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Lipids and Macromolecular Lipids of the Hydrocarbon-rich Microalga Botryococcus braunii. Chemical Structure and Biosynthesis. Geochemical and Biotechnological Importance

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Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

Botryococcus braunii Kützing is a colonial Chlorophyceae (green microalga) characterized by an unusually high production of lipids and an original organization of colonies. This species is widely distributed on all continents, in freshwater, brackish and saline lakes, reservoirs or even small pools, situated in temperate, tropical and continental zones as well (1).The ability to develop spectacular blooms on the surface of unruffled waters which consist of a floating mass of colonies rich in oil is also a conspicuous feature of B. braunii. Thus during a survey of the 4000 ha Darwin River Reservoir in Australia, Wake and Hillen (2) estimated a bloom of B. braunii at 1500 tons and assaying at 30% oil.

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References

  1. Aaronson, S., T. Berner, K. Gold, L. Kushner, N.J. Patni, A. Repak, and D. Rubin: Some observations on the green planktonic alga, Botryococcus braunii and its bloom form. J. Plankton Res. 5, 693 (1983).

    Article  Google Scholar 

  2. Wake, L.V., and W. Hillen: Study of a bloom of the oil-rich alga Botryococcus braunii in the Darwin River Reservoir. Biotechnol. Bioeng. 22, 1637 (1980).

    Article  Google Scholar 

  3. Blackburn, K.B.: A reinvestigation of the alga Botryococcus braunii Kützing. Trans. Roy. Soc. Edinburgh 58, 841 (1936).

    Google Scholar 

  4. Schnepf, E., and W. Koch: Über den Feinbau der Ölalge Botryococcus braunii Kützing (Chlorococcales). Bot. Jahrb. Syst. Pflanzengesch. Pflanzengeogr. 99, 370 (1978).

    Google Scholar 

  5. Berkaloff, C., B. Rousseau, A. Coute, E. Casadevall, P. Metzger, and C. Chirac: Variability of cell wall structure and hydrocarbon type in different strains of Botryococcus braunii. J. Phycol. 20, 377 (1984).

    Article  CAS  Google Scholar 

  6. Bertrand, C.E., and B. Renault: Pila bibractensis et le boghead d’Autun. B. Soc. Hist. Nat. Autun. 5, 160 (1892).

    Google Scholar 

  7. Zalessky, M.D.: Sur les nouvelles algues découvertes dans le sapropélogène du Lac Beloe et sur une algue sapropélogène. Rev. Gen. Bot. 38, 31 (1926).

    Google Scholar 

  8. Swain, F.M., and J.M. Gilby: Ecology and taxonomy of Ostracoda and an alga from Lake Nicaragua. Publ. Stn. Zool. Napoli 33 (Suppl.), 361 (1964).

    Google Scholar 

  9. Maxwell, J.R., A.G. Douglas, G. Eglinton, and A. Mccormick: The botryococcenes-Hydrocarbons of novel structure from the alga Botryococcus braunii Kützing. Phytochemistry 7, 2157 (1968).

    Article  CAS  Google Scholar 

  10. Brown, A.C., B.A. Knights, and E. Conway: Hydrocarbon content and its relationship to physiological state in the green alga Botryococcus braunii. Phytochemistry 8, 543 (1969).

    Article  CAS  Google Scholar 

  11. Metzger, P., C. Berkaloff, E. Casadevall, and A. Coute: Alkadiene-and botryococcene-producing races of wild strains of Botryococcus braunii. Phytochemistry 24, 2305 (1985).

    Article  CAS  Google Scholar 

  12. Wolf, F.R., A.M. Nonomura, and J.A. Bassham. Growth and branched hydrocarbon production in a strain of Botryococcus braunii (Chlorophyta). J. Phycol. 21, 388 (1985).

    Article  CAS  Google Scholar 

  13. Wake, L.V., and L.W. Hillen: Nature and hydrocarbon content of the alga Botryococcus braunii occurring in Australian freshwater lakes. Aust. J. Mar. Freshwater Res. 32, 353 (1981).

    Article  CAS  Google Scholar 

  14. Metzger, P., E. Villarreal-Rosales, E. Casadevall, and A. Colite: Hydrocarbons, aldehydes and triacylglycerols in some strains of the A race of the green alga Botryococcus braunii. Phytochemistry 28, 2349 (1989).

