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PubMed1996

[Changes in cysteine sulfinic acid in rat brain under the experimental elevation of taurine content].

Excitatory sulfur amino acids (SAAs) seem to be important, because derangement of SAA metabolism has been implicated in the pathogenesis of amyotrophic lateral sclerosis (ALS). Since the concentration of excitatory SAAs in the neural tissue is extremely low, their presence or absence has not been conclusive in the literature. I determined cysteine sulfinic acid (CSA), cysteic acid (CA), homocysteine sulfinic acid (HCSA) and homocysteic acid (HCA) in rat brain by high-performance liquid chromatography using a Shimazu HPLC system LC10. Among the 4 excitatory SAAs mentioned above, the peaks of CA, HCSA and HCA did not appear at the chromatographic retention time corresponding to that of the authentic compounds. Only the peak of CSA was identified by matching retention time with the external standard as well as consistent co-elution with the added authentic compound. Thus the existence of CSA was confirmed and its concentration was 9.18 +/- 3.54 pmol/mg wet weight. Although the other 3 excitatory SAAs were not detected in rat brain, their presence in human brain cannot presently be excluded, because the size of the amino acid pool in rat brain is not the same as that in human brain. I examined in rat brain whether the concentration of CSA would possibly change when taurine, the final product of the metabolic pathway of SAAs, is experimentally increased. The inhalation of nitrous oxide (N2O) and the thyroidectomy have both been known to give rise to the elevation of taurine in the central nervous system, the mechanism of which is reportedly due to the impairment of the folate cycle. The metabolic flow of the SAA pathway is increased as a result of slowing down of the folate cycle, the damage of which has been shown in the brain of N2O-inhaled rats and thyroidectomized rats as well as of patients with ALS. The concentration of CSA was significantly increased in the cerebrum and the brainstem of the N2O-inhaled rats and the thyroidectomized rats, and in the cerebellum of the latter. CSA, recently demonstrated as a neurotransmitter, has been reported to have neurotoxicity stronger than that of gultamate in cultured rat cerebral neurons. The measurement of excitatory SAAs, especially CSA in nervous tissue of ALS will be required, although relevance of excitatory SAAs to the pathogenesis of ALS is not certain at present.

Amyotrophic Lateral Sclerosis↗
PubMed1988

The biosynthesis of sulfoquinovosyldiacylglycerol: studies with groundnut (Arachis hypogaea) leaves.

The biosynthetic pathway of sulfoquinovosyldiacylglycerol (SQDG) was investigated using groundnut (Arachis hypogaea) leaf discs and 35S-labeled precursors. [35S]SO4(2-) was actively taken up by the leaf discs and rapidly incorporated into SQDG. After 2 h, 1.5% of the [35S]SO4(2-) added to the incubation medium was taken up, of which 28% was incorporated into SQDG. The methanol-water phases of the lipid extracts of the leaf discs were analyzed for the 35S-labeled intermediates. Up to 2 h of incubation, cysteic acid, 3-sulfopyruvate, 3-sulfolactate, 3-sulfolactaldehyde, and sulfoquinovose (SQ) which have been proposed as intermediates [Davies et al. (1966) Biochem. J. 98, 369-373] were not labeled. Only a negligible amount of radioactivity was observed in these compounds after incubation for 4 h and more. Addition of sodium molybdate inhibited the uptake of [35S]SO4(2-) as well as its incorporation into SQDG by the leaf discs, suggesting that 3'-phosphoadenosine-5'-phosphosulfate may be involved in the biosynthesis of SQDG. Addition of unlabeled cysteic acid to the incubation medium enhanced the uptake of [35S]SO4(2-) but did not affect its incorporation into SQDG. 35S-labeled cysteic acid was taken up by the leaf discs and metabolized to sulfoacetic acid but not incorporated into SQ or SQDG. These results show that cysteic acid is not an intermediate in SQDG biosynthesis. [35S]SQ was taken up by the leaf discs and incorporated into SQDG in a time-dependent manner. [35S]Sulfoquinovosylglycerol was also taken up by the leaf discs but not incorporated into SQDG. It is concluded that SQDG is not biosynthesized by the proposed sulfoglycolytic pathway in higher plants. Though [35S]SQ was converted to SQDG, the rates are much lower compared to [35S]SO4(2-) incorporation, which suggests that a more direct pathway involving sulfonation of a lipid precursor may exist in higher plants.

