Botryococcus braunii: a rich source for hydrocarbons and related ether lipids
- P. Metzger,
- C. Largeau
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Abstract
This paper presents a review on Botryococcus braunii, a cosmopolitan green colonial microalga characterised by a considerable production of lipids, notably hydrocarbons. Strains like wild populations of this alga differ in the type of hydrocarbons they synthesise and accumulate: (1) n-alkadienes and trienes, (2) triterpenoid botryococcenes and methylated squalenes, or (3) a tetraterpenoid, lycopadiene. In addition to hydrocarbons and some classic lipids, these algae produce numerous series of characteristic ether lipids closely related to hydrocarbons. This review covers the algal biodiversity, the chemical structures and biosynthesis of hydrocarbons and ether lipids and the biotechnological studies related to hydrocarbon production.
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- Introduction
- Biodiversity of B. braunii
- Hydrocarbons
- Ether lipids and their biosynthesis
- Biotechnological studies
- Conclusions
- References
- References
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References (96)
- Aaronson S, Berner T, Gold K, Kushner L, Patni NJ, Repak A, Rubin D (1983) Some observations on the green planktonic alga, Botryococcus braunii and its bloom form. J Plankton Res 5:693–700
- Achitouv E, Metzger P, Rager M-N, Largeau C (2004) C31–C34 methylated squalenes from a Bolivian strain of Botryococcus braunii. Phytochemistry 65:3159–3165
- An J-Y, Sim S-J, Lee JS, Kim BW (2003) Hydrocarbon production from secondarily treated piggery wastewater by the green alga Botryococcus braunii. J Appl Phycol 15:185–191 CrossRef
- Baillez C, Largeau C, Casadevall E (1985) Growth and hydrocarbon production of Botryococcus braunii immobilized in calcium alginate gel. Appl Microbiol Biotechnol 23:99–105 CrossRef
- Baillez C, Largeau C, Berkaloff C, Casadevall E (1986) Immobilization of Botryococcus braunii in alginate: influence on chlorophyll content, photosynthetic activity and degeneration during batch cultures. Appl Microbiol Biotechnol 23:361–366
- Baillez C, Largeau C, Casadevall E, Yang LW, Berkaloff C (1988) Photosynthesis, growth and hydrocarbon production of Botryococcus braunii immobilized by entrapment and adsorption in polyurethane foams. Appl Microbiol Biotechnol 29:141–147 CrossRef
- Brenckmann F, Largeau C, Casadevall E, Berkaloff C (1985a) Influence de la nutrition azotée sur la croissance et la production d’hydrocarbures de l’algue Botryococcus braunii. In: Palz W, Coombs J, Hall DO (eds) Energy from biomass. Elsevier, London, pp 717–721
- Brenckmann F, Largeau C, Casadevall E, Core C, Berkaloff C (1985b) Influence of light intensity on hydrocarbon and total biomass production of Botryococcus braunii. Relationships with photosynthetic characteristics. In: Palz W, Coombs J, Hall DO (eds) Energy from biomass. Elsevier, London, pp 722–726
- Brown AC, Knights BA (1969) Hydrocarbon content and its relationship to physiological state in the green alga Botryococcus braunii. Phytochemistry 8:543–547 CrossRef
- Casadevall E, Metzger P, Puech MP (1984) Biosynthesis of triterpenoid hydrocarbons in the alga Botryococcus braunii. Tetrahedron Lett 25:4123–4126 CrossRef
- Casadevall E, Dif D, Largeau C, Gudin C, Chaumont D, Desanti O (1985) Studies on batch and continuous cultures of Botryococcus braunii: hydrocarbon production in relation to physiological state, cell structure, and phosphate nutrition. Biotechnol Bioeng 27:286–295
- Cepák V, Lukavsky J (1994) The effect of high irradiances on growth, biosynthetic activities and the ultrastructure of the green alga Botryococcus braunii strain Droop 1950/807-1. Arch Hydrobiol Suppl 101:1–17
