Molecular level characterization of methyl sugars in marine high molecular weight dissolved organic matter

Marine Chemistry

Volumn 154, Issue , 2013, Pages 34-45

  Panagiotopoulos, Christos ^a,b   Repeta, Daniel J ^c   Mathieu, Laura ^a,b   Rontani, Jean François ^a,b   Sempéré, Richard ^a,b  

^a AIX MARSEILLE UNIVERSITY   (France)

^b STATION MARINE D ENDOUME   (France)

^c WOODS HOLE OCEANOGRAPHIC INSTITUTION   (United States)

Author keywords

3,6 Dideoxysugars; Acyl polysaccharides (APS); Anhydrosugars; Chemical synthesis of methylated sugars; GC MS; Heptoses; High molecular weight dissolved organic matter (HMWDOM); Methylated sugars

Indexed keywords

ALGA; BACTERIUM; CONCENTRATION (COMPOSITION); DISSOLVED ORGANIC MATTER; MOLECULAR ANALYSIS; POLYSACCHARIDE; SEAWATER; SUGAR; ULTRAFILTRATION;

HAWAII [UNITED STATES]; PACIFIC OCEAN; PACIFIC OCEAN (NORTH); UNITED STATES;

ALGAE; BACTERIA (MICROORGANISMS);

EID: 84878516885     PISSN: 03044203     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.marchem.2013.04.003     Document Type: Article

References (84)