Arachis↗
PubMed1986

Renal secretion of amino acids in ophidian reptiles.

Net renal tubular secretion of endogenous beta-amino acids (taurine, beta-alanine, beta-aminoisobutyric acid) and their endogenous analogue (L-cysteic acid) was revealed in the olive sea snake, Aipysurus laevis, and in the garter snake, Thamnophis sirtalis, by renal clearance methods. The net secretory rates ranged from 16 to 795 nmol X kg-1 X h-1, with taurine being secreted at the highest rates. These rates of secretion are comparable to those observed in marine fish, the only other group of vertebrates exhibiting renal tubular secretion of L-amino acids under physiological conditions. However, only some snakes (8-58%) demonstrated net tubular secretion; the others (0-58%) showed net tubular reabsorption of these amino acids. Net tubular secretion was consistently observed whenever the filtered load of the amino acid was low, and net reabsorption was apparent whenever the filtered load was high; the two variables being significantly correlated. An analysis of the net amino acid transport rates, both secretory and reabsorptive, as a function of the filtered load suggests that in snakes the beta-amino acids are reabsorbed and secreted at discrete tubular sites, with the secretory sites located beyond the major reabsorptive sites. Taurine, beta-alanine, and L-cysteic acid appear to share a common transport system in the snake renal tubule cells.

Amino Acids↗
PubMed1985

Regulatory role of cysteine dioxygenase in cerebral biosynthesis of taurine. Analysis using cerebellum from 3-acetylpyridine-treated rat.

The effect of 3-acetylpyridine (3-AP) administration on the biosynthesis of taurine in the rat brain has been studied. Treatment with 3-AP induced a significant decrease in the cerebellar contents of taurine and its metabolic precursors, cysteine sulfinic acid (CSA) and cysteic acid (CA), as well as a selective degeneration of climbing fibers in the molecular layer of the cerebellum. It was found that the activity of cerebral cysteine dioxygenase, the enzyme catalyzing the formation of CSA from cysteine, consisted of two systems with low and high Km values. The 3-AP-induced attenuation of cysteine dioxygenase activity with a low Km value was noted only in the cerebellum, while that with a high Km value was detected not only in the cerebellum but also in other brain areas such as the medulla oblongata, striatum and cerebral cortex. In contrast, no alteration in the activity of cysteine sulfinic acid decarboxylase (CSD) was observed in any brain areas examined following the administration of 3-AP. Furthermore, it was found that essentially no cystamine as well as a very low activity of cysteamine dioxygenase is present in the brain. The present results suggest that taurine in the brain is synthesized from cysteine, mainly by the CSA and CA pathways, and the observed decline of cerebellar taurine in 3-AP-treated rats may be due to an attenuation of the biosynthesis, possibly at the step of cysteine dioxygenase. A possible regulatory role of cysteine dioxygenase with a low Km value in the biosynthesis of cerebral taurine is also suggested.

Animals↗
PubMed1984

The structure of the linkage region of bovine nasal cartilage proteoglycan after beta-elimination and sulfite addition.

A method of peptide "fingerprinting" has been developed allowing the separation of the majority of the tryptic peptides of purified proteoglycan subunit from bovine nasal cartilage. When this preparation was reacted with 0.2 M sodium sulfite at pH 11.5, beta-elimination of the substituted glycosaminoglycans and O-linked oligosaccharides and the quantitative addition of sulfite occurred in the serine and threonine residues of the linkage region. After elimination-addition studies with sodium [35S] sulfite, 6 radiolabelled linkage peptides were isolated by 2-dimensional "fingerprinting." Five of these peptides were derived from a section of the protein core in which each [35S] cysteic acid residue was separated by an average of 6-10 amino acid residues. Apart from [35S] cysteic acid, the predominant amino acids in the attached peptides were glycine and glutamic acid (or glutamine), suggesting that a combination of these amino acids in the nascent protein core may be important for the initiation of glycosaminoglycan chains during proteoglycan biosynthesis.

