Skip to main content

Lipids of Geochemical Interest in Microalgae

  • Living reference work entry
  • First Online:

Part of the book series: Handbook of Hydrocarbon and Lipid Microbiology ((HHLM))

Abstract

Microalgae have a long geological history and a diversity of biochemical constituents which vary systematically between algal classes. This review provides an update on those lipid constituents that have proven useful in organic geochemical studies as biomarkers for assigning sources of organic matter in seawater and sediments. These functionalized biomarkers are degraded in sediments by well-established pathways ultimately yielding hydrocarbons which can also be used to assign organic matter sources in ancient sediments and crude oils. Compound classes covered here include hydrocarbons, fatty acids, hydroxy fatty acids, fatty alcohols, alkyl diols, alkenones, alkenoates, and sterols. Information on biopolymeric substances called algaenans found in just a few algal classes is also provided.

This is a preview of subscription content, log in via an institution.

References

  • 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

    Article  PubMed  CAS  Google Scholar 

  • Ackman RG, Tocher CS, McLachlan J (1968) Marine phytoplankter fatty acids. J Fish Res Bd Canada 25:1603–1620

    Article  CAS  Google Scholar 

  • Ahmed F, Zhou WX, Schenk PM (2015) Pavlova lutheri is a high-level producer of phytosterols. Algal Res Biomass Biofuels Bioprods 10:210–217

    Google Scholar 

  • Allard B, Templier J (2000) Comparison of neutral lipid profile of various trilaminar outer cell wall (TLS)-containing microalgae with emphasis on algaenan occurrence. Phytochemistry 54:369–380

    Article  PubMed  CAS  Google Scholar 

  • Allard B, Templier J (2001) High molecular weight lipids from the trilaminar outer wall (TLS)-containing microalgae Chlorella emersonii, Scenedesmus communis and Tetraedron minimum. Phytochemistry 57:459–467

    Article  PubMed  CAS  Google Scholar 

  • Allard WG, Belt ST, Massé G, Naumann R, Robert J-M, Rowland S (2001) Tetra-unsaturated sesterterpenoids (Haslenes) from Haslea ostrearia and related species. Phytochemistry 56:795–800

    Article  PubMed  CAS  Google Scholar 

  • Balzano S, Villanueva L, de Bar M, Sinninghe Damsté JS, Schouten S (2017) Impact of culturing conditions on the abundance and composition of long chain alkyl diols in species of the genus Nannochloropsis. Org Geochem 108:9–17

    Article  CAS  Google Scholar 

  • Beastall GH, Tyndall AM, Rees HH, Goodwin TW (1974) Sterols in Porphyridium series. 4α-Methyl-5α-cholesta-8,22-dien-3β-ol and 4α,24-dimethyl-5α-cholesta-8,22-dien-3β-ol: two novel sterols from Porphyridium cruentum. Eur J Biochem 41:301–309

    Article  PubMed  CAS  Google Scholar 

  • Belt ST, Cooke DA, Robert J-M, Rowland S (1996) Structural characterisation of widespread polyunsaturated isoprenoid biomarkers: a C25 triene, tetraene and pentaene from the diatom Haslea ostrearia Simonsen. Tetrahedron Lett 37:4755–4758

    Article  CAS  Google Scholar 

  • Belt ST, Allard G, Massé G, Robert J-M, Rowland S (2000a) Important sedimentary sesterterpenoids from the diatom Pleurosigma intermedium. Chem Comm 6:501–502

    Article  Google Scholar 

  • Belt ST, Allard WG, Rintatalo J, Johns LA, van Duin ACT, Rowland SJ (2000b) Clay and acid catalysed isomerisation and cyclisation reactions of highly branched isoprenoid (HBI) alkenes: implications for sedimentary reactions and distributions. Geochim Cosmochim Acta 64:3337–3345

    Article  CAS  Google Scholar 

  • Belt ST, Allard WG, Johns L, Konig WA, Massé G, Robert J-M, Rowland S (2001a) Variable stereochemistry in highly branched isoprenoids from diatoms. Chirality 13:415–419

    Article  PubMed  CAS  Google Scholar 

  • Belt ST, Allard WG, Massé G, Robert J-M, Rowland SJ (2001b) Structural characterisation of C30 highly branched isoprenoid alkenes (rhizenes) in the marine diatom Rhizosolenia setigera. Tetrahedron Lett 42:5583–5585