1. Aluwihare L.I., Repeta D.J., Chen R.F. A major biopolymeric component to dissolved organic carbon in surface water. Nature 1997, 387:166-169.
2. Aluwihare L.I., Repeta D.J. A comparison of the chemical characteristics of oceanic DOM and extracellular DOM produced by marine algae. Mar. Ecol. Prog. Ser. 1999, 186:105-117.
3. Bacon J.S.D., Cheshire M.V. Apiose and mono-O-methyl sugars as minor constituents of the leaves of deciduous trees and various other species. Biochem. J. 1971, 124:555-562.
4. Bauer J.E. Carbon isotopic composition of DOM. Biogeochemistry of Marine Dissolved Organic Matter 2002, 405-453. Academic Press. D.A. Hansell, C.A. Carlson (Eds.).
5. Benner R., Pakulski J.D., McCarthy M., Hedges J.I., Hatcher P.G. Bulk chemical characteristics of dissolved organic matter in the ocean. Science 1992, 255:1562-1564.
6. Benner R. Chemical composition and reactivity. Biogeochemistry of Marine Dissolved Organic Matter 2002, 59-90. Academic Press. D.A. Hansell, C.A. Carlson (Eds.).
7. Bergamaschi B.A., Walters J.S., Hedges J.I. Distributions of uronic acids and O-methyl sugars in sinking and sedimentary particles in two coastal marine environments. Geochim. Cosmochim. Acta 1999, 63:413-425.
8. Bhatia M.P., Das S.B., Longnecker K., Charette M.A., Kujawinski E.B. Molecular characterization of dissolved organic matter associated with the Greenland ice sheet. Geochim. Cosmochim. Acta 2010, 74:3768-3784.
9. Björndal H., Lindberg B., Svensson S. Mass spectrometry of partially methylated alditol acetates. Carbohydr. Res. 1967, 5:433-440.
10. Boon J.J., Klap V.A., Eglinton T.I. Molecular characterization of microgram amounts of oceanic colloid organic matter by direct temperature-resolved ammonia chemical ionization mass spectrometry. Org. Geochem. 1998, 29:1051-1061.
11. Borch N.H., Kirchman D.L. Concentration and compositionof dissolved combined neutral sugars (polysaccharides) inseawater determined by HPLC-PAD. Mar. Chem. 1997, 57:85-95.
12. Brennan P.J., Mayer H., Aspinall G.O., Nam Shin J.E. Structures of the glycopeptidolipid antigens from serovars in the Mycobacterium avium/Mycobacterium intracellulare/Mycobacterium scrofulaceum serocomplex. Eur. J. Biochem. 1981, 115:7-15.
13. Bronk D. Dynamics of DON. Biogeochemistry of Marine Dissolved Organic Matter 2002, 153-247. Academic Press. D.A. Hansell, C.A. Carlson (Eds.).
14. Carlson C.A. Production and removal processes. Biogeochemistry of Marine Dissolved Organic Matter 2002, 91-151. Academic Press. D.A. Hansell, C.A. Carlson (Eds.).
15. Carpenter L.J., Lewis A.C., Hopkins J.R., Read K.A., Longley I.D., Gallagher M.W. Uptake of methanol to the North Atlantic Ocean surface. Glob. Biogeochem. Cycles 2004, 18:GB4027. 10.1029/2004GB002294.
16. Chassagne D., Crouzet J., Bayonove C.L., Baumes R.L. Identification of passion fruit glycosides by gas chromatography/mass spectrometry. J. Agr. Food Chem. 1998, 46:4352-4357.
17. Chiovitti A., Harper R.E., Willis A., Bacic A., Mulvaney P., Wetherbee R. Variations in the substituted 3-linked mannans closely associated with the silicified walls of diatoms. J. Phycol. 2005, 41:1154-1161.
18. Choma A., Russa R., Mayer H., Lorkiewicz Z. Chemical analysis of Azospirillum lipopolysaccharides. Arc. Microbiol. 1987, 146:341-345.
19. Ciucanu I., Kerek F. A simple and rapid method for the permethylation of carbohydrates. Carbohyd. Res. 1984, 131:209-217.
20. Conrad R.S., Kist M., Schlecht S., Galanos C. Extraction and biochemical analyses of Helicobacter pylori lipopolysaccharides. Curr. Microbiol. 1992, 24:165-169.
21. Dittmar T., Fitznar H.P., Kattner G. Origin and biogeochemical cycling of organic nitrogen in the eastern Arctic Ocean as evident from d- and l-amino acids. Geochim. Cosmochim. Acta 2001, 65:4103-4114.
22. Druffel E.R.M., Williams P.M., Bauer J.E., Ertel J.R. Cycling of dissolved and particulate organic matter in the open ocean. J. Geophys. Res. 1992, 97:15639-15659.
23. Eglinton T.I., Repeta D.J. Marine organic geochemistry. Treatise on Geochemistry 2004, vol. 7:145-180. Elsevier. H. Elderfield (Ed.).
