Abstract
In spite of intensive studies over more than 70 years, the geochemistry of tetrapyrrole pigments still presents numerous challenges. Recent studies have focused on functionalized precursors of sedimentary porphyrins, making extensive use of developments in analytical capabilities. Many new structures have been characterized, confirming the Treibs hypothesis linking chlorophyll a to the major sedimentary porphyrin, deoxophylloerythroetioporphyrin, and revealing a number of alternative transformation pathways. Functionalized transformation products of chlorophylls a, b, and c and of bacteriochlorophylls c and d have all been recognized indicating that all primary producer communities are represented in the sedimentary record. It is evident that redox status, grazing pressure and secondary reactions can all influence the fate of chlorophyll, and that the variety of transformation products present in natural sedimentary environments contains a wealth of information pertaining to the conditions present at the time of sediment deposition. Several entirely novel pigment transformation products have been identified and others represent viable precursors for sedimentary porphyrin structures previously of uncertain origin. As a direct result of the advances in analytical methods it is now possible to perform on-line analysis at very high stratigraphic resolution. At cm and mm scale resolution pigment profiles can show a significant degree of variation, indicating that the pigments are highly sensitive markers of environmental change. Thus, in addition to providing information on the source organisms present in past environments, chlorophyll derivatives have great potential for use in a range of paleoenvironmental proxies.
Keywords
- Transformation Product
- Sedimentary Organic Matter
- Steryl Ester
- Green Sulfur Bacterium
- Oceanic Anoxic Event
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References
Airs RL and Keely BJ (2000) A novel approach for sensitivity enhancement in atmospheric pressure chemical ionization liquid chromatography/mass spectrometry of chlorophylls. Rapid Commun Mass Spectrom 14:125–128
Airs RL and Keely BJ (2002) Atmospheric pressure chemical ionisation liquid chromatography/mass spectrometry of bacteriochlorophylls from Chlorobiaceae, characteristic fragmentation. Rapid Commun Mass Spectrom 16:453–461
Airs RL and Keely BJ (2003) A high resolution study of the chlorophyll and bacteriochlorophyll pigment distributions in a calcite/gypsum microbial mat. Org Geochem 34:539–551
Airs RL, Jie C and Keely BJ (2000) A novel sedimentary chlorin: Structural evidence for a chlorophyll origin for aetioporphyrins. Org Geochem 31:1253–1256
Airs RL, Atkinson JE and Keely BJ (2001a) Development and application of a high-resolution liquid Chromatographie method forthe analysis of complex pigment distributions. J Chromatogr A 917,167–177
Airs RL, Borrego CM, Garcia-Gil J and Keely BJ (2001b) Identification of the bacteriochlorophyll homologues of Chlorobium phaeobacteroides strain UdG6053 grown at low light intensity. Photosynth Res 70, 221–230
Aydin N, Daher S and Gulaçar F (2003) On the sedimentary occurrence of chlorophyllone a. Chemosphere 52:937–942
Baker EW (1966) Mass spectrometric characterization of petroporphyrins J Am Chem Soc 88:2311–2315
Baker EW and Louda JW (1983) Thermal aspects of chlorophyll geochemistry. In: Byoroy M (ed) Advances in Organic Geochemistry 1981, pp 401–21. Wiley, Chichester