    Article  CAS  Google Scholar 

  • Belt ST, Massé G, Allard WG, Robert J-M, Rowland SJ (2001c) C25 highly branched isoprenoid alkenes in planktonic diatoms of the Pleurosigma genus. Org Geochem 32:1271–1275

    Article  CAS  Google Scholar 

  • Belt ST, Massé G, Allard WG, Robert J-M, Rowland SJ (2001d) Identification of a C25 highly branched isoprenoid triene in the freshwater diatom Navicula sclesvicensis. Org Geochem 32:1169–1172

    Article  CAS  Google Scholar 

  • Belt ST, Massé G, Allard WG, Robert JM, Rowland SJ (2002) Effects of auxosporulation on distributions of C25 and C30 isoprenoid alkenes in Rhizosolenia setigera. Phytochemistry 59:141–148

    Article  PubMed  CAS  Google Scholar 

  • Belt ST, Massé G, Allard WG, Robert JM, Rowland SJ (2003) Novel monocyclic sester- and triterpenoids from the marine diatom, Rhizosolenia setigera. Tetrahedron Lett 44:9103–9106

    Article  CAS  Google Scholar 

  • Belt ST, Massé G, Rowland SJ, Poulin M, Michel C, LeBlanc B (2007) A novel chemical fossil of palaeo sea ice: IP25. Org Geochem 38:16–27

    Article  CAS  Google Scholar 

  • Belt ST, Müller J (2013) The Arctic sea ice biomarker IP25: a review of current understanding, recommendations for future research and applications in palaeo sea ice reconstructions. Quat Sci Rev 79:9–25

    Article  Google Scholar 

  • Belt ST, Smik L, Brown TA, Kim J-H, Rowland SJ, Allen CS, Gal J-K, Shin K-H, Lee JI, Taylor KWR (2016) Source identification and distribution reveals the potential of the geochemical Antarctic sea ice proxy IPSO25. Nature Comms 7:12655. https://doi.org/10.1038/ncomms12655

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Belt ST, Brown TA, Smik L, Tatarek A, Wiktor J, Stowasser G, Assmy P, Allen C, Husum K (2017) Identification of C25 highly branched isoprenoid (HBI) alkenes in diatoms of the genus Rhizosolenia in polar and sub-polar marine phytoplankton. Org Geochem 110:65–72

    Article  CAS  Google Scholar 

  • Bendif EM, Probert I, Schroeder DC, de Vargas C (2013) On the description of Tisochrysis lutea gen. nov. sp. nov. and Isochrysis nuda sp. nov. in the Isochrysidales, and the transfer of Dicrateria to the Prymnesiales (Haptophyta). J Appl Phycol 25:1763–1776

    Article  CAS  Google Scholar 

  • Bengtson S, Sallstedt T, Belivanoval V, Whitehouse M (2017) Three-dimensional preservation of cellular and subcellular structures suggests 1.6 billion-year-old crown-group red algae. PLoS Biol. https://doi.org/10.1371/journal.pbio.2000735

  • Berkaloff C, Casadevall E, Largeau C, Metzger P, Peracca S, Virlet J (1983) Hydrocarbon formation in the green alga Botryococcus braunii. 3. The resistant polymer of the walls of the hydrocarbon-rich alga Botryococcus braunii. Phytochemistry 22:389–397

    Article  CAS  Google Scholar 

  • Bertheas O, Metzger P, Largeau C (1999) A high molecular weight complex lipid, aliphatic polyaldehyde tetraterpenediol polyacetal from Botryococcus braunii (L race). Phytochemistry 50:85–96

    Article  CAS  Google Scholar 

  • Bianchi TS, Canuel EA (2011) Chemical biomarkers in aquatic ecosystems. Princeton University Press, Princeton

    Book  Google Scholar 

  • Blokker P, Schouten S, van den Ende H, de Leeuw JW, Sinninghe Damsté JS (1998a) Cell wall-specific ω-hydroxy fatty acids in some freshwater green microalgae. Phytochemistry 49:691–695