    Article  CAS  Google Scholar 

  15. Knights, B.A., A.C. Brown, E. Conway, and B.S. Middleditch: Hydrocarbons from the green form of the freshwater alga Botryococcus braunii. Phytochemistry 9, 1317 (1970).

    Article  CAS  Google Scholar 

  16. Metzger, P., J. Templier, C. Largeau, and E. Casadevall: A n-alkatriene and some n-alkadienes from the A race of the green alga Botryococcus braunii. Phytochemistry 25, 1869 (1986).

    Article  CAS  Google Scholar 

  17. Metzger, P., E. Casadevall, and A. Coute: Botryococcene distribution in strains of the green alga Botryococcus braunii. Phytochemistry 27, 1383 (1988).

    Article  CAS  Google Scholar 

  18. Wolf, F.R., and E.R. Cox: Ultrastructure of active and resting colonies of Botryococcus braunii (Chlorophyceae). J. Phycol. 17, 395 (1981).

    Article  CAS  Google Scholar 

  19. Metzger, P., and E. Casadevall: Lycopadiene, a tetraterpenoid hydrocarbon from new strains of the green alga Botryococcus braunii. Tetrahedron Letters 28, 3931 (1987).

    Article  CAS  Google Scholar 

  20. Metzger, P., B. Allard, E. Casadevall, C. Berkaloff, and A. Coute: Structure and chemistry of a new chemical race of Botryococcus braunii (Chlorophyceae) that produces lycopadiene, a tetraterpenoid hydrocarbon. J. Phycol. 26, 258 (1990).

    Article  CAS  Google Scholar 

  21. Largeau, C., E. Casadevall, C. Berkaloff, and P. Dhamelincourt: Sites of accumulation and composition of hydrocarbons in Botryococcus braunii. Phytochemistry 19, 1043 (1980).

    Article  CAS  Google Scholar 

  22. Largeau, C., E. Casadevall, and C. Berkaloff: The biosynthesis of long-chain hydrocarbons in the green alga Botryococcus braunii. Phytochemistry 19, 1081 (1980).

    Article  CAS  Google Scholar 

  23. Metzger, P., M. David, and E. Casadevall: 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 (1987).

    Article  Google Scholar 

  24. Villarreal-Rosales, E.: Unpublished results.

    Google Scholar 

  25. Villarreal-Rosales, E. Thèse 3ème Cycle, Université de Technologie de Compiègne, 1990.

    Google Scholar 

  26. Pambou-Tchivounda, H. Unpublished results.

    Google Scholar 

  27. Templier, J., C. Largeau, and E. Casadevall: Mechanism of non-isoprenoid hydrocarbon biosynthesis in Botryococcus braunii. Phytochemistry 23, 1017 (1984).

    Article  CAS  Google Scholar 

  28. Effect of various inhibitors on biosynthesis of non-isoprenoid hydrocarbons in Botryococcus braunii. Phytochemistry 26, 377 (1987).

    Article  Google Scholar 

  29. Chan Yong, T.P., C. Largeau, and E. Casadevall: Biosynthesis of non-isoprenoid hydrocarbons by the microalga Botryococcus braunii. Evidence for an elongation-decarboxylation mechanism. Activation of decarboxylation. Nouv. J. de Chimie 10, 701 (1986).

    Google Scholar 

  30. Templier, J., C. Largeau, and E. Casadevall: Non-specific elongationdecarboxylation in biosynthesis of cis-and trans-alkadienes by Botryococcus braunii. Phytochemistry 30, 175 (1991).

    Article  CAS  Google Scholar 

  31. Cox, R.E, A.L. Burlingame, D.M. Wilson, G. Eglinton, and J.R. Maxwell: Botryococcene - a tetramethylated acyclic triterpenoid of algal origin. J. Chem. Soc. Chem. Comm. 284 (1973).

    Google Scholar 

  32. Metzger, P., E. Casadevall, M-J. Pouet, and Y. Pouet: Structures of some botryococcenes: branched hydrocarbons from the B race of the green alga Botryococcus braunii. Phytochemistry 24, 2995 (1985).

    Article  CAS  Google Scholar 

  33. Huang, Z., C.D. Poulter, F.R. Wolf, T.C. Somers, and J.D. White: Braunicene, a novel cyclic C32 isoprenoid from Botryococcus braunii. J. Am. Chem. Soc. 110, 3959 (1988).

