thiotaurine and hypotaurine

The shallow-water hydrothermal vent system of Kueishan Island has been described as one of the world's most acidic and sulfide-rich marine habitats. The only recorded metazoan species living in the direct vicinity of the vents is

Topics: Animals; Bacteria; Brachyura; Hydrothermal Vents; Sulfides; Thiosulfates

The disulfide-containing molecule cystamine and the thiosulfonate thiotaurine are of interest as therapeutics. Both are precursors of taurine, but the chemistry of their metabolism is not clear. The rates at which these molecules are metabolized is also unknown. The chemistry and rate constants have been determined for a process in which cystamine is converted in four reactions to thiotaurine. Cystamine is oxidized by diamine oxidase with a specificity constant comparable to other diamine substrates. The rapid hydrogen peroxide-mediated oxidation of cystaldimine yields reactive glyoxal and thiocysteamine, which quickly performs transsulfuration with hypotaurine. Thiotaurine reacts spontaneously with hydrogen peroxide to form taurine and sulfite, but it is 15-fold less reactive than hypotaurine as an antioxidant. An estimation of biological rates of reaction indicates that cystamine is likely to be oxidized by diamine oxidase in vivo, but its metabolic products will be diverted to molecules other than thiotaurine.

Topics: Amine Oxidase (Copper-Containing); Cystamine; Hydrogen Peroxide; Taurine

AbstractVesicomyid clams, which inhabit deep-sea hydrothermal vents and hydrocarbon seeps, are nutritionally dependent on symbiotic, chemoautotrophic bacteria that produce organic matter by using hydrogen sulfide. Vesicomyid clams absorb hydrogen sulfide from the foot and transport it in their hemolymph to symbionts in the gill. However, mechanisms to cope with hydrogen sulfide toxicity are not fully understood. Previous studies on vent-specific invertebrates, including bathymodiolin mussels, suggest that hypotaurine, a precursor of taurine, mitigates hydrogen sulfide toxicity by binding it to bisulfide ion, so as to synthesize thiotaurine. In this study, we cloned cDNAs from the vesicomyid clam

Topics: Animals; Bivalvia; Hydrogen Sulfide; Taurine

Invertebrates at hydrothermal vents and cold seeps must cope with toxic H(2)S. One proposed protection mechanism involves taurine derivatives: At vents and seeps, many animals have high levels of hypotaurine and thiotaurine (a product of hypotaurine and HS), originally found in animals with thiotrophic endosymbionts. To further test the role of these compounds, we analyzed them in vent polychaetes without endosymbionts: Paralvinella sulfincola, P. palmiformis and P. pandorae (paralvinellids) and Nicomache venticola (maldanid). P. sulfincola were collected from a high temperature (42-68 degrees C) and a warm site (21-35 degrees C). P. palmiformis and pandorae were from cool sites (12-18 degrees C) and N. venticola were from a cold site (4 degrees C). H(2)S concentrations in vent effluent largely correlate with temperature. Some specimens were frozen; other ones were kept alive in laboratory chambers, with and without sulfide. Tissues were analyzed for taurine derivatives and other solutes that serve as organic osmolytes. The major osmolyte of all species was glycine. Thiotaurine contents were significantly different among all species, in the order P. sulfincola hot>P. sulfincola warm>P. pandorae>P. palmiformis>N. venticola. P. sulfincola also had high levels of sarcosine; others species had none. Sarcosine and hypotaurine contents of P. sulfincola's branchiae were higher, while glycine contents were lower, than in main body. In P. palmiformis kept in pressure chambers with sulfide, thiotaurine contents were higher and hypotaurine lower than in those kept without sulfide. These results support the hypothesis that conversion of hypotaurine to thiotaurine detoxifies sulfide in vent animals without endosymbionts.