Baker EW and Louda JW (1986) Porphyrins in the geological record. In: Johns RB (ed) Biological Markers in the Sedimentary Record, Methods in Geochemistry and Geophysics, pp 125–128. Elselvier, Amsterdam
Baker EW and Palmer SE (1978) Geochemistry of porphyrins. In: Dolphin D (ed) The Porphyrins Vol 1, pp 485–551. Academic Press, London
Bonnett R, Burke PJ and Reszka A (1983) Iron porphyrins in coal. J Chem Soc Chem Commun 1085–1087
Boreham CJ, Fookes CJR, Popp BN, and Hayes JM (1989) Origins of etioporphyrins in sediments: Evidence from stable carbon isotopes. Geochim Cosmochim Acta 53:2451–2455
Burkill PH, Mantoura RFC, Llewellyn CA, and Owens NJP (1987) Microzooplankton grazing and selectivity of phytoplankton in coastal waters. Mar Biol 93:581–590
Callot HJ (1991) Geochemistry of chlorophylls. In: Scheer (ed) Chlorophylls, pp 339–364. CRC Press, Boca Raton
Callot HJ and Ocampo R (2000) Geochemistry of porphyrins. In: Kadish KM, Smith KM and Guilard R (eds) The Porphyrin Handbook Vol I, pp 350–398. Academic Press, London
Callot HJ, Ocampo R and Albrecht P (1990) Sedimentary porphyrins: Correlations with biological precursors. Energy Fuels 4:635–639
Chen NH, Bianchi TS, McKee BA and Bland JM (2001) Historical trends of hypoxia on the Louisiana shelf: Application of pigments as biomarkers. Org Geochem 32:543–561
Chen NH, Bianchi TS and Bland JM (2003) Novel decomposition products of chlorophyll-alpha in continental shelf (Louisiana shelf) sediments: Formation and transformation of carotenol chlorin esters. Geochim Cosmochim Acta 67:2027–2042
Chen N, Bianchi TS and McKee BA (2005) Early diagenesis of chloropigment biomarkers in the lower Mississippi River and Louisiana shelf: Implications for carbon cycling in a river-dominated margin. Mar Chem 93:159–177
Chicarelli MI and Maxwell JR (1984) A naturally occurring, chlorophyll b related porphyrin. Tetrahedron Lett 25:4701–4704
Chicarelli MI and Maxwell JR (1986) A novel fossil porphyrin with a fused ring system: Evidence for water column transformation of chlorophyll? Tetrahedron Lett 27:4653–4654
Chicarelli MI, Wolff GA, Murray M and Maxwell JR (1984) Porphyrins with a novel exocyclic ring system in an oil shale. Tetrahedron 40:4033–4039
Chicarelli MI, Kaur S and Maxwell JR (1987) Sedimentary Porphyrins: Unexpected structures, occurrence, and possible origins. In: Filby RH and Branthaver JF (eds) Metal Complexes in Fossil Fuels: Characterisation and Processing, ACS Symposium Series, 344, pp 40–67. American Chemical Society
Chillier XFD, Gülaçar FO and Buchs A (1993) A novel sedimentary lacustrine chlorin — characterization and geochemical significance. Chemosphere 27:2103–2110
Chillier XFD, Van Berkel GJ, Gülaçar FO and Buchs A (1994) Characterization of chlorins within a natural chlorin mixture using electrospray ion-trap mass-spectrometry Org Mass Spectrom 29:672–678
Corwin AH (1960) Petroporphyrins. In: Murphree, EV (ed) Proceedings of the 5th World Petroleum Congress, pp. 119–129. Fifth World Petroleum Congress, New York
Dahl KA, Repeta DJ, Goericke R (2004) Reconstructing the phytoplankton community of the Cariaco Basin during the Younger Dryas cold event using chlorin steryl esters Paleoceanography 19: PA 1006, doi:10.1029/2003PA000907, 2004
Eckardt CB, Keely BJ and Maxwell JR (1991) Identification of chlorophyll transformation products in a lake sediment by combined liquid-chromatography mass-spectrometry. J Chromatogr 557:271–288
