Phytol degradation products as biogeochemical tracers in aquatic environments

Organic Geochemistry

Volumn 34, Issue 1, 2003, Pages 1-35

  Rontani, Jean François ^a   Volkman, John K ^b  

^a STATION MARINE D ENDOUME   (France)

^b CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BIOGEOCHEMICAL TRACERS;

BIOSYNTHESIS; CATALYSIS; CHLOROPHYLL; FRACTIONATION; OXIDATION; PHOTODEGRADATION;

BIOMARKERS;

CHLOROPHYLL; HYDROPEROXIDE; ISOPRENOID ALCOHOL; PHYTOL;

AQUATIC ENVIRONMENT; BIOGEOCHEMISTRY; BIOMARKER; DEGRADATION; PHYTOL; TRACER;

AQUATIC ENVIRONMENT; BIODEGRADATION; CELL AGING; DIAGENESIS;

EID: 0037265526     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(02)00185-7     Document Type: Review

References (203)

1. Abele-Oeschger, D., Theede, H., 1991. Digestion of algal pigments by the common periwinkle Littorina littorea L. (Gastropoda). Journal of Experimental Marine Biology and Ecology 147, 177-184.
2. Adam, P., Philippe, E., Albrecht, P., 1998. Photochemical sulfurization of sedimentary organic matter - a widespread process occurring at early diagenesis in natural environments. Geochimica et Cosmochimica Acta 62, 265-271.
3. Adam, P., Schneckenburger, P., Schaeffer, P., Albrecht, P., 2000. Clues to early diagenetic sulfurization processes from mild chemical cleavage of labile sulfur-rich geomacromolecules. Geochimica et Cosmochimica Acta 64, 3485-3503.
4. Alvarez, H.M., Pucci, O.H., Steinbüchel, A., 1997. Lipid storage compounds in marine bacteria. Applied and Environmental Microbiology 47, 132-139.
5. Avigan, J., Blumer, M., 1968. On the origin of pristane in marine organisms. Journal of Lipid Research 9, 350-352.
6. Azevedo, D.A., Zinu, C.J.A., Aquino Neto, F.R., Simoneit, B.R.T., 2001. Possible origin of acyclic (linear and isoprenoid) and tricyclic terpane methyl ketones in a Tasmanian tasmanite bitumen. Organic Geochemistry 32, 443-448.
7. Bach, T.J., 1995. Some new aspects of isoprenoid biosynthesis in plants - a review. Lipids 30, 191-202.
8. Baker, E.W., Smith, G.D., 1974. Pleistocene changes in chlorophyll pigments. In: Tissot, B., Bienner, F. (Eds.), Advances in Organic Geochemistry 1973. Editions Technip, Paris, pp. 649-660.
9. 20 isoprenoid thiophenes in Miocene lake sediments (Nördlinger Ries, southern Germany). Aquatic Geochemistry 3, 169-190.
10. Blackburn, T.H., 1986. Microbial processes of N- and C-cycles in marine sediments. In: Megusar, F., Gantar, M. (Eds.), Perspectives in Microbial Ecology. Slovene Society for Microbiology, Ljubljana, Yugoslavia, pp. 218-224.
11. Blumer, M., Mullin, M.M., Thomas, D.W., 1963. Pristane in zooplankton. Science 140, 974.
12. Blumer, M., Mullin, M.M., Thomas, D.W., 1964. Pristane in the marine environment. Helgoländer Meeresuntersuchungen 10, 187-201.
13. Blumer, M., 1965. Organic pigments: their long-term fate. Science 149, 722-726.
14. Blumer, M., Thomas, D.W., 1965. Phytadienes in zooplankton. Science 147, 1148-1149.
15. Blumer, M., Cooper, W.J., 1967. Isoprenoid acids in recent sediments. Science 158, 1463-1464.
16. 19 di- and triolefinic hydrocarbons in marine zooplankton and fishes. Biochemistry 8, 4067-4074.
17. Boon, J.J., Rijpstra, W.I.C., de Leeuw, J.W., Schenck, P.A., 1975. Phytenic acid in sediments. Nature 258, 414-416.
18. Boon, J.J., de Leeuw, J.W., 1979. The analysis of wax esters, very long mid-chain ketones and sterol ethers isolated from Walvis Bay diatomaceous ooze. Marine Chemistry 7, 117-132.
19. Bradshaw, S.A., O'Hara, S.C.M., Corner, E.D.S., Eglinton, G., 1990a. Changes in lipids during simulated herbivorous feeding by the marine crustacean Neomysis integer. Journal of the Marine Biological Association of the United Kingdom 70, 225-243.
20. Bradshaw, S.A., O'Hara, S.C.M., Corner, E.D.S., Eglinton, G., 1990b. Dietary lipid changes during herbivory and coprophagy by the marine invertebrate Nereis diversicolor. Journal of the Marine Biological Association of the United Kingdom 70, 771-787.
21. Bradshaw, S.A., O'Hara, S.C.M., Corner, E.D.S., Eglinton, G., 1991. Effects on dietary lipids of the marine bivalve Scrobicularia plana feeding in different modes. Journal of the Marine Biological Association of the United Kingdom 71, 635-653.
22. Bradshaw, S.A., Eglinton, G., 1993. Marine invertebrate feeding and the sedimentary lipid record. In: Engel, M.H., Macko, S.A. (Eds.), Organic Geochemistry. Plenum Press, New York, pp. 225-235.
23. Brassell, S.C., Eglinton, G., Maxwell, J.R., 1983. The geochemistry of terpenoids and steroids. Biochemical Society Transactions 11, 575-586.
24. Brassell, S.C., Lewis, C.A., de Leeuw, J.W., de Lange, F., Sinninghe Damsté, J.S., 1986. Isoprenoid thiophenes: novel products of sediment diagenesis? Nature (London) 320, 160-162.
25. Brooks, P.W., Maxwell, J.R., 1974. Early stage fate of phytol in a recently-deposited lacustrine sediment. In: Tissot, B., Bienner, F. (Eds.), Advances in Organic Geochemistry 1973. Editions Technip, Paris, pp. 977-991.