- ChanYong T-P, Largeau C, Casadevall E (1986) Biosynthesis of non-isoprenoid hydrocarbons by the microalga Botryococcus braunii: evidence for an elongation decarboxylation mechanism; activation of decarboxylation. Nouv J Chim 10:701–707
- Chirac C, Casadevall E, Largeau C, Metzger P (1985) Bacterial influence upon growth and hydrocarbon production of the green alga Botryococcus braunii. J Phycol 21:380–387
- Cox RE, Burlingame AL, Wilson DM, Eglinton G, Maxwell JR (1973) Botryococcene—a tetramethylated acyclic triterpenoid of algal origin. JCS Chem Commun 12:284–285 CrossRef
- David M, Metzger P, Casadevall E (1988) Two cyclobotryococcenes from the B race of the green alga Botryococcus braunii. Phytochemistry 27:2863–2867 CrossRef
- Dennis MW, Kolattukudy PE (1991) Alkane biosynthesis by decarbonylation of aldehyde catalyzed by a microsomal preparation from Botryococcus braunii. Arch Biochem Biophys 287:268–275 CrossRef
- Dennis M, Kolattukudy PE (1992) A cobalt-porphirin enzyme converts a fatty aldehyde to a hydrocarbon and CO. Proc Natl Acad Sci USA 89:5306–5310
- Duvold T, Cali P, Bravo JM, Rohmer M (1997) Incorporation of 2-C-methyl-d-erythritol, a putative isoprenoid precursor in the mevalonate-independent pathway, into ubiquinone and menaquinone of Escherichia coli. Tetrahedron Lett 35:6181–6184 CrossRef
- Frenz J, Largeau C, Casadevall E (1989a) Hydrocarbon recovery by extraction with a biocompatible solvent from free and immobilized cultures of Botryococcus braunii. Enzyme Microb Technol 11:717–724 CrossRef
- Frenz J, Largeau C, Casadevall E, Kollerup F, Daugulis AJ (1989b) Hydrocarbon recovery and biocompatibility of solvents for extraction from cultures of Botryococcus braunii. Biotechnol Bioeng 34:755–762
- Galbraith MN, Hillen LW, Wake LV (1983) Darwinene: a branched hydrocarbon from a green form of Botryococcus braunii. Phytochemistry 22:1441–1443; errata (1983) Phytochemistry 22:2889 CrossRef
- Gudin C, Chaumont D (1981) For a solar biotechnology based on microalgae. In: Chartier P, Palz W (eds) Energy from biomass, serie E, vol 1. Reidel, Dordrecht, pp 81–84
- Gudin C, Chaumont D (1984) Solar biotechnology study and development of tubular solar receptors for controlled production of photosynthetic cellular biomass for methane production and specific exocellular biomass. In: Palz W, Pirrwitz D (eds) Energy from biomass, serie E, vol 5. Reidel, Dordrecht, pp 184–193
- Huang Y, Street-Perrott FA, Perrott RA, Metzger P, Eglinton G (1999) Glacial-interglacial environmental changes inferred from molecular and compound-specific δ13C analyses of sediments from Sacred lake, Mt. Kenya. Geochim Cosmochim 63:1383–1404 CrossRef
- Huang Z, Poulter CD (1988) Braunicene. Absolute stereochemistry of the cyclohexane ring. J Org Chem 53:4089–4094
- Huang Z, Poulter CD (1989a) Tetramethylsqualene, a triterpene from Botryococcus braunii var. Showa. Phytochemistry 28:1467–1470 CrossRef
- Huang Z, Poulter CD (1989b) Stereochemical studies of botryococcene biosynthesis: analogies between 1′-1 and 1′-3 condensations in isoprenoid pathway. J Am Chem Soc 111:2713–2715
- Huszar VLM, Reynolds CS (1997) Phytoplankton periodicity and sequences of dominance in an Amazonian flood-plain lake (Lago Bata, Parà, Brazil): responses to gradual environmental change. Hydrobiologia 346:169–181 CrossRef
- Inoue H, Korenaga T, Sagami H, Koyama T, Sugiyama H, Ogura K (1993) Formation of farnesal and 3-hydroxy-2,3-dihydrofarnesal from farnesol by protoplasts of Botryococcus braunii. Biochem Biophys Res Commun 196:1401–1405 CrossRef
- Inoue H, Korenaga T, Sagami H, Koyama T, Ogura K (1994a) Phosphorylation of farnesol by a cell-free system from Botryococcus braunii. Biochem Biophys Res Commun 200:1036–1041 CrossRef
- Inoue S, Dote Y, Sawayama S, Minowa T, Ogi T, Yokoyama S-Y (1994b) Analysis of oil derived from liquefaction of Botryococcus braunii. Biomass Bioenergy 6:269–274 CrossRef