    Article  CAS  Google Scholar 

  34. Murakami, M., H. Nakano, K. Yamaguchi, S. Konosu, O. Nakayama, Y. M.tsumoto, and H. Iwamoro: Meijicoccene, a new cyclic hydrocarbon from Botryococcus braunii. Phytochemistry 27, 455 (1988).

    CAS  Google Scholar 

  35. Douglas, A.G., K. Douraghi-Zadeh, and G. Eglinton: The fatty acids of the alga Botryococcus braunii. Phytochemistry 8, 285 (1969).

    Article  CAS  Google Scholar 

  36. Dubreuil, C., S. Derenne, C. Largeau, C. Berkaloffand B. Rousseau: Mechanism of formation and chemical structure of Coorongite. Role of the resistant biopolymer and of the hydrocarbons of Botryococcus braunii. Ultrastructure of Coorongite and its relationship with Torbanite. Org. Geochem. 14, 543 (1989).

    Article  CAS  Google Scholar 

  37. Huang, Z., and C.D. Poulter: Isoshowacene, a C31 hydrocarbon from Botryococcus braunii var. Showa. Phytochemistry 28, 3043 (1989).

    Article  CAS  Google Scholar 

  38. White, J.D., T.C. Somers, and G.N. Reddy: Absolute configuration of Botryococcene. J. Am. Chem. Soc. 108, 5352 (1986).

    Article  CAS  Google Scholar 

  39. Galbraith, M.N., L.W. Hillen, and L.V. Wake: Darwinene: a branched hydrocarbon from a green form of Botryococcus braunii. Phytochemistry 22, 1441 (1983).

    Article  CAS  Google Scholar 

  40. Stoilov, I.L., J.E. Thompson, J-H. Cho, and C. Djerassi: Biosynthetic studies of marine lipids. Stereochemical aspects and hydrogen migrations in the biosynthesis of the triply alkylated side chain of the sponge sterol strongylosterol. J. Am. Chem. Soc. 108, 8235 (1986).

    Article  CAS  Google Scholar 

  41. David, M., P. Metzger, and E. Casadevall: Two cyclobotryococcenes from the B race of the green alga Botryococcus braunii. Phytochemistry 27, 2863 (1988).

    Article  CAS  Google Scholar 

  42. Jaenicke, L., and F.-J. Marner: The irones and their precursors. In: Progress in the Chemistry of Organic Natural Products, vol. 50, ed. by W. Herz, H. Grisebach, G.W. Kirby, and C. Tamm. Wien, New York Springer. 1986.

    Google Scholar 

  43. Huang, Z., and C.D. Poulter: Braunicene. Absolute stereochemistry of the cyclohexane ring. J. Org. Chem. 53, 4089 (1988).

    Article  CAS  Google Scholar 

  44. Huang, Z., and C.D. Poulter: Isobraunicene, Wolficene, and Isowolficene. New cyclic l-3 fused isoprenoids from Botryococcus braunii. J. Org. Chem. 53, 5390 (1988).

    CAS  Google Scholar 

  45. Poulter, C.D.: Biosynthesis of non-head-to-tail terpenes. Formation of l’-1 and l’-3 linkages. Acc. Chem. Res. 23, 70 (1990).

    Article  CAS  Google Scholar 

  46. Huang, Z., and C.D. Poulter: Stereochemical studies of botryococcene biosynthesis: analogies between l’-1 and l’-3 condensations in the isoprenoid pathway. J. Am. Chem. Soc. 111, 2713 (1989).

    Article  CAS  Google Scholar 

  47. Casadevall, E., P. Metzger, and M.-P. Puech: Biosynthesis of triterpenoid hydrocarbons in the alga Botryococcus braunii. Tetrahedron Letters 25, 4123 (1984).

    Article  CAS  Google Scholar 

  48. Wolf, F.R., E.K. Nemethy, J.H. Blanding, and J.A. Bassham: Biosynthesis of unusual acyclic isoprenoids in the alga Botryococcus braunii. Phytochemistry 24, 733 (1985).

    Article  CAS  Google Scholar 

  49. Zundel, M., and M. Rohmer: Procaryotic triterpenoid. 3. The biosynthesis of 213methylhopanoids and 3ß-methylhopanoids of Methylobacterium organophilum and Acetobacter pasteurianus ssp pasteurianus. Eur. J. Biochem. 150, 35 (1985).