26. Brooks, J.D., Gould, K., Smith, J., 1969. Isoprenoid hydrocarbons in coal and petroleum. Nature 222, 257-259.
27. Brooks, P.W., Eglinton, G., Gaskell, S.J., McHugh, D.J., Maxwell, J.R., Philp, R.P., 1977. Lipids of Recent sediments, part II. Branched and cyclic alkanes and alkanoic acids of some temperate lacustrine and sub-tropical lagoonal/tidal-flat sediments. Chemical Geology 20, 189-204.
28. 18 ketone in Recent sediments. Geochimica et Cosmochimica Acta 42, 1175-1180.
29. Buchanan, M.S., Hashimoto, T., Asakawa, Y., 1996. Phytyl esters and phaeophytins from the hornwort Megaceros flagellaris. Phytochemistry 41, 1373-1376.
30. Cantwell, S.G., Lau, E.P., Watt, D.S., Fall, R.R., 1978. Biodegradation of acyclic isoprenoids by Pseudomonas species. Journal of Bacteriology 135, 324-333.
31. Chappe, B., Albrecht, P., Michaelis, W., 1982. Polar lipids of archaebacteria in sediments and petroleums. Science 217, 65-66.
32. 13C analyses of leaf lipids from plants with differing carbon dioxide metabolisms. Organic Geochemistry 21, 619-627.
33. Corner, E.D.S., O'Hara, S.C.M., Neal, A.C., Eglinton, G., 1986. Copepod faecal pellets and the vertical flux of biolipids. In: Corner, E.D.S., O'Hara, S.C.M. (Eds.), The Biological Chemistry of Marine Copepods. Oxford University Press, Oxford, pp. 261-321.
34. Cox, R.E., Maxwell, J.R., Ackman, R.G., Hooper, S.N., 1972. The isolation of a series of acyclic isoprenoid alcohols from an ancient sediment: approaches to a study of the diagenesis and maturation of phytol. In: von Gaertner, H.R., Wehner, H. (Eds.), Advances in Organic Geochemistry 1971. Pergamon Press, Oxford, UK, pp. 263-276.
35. Cranwell, P.A., 1986. Esters of acyclic and polycyclic isoprenoid alcohols: biochemical markers in lacustrine sediments. Organic Geochemistry 10, 891-896.
36. Cranwell, P.A., 1988. Lipid geochemistry of late Pleistocene lacustrine sediments from Burland, Cheshire, UK. Chemical Geology 68, 181-197.
37. Csupor, L., 1971. Das phytol in vergilbten Blättern. Planta Medica 19, 37-41.
38. Cuny, P., Rontani, J.-F., 1999. On the widespread occurrence of 3-methylidene-7,11,15-trimethylhexadecan-1,2-diol in the marine environment: a specific isoprenoid marker of chlorophyll photodegradation. Marine Chemistry 65, 155-165.
39. Cuny, P., Romano, J.-C., Beker, B., Rontani, J.-F., 1999. Comparison of the photo-degradation rates of chlorophyll chlorin ring and phytol side chain in phytodetritus: is the phytyldiol versus phytol ratio (CPPI) a new biogeochemical index? Journal of Experimental Marine Biology and Ecology 237, 271-290.
40. Cuny, P., Marty, J.-C., Chiaverini, J., Vescovali, I., Raphel, D., Rontani, J.-F., 2002. One-year seasonal survey of the chlorophyll photodegradation process in the Northwestern Mediterranean Sea. Deep Sea Research II 49, 1987-2005.
41. 2 as main carbon source for isoprenoid biosynthesis via the mevalonate-independent methylerythritol 4-phosphate route in the marine diatoms Phaeodactylum tricornutum and Nitzschia ovalis. Phytochemistry 53, 21-28.
42. Daley, R.J., 1973. Experimental characterisation of chlorophyll diagenesis. II. Bacterial, viral and herbivore grazing effects. Archives of Hydrobiology 72, 409-439.
43. DeLong, E.F., King, L.L., Massana, R., Cittone, H., Murray, A., Schleper, C., Wakeham, S.G., 1998. Dibiphytanyl ether lipids in nonthermophilic crenarchaeotes. Applied and Environmental Microbiology 64, 1133-1138.
44. Didyk, B.M., Simoneit, B.R.T., Brassell, S.C., Eglinton, G., 1978. Organic geochemical indicators of paleoenvironmental conditions of sedimentation. Nature 272, 216-222.
45. Disch, A., Schwender, J., Müller, C., Lichtenthaler, H.K., Rohmer, M., 1998. Distribution of the mevalonate and glyceraldehyde phosphate/pyruvate pathways for isoprenoid biosynthesis in unicellular algae and the cyano-bacterium Synechocystis PCC 6714. Biochemical Journal 333, 381-388.
46. Findlay, J.A., Patil, A.D., 1984. Antibacterial constituents of the diatom Navicular delognei. Journal of Natural Products 47, 815-818.
47. Fixter, L.M., Nagi, M.N., McCormack, J.G., Fewson, C.A., 1986. Structure, distribution and function of wax esters in Acinetobacter calcoaceticus. Journal of General Microbiology 132, 3147-3157.
48. Flesch, G., Rohmer, M., 1988. Prokaryotic hopanoids: the biosynthesis of the bacteriohopane skeleton. Formation of isoprenic units from two distinct acetate pools and a novel type of carbon/carbon linkage between triterpenes and D-ribose. European Journal of Biochemistry 175, 405-411.
49. Foote, C.S., Chang, Y.C., Denny, R.W., 1970. Chemistry of singlet oxygen X. Carotenoid quenching parallels biological protections. Journal of the American Chemical Society 92, 5216-5218.
50. Foote, C.S., 1976. Photosensitized oxidation and singlet oxygen: consequences in biological systems. In: Pryor, W.A. (Ed.), Free Radicals in Biology. Academic Press, New York, pp. 85-133.
51. Foss, S., Harder, J., 1997. Microbial transformation of a tertiary allylalcohol: regioselective isomerisation of linalool to geraniol without nerol formation. FEMS Microbiology Letters 149, 71-75.