Eckardt CB, Pearce GES, Keely BJ, Kowalewska G, Jaffe R and Maxwell JR (1992) A widespread chlorophyll transformation pathway in the aquatic environment Org Geochem 19:217–227
Falk H, Hoornaert G, Isenring H-P and Eschenmoser A (1975) Über enolderivate der chlorophyllreihe. Darstellung von 132, 173-cyclophäophorbid-enolen. Helv Chim Acta 58:2347–2367
Filby RH and van Berkel GJ (1987) Geochemistry of metal-complexes in petroleum, source rocks, and coals—an overview. ACS Symposium Series 344:2–39
Fookes CJR (1983) Identification of a homologous series of nickel(II)-15, 17-butanoporphyrins from an oil shale. J Chem Soc Chem Commun 1474–1476
Fookes CJR (1985) The etioporphyrins of oil shale — structural evidence for their derivation from chlorophyll. J Chem Soc Chem Commun 706–708
Fookes CJR and Jeffrey SW (1989) The structure of chlorophyllc3, a novel marine photosynthetic pigment. J Chem Soc Chem Commun 1827–1828
Gibbison R, Peakman TM and Maxwell JR (1995) Novel porphyrins as molecular fossils for anoxygenic photosynthesis. Tetrahedron Lett 36:9057–9060
Goericke R, Shankle A and Repeta DJ (1999) Novel carotenol chlorin esters in marine sediments and water column particulate matter. Geochim Cosmochim Acta 63:2825–2834
Goericke R, Strom SL and Bell MA (2000) Distribution and sources of cyclic pheophorbides in the environment. Limnol Oceanogr 45:200–211
Grice K, Gibbison R, Atkinson JE, Schwark L, Eckardt CB and Maxwell JR (1996) Maleimides (1H-pyrrole-2,5-diones) as molecular indicators of anoxygenic photosynthesis in ancient water columns. Geochim Cosmochim Acta 60:3913–3924
Grice K, Schaeffer P, Schwark L, and Maxwell JR (1997) Changes in palaeoenvironmental conditions during deposition of the Permian Kupferschiefer (Lower Rhine Basin, northwest Germany) inferred from molecular and isotopic compositions of biomarker components. Org Geochem 26:677–690
Harradine PJ and Maxwell JR (1998) Pyrophaeoporphyrins c(l) and c(2): grazing products of chlorophyll c in aquatic environments. Org Geochem 28:111–117
Harradine PJ, Harris PG, Head RN, Harris RP and Maxwell JR (1996a) Steryl chlorin esters are formed by Zooplankton herbivory. Geochim Cosmochim Acta 60:2265–2270
Harradine PJ, Peakman TM and Maxwell JR (1996b) Triterpenoid chlorin esters: Water column transformation products of chlorophyll a. Tetrahedron 52:13427–13440
Harris PG, Carter JF, Head RN, Harris RP, Eglinton G and Maxwell JR (1995a) Identification of chlorophyll transformation products in zooplankton fecal pellets and marine sediment extracts by liquid-chromatography mass-spectrometry atmospheric-pressure chemical-ionization. Rapid Commun Mass Spectrom9:1177–1183
Harris PG, Pearce GES, Peakman TM and Maxwell JR (1995b) A widespread and abundant chlorophyll transformation product in aquatic environments. Org Geochem 23:183–187
Harris PG, Zhao M, Rosell-Melé A, Tiedemann R, Sarnthein M and Maxwell JR (1996) Chlorin accumulation rate as a proxy for Quaternary marine primary productivity. Nature 383:63–65
Hendry GAF, Houghton JD and Brown SB (1987) The degradation of chlorophyll—a biological enigma. New Phytol 107:255–302
Hurley JP and Watras CJ (1991) Identification of bacteriochlorophylls in lakes via reverse-phase HPLC. Limnol Oceanogr 36:307–315
Hynninen PH (1991) Chemistry of Chlorophylls: Modifications. In: Scheer H (ed) Chlorophylls, pp 145–209. CRC Press, Boca Raton
Jeffrey SW and Hallegraeff GM (1987) Chlorophyllase distribution in 10 classes of phytoplankton—a problem for chlorophyll analysis. Mar Ecol Prog Ser 35:293–304