    Article  CAS  Google Scholar 

  50. Huang, Z., and C.D. Poulter: Tetramethylsqualene, a triterpene from Botryococcus braunii var. Showa. Phytochemistry 28, 1467 (1989).

    Article  CAS  Google Scholar 

  51. Metzger, P., and E. Casadevall: Structure de trois nouveaux botryococcenes synthétisés par une souche de Botryococcus braunii cultivée en laboratoire. Tetrahedron Letters 24, 4013 (1983).

    Article  CAS  Google Scholar 

  52. White, J.D., G.N. Reddy, and G.O. Spessard: Total synthesis of (-)-Botryococcene, J. Am. Chem. Soc. 110, 1624 (1988).

    Article  CAS  Google Scholar 

  53. Hird, N.W., T.V. Lee, A.J. Leigh, J.R. Maxwell, and T.M. Peakman: The total synthesis of 10-(R,S)-C30 botryococcene and botryococcane and a new synthesis of a general intermediate to the botryococcene family. Tetrahedron Letters 30, 4867 (1989).

    Article  CAS  Google Scholar 

  54. Grung, M., P. Metzger, and S. Liaaen-Jensen: Primary and secondary carotenoids in two races of the green alga Botryococcus braunii. Biochem. Syst. Ecol. 17, 263 (1989).

    Article  CAS  Google Scholar 

  55. Grung, M.: Unpublished results.

    Google Scholar 

  56. Metzger, P., and E. Casadevall: Aldehydes, very long chain alkenylphenols, epoxides and other lipids from an alkadiene-producing strain of Botryococcus braunii. Phytochemistry 28, 2097 (1989).

    Article  CAS  Google Scholar 

  57. Brennan, J.: Mycobacterium and other actinomycetes. In: Microbial lipids, vol. 1, ed. by C. Ratledge and S.G. Wilkinson. London: Academic Press. 1988.

    Google Scholar 

  58. Cojocaru, M., S. Droby, E. Glotter, A. Goldman, H.E. Gottlieb, B. Jacoby, and D. Prusky: 5-(12-Heptadecenyl)-resorcinol, the major component of the antifungal activity in the peel of mango fruit. Phytochemistry 25, 1093 (1986).

    Article  CAS  Google Scholar 

  59. Metzger, P., and E. Casadevall: Botryococcoid ethers. A novel type of ether lipids isolated from the green alga Botryococcus braunii. Phytochemistry, in press.

    Google Scholar 

  60. Lee, M.S., G.-W. Qin, K. Nakanishi, and M.G. Zagorski: Biosynthetic studies of brevetoxins, potent neurotoxins produced by the dinoflagellate Gymnodinium breve. J. Am. Chem. Soc. 111, 6234 (1989).

    Article  CAS  Google Scholar 

  61. Metzger, P., and E. Casadevall: In preparation.

    Google Scholar 

  62. Metzger, P., E. Villarreal-Rosales, and E. Casadevall: Methyl-branched fatty aldehydes and fatty acids in Botryococcus braunii. Phytochemistry, 30, 185 (1991).

    Article  CAS  Google Scholar 

  63. Han, J., H.W.-S. Chan, and M. Calvin: Biosynthesis of alkanes in Nostoc muscorum. J. Am. Chem. Soc. 91, 5156 (1969).

    Article  CAS  Google Scholar 

  64. Rainwater, D.L., and P.E. Kolattukudy: Fatty acid biosynthesis in Mycobacterium tuberculosis var. bonis Bacillus Calmette-Guérin. J. Biol. Chem. 260, 616 (1985).

    CAS  Google Scholar 

  65. Metzger, P., R. Bischoff, and E. Casadevall: In preparation.

    Google Scholar 

  66. Berkaloff, C., E. Casadevall, C. Largeau, P. Metzger, S. Peracca, and J. Virlet: The resistant polymer of the walls of the hydrocarbon-rich alga Botryococcus. Phytochemistry 22, 389 (1983).

    Article  CAS  Google Scholar 

  67. Largeau, C., S. Derenne, E. Casadevall, A. Kadouri, and N. Sellier: Pyrolysis of immature Torbanite and of the resistant biopolymer (PRB A) isolated from extant alga Botryococcus braunii. Mechanism of formation and structure of Torbanite. Org. Geochem. 10, 1023 (1986).

