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American Journal of Physiology.... Nov 2005Electrospray tandem mass spectrometry was used to determine steady-state serum and urinary inorganic sulfate and sulfate ester kinetic profiles of nine normal men after...
Electrospray tandem mass spectrometry was used to determine steady-state serum and urinary inorganic sulfate and sulfate ester kinetic profiles of nine normal men after intravenous injection of the stable isotope sodium [34S]sulfate. Sulfate ester appearance was traced by eliminating inorganic sulfate from samples, followed by hydrolysis of sulfate esters to inorganic sulfate for analysis. Whole body inorganic sulfate turnover in steady state was calculated using standard tracer techniques. Rate of appearance and disappearance of inorganic sulfate was 841 +/- 49 micromol/h. Average urinary inorganic sulfate excretion was 609 +/- 41 micromol/h, and the whole body sulfation rate (total rate of disappearance minus rate of urinary excretion) was 232 +/- 36 micromol/h. Tracer-labeled sulfate esters appeared in serum and urine within 1 h of tracer injection. The kinetics of inorganic sulfate and sulfate esters were linked by means of a compartmental model. The appearance and excretion of sulfate esters accounted for approximately 50% of the total sulfation rate. These results indicate that human whole body sulfation accounts for approximately 27% of inorganic sulfate turnover and that extracellular inorganic sulfate is an important pool for intracellular sulfation. A substantial fraction of newly synthesized sulfate esters promptly enters the extracellular space for excretion in the urine.
Topics: Fasting; Humans; Kinetics; Male; Models, Biological; Spectrometry, Mass, Electrospray Ionization; Sulfates; Sulfur Isotopes; Sulfuric Acid Esters
PubMed: 16051719
DOI: 10.1152/ajpregu.00325.2005 -
Carbohydrate Polymers Jun 2022A pectic polysaccharide (WAP) was isolated from squash and identified as a homogalacturonan with a molecular mass of 83.2 kDa by GPC, monosaccharide composition...
A pectic polysaccharide (WAP) was isolated from squash and identified as a homogalacturonan with a molecular mass of 83.2 kDa by GPC, monosaccharide composition analysis, FT-IR and NMR spectra. Sulfation modification of WAP was carried out and a sulfated derivative (SWAP) was obtained with a substitution degree of 1.81. The NMR spectrum indicated that the sulfation modification mainly occurred at the C-2 and C-3 positions of galacturonan residues. The binding pattern of SWAP to tau K18 protein was observed in 2D HN HSQC spectra of tau, which resembled the tau-heparin interaction, with R2 domain as the major binding region. These results suggest that SWAP has the potential to act as a heparin mimic to inhibit the transcellular spread of tau; thus natural polysaccharide from squash may be developed into therapies for AD and related tauopathies.
Topics: Heparin; Pectins; Spectroscopy, Fourier Transform Infrared; Sulfates
PubMed: 35287864
DOI: 10.1016/j.carbpol.2022.119250 -
Journal of the American Society For... Sep 2006Phosphorylation and sulfation are important modifications affecting the biological properties of carbohydrates, proteins, and glycoproteins. Identification of these two...
Phosphorylation and sulfation are important modifications affecting the biological properties of carbohydrates, proteins, and glycoproteins. Identification of these two functional groups facilitates the understanding of the structure/function relationship in various species. Mass spectrometry is one of the methods used to detect the presence of these two modifications in complex biological mixtures. However, phosphorylated and sulfated structures are isobaric; thus, differentiation between them in routinely used mass spectrometers is problematic. Herein, we demonstrate that these two groups can be discriminated by using ion-pairing in conjunction with MS/MS experiments. The characteristic product ions are used to successfully identify the phosphorylation and sulfation present in mono-, disaccharides, and the highly sulfated glycoprotein, ovine luteinizing hormone. This method is a robust approach to differentiate the two isobaric functional groups.
Topics: Carbohydrates; Glycoproteins; Phosphorylation; Spectrometry, Mass, Electrospray Ionization; Sulfates
PubMed: 16820302
DOI: 10.1016/j.jasms.2006.05.013 -
In Vivo (Athens, Greece) 2008Chondroitin sulfate proteoglycans (CSPGs) such as versican accumulate in tumor stroma and play a key role in tumor growth and invasion. The high expression of CSPGs in... (Review)
Review
Chondroitin sulfate proteoglycans (CSPGs) such as versican accumulate in tumor stroma and play a key role in tumor growth and invasion. The high expression of CSPGs in fast growing tissues and cells is correlated with chondroitin sulfate (CS) chains and the sulfation pattern. The negatively charged CS chains interact with a large number of ligands and receptors and activate signalling pathways which stimulate tumor growth. However, the role of chondroitin sulfate in cancer promotion seems to be controversial, as recent studies support the use of modified CS as a potent anticancer agent. In this review, the biological roles of CSPGs in cancer and the anticancer effects of modified CS are presented and discussed.