Jie C, Walker JS and Keely BJ (2002) Atmospheric pressure chemical ionization normal phase liquid chromatography mass spectrometry and tandem mass spectrometry of chlorophyll a allomers. Rapid Commun Mass Spectrom 16:473–479
Karuso P, Bergquist PR, Buckleton JS, Cambie RC, Clark GR and Rickard CEF (1986) 132,173-cyclophaeophorbide enol, the first porphyrin isolated from a sponge. Tetrahedron Lett 27:2177–2178
Kaur S, Chicarelli MI and Maxwell JR (1986) Naturally occurring benzoporphyrins: Bacterial marker pigments? J Am Chem Soc 108:1347–1348
Keely B J and Maxwell JR (1990a) Fast atom bombardment mass spectrometric and tandem mass spectrometric studies of some functionalised tetrapyrroles derived from chlorophylls a and b. Energy Fuels 4:737–741
Keely BJ and Maxwell JR (1990b) NMR studies of sedimentary tetrapyrroles. Energy Fuels 4:716–719
Keely BJ and Maxwell JR (1993) The Mulhouse basin: Evidence from porphyrin distributions for water column anoxia during deposition of marls. Org Geochem, 20:1217–1225
Keely BJ, Prowse WG and Maxwell JR (1990) The Treibs Hypothesis: An evaluation based on structural studies. Energy Fuels 4:628–634
Keely BJ, Harris PG, Popp BN, Hayes JM, Meischner D and Maxwell JR (1994) Porphyrin and chlorin distributions in a late Pliocene lacustrine sediment. Geochim Cosmochim Acta 58:3691–3701
Keely B J, Blake SR, Schaeffer P and Maxwell JR (1995) Distributions of pigments in the organic-matter of marls from the Vena del Gesso evaporitic sequence. Org Geochem 23:527–539
King LL and Repeta DJ (1991) Novel pyrophaeophorbide steryl esters in Black Sea sediments. Geochim Cosmochim Acta 55:2067–2074
King LL and Repeta DJ (1994) Phorbin steryl esters in black-sea sediment traps and sediments—a preliminary evaluation of their paleooceanographic potential Geochim Cosmochim Acta 58:4389–4399
King LL and Wakeham SG (1996) Phorbin steryl ester formation by macrozooplankton in the Sargasso Sea. Org Geochem 24:581–585
Kozono M, Nomoto S, Mita H and Shimoyama A (2001) Detection of maleimides and their characteristics in Neogene sediments of the Shinjo basin, Japan. Geochem J 35:225–236
Kozono M, Nomoto S, Mita H, Ishiwatari R and Shimoyama A (2002) 2-Ethyl-3-methylnialeimide in Tokyo bay sediments providing the first evidence for its formation from chlorophylls in the present photic and oxygenic zone. Biosci Biotechnol Biochem 66:1844–1847
Kuronen P, Hyvarinen K and Hynninen PH (1993) High-performance liquid-chromatographic separation and isolation of the methanolic allomerization products of chlorophyll-a. J Chromatogr A 654:93–104
Larkum AWD and Kühl M (2005) Chlorophyll d: The puzzle resolved. Trends Plant Sei 10:355–357
Lewan MD (1984) Factors controlling the proportionality of vanadium to nickel in crude oils. Geochim Cosmochim Acta 48:2231–2238
Lewan MD and Maynard JB (1982) Factors controlling enrichment of vanadium and nickel in the bitumen of organic sedimentary rocks. Geochim Cosmochim Acta 46 2547–2560
Louda JW and Baker EW (1986) The biogeochemistry of chlorophyll. In: Sohn ML (ed) Organic Marine Chemistry, pp 107–125. American Chemical Society
Louda JW, Li J, Liu L, Winfree MN and Baker EW (1998) Chlorophyll a degradation during cellular senescence and death. Org Geochem 29:1233–1251
Louda JW, Loitz JW, Rudnick, DT and Baker EW (2000) Early diagenetic alteration of chlorophyll a and bacteriochlorophyll a in a contemporaneous marl ecosystem; Florida Bay. Org Geochem 31:1561–1580
