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PubMed2004

Epidemic parenteral exposure to volatile sulfur-containing compounds at a hemodialysis center.

OBJECTIVE: To determine the cause of acute illness on August 30, 2000, among patients at an outpatient dialysis center (center A). DESIGN: We performed a cohort study of all patients receiving dialysis on August 30, 2000; reviewed dialysis procedures; and analyzed dialysis water samples using microbiologic and chemical assays. SETTING: Dialysis center (center A). PATIENTS: A case-patient was defined as a patient who developed chills within 5 hours after starting hemodialysis at center A on August 30, 2000. RESULTS: Sixteen (36%) of 44 patients at center A met the case definition. All case-patients were hospitalized; 2 died. Besides chills, 15 (94%) of the case-patients experienced nausea; 12 (75%), vomiting; and 4 (25%), fever. Illness was more frequent on the second than the first dialysis shift (16 of 20 vs 0 of 24, P < .001); no other risk factors were identified. The center's water treatment system had received inadequate maintenance and disinfection and a sulfurous odor was noted during sampling of the water from the reverse osmosis (RO) unit. The water had elevated bacterial counts. Volatile sulfur-containing compounds (ie, methanethiol, carbon disulfide, dimethyldisulfide, and sulfur dioxide) were detected by gas chromatography and mass spectrometry in 8 of 12 water samples from the RO unit and in 0 of 28 samples from other areas (P < .001). Results of tests for heavy metals and chloramines were within normal limits. CONCLUSIONS: Parenteral exposure to volatile sulfur-containing compounds, produced under anaerobic conditions in the RO unit, could have caused the outbreak. This investigation demonstrates the importance of appropriate disinfection and maintenance of water treatment systems in hemodialysis centers.

Adult↗
PubMed1992

Hydrogen sulfide and methyl mercaptan in periodontal pockets.

A sensitive gas chromatographic method was developed to determine the amounts of volatile sulfur compounds in gingival fluid. Hydrogen sulfide was the predominant volatile sulfur compound and was detected in 61 out of 79 studied periodontal pockets. Methyl mercaptan was found in about 20% of the pockets. No other volatile sulfur compounds were detected. The highest concentration of hydrogen sulfide in gingival fluid was 1.9 mmol/liter, and of methyl mercaptan 0.16 mmol/liter.

Adult↗
PubMed2005

Role of sulfur chirality in the chemical processes of biology.

Chiral structures profoundly influence chemical and biological processes. While chiral carbon biomolecules have received much attention, chirality is also possible in certain sulfur compounds; just as with carbon, there can be differences in the physiological behavior of chiral sulfur compounds. For instance, one drug enantiomer, Nexium (esomeprazole, a chiral sulfoxide), is used for its superior clinical properties as a proton pump inhibitor over the racemic mixture, Prilosec (Losec, omeprazole). This critical review introduces sulfur stereochemistry and nomenclature, and provides a comprehensive approach to chiral sulfur compounds and their enzymatic reactions in general and secondary metabolism. The major structural types of biological interest are sulfonium salts, sulfoxides, and sulfoximines. (103 references).

Biology↗
PubMed2006

Preclinical perspectives on garlic and cancer.

Evidence continues to point to the anticancer properties of fresh garlic extracts, aged garlic, garlic oil, and a number of specific organosulfur compounds generated by processing garlic. These anticarcinogenic and antitumorigenic characteristics appear to arise through both dose- and temporal-related changes in a number of cellular events involved with the cancer process, including those involving drug metabolism, immunocompetence, cell cycle regulation, apoptosis, and angiogenesis. The ability of garlic and related allyl sulfur compounds to block tumors in the colon, lung, breast, and liver suggests general mechanisms that are not tissue specific. Whereas relatively few studies have compared the relative efficacy of water- and lipid-soluble allyl sulfur compounds, those that have when using chemically induced carcinogen models suggest little difference in response, whereas tumor proliferation/apoptosis is highly dependent on the species provided. A shift in sulfhydryl groups, alterations in glutathione:oxidized glutathione ratios, and resultant changes in cellular redox status may be involved in some of the phenotypic changes caused by allyl sulfur compounds. Such changes in thiols by allyl sulfurs may also account for the observed hyperphosphorylation of specific cell cycle proteins and the histone hyperacetylation that has been correlated with suppressed tumor cell proliferation. Whereas the anticarcinogenic and antitumorigenic data to date are impressive, additional studies are needed with more modest exposure to allyl sulfur compounds over prolonged periods. Likewise, additional studies are needed that incorporate transgenic and knockout models to assist in the identification of molecular targets for garlic and its associated allyl sulfur components.