Animals↗
PubMed1977

Amino acids in the synaptic vesicle fraction from calf brain: content, uptake and metabolism.

A synaptic vesicle fraction was prepared from calf brain cortex, containing 10 identified amino acids and two unidentified ninhydrin-positive compounds, one of which is apparently a peptide. The most plentiful amino acids were taurine (1.8 nmol/g original tissue), glutamic acid (1.8), serine (0.9), aspartic acid (0.8) and GABA (0.8); the others identified were cysteic acid (or cysteinesulphinic acid), glutamine, alanine, glycine and lysine. The unknown peptide occurred in a high concentration (about 16 alanine equivalents/g), and contained mainly aspartic acid and serine. Cysteic acid (or cysteinesulphinic acid) also occurred in relatively high amounts, but its peak contained acid-labile impurities. The influx of [14C]glutamate into the vesicles took place by means of non-saturable migration, while two saturable systems having very similar properties were dominant only at low glutamate concentrations. Influx constants for these quantitatively low uptake systems were Km, 34 and 92 micrometer, and Vmax, 33 and 49 nmol/min/g obtained by v versus v/S plot. Almost the same values were also obtained by a 1/v versus 1/S plot. GAD and GABA-T activities in the vesicles were only 1/200th of those in the synaptosomes.

4-Aminobutyrate Transaminase↗
PubMed1966

The cyst wall of Colpoda steinii. A substance rich in glutamic acid residues.

1. The cyst wall of Colpoda steinii has been isolated and its chemical nature examined. It had a nitrogen content 13.9+/-0.2% (s.d.) and an ash 8.6+/-1.6% (s.d.). After lipid and hot-acid extraction there was a variable residual phosphorus of 0.19-0.64%. The protein nature, indicated by infrared and ultraviolet absorption, was confirmed when 100mug. of hydrolysed wall gave a ninhydrin colour equivalent to that given by 0.88-1.01mumoles of glycine. Hexosamine, hexose, pentose, lipid and dipicolinic acid were absent. 2. Paper chromatography of hydrolysates, besides showing the presence of the usual protein amino acids and three unidentified ninhydrin-reacting spots, indicated the presence of large amounts of glutamic acid. Estimated by chromatography, the amount present was 52.9+/-0.6 (s.d.) g./100g. of ash-free wall; manometric estimation of l-glutamic acid with l-glutamate 1-carboxy-lyase gave 46.5+/-0.9 (s.d.) g./100g. 3. Free carboxyl groups were estimated by titration as 0.159+/-0.011 (s.d.) mole/100g. and those present as amide as 0.154+/-0.004 (s.d.) mole/100g., and the total was compared with the dicarboxylic acid content 0.360+/-0.010 (s.d.) mole/100g. 4. After treatment with 98% formic acid 25-30% of the wall material could be extracted by 0.05m-sodium carbonate solution (extract 1); after treatment of the residue with performic acid a further 62-63% based on the original weight could be extracted by 0.05m-sodium carbonate (extract 2). 5. The average values found for the glutamic acid contents were 21.7g./100g. for extract 1 and 58.0g./100g. for extract 2. The cysteic acid content of whole oxidized wall was about 5.8g./100g. and of extract 2 also about 5.8g./100g. The glutamic acid and cysteic acid contents of the final residue were also investigated. 6. The significance of these extraction experiments in relation to the wall structure is discussed.

Cell Wall↗
PubMed1966

Some observations on the biosynthesis of the plant sulpholipid by Euglena gracilis.

1. dl-Cysteine decreases the uptake of (35)SO(4) (2-) by Euglena gracilis but does not decrease the relative incorporation of the isotope into sulpholipid; cysteic acid, on the other hand, does not affect the uptake of (35)SO(4) (2-) but does dilute out its incorporation into the sulpholipid. 2. Both l-[(35)S]cysteic acid and dl-+meso-[3-(14)C]cysteic acid appear almost exclusively in 6-sulphoquinovose. 3. Molybdate inhibits the incorporation of (35)SO(4) (2-) into sulpholipid but not its uptake into the cells; this suggests that adenosine 3'-phosphate 5'-sulphatophosphate may be concerned with the biosynthesis of sulpholipid, and it was shown to be formed by chloroplast fragments. 4. An outline scheme for sulpholipid biosynthesis based on these observations is discussed.

