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PubMed2000

Analysis of organic sulfur compounds in wine aroma.

Sulfur-containing compounds in wines have been extensively studied because of their effect on wine aroma. The aim of this paper was to give an overview on the analytical methods developed to determine them in wines with special emphasis on gas chromatographic methods, as well as the results obtained. In addition, the problems occurring in application of the common extraction procedures, such as liquid-liquid extraction, static and dynamic headspace and solid-phase microextraction, are presented and discussed.

Sulfur Compounds↗
PubMed1990

Emission of volatile sulfur compounds from spruce trees.

Spruce (Picea Abies L.) trees from the same clone were supplied with different, but low, amounts of plant available sulfate in the soil (9.7-18.1 milligrams per 100 grams of soil). Branches attached to the trees were enclosed in a dynamic gas exchange cuvette and analyzed for the emission of volatile sulfur compounds. Independent of the sulfate supply in the soil, H(2)S was the predominant reduced sulfur compound continuously emitted from the branches with high rates during the day and low rates in the night. In the light, as well as in the dark, the rates of H(2)S emission increased exponentially with increasing water vapor flux from the needles. Approximately 1 nanomole of H(2)S was found to be emitted per mole of water. When stomata were closed completely, only minute emission of H(2)S was observed. Apparently, H(2)S emission from the needles is highly dependent on stromatal aperture, and permeation through the cuticle is negligible. In several experiments, small amounts of dimethylsulfide and carbonylsulfide were also detected in a portion of the samples. However, SO(2) was the only sulfur compound consistently emitted from branches of spruce trees in addition to H(2)S. Emission of SO(2) mainly proceeded via an outburst starting before the beginning of the light period. The total amount of SO(2) emitted from the needles during this outburst was correlated with the plant available sulfate in the soil. The diurnal changes in sulfur metabolism that may result in an outburst of SO(2) are discussed.

Journal Article↗
PubMed2002

Microbial cycling of volatile organic sulfur compounds in anoxic environments.

Microbial cycling of volatile organic sulfur compounds (VOSC) is investigated due to the impact these compounds are thought to have on environmental processes like global temperature control, acid precipitation and the global sulfur cycle. Moreover, in several kinds of industries like composting plants and the paper industry VOSC are released causing odor problems. Waste streams containing these compounds must be treated in order to avoid the release of these compounds to the atmosphere. This paper describes the general mechanisms for the production and degradation of methanethiol (MT) and dimethyl sulfide (DMS), two ubiquitous VOSC in anaerobic environments. Slurry incubations indicated that methylation of sulfide and MT resulting in MT and DMS, respectively, is one of the major mechanisms for VOSC in sulfide-rich anaerobic environments. An anaerobic bacterium that is responsible for the formation of MT and DMS through the anaerobic methylation of H2S and MT was isolated from a freshwater pond after enrichment with syringate as a methyl group donating compound and sole carbon source. In spite of the continuous formation of MT and DMS, steady state concentrations are generally very low. This is due to the microbial degradation of these compounds. Experiments with sulfate-rich and sulfate-amended sediment slurries demonstrated that besides methanogens, sulfate-reducing bacteria can also degrade MT and DMS, provided that sulfate is available. A methanogen was isolated that is able to grow on DMS as the sole carbon source. A large survey of sediments slurries of various origin demonstrated that both isolates are commonly occurring inhabitants of anaerobic environments.

Acid Rain↗
PubMed2006

Antithrombotic and anticancer effects of garlic-derived sulfur compounds: a review.

Garlic (Allium sativum L.) has a long history as being a food having a unique taste and odor along with some medicinal qualities. Modern scientific research has revealed that the wide variety of dietary and medicinal functions of garlic can be attributed to the sulfur compounds present in or generated from garlic. Although garlic produces more than 20 kinds of sulfide compounds from a few sulfur-containing amino acids, their functions are different from one another; e.g., allicin, methyl allyl trisulfide, and diallyl trisulfide have antibacterial, antithrombotic, and anticancer activities, respectively. The present paper reviews the physiological functions of garlic in the limited study fields of its antithrombotic and anticancer effects. Before describing these effects, however, we will discuss briefly some characteristics of garlic as a plant and some modes of absorption of orally-administered sulfur compounds from garlic.

