Oxidized sterols as a significant component of dissolved organic matter: Evidence from 2D HPLC in combination with 2D and 3D NMR spectroscopy

Water Research

Volumn 46, Issue 10, 2012, Pages 3398-3408

  Woods, Gwen C ^a   Simpson, Myrna J ^a   Simpson, André J ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Hydrophilic interaction chromatography; Molecular characterization; Natural organic matter; Nuclear magnetic resonance spectroscopy; Refractory components; Terpenoids

Indexed keywords

ALCOHOLS; BIOGEOCHEMISTRY; HYDROPHILICITY; LIPIDS; LIQUID CHROMATOGRAPHY;

HYDROPHILIC INTERACTION CHROMATOGRAPHY; MOLECULAR CHARACTERIZATION; NATURAL ORGANIC MATTERS; REFRACTORY COMPONENTS; TERPENOIDS;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALICYCLIC COMPOUND; CARBON; CARBOXYLIC ACID DERIVATIVE; DISSOLVED ORGANIC MATTER; HYDROXYL GROUP; METHYL GROUP; STEROL DERIVATIVE;

CARBOXYLIC ACID; DISSOLVED ORGANIC MATTER; FRACTIONATION; LIQUID CHROMATOGRAPHY; MOLECULAR ANALYSIS; NUCLEAR MAGNETIC RESONANCE; REFRACTION; STEROL; TERPENE;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; FRACTIONATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RIVER; TWO DIMENSIONAL HYDROPHILIC INTERACTION CHROMATOGRAPHY;

EID: 84861195039     PISSN: 00431354     EISSN: 18792448     Source Type: Journal    
DOI: 10.1016/j.watres.2012.03.040     Document Type: Article

References (47)