Chloroplasts↗
PubMed1970

Effects of omega-amino acids and related compounds on staphylococcal infections in mice: a combined prophylactic-therapeutic procedure.

By a short-term combined prophylactic-therapeutic procedure, the following compounds were found to be active against staphylococcal infections in Swiss mice: gamma-aminobutyric acid, gamma-amino-beta-hydroxybutyric acid (GABOB), delta-amino-valeric acid (DAVA), epsilon-aminocaproic acid (EACA), trans-4-aminomethylcyclohexanecarboxylic acid (trans-AMCHA), taurine, and cysteic acid. Many of these compounds had displayed limited or no activity by a previously used prophylactic procedure. Although DAVA and GABOB were the most potent of the straight-chain omega-amino acids, trans-AMCHA displayed the greatest antistaphylococcic activity of the omega-amino acids thus far investigated. Homocarnosine (gamma-aminobutyrl histidine, which also was active by the prophylactic procedure) equalled trans-AMCHA in activity. Taurine was similar in potency to DAVA, and the activity of cysteic acid approximated that of EACA.

Alanine↗
PubMed1983

Effects of excitatory amino acids, and of their agonists and antagonists on the release of neurotransmitters from the chick retina.

Effects of glutamic, aspartic, and cysteic acid, and of kainic acid and N-methyl aspartate on the release of labeled GABA, glycine, and taurine were examined in isolated, perfused chick retina. Glutamic acid (0.5-2 mM), increased the release of 3H-GABA by more than four times and that of 14C-glycine by about two times. The release of GABA decreased 50% and that of glycine 95% in the presence of the antagonist of glutamic acid receptors, glutamate diethyl ester (300 microM). N-methyl aspartate, used as an agonist of aspartic acid receptors, preferentially increased the release of GABA (seven times) over that of glycine (three times). The stimulatory effect of N-methyl aspartate was antagonized by D-alpha-aminoadipate and by Mg. Kainic acid (10 microM) induced the release of glycine but not that of GABA. Cysteic acid failed to modify the release of any of the amino acids examined. The efflux of labeled taurine was practically unaffected by all the compounds utilized. The release of GABA by the excitatory amino acids and agonists was Ca-independent but Na-dependent, whereas the release of glycine was markedly Ca-dependent. The evidence presented here suggests that experimental conditions activating receptors of excitatory amino acids differently affect the release of inhibitory amino acids.

Amino Acids↗
PubMed1985

Protective action of sulfur compounds against aldehyde toxicants of cigarette smoke.

Acetaldehyde, acrolein, and formaldehyde are important toxicants of cigarette smoke. Since acetaldehyde is a toxicant common to both heavy alcohol drinking and heavy cigarette smoking, protection studies were undertaken in rats first against acetaldehyde lethality and later against acrolein and formaldehyde lethality. This paper summarizes findings from previously published studies. With acetaldehyde (LD 90 dose/72 hrs.) protection studies were carried out by pretreatment with a high oral dose (2 mmoles/kg) of L-cysteine and 17 other sulfur compounds. Good protection (80% or more survivors) was obtained with L-cysteine, N-acetylcysteine, thiamin . HCl, sodium metabisulfite, L-cysteic acid, and a combination (CTA) of L-cysteine, thiamin . HCl, and L-ascorbic acid. N-acetylcysteine, L-cysteic acid, and the combination CTA gave 100% protection (i.e. 100% survivors). With acrolein (LD 95 dose/72 hrs.), protection data showed 80% survivors with L-cysteine and 95% with the combination CTA. With formaldehyde (LD 95 dose/72 hrs.), protection resulted in 20% survivors with L-cysteine and 55% with the combination CTA. However, protection against formaldehyde lethality could be increased to 90% survivors by repeated dosing with L-ascorbic acid per se over a two day period prior to administration of formaldehyde. Further animal experimentation is necessary before any extrapolation of these findings for human use can be considered. Due to current interest, the potential value of N-acetylcysteine as a protectant is also discussed.