Allyl Compounds↗
PubMed1987

Inhibitory effects of various sulfur compounds on the activity of bovine erythrocyte enzymes.

Studies were conducted to assess the in vitro effects of selected sulfur compounds on the activities of superoxide dismutase (SOD), catalase, glutathione peroxidase (GSHPX), and glucose-6-phosphate dehydrogenase (G6PDH) in hemolyzates of bovine erythrocytes. All sulfur compounds produced concentration-dependent inhibition in the activities of these enzymes, but their effects on each enzyme were different. SOD and catalase activities were most sensitive to sulfide (S2-), followed by sulfite (SO3(2-)) and sulfate (SO4(2-)). GSHPX activity was most sensitive to SO3(2-), followed by S2-, cysteine and SO4(2-). The activity of G6PDH, however, was maximally inhibited by reduced glutathione (GSH), followed by SO3(2-) and SO4(2-); S2- was inhibitory only at high concentrations. Dialysis of the S2- and SO3(2-)-inhibited enzymes resulted in complete or partial reversal of inhibitory effects. The biochemical significance of these effects in relation to erythrocyte physiology is discussed.

Animals↗
PubMed1987

Production and fate of methylated sulfur compounds from methionine and dimethylsulfoniopropionate in anoxic salt marsh sediments.

Anoxic salt marsh sediments were amended with dl-methionine and dimethylsulfoniopropionate (DMSP). Microbial metabolism of methionine yielded methane thiol (MSH) as the major volatile organosulfur product, with the formation of lesser amounts of dimethylsulfide (DMS). Biological transformation of DMSP resulted in the rapid release of DMS and only small amounts of MSH. Experiments with microbial inhibitors indicated that production of MSH from methionine was carried out by procaryotic organisms, probably sulfate-reducing bacteria. Methane-producing bacteria did not metabolize methionine. The involvement of specific groups of organisms in DMSP hydrolysis could not be determined with the inhibitors used, because DMSP was hydrolyzed in all samples except those which were autoclaved. Unamended sediment slurries, prepared from Spartina alterniflora sediments, contained significant (1 to 10 muM) concentrations of DMS. Endogenous methylated sulfur compounds and those produced from added methionine and DMSP were consumed by sediment microbes. Both sulfate-reducing and methane-producing bacteria were involved in DMS and MSH consumption. Methanogenesis was stimulated by the volatile organosulfur compounds released from methionine and DMSP. However, apparent competition for these compounds exists between methanogens and sulfate reducers. At low (1 muM) concentrations of methionine, the terminal S-methyl group was metabolized almost exclusively to CO(2) and only small amounts of CH(4). At higher (>100 muM) concentrations of methionine, the proportion of the methyl-sulfur group converted to CH(4) increased. The results of this study demonstrate that methionine and DMSP are potential precursors of methylated sulfur compounds in anoxic sediments and that the microbial community is capable of metabolizing volatile methylated sulfur compounds.

Journal Article↗
PubMed2001

Sulfur compound production by Geotrichum candidum from L-methionine: importance of the transamination step.

L-methionine degradation products and catabolic enzymatic activities involved in methanethiol generation were investigated in Geotrichum candidum GcG. L-methionine was easily degraded by G. candidum and the transamination product, 4-methylthio-2-oxobutyric acid (KMBA), was found to transiently accumulate. In parallel, considerable L-methionine aminotransferase activity was found in this microorganism. L-methionine and KMBA demethiolating activities were also detected. The degradation of KMBA corresponded to an overall increase in the production of volatile sulfur compounds. These results show that the transamination pathway is of major importance in the initial breakdown of L-methionine by this cheese-ripening microorganism.