1. Bax A. A spatially selective composite 90° radiofrequency pulse. Journal of Magnetic Resonance 1985, 65(1):142-145.
2. Benner R. Biogeochemistry of Marine Dissolved Organic Matter 2002, 59-90. Academic Press, San Diego. D.A. Hansell, C.A. Carlson (Eds.).
3. Christodoulou S., Marty J.-C., Miquel J.-C., Volkman J.K., Rontani J.-F. Use of lipids and their degradation products as biomarkers for carbon cycling in the northwestern Mediterranean Sea. Marine Chemistry 2009, 113(1-2):25-40.
4. Cicero D.O., Barbato G., Bazzo R. Sensitivity enhancement of a two-dimensional experiment for the measurement of heteronuclear long-range coupling constants, by a new scheme of coherence selection by gradients. Journal of Magnetic Resonance 2001, 148(1):209-213.
5. De Fabiani E., Mitro N., Gilardi F., Crestani M. Sterol-protein interactions in cholesterol and bile acid synthesis. Subcellular Biochemistry 2010, 51:109-135.
6. Deshmukh A.P., Pacheco C., Hay M.B., Myneni S.C.B. Structural environments of carboxyl groups in natural organic molecules from terrestrial systems. Part 2: 2D NMR spectroscopy. Geochimica et Cosmochimica Acta 2007, 71(14):3533-3544.
7. Dittmar T., Paeng J. A heat-induced molecular signature in marine dissolved organic matter. Nature Geoscience 2009, 2(3):175-179.
8. Druffel E.R.M., Williams P.M., Bauer J.E., Ertel J.R. Cycling of dissolved and particulate organic matter in the open ocean. Journal of Geophysical Research 1992, 97(C10):15639-15659.
9. Dubey V.S., Bhalla R., Luthra R. An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants. Journal of Bioscience 2003, 28(5):637-646.
10. Engel A., Thoms S., Riebesell U., Rochelle-Newall E., Zondervan I. Polysaccharide aggregation as a potential sink of marine dissolved organic carbon. Nature 2004, 428:929-932.
11. Gagosian R.B., Smith S.O., Nigrelli G.E. Vertical transport of steroid alcohols and ketones measured in a sediment trap experiment in the equatorial Atlantic Ocean. Geochimica et Cosmochimica Acta 1982, 46(7):1163-1172.
12. Haiber S., Herzog H., Burba P., Gosciniak B., Lambert J. Two-dimensional NMR studies of size fractionated Suwannee River fulvic and humic acid reference. Environmental Science and Technology 2001, 35(21):4289-4294.
13. 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(4):202-211.
14. Hedges J.I. Biogeochemistry of Marine Dissolved Organic Matter 2002, 1-33. Academic Press, San Diego. D.A. Hansell, C.A. Carlson (Eds.).
15. 13C-NMR spectrometry. Geochimica et Cosmochimica Acta 1992, 56(4):1753-1757.
16. Hemström P., Irgum K. Hydrophilic interaction chromatography. Journal of Separation Science 2006, 29(12):1784-1821.
17. Hernes P.J., Hedges J.I., Peterson M.L., Wakeham S.G., Lee C. Neutral carbohydrate geochemistry of particulate material in the central equatorial Pacific. Deep Sea Research Part II 1996, 43(4-6):1181-1204.
18. Hernes P.J., Benner R., Cowie G.L., Goñi M.A., Bergamaschi B.A., Hedges J.I. Tannin diagenesis in mangrove leaves from a tropical estuary: a novel molecular approach. Geochimica et Cosmochimica Acta 2001, 65(18):3109-3122.
19. Hertkorn N., Benner R., Frommberger M., Schmitt-Kopplin P., Witt M., Kaiser K., Kettrup A., Hedges J.I. Characterization of a major refractory component of marine dissolved organic matter. Geochimica et Cosmochimica Acta 2006, 70(12):2990-3010.
20. Koch B.P., Dittmar T., Witt M., Kattner G. Fundamentals of molecular formula assignment to ultrahigh resolution mass data of natural organic matter. Analytical Chemistry 2007, 79(4):1758-1763.
21. Lam B., Simpson A.J. Investigating aggregation in Suwannee River (USA) dissolved organic matter using diffusion-ordered nuclear magnetic resonance spectroscopy. Environmental Toxicology and Chemistry 2009, 28(5):931-939.
22. Lam B., Baer A., Alaee M., Lefebvre B., Moser A., Williams A., Simpson A.J. Major structural components in freshwater dissolved organic matter. Environmental Science and Technology 2007, 41(24):8240-8247.
23. Laureillard J., Saliot A. Biomarkers in organic matter produced in estuaries: a case study of the Krka estuary (Adriatic Sea) using the sterol marker series. Marine Chemistry 1993, 43(1-4):247-261.
24. Leenheer J.A., Rostad C.E. Tannins and Terpenoids as Major Precursors of Suwannee River Fulvic Acid 2004, U.S. Geological Survey Scientific Investigations Report 2004-5276, p. 16.
25. Leenheer J.A., Nanny M.A., McIntyre C. Terpenoids as major precursors of dissolved organic matter in landfill leachates, surface water, and groundwater. Environmental Science and Technology 2003, 37(11):2323-2331.
26. Liu Y., Guo Z., Feng J., Xue X., Zhang F., Xu Q., Liang X. Development of orthogonal two-dimensional hydrophilic interaction chromatography systems with the introduction of novel stationary phases. Journal of Separation Science 2009, 32(17):2871-2876.
27. Lütjohann D. Sterol autoxidation: from phytosterols to oxyphytosterols. British Journal of Nutrition 2004, 91(1):3-4.
28. 3-carene, limonene, and α-terpinene. Environmental Science and Technology 1999, 33(22):4029-4033.
29. Obernosterer I., Benner R. Competition between biological and photochemical processes in the mineralization of dissolved organic carbon. Limnology and Oceanography 2004, 49(1):117-124.
30. Owen R.W., Bilton R.F. The degradation of cholic acid by Pseudomonas sp. N.C.I.B. 10590 under anaerobic conditions. Biochemical Journal 1983, 216:641-654.
31. Parish E.J. Physiology and Biochemistry of Sterols 1991, 324-336. American Oil Chemists' Society, Champaign, Illinois. G.W. Patterson, W.D. Nes (Eds.).
32. Rontani J.-F., Zabeti N., Wakeham S.G. Degradation of particulate organic matter in the equatorial Pacific Ocean: biotic or abiotic?. Limnology and Oceanography 2011, 56(1):333-349.
33. Saliot A., Mejanelle L., Scribe P., Fillaux J., Pepe C., Jabaud A., Dagaut J. Particulate organic carbon, sterols, fatty acids and pigments in the Amazon River system. Biogeochemistry 2001, 53(1):79-103.
34. Sarma N.S., Krishna M.S., Pasha S.G., Rao T.S.P., Venkateswarlu Y., Parameswaran P.S. Marine metabolites: the sterols of soft coral. Chemical Reviews 2009, 109(6):2803-2828.
35. 2 atmosphere. Environmental Science and Technology 1998, 32(17):2531-2541.
36. Simpson A.J. Determining the molecular weight, aggregation, structures and interactions of natural organic matter using diffusion ordered spectroscopy. Magnetic Resonance in Chemistry 2002, 40(13):S72-S82.
37. Simpson A.J., Burdon J., Graham C.L., Hayes M.H.B., Spencer N., Kingery W.L. Interpretation of heteronuclear and multidimensional NMR spectroscopy of humic substances. European Journal of Soil Science 2001, 52(3):495-509.
38. Simpson A.J., Kingery W.L., Hatcher P.G. The identification of plant derived structures in humic materials using three-dimensional NMR spectroscopy. Environmental Science and Technology 2003, 37(2):337-342.
39. Simpson A.J., McNally D.J., Simpson M.J. NMR spectroscopy in environmental research: from molecular interactions to global processes. Progress in Nuclear Magnetic Resonance Spectroscopy 2011, 58(3-4):97-175.
40. Smith L.L. Cholesterol Autoxidation 1981, Plenum Press, New York.
41. Stoll D.R., Li X., Wang X., Carr P.W., Porter S.E.G., Rutan S.C. Fast, comprehensive two-dimensional liquid chromatography. Journal of Chromatography A 2007, 1168(1-2):3-43.
42. Sulzberger B., Durisch-Kaiser E. Chemical characterization of dissolved organic matter (DOM): a prerequisite for understanding UV-induced changes of DOM absorption properties and bioavailability. Aquatic Science 2009, 71(2):104-126.
43. Summons R.E., Bradley A.S., Jahnke L.L., Waldbauer J.R. Steroids, triterpenoids and molecular oxygen. Philosophical Transactions of the Royal Society of London, Series B: Biological Sciences 2006, 361(1470):951-968.
44. Szentirmai A. Microbial physiology of sidechain degradation of sterols. Journal of Industrial Microbiology 1990, 6(2):101-115.
45. Woods G.C., Simpson M.J., Koerner P.J., Napoli A., Simpson A.J. HILIC-NMR: toward the identification of individual molecular components in dissolved organic matter. Environmental Science and Technology 2011, 45(9):3880-3886.
46. Wu D., Chen A., Johnson C.S. An improved diffusion-ordered spectroscopy experiment incorporating bipolar-gradient pulses. Journal of Magnetic Resonance Series A 1995, 115(2):260-264.
47. Zwenger S., Basu C. Plant terpenoids: applications and future potentials. Biotechnology and Molecular Biology Reviews 2008, 3(1):1-7.