    Article  CAS  Google Scholar 

  • Blokker P, Schouten S, van den Ende H, de Leeuw JW, Hatcher PG, Sinninghe Damsté JS (1998b) Chemical structure of algaenans from the fresh water algae Tetraedron minimum, Scenedesmus communis and Pediastrum boryanum. Org Geochem 29:1453–1468

    Article  CAS  Google Scholar 

  • Brassell SC, Eglinton G, Marlowe IT, Pflaumann U, Sarnthein M (1986) Molecular stratigraphy: a new tool for climatic assessment. Nature 320:129–133

    Article  CAS  Google Scholar 

  • Brassell SC (2014) Climatic influences on the Paleogene evolution of alkenones. Paleoceanography 29:255–272

    Article  Google Scholar 

  • Briggs DEG, Summons RE (2014) Ancient biomolecules: their origins, fossilization, and role in revealing the history of life. BioEssays 36:482–490

    Article  PubMed  CAS  Google Scholar 

  • Brocks JJ, Love GD, Summons RE, Knoll AH, Logan GA, Bowden SA (2005) Biomarker evidence for green and purple sulphur bacteria in a stratified Palaeoproterozoic sea. Nature 437:866–870

    Article  PubMed  CAS  Google Scholar 

  • Brown AC, Knights PA, Conway E (1969) Hydrocarbon content and its relationship to physiological state in the green alga Botryococcus braunii. Phytochemistry 8:543–547

    Article  CAS  Google Scholar 

  • Brown TA, Belt ST, Tatarek A, Mundy CJ (2014) Source identification of the Arctic sea ice proxy IP25. Nature Comms 5:Article 4197. https://doi.org/10.1038/ncomms5197

  • Chivall D, M’Boule D, Sinke-Schoen D, Sinninghe Damsté JS, Schouten S, van der Meer MT (2014) Impact of salinity and growth phase on alkenone distributions in coastal haptophytes. Org Geochem 67:31–34

    Article  CAS  Google Scholar 

  • Conte MH, Volkman JK, Eglinton G (1994) Lipid biomarkers of the Haptophyta. In: Green JC, Leadbeater BSC (eds) The haptophyte algae. Clarendon Press, Oxford, pp 351–377

    Google Scholar 

  • Conte MH, Thompson A, Eglinton G, Green JC (1995) Lipid biomarker diversity in the coccolithophorid Emiliania huxleyi (Prymnesiophyceae) and the related species Gephyrocapsa oceanica. J Phycol 31:272–282

    Article  CAS  Google Scholar 

  • Conte MH, Thompson A, Lesley D, Harris RP (1998) Genetic and physiological influences on the alkenone/alkenoate versus growth temperature relationship in Emiliania huxleyi and Gephyrocapsa oceanica. Geochim Cosmochim Acta 62:51–68

    Article  CAS  Google Scholar 

  • Coolen MJL, Muyzer G, Rijpstra WIC, Schouten S, Volkman JK, Sinninghe Damsté JS (2004) Combined DNA and lipid analyses of sediments reveal changes in Holocene haptophyte and diatom populations in an Antarctic Lake. Earth Planet Sci Lett 223:225–239

    Article  CAS  Google Scholar 

  • Cranwell PA, Creighton ME, Jaworski GHM (1988) Lipids of four species of freshwater chrysophytes. Phytochemistry 27:1053–1059

    Article  CAS  Google Scholar 

  • Cranwell PA, Jaworski GHM, Bickley HM (1990) Hydrocarbons, sterols, esters and fatty acids in six freshwater chlorophytes. Phytochemistry 29:145–151

    Article  CAS  Google Scholar 

  • De Bar MW, Dorhout DJC, Hopmans EC, Rampen SW, Sinninghe Damsté JS, Schouten S (2016) Constraints on the application of long chain diol proxies in the Iberian Atlantic margin. Org Geochem 101:184–195

    Article  CAS  Google Scholar 

  • D’Alessandro EB, Antoniosi Filho NR (2016) Concepts and studies on lipid and pigments of microalgae: a review. Renew Sust Energ Rev 58:832–841

    Article  CAS  Google Scholar 

  • D’Andrea WJ, Huang Y (2005) Long chain alkenones in Greenland lake sediments: Low δ13C values and exceptional abundance. Org Geochem 36:1234–1241