Butyrates↗
PubMed2006

Liquid-phase adsorption of multi-ring thiophenic sulfur compounds on carbon materials with different surface properties.

This work examines the effects of structural and surface properties of carbon materials on the adsorption of benzothiophene (BT), dibenzothiophene (DBT), 4-methyldibenzothiophene (4-MDBT) and 4,6-dimethyl-dibenzothiophene (4,6-DMDBT) in the presence of 10 wt % of aromatics in liquid alkanes that simulate sulfur compounds in diesel fuels. The equilibrium-adsorption capacity varies significantly, from 1.7 to 7.0 mg-S/g-A. The results show that different carbon materials have significantly different sulfur-adsorption capacities and selectivities that depend not only on textural structure but also on surface functional groups. The adsorption of multi-ring sulfur compounds on carbon materials was found to obey the Langmuir isotherm. On the basis of adsorption tests and the characterization of carbon materials by BET and XPS, the oxygen-containing functional groups on the surface appear to play an important role in increasing sulfur-adsorption capacity. The adsorption-selectivity trend of the carbon materials for various compounds increases in the order of BT < naphthalene < 2-methylnaphthalene < DBT < 4-MDBT < 4,6-DMDBT, regardless of carbon material types. This selectivity trend for sulfur compounds is dramatically different and almost opposite from that previously observed for adsorption over nickel-based adsorbents. The regeneration of spent activated carbons was also conducted by solvent washing. The high-adsorption capacity and selectivity for methyl DBTs indicate that certain activated carbons are promising adsorbents for selective adsorption for removing sulfur (SARS) as a new approach to ultra deep desulfurization of diesel fuels.

Journal Article↗
PubMed2005

Photochemical oxidation of reduced sulfur compounds in an urban location based on short time monitoring data.

This study examines the oxidation of reduced sulfur compounds (RSCs) in urban ambient air. The photochemical conversions of RSC (such as DMS, CS2, H2S, DMDS, and CH3SH) to a further oxidized form (e.g., SO2, MSA, and H2SO4) were assessed using a photochemical box model. For our model simulation of RSC oxidation, measurements were taken at an urban monitoring station in Seoul, Korea (37.6 degrees N, 127 degrees E) during three separate time periods (e.g., Sept. 17-18, Oct. 23, and Oct. 27-28, 2003). The results indicate that DMS and H2S were the dominant RSCs with concentrations of 370 +/- 140 and 110 +/- 60 pptv, respectively. The photochemical conversion of DMDS to SO2 was found to occur more efficiently than other RSCs. The overall results of our study suggest that photochemical conversion of RSCs accounted for less than 15% of the observed SO2 during the measurement period. The SO2 production from DMS oxidation (mainly by the reaction with OH) was found to be affected primarily by the abstraction channel due to high NOx levels during the experimental conditions.

Air Pollutants↗
PubMed1997

On the transformation of sulfur-containing amino acids and peptides to volatile sulfur compounds (VSC) in the human mouth.

Halitosis is most often caused by oral conditions. Volatile sulfur compounds (VSC), constituting the major components of oral malodor, are produced by anaerobic, gram-negative bacteria retained mainly in periodontal pockets or on the tongue dorsum. Sulfur-containing amino acids serve as substrate for these bacteria. VSC have also been found to have unfavorable effect on the tissue. The aim of this study was to examine whether normal, healthy individuals with no history of halitosis were able to produce VSC from cysteine, when applied as a mouthrinse. A further aim of the study was to investigate and compare the potential of other sulfur-containing amino acids and peptides as substrates for oral VSC production and to localize the odor-production sites. A portable sulfide monitor was used for VSC registration. Results showed that all test subjects produced high oral concentrations of VSC upon rinses with cysteine, which thus seems to be a major substrate for VSC production. The other sulfur-containing substrates had much less effect. It was found that the tongue was the major site for VSC production, and that saliva per se caused low VSC production.