Louda JW, Liu L and Baker EW (2002) Senescence-and death-related alteration of chlorophylls and carotenoids in marine phytoplankton. Org Geochem 33:1635–1653
Ma L and Dolphin D (1996) Stereoselective synthesis of new chlorophyll a related antioxidants isolated from marine organisms. J Org Chem 61:2501–2510
Mallorqui N, Arellano JB, Borrego CM and Garcia-Gil LJ (2005) Signature pigments of green sulfur bacteria in lower Pleistocene deposits from the Banyoles lacustrine area (Spain). J Paleolimnol 34:271–280
Mawson DH, Walker JS and Keely BJ (2004) Variations in the distributions of sedimentary alkyl porphyrins in the Mulhouse basin in response to changing environmental conditions. Org Geochem 35:1229–1241
May DA and Lash TD (1992) Porphyrins with exocyclic rings. 2. Synthesis of geochemically significant tetrahydrobenzoporphyrins from 4,5,6,7-tetrahydro-2H-isoindoles. J Org Chem 57:4820–4828
Merzlyak MN, Hendry GAF, Atherton NM, Zhigalova TV, Pavlov VK and Zhiteneva OV (1993) Pigment degradation, lipid peroxidation, and free radicals in leaves during autumn senescence. Biochem Moscow 58:129–135
Mühlecker W, Kräutler B, Ginsberg S and Matile P (1993) Breakdown of chlorophyll: A tetrapyrrolic chlorophyll catabolite from senescent rape leaves. Helv Chim Acta 76:2976–2980
Nara F, Tani Y, Soma Y, Soma M, Naraoka H, Watanabe T, Horiuchi K, Kawai T, Oda T and Nakamura T (2005) Response of phytoplankton productivity to climate change recorded by sedimentary photosynthetic pigments in Lake Hovsgol (Mongolia) for the last 23,000 years. Quat Int 136:71–81
Naylor CC and Keely BJ (1998) Sedimentary purpurins: Oxidative transformation products of chlorophylls. Org Geochem 28:417–22
Ocampo R and Repeta DJ (1999) Structural determination of purpurin-18 (as methyl ester) from sedimentary organic matter. Org Geochem 30:189–193
Ocampo R and Repeta DJ (2002) Isolation and structure determination of two novel C(132)-OH bacteriopheophytin a allomers from a coastal salt pond sediment. Org Geochem 33:849–854
Ocampo R and Repeta DJ (2004) 132(S)-OH methyl bacteriopheophorbide a allomer in sedimentary organic matter. Org Geochem 35:209–214
Ocampo R, Callot HJ, Albrecht P and Kinzinger JP (1984) A novel chlorophyll-c related petroporphyrin in oil-shale. Tetrahedron Lett 25:2589–2592
Ocampo R, Callot HJ and Albrecht P (1985) Occurrence of bacteriopetroporphyrins in oil shale. J Chem Soc Chem Commun 4:200–201
Ocampo R, Callot HJ and Albrecht P (1987) Evidence for porphyrins of bacterial and algal origin in oil shale. In: Filby RH and Branthaver JF (eds) Metal Complexes in Fossil Fuels; ACS Symposium Series Volume 344, pp 68–73. American Chemical Society, Washington
Ocampo R, Callot HJ, Albrecht P., Popp BN, Horowitz MR and Hayes JM (1989) Different isotopic compositions of C32 DPEP and C32 etioporphyrin III in oil-shale. Naturwiss 76:419–421
Ocampo R, Callot HJ, Albrecht P and Bauder C (1992) Porphyrins from the Messel oil shale (Eocene, Germany): Structure elucidation, geochemical, and biological significance and distribution as a function of depth. Geochim Cosmochim Acta 56:745–761
Ocampo R, Sachs JP and Repeta DJ (1999) Isolation and structure determination of the unstable 132,173-cyclopheophorbide a enol from recent sediments. Geochim Cosmochim Acta 63:3743–3749
Pancost RD, Crawford N, and Maxwell JR (2002) Molecular evidence for basin-scale photic zone euxinia n the Permian Zechstein Sea. Chem Geol 188:217–227
Pancost RD, Crawford N, Magness S, Turner A, Jenkyns HC and Maxwell JR (2004) Further evidence for the development of photic-zone euxinic conditions during Mesozoic oceanic anoxic events. J Geol Soc 161:353–364