    Article  CAS  Google Scholar 

  • D’Andrea WJ, Lage M, Martiny JBH, Laatsch AD, Amaral-Zettler LA, Sogin ML, Huang YS (2006) Alkenone producers inferred from well-preserved 18S rDNA in Greenland lake sediments. J Geophys Res Biogeosci 111(G3). https://doi.org/10.1029/2005JG000121

  • D’Andrea WJ, Theroux S, Bradley RS, Huang XH (2016) Does phylogeny control \( {U}_{37}^K \) temperature sensitivity? Implications for lacustrine alkenone paleothermometry. Geochim Cosmochim Acta 175:168–180

    Article  CAS  Google Scholar 

  • de Leeuw JW, Largeau C (1993) A review of macromolecular organic compounds that comprise living organisms and their role in kerogen, coal and petroleum formation. In: Engel MH, Macko SA (eds) Organic geochemistry. Plenum Press, New York, pp 23–72

    Chapter  Google Scholar 

  • de Leeuw JW, van der Meer JW, Rijpstra WIC, Schenck PA (1980) On the occurrence and structural identification of long chain ketones and hydrocarbons in sediments. In: Douglas AG, Maxwell JR (eds) Advances in organic geochemistry 1979. Pergamon Press, Oxford, pp 211–217

    Google Scholar 

  • de Leeuw JW, Rijpstra WIC, Schenck PA (1981) The occurrence and identification of C30, C31 and C32 alkan-1,15-diols and alkan-15-one-1-ols in Unit I and Unit II Black Sea sediments. Geochim Cosmochim Acta 45:2281–2285

    Google Scholar 

  • Derenne S, Largeau C, Casadevall E, Tegelaar E, de Leeuw JW (1988) Relationships between algal coals and resistant cell wall biopolymers of extant algae as revealed by Py-GC-MS. Fuel Process Tech 20:93–101

    Article  CAS  Google Scholar 

  • Derenne S, Largeau C, Casadevall E, Berkaloff C (1989) Occurrence of a resistant biopolymer in the L race of Botryococcus braunii. Phytochemistry 28:1137–1142

    Article  CAS  Google Scholar 

  • Derenne S, Largeau C, Casadevall E, Sellier N (1990) Direct relationship between the resistant biopolymer and the tetraterpenic hydrocarbon in the lycopadiene race of Botryococcus braunii. Phytochemistry 29:2187–2192

    Article  CAS  Google Scholar 

  • Dodson VJ, Mouget JL, Dahmen JL, Leblond JD (2014) The long and short of it: temperature-dependent modifications of fatty acid chain length and unsaturation in the galactolipid profiles of the diatoms Haslea ostrearia and Phaeodactylum tricornutum. Hydrobiologia 727:95–107

    Article  CAS  Google Scholar 

  • Dodson VJ, Leblond JD (2015) Now you see it, now you don’t: differences in hydrocarbon production in the diatom Phaeodactylum tricornutum due to growth temperature. J Appl Phycol 27:1463–1472

    Article  CAS  Google Scholar 

  • Dunstan GA, Volkman JK, Barrett SM, Garland CD (1993) Changes in the lipid composition and maximisation of the polyunsaturated fatty acid content of three microalgae grown in mass culture. J Appl Phycol 5:71–83

    Article  CAS  Google Scholar 

  • Dunstan GA, Volkman JK, Barrett SM, Leroi JM, Jeffrey SW (1994) Essential polyunsaturated fatty acids from 14 species of diatom (Bacillariophyceae). Phytochemistry 35:155–161

    Article  CAS  Google Scholar 

  • Epstein BL, D'Hondt S, Quinn JG, Zhang J, Hargraves PE (1998) An effect of dissolved nutrient concentrations on alkenone-based temperature estimates. Paleoceanography 13:122–126

    Article  Google Scholar 

  • Epstein BL, D'Hondt S, Hargraves PE (2001) The possible metabolic role of C37 alkenones in Emiliania huxleyi. Org Geochem 32:867–875

    Article  CAS  Google Scholar 

  • Gatellier J-PLA, de Leeuw JW, Sinninghe Damsté JS, Derenne S, Largeau C, Metzger PA (1993) A comparative study of macromolecular substances of a coorongite and cell walls of the extant alga Botryococcus braunii. Geochim Cosmochim Acta 57:2053–2068