Allyl Compounds↗
PubMedDate not supplied

[Effect of sulfur-containing compounds on the ultrastructural organization of the cell wall of Candida utilis yeasts].

The effect of sulfur-containing compounds (cysteine, homocysteine, glutathione, cystine, and methionine) on the ultrastructural organization of the cell wall was studied in Candida utilis 295t by electron microscopy with the aid of staining SH groups by HgCl2. Treatment of the cells with cysteine and homocysteine was found to modify the ultrastructure of the cell wall: the capsule was damaged and the porosity increased, which facilitated the penetration of these compounds into the periplasm. Their further conversion in the cell has been studied.

Amino Acids, Sulfur↗
PubMedDate not supplied

Degradation of methanethiol in a continuously operated upflow anaerobic sludge-blanket reactor.

The feasibility of anaerobic treatment of wastewater containing volatile organic sulfur compounds was investigated using biomass originating from an anaerobic wastewater treatment facility treating brewery wastewater. Interest focused mainly on the degradation of methanethiol (MT), an extremely volatile and malodorous sulfur compound. Formation of hydrogen sulfide from methanethiol, dimethyl sulfide (DMS), and dimethyl disulfide (DMDS) was observed. Batch experiments showed that methanethiol was predominantly used by methanogenic bacteria as the sole source of energy and carbon. Methane was formed on MT degradation, and in the presence of 2-bromoethanesulfonic acid (BES), a specific inhibitor of methanogens, MT conversion was strongly inhibited. During the MT degradation, DMS and DMDS were the other primary compounds found. Relatively small quantities of DMS were present; whereas the DMDS concentrations could accumulate as a result of the relatively fast rate at which methanethiol autoxidizes in the presence of minor amounts of molecular oxygen. It was shown that DMS and DMDS could be biologically degraded, resulting in the formation of methane and hydrogen sulfide. In a continuous experiment using a laboratory-scale upflow anaerobic sludge-blanket (UASB) reactor with a volume of 2.0 L, the feasibility of anaerobic treatment of methanethiol was tested. The reactor was operated at a hydraulic residence time (HRT) of 6 hours, temperature of 30 degrees C, and pH of 7.3 to 7.6. The maximal MT conversion efficiency in the continuous experiment was reached after approximately 70 days and exceeded 97% at an influent concentration of 6 mM, corresponding to a MT loading rate of 25 mM/d. The specific MT degradation rate, as determined after 40 days of operation in the UASB, measured 1.1 +/- 0.1 mM MT/g volatile suspended solids.d. These results show that anaerobic treatment of MT-containing waste streams is an interesting alternative for currently used physicochemical treatment methods.

Air Pollutants, Occupational↗
PubMed2001

Combining the biological nitrogen and sulfur cycles in anaerobic conditions.

The biochemical processes involved in the anaerobic degradation of carbon, nitrogen and sulfur compounds can be represented by an oxidation-reduction or electron donor-acceptor scheme. The theoretic values of Gibbs free energy (deltaG0) calculated from thermodynamic data indicate the feasibility of the reactions. The interactions C-S and C-N are well known but there is a lack of information about the interaction N-S. The anaerobic transformation of nitrates using reduced sulfur compounds can be explained considering that nitrate acts as electron acceptor while reduced sulfur compounds are the electron donors. A new N-S interaction in anaerobic conditions (ORP = -425 mV) has been experimentally observed when treating industrial wastewater rich in organic nitrogen and sulfate. The mass balances of the different nitrogenous and sulfur compounds in the liquid and gas phases clearly indicated an uncommon evolution. An important percentage of the nitrogen entering the reactor as TKN was removed from the liquid phase appearing as N2 in the gas phase. Simultaneously, only part of the sulfate initially present in the influent appeared as sulfide in the effluent or as hydrogen sulfide in the gas. These experimental observations may suggest a new anaerobic N-S biological interaction involving simultaneous anaerobic ammonium oxidation and sulfate reduction, ammonium being the electron donor and sulfate the electron acceptor.