Pearce GES, Eckardt CB, Keely BJ, Harradine PJ and Maxwell JR (1993) Characterization of naturally occurring steryl esters derived from chlorophyll a. Tetrahedron. Lett 34:2883–2886
Pearce GES, Harradine PJ, Talbot HM and Maxwell JR (1998) Sedimentary sterols and steryl chlorin esters: Distribution differences and significance. Org Geochem 28:3–10
Prowse WG and Maxwell JR (1991) High molecular weight chlorins in a lacustrine shale. Org Geochem 17:877–886
Prowse WG, Chicarelli MI, Keely BJ, Kaur S and Maxwell JR (1987) Characterisation of fossil porphyrins of the ‘di-DPEP’ type. Geochim Cosmochim Acta 51:2875–2877
Reuss N, Conley DJ and Bianchi TS (2005) Preservation conditions and the use of sediment pigments as a tool for recent ecological reconstruction in four Northern European estuaries. Mar Chem 95:283–302
Riffé-Chalard C, Verzegnassi L and Gülaçar FO (2000) A new series of steryl chlorin esters: Pheophorbide a steryl esters in an oxic surface sediment Org Geochem 31:1703–1712
Rosell-Melé A, Carter JF and Maxwell JR (1996) High-performance liquid chromatography-mass spectrometry of porphyrins by using an atmospheric pressure interface. J Am Soc Mass Spectrom 7:965–971
Rosell-Melé A, Carter JF and Maxwell JR (1999) Liquid chromatography/tandem mass spectrometry of free base alkyl porphyrins for the characterization of the macrocyclic substituents in components of complex mixtures. Rapid Commun Mass Spectrom 13:568–573
Roy S (1987) High performance liquid chromatography analysis of chloropigments. J Chromatogr A 391:19–34
Sakata K, Yamamoto K, Ishikawa H, Yagi A, Etoh H and Ina K (1990) Chlorophyllone a, a new phaeophorbide a related compound isolated from Ruditapes phillippinarum as an antioxidative compound. Tetrahedron Lett 31:1165–1168
Schaeffer P, Ocampo R, Callot HJ and Albrecht P (1993) Extraction of bound porphyrins from sulphur-rich sediments and their use for reconstruction of palaeoenvironments. Nature 364:133–136
Schoch S, Scheer H, Schiff JA, Rüdiger W and Siegelman HW (1981) Pyrophaeophytin a accompanies phaeophytin a in darkened light grown cells of Euglena. Z Naturforsch 36c:827–833
Shimoyama A, Kozono M, Mita H and Nomoto S (2001) Maleimides in the Cretaceous/Tertiary boundary sediments at Kawaruppu, Hokkaido, Japan. Geochem J 35:365–375
Shuman FR and Lorenzen CJ (1975) Quantitative degradation of chlorophyll a by a marine herbivore. Limnol Oceanogr 20:580–586
Soma Y, Rob N, Itoh N, Tani Y and Soma M (2005) Sterol composition of steryl chlorin esters (SCEs) formed through grazing of algae by freshwater crustaceans: Relevance to the composition of sedimentary SCEs. Limnol 6:45–51
Spooner N, Keely BJ and Maxwell JR (1994a) Biologically mediated defunctionalisation of chlorophyll in the aquatic environment-I. Senescence/decay ofthe diatom Phaeodactylum tricornutum. Org Geochem 21:509–516
Spooner N, Harvey HR, Pearce GES, Eckardt CB and MaxwellJR (1994b) Biological defunctionalisation of chlorophyll in the aquatic environment. 2. Action of endogenous algal enzymes and aerobic-bacteria. Org Geochem. 22:773–780
Spooner N, Getliff JM, Teece MA, Parkes RJ, Leftley JW, Harris PG and Maxwell JR (1995) Formation of mesopyrophaeophorbide a during anaerobic bacterial-degradation of the marine prymnesiophyte Emiliania-huxleyi Org Geochem. 22:225–229
Squier AH, Hodgson, DA and Keely BJ (2002) Sedimentary pigments as markers for environmental change in an Antarctic lake. Org Geochem 33:1655–1665