    Article  CAS  Google Scholar 

  • Gelin F, de Leeuw JW, Sinninghe Damsté JS, Derenne S, Largeau C, Metzger P (1994) The similarity of chemical structures of soluble aliphatic polyaldehyde and insoluble algaenan in the green microalga Botryococcus braunii race A as revealed by analytical pyrolysis. Org Geochem 21:423–435

    Article  CAS  Google Scholar 

  • Gelin F, Boogers I, Noordeloos AAM, Sinninghe Damsté JS, Hatcher PG, de Leeuw JW (1996) Novel, resistant microalgal polyethers: an important sink of organic carbon in the marine environment? Geochim Cosmochim Acta 60:1275–1280

    Article  CAS  Google Scholar 

  • Gelin F, Volkman JK, de Leeuw JW, Sinninghe Damsté JS (1997a) Mid-chain hydroxy long-chain fatty acids in microalgae from the genus Nannochloropsis. Phytochemistry 45:641–646

    Article  CAS  Google Scholar 

  • Gelin F, Boogers I, Noordeloos AAM, Sinninghe Damsté JS, Riegman R, de Leeuw JW (1997b) Resistant biomacromolecules in marine microalgae of the classes Eustigmatophyceae and Chlorophyceae: geochemical implications. Org Geochem 26:659–675

    Article  CAS  Google Scholar 

  • Gelin F, Volkman JK, Largeau C, Derenne S, Sinninghe Damsté JS, de Leeuw JW (1999) Distribution of aliphatic, non-hydrolysable biopolymers in marine microalgae. Org Geochem 30:147–159

    Article  CAS  Google Scholar 

  • Gelpi E, Schneider H, Mann J, Oró J (1970) Hydrocarbons of geochemical significance in microscopic algae. Phytochemistry 9:603–612

    Article  CAS  Google Scholar 

  • Gold DA, Caron A, Fournier GP, Summons RE (2017) Paleoproterozoic sterol biosynthesis and the rise of oxygen. Nature. https://doi.org/10.1038/nature21412

  • Goossens H, de Leeuw JW, Schenck PA, Brassell SC (1984) Tocopherols as likely precursors of pristane in ancient sediments and crude oils. Nature 312:440–442

    Article  CAS  Google Scholar 

  • Gouveia L, Marques AE, Sousa JM, Moura P, Bandarra NM (2010) Microalgae – source of natural bioactive molecules as functional ingredients. Food Sci Technol Bull Funct Foods 7:21–37

    Article  Google Scholar 

  • Grossi V, Raphel D, Aubert C, Rontani J-F (2000) The effect of growth temperature on the long-chain alkenes composition in the marine coccolithophorid Emiliania huxleyi. Phytochemistry 54:393–399

    Article  PubMed  CAS  Google Scholar 

  • Grossi V, Beker B, Geenevasen JAJ, Schouten S, Raphel D, Fontaine M-F, Sinninghe Damsté JS (2004) C25 highly branched isoprenoid alkenes from the marine benthic diatom Pleurosigma strigosum. Phytochemistry 65:3049–3055

    Article  PubMed  CAS  Google Scholar 

  • He J, Zhao MX, Li L, Wang H, Wang PX (2008) Biomarker evidence of relatively stable community structure in the northern South China Sea during the last glacial and Holocene. Terr Atmos Ocean Sci 19:377–387

    Article  Google Scholar 

  • Ho SL, Naafs BDA, Lamy F (2013) Alkenone paleothermometry based on the haptophyte algae. In: Elias SA (ed) The Encyclopedia of quaternary science. Elsevier, Amsterdam, pp 755–764

    Chapter  Google Scholar 

  • Huang Z, Poulter CD (1989) Tetramethylsqualene, a triterpene from Botryococcus braunii var Showa. Phytochemistry 28:1467–1470

    Article  CAS  Google Scholar 

  • Jeffrey SW, Brown MR, Volkman JK (1994) Haptophytes as feedstocks in mariculture. In: Green JC, Leadbeater BSC (eds) The haptophyte algae, Systematics Association special volume no. 51. Clarendon Press, Oxford