Acetaldehyde↗
PubMed1985

Stimulation of somatostatin release from median eminence tissue incubated in vitro by taurine and related amino acids.

To determine if the putative amino acid transmitter taurine could affect the release of somatostatin (SRIF) from median eminence fragments, median eminences were incubated in vitro in the presence of various concentrations of taurine and its precursors, hypotaurine, cysteamine, cysteic acid, and L-cysteine sulfinic acid. Taurine was effective in releasing SRIF at doses of 50 microM and higher. Surprisingly, cysteic acid was the most potent stimulant of SRIF release, with a minimal effective dose of 0.1 microM. Cysteamine was effective at a dose of 50 microM, hypotaurine was effective only at 200 microM, and cysteine sulfinic acid was ineffective in stimulating SRIF release at any of the doses tested. To determine if the effect of taurine was mediated by the dopaminergic system, the dopamine receptor blocker pimozide (1 microM) was added to the medium containing either taurine or cysteic acid. Pimozide did not prevent the stimulatory effect of the amino acids. In conclusion, these investigations suggest that taurine and related amino acids may be involved in SRIF release by a nondopaminergic pathway. In view of the high concentrations of taurine in the hypothalamus it must be considered a putative transmitter releasing SRIF.

Amino Acids↗
PubMed1975

Soluble and membrane-bound aspartate-binding activities in Salmonella typhimurium.

The specificities of the soluble and membrane aspartate-binding activities were compared with each other and with the specificity of aspartate chemotaxis and were found to be distinct. The soluble aspartate-binding protein was purified to homogeneity and had a molecular weight of 30,000. The dissociation constant was 10(-6) M for aspartate, and the protein bound glutamate, cysteic acid, and 2-amino-3-phosphonopropionate. Aspartate transport was inhibited by cysteic acid.

Aspartic Acid↗
PubMed2001

Endogenous sulphur-containing amino acids: potent agonists at presynaptic metabotropic glutamate autoreceptors in the rat central nervous system.

We have recently demonstrated that presynaptically located metabotropic glutamate (mGlu) autoreceptors regulate synaptic glutamate release both in vitro and in vivo. We now report a positive modulatory action of the sulphur-containing amino acids (SCAAs), L-cysteic acid (CA) and L-cysteine sulphinic acid (CSA), at presynaptic group I mGlu receptors, specifically of the mGlu5 subtype, acting to enhance synaptic glutamate release from the rat forebrain in vitro. Neuronal glutamate release was monitored using electrically-evoked efflux of preloaded [(3)H]-D-aspartate from rat forebrain hemisections. Both CA (3 - 100 muM) and CSA (1 - 100 microM), in addition to the selective group I mGlu receptor agonist, (S)-3,5-dihydroxyphenylglycine ((S)-DHPG), concentration-dependently enhanced electrically-stimulated efflux of [(3)H]-D-aspartate from the rat forebrain slices. Basal efflux of label remained unchanged. The inhibitory activity of the broad spectrum mGlu receptor antagonist, (+/-)-alpha-methyl-4-carboxyphenylglycine ((+/-)-MCPG; 200 microM), coupled with the inactivity of the selective mGlu1 receptor antagonists, (R,S)-1-aminoindan-1,5-dicarboxylic acid ((R,S)-AIDA; 100 - 500 microM) and the more potent (+)-2-methyl-4-carboxyphenylglycine (LY367385; 10 microM) against these responses, indicates an action of the SCAAs at the mGlu5 receptor subtype. This proposal is supported by the potent inhibition of these responses by the selective, non-competitive mGlu5 receptor antagonist, 2-methyl-6-(phenylethynyl)pyridine (MPEP; 10 microM). The observed enhancement of the responses to high concentrations of CA by the selective mGlu5 receptor desensitization inhibitor, cyclothiazide (CYZ; 10 microM), is also consistent with this concept. Administration of the agonists in the presence of bovine serum albumin (BSA; 5 - 15 mg ml(-1)) markedly attenuated the positive modulatory responses observed, strongly supporting a role for arachidonic acid in the expression of these mGlu5 receptor-mediated responses. The regulatory actions of SCAAs on synaptic glutamate release demonstrated in the present study may provide a physiological function for these putative neurotransmitter amino acids in the mammalian brain. These central actions of the SCAAs may have wide-ranging implications for a range of neurological and neuropsychiatric disease states and their treatment.

