Maleimides (1H-pyrrole-2,5-diones) as molecular indicators of anoxygenic photosynthesis in ancient water columns

Geochimica et Cosmochimica Acta

Volumn 60, Issue 20, 1996, Pages 3913-3924

  Grice, Kliti ^a,c   Gibbison, Robert ^a   Atkinson, Jane E ^a   Schwark, Lorenz ^b   Eckardt, Christian B ^a,d   Maxwell, James R ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b UNIVERSITY OF COLOGNE   (Germany)

^c ROYAL NETHERLANDS INSTITUTE FOR SEA RESEARCH   (Netherlands)

^d PETROBRAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ANOXIA; BACTERIA; CHLOROBIACEAE; MALEIMIDE; MARINE SEDIMENT; ORGANIC GEOCHEMISTRY; PHOTOSYNTHESIS;

EID: 0030423512     PISSN: 00167037     EISSN: None     Source Type: Journal    
DOI: 10.1016/0016-7037(96)00199-8     Document Type: Article

References (59)

1. Bogacheva M. P. and Galimov E. M. (1979) Intramolecular distribution of carbon isotopes in chlorophyll and hemin. Geokhimiya 7, 1166-1172.
2. Brown S. B., Smith K. M., Bisset G. M. F., and Troxler R. F. (1980) Mechanism of photo-oxidation of bacteriochlorophyll c derivatives. A possible model for chlorophyll breakdown. J. Biol. Chem. 255, 8063-8068.
3. Callot H. J. (1991) Geochemistry of chlorophylls. In Chlorophylls (ed. H. Scheer), pp. 339. CRC Press.
4. Chicarelli M. I, Kaur S., and Maxwell J. R. (1987) Sedimentary porphyrins: Unexpected structures, occurrence, and possible origins. In Complexes in Fossil Fuels (ed. H. D. Filby and J. F. Branthaver); Amer. Chem. Soc. Symposium. Series. 344, 41-67.
5. Eckardt C. B., Wolf M., and Maxwell J. R. (1989) Iron porphyrins in the Permian Kupferschiefer of the Lower Rhine Basin, North West Germany. Org. Geochem. 14, 659-666.
6. Evans M. C. W., Buchanan B. B., and Arnon D. I. (1966) A new ferredoxin-dependent carbon reduction cycle in a photosynthetic bacterium. Biochemistry 55, 928-934.
7. Freeman K. H., Hayes J. M., Trendel J. M., and Albrecht P. (1990) Evidence from carbon isotope measurements for diverse origins of sedimentary hydrocarbons. Nature 343, 254-256.
8. Galimov E. M. (1977) Investigation of the distribution of carbon isotopes in biogenic compounds. Proc. VIII International Congress on Organic Geochemistry. Nauka.
9. Grassel M., Coy U., Seyffer T. R., and Lynen F. (1963) Die chemische Konstitution des Cytohamins. Biochem. Z. 338, 771-795.
10. Grice K., Schaeffer P., Schwark L., and Maxwell J. R. (1996) Molecular indicators of palaeoenvironmental conditions in an immature Permian shale (Kupferschiefer, Lower Rhine Basin, northwestern Germany) from free and S-bound lipids. (in press)
11. Harris P. G., Pearce G. E. S., Peakman T. M., and Maxwell J. R. (1995) A widespread and abundant chlorophyll transformation product in aquatic environments. Org. Geochem. 23, 183-187.
12. Hartgers W. A., Koopmans M. P., Sinninghe Damsté J. S., and De Leeuw J. W. (1993) Sedimentary evidence for a diaromatic carotenoid with an unprecedented aromatic substitution pattern. J. Chem. Soc. Chem. Comm. 23, 1715-1716.
13. Hartgers W. A., Sinninghe Damsté J. S., and De Leeuw J. W. (1994a) A molecular and carbon isotopic study towards the origin and diagenetic fate of diaromatic carotenoids. Org. Geochem. 22, 703-725.
14. Hartgers W. A., Sinninghe Damsté J. S., Requejo A. G., Allan J., Hayes J. M., and De Leeuw J. W. (1994b) Evidence for only minor contributions from bacteria to sedimentary organic carbon. Nature 369, 224-227.
15. Harvey D. J. (1978) Comparison of fourteen substituted silyl derivatives for the characterisation of alcohols, steroids and cannabinoids by gas-liquid chromatography and mass spectrometry. J. Chrom. 147, 291-298.
16. Hayes J. M., Freeman K. H., Popp B. N., and Hoham C. H. (1990) Compound-specific isotopic analyses: A novel tool for reconstruction of ancient biogeochemical processes. Org. Geochem. 16, 1115-1128.