    Article  CAS  Google Scholar 

  68. Largeau, C., S. Derenne, E. Casadevall, A. Kadouri, and P. Metzger: Formation of Botryococcus-derived kerogens. Comparative study of immature Torbanites and of the extant alga Botryococcus braunii. Org. Geochem. 6, 327 (1984).

    Article  CAS  Google Scholar 

  69. Laureillard, J., C. Largeau, and E. Casadevall: Oleic acid in the biosynthesis of the resistant biopolymers of Botryococcus braunii. Phytochemistry 27, 2095 (1988).

    Article  CAS  Google Scholar 

  70. Derenne, S.: In preparation.

    Google Scholar 

  71. Kadouri, A., S. Derenne, C. Largeau, E. Casadevall, and C. Berkaloff: Resistant biopolymer in the outer walls of Botryococcus braunii, B race. Phytochemistry 27, 551 (1988).

    Article  CAS  Google Scholar 

  72. Laureillard, J., C. Largeau, F. Waeghemaeker, and E. Casadevall: Biosynthesis of the resistant polymer in the alga Botryococcus braunii. Studies on the possible direct precursors. Journal of Natural Products 49, 794 (1986).

    Article  CAS  Google Scholar 

  73. Derenne, S., C. Largeau, E. Casadevall, and C. Berkaloff: Occurrence of a resistant biopolymer in the L race of Botryococcus braunii. Phytochemistry 28, 1137 (1989).

    Article  CAS  Google Scholar 

  74. Derenne, S., C. Largeau, E. Casadevall, and N. Sellier: Direct relationship between the resistant biopolymer and the tetraterpenic hydrocarbon in the lycopadiene race of Botryococcus braunii. Phytochemistry 29, 2187 (1990).

    Article  CAS  Google Scholar 

  75. Derenne, S., C. Largeau, and E. Casadevall: Occurrence of tightly bound isoprenoid acids in an algal, resistant biomacromolecule: possible geochemical implications. Org. Geochem. in press.

    Google Scholar 

  76. Durand, B.: Sedimentary organic matter and kerogen. Definition and quantitative importance of kerogen. In: Kerogen, ed. by B. Durand. Paris: Editions Technip. 1980.

    Google Scholar 

  77. Tissot, B.P., and D.H. Welte: Kerogen, composition and classification. In: Petroleum formation and occurrence, ed. by B.P. Tissot and D.H. Welte. Berlin Heidelberg New York: Springer. 1978.

    Google Scholar 

  78. Temperley, B.N.: The Boghead controversy and the morphology of the Boghead algae. Trans. R. Soc. Edinburgh 43, 855 (1936).

    Google Scholar 

  79. Correia, M., and J. Connan: Diagenèse naturelle et diagenèse artificielle de la matière organique à éléments végétaux dominants. In: Advances in Organic Geochemistry 1973, ed. by B. Tissot and F. Bienner. Paris: Editions Technip. 73 (1974).

    Google Scholar 

  80. Derenne, S., C. Largeau, E. Casadevall, and F. Laupretre: Structural analysis of two Torbanites at different evolutionary stages. Investigation of the quantitative reliability of fa determination by 13C CP/MAS n.m.r. Fuel 66, 1084 (1987).

    Article  CAS  Google Scholar 

  81. Derenne, S., C. Largeau, E. Casadevall, and J. Connan: Comparison of Torbanites of various origins and evolutionary stages. Bacterial contribution to their formation. Cause of the lack of botryococcane in bitumens. Org. Geochem. 12, 43 (1988).

    CAS  Google Scholar 

  82. Mechanism of formation and chemical structure of Coorongite. II. Structure and origin of the labile fraction. Fate of botryococcenes during early diagenesis. Org. Geochem. 13, 965 (1988).

    Google Scholar 

  83. Derenne, S., C. Largeau, E. Casadevall, E. Tegelaar, and J.W. DE Leeuw: Relationship between algal coals and resistant cell wall biopolymers of extant algae as revealed by Py-GC-MS. Fuel Process. Technol. 20, 93 (1988).

    CAS  Google Scholar 

  84. Largeau, C., P. Bertrand, P. Fourmont, S. Derenne, and E. Casadevall: Etude de trois Torbanites par microspectrofluorimétrie: contribution des différentes fractions constitutives dans la fluorescence totale; corrélations avec la structure chimique; relations avec le degré de maturation. Bull. Soc. Géol. France 8, 993 (1989).