52. Fossey, J., Lefort, D., Sorba, J., 1995. Free Radicals in Organic Chemistry, pp. 1-307. Masson, Paris
53. Franzmann, P.D., Stackebrandt, E., Sanderson, K., Volkman, J.K., Cameron, D.E., Stevenson, P.L., McMeekin, T.A., Burton, H.R., 1988. Halobacterium lacusprofundi sp nov., a halophilic bacterium isolated from Deep Lake, Antarctica. Systematic and Applied Microbiology 11, 20-27.
54. Frimer, A.A., 1979. The reaction of singlet oxygen with olefins: the question of mechanism. Chemical Review 79, 359-387.
55. 20 isoprenoid thiophenes in modern sediments. Organic Geochemistry 18, 83-91.
56. Gellerman, J.L., Anderson, W.H., Schlenck, H., 1975. Synthesis and analysis of phytyl and phytenoyl wax esters. Lipids 10, 656-661.
57. Gillan, F.T., Johns, R.B., 1980. Input and early diagenesis of chlorophylls in a temperate intertidal sediment. Marine Chemistry 9, 243-253.
58. Gillan, F.T., Nichols, P.D., Johns, R.B., Bavor, H.J., 1983. Phytol degradation by marine bacteria. Applied and Environmental Microbiology 45, 1423-1428.
59. Ginger, M.L., Chance, M.L., Sadler, I.H., Goad, L.J., 2001. The biosynthetic incorporation of the intact leucine skeleton into sterol by the trypanosomatid Leishmania mexicana. Journal of Biological Chemistry 276, 11674-11682.
60. Goossens, H., de Leeuw, J.W., Schenck, P.A., Brassell, S.C., 1984. Tocopherols as likely precursors of pristane in ancient sediments and crude oils. Nature 312, 440-442.
61. de Graaf, W., Sinninghe Damsté, J.S., de Leeuw, J.W., 1992. Laboratory simulation of natural sulphurization I. Formation of monomeric and oligomeric isoprenoid polysulphides by low-temperature reactions of inorganic polysulphides with phytol and phytadienes. Geochimica et Cosmochimica Acta 56, 4321-4328.
62. Grimalt, J.O., Yruela, I., Saiz-Jimenez, C., Toja, J., de Leeuw, J.W., Albaigés, J., 1991. Sedimentary lipid biogeochemistry of a hypereutrophic alkaline lagoon. Geochimica et Cosmochimica Acta 55, 2555-2577.
63. Grossi, V., Baas, M., Schogt, N., Klein Breteler, W.C., de Leeuw, J.W., Rontani, J.-F., 1996. Formation of phytadienes in the water column: myth or reality? Organic Geochemistry 24, 833-839.
64. Grossi, V., Hirschler, A., Raphel, D., Rontani, J.-F., de Leeuw, J.W., Bertrand, J.-C., 1998. Biotransformation pathways of phytol in Recent anoxic sediments. Organic Geochemistry 29, 845-861.
65. Han, J., Calvin, M., 1969. Hydrocarbon distribution of algae and bacteria and microbial activity in sediment. Proceedings of the National Academy of Science of the United States 64, 436-443.
66. Hansen, R.P., 1980. Phytol: its metabolic products and their distribution - a review. New Zealand Journal of Science 23, 259-275.
67. Harder, J., Probian, C., 1995. Microbial degradation of monoterpenes in the absence of molecular oxygen. Applied and Environmental Microbiology 61, 3804-3808.
68. Hartgers, W.A., Lopez, J.F., Sinninghe Damsté, J.S., Reiss, C., Maxwell, J.R., Grimalt, J.O., 1997. Sulfur-binding in recent environments. II. Speciation of sulfur and iron and implications for the occurrence of organo-sulfur compounds. Geochimica et Cosmochimica Acta 61, 4769-4788.
69. Harvey, G.R., Boran, D.A., Chesal, L.A., Tokar, J.M., 1983. The structure of marine fulvic and humic acids. Marine Chemistry 12, 119-132.
70. Harvey, H.R., Fallon, R.D., Patton, J.S., 1986. The effect of organic matter and oxygen on the degradation of bacterial membrane lipids in marine sediments. Geochimica et Cosmochimica Acta 50, 795-804.
71. Harvey, H.R., Eglinton, G., O'Hara, S.C.M., Corner, E.D.S., 1987. Biotransformation and assimilation of dietary lipids by Calanus feeding on a dinoflagellate. Geochimica et Cosmochimica Acta 51, 3031-3040.
72. 7. Marine Geology 75, 137-156.
73. ten Haven, H.L., Rullkötter, J., de Leeuw, J.W., Sinninghe Damsté, J.S., 1988. Pristane/phytane ratio as environmental indicator. Nature (London) 333, 604.
74. ten Haven, H.L., Rullkötter, J., Sinninghe Damsté, J.S., de Leeuw, J.W., 1990. Distribution of organic sulfur compounds in Mesozoic and Cenozoic deep-sea sediments from the Atlantic and Pacific Oceans and the Gulf of California. In: Orr, W.L., White, C.M. (Eds.), Geochemistry of Sulfur in Fossil Fuels. American Chemical Society, USA, pp. 613-632.
75. Hawkins, A.J.S., Bayne, B.L., Mantoura, R.F.C., Llewellyn, C.A., Navarro, E., 1986. Chlorophyll degradation and absorption throughout the digestive system of the blue mussel Mytilus edulis. Journal of Experimental Marine Biology and Ecology 96, 213-223.
76. 2S as an efficient reducing agent. Extended abstract. 20th International Meeting on Organic Geochemistry, Nancy, 10-14.10.2001, Abstracts, Vol. 1, pp. 138-139.
77. Huyser, E.S., Johnson, K.L., 1968. Concerning the nature of the polar effect in hydrogen atom abstractions from alcohols, ethers and esters. Journal of Organic Chemistry 33, 3972.
78. Hylemon, P.B., Harder, J., 1999. Biotransformation of monoterpenes, bile acids and other isoprenoids in anaerobic ecosystems. FEMS Microbiology Review 22, 475-488.
79. 18 isoprenoid ketone in recent marine sediments. Nature 244, 154-155.