Topics: Animals; Antineoplastic Agents; Chondroitin; Humans; Neoplasms; Proteoglycans; Sulfates
PubMed: 18610752
DOI: No ID Found -
Journal of Biochemistry Sep 2012Feed additives such as ractopamine and salbutamol are pharmacologically active compounds, acting primarily as β-adrenergic agonists. This study was designed to...
Feed additives such as ractopamine and salbutamol are pharmacologically active compounds, acting primarily as β-adrenergic agonists. This study was designed to investigate whether the sulfation of ractopamine and salbutamol may occur under the metabolic conditions and to identify the human cytosolic sulfotransferases (SULTs) that are capable of sulfating two major feed additive compounds, ractopamine and salbutamol. A metabolic labelling study showed the generation and release of [(35)S]sulfated ractopamine and salbutamol by HepG2 human hepatoma cells labelled with [(35)S]sulfate in the presence of these two compounds. A systematic analysis using 11 purified human SULTs revealed SULT1A3 as the major SULT responsible for the sulfation of ractopamine and salbutamol. The pH dependence and kinetic parameters were analyzed. Moreover, the inhibitory effects of ractopamine and salbutamol on SULT1A3-mediated dopamine sulfation were investigated. Cytosol or S9 fractions of human lung, liver, kidney and small intestine were examined to verify the presence of ractopamine-/salbutamol-sulfating activity in vivo. Of the four human organs, the small intestine displayed the highest activity towards both compounds. Collectively, these results imply that the sulfation mediated by SULT1A3 may play an important role in the metabolism and detoxification of ractopamine and salbutamol.
Topics: Albuterol; Cytosol; Dopamine; Hep G2 Cells; Humans; Hydrogen-Ion Concentration; Isotope Labeling; Kinetics; Organ Specificity; Phenethylamines; Substrate Specificity; Sulfates; Sulfotransferases; Sulfur; Sulfur Isotopes
PubMed: 22763752
DOI: 10.1093/jb/mvs073 -
Carbohydrate Polymers Jul 2022Lactose-modified chitosan (CTL) is sulfated using SO·py or SO·DMF as sulfating agents. The two products are characterized by elemental analysis, FT-IR, H,C-DEPT-HSQC...
Lactose-modified chitosan (CTL) is sulfated using SO·py or SO·DMF as sulfating agents. The two products are characterized by elemental analysis, FT-IR, H,C-DEPT-HSQC and H,C-HSQC-TOCSY experiments which allow the extent and selectivity of chemical sulfation to be determined. Dynamic Light Scattering shows a pH-dependent association of the sulfated polysaccharides which are described as flexible by the Smidsrød's B parameter and the intrinsic viscosity at infinite ionic strength. Shear viscosity and intrinsic viscosity show that sulfation protocols lead to chain scission which is more pronounced when SO·DMF is used. The sulfated samples are able to induce aggregation of human bone marrow mesenchymal stem cells, resulting in the formation of smaller nodules compared to the unmodified CTL sample. Over time, the sample with the higher degree of sulfation allows further aggregation between cell clusters while the sample with the lower degree of sulfation shows dissolution of the aggregates.
Topics: Chitosan; Chondrocytes; Glycosaminoglycans; Humans; Lactose; Polysaccharides; Spectroscopy, Fourier Transform Infrared; Sulfates; Sulfur Oxides
PubMed: 35450641
DOI: 10.1016/j.carbpol.2022.119379 -
Journal of Molecular Endocrinology Aug 2018In women, establishment of pregnancy is dependent upon 'fine-tuning' of the endometrial microenvironment, which is mediated by terminal differentiation (decidualisation)... (Review)
Review
In women, establishment of pregnancy is dependent upon 'fine-tuning' of the endometrial microenvironment, which is mediated by terminal differentiation (decidualisation) of endometrial stromal fibroblasts (ESFs). We have demonstrated that intracrine steroid metabolism plays a key role in regulating decidualisation and is essential for time-dependent expression of key factors required for endometrial receptivity. The primary aim of the current study was to determine whether sulphated steroids can act as precursors to bioactive sex steroids during decidualisation. We used primary human ESF and a robust model of decidualisation to assess the expression of genes associated with sulphation, desulphation and transport of sulphated steroids in human ESF as well as the impact of the steroid sulphatase (STS) inhibitor STX64 (Irosustat). We found evidence for an increase in both expression and activity of STS in response to a decidualisation stimulus with abrogation of oestrone biosynthesis and decreased secretion of the decidualisation marker IGFBP1 in the presence of STX64. These results provide novel insight into the contribution of STS to the intracrine regulation of decidualisation.