    Google Scholar 

  85. Kister, J., M. Guiliano, C. Largeau, S. Derenne, and E. Casadevall: Character-ization of chemical structure, degree of maturation and oil potential of Torbanites (type I kerogens) by quantitative FT-i.r. spectroscopy. Fuel. 69, 1356 (1990).

    Article  CAS  Google Scholar 

  86. Nip, M., E.W. Tegelaar, H. Brinkhuis, J.W. De Leeuw, P.A. Schenck, and P.J. Holloway: Analysis of modern and fossil plant cuticles by Curie point Py-GC and Curie point Py-GC-MS: recognition of a new, highly aliphatic and resistant biopolymer. Org. Geochem. 10, 769 (1986).

    Article  CAS  Google Scholar 

  87. Chalansonnet, S., C. Largeau, E. Casadevall, C. Berkaloff, G. Peniguel, and R. Couderc: Cyanobacterial resistant biopolymers. Geochemical implications of the properties of Schizothrix sp. resistant material. Org. Geochem. 13, 1003 (1988).

    Article  CAS  Google Scholar 

  88. Zelibor, J.L., L. Romankiw, P.G. Hatcher, and R.R. Comm,: Comparative analysis of the chemical composition of mixed and pure cultures of green algae and their decomposed residues by “C-NMR spectroscopy. Appl. Environ. Microbiol. 54, 1051 (1988).

    CAS  Google Scholar 

  89. Goth, K., J.W. DE Leeuw, W. Püttmann, and E.W. Tegelaar: Origin of Messel Oil Shale Kerogen. Nature (London) 336, 759 (1988).

    Article  CAS  Google Scholar 

  90. Tegelaar, E.W., J.W. DE Leeuw, C. Largeau, S. Derenne, H.R. Schulten, R. Müller, J.J. Bon, M. Nip, and J.C.M. Sprenkels:Scope and limitation of several pyrolysis methods in the structural elucidation of a macromolecular plant constituent in the leaf cuticle of Agave Americana L. J. Anal. Appl. Pyrolysis 15, 29 (1989).

    Article  Google Scholar 

  91. Largeau, C., S. Derenne, E. Casadevall, C. Berkaloff, M. Corolleur, B. Lugardon, J.F. Raynaud, and J. Connan: Occurrence and origin of “ultra-laminar” structures in “amorphous” kerogens of various source rocks and oil shales. Org. Geochem. 16, 889 (1990).

    Article  CAS  Google Scholar 

  92. Largeau, C., S. Derenne, C. Clairay, E. Casadevall, J.F. Raynaud, B. Lugardin, C. Berkaloff, M. Corolleur, and B. Rousseau: Characterization of various kerogens by Scanning Electron Microscopy (SEM) and Transmission Electron Microscopy (TEM). Morphological relationships with resistant outer walls in extant microorganisms. In: Proceedings of the International Symposium on Organic Petrology, Zeist 1990, ed. by W.J.J. Fermont et J.W. Weegink, Geological Survey of the Netherlands, special issue, in press.

    Google Scholar 

  93. Derenne, S., C. Largeau, E. Casadevall, C. Berkaloff, and B. Rousseau: Chemical evidence of kerogen formation in source rocks and oil shales via selective preservation of thin resistant outer walls of microalgae. Origin of ultralaminae. Geochim. Cosmochim. Acta. In press.

    Google Scholar 

  94. Tegelaar, E.W., J.W. DE Leeuw, S. Derenne, and C. Largeau: A reappraisal of kerogen formation. Geochim. Cosmochim. Acta 53, 3103 (1989).

    Article  CAS  Google Scholar 

  95. De Leeuw, J.W., and C. Largeau: A review of macromolecular organic compounds that comprise living organisms and their role in kerogen, coal and petroleum formation. In Organic Geochemistry, ed. by M.H. Engel and S.A. Macko. New York: Plenum Publishing Corp. In press.

    Google Scholar 

  96. Seiffert, W.K., and J.M. Moldowan: Paleoreconstruction by biological markers. Geochim. Cosmochim. Acta 45, 783 (1981).