80. Ikan, R., Baedecker, M.J., Kaplan, I.R, 1975. Thermal alteration experiments on organic matter in recent sediments II. Isoprenoids. Geochimica et Cosmochimica Acta 39, 187-194.
81. Jeffrey, S.W., Hallegraeff, G.M., 1987. Chlorophyllase distribution in ten classes of phytoplankton: a problem for chlorophyll analysis. Marine Ecology Progress Series 35, 293-304.
82. Johns, R.B., Gillan, F.T., Volkman, J.K., 1980. Early diagenesis of phytyl esters in a contemporary temperate intertidal sediment. Geochimica et Cosmochimica Acta 44, 183-188.
83. Kates, M., Yengoyan, L.S., Sastry, P.S., 1965. A diether analog of phosphatidyl glycerophosphate in Halobacterium cutirubrum. Biochimica et Biophysica Acta 98, 252-268.
84. Kates, M., Palameta, B., Joo, C.N., Kushner, D.J., Gibbons, N.E., 1966. Aliphatic diether analogs of glyceride derived lipids, IV. The occurrence of di-O-phytanylglycerol ether containing lipids in extremely halophilic bacteria. Biochemistry 5, 4092-4099.
85. Kates, M., 1993. Membrane lipids of archaea. In: Kates, M., Kuschner, D.J., Matheson, A.T. (Eds.), The Biochemistry of Archaea (Archaebacteria). Elsevier Science Publishing, New York, pp. 261-296.
86. Kawasaki, W., Matsui, K., Akakabe, Y., Itai, N., Kajiwara, T., 1998. Volatiles from Zostera marina. Phytochemistry 47, 27-29.
87. Kenig, F., Huc, A.Y., 1990. Incorporation of sulfur into recent organic matter in a carbonate environment (Abu Dhabi, United Arab Emirates). In: Orr, W.L., White, C.M. (Eds.), Geochemistry of Sulfur in Fossil Fuels, Vol. 429. American Chemical Society Symposium Series, USA, pp. 170-185.
88. 2.6-phytadienol. Photosynthesis Research 63, 269-280.
89. Koga, Y., Nishihara, M., Morii, H., Akagawa-Matsushita, M., 1993. Ether polar lipids of methanogenic bacteria: structures, comparative aspects and biosyntheses. Microbiology Reviews 57, 164-182.
90. Kohnen, M.E.L., Sinninghe Damsté, J.S., ten Haven, H.L., de Leeuw, J.W., 1989. Early incorporation of polysulphides in sedimentary organic matter. Nature 341, 640-641.
91. Kohnen, M.E.L., Sinninghe Damsté, J.S., ten Haven, H.L., Kock-van Dalen, A.C., Schouten, S., de Leeuw, J.W., 1991a. Identification and geochemical significance of cyclic di- and trisulfides with linear and isoprenoid carbon skeletons in immature sediments. Geochimica et Cosmochimica Acta 55, 3685-3695.
92. Kohnen, M.E.L., Sinninghe Damsté, J.S., Kock-van Dalen, A.C., de Leeuw, J.W., 1991. Di- or polysulphide-bound biomarkers in sulphur-rich geomacromolecules as revealed by selective chemolysis. Geochimica et Cosmochimica Acta 55, 1375-1394.
93. Kohnen, M.E.L., Sinninghe Damsté, J.S., de Leeuw, J.W., 1991. Biases from natural sulphurization in palaeoenvironmental reconstruction based on hydrocarbon biomarker distributions. Nature 349, 775-778.
94. Kohnen, M.E.L., Schouten, S., Sinninghe Damsté, J.S., de Leeuw, J.W., Merritt, D.A., Hayes, J.M., 1992. Recognition of paleobiochemicals by a combined molecular sulfur and isotope geochemical approach. Science 256, 358-362.
95. Kohnen, M.E.L., Sinninghe Damsté, J.S., Baas, M., Kock-van Dalen, A.C., de Leeuw, J.W., 1993. Sulphur-bound steroid and phytaine carbon skeletons in geomacromolecules: implications for the mechanism of incorporation of sulphur into organic matter. Gechimica et Cosmochimica Acta 51, 2515-2528.
96. Kok, M.D., Rijpstra, W.I.C., Robertson, L., Volkman, J.K., Sinninghe Damsté, J.S., 2000. Early steroid sulfurisation in surface sediments of a permanently stratified lake (Ace Lake, Antarctica). Geochimica et Cosmochimica Acta 64, 1425-1436.
97. Koopmans, M.P., Rijpstra, W.I.C., Klapwijk, M.M., de Leeuw, J.W., Lewan, M.D., Sinninghe Damsté, J.S., 1999. A thermal and chemical degradation approach to decipher pristane and phytane precursors in sedimentary organic matter. Organic Geochemistry 30, 1089-1104.
98. Krein, E.B., Aizenshat, Z., 1994. The formation of isoprenoid sulfur compounds during diagenesis-simulated sulfur incorporation and thermal transformation. Organic Geochemistry 21, 1015-1025.
99. de Leeuw, J.W., Correia, V.A., Schenck, P.A., 1974. On the decomposition of phytol under simulated geological conditions and in the top-layer of natural sediments. In: Tissot, B., Bienner, F. (Eds.), Advances in Organic Geochemistry 1973. Editions Technip, Paris, pp. 993-1004.
100. de Leeuw, J.W., Simoneit, B.R.T., Boon, J.J., Rijpstra, W.I.C., de Lange, F., van der Leeden, J.C.W., Correia, V.A., Burlingame, A.L., Schenck, P.A., 1977a. Phytol derived compounds in the geosphere. In: Campos, R., Goñi, J. (Eds.), Advances in Organic Geochemistry 1975. Enadimsa, Madrid, pp. 61-79.
101. de Leeuw, J.W., Rijpstra, W.I.C., Boon, J.J., de Lange, F., Schenck, P.A., 1977b. The relationship between lipids from Fontinalis antipyretica, its detritus and underlying sediment: The fate of wax esters and sterol esters. In: Golterman, H.L. (Ed.), Interactions between Sediments and Freshwater. Junk, The Hague, pp. 141-147.