Bacteria, Anaerobic↗
PubMed2001

Various forms of plasma cysteine and its metabolites in patients undergoing hemodialysis.

The thiol tripeptide glutathione (GSH) is particularly important as an antioxidative protector in the cells. GSH is also a form of storage and transport of cysteine. Under physiological conditions, the kidney plays an essential role in GSH biodegradation to free cysteine via gamma-glutamyl cycle and subsequently in further metabolism of this sulfur amino acid. Our aim was to assess to what degree renal insufficiency affects the level of various cysteine forms and its metabolites (sulfates and sulfane sulfur compounds) in the plasma, and whole blood GSH levels. The concentrations of all the above mentioned sulfur compounds were measured in plasma of patients with end stage renal failure (ESRF) before and after dialysis and in a group of healthy controls. In plasma of patients with ESRF before dialysis tendency towards significant elevation of cystine, protein-bound cysteine and sulfates levels was evident. Simultaneously, a decrease of plasma level of sulfane sulfur compounds, products of anaerobic sulfur metabolism, and whole blood GSH concentration was found. As a consequence, the ratio between the reduced cysteine and the total cysteine concentration was markedly decreased. The dialysis session restore this ratio to the value observed in plasma of control individuals. These findings indicate disturbances in the thiol-disulfide equilibrium and show a higher oxidation status in plasma of patients with ESRF than in healthy controls.

Adult↗
PubMed2006

Reaction mechanisms and kinetics for the oxidations of dimethyl sulfide, dimethyl disulfide, and methyl mercaptan by the nitrate radical.

This study examines the initial oxidation routes of the three major reduced sulfur compounds (CH(3)SH, CH(3)SCH(3), and CH(3)SSCH(3)) by the nitrate radical using density functional and ab initio methods. Stationary points along each reaction pathway are examined using different levels of theory and basis sets to ensure the convergence of the results. Kinetics calculations follow on the determined reaction pathways to obtain the rate constants. This study shows that sulfur compounds exhibit a general trend of hydrogen abstraction following the formation of an initial sulfur-nitrate complex. The results are in agreement with experimental work on CH(3)SCH(3) and CH(3)SH, while refuting a proposal of several previous studies that oxygen addition is the dominant oxidation pathway in the case of CH(3)SSCH(3). The rate constants obtained from kinetics calculations are consistent with experimental findings and exhibit negative temperature dependence. Overall, this study confirms the importance of nitrate in the oxidation of reduced sulfur compounds in the atmosphere.

Disulfides↗
PubMed1999

Inhibitory effect of sulfur-containing compounds in Scorodocarpus borneensis Becc. on the aggregation of rabbit platelets.

The inhibitory effects of three pure compounds isolated from wood garlic, 2,4,5-trithiahexane (I), 2,4,5,7-tetrathiaoctane (II), and 2,4,5,7-tetrathiaoctane 2,2-dioxide (III), on rabbit platelet aggregation induced by collagen, arachidonic acid, U46619, ADP (adenosine 5'-diphosphate), PAF (platelet aggregating factor), and thrombin were studied in vitro. The anti-aggregating activity of 2,4,5,7-tetrathiaoctane 4,4-dioxide (IV) was also measured with collagen and arachidonic acid. I, II, III, and IV inhibited the platelet aggregation induced by all tested agonists. I, II, and III exhibited a stronger inhibitory effect against the thrombin-induced aggregation of GFP (gel-filtered platelets) than against the aggregation induced by the other agonists. Notably, the IC50 value for III was 4 microM, which is approximately 2.5 times stronger than MATS (methyl allyl trisulfide), a major anti-platelet compound isolated from garlic. In inhibiting collagen-induced aggregation, II was as potent as MATS and aspirin, with a marked disaggregation effect on the secondary aggregation by arachidonic acid, at the rate of 47.05%/min at a concentration of 10(-4) M. I, II, and III also suppressed U46619-induced aggregation. These results suggest that sulfur-containing compounds in wood garlic not only inhibit arachidonic acid metabolism but also suppress aggregation in association with the function of the platelet plasma membrane.