    Google Scholar 

  • Jia J, Han DX, Gerken HG, Li YT, Sommerfeld M, Hu Q, Xu J (2015) Molecular mechanisms for photosynthetic carbon partitioning into storage neutral lipids in Nannochloropsis oceanica under nitrogen-depletion conditions. Algal Res Biomass Biofuels Bioprods 7:66–77

    Google Scholar 

  • Kaiser J, Belt ST, Tomczak M, Brown TA, Wasmund N, Arz HW (2016) C25 highly branched isoprenoid alkenes in the Baltic Sea produced by the marine planktonic diatom Pseudosolenia calcar-avis. Org Geochem 93:51–58

    Article  CAS  Google Scholar 

  • Kawachi M, Tanoi T, Demura M, Kaya K, Watanabe MM (2012) Relationship between hydrocarbons and molecular phylogeny of Botryococcus braunii. Algal Res 1:114–119

    Article  Google Scholar 

  • Khozin-Goldberg I (2016) Lipid metabolism in microalgae. In: Borowitzka M, Beardall J, Raven JA (eds) The physiology of microalgae, Developments in applied phycology series 6. Springer, Cham, pp 413–484

    Chapter  Google Scholar 

  • Lang I, Hodac L, Friedl T, Feussner I (2011) Fatty acid profiles and their distribution patterns in microalgae: a comprehensive analysis of more than 2000 strains from the SAG culture collection. BMC Plant Biol 11:124. https://doi.org/10.1186/1471-2229-11-124

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Leblond JD, Roche SA, Porter NM, Howard JC, Dunlap NK (2011) Sterol biosynthesis in the harmful marine dinoflagellate, Karenia brevis: identification of biosynthetic intermediates produced during exposure to the fungicide fenpropidine. Phycol Res 59:54–63

    Article  CAS  Google Scholar 

  • Lee RF, Loeblich AR III (1971) Distribution of 21:6 hydrocarbon and its relationship to 22:6 fatty acid in algae. Phytochemistry 10:593–602

    Article  CAS  Google Scholar 

  • Li YR, Ye MW, Zhang RT, Xu JL, Zhou CX, Yan XJ (2016) Lipid compositions in diatom Conticribra weissflogii under static and aerated culture conditions. Phycol Res 64:281–290

    Article  CAS  Google Scholar 

  • Lipp JS, Hinrichs K-U (2009) Structural diversity and fate of intact polar lipids in marine sediments. Geochim Cosmochim Acta 73:6816–6833

    Article  CAS  Google Scholar 

  • Longo WM, Dillon JT, Tarozo R, Salacup JM, Huang Y (2013) Unprecedented separation of long chain alkenones from gas chromatography with a poly(trifluoropropylmethylsiloxane) stationary phase. Org Geochem 65:94–102

    Article  CAS  Google Scholar 

  • Longo WM, Theroux S, Giblin AE, Zheng YS, Dillon JT, Huang YS (2016) Temperature calibration and phylogenetically distinct distributions for freshwater alkenones: evidence from northern Alaskan lakes. Geochim Cosmochim Acta 180:177–196

    Article  CAS  Google Scholar 

  • Mansour MP, Volkman JK, Holdsworth DG, Jackson AE, Blackburn SI (1999) Very-long-chain (C28) highly unsaturated fatty acids in marine dinoflagellates. Phytochemistry 50:541–548

    Article  CAS  Google Scholar 

  • Marlowe IT, Green JC, Neal AC, Brassell SC, Eglinton G, Course PA (1984a) Long chain (n-C37–C39) alkenones in the Prymnesiophyceae. Distribution of alkenones and other lipids and their taxonomic significance. Br Phycol J 19:203–216

    Article  Google Scholar 

  • Marlowe IT, Brassell SC, Eglinton G, Green JC (1984b) Long chain unsaturated ketones and esters in living algae and marine sediments. Org Geochem 6:135–141

    Article  CAS  Google Scholar 

  • Martinez-Roldan AJ, Perales-Vela HV, Canizares-Villanueva RO, Torzillo G (2014) Physiological response of Nannochloropsis sp. to saline stress in laboratory batch cultures. J Appl Phycol 26:115–121

