlížeč

Exhaustive conformational interconversions including transition structure analyses of N-acetyl-l-glycine-N-methylamide as well as its alanine, serine, and cysteine analogues have been investigated at the MP2/6-31G** level, yielding a total of 142 transition states. Improved estimates of relative energies were obtained by separately extrapolating the Hartree-Fock and MP2 energies to the basis set limit and adding the difference between CCSD(T) and MP2 results with the cc-pVDZ basis set to the extrapolated MP2 results. The performance of eight empirical force fields (AMBER94, AMBER14SB, MM2, MM3, MMFFs, CHARMM22_CMAP, OPLS_2005, and AMOEBAPRO13) in reproducing ab initio energies of transition states was tested. Our results indicate that commonly used class I force fields employing a fixed partial charge model for the electrostatic interaction provide mean errors in the ∼10 kJ/mol range for energies of conformational transition states for amino acid conformers. Modern reparametrized versions, such as CHARMM22_CMAP, and polarizable force fields, such as AMOEBAPRO13, have slightly lower mean errors, but maximal errors are still in the 35 kJ/mol range. There are differences between the force fields in their ability for reproducing conformational transitions classified according to backbone/side-chain or regions in the Ramachandran angles, but the data set is likely too small to draw any general conclusions. Errors in conformational interconversion barriers by ∼10 kJ/mol suggest that the commonly used force field may bias certain types of transitions by several orders of magnitude in rate and thus lead to incorrect dynamics in simulations. It is therefore suggested that information for conformational transition states should be included in parametrizations of new force fields.

• MeSH
• alanin analogy a deriváty   MeSH
• aminokyseliny chemie   MeSH
• cystein analogy a deriváty   MeSH
• kvantová teorie MeSH
• molekulární konformace MeSH
• molekulární modely MeSH
• serin analogy a deriváty   MeSH
• termodynamika MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• alanin MeSH
• aminokyseliny MeSH
• cystein MeSH
• serin MeSH

Structures and formation pathways of compounds responsible for pink discoloration of onion and leek were studied. A procedure was developed for the isolation and purification of the color compounds from various model systems and their identification by HPLC-DAD-MS/MS. In total, structures of 15 major color compounds were tentatively determined. It was found that the pigment is a complex mixture of highly conjugated species composed of two N-substituted 3,4-dimethylpyrrole-derived rings linked by either a methine or a propenylidine bridge. These two-ring units are further modified by various C1- and C3-side chains. Experiments with isotope-labeled thiosulfinates revealed that the methine bridge and C1-side chains originate from the methyl group of methiin, whereas the C3 units are derived from the propenyl group of isoalliin.

• Klíčová slova
• Allium, dipyrromethane, discoloration, isoalliin, leek, onion, pinking, plant pigment, pyrrole, thiosulfinate,
• MeSH
• barva MeSH
• biologické pigmenty analýza   chemie   izolace a purifikace   MeSH
• česneky chemie   MeSH
• cystein analogy a deriváty   chemie   MeSH
• kyseliny sulfinové chemie   MeSH
• tandemová hmotnostní spektrometrie MeSH
• vysokoúčinná kapalinová chromatografie MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• alliin MeSH Prohlížeč
• biologické pigmenty MeSH
• cystein MeSH
• kyseliny sulfinové MeSH
• methiin MeSH Prohlížeč
• S-propyl cysteine sulfoxide MeSH Prohlížeč
• thiosulfinic acids MeSH Prohlížeč

Cysteine dioxygenase (CDO, EC 1.13.11.20) catalyses the oxygenation of cysteine to cysteine sulphinic acid leading to the production of sulphite, sulphate and taurine as the final metabolites of cysteine catabolism. Keratinolytic fungi secrete sulphite and sulphate to reduce disulphide bridges in host tissue keratin proteins as the first step of keratinolysis. In the present study, we describe the identification of cDNA, as well as expression and characterisation of recombinant CDO protein from Trichophyton mentagrophytes. The cDNA was amplified using primers designed on the basis of high conservancy CDO regions identified in other fungi. PCR product was cloned and sequenced. Recombinant CDO was expressed in Escherichia coli, and affinity purified and identified by matrix-assisted laser desorption/ionization - time-of-flight mass spectrometry (MALDI-TOF MS). Enzyme activity was assayed by monitoring the production of cysteine sulphinate using mass spectrometry. The Cdo cDNA encodes for a protein consisting of 219 amino acids. Recombinant CDO protein C-terminally fused with a His tag was purified by affinity chromatography. The CDO purified under native condition was proved to be enzymatically active. Protein identity was confirmed by MALDI-TOF MS. Comparison of cDNA sequence with those identified in other fungi revealed significant homology. Identification of T. mentagrophytes CDO provides indispensable tools for future studies of dermatophyte pathogenicity and development of new approaches for prevention and therapy.