- Inoue H, Sagami H, Koyama T, Ogura K (1995) Properties of farnesol phosphokinase of Botryococcus braunii. Phytochemistry 40:377–381 CrossRef
- Jarstfer MB, Zhang D-L, Poulter CD (2002) Recombinant squalene synthase. Synthesis of non-head-to-tail isoprenoids in the absence of NADPH. J Am Chem Soc 124:8834–8845 CrossRef
- Knights BA, Brown AC, Conway E, Middleditch BS (1970) Hydrocarbons from the green form of the freshwater alga Botryococcus braunii. Phytochemistry 9:1317–1324 CrossRef
- Kojima E, Zhang K (1999) Growth and hydrocarbons of microalga Botryococcus braunii in bubble column photobioreactors. J Biosci Bioeng 87:811–815 CrossRef
- Komárek J, Marvan P (1992) Morphological differences in natural populations of the genus Botryococcus (Chlorophyceae). Arch Protistendk 141:65–100
- Largeau C, Casadevall E, Berkaloff C, Dhamelincourt P (1980) Sites of accumulation and composition of hydrocarbons in Botryococcus braunii. Phytochemistry 19:1043–1051 CrossRef
- Lee SJ, Kim S-B, Kwon G-S, Yoon B-B, Oh H-M (1998) Effects of harvesting method and growth stage on the flocculation of the green alga Botryococcus braunii. Lett Appl Microbiol 27:14–18 CrossRef
- Mangold HK, Paltauf F (1983) Ether lipids, biochemical and biomedical aspects. Academic Press, New York
- McKirdy DM, Cox RE, Volkman JK, Howell VJ (1986) Botryococcane in a new class of Australian non-marine crude oils. Nature 320:57–59 CrossRef
- Mendes RL, Nobre BP, Cardoso MT, Pereira AP, Palavra AF (2003) Supercritical carbon dioxide extraction of compounds with pharmaceutical importance from microalgae. Inorg Chim Acta 356:328–334 CrossRef
- Metzger P (1993) n-Heptacosatrienes and tetraenes from a Bolivian strain of Botryococcus braunii. Phytochemistry 33:1125–1128 CrossRef
- Metzger P (1994) Phenolic ether lipids with an n-alkenylresorcinol moiety from a Bolivian strain of Botryococcus braunii (A race). Phytochemistry 36:195–212 CrossRef
- Metzger P (1999) Two terpenoid diepoxides from the green microalga Botryococcus braunii: their biomimetic conversion to tetrahydrofurans and tetrahydropyrans. Tetrahedron 55:167–176 CrossRef
- Metzger P, Casadevall E (1983) Structure de trois nouveaux botryococcènes synthétisés par une souche de Botryococcus brauniii cultivée en laboratoire. Tetrahedron Lett 24:4013–4016 CrossRef
- Metzger P, Casadevall E (1987) Lycopadiene, a tetraterpenoid hydrocarbon from new strains of the green alga Botryococcus braunii. Tetrahedron Lett 28:3931–3934 CrossRef
- Metzger P, Casadevall E (1991) Botryococcoid ethers, ether lipids from Botryococcus braunii. Phytochemistry 30:1439–1444 CrossRef
- Metzger P, Casadevall E (1992) Ether lipids from Botryococcus braunii and their biosynthesis. Phytochemistry 31:2341–2349 CrossRef
- Metzger P, Largeau C (1999) Chemicals of Botryococcus braunii. In: Cohen Z (ed) Chemicals from microalgae. Taylor & Francis, London, pp 205–260
- Metzger P, Largeau C (2002) Natural polyacetals. In: Steinbüchel A (ed) Biopolymers, vol. 9. Wiley-VCH, Weinheim, pp 113–127
- Metzger P, Rager M-N (2002) Lycopanerols H, two high molecular weight ether lipids from Botryococcus braunii comprising an α-tocopherol unit. Tetrahedron Lett 43:2377–2380 CrossRef
- Metzger P, Berkaloff C, Couté A, Casadevall E (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 CrossRef
- 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 CrossRef
- Metzger P, David M, Casadevall E (1987) Biosynthesis of triterpenoid hydrocarbons in the B race of the green alga Botryococcus brauniii. Sites of production and nature of the methylating agent. Phytochemistry 26:129–134 CrossRef
- Metzger P, Allard B, Casadevall E, Berkaloff C, Couté A (1990) Structure and chemistry of a new chemical race of Botryococcus braunii that produces lycopadiene, a tetraterpenoid hydrocarbon. J Phycol 26:258–266 CrossRef