Squier AH, Hodgson DA and Keely BJ (2003) Identification of novel sulfur-containing derivatives of chlorophyll a in a Recent sediment. Chem Commun:624–625
Squier AH, Hodgson DA and Keely BJ (2004a) Structures and profiles of novel sulfur-linked chlorophyll derivatives in an Antarctic lake sediment. Org Geochem 35:1309–1318
Squier AH, Hodgson DA and Keely BJ (2004b) Identification of bacteriophaeophytin a esterified with geranylgeraniol in an Antarctic lake sediment. Org Geochem 35:203–207
Squier AH, Hodgson DA and Keely BJ (2004c) A critical assessment of the analysis and distributions of scytonemin and related UV-screening pigments in sediments. Org Geochem 35:1221–1228
Squier AH Hodgson DA and Keely BJ (2005) Evidence of late Quaternary environmental change in a continental east Antarctic lake from lacustrine sedimentary pigment distributions. Ant Sci 17:361–376
Talbot HM, Head RN, Harris RP and Maxwell JR (1999a) Distribution and stability of steryl chlorin esters in copepod faecal pellets from diatom grazing. Org Geochem 30:1163–1174
Talbot HM, Head RN, Harris RP and Maxwell JR (1999b) Steryl esters of pyropheophorbide b: A sedimentary sink for chlorophyll b. Org Geochem 30:1403–1410
Talbot HM, Head RN, Harris RP and Maxwell JR (2000) Discrimination against 4-methyl sterol uptake during steryl chlorin ester production by copepods. Org Geochem 31:871–880
Treibs A (1934a) Über das vorkommen von chlorophyll-deri-vatenin einem Ölschiefer aus der oberen Trias. Liebigs Ann 509:103–114
Treibs A (1934b) Chlorophyll- und häminderivate in bituminösen Gesteinen, Erdölen, Erdwachsen, und Asphalten. Liebigs Ann 510:42–62
Treibs A (1936) Chlorophyll and hemin derivatives in organic materials. Angew Chemie Int Edition 49:682–686
van Gemerden H (1983) Physiological ecology of purple and green bacteria. Ann Microbiol (Inst. Pasteur) 134:73–92
Verne-Mismer J, Ocampo R, Callot HJ and Albrecht P (1987) Isolation of a series of vanadyl-tetrahydrobenzopetroporphyrins from Timhadit oil shale. Structure determination and total synthesis ofthe major constituents. J Chem Soc Chem Commun:1581–1583
Verne-Mismer J, Ocampo R, Callot HJ and Albrecht P (1988) Molecular fossils of chlorophyll-c of the 17-nor-DPEP series-structure determination, synthesis, geochemical significance. Tetrahedron Lett 29:371–374
Verne-Mismer J, Ocampo R, Callot HJ and Albrecht P (1990) New chlorophyll fossils from Moroccan oil shales — porphyrins derived from chlorophyll-c 3 or a related pigment. Tetrahedron Lett 31:1751–1754
Verzegnassi L, Riffé-Chalard C, Kloeti W and Gülaçar FO (1999) Analysis of tetrapyrrolic pigments and derivatives in sediments by high performance liquid chromatography atmospheric pressure chemical ionization mass spectrometry. Fresenius J Anal Chem 364:249–253
Vila X, Abella C A, Figueras JB and Hurley JP (1998) Vertical models of phototrophic bacterial distributions in the metalimnetic microbial communities of several freshwater North-American kettle lakes. FEMS Microbiol Ecol 25:287–299
Villanueva J and Hastings DW (2000) A century-scale record of the preservation of chlorophyll and its transformation products in anoxic sediments. Geochim Cosmochim Acta 64:2281–2294
Villanueva J, Grimait JO, de Wit R, Keely BJ and Maxwell JR (1994a) Chlorophyll and carotenoid pigments in solar saltern microbial mats. Geochim Cosmochim Acta 58:4703–4715