15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5↗
PubMed2000

PATHWAYS AND REGULATION OF SULFUR METABOLISM REVEALED THROUGH MOLECULAR AND GENETIC STUDIES.

Sulfur is essential for life. Its oxidation state is in constant flux as it circulates through the global sulfur cycle. Plants play a key role in the cycle since they are primary producers of organic sulfur compounds. They are able to couple photosynthesis to the reduction of sulfate, assimilation into cysteine, and further metabolism into methionine, glutathione, and many other compounds. The activity of the sulfur assimilation pathway responds dynamically to changes in sulfur supply and to environmental conditions that alter the need for reduced sulfur. Molecular genetic analysis has allowed many of the enzymes and regulatory mechanisms involved in the process to be defined. This review focuses on recent advances in the field of plant sulfur metabolism. It also emphasizes areas about which little is known, including transport and recycling/degradation of sulfur compounds.

Journal Article↗
PubMed1998

Physiology and genetics of sulfur-oxidizing bacteria.

Reduced inorganic sulfur compounds are oxidized by members of the domains Archaea and Bacteria. These compounds are used as electron donors for anaerobic phototrophic and aerobic chemotrophic growth, and are mostly oxidized to sulfate. Different enzymes mediate the conversion of various reduced sulfur compounds. Their physiological function in sulfur oxidation is considered (i) mostly from the biochemical characterization of the enzymatic reaction, (ii) rarely from the regulation of their formation, and (iii) only in a few cases from the mutational gene inactivation and characterization of the resulting mutant phenotype. In this review the sulfur-metabolizing reactions of selected phototrophic and of chemotrophic prokaryotes are discussed. These comprise an archaeon, a cyanobacterium, green sulfur bacteria, and selected phototrophic and chemotrophic proteobacteria. The genetic systems are summarized which are presently available for these organisms, and which can be used to study the molecular basis of their dissimilatory sulfur metabolism. Two groups of thiobacteria can be distinguished: those able to grow with tetrathionate and other reduced sulfur compounds, and those unable to do so. This distinction can be made irrespective of their phototrophic or chemotrophic metabolism, neutrophilic or acidophilic nature, and may indicate a mechanism different from that of thiosulfate oxidation. However, the core enzyme for tetrathionate oxidation has not been identified so far. Several phototrophic bacteria utilize hydrogen sulfide, which is considered to be oxidized by flavocytochrome c owing to its in vitro activity. However, the function of flavocytochrome c in vivo may be different, because it is missing in other hydrogen sulfide-oxidizing bacteria, but is present in most thiosulfate-oxidizing bacteria. A possible function of flavocytochrome c is discussed based on biophysical studies, and the identification of a flavocytochrome in the operon encoding enzymes involved in thiosulfate oxidation of Paracoccus denitrificans. Adenosine-5'-phosphosulfate reductase thought to function in the 'reverse' direction in different phototrophic and chemotrophic sulfur-oxidizing bacteria was analysed in Chromatium vinosum. Inactivation of the corresponding gene does not affect the sulfite-oxidizing ability of the mutant. This result questions the concept of its 'reverse' function, generally accepted for over three decades.

Aerobiosis↗
PubMed2001

Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies.