102. de Leeuw, J.W., Rijpstra, W.I.C., Volkman, J.K., 1983. Free, esterified and residual bound sterols in Black Sea Unit 1 sediments. Geochimica et Cosmochimica Acta 47, 455-465.
103. de Leeuw, J.W., Sinninghe Damsté, J.S., 1990. Organic sulfur compounds and other biomarkers as indicators of palaeosalinity: a critical evaluation. In: Orr, W.L., White, C.M. (Eds.), Geochemistry of Sulfur in Fossil Fuels. American Chemical Society, USA, pp. 417-443.
104. Li, M.W., Larter, S.R., Taylor, P, Jones, D.M., Bowler, B., Bjorøy, M., 1988. Plant senescence processes and free radicals. Free Radical Biology and Medicine 5, 39-49.
105. Lichtenthaler, H.K., Rohmer, M., Schwender, J., 1997. Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Physiologia Plantarum 101, 643-652.
106. Ma, L., Dolphin, D., 1999. The metabolites of dietary chlorophylls. Phytochemistry 50, 195-202.
107. McCave, I.N., 1975. Vertical flux of particles in the ocean. Deep-Sea Research 31, 329-352.
108. McKenna, E.J., Kallio, R.E., 1971. Microbial metabolism of the isoprenoid alkane pristane. Proceedings of the National Academy of Sciences of the USA 68, 1552-1554.
109. March, J., 1985. Advanced Organic Chemistry third ed. John Wiley and Sons, p. 694.
110. Marchand, D., Rontani, J.-F., 2001. Characterisation of photooxidation and autoxidation products of phytoplanktonic monounsaturated fatty acids in particulate matter and recent sediments. Organic Geochemistry 32, 287-304.
111. Merzlyak, M.N., Hendry, G.A.F., 1994. Free radical metabolism, pigment degradation and lipid peroxidation in leaves during senescence. Proceedings of the Royal Society of Edinburgh 102B, 459-471.
112. Michaelis, W., Albrecht, P., 1979. Molecular fossils of archaebacteria in kerogen. Naturwissenschaften 66, 420-422.
113. Mize, C.E., Avigan, J., Steinberg, D., Pittman, R.C., Fales, H.M., Milne, G.W.A., 1969. A major pathway for the mammalian oxidative degradation of phytanic acid. Biochimica et Biophysica Acta 176, 720-739.
114. Mouzdahir, A., 2001. Devenir Biotique et Abiotique des Hydrocarbures Insaturés Biogènes dans le Milieu Marin. PhD thesis, Université de la Méditerranée, Marseille, France.
115. Mouzdahir, A., Bakkas, S., Rontani, J.-F., 2001. Aerobic and anaerobic abiotic oxidation of squalene in the presence of hydroperoxides. Chemosphere 44, 771-777.
116. Munoz, O., Argandona, V.H., Corcuera, L.J., 1998. Chemical constituents from shoots of Hordeum vulgare infested by the aphid Schizaphis graminum. Zeitschrift für Naturforschung C-A Journal of Biosciences 53, 811-817.
117. Nelson, J.R., 1993. Rates and possible mechanism of light-dependent degradation of pigments in detritus derived from phytoplankton. Journal of Marine Research 51, 155-179.
118. Nissenbaum, A., Baedecker, M.J., Kaplan, I.R., 1972. Organic geochemistry of Dead Sea sediments. Geochimica et Cosmochimica Acta 36, 709-727.
119. Pauly, G.G., Van Vleet, E.S., 1986. Archebacterial ether lipids: natural tracers of biogeochemical processes. Organic Geochemistry 10, 859-867.
120. Platen, H., Schink, B., 1989. Anaerobic degradation of acetone and higher ketones via carboxylation by newly isolated denitrifying bacteria. Journal of General Microbiology 135, 883-891.
121. Prahl, F.G., Eglinton, G., Corner, E.D.S., O'Hara, S.C.M., 1984a. Copepod fecal pellets as a source of dihydrophytol in marine sediments. Science 224, 1235-1237.
122. Prahl, F.G., Eglinton, G., Corner, E.D.S., O'Hara, S.C.M., Forsberg, T.E.V., 1984. Changes in plant lipids during passage through the gut of Calanus. Journal of the Marine Biological Association of the United Kkingdom 64, 317-334.
123. Putschew, A., Scholz-Böttcher, B.M., Rullkötter, J., 1996. Early diagenesis of organic matter and related sulphur incorporation in surface sediments of meromictic lake Cadagno in the Swiss Alps. Organic Geochemistry 25, 379-390.
124. Radke, M., Schaeffer, R.G., Leythaeuser, D., 1980. Composition of soluble organic matter in coals: relation to rank and liptinite fluorescence. Geochimica et Cosmochimica Acta 44, 1787-1800.
125. 2 concentration on lipid composition and carbon isotope fractrionation in Emiliania huxleyi. Geochimica et Cosmochimica Acta 64, 4179-4192.
126. Risatti, J.B., Rowland, S.J., Yon, D.A., Maxwell, J.R., 1984. Stereochemical studies of acyclic isoprenoids, XII. Lipids of methanogenic bacteria and possible contributions to sediments. In: Schenck, P.A. et al. (Eds.), Advances in Organic Geochemistry 1983. Pergamon, Oxford, pp. 93-104.
127. Robertson, L., Revill, A.T., Volkman, J.K., Sikes, E.L., 1995. Organic geochemistry of Antarctic lakes and fjords. In: Grimalt, J.O., Dorronsoro, C. (Eds.), Organic Geochemistry: Developments and Applications to Energy, Climate, Environment and Human History. A.I.G.O.A, Donostia-San Sebastián, pp. 253-254.
128. Rohdich, F., Kis, K., Bacher, A., Eisenreich, W., 2001. The non-mevalonate pathway of isoprenoids: genes, enzymes and intermediates. Current Opinion in Chemical Biology 5, 535-540.
129. Rohmer, M., Knani, M., Simonin, P., Sutter, B., Sahm, H., 1993. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochemistry Journal 295, 517-524.
130. Rohmer, M., Seemann, M., Horbach, S., Bringer-Meyer, S., Sahm, H., 1996. Glyceraldehyde 3-phosphate and pyruvate as precursors of isoprenic units in an alternative non-mevalonate pathway for terpenoid biosynthesis. Journal of the American Chemical Society 118, 2564-2566.