- Metzger P, Largeau C, Casadevall E (1991) Lipids and macromolecular lipids of the hydrocarbon-rich microalga Botryococcus braunii. Prog Chem Org Nat Prod 57:1–70
- Metzger P, Pouet Y, Summons R (1997) Chemotaxonomic evidence for the similarity between Botryococcus braunii L race and Botryococcus neglectus. Phytochemistry 44:1071–1075 CrossRef
- Metzger P, Rager M-N, Largeau C (2002) Botryolins A and B, two tetramethylsqualene triethers from the green microalga Botryococcus braunii. Phytochemistry 59:839–843 CrossRef
- Metzger P, Rager M-N, Sellier N, Largeau C (2003) Lycopanerols I-L: four new tetraterpenoid ethers from the green microalga Botryococcus braunii. J Nat Prod 66:772–778
- Moldowan JM, Seifert WK (1980) First discovery of botryococcane in petroleum. JCS Chem Commun 19:912–914 CrossRef
- Ohmori M, Wolf FR, Bassham JA (1984) Botryococcus braunii carbon/nitrogen metabolism as affected by ammonia addition. Arch Microbiol 140:101–106 CrossRef
- Okada S, Murakami M, Yamaguchi K (1995) Hydrocarbon composition of newly isolated strains of the green microalga Botryococcus braunii. J Appl Phycol 7:555–559
- Okada S, Murakami M, Yamaguchi K (1997a) Characterization of hydrocarbons from the Yayoi strain of the green microalga Botryococcus braunii. Phytochem Anal 8:198–203 CrossRef
- Okada S, Tonegawa I, Matsuda H, Murakami M, Yamaguchi K (1997b) Braunixanthins 1 and 2, new carotenoids from the green micoalga Botryococcus braunii. Tetrahedron 53:11307–11316 CrossRef
- Okada S, Devarenne TP, Chapell J (2000) Molecular characterization of squalene synthase from the green microalga Botryococcus braunii, race B. Arch Biochem Biophys 373:307–317 CrossRef
- Okada S, Devarenne TP, Murakami M, Abe H, Chappell J (2004) Characterization of botryococcene synthase enzyme activity, a squalene synthase-like activity from the green microalga Botryococcus braunii, race B. Arch Biochem Biophys 422:110–118 CrossRef
- Pedroni P, Davison J, Beckert H, Bergman P, Benemann (2001) A proposal to establish an international network of CO2 and greenhouse gas abatement with microalgae. J Energy Environ Res 1:136–150
- Plain N, Largeau C, Derenne S, Couté A (1993) Variabilité morphologique de Botryococcus braunii (Chlorococcales, Chlorophyta): corrélations avec les conditions de croissance et la teneur en lipides. Phycologia 32:259–265
- Poulter CD (1990) Biosynthesis of non-head-to-tail terpenes. Formation of 1′-1 and 1′-3 linkages. Acc Chem Res 23:70–77
- Rager M-N, Metzger P (2000) Six novel tetraterpenoid ethers, lycopanerols B-G, and some other constituents from the green microalga Botryococcus braunii. Phytochemistry 54:427–437 CrossRef
- Ratledge C, Wilkinson SG (1988) An overview of microbial lipids. In: Ratledge C, Wilkinson SG (eds) Microbial lipids, vol 1. Academic Press, London pp 3–22
- Sato T, Usui S, Nakatsuka N, Sakurai S, Tsuchiya Y, Kondo Y, Hirabayashi S (2002) Innovation of novel photobioreactor for microalgae and proposal of its usage for CO2 fixation. (Proc 1st Congr Int Soc Appl Phycol) Int Conf Appl Algol 9:119–120
- Sato Y, Ito Y, Okada S, Murakami M, Abe H (2003) Biosynthesis of the triterpenoids, botryococcenes and tetramethylsqualene in the B race of Botryococcus braunii via the non-mevalonate pathway. Tetrahedron Lett 44:7035–7037 CrossRef
- Sawayama S, Inoue S, Yokoyama S (1994) Continuous culture of hydrocarbon-rich microalga Botryococcus braunii in secondarily treated sewage. Appl Microbiol Biotechnol 41:729–731
- Sawayama S, Inoue S, Dote Y, Yokoyama S-H (1995) CO2 fixation and oil production through microalga. Energy Convers Manage 36:729–731 CrossRef