17. 13C lipids from marine particulates. In Organic Geochemistry (ed. J. O. Grimait); Developments and Applications to Energy, Climate, Environment, and Human History, pp. 10-11. Donostia-San Sebastian.
18. Jen J. J. and MacKinney G. (1970a) On the photodecomposition of chlorophyll in vitro-I. Reaction rates. Photochem. Photobiol. 11, 297-302.
19. Jen J. J. and MacKinney G.(1970b) On the photodecomposition of chlorophyll in vitro-II Intermediates and breakdown products. Photochem. Photobiol. 11, 303-308.
20. 13C values of sedimentary straight chain and cyclic alcohols by GC-IRMS. Biol. Mass Spec. 20, 641-646.
21. Keely B. J. and Maxwell J. R. (1993) The Mulhouse basin: Evidence from porphyrin distributions for water column anoxia during deposition of marls. Org. Geochem. 20, 1217-1225.
22. Keely B. J., Prowse W. G., and Maxwell J. R. (1990) The Treibs hypothesis: An evaluation based on structural studies. Energy Fuels 4, 628-634.
23. Keely B. J., Harris P. J., Popp B. N., Hayes J. M., Meischner D., and Maxwell J. R. (1994) Porphyrins and chlorin distributions in a Late Pliocene lacustrine sediment. Geochim. Cosmochim. Acta, 58, 3691-3701.
24. Keely B. J., Blake S. R., Schaeffer P., and Maxwell J. R. (1995) Distributions of pigments in the organic matter of marls from the Vena del Gesso evaporitic sequence. Org. Geochem. 23, 527-539.
25. Kohnen M. E. L., Schouten S., Sinninghe-Damsté J. S., De Leeuw J. W., Merritt D. M., and Hayes J. M. (1992) Recognition of palaeobiochemicals by a combined molecular sulphur and isotope geochemical approach. Science 256, 358-361.
26. Madigan M. T., Takigiku R., Lee R. G., Gest H., and Hayes J. M. (1989) Carbon isotope fractionation by thermophilic phototrophic sulphur bacteria: Evidence for autotrophic growth in natural populations. Appl. Envir. Microbiol. 55, 639-644.
27. Murphy M. T., McCormick A., and Eglinton G. (1967) Perhydro-β-carotene in the Green River Shale. Science 157, 1040-1042.
28. Ocampo R., Callot H. J., and Albrecht P. (1985) Occurrence of bacterioporphyrins in oil shale. J. Chem. Soc. Chem. Comm., 200-201.
29. Ostroukhov S. B., Arefyev O. A., Makusina V. M., Zabrodina M. N., and Petrov A. L. A. (1982) Monocyclic aromatic hydrocarbons with isoprenoid chains. Neftekhimiya 22, 723-788 (in Russian).
30. Paul J. (1982) Zur Rand und Schellen-Fazies des Kupferschiefers. Z. geol. Ges. 133, 571-605.
31. Pfennig N. (1978) General physiology and ecology of photosynthetic bacteria. In Photosynthetic Bacteria (ed. R. K Clayton and W. R Sistrom), Chap. 1, pp. 3-16. Plenum Press.
32. Poole C. F. and Zlatkis A. (1979) Trialkylsilyl ether derivatives (other than TMS) for gas chromatography and mass spectrometry. J. Chrom. Sci. 17, 115-123.
33. Püttmann W. and Eckardt C. B. (1989) Influence of an intrusion on the extent of isomerism in acyclic isoprenoids in the Permian Kupferschiefer of the Lower Rhine Basin, N. W. Germany. Org. Geochem. 14, 651-658.
34. Quandt L., Gottschalk G., Ziegler H., and Stichler W. (1977) Isotope discrimination by photosynthetic bacteria. FEMS Microbiol. Letts. 1, 125-128
35. Quirke J. M. E., Shaw G. J., Soper P. D., and Maxwell J. R. (1980) Petroporphyrins-II. The presence of porphyrins with extended alkyl substituents. Tetrahedron 36, 3261-3267.
36. Repeta D. J. (1993) A high resolution historical record of Holocene anoxygenic primary production in the Black Sea. Geochim. Cosmochim. Acta. 57, 4437-4442.
37. Requejo A. G., Allan J., Creaney S., Gray N. R., and Cole K. S. (1992) Aryl isoprenoids and diaromatic carotenoids in Palaeozoic source rocks and oils from the Western Canada and Williston Basins. Org. Geochem. 19, 245-264.
38. Rieber H. (1982) The formation of bituminous layers of the Middle Triassic of Ticino (Switzerland). In Cyclic and Event Stratification (ed. G. Einsele and A. Seilacher), pp. 527. Springer-Verlag.