131. Rohmer, M., 1999. The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Natural Product Reports 16, 565-574.
132. Rontani, J.-F., Giusti, G., 1987. Photosensitized oxidation of pristane in seawater: effect of photochemical reactions on tertiary carbons. Journal of Photochemistry and Photobiology A 40, 107-120.
133. Rontani, J.-F., Giral, P.J.-P., 1990. Significance of alkane photosensitized oxidation during the photochemical degradation of crude oil hydrocarbon fractions. International Journal of Environmental Analytical Chemistry 42, 61-68.
134. Rontani, J.-F., Combe, I., Giral, P.J.-P., 1990. Abiotic degradation of free phytol in the water column: a new pathway for the production of acyclic isoprenoids in the marine environment. Geochimica et Cosmochimica Acta 54, 1307-1313.
135. Rontani, J.-F., Baillet, G., Aubert, C., 1991. Production of acyclic isoprenoid compounds during the photodegradation of chlorophyll in seawater. Journal of Photochemistry and Photobiology A59, 369-377.
136. Rontani, J.-F., Giral, P.J.-P., Baillet, G., Raphel, D., 1992. "Bound" 6,10,14-trimethylpentadecan-2-one: a useful marker for photodegradation of chlorophylls with a phytol ester group in seawater. Organic Geochemistry 18, 139-142.
137. Rontani, J.-F., Acquaviva, M., 1993. The aerobic bacterial metabolism of phytol in seawater: temperature dependence of an abiotic intermediate step and its consequences. Chemosphere 26, 1513-1525.
138. Rontani, J.-F., Aubert, C., 1994. Effect of oxy-free radicals upon the phytyl chain during chlorophyll-a photodegradation. Journal of Photochemistry and Photobiology A79, 167-172.
139. Rontani, J.-F., Grossi, V., Faure, R., Aubert, C., 1994. "Bound" 3-methylidene-7,11,15-trimethylhexadecan-1,2-diol: a new isoprenoid marker for the photodegradation of chlorophyll-a in seawater. Organic Geochemistry 21, 135-142.
140. Rontani, J.-F., Grossi, V., 1995. Abiotic degradation of intact and photooxidized chlorophyll phytyl chain under simulated geological conditions. Organic Geochemistry 23, 355-366.
141. Rontani, J.-F., Beker, B., Raphel, D., Baillet, G., 1995. Photodegradation of chlorophyll phytyl chain in dead phytoplanktonic cells. Journal of Photochemistry and Photobiology 85A, 137-142.
142. Rontani, J.-F., Cuny, P., Grossi, V., 1996a. Photodegradation of chlorophyll phytyl chain in senescent leaves of higher plants. Phytochemistry 42, 347-351.
143. Rontani, J.-F., Raphel, D., Cuny, P., 1996b. Early diagenesis of the intact and photooxidized chlorophyll phytyl chain in a recent temperate sediment. Organic Geochemistry 24, 825-832.
144. Rontani, J.-F., Gilewicz, M., Michotey, V., Zheng, T.L., Bonin, P., Bertrand, J.-C., 1997. Aerobic and anaerobic metabolism of 6,10,14-trimethylpentadecan-2-one by a denitrifying bacterium newly isolated from marine sediments. Applied and Environmental Microbiology 63, 636-643.
145. Rontani, J.-F., Cuny, P., Grossi, V., 1998. Identification of a pool of lipid photoproducts in senescent phytoplanktonic cells. Organic Geochemistry 29, 1215-1225.
146. Rontani, J.-F., 1999a. Photodegradation of lipidic compounds during the senescence of phytoplankton. In: Boule, P. (Ed.), Environmental Photochemistry - The Handbook of Environmental Chemistry 2L. Springer Verlag, Berlin, pp. 263-284.
147. Rontani, J.-F., 1999b. Bacterial degradation of acyclic isoprenoid compounds in the marine environment. Recent Research Developments in Microbiology 3, 465-492.
148. Rontani, J.-F., Bonin, P., Volkman, J.K., 1999a. Production of wax esters during aerobic growth of marine bacteria on isoprenoid compounds. Applied and Environmental Microbiology 65, 221-230.
149. Rontani, J.-F., Bonin, P., Volkman, J.K., 1999b. Biodegradation of free phytol by bacterial communities isolated from marine sediments under aerobic and denitrifying conditions. Applied and Environmental Microbiology 65, 5484-5492.
150. Rontani, J.-F., Bonin, P., 2000. Aerobic bacterial metabolism of phytol in seawater: effect of particle association on an abiotic intermediate step and its biogeochemical consequences. Organic Geochemistry 31, 489-496.
151. Rontani, J.-F., Marchand, D., 2000. Photoproducts of phytoplanktonic sterols: a potential source of hydroperoxides in marine sediments? Organic Geochemistry 31, 169-180.
152. Rontani, J.-F., Perrote, S., Cuny, P., 2000. Can a high chlorophyllase activity bias the use of the phytyldiol versus phytol ratio (CPPI) for the monitoring of chlorophyll photooxidation in seawater? Organic Geochemistry 31, 91-99.
153. Rontani, J.-F., 2001. Visible light-dependent degradation of lipidic phytoplanktonic components during senescence: a review. Phytochemistry 58, 187-202.
154. Rosa Putra, S., Disch, A., Bravo, J.M., Rohmer, M., 1998. Distribution of mevalonate and glyceraldehyde 3-phosphate/pyruvate routes for isoprenoid biosynthesis in some Gram-negative bacteria and mycobacteria. FEMS Microbiology Letters 164, 169-175.
155. Rowland, S.J., 1982. Origins and Fate of Sedimentary Acyclic Isoprenoids. PhD thesis, University of Bristol, UK.
156. Rowland, S.J., 1990. Production of acyclic isoprenoid hydrocarbons by laboratory maturation of methanogenic bacteria. Organic Geochemistry 15, 9-16.