Topics: Animals; Embryo Implantation; Endometrium; Female; Humans; Pregnancy; Signal Transduction; Steryl-Sulfatase; Sulfates
PubMed: 29720512
DOI: 10.1530/JME-18-0037 -
Marine Drugs Sep 2014Among the three main divisions of marine macroalgae (Chlorophyta, Phaeophyta and Rhodophyta), marine green algae are valuable sources of structurally diverse bioactive... (Review)
Review
Among the three main divisions of marine macroalgae (Chlorophyta, Phaeophyta and Rhodophyta), marine green algae are valuable sources of structurally diverse bioactive compounds and remain largely unexploited in nutraceutical and pharmaceutical areas. Recently, a great deal of interest has been developed to isolate novel sulfated polysaccharides (SPs) from marine green algae because of their numerous health beneficial effects. Green seaweeds are known to synthesize large quantities of SPs and are well established sources of these particularly interesting molecules such as ulvans from Ulva and Enteromorpha, sulfated rhamnans from Monostroma, sulfated arabinogalactans from Codium, sulfated galacotans from Caulerpa, and some special sulfated mannans from different species. These SPs exhibit many beneficial biological activities such as anticoagulant, antiviral, antioxidative, antitumor, immunomodulating, antihyperlipidemic and antihepatotoxic activities. Therefore, marine algae derived SPs have great potential for further development as healthy food and medical products. The present review focuses on SPs derived from marine green algae and presents an overview of the recent progress of determinations of their structural types and biological activities, especially their potential health benefits.
Topics: Chlorophyta; Female; Humans; Male; Phaeophyceae; Polysaccharides; Seaweed; Sulfates
PubMed: 25257786
DOI: 10.3390/md12094984 -
International Journal of Molecular... Oct 2017Sulfated quercetin derivatives are important authentic standards for metabolic studies. Quercetin-3'--sulfate, quercetin-4'--sulfate, and quercetin-3--sulfate as well as...
Sulfated quercetin derivatives are important authentic standards for metabolic studies. Quercetin-3'--sulfate, quercetin-4'--sulfate, and quercetin-3--sulfate as well as quercetin-di--sulfate mixture (quercetin-7,3'-di--sulfate, quercetin-7,4'-di--sulfate, and quercetin-3',4'-di--sulfate) were synthetized by arylsulfotransferase from . Purified monosulfates and disulfates were fully characterized using MS and NMR and tested for their 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS⁺) and ,dimethyl--phenylenediamine (DMPD) radical scavenging, Folin-Ciocalteau reduction (FCR), ferric reducing antioxidant power (FRAP), and anti-lipoperoxidant activities in rat liver microsomes damaged by -butylhydroperoxide. Although, as expected, the sulfated metabolites were usually less active than quercetin, they remained still effective antiradical and reducing agents. Quercetin-3'--sulfate was more efficient than quercetin-4'--sulfate in DPPH and FCR assays. In contrast, quercetin-4'--sulfate was the best ferric reductant and lipoperoxidation inhibitor. The capacity to scavenge ABTS and DMPD was comparable for all substances, except for disulfates, which were the most efficient. Quantum calculations and molecular dynamics simulations on membrane models supported rationalization of free radical scavenging and lipid peroxidation inhibition. These results clearly showed that individual metabolites of food bioactives can markedly differ in their biological activity. Therefore, a systematic and thorough investigation of all bioavailable metabolites with respect to native compounds is needed when evaluating food health benefits.
Topics: Antioxidants; Arylsulfotransferase; Desulfitobacterium; Quercetin; Structure-Activity Relationship; Sulfates
PubMed: 29068411
DOI: 10.3390/ijms18112231 -
International Journal of Molecular... Dec 2022Phenolic acids are known flavonoid metabolites, which typically undergo bioconjugation during phase II of biotransformation, forming sulfates, along with other...
Phenolic acids are known flavonoid metabolites, which typically undergo bioconjugation during phase II of biotransformation, forming sulfates, along with other conjugates. Sulfated derivatives of phenolic acids can be synthesized by two approaches: chemoenzymatically by 3'-phosphoadenosine-5'-phosphosulfate (PAPS)-dependent sulfotransferases or PAPS-independent aryl sulfotransferases such as those from , or chemically using SO complexes. Both approaches were tested with six selected phenolic acids (2-hydroxyphenylacetic acid (2-HPA), 3-hydroxyphenylacetic acid (3-HPA), 4-hydroxyphenylacetic acid (4-HPA), 3,4-dihydroxyphenylacetic acid (DHPA), 3-(4-hydroxyphenyl)propionic acid (4-HPP), and 3,4-dihydroxyphenylpropionic acid (DHPP)) to create a library of sulfated metabolites of phenolic acids. The sulfates of 3-HPA, 4-HPA, 4-HPP, DHPA, and DHPP were all obtained by the methods of chemical synthesis. In contrast, the enzymatic sulfation of monohydroxyphenolic acids failed probably due to enzyme inhibition, whereas the same reaction was successful for dihydroxyphenolic acids (DHPA and DHPP). Special attention was also paid to the counterions of the sulfates, a topic often poorly reported in synthetic works. The products obtained will serve as authentic analytical standards in metabolic studies and to determine their biological activity.
Topics: Phosphoadenosine Phosphosulfate; Sulfotransferases; Sulfates; Hydroxybenzoates
PubMed: 36499496
DOI: 10.3390/ijms232315171