Adult↗
PubMed2006

Allyl sulfur compounds from garlic modulate aberrant crypt formation.

The health benefits of garlic, including inhibition of carcinogenesis, are supported by several epidemiologic and laboratory findings. Garlic's sulfur components have been reported to suppress experimentally induced tumor incidence in several organs, including the colon. Studies in humans also suggest that dietary garlic constituents reduce the risk of colorectal adenomatous polyps, which are considered precursors to colon cancer. Aberrant crypt foci (ACF) are proposed to be early preneoplastic lesions of adenoma-carcinoma in humans and chemically induced colon cancer in rodents. In preclinical studies, both water- and lipid-soluble allyl sulfur compounds arising from processed garlic inhibited ACF. The response to these allyl sulfur compounds appears to depend on several factors, including the speciation, quantity, and duration provided.

Adenoma↗
PubMed2001

Toxic effect of sulfur compounds on anaerobic biogranule.

The effects of sulfide, sulfite and sulfate on degradation of volatile fatty acid (VFA) in UASB process have been studied by using serum bottle assay and septage-leachate acclimated biogranules. The relative toxicity of the compounds towards methane production and degradation of total VFA varied as SO(4)(2-) -S>S(2-)>SO(3)(2-) -S and SO(4)(2-) -S>SO(3)(2-) -S>S(2-), respectively. The difference of this order shows the importance of choosing monitoring factor in evaluating the effect of sulfur compounds on a UASB system. For the individual VFA the effects of sulfur compounds depended on the types of VFA. The VFA-degrading activity of anaerobic biogranules was decreased by 50% when 34, 26 and 20mg of S(2-), SO(3)(2-) -S and SO(4)(2-) -S were added to each gram of biomass, respectively. A comparison of the toxicity-resistance between two different anaerobic biogranules that acclimatized with septage-leachate mixture and septage was also made. In the presence of the leachate, the toxicity-resistance of biogranules was not weakened to sulfide and sulfate but was enhanced to sulfite.

Bacteria, Anaerobic↗
PubMed2002

Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds.

The effects of garlic and selected organosulfur compounds (diallyl disulfide, dipropyl disulfide, diallyl sulfide, allyl methyl sulfide, allyl mercaptan, cysteine, and cystine) on the formation of heterocyclic aromatic amines (HAAs) in fried ground beef patties were evaluated. Minced garlic cloves (ca. 4.8 to 16.7%, wt/wt) or organosulfur compounds (0.67 mmol) were added directly to ground beef. Patties (100 g) were fried at 225 degrees C (surface temperature) for 10 min per side. Two patties were fried for each replication, and five replicates were analyzed for each treatment. For each replicate, four subsamples were analyzed (two unspiked subsamples for concentration and two spiked subsamples for the recovery of HAA standards). The volatile sulfur compounds significantly (P < 0.05) reduced concentrations of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by reductions of 46 to 81%, while average reductions of 35, 22, and 71%, were achieved with cystine, cysteine, and whole garlic, respectively. The volatile sulfur compounds reduced concentrations of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline by 34 to 67%, while reductions of 25, 19, and 63% (P < 0.05) were achieved with cystine, cysteine, and whole garlic, respectively. These studies confirm that garlic and some organosulfur compounds have the potential to reduce HAA formation incooked beef patties.

Amines↗
PubMed2006

Short-term distributions of reduced sulfur compounds in the ambient air surrounding a large landfill facility.

