Mono- and dicyclic unsaturated triterpenoid hydrocarbons in ...

892 R. de Mesmay et al. / Organic Geochemistry 39 (2008) 879–893
References
Achitouv, E., Metzger, P., Rager, M.-N., Largeau, C., 2004. C 31-C 34
methylated squalenes from a Bolivian strain of Botryococcus braunii.
Phytochemistry 65, 3159–3164.
Adam, P., Schaeffer, P., Albrecht, P., 2006. C40 monoaromatic lycopane
derivatives as indicators of the contribution of the alga Botryococcus
braunii race L to the organic matter of Messel oil shale (Eocene,
Germany). Organic Geochemistry 37, 584–596.
Barker, P., Williamson, D., Gasse, F., Gibert, E., 2003. Climatic and volcanic
forcing revealed in a 50,000-year diatom record from Lake Massoko,
Tanzania. Quaternary Research 60, 368–376.
Belt, S.T., Allard, W.G., Rintatalo, J., Johns, L.A., van Duin, A.C.T., Rowland,
S.J., 2000. Clay and acid catalysed isomerisation and cyclisation
reactions of highly branched isoprenoid (HBI) alkenes: Implications
for sedimentary reactions and distributions. Geochimica et
Cosmochimica Acta 64, 3337–3345.
Bergonzini, L., Gibert, E., Winckel, A., Merdaci, O., 2001. Water and
isotopic ( 18 O and 2 H) budget of Lake Massoko, Tanzania.
Quantification of exchange between Lake and groundwater.
Comptes Rendus de l’Academie des Sciences, Series IIA, Earth and
Planetary Science 333, 617–623.
Brassell, S.C., Eglinton, G., Fu, J.M., 1986. Biological marker compounds as
indicators of the depositional history of the Maoming oil shale.
Organic Geochemistry 10, 927–941.
David, M., Metzger, P., Casadevall, E., 1988. Two cyclobotryococcenes
from the B race of the green alga Botryococcus braunii. Phytochemistry
27, 2863–2867.
Delalande, M., Bergonzini, L., Beal, F., Garcin, Y., Majule, A., Williamson, D.,
2005. Contribution to the detection of Lake Masoko (Tanzania)
groundwater outflow: isotopic evidence ( 18 O,D). Hydrological
Sciences Journal 50, 867–880.
de Mesmay, R., Grossi, V., Williamson, D., Kajula, S., Derenne, S., 2007a.
Novel mono-, di- and tri-unsaturated very long chain (C 37 -C 43) n -
alkenes in alkenone-free lacustrine sediments (Lake Masoko,
Tanzania). Organic Geochemistry 38, 323–333.
de Mesmay, R., Grossi, V., Metzger, P., Williamson, D., Kajula, S., Derenne,
S., 2007b. Abrupt biogeochemical and environmental changes during
the last 32,000 years in a tropical lake (Lake Masoko, Tanzania)
inferred from lipid biomarkers. 23rd International Meeting on
Organic Geochemistry, Torquay, UK. Book of Abstracts, pp. 1047-
1048.
Derenne, S., Largeau, C., Hetényi, M., Brukner-Wein, A., Connan, J.,
Lugardon, B., 1997. Chemical structure of the organic matter in a
Pliocene maar-type shale: Implicated Botryococcus race strains and
formation pathways. Geochimica et Cosmochimica Acta 61, 1879–
1889.
Fuhrmann, A., Mingram, J., Lücke, A., Lu, H., Horsfield, B., Liu, J.,
Negendank, J.F.W., Schleser, G.H., Wilkes, H., 2003. Variations in
organic matter composition in sediments from Lake Huguang Maar
(Huguangyan), south China during the last 68 ka: implications for
environmental and climatic change. Organic Geochemistry 34, 1497–
1515.
Galbraith, M.N., Hillen, L.W., Wake, L.V., 1983. Darwinene: a branched
hydrocarbon from a green form of Botryococcus braunii.
Phytochemistry 22, 1441–1443.
Gao, M., Simoneit, B.R.T., Gantar, M., Jaffé, R., 2007. Occurrence and
distribution of novel botryococcene hydrocarbons in freshwater
wetlands of the Florida Everglades. Chemosphere 70, 224–236.
Garcin, Y., Williamson, D., Taieb, M., Vincens, A., Mathe, P.-E., Majule, A.,
2006a. Centennial to millennial changes in maar-lake deposition
during the last 45,000 years in tropical Southern Africa (Lake Masoko,
Tanzania). Palaeogeography, Palaeoclimatology, Palaeoecology 239,
334–354.
Garcin, Y., Vincens, A., Williamson, D., Guiot, J., Buchet, G., 2006b. Wet
phases in tropical southern Africa during the last glacial period.
Geophysical Research Letters 33, L07703.
Garcin, Y., Vincens, A., Williamson, D., Buchet, G., Guiot, J., 2007. Abrupt
resumption of the African Monsoon at the Younger Dryas-Holocene
climatic transition. Quaternary Science Reviews 26, 690–704.
Gatellier, J.-P., de Leeuw, J.W., Sinninghe Damsté, J.S., Derenne, S., Largeau,
C., Metzger, P., 1993. A comparative study of macromolecular
substances of a Coorongite and cell walls of the extant alga
Botryococcus braunii. Geochimica et Cosmochimica Acta 57, 2053–
2068.
Gibert, E., Bergonzini, L., Massault, M., Williamson, D., 2002. AMS- 14 C
chronology of 40.0 cal ka BP continuous deposits from a crater lake
(Lake Massoko, Tanzania): modern water balance and environmental
implications. Palaeogeography, Palaeoclimatology, Palaeoecology
187, 307–322.