• MeSH
• chromatografie afinitní MeSH
• cystein analogy a deriváty   metabolismus   MeSH
• cysteindioxygenasa genetika   izolace a purifikace   MeSH
• DNA fungální chemie   genetika   MeSH
• Escherichia coli genetika   MeSH
• exprese genu MeSH
• klonování DNA MeSH
• komplementární DNA genetika   MeSH
• lidé MeSH
• molekulární sekvence - údaje MeSH
• rekombinantní proteiny genetika   izolace a purifikace   metabolismus   MeSH
• sekvence aminokyselin MeSH
• sekvenční analýza DNA MeSH
• sekvenční homologie aminokyselin MeSH
• spektrometrie hmotnostní - ionizace laserem za účasti matrice MeSH
• Trichophyton enzymologie   genetika   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• cystein MeSH
• cysteindioxygenasa MeSH
• cysteine sulfinic acid MeSH Prohlížeč
• DNA fungální MeSH
• komplementární DNA MeSH
• rekombinantní proteiny MeSH

A novel HPLC method for determination of a wide variety of S-substituted cysteine derivatives in Allium species has been developed and validated. This method allows simultaneous separation and quantification of S-alk(en)ylcysteine S-oxides, gamma-glutamyl-S-alk(en)ylcysteines and gamma-glutamyl-S-alk(en)ylcysteine S-oxides in a single run. The procedure is based on extraction of these amino acids and dipeptides by methanol, their derivatization by dansyl chloride and subsequent separation by reversed phase HPLC. The main advantages of the new method are simplicity, excellent stability of derivatives, high sensitivity, specificity and the ability to simultaneously analyze the whole range of S-substituted cysteine derivatives. This method was critically compared with other chromatographic procedures used for quantification of S-substituted cysteine derivatives, namely with two other HPLC methods (derivatization by o-phthaldialdehyde/tert-butylthiol and fluorenylmethyl chloroformate), and with determination by gas chromatography or capillary electrophoresis. Major advantages and drawbacks of these analytical procedures are discussed. Employing these various chromatographic methods, the content and relative proportions of individual S-substituted cysteine derivatives were determined in four most frequently consumed alliaceous vegetables (garlic, onion, shallot, and leek).

• MeSH
• Allium chemie   MeSH
• cystein analogy a deriváty   analýza   izolace a purifikace   MeSH
• elektroforéza kapilární MeSH
• kořeny rostlin chemie   MeSH
• metody pro přípravu analytických vzorků MeSH
• plamínková ionizace MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
• sloučeniny dansylu MeSH
• vysokoúčinná kapalinová chromatografie MeSH
• Publikační typ
• časopisecké články MeSH
• srovnávací studie MeSH
• Názvy látek
• alliin MeSH Prohlížeč
• cystein MeSH
• dansyl chloride MeSH Prohlížeč
• ethiin MeSH Prohlížeč
• methiin MeSH Prohlížeč
• S-propyl cysteine sulfoxide MeSH Prohlížeč
• sloučeniny dansylu MeSH

A number of cytotoxicity assays are currently available, each of them using specific approach to detect different aspects of cell viability, such as cell integrity, proliferation and metabolic functions. In this study we compared the potential of five commonly employed cytotoxicity assays (WST-1, XTT, MTT, Brilliant blue and Neutral red assay) to detect antiproliferative effects of three selenium compounds, sodium selenite, seleno-L-methionine (SeMet) and Se-(Methyl)selenocysteine (SeMCys) on three colorectal cancer cell lines in vitro. Cells were exposed to the selected selenium compounds in the concentration range of 0-256 microM during 48 h. WST-1 and XTT failed to detect cytotoxic effect, with the exception of the highest concentration of selenium compounds tested. Conversely, the metabolic activity of selenium treated cells measured by WST-1 and XTT significantly increased in comparison to untreated controls. MTT, Neutral red and Brilliant blue assays were more sensitive and yielded mutually comparable results, with significant decrease of measured parameters in a concentration-dependent manner. To a smaller extent, the results were affected by the different chemical nature of the selenium compounds tested as well as by the biological properties of individual cell lines.

• MeSH
• antikarcinogenní látky terapeutické užití   toxicita   MeSH
• cystein analogy a deriváty   terapeutické užití   toxicita   MeSH
• cytotoxiny terapeutické užití   toxicita   MeSH
• lidé MeSH
• methionin analogy a deriváty   terapeutické užití   toxicita   MeSH
• nádorové buněčné linie MeSH
• nádory tračníku farmakoterapie   metabolismus   prevence a kontrola   MeSH
• organoselenové sloučeniny terapeutické užití   toxicita   MeSH
• proliferace buněk účinky léků   MeSH
• seleničitan sodný terapeutické užití   toxicita   MeSH
• selenocystein analogy a deriváty   MeSH
• testy toxicity metody   MeSH
• viabilita buněk účinky léků   MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• srovnávací studie MeSH
• Názvy látek
• antikarcinogenní látky MeSH
• cystein MeSH
• cytotoxiny MeSH
• methionin MeSH
• methionine selenoxide MeSH Prohlížeč
• organoselenové sloučeniny MeSH
• seleničitan sodný MeSH
• selenocystein MeSH
• selenomethylselenocysteine MeSH Prohlížeč