157. Rowland, S.J., Maxwell, J.R., 1990. Phytenic aldehydes in a freshwater sediment. Organic Geochemistry 15, 457-460.
158. Rowland, S.J., Rockey, C., Allihaibi, S.S., Wolff, G.A., 1993. Incorporation of sulfur into phytol derivatives during simulated early diagenesis. Organic Geochemistry 20, 1-5.
159. 20) and their occurrence in deep sea sediments. Journal of High Resolution Chromatography and Chromatography Communications 11, 633-638.
160. Rullkötter, J., Littke, R., Schaefer, R.G., 1990. Characterization of organic matter-rich lacustrine sediments of Miocene age (Nördlinger Ries, Southern Germany). In: Orr, W.L., White, C.M. (Eds.), Geochemistry of Sulfur in Fossil Fuels. American Chemical Society, Washington DC, pp. 149-169.
161. Sakata, S., Hayes, J.M., McTaggart, A.R., Evans, R.A., Leckrone, K.J., Togasaki, R.K., 1997. Carbon isotopic fractionation associated with lipid biosynthesis by a cyanobacterium: relevance for interpretation of biomarker records. Geochimica et Cosmochimica Acta 61, 5379-5389.
162. Sargent, J.R., Falk-Petersen, S., 1981. Ecological investigations on the zooplankton community in Balsfjorden, Northern Norway. Marine Biology 62, 131-137.
163. Schink, B., 1988. Principles and limits of anaerobic biodegradation: environmental and technological aspects. In: Zehnder, A.J.B. (Ed.), Biology of Anaerobic Microorganisms. John Wiley & Sons, New York, pp. 771-846.
164. Schouten, S., de Graaf, W., Sinninghe Damsté, J.S., van Driel, G.B., de Leeuw, J.W., 1994. Laboratory simulation of natural sulphurization II. Reaction of multi-functionalized lipids with inorganic polysulphides at low temperatures. Organic Geochemistry 22, 825-834.
165. Schouten, S., Klein Breteler, W.C.M., Blokker, P., Rijpstra, W.I.C., Grice, K., Baas, M., Sinninghe Damsté, J.S., 1998. Biosynthetic effects on the stable carbon isotopic compositions of algal lipids: implications for deciphering the carbon isotopic biomarker record. Geochimica et Cosmochimica Acta 62, 1397-1406.
166. Schouten, S., Rijpstra, W.I.C., Kok, M., Hopmans, E.C., Summons, R.E., Volkman, J.K., Sinninghe Damsté, J.S., 2001. Molecular organic tracers of biogeochemical processes in a saline meromictic lake (Ace Lake). Geochimica et Cosmochimica Acta 65, 1629-1640.
167. Schreiber, B.C., Philp, R.P., Benali, S., Helman, M.L., De La Pena, J.A., Marfil, R., Landais, P., Cohen, A.D., Kendall, C.G.S.C., 2001. Characterisation of organic matter formed in hypersaline carbonate/evaporite environments: hydrocarbon potential and biomarkers obtained through artificial maturation studies. Journal of Petroleum Geology 24, 309-338
168. Schulte-Elte, K.H., Muller, B.L., Pamingle, H., 1979. Photooxygenation of 3,3-dialkylsubstituted allyl alcohols. Occurrence of syn preference in the ene addition of singlet oxygen at E/Z isomeric allyl alcohols. Helvetica Chimica Acta 62, 816-828.
169. 13C-labelled phytol in sulfur-rich anaerobic lacustrine sediments. Extended abstract. 20th International Meeting on Organic Geochemistry, Nancy, Abstracts, Vol. 1, pp. 136-137.
170. Schwender, J., Zeidler, J., Gröner, R., Müller, C., Focke, M., Braun, S., Lichtenthaler, F.W., Lichtenthaler, H.K., 1997. Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae. FEBS Letters 414, 129-134.
171. Schwender, J., Gemunden, C., Lichtenthaler, H.K., 2001. Chlorophyta exclusively use the 1-deoxyxylulose 5-phosphate/2-C-methylerythritol 4-phosphate pathway for the biosynthesis of isoprenoids. Planta 212, 416-423.
172. Sever, J., Parker, P.L., 1969. Fatty alcohols (normal and isoprenoid) in sediments. Science 164, 1052-1054.
173. Shuman, F.R., Lorenzen, C.J., 1975. Quantitative degradation of chlorophyll by a marine herbivore. Limnology and Oceanography 20, 580-586.
174. Simoneit, B.R.T., 1973. Identification of isoprenoidal ketones in Deep Sea Drilling Project core samples and their geochemical significance. In: In: Burns, R.E. et al. (Eds.), Initial Reports of the Deep Sea Drilling Project, Vol.21. US Government Printing Office, Washington, DC, pp. 909-923.
175. Simoneit, B.R.T., 1977. Leg 41 sediment lipids - search for eolian organic matter in recent samples and examination of a black shale. In: Lancelot, Y. et al. (Eds.), Initial Reports of the Deep Sea Drilling Project, Vol. 41.., US Government Printing Office, Washington DC, pp. 855-858.
176. Simoneit, B.R.T., 1978. Lipid analyses of sediments from site 364 in the Angola Basin, DSDP Leg 40. In: Bolli, H.M. et al. (Eds.), Initial Reports of the Deep Sea Drilling Project, Vol. 40, supplement. US Government Printing Office, Washington DC, pp. 659-662.
177. Sinninghe Damsté, J.S., de Leeuw, J.W., Kock-van Dalen, A.C., de Zeeuw, M.A., de Lange, F., Rijpstra, W.I.C., Schenck, P.A., 1987. The occurrence and identification of series of organic sulphur compounds in oils and sediments 1. A study of Rozel Point Oil (U.S.A.). Geochimica et Cosmochimica Acta 51, 2369-2391.
178. Sinninghe Damsté, J.S., Rijpstra, W.I.C., de Leeuw, J.W., Schenck, P.A., 1988. Origin of organic sulphur compounds and sulphur-containing high molecular weight substances in sediments and immature crude oils. In: Mattavelli, L., Novelli, L. (Eds.), Advances in Organic Geochemistry 1987. Pergamon Press, Oxford, UK, pp. 593-606.