24. Evans L.V., Callow M.E., Percival E., Fareed V. Studies on the synthesis and composition of extracellular mucilage in the unicellular red alga Rhodella. J. Cell Sci. 1974, 6:1-21.
25. Fichtinger-Schepman A.M.J., Kamerling J.P., Vliegenthart J.F.G., de Jong E.W., Bosch L., Westbroek P. Composition of a methylated, acidic polysaccharide associated with coccoliths of Emiliania huxleyi (Lohmann) Kamptner. Carbohyd. Res. 1979, 69:181-189.
26. Fox A., Black G.E., Fox K., Rostovtseva S. Determination of carbohydrate profiles of Bacillus anthracis and Bacillus cereus including identification of O-methyl methylpentose by using gas chromatography-mass spectrometry. J. Clin. Microbiol. 1993, 31:887-894.
27. Fox K.F., Fox A., Nagpal M., Steinberg P., Heroux K. Identification of Brucella by ribosomal-spacer-region PCR and differentiation of Brucella canis from other Brucella spp. pathogenic for humans by carbohydrate profiles. J. Clin. Microbiol. 1998, 36:3217-3222.
28. Fox A. Carbohydrates profiling of bacteria by gas chromatography-mass spectrometry and their trace detection in complex matrices by gas chromatography-tandem mass spectrometry. J. Chromatogr. A 1999, 843:287-300.
29. Gogou A., Repeta D.J. Particulate-dissolved transformations as a sink for semi-labile dissolved organic matter: chemical characterization of high molecular weight dissolved and surface-active organic matter in seawater and in diatom cultures. Mar. Chem. 2010, 121:215-223.
30. Goldberg S.J., Carlson C.A., Brzezinski M., Nelson N.B., Siegel D.A. Systematic removal of neutral sugars within dissolved organic matter across ocean basins. Geophys. Res. Lett. 2011, 38. L17606. 10.1029/2011GL048620.
31. Gorshkova R.P., Zubkov V.A., Isakov V.V., Ovodov Y.S. Yersiniose, a new branched-chain sugar. Carbohyd. Res. 1984, 126:308-312.
32. Hansell D.A., Carlson C.A., Repeta D.J., Schlitzer R. Dissolved organic matter in the ocean: a controversy stimulates new insights. Oceanography 2009, 22:202-211.
33. Hansell D.A., Carlson C.A., Schlitzer R. Net removal of major marine dissolved organic carbon fractions in the subsurface ocean. Global Biogeochem. Cycles 2012, 26. 10.1029/2011GB004069.
34. Hedges J.I. Global biogeochemical cycles: progress and problems. Mar. Chem. 1992, 39:67-93.
35. Hertkorn N., Benner R., Fommberger M., Schmitt-Kopplin P., Witt M., Kaiser K., Kettruo A., Hedges J.I. Characterization of a major refractory component of marine dissolved organic matter. Geochim. Cosmochim. Acta 2006, 70:2990-3010.
36. Hockadey W.C., Purcell J.M., Marshall A.G., Baldock J.A., Hatcher P.G. Electrospray and photoionization mass spectrometry for the characterization of organic matter in natural waters: a qualitative assessment. Limnol. Oceanogr. Methods 2009, 7:81-95.
37. Janse I., Van Rijssel M., Gottschat J.C., Lancelot C., Gieskes W.W.C. Carbohydrate in the North Sea during spring blooms of Phaeocystis: a specific fingerprint. Aquat. Microb. Ecol. 1996, 10:97-103.
38. Jones V., Collins M.J., Penkman K.E.H., Jaffe R., Wolff G.A. An assessment of the microbial contribution to aquatic dissolved organic nitrogen using amino acid enantiomeric ratios. Org. Geochem. 2005, 36:1099-1107.
39. Kaiser K., Benner R. Major bacterial contribution to the ocean reservoir of detrital organic carbon and nitrogen. Limnol. Oceanogr. 2008, 53:99-112.
40. Kaiser K., Benner R. Biochemical composition and size distribution of organic matter at the Pacific and Atlantic time-series stations. Mar. Chem. 2009, 113:63-77.
41. Klok J., Cox H.C., Baas M., Schuyl P.J.W., de Leeuw J.W., Schenck P.A. Carbohydrates in recent marine sediments-I. Origin and significance of deoxy- and O-methyl-monosaccharides. Org. Geochem. 1984, 7:73-84.
42. Koch B.P., Ludwichowski K.-U., Kattner G., Dittmar T., Witt M. Advanced characterization of marine dissolved organic matter by combining reversed-phase liquid chromatography and FT-ICR-MS. Mar. Chem. 2008, 111:233-241.
43. Kujawinski E.B., Behn M.D. Automated analysis of electrospray ionization Fourier transform ion cyclotron resonance mass spectra of natural organic matter. Anal. Chem. 2006, 78:4363-4373.