39. Rieley G. (1994) Derivatisation of organic compounds prior to gas chromatography-combustion-isotope ratio mass spectrometric analysis: Identification of isotope fractionation processes. Analyst 199, 915-919.
40. Rontani J. F., Baillet G., and Aubert C. (1991) Production of acyclic isoprenoid compounds during the photodegradation of chlorophyll a in sea water. J. Photochem. Photobiol. A. Chem. 59, 369-377.
41. Rowland S. J. (1990) Production of acyclic isoprenoid hydrocarbons by laboratory maturation of methanogenic bacteria. Org. Geochem. 15, 9-16.
42. Schaeffer P., Ocampo R., Callot H. J., and Albrecht P. (1993) Extraction of bound porphyrins from sulphur-rich sediments and their use for reconstruction of palaeoenvironments. Nature 364, 133-136.
43. Schaeffer P., Harrison W. N., Keely B. J., and Maxwell J. R. (1995) Product distributions from chemical degradation of kerogens from a marl from a Miocene Evaporitic sequence (Vena del Gesso, N. Italy). Org. Geochem. 23, 541-554.
44. Schaeflé J., Ludwig B., Albrecht P., and Ourisson G. (1977). Hydrocarbures aromatiques d'origine geologique. II. Nouveaux carotenoides aromatiques fossiles. Tetrahedron Lett. 41, 3673-3676.
45. Schouten S., Sinninghe Damsté J. S., and de Leeuw J. W. (1995) Occurrence and distribution of low-molecular weight sulphoxides in polar fractions of sediment extracts and petroleum. Org. Geochem. 23, 129-138.
46. Schwark L. (1992) Geochemische Fazies-Charakterisierung des Basalen Zechsteins unter besonderer Berucksichtigung der Palaosalinitat und des Redoxpotentials. Diss., RWTH Aachen.
47. Schwark L. And Püttmann W. (1990) Aromatic hydrocarbon composition of the Permian Kupferschiefer in the Lower Rhine Basin. NW. Germany. Org. Geochem. 16, 749-761.
48. Sherman G., Korn T. M., and Linschitz H. (1972) Low-temperature photo-oxidation of chlorophyll a. Photochem. Photobiol. 16, 499-509.
49. Sinninghe Damsté J. S, Wakeham S. G., Kohnen M. E. L., Hayes J. M., and de Leeuw J. W. (1993). A 6,000-year sedimentary molecular record of chemocline excursions in the Black Sea. Nature 362, 827-829
50. 2 fixation in bacterial photosynthesis studied by the carbon isotope fractionation technique. Arch. Microbiol. 112, 35-38.
51. Smith K. M. and Bobe F. W. (1987) Light adaptation of bacteriochlorophyll-d producing bacteria by enzymic methylation of their antenna pigments. J. Chem. Soc. Chem. Comm. , 276-277.
52. Summons R. E. and Powell T. G. (1986) Chlorobiaceae in Palaeozoic seas revealed by biological markers, isotopes and geology. Nature 319, 763-765.
53. Summons R. E. and Powell T. G. (1987) Identification of arylisoprenoids in source rocks and crude oils: Biological markers for the green sulphur bacteria. Geochim. Cosmochim. Acta. 51, 557-566.
54. Troxler R. F., Smith K. M., and Brown S. B. (1980) Mechanism of photo-oxidation of bacteriochlorophyll c derivatives. Tetrahedron Lett. 21, 491-494.
55. 33 DPEP porphyrin from Boscan crude oil: Evidence for geochemical reduction of carboxylic acids. Tetrahedron Lett. 27, 5257-5260.
56. Villanueva J., Grimait J. O., De Wit R., Keely B. J., and Maxwell J. R. (1994) Sources and transformations of chlorophylls and carotenoids in a monomictic sulphate-rich karstic lake environment. Org. Geochem. 22, 739-757.
57. Volkman J. K. and Maxwell J. R. (1986) Acyclic isoprenoids as biological markers In Lacustrine and Petroleum Source Rocks (ed. A. J Fleet et al.); Geological Society Special Publication 40, 103-122.
58. Watanabe N., Yamamoto K., Ihshikawa H., and Yagi A. (1993) New chlorophyll a related compounds isolated as antioxidants from marine bivalves. J. Natl. Prods. 56, 305-317.
59. Xinke Y., Pu F., and Philp R. P. (1990) Novel biomarkers found in South Florida Basin. Org. Geochem. 15, 433-438.