Amino Acids, Sulfur↗
PubMed1977

Effect of ultra-high-temperature steam injection processing on sulfur-containing amino acids in milk.

Raw skim milk was processed by a modified No-Bac Unitherm IV System (Cherry-Burrell Corp.) at 143 C for 8 s, vacuum cooled to 71 C, collected, and cooled to 4 C. Raw and ultra-high-temperature processed skim milks were oxidized with performic acid, hydrolyzed with hydrochloric acid, and analyzed for cysteine and cystine (as cysteic acid) and methionine (as methionine sulfone) on a Beckman Automatic Amino Acid Analyzer. A loss of approximately 34% of these amino acids was observed in ultra-high-temperature processed skim milk. Sulfhydryl and disulfide groups determined with Ellman's reagent [5,5'-dithiobis(2-nitrobenzoic acid)] indicated no free sulfhydryls in raw skim milk and .07 mmole per liter in ultra-high-temperature processed skim milk. Loss in total sulfhydryl and disulfide groups was approximately 16% in ultra-high-temperature processed milk. Volatile sulfur compounds were detected by odor in the vapor collected from the vacuum chamber, but they could not be identified. Amino acid analysis of milk deposit collected from the injection section revealed .09 microgram of cysteine and cystine (as cysteic acid) per gram of deposit and no detectable methionine.

Amino Acids, Sulfur↗
PubMed1997

Hair sulfur amino acid analysis.

This overview emphasizes present aspects of sulfur-containing amino acids in hair. A selection of analytical procedures to determine cystine, cysteine, S-sulfocysteine, cystine oxide, cysteic acid, lanthionine and lysinoalanine are presented. The methods relate to intact hair or partial and total hydrolysates and comprise chromatography, titration, colorimetry, polarography and spectroscopy. For the analysis of cysteine, cystine and cystine oxides, polarography and spectroscopy are the methods of choice. Cysteic acid, lanthionine and lysinoalanine are analysed by means of ion-exchange chromatography (Spackman et al., 1958) after total hydrolysis.

Alkalies↗
PubMed1997

Fourier-transform Raman spectroscopic study of human hair.

Fourier-transform Raman microscopic spectra of normal, untreated and bleached hair fibres are presented. Vibrational assignments are made and differences are ascribed to the production of cysteic acid from cysteine. Changes in conformation associated with the disulphide bond in the keratotic component are noted from the v(CSSC) vibrational modes at wave numbers near 500 cm-1. Raman spectra of hair root ends have also been investigated with a diminution in cysteine content being observed. Application of the technique to the biomedical investigation of healthy and diseased hair is proposed.

Adolescent↗
PubMed1986

Cystine catabolism in mycelia of Microsporum gypseum, a dermatophytic fungus.

The fate of 35S label was studied during cystine degradation by mycelia of the dermatophytic fungus Microsporum gypseum. Excess free cystine in the medium was readily taken up and its sulfur moiety excreted as inorganic sulfate and sulfite. At intervals after 3-60 min of incubation with 35S cystine the products of cystine catabolism were extracted from the mycelia by boiling water and separated by thin layer chromatography and electrophoresis. A total of 10 sulfur-containing compounds were identified, and their relative radioactivity was assessed. After 3 min the mycelia contained, in addition to cystine, labeled cysteine and particularly cysteine sulfinic acid which was accompanied by a smaller amount of cysteic acid. Later on, oxidized and reduced glutathione, inorganic sulfate and taurine appeared consecutively. In all extracts, small amounts of labeled S-sulfocysteine were found, not, however, sulfite. The results suggest that the intermediates of cysteine degradation in the fungal mycelia are cysteine, cysteine sulfinate, unstable sulfinylpyruvate, sulfite and sulfate, i.e., that the catabolic pattern is similar to that of higher organisms. The formation and the role of S-sulfocysteine, cysteic acid, and of taurine is not yet completely understood, although certainly autoxidative processes are involved in the formation of the latter two compounds, and sulfitolysis in that of the former compound.

Chromatography, Paper↗