44. Landry C., Tremblay L. Compositional differences between size classes of dissolved organic matter from freshwater and seawater revealed by an HPLC-FTIR System. Environ. Sci. Technol. 2012, 46:1700-1707.
45. Mattos K.A., Todeschini A.R., Heise N., Jones C., Previato J.O., Mendonça-Previato L. Nitrogen-fixing Burkholderia brasiliensis produces a novel yersiniose A-containing O-polysaccharide. Glycobiology 2005, 15:313-321.
46. Mayer H., Framberg K., Weckesser J. 6-O-methyl-d-glucosamine in lipopolysaccharides of Rhodopseudomonas palustris strains. Eur. J. Biochem. 1974, 44:181-187.
47. McCarren J., Becker J.W., Repeta D.J., Shi Y., Young C.R., Malstrom R.R., Chisholm S.W., Delong E.F. Microbial community transcriptomes reveal microbes and metabolic pathways associated with dissolved organic matter turnover in the sea. Proc. Natl. Acad. Sci. U. S. A. 2010, 107:16420-16427.
48. McCarthy M., Hedges J.I., Benner R. Major biochemical composition of dissolved high molecular weight organic matter in seawater. Mar. Chem. 1996, 55:281-297.
49. McCarthy M., Hedges J.I., Benner R. Major bacterial contribution to marine dissolved organic nitrogen. Science 1998, 281:231-234.
50. Minor E.C., Simpouw J.-P., Boon J.J., Kerkhoff A.E., van der Horst J. Estuarine/marine UDOM as characterized by size-exclusion chromatography and organic mass spectroscopy. Mar. Chem. 2002, 78:75-102.
51. Minor E.C., Steinbring C.J., Longnecker K., Kujawinski E.B. Characterization of dissolved organic matter in lake superior and its watershed using ultrahigh resolution mass spectrometry. Org. Geochem. 2012, 43:1-11.
52. Moers M.E.C., Baas M., Boon J.J., De Leeuw J.W. Molecular characterization of total organic matter and carbohydrates in peat samples from a cypress swamp by pyrolysis-mass spectrometry and wet-chemical methods. Biogeochemistry 1990, 11:251-277.
53. Mopper K., Kieber D.J. Photochemistry and the cycling of carbon, sulfur, nitrogen and phosphorus. Biogeochemistry of Marine Dissolved Organic Matter 2002, 455-489. Academic Press. D.A. Hansell, C.A. Carlson (Eds.).
54. Mopper K., Stubbins A., Ritchie J.D., Bialk H.M., Hatcher P.G. Advanced instrumental approaches for characterization of marine dissolved organic matter: extraction techniques, mass spectrometry, and nuclear magnetic resonance spectroscopy. Chem. Rev. 2007, 107:419-442.
55. Nelson N.B., Siegel D.A. Chromophoric DOM in the open ocean. Biogeochemistry of Marine Dissolved Organic Matter 2002, 547-578. Academic Press. D.A. Hansell, C.A. Carlson (Eds.).
56. Neufeld J.D., Boden R., Moussard H., Schäfer H., Murrell J.C. Substrate-specific clades of active marine methylotrophs associated with a phytoplankton bloom in a temperate coastal environment. Appl. Environ. Microbiol. 2008, 74:7321-7328.
57. Ogawa K., Yamaura M., Maruyama I. Isolation and identification of 2-O-methyl-l-rhamnose and 3-O-methyl-l-rhamnose as constituents of an acidic polysaccharide of Chlorella vulgaris. Biosci. Biotechnol. Biochem. 1997, 61:539-540.
58. Ogner G. Analysis of the carbohydrates of fulvic and humic acids as their partially methylated alditol acetates. Geoderma 1980, 23:1-10.
59. Panagiotopoulos C., Sempéré R. Analytical methods for the determination of sugars in marine samples: a historical perspective and future directions. Limnol. Oceanogr. Methods 2005, 3:419-454.
60. Panagiotopoulos C., Repeta D.J., Johnson C.G. Characterization of methyl sugars, 3-deoxysugars and methyl deoxysugars in marine high molecular weight dissolved organic matter. Org. Geochem. 2007, 38:884-896.
61. Panagiotopoulos C., Wurl O. Spectrophotometric and chromatographic analysis of carbohydrates in marine samples. Practical Guidelines for the Analysis of Seawater 2009, 49-65. Taylor and Francis. O. Wurl (Ed.).
62. Popper Z.A., Sadler I.H., Fry S.C. 3-O-methylrhamnose in lower land plant primary cell walls. Biochem. Syst. Ecol. 2004, 32:279-289.
63. Quan T.M., Repeta D.J. Periodate oxidation of marine high molecular weight dissolved organic matter: Evidence for a major contribution from 6-deoxy- and methyl sugars. Mar. Chem. 2007, 105:183-193.