The medicinal use of garlic dates back thousands of years, but there was little scientific support of its therapeutic and pharmacologic properties until recently. In the past decade, the cancer-protective effects of garlic have been well established by epidemiologic studies and animal experiments. However, the cardiovascular-protective properties of garlic are less well understood. In particular, despite the reported hypocholesterolemic effect of garlic, the mechanism of the effect is unclear. In a recent randomized, double-blind, placebo-controlled intervention study, we showed that aged garlic extract (AGE) supplementation was effective in lowering plasma concentration of total cholesterol by 7% and LDL cholesterol by 10% in hypercholesterolemic men compared with subjects consuming a placebo. Supplementation of AGE in animal diets similarly reduced plasma concentrations of total cholesterol and triacylglycerol by 15 and 30%, respectively. In subsequent experiments using cultured rat hepatocytes, we found 44--87% inhibition of cholesterol synthesis by the water-extractable fraction (WEF), methanol-extractable fraction (MEF) and petroleum ether-extractable fraction (PEF) of fresh garlic, and Kyolic (liquid form of AGE). These observations suggested that hydrophilic and hydrophobic compounds of garlic are inhibitory to cholesterol synthesis. Because S-allylcysteine (SAC) alone was less potent than Kyolic, which contains SAC and other sulfur compounds, a maximal inhibition appears to require a concerted action of multiple compounds of garlic. In a series of experiments, we further characterized the inhibitory potency of individual water-soluble and lipid-soluble compounds of garlic. Among water-soluble compounds, SAC, S-ethylcysteine (SEC), and S-propylcysteine (SPC) inhibited cholesterol synthesis by 40--60% compared with 20--35% by gamma-glutamyl-S-allylcysteine (GSAC), gamma-glutamyl-S-methylcysteine (GSMC) and gamma-glutamyl-S-propylcysteine (GSPC). Lipid-soluble sulfur compounds (i.e., diallyl sulfide, diallyl disulfide, diallyl trisulfide, dipropyl sulfide and dipropyl trisulfide) at low concentrations (0.05--0.5 mol/L) slightly (10--15%) inhibited cholesterol synthesis but became highly cytotoxic at high concentrations (1.0--4.0 mol/L). All water-soluble compounds, except S-allylmercaptocysteine, were not cytotoxic, judging from the release of cellular lactate dehydrogenase into the culture medium. Taken together, the results of our studies indicate that the cholesterol-lowering effects of garlic extract, such as AGE, stem in part from inhibition of hepatic cholesterol synthesis by water-soluble sulfur compounds, especially SAC.

Animals↗
PubMed2004

Effects of ursolic acid, betulin and sulfur-containing compounds on mucin release from airway goblet cells.

In this study, we investigated whether ursolic acid, betulin and 2 kinds of sulfur-containing compounds--NAC and MESNA--affect mucin release from airway goblet cells and compared the possible activities of these agents with the inhibitory action on mucin release by PLL and the stimulatory action by ATP. Confluent primary hamster tracheal surface epithelial (HTSE) cells were metabolically radiolabeled using 3H-glucosamine for 24 h and chased for 30 min in the presence of varying concentrations of each agent to assess the effects on 3H-mucin release. The results were as follows: ursolic acid, betulin, MESNA and NAC increased mucin release (40-50 % above control) at the highest concentrations (10(-5) M-10(-3) M). We conclude that ursolic acid and betulin can stimulate mucin release by directly acting on airway mucin-secreting cells and suggest that these agents be further investigated for the possible use as mucoregulators in the treatment of chronic airway diseases.

Acetylcysteine↗
PubMed2006

Selective adsorption of refractory sulfur species on active carbons and carbon based CoMo catalyst.

Adsorption technique could be a reliable alternative in removing to a certain remarkable extent the sulfur species from the feedstock of petroleum oil. The performance of various carbons on adsorption of model sulfur compounds in a simulated feed solution and the sulfur containing compounds in the real gas oil was evaluated. The adsorption experiments have been carried out in a batch scale at ambient temperature and under the atmospheric pressure. In general, the most refractory sulfur compounds in the hydrotreatment reactions were selectively removed and adsorbed. It was found that the adsorbents affinities to dibenzothiophene and 4,6-dimethyldibenzothiophene were much more favored and pronounced than the aromatic matrices like fluorene, 1-methylnaphthalene and 9-methylanthracene. Among the sulfur species, 4,6-dimethyldibenzothiophene was the highest to be removed in terms of both selectivity and capacity over all the present adsorbents. The studied adsorbents showed significant capacities for the polyaromatic thiophenes. The electronic characteristics seem to play a certain role in such behavior. Regeneration of the used adsorbent was successfully attained either by washing it with toluene or by the release of the adsorbates through heat treatment. A suggested adsorptive removal process of sulfur compounds from petroleum distillate over carbon supported CoMo catalyst was discussed.

Journal Article↗