Topics: Adaptation, Physiological; Animals; Gastropoda; Host-Parasite Interactions; Hydrogen Sulfide; Sulfur-Reducing Bacteria; Symbiosis; Taurine

Hypotaurine (HT) has been proposed to reduce sulfide toxicity in some deep-sea invertebrates by scavenging free radicals produced from sulfide oxidation or by scavenging sulfide via the reaction of HT with sulfide, forming thiotaurine (ThT). We tested whether HT or several antioxidants could reduce the total dissolved sulfide concentration in buffered seawater exposed to H(2)S, and whether HT, ThT or antioxidants could increase the viability of Glycera dibranchiata erythrocytes exposed to H(2)S in vitro. We found that 5 and 50 mmol l(-1) HT reduced the dissolved sulfide in cell-free buffer exposed to H(2)S by up to 80% whereas the antioxidants glutathione ethyl ester (GEE), N-acetylcysteine (NAC), L-ascorbic acid (ASC), Tempol and Trolox had no consistent effect. Exposure of erythrocytes to 0.10%-3.2% H(2)S (producing 0.18-4.8 mmol l(-1) sulfide) decreased the fraction of viable cells, as evidenced by loss of plasma membrane integrity, with virtually no cells remaining viable at 1.0% or more H(2)S. Addition of HT (0.5-50 mmol l(-1)) significantly increased the fraction of viable cells (e.g. from 0.01 to 0.84 at 0.32% H(2)S) whereas ThT (0.5 and 5 mmol l(-1)) decreased cell viability. GEE (0.03-3 mmol l(-1)) and NAC (0.001-1 mmol l(-1)), which contain sulfhydryl groups, increased cell viability during H(2)S exposure but to a lesser extent than HT whereas ASC, Tempol and Trolox, which do not contain sulfhydryl groups, decreased viability or had no effect. These data show that HT can protect cells from sulfide in vitro and suggest that sulfide scavenging, rather than free radical scavenging, is the most important mechanism of protection.

Topics: Animals; Antioxidants; Cell Survival; Erythrocytes; Free Radical Scavengers; Polychaeta; Sulfhydryl Compounds; Sulfides; Taurine

Invertebrates at hydrothermal vents and cold seeps must cope with high levels of toxic H2S. In addition, these and all marine invertebrates must balance internal osmotic pressure with that of the ocean. Cells usually do so with organic osmolytes, primarily free amino acids (e.g., taurine, glycine) and methylamines (e.g., betaine). At vents and seeps, clams, mussels, and vestimentiferans with thiotrophic endosymbionts have high levels of hypotaurine and thiotaurine (a product of hypotaurine and HS-). These serve as osmolytes but their primary function may be to transport and/or detoxify sulfide; indeed, thiotaurine has been proposed to be a marker of thiotrophic symbiosis. To test this, we analyzed Depressigyra globulus snails and Lepetodrilus fucensis limpets from Juan de Fuca Ridge vents (1,530 m). Neither has endosymbionts, though the latter has thiotrophic ectosymbionts. Some specimens were rapidly frozen, while other live ones were kept in laboratory chambers, some with and others without sulfide. Non-vent gastropods from a variety of depths (2-3,000 m) were also collected. Tissues were analyzed for major osmolytes and taurine derivatives. The dominant osmolytes of non-vent snails were betaine in all species, and either taurine in shallow-living species or scyllo-inositol, glycerophosphorylcholine, and other amino acids in deep-sea species. In contrast, the dominant osmolytes were hypotaurine and betaine in D. globulus, and hypotaurine in L. fucensis. Both species had thiotaurine (as well as hypotaurine) at levels much greater than previously reported for vent and seep animals without endosymbionts. The ratio of thio- to thio- plus hypotaurine, a possible indicator of sulfide exposure, decreased in both species when kept in laboratory chambers with low or no sulfide, but stayed at high levels in snails kept with 3-5 mM sulfide. Thus, in some vent animals without endosymbionts, sulfide may be detoxified via conversion of hypotaurine to thiotaurine. The latter may be a marker of high sulfide exposure but not of thiotrophic endosymbionts.

Topics: Adaptation, Physiological; Animals; Betaine; Gastropoda; Glycerylphosphorylcholine; Hot Temperature; Hydrogen Sulfide; Oceans and Seas; Sulfur-Reducing Bacteria; Symbiosis; Taurine

Topics: Bile Acids and Salts; Salts; Sulfur; Taurine

Topics: Cystamine; Taurine

Topics: Bile Acids and Salts; Cystamine; Enzymes; Kidney; Mercaptoethylamines; Salts; Taurine