Villanueva J, Grimait JO, de Wit R, Keely BJ and Maxwell JR (1994b) Sources and transformations of chlorophylls and carotenoids in a monomictic sulphate-rich karstic lake environment. Org Geochem 22:739–757
Walker JS and Keely BJ (2004) Distribution and significance of chlorophyll derivatives and oxidation products during the spring phytoplankton bloom in the Celtic Sea April 2002. Org Geochem 35:1289–1298
Walker JS, Squier AH, Hodgson DA and Keely BJ (2002) Origin and significance of 132-hydroxychlorophyll derivatives in sediments. Org Geochem 33:1667–1674
Walker JS, Jie C and Keely BJ (2003) Identification of diastereomeric chlorophyll allomers by atmospheric pressure chemical ionisation liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 17:1125–1131
Watanabe N, Yamamoto K, Ihshikawa H, Yagi A, Sakata K, Brinen LS and Clardy J (1993) New chlorophyll a related compounds isolated as antioxidants from marine bivalves. J Nat Prod Lloydia 56:305–317
Willstätter R and Stall A (1913) Untersuchungen Über Chloro phyll. Methoden und Ergebnisse, pp 29–147. Julius Springer-Verlag, Berlin
Wilson MA, Md Saleh SR, Hodgson DA and Keely BJ (2003) Atmospheric pressure chemical ionisation liquid chromatography/multistage mass spectrometry of isobaric bacteriopha-eophorbide d methyl esters. Rapid Commun Mass Spectrom 17:2455–2458
Wilson MA, Hodgson DA and Keely BJ (2004a) Structural variations in derivatives of the bacteriochlorophylls of Chloro-biaceae: Impact of stratigraphie resolution on depth profiles as revealed by methanolysis. Org Geochem 35:1309–1318
Wilson MA, Airs RL, Atkinson JE and Keely B J (2004b) Bacterio-viridins: Novel sedimentary chlorins providing evidence for oxidative processes affecting palaeobacterial communities. Org Geochem, 35:199–202
Wilson MA, Hodgson DA and Keely BJ (2005) Atmospheric pressure chemical ionisation-liquid chromatography/multistage mass spectrometry for assignment of sedimentary bacterio-chlorophyll derivatives. Rapid Commun Mass Spectrom 36:38–46
Wolff GA, Murray M, Maxwell JR, Hunter BK and Sanders JKM (1983) 15, 17-Butano-3,8-diethyl-2,7,12,18-tetrametyl-porphyrin — a novel naturally occurring tetrapyrrole. J Chem Soc Chem Commun:922–924
Woolley PS, Moir AJ, Hester RE and Keely BJ (1998) A comparative study of the allomerization reaction of chlorophyll a and bacteriochlorophyll a. J Chem Soc Perkin Trans 2:1833–1839
Wright SW, Jeffrey SW, Mantoura RFC, Llewellyn CA, Bjornland T, Repeta D and Welschmeyer N (1991) Improved HPLC method for the analysis of chlorophylls and carotenoids from marine-phytoplankton. Mar Ecol Prog Ser 77:183–196
Yamamoto K, Sakata K, Watanabe N, Yagi A, Brinen LS and Clardy J (1992) Chlorophyllonic acid methyl ester, a new chlorophyll a related compound isolated as an antioxidant from short-necked clam, Ruditapes philippinarum. Tet Lett 33:2587–2588
Zapata M, Rodriguez F and Garrido JL (2000) Separation of chlorophylls and carotenoids from marine phytoplankton: A new HPLC method using a reversed phase C-8 column and pyridine-containing mobile phases. Mar Ecol Prog Ser 195:29–45
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Keely, B.J. (2006). Geochemistry of Chlorophylls. In: Grimm, B., Porra, R.J., Rüdiger, W., Scheer, H. (eds) Chlorophylls and Bacteriochlorophylls. Advances in Photosynthesis and Respiration, vol 25. Springer, Dordrecht. https://doi.org/10.1007/1-4020-4516-6_37
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DOI: https://doi.org/10.1007/1-4020-4516-6_37
Publisher Name: Springer, Dordrecht
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