    Article  CAS  Google Scholar 

  • Massé G, Belt ST, Rowland SJ (2004a) Biosynthesis of unusual monocyclic alkenes by the diatom Rhizosolenia setigera (Brightwell). Phytochemistry 65:1101–1106

    Article  PubMed  CAS  Google Scholar 

  • Massé G, Belt ST, Rowland SJ, Rohmer M (2004b) Isoprenoid biosynthesis in the diatoms Rhizosolenia setigera (Brightwell) and Haslea ostrearia (Simonsen). Proc Nat Acad Sci USA 101:4413–4418

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Matsumoto GI, Nagashima H (1984) Occurrence of 3-hydroxy acids in microalgae and cyanobacteria and their geochemical significance. Geochim Cosmochim Acta 48:1683–1687

    Article  CAS  Google Scholar 

  • Matsumoto GI, Shioya M, Nagashima H (1984) Occurrence of 2-hydroxy acids in microalgae. Phytochemistry 23:1421–1423

    Article  CAS  Google Scholar 

  • Méjanelle L, Sanchez-Gargallo A, Bentaleb I, Grimalt JO (2003) Long chain n-alkyl diols, hydroxy ketones and sterols in a marine eustigmatophyte, Nannochloropsis gaditana, and in Brachionus plicatilis feeding on the algae. Org Geochem 34:527–538

    Article  CAS  Google Scholar 

  • Mercer EI, Davies CL (1974) Chlorosulfolipids of Tribonema aequale. Phytochemistry 13:1607–1610

    Article  CAS  Google Scholar 

  • Mercer EI, Davies CL (1979) Distribution of chlorosulpholipids in algae. Phytochemistry 18:457–462

    Article  CAS  Google Scholar 

  • Metzger P, Casadevall E, Pouet MJ, Pouet Y (1985) Structures of some botryococcenes: branched hydrocarbons from the B-race of the green alga Botryococcus braunii. Phytochemistry 24:2995–3002

    Article  CAS  Google Scholar 

  • Metzger P, Casadevall E (1987) Lycopadiene, a tetraterpenoid hydrocarbon from new strains of the green alga Botryococcus braunii. Tetrahedron Lett 28:3931–3934

    Article  CAS  Google Scholar 

  • Metzger P, Allard B, Casadevall E, Berkaloff C, Cout A (1990) Structure and chemistry of a new race of Botryococcus braunii (Chlorophyceae) that produces lycopadiene, a tetraterpenoid hydrocarbon. J Phycol 26:258–266

    Article  CAS  Google Scholar 

  • Metzger P, Largeau C (2005) Botryococcus braunii: a rich source for hydrocarbons and related ether lipids. Appl Microbiol Biotechnol 66:486–496

    Article  PubMed  CAS  Google Scholar 

  • Mitra M, Patidar SK, George B, Shaha F, Mishra SA (2015) A euryhaline Nannochloropsis gaditana with potential for nutraceutical (EPA) and biodiesel production. Algal Res Biomass Biofuels Bioprod 8:161–167

    Google Scholar 

  • Nagashima H, Matsumoto GI, Fukuda I (1986) Hydrocarbons and fatty acids in two strains of the hot spring alga Cyanidium caldarium. Phytochemistry 25:2339–2341

    Article  CAS  Google Scholar 

  • Nakamura H, Sawada K, Araie H, Suzuki I, Shiraiwa Y (2014) Long chain alkenes, alkenones and alkenoates produced by the haptophyte alga Chrysotila lamellosa CCMP1307 isolated from a salt marsh. Org Geochem 66:90–97

    Article  CAS  Google Scholar 

  • Nakamura H, Sawada K, Araie H, Suzuki I, Shiraiwa Y (2015) n-Nonacosadienes from the marine haptophytes Emiliania huxleyi and Gephyrocapsa oceanica. Phytochemistry 111:107–113

    Article  PubMed  CAS  Google Scholar 

  • Nakamura H, Sawada K, Araie H, Shiratori T, Ishida K-I, Suzuki I, Shiraiwa Y (2016) Composition of long chain alkenones and alkenoates as a function of growth temperature in marine haptophyte Tisochrysis lutea. Org Geochem 99:78–89

    Article  CAS  Google Scholar 

  • Nes WD