A novel method for determination of S-alk(en)ylcysteine-S-oxides by capillary electrophoresis has been developed and validated. The method is based on extraction of these sulfur amino acids by methanol, their derivatization by fluorenylmethyl chloroformate and subsequent separation by micellar electrokinetic capillary chromatography. Main advantages of the new method are simplicity, sensitivity, high specificity and very low running costs, making it suitable for routine analysis of a large number of samples. Employing this method, the content of S-alk(en)ylcysteine-S-oxides was determined in 12 commonly consumed alliaceous and cruciferous vegetables (e.g. garlic, onion, leek, chive, cabbage, radish, cauliflower and broccoli). The total content of these amino acids in the Allium species evaluated varied between 0.59 and 12.3mg g(-1) fresh weight. Whereas alliin was found only in garlic, isoalliin was the major S-alk(en)ylcysteine-S-oxide in onion, leek, chive and shallot. On the other hand, the cruciferous species analyzed contained only methiin in the range of 0.06-2.45mg g(-1) fresh weight.

• MeSH
• Allium chemie   MeSH
• Brassica chemie   MeSH
• chromatografie micelární elektrokinetická kapilární ekonomika   metody   MeSH
• cystein analogy a deriváty   analýza   MeSH
• methanol chemie   MeSH
• Raphanus chemie   MeSH
• reprodukovatelnost výsledků MeSH
• senzitivita a specificita MeSH
• sulfoxidy analýza   MeSH
• Publikační typ
• časopisecké články MeSH
• hodnotící studie MeSH
• práce podpořená grantem MeSH
• Názvy látek
• cystein MeSH
• methanol MeSH
• sulfoxidy MeSH

OBJECTIVE: The early differential diagnosis of Alzheimer's disease (AD) remains still problematic. We developed a laboratory test enabling us to distinguish patients with AD from those with vascular dementia (VD) and healthy subjects. METHODS: The AD group consisted of 22 women and 18 men. The VD group consisted of 16 women and 8 men. Age-matched controls consisted of 12 women and 9 men. Plasma pregnenolone sulfate (PregS), dehydroepiandrosterone (DHEA) and its sulfate (DHEAS) were determined by radioimmunoassay. 17-Hydroxypregnenolone (17Preg) and 7-hydroxylated metabolites of DHEA (7alphaDHEA, 7betaDHEA) were determined by radioimmunoassay after separation by high performance liquid chromatography (HPLC). Homocysteine (Hcy), cysteine (Cys), cysteinylglycine (Cysgly) and glutathione (GSH) were measured by HPLC. RESULTS: The ANOVA results of significant between-group differences were as follows: The PregS and the 17-Preg and DHEAS levels were independent from the diagnosis. The 7alphaDHEA levels significantly depended on the sex (p < 0.05) and diagnosis (p < 0.01). Amino-thiols were influenced by the diagnosis (p < 0.01, p = 0.0541, p < 0.01 and p = 0.0536 for Cys, Hcy, Cysgly and GSH, respectively). Using a stepwise backward regression analysis, the following parameters were obtained: X = 11.5 + 4.03 x sex +1.09 x Hcy + 0.190 x PregS - 4.76 x DHEAS + 3.00 x DHEA - 34.3 x 77alphaDHEA - 0.885 x Cysgly from which P-value as a discriminator was calculated according to the formula: P = 1/(1 + e(-x)). Then, for P > 0.5, a subject was considered as AD-positive (with 89% correct prediction). DISCUSSION: The opportunity of early differential diagnosis of AD should help physicians to use suitable treatment for retardation of pathological processes.

• MeSH
• 17-alfa-hydroxypregnenolon krev   MeSH
• Alzheimerova nemoc krev   diagnóza   MeSH
• biologické markery krev   MeSH
• cystein analogy a deriváty   krev   MeSH
• dehydroepiandrosteron analogy a deriváty   krev   MeSH
• dehydroepiandrosteronsulfát krev   MeSH
• dipeptidy krev   MeSH
• glutathion krev   MeSH
• homocystein krev   MeSH
• lidé středního věku MeSH
• lidé MeSH
• logistické modely MeSH
• neparametrická statistika MeSH
• prediktivní hodnota testů MeSH
• pregnenolon krev   MeSH
• radioimunoanalýza MeSH
• senioři nad 80 let MeSH
• senioři MeSH
• senzitivita a specificita MeSH
• sexuální faktory MeSH
• sulfhydrylové sloučeniny krev   MeSH
• vaskulární demence krev   diagnóza   MeSH
• vysokoúčinná kapalinová chromatografie MeSH
• Check Tag
• lidé středního věku MeSH
• lidé MeSH
• mužské pohlaví MeSH
• senioři nad 80 let MeSH
• senioři MeSH
• ženské pohlaví MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 17-alfa-hydroxypregnenolon MeSH
• 7-hydroxydehydroepiandrosterone MeSH Prohlížeč
• biologické markery MeSH
• cystein MeSH
• cysteinylglycine MeSH Prohlížeč
• dehydroepiandrosteron MeSH
• dehydroepiandrosteronsulfát MeSH
• dipeptidy MeSH
• glutathion MeSH
• homocystein MeSH
• pregnenolon MeSH
• pregnenolone sulfate MeSH Prohlížeč
• sulfhydrylové sloučeniny MeSH