Grice, K., Schouten, S., Nissenbaum, A., Charrach, J., Sinninghe Damsté, J.S.,
1998. A remarkable paradox: Sulfurised freshwater algal
(Botryococcus braunii) lipids in an ancient hypersaline euxinic
ecosystem. Organic Geochemistry 28, 195–216.
Hebting, Y., Schaeffer, P., Behrens, A., Adam, P., Schmitt, G.,
Schneckenburger, P., Bernasconi, S.M., Albrecht, P., 2006. Biomarker
evidence for a major preservation pathway of sedimentary organic
carbon. Science 312, 1627–1631.
Heinzen, V.E.F., Soares, M.F., Yunes, R.A., 1999. Semi-empirical topological
method for the prediction of the chromatographic retention of cisand
trans-alkene isomers and alkanes. Journal of Chromatography A
849, 495–496.
Huang, Y., Murray, M., 1995. Identification of 1,6,17,21octahydrobotryococcene
in a sediment. Journal of Chemical Society,
Chemical Communications, 335–336.
Huang, Y., Murray, M., Eglinton, G., Metzger, P., 1995. Sacredicene, a novel
monocyclic C 33 hydrocarbon from sediment of Sacred Lake, a tropical
freshwater lake, Mount Kenya. Tetrahedron Letters 36, 5973–5976.
Huang, Y., Murray, M., Metzger, P., Eglinton, G., 1996. Novel unsaturated
triterpenoid hydrocarbons from sediments of Sacred Lake, Mt Kenya,
Kenya. Tetrahedron 52, 6973–6982.
Huang, Y., Street-Perrott, F.A., Perrott, R.A., Metzger, P., Eglinton, G., 1999.
Glacial-interglacial environmental changes inferred from molecular
and compound-specific d 13 C analyses of sediments from Sacred Lake,
Mt. Kenya. Geochimica et Cosmochimica Acta 63, 1383–1404.
Huang, Z., Poulter, C.D., Wolf, F.R., Somers, T.C., White, J.D., 1988.
Braunicene. A novel cyclic C 32 isoprenoid from Botryococcus braunii.
Journal of the American Chemical Society 110, 3959–3964.
Huang, Z., Poulter, C.D., 1988. Braunicene. Absolute Stereochemistry of
the Cyclohexane Ring. Journal of Organic Chemistry 53, 4089–4094.
Huang, Z., Poulter, C.D., 1989. Stereochemical studies of botryococcene
biosynthesis: analogies between 1’-1 and 1’-3 condensations in the
isoprenoid pathway. Journal of the American Chemical Society 111,
2713–2715.
Jaffé, R., Wolf, G.A., Cabrera, A.C., Carvajal-Chitty, H., 1995. The
biogeochemistry of lipids in rivers of the Orinoco Basin. Geochimica
et Cosmochimica Acta 59, 4507–4522.
Junkes, B.S., Amboni, R.D.M.C., Heinzen, V.E.F., Yunes, R.A., 2002. Use of a
semi-empirical topological method to predict the chromatographic
retention of branched alkenes. Chromatographia 55, 75–81.
McKirdy, D.M., Cox, R.E., Volkman, J.K., Howell, V.J., 1986. Botryococcane
in a new class of Australian non-marine crude oils. Nature 320, 57–59.
Merdaci, O., 1998. Changements climatiques au cours des derniers 30,000
ans en Afrique Sud-Equatoriale (Tanzanie) par l’étude des pigments et
phénols lacustres. PhD Thesis, University Aix-Marseille III.
Metzger, P., Casadevall, E., 1987. Lycopadiene, a tetraterpenoid
hydrocarbon from new strains of the green alga Botryococcus
braunii. Tetrahedron Letters 28, 3931–3934.
Metzger, P., Largeau, C., 1999. Chemicals of Botryococcus braunii. In:
Cohen, Z. (Ed.), Chemicals from Microalgae. Taylor and Francis,
London, pp. 205–260.
Metzger, P., Berkaloff, C., Casadevall, E., Couté, A., 1985a. Alkadiene- and
botryococcene-producing races of wild strains of Botryococcus braunii.
Phytochemistry 24, 2305–2312.
Metzger, P., Casadevall, E., Pouet, M.J., Pouet, Y., 1985b. Structures of some
botryococcenes: branched hydrocarbons from the B-race of the green
alga Botryococcus braunii. Phytochemistry 24, 2995–3002.
Metzger, P., Templier, J., Largeau, C., Casadevall, E., 1986. An n -alkatriene
and some n -alkadienes from the A race of the green alga Botryococcus
braunii. Phytochemistry 25, 1869–1872.
Metzger, P., David, M., Casadevall, E., 1987. Biosynthesis of triterpenoid
hydrocarbons in the B-race of the green alga Botryococcus braunii.
Sites of production and nature of the methylating agent.
Phytochemistry 26, 129–134.
Metzger, P., Casadevall, E., Couté, A., 1988. Botryococcene distribution in
strains of the green alga Botryococcus braunii. Phytochemistry 27,
1383–1388.
Metzger, P., Rager, M.-N., Largeau, C., 2007. Polyacetals based on
polymethylsqualene diols, precursors of algaenan in Botryococcus
braunii race B. Organic Geochemistry 38, 566–581.
Moldowan, J.M., Seifert, W.K., 1980. First discovery of botryococcane in
petroleum. Journal of the Chemical Society, Chemical
Communications, 912–914.
Okada, S., Murakami, M., Yamaguchi, K., 1995. Hydrocarbon composition
of newly isolated strains of the green microalga Botryococcus braunii.
Journal of Applied Phycology 7, 555–559.