In order to explore the environmental behavior of reduced sulfur compounds (RSC) as malodorous components emitted from diverse source processes, the distribution characteristics of four sulfur (S) compounds - hydrogen sulfide (H2S), methyl mercaptan (CH3SH), dimethyl sulfide (DMS: (CH3)2S), and dimethyl disulfide (DMDS: (CH3)2S2) - were investigated in a municipal landfill area. In the course of this study, their ambient concentration levels were measured during two time periods from 13 individual spots selected as a function of distance from the center of the landfill site. The results generally indicated the absolute dominance of H2S over the other S compounds investigated (up to 5 km radius) such that their mean values were found as 1415 (H2S), 148 (DMS), 20.6 (CH3SH), and 14.4 ppt (DMDS). When our data were compared in terms of either varying distance from the source or relationship with meteorological conditions, the H2S data sets were most evident to reflect the potential effects of strong source processes in the landfill environment, relative to other S gases (or to volatile organic compounds measured concurrently). The results of this study further indicated the relatively good correspondence between the measured H2S concentration level and humans' intuitive sensory of odor and nuisance.

Air Pollutants↗
PubMed2006

Effect of sulfur compounds on biological reduction of nitric oxide in aqueous Fe(II)EDTA2- solutions.

Biological reduction of nitric oxide (NO) in aqueous solutions of EDTA chelated Fe(II) is one of the main steps in the BioDeNOx process, a novel bioprocess for the removal of nitrogen oxides (NOx) from polluted gas streams. Since NOx contaminated gases usually also contain sulfurous pollutants, the possible interferences of these sulfur compounds with the BioDeNOx process need to be identified. Therefore, the effect of the sulfur compounds Na2SO4, Na2SO3, and H2S on the biological NO reduction in aqueous solutions of Fe(II)EDTA2- (25 mM, pH 7.2, 55 degrees C) was studied in batch experiments. Sulfate and sulfite were found to not affect the reduction rate of Fe(II)EDTA2- complexed NO under the conditions tested. Sulfide, either dosed externally or formed during the batch incubation out of endogenous sulfur sources or the supplied sulfate or sulfite, influences the production and consumption of the intermediate nitrous oxide (N2O) during Fe(II)EDTA2- bound NO reduction. At low concentrations (0.2 g VSS/l) of denitrifying sludge, 0.2 mM free sulfide completely inhibited the nitrosyl-complex reduction. At higher biomass concentrations (1.3-2.3 g VSS/l), sulfide (from 15 microM to 0.8 mM) induced an incomplete NO denitrification with N2O accumulation. The reduction rates of NO to N2O were enhanced by anaerobic sludge, presumably because it kept FeEDTA in the reduced state.

Bacteria, Anaerobic↗
PubMed1994

[7-fluoro-4-chromone-3-sulfur compounds].

The novel 7-fluoro-4-chromone-3-sulfur compounds 5-12 were synthesized from the sulfinic acid 4, which can be obtained from the enaminone 3 and thionyl chloride. Especially the Flosequinane-like sulfoxide 12 was prepared and the vasodilating activity was evaluated in isolated ring segments of rat aorta.

Animals↗
PubMed2000

Thermochemical transformation of sulfur compounds in Japanese domestic Allium, Allium victorialis L.

Sulfur compounds contributed to the health promotion in Allium species are produced via enzymic and thermal reactions. Potent antithrombotic agents which have been identified as allyl trisulfides, dithiins, and ajoene in garlic (A. sativum) and caucas (A. victorialis) are thermochemically transformed from allicin (allyl 2-propenethiosulfinate). The leaves and stems of Japanese domestic Allium plant, A. victorialis L. which is widely distributed in the northern part of Japan, under the name "Gyoja-ninniku" is a nutritious vegetable. The significant flavor compounds of caucas are methyl allyl disulfide (Chinese chive odor), diallyl disulfide (garlic-like odor), and dimethyl disulfide and methyl allyl trisulfide (pickles-like odor) among more than 85 peaks on the gas chromatogram. 2-Vinyl-4H-1,3-dithiin and 3,4-dihydro-3-vinyl-1,2-dithiin as platelet aggregation inhibitors were found eliminated in dichloromethane extract of caucas. The significant health promoting factors, allyl trisulfides and dithiins were relatively increased when caucas was cooked on a frying pan.

Allium↗