    Article  Google Scholar 

  97. Tullocx, A.P.: Chemistry of waxes of higher plants. In: Chemistry and biochemistry of natural waxes, ed. by P.E. KOLATTUKUDY. Amsterdam: Elsevier. 1976.

    Google Scholar 

  98. Moldowan, J.M., and W.K. Seifert: First discovery of botryococcane in petroleum. J.C.S. Chem. Commun. 19, 912 (1980).

    Google Scholar 

  99. Mckirdy, D.M., R.E. Cox, J.K. Volkman, and V.J. Howell: Botryococcane in a new class of Australian non-marine crude oils. Nature (London) 320, 57 (1986).

    Article  CAS  Google Scholar 

  100. Brassell, S.C., G. Eglinton, and F. jiamo: Biological markers compounds as indicators of the depositional history of the Maoming Oil Shale. Org. Geochem. 10, 927 (1986).

    Article  CAS  Google Scholar 

  101. Chu, S.P.: The influence of the mineral composition of the medium on the growth of planktonic algae. I. Methods and culture media. J. Ecol. 30, 284 (1942).

    Article  CAS  Google Scholar 

  102. Belcher, J.H.: Notes on the physiology of Botryococcus braunii Kützing. Arch. Mikrobiol. 61, 335 (1968).

    Article  CAS  Google Scholar 

  103. Largeau, C., E. Casadevall, and D. Dif: Renewable hydrocarbon production from the alga Botryococcus braunii. In: Energy from biomass. 1st E.C. Conference, ed. by W. PALZ, P. CHARTIER, and D.O. HALL. London: Applied Science Publishers. 1981.

    Google Scholar 

  104. Casadevall, E., D. Dif, C. Largeau, C. Gudin, D. Chaumont, and O. Desanti: Studies on batch and continuous cultures of Botryococcus braunii: hydrocarbon production in relation to physiological state, cell ultrastructure and phosphate nutrition. Biotechnol. Bioengin. 27, 286 (1985).

    Article  CAS  Google Scholar 

  105. Metzger, P., E. Casadevall, A. Coute, and Y. Pouet: Screening of wild strains of the hydrocarbon-rich alga Botryococcus braunii. Productivity and hydrocarbon nature. In: Energy from biomass. 3rd E.C. Conference, ed. by W. PALZ, J. Comm, and D.O. HALL. London: Elsevier. 1985.

    Google Scholar 

  106. Weetall, H.: Studies on the nutritional requirements of the oil-producing alga Botryococcus braunü. Appl. Biochem. Biotechnol. 11, 377 (1985).

    Article  CAS  Google Scholar 

  107. Tenaud, M., M. Ohmori, and S. Miyachi: Inorganic carbon and acetate assimilation in Botryococcus braunii (Chlorophyceae). J. Phycol. 25, 662 (1989).

    Article  CAS  Google Scholar 

  108. Iwamoto, H., and A. Suzuki: Fat synthesis in unicellular algae. Part II: Chemical composition of nitrogen deficient Chlorella cells. Bull. Agr. Chem. Soc. 19, 247 (1955).

    CAS  Google Scholar 

  109. Aaronson, S., T. Berner, and Z. Dubinsky: Microalgae as a source of chemicals and natural products. In: Algae biomass, production and use, ed. by G. Shelef and C.J. Soeder. Amsterdam: Elsevier. 1980.

    Google Scholar 

  110. Snifrin, N.S., and S.W. Chisholm: Phytoplankton lipids: Environmental influence on production and possible commercial applications. In: Algae biomass, production and use, ed. by G. Shelef and C.J. Soeder. Amsterdam: Elsevier. 1980.

    Google Scholar 

  111. Brenckmann, F., C. Largeau, E. Casadevall, and C. Berkaloff: Influence de la nutrition azotée sur la croissance et la production d’hydrocarbures de l’algue unicellulaire Botryococcus braunii. In: Energy from biomass, 3rd E.C. Conference, ed. by W. Palz, J. Coombs, and D.O. Hall. London: Elsevier. 1985.

    Google Scholar 

  112. Dubinsky, Z., T. Berner, and S. Aaronson: Potential of large-scale algal cultures for biomass and lipid production in arid lands. Biotechnol. Bioengin. Symp. N8, 51 (1978).