179. Sinninghe Damsté, J.S., van Koert, E.R., Kock-van Dalen, A.C., de Leeuw, J.W., Schenck, P.A., 1989. Characterisation of highly branched isoprenoid thiophenes occurring in sediments and immature crude oils. Organic Geochemistry 14, 555-567.
180. Sinninghe Damsté, J.S., Rijpstra, W.I.C., de Leeuw, J.W., Schenck, P.A., 1989. The occurrence and identification of series of organic sulphur compounds in oils and sediment extracts. II. Their presence in samples from hypersaline and non-hypersaline palaeoenvironments and possible application as source, paleoenvironmental and maturity indicators. Geochimica et Cosmochimica Acta 53, 1323-1341.
181. Sinninghe Damsté, J.S., de Leeuw, J.W., 1990. Analysis, structure and geochemical significance of organically-bound sulphur in the geosphere: state of the art and future research. In: Durand, B., Behar, F. (Eds.), Advances in Organic Geochemistry 1989. Pergamon Press, Oxford UK, pp. 1077-1101.
182. Sinninghe Damsté, J.S., Eglinton, T.I., Rijpstra, W.I.C., de Leeuw, J.W., 1990. Characterization of organically bound sulfur in high-molecular-weight, sedimentary organic matter using flash pyrolysis and Raney Ni desulphurization. In: Orr, W.L., White, C.M. (Eds.), Geochemistry of Sulfur in Fossil Fuels. American Chemical Society, Washington, pp. 486-528.
183. Skerratt, J.H., Davidson, A.D., Nichols, P.D., McMeekin, T.A., 1998. Effect of UV-B on lipid content of three Antarctic marine Phytoplankton. Phytochemistry 49, 999-1007.
184. Spooner, N., Rieley, G., Collister, J.W., Lander, M., Cranwell, P.A., Maxwell, J.R., 1994. Stable carbon isotopic correlation of individual biolipids in aquatic organisms and a lake bottom sediment. Organic Geochemistry 21, 823-827.
185. Sprott, G.D., 1992. Structures of archaebacterial membrane lipids. Journal of Bioenergetics and Biomembranes 24, 555-566.
186. Sprott, G.D., Agnew, B.J., Patel, G.B., 1997. Structural features of ether lipids in the archaeobacterial thermophiles Pyrococcus furiosus, Methanopyrus kandleri, Methanothermus fervidus, and Sulfolobus acidocaldarius. Canadian Journal of Microbiology 43, 467-476.
187. Su, K.L., Schmidt, H.H.O., 1975. Metabolism of long-chain isoprenoid alcohols - incorporation of phytol and dihydrophytol into the lipid of rat brain. Biochimica et Biophysica Acta 380, 119-126.
188. Suga, T., Aoki, T., 1974. The first naturally occurring phytyl esters and hexane soluble non-volatiles from leaves of Fatsia japonica. Phytochemistry 13, 1623-1624.
189. Sun, M.-Y., Wakeham, S.G., Aller, R.C., Lee, C., 1998. Impact of seasonal hypoxia on diagenesis of phytol and its derivatives in Long Island Sound. Marine Chemistry 62, 157-173.
190. Suwa, K., Kimura, T., Schaap, A.P., 1977. Reactivity of singlet molecular oxygen with cholesterol in a phospholipidic membrane matrix: a model for oxidative damage of membranes. Biochemistry and Biophysical Research Communications 75, 785-792.
191. Tissot, B., Califet-Debyser, Y., Deroo, G., Oudin, J.L., 1971. Origin and evolution of hydrocarbons in early Toarcian shales, Paris Basin, France. American Association of Petroleum Geologists Bulletin 55, 2177-2193.
192. Tornabene, T.G., Langworthy, T.A., 1978. Diphytanyl and dibiphytanyl glycerol ether lipids of methanogenic archaea. Science 203, 51-53.
193. 35 hopanoid in sediments. Tetrahedron Letters 25, 1183-1186.
194. van de Meent, D., Waters, W.L., de Leeuw, J.W., Schenck, P.A., 1977. Formation of artifacts in sediments upon freeze-drying. Organic Geochemistry 1, 7-9.
195. Van Vleet, E.S., Quinn, J.G., 1979. Early diagenesis of fatty acids and isoprenoid alcohols in estuarine and coastal sediments. Geochimica et Cosmochimica Acta 43, 289-303.
196. Vernet, M., Mitchell, B.G., 1990. RACER: phaeopigment photo-oxidation during the spring bloom in northern Gerlache Strait. Antarctic Journal of the United States 25, 162-164.
197. Volkman, J.K., Farrington, J.W., Gagosian, R.B., Wakeham, S.G., 1983. Lipid composition of coastal marine sediments from the Peru upwelling region. In: Bjorøy, M. et al. (Ed.), Advances in Organic Geochemistry 1981. Wiley, Chichester, pp. 228-240.
198. Volkman, J.K., Maxwell, J.R., 1986. Acyclic isoprenoids as biological markers. In: Johns, R.B. (Ed.), Biological Markers in the Sedimentary Record. Elsevier, Amsterdam, pp. 1-46.
199. Wakeham, S.G., Sinninghe Damsté, J.S., Kohnen, M.E.L., de Leeuw, J.W., 1995. Organic sulfur compounds formed during early diagenesis in Black Sea sediments. Geochimica et Cosmochimica Acta 59, 521-533.
200. Werne, J.P., Hollander, D.J., Behrens, A., Schaeffer, P., Albrecht, P., Sinninghe Damsté, J.S., 2000. Timing of early diagenetic sulfurization of organic matter: a precursor-product relationship in Holocene sediments of the anoxic Cariaco Basin, Venezuela. Geochimica et Cosmochimica Acta 64, 1741-1751.
201. Withers, N.W., Nevenzel, J.C., 1977. Phytyl esters in a marine dinoflagellate. Lipids 12, 989-993.
202. Zapata, M., Garrido, J.L., 1997. Occurrence of phytylated chlorophyll c in Isochrysis galbana and Isochrysis sp (clone T-Iso) (Prymnesiophyceae). Journal of Phycology 33, 209-214.
203. Zimmerman, H.E., English, J., 1954. The cleavage reactions of 1,3-diols. Journal of the American Chemical Society 76, 2285-2294.