64. Reemtsma T., These A., Linscheid M., Leenheer J., Spitzy A. Molecular and structural characterization of dissolved organic matter from deep ocean by FTICR-MS, including hydrophilic nitrogenous organic molecules. Environ. Sci. Technol. 2008, 42:1430-1437.
65. Repeta D.J., Quan T.M., Aluwihare L.I., Accardi A.M. Chemical characterization of high molecular weight dissolved organic matter in fresh and marine waters. Geochim. Cosmochim. Acta 2002, 66:955-962.
66. Repeta D.J., Aluwihare L.I. Radiocarbon analysis of neutral sugars in high-molecular-weight dissolved organic carbon: implications for organic carbon cycling. Limnol. Oceanogr. 2006, 51:1045-1053.
67. Sassaki G.L., Gorin P.A.J., Souza L.M., Czelusniak P.A., Iacomini M. Rapid synthesis of partially O-methylated alditol acetate standards for GC-MS: some relative activities of hydroxyl groups of methyl glycopyranosides on Purdie methylation. Carbohyd. Res. 2005, 340:731-739.
68. Schmidt W., Drews G., Weckesser J., Fromme I., Borowiak D. Characterization from eight strains of the cyanobacterium Synechococcus. Arch. Microbiol. 1980, 127:209-215.
69. Schuring F., Smeenk J.W., Homan W.L., Alan Musgrave A., Van den Ende H. Occurrence of O-methylated sugars in surface glycoconjugates in Chlamydomonas eugametos. Planta 1987, 170:322-327.
70. Sempéré R., Tedetti M., Panagiotopoulos C., Charrière B., Van Wambeke F. Distribution and bacterial availability of dissolved neutral sugars in the south east Pacific. Biogeosciences 2008, 5:1165-1173.
71. Shekharam K.M., Venkataraman L.V., Salimath P.V. Carbohydrate composition and characterization of two unusual sugars from the blue green alga, Spirulina platensis. Phytochemistry 1987, 26:2267-2269.
72. Simkovic I., Surina I., Vrican M. Primary reactions of sucrose thermal degradation. J. Anal. Appl. Pyrol. 2003, 70:493-504.
73. Simoneit B.R.T., Schauer J.J., Nolte C.G., Oros D.R., Elias V.O., Fraser M.P., Rogge W.F., Cass G.R. Levoglucosan, a tracer for cellulose in biomass burning and atmospheric particles. Atmos. Environ. 1999, 33:173-182.
74. Simoneit B.R.T., Elias V.O. Organic tracers from biomass burning in atmospheric particulate matter over the ocean. Mar. Chem. 2000, 69:301-312.
75. Skoog A., Benner R. Aldoses in various size fractions of marine organic matter. Implications for carbon cycling. Limnol. Oceanogr. 1997, 42:1803-1813.
76. Stepan H., Bleckmann C., Geyer H., Geyer R., Staudacher E. Determination of 3-O- and 4-O-methylated monosaccharide constituents in snail glycans. Carbohyd. Res. 2010, 345:1504-1507.
77. Tedetti M., Kawamura K., Charriere B., Chevalier N., Sempéré R. Determination of low molecular weight dicarboxylic and ketocarboxylic acids in seawater samples. Anal. Chem. 2006, 78:6012-6018.
78. Tharanathan R.N., Mayer H., Weckesser J. Location of O-methyl sugars in antigenic (Lipo-)polysaccharides of photosynthetic bacteria and cyanobacteria. J. Biochem. 1978, 171:403-408.
79. Vetter T.A., Perdue E.M., Ingall R., Koprivnjak J.-F., Pfromm P.H. Combining reverse osmosis and electrodialysis for more complete recovery of dissolved organic matter from seawater. Sep. Purif. Technol. 2007, 56:383-387.
80. Wang Z.F., He Y., Huang L.J. An alternative method for the rapid synthesis of partially O-methylated alditol acetate standards for GC-MS analysis of carbohydrates. Carbohyd. Res. 2007, 342:2149-2151.
81. Weckesser J., Mayer H., Drews G. The identification of 3-O-methyl-l-rhamnose (l-acofriose) as constituent of the lipopolysaccharide of Rhodopseudomonas capsulata. Eur. J. Biochem. 1970, 16:158-160.
82. Wells M.L. Marine colloids and trace metals. Biogeochemistry of Marine Dissolved Organic Matter 2002, 367-404. Academic Press. D.A. Hansell, C.A. Carlson (Eds.).
83. Williams P.M., Druffel E.R.M. Radiocarbon in dissolved organic matter in the central North Pacific Ocean. Nature 1987, 330:246-248.
84. Woods G.C., Simpson M.J., Kellheer B.P., McCaul M., Kingery W.L., Simpson A.J. Online high-performance size exclusion chromatography-nuclear magnetic resonance for the characterization of dissolved organic matter. Environ. Sci. Technol. 2010, 44:624-630.