    Google Scholar 

  113. Brenckmann, F., C. Largeau, E. Casadevall, B. Corre, and C. Berkaloff: Influence of light intensity on hydrocarbon and total biomass production of Botryococcus braunii. Relationships with photosynthetic characteristics. In: Energy from biomass. 3rd E.C. Conference, ed. by W. Palz, J. Coombs, and D.O. Hall. London: Elsevier. 1985.

    Google Scholar 

  114. Chirac, C., E. Casadevall, C. Largeau, and P. Metzger: Influence de la souche et des bactéries associées sur la productivité en hydrocarbures de l’algue Botryococcus braunii. C.R. Acad. Sci. Paris 295 III, 671 (1982).

    Google Scholar 

  115. Chirac, C., E. Casadevall, and C. Largeau: Croissance et production d’hydrocarbures de l’algue Botryococcus braunii en cultures associées. C.R. Acad. Sci. Paris 297 III, 187 (1983).

    Google Scholar 

  116. Chirac, C., E. Casadevall, C. Largeau, and P. Metzger: Bacterial influence upon growth and hydrocarbon production of the green alga Botryococcus braunii. J. Phycol. 21, 380 (1985).

    Article  CAS  Google Scholar 

  117. Bailliez, C., C. Largeau, E. Casadevall, and C. Berkaloff: Effets de l’immobilisation en gel d’alginate sur l’algue Botryococcus braunii. C.R. Acad. Sci. Paris 296 III, 199 (1983).

    Google Scholar 

  118. Bailliez, C., C. Largeau, and E. Casadevall: Effect of immobilization on the hydrocarbon-rich alga Botryococcus braunii. In: Energy from biomass. 2nd E.C. Conference, ed. by A. Strub, P. Chartier, and G. Schleser. London: Applied Sciences Publishers. 1983.

    Google Scholar 

  119. Bailliez, C., C. Largeau, and E. Casadevall: Growth and hydrocarbon production of Botryococcus braunii immobilized in calcium alginate gel. Appl. Microbiol. Biotechnol. 23, 99 (1985).

    CAS  Google Scholar 

  120. Bailliez, C., C. Largeau, C. Berkaloff, and E. Casadevall: Immobilization of Botryococcus braunii in alginate: Influence on chlorophyll content, photosynthetic activity and degeneration during batch cultures. Appl. Microbiol. Biotechnol. 23, 361 (1986).

    Article  CAS  Google Scholar 

  121. Bailliez, C., C. Largeau, E. Casadevall, L.W. Yang, and C. Berkaloff: Photosynthesis, growth and hydrocarbon production of Botryococcus braunii immobilized by entrapment and adsorption in polyurethane foams. Appl. Microbiol. Biotechnol. 29, 141 (1988).

    CAS  Google Scholar 

  122. Frenz, J., C. Largeau, E. Casadevall, F. Kollerup, and A.J. Daugulis: Hydrocarbon recovery and biocompatibility of solvents for extractions from cultures of Botryococcus braunii. Biotechnol. Bioengin. 34, 755 (1989).

    Article  CAS  Google Scholar 

  123. Frenz, J., C. Largeau, and E. Casadevall: Hydrocarbon recovery by extraction with a biocompatible solvent from free and immobilized cultures of Botryococcus braunii. Enzyme Microb. Technol. 11, 717 (1989).

    CAS  Google Scholar 

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Authors and Affiliations

  1. Laboratoire de Chimie Bioorganique et Organique Physique, Ecole Nationale Supérieure de Chimie de Paris, CNRS, France

    P. Metzger, C. Largeau & E. Casadevall

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  1. P. Metzger
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  2. C. Largeau
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  3. E. Casadevall
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Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz

  2. Chemistry Department, The University, Glasgow, Scotland

    G. W. Kirby

  3. Institut für Organische Chemie und Biochemie, Universität Bonn, Bonn, Federal Republic of Germany

    W. Steglich

  4. Institut für Organische Chemie, Universität Basel, Basel, Switzerland

    Ch. Tamm

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Metzger, P., Largeau, C., Casadevall, E. (1991). Lipids and Macromolecular Lipids of the Hydrocarbon-rich Microalga Botryococcus braunii. Chemical Structure and Biosynthesis. Geochemical and Biotechnological Importance. In: Herz, W., Kirby, G.W., Steglich, W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 57. Springer, Vienna. https://doi.org/10.1007/978-3-7091-9119-4_1

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  • DOI: https://doi.org/10.1007/978-3-7091-9119-4_1

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