- Sawayama S, Minowa T, Yokoyama S-Y (1999) Possibility of renewable energy production and CO2 mitigation by thermochemical liquefaction of microalgae. Biomass Bioenergy 17:33–39 CrossRef
- Schwender J, Seemann M, Lichtenthaler HK, Rohmer M (1996) Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side chains of chlorophylls and plastoquinone) via a novel/pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliqus. Biochem J 316:73–80
- Senousy HH (2003) A molecular taxonomic and morphological study of the green alga genus Botryococcus. PhD thesis, University of Newcastle, Newcastle upon Tyne
- Senousy HH, Beakes GW, Hack E (2004) Phylogenetic placement of Botryococcus braunii (Trebouxiophyceae) and Botryococcus sudeticus isolate UTEX 2629 (Chlorophyceae). J Phycol 40:412–423
- Summons RE, Metzger P, Largeau C, Murray AP, Hope JM (2002) Polymethylsqualanes from Botryococcus braunii in lacustrine sediments and cruce oils. Org Geochem 33:99–109 CrossRef
- Templier J, Largeau C, Casadevall E (1984) Mechanism of non-isoprenoid hydrocarbon biosynthesis in Botryococcus braunii. Phytochemistry 23:1017–1028 CrossRef
- Templier J, Largeau C, Casadevall E (1987) Effect of various inhibitors on biosynthesis of non-isoprenoid hydrocarbon biosynthesis in Botryococcus braunii. Phytochemistry 26:377–383 CrossRef
- Townsend SA (2001) Perennial domination of phytoplankton by Botryococcus and Peridinium in a discontinuously polymictic reservoir (tropical Australia). Arch Hydrobiol 151:529–548
- Villarreal-Rosales E, Metzger P, Casadevall E (1992) Ether lipid production in relation to growth in Botryococcus braunii. Phytochemistry 31:3021–3027 CrossRef
- Volova TG, Kalacheva GS, Zhila NO (2003) Specificity of lipid composition in two Botryococcus strains, the producers of liquid hydrocarbons. Russ J Plant Physiol 50:627–633 CrossRef
- Wake LV, Hillen LW (1980) Study of a “bloom” of the oil-rich alga Botryococcus braunii in the Darwin River Reservoir. Biotechnol Bioeng 22:1637–1656
- Wake LV, Hillen LW (1981) Nature and hydrocarbon content of blooms of the alga Botryococcus braunii occurring in Australian freshwater lakes. Aust J Mar Freshwater Res 32:353–367
- Wang J, Yang S, Cong W, Cai Z (2003) Effect of nutrient conditions on the growth of Botryococcus braunii. Chin J Process Eng 3:141–145
- White JD, Somers TC, Reddy GN (1986) Absolute configuration of (−) botryococcene. J Am Chem Soc 108:5352–5353
- White JD, Somers TC, Reddy GN (1992) Degradation and absolute configurational assignment to C34 botryococcene. J Org Chem 57:4991–4998
- Wolf FR, Nemethy EK, Blanding JH, Bassham JA (1985a) Biosynthesis of unusual acyclic isoprenoids in the alga Botryococcus braunii. Phytochemistry 24:733–737 CrossRef
- Wolf FR, Nonomura AM, Bassham JA (1985b) Growth and branched hydrocarbon production in a strain of Botryococcus braunii (Chlorophyta). J Phycol 21:388–396
- Yang S, Wang J, Cong W, Cai Z, Ouyang F (2004a) Utilization of nitrite as a nitrogen source by Botryococcus braunii. Biotechnol Lett 26:239–243 CrossRef
- Yang S, Wang J, Cong W, Cai Z, Ouyang F (2004b) Effects of bisulfite and sulfite on the microalga Botryococcus braunii. Enzyme Microb Technol 35:46–50 CrossRef
About this Article
- Title
- Botryococcus braunii: a rich source for hydrocarbons and related ether lipids
- Journal
-
Applied Microbiology and Biotechnology
Volume 66, Issue 5 , pp 486-496 - Cover Date
- 2005-02-01
- DOI
- 10.1007/s00253-004-1779-z
- Print ISSN
- 0175-7598
- Online ISSN
- 1432-0614
- Publisher
- Springer-Verlag
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- Authors
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-
P. Metzger
(1)
- C. Largeau (1)
-
P. Metzger
- Author Affiliations
-
- 1. Laboratoire de Chimie Bioorganique et Organique Physique, Ecole Nationale Supérieure de Chimie de Paris, 11 Rue Pierre et Marie Curie, 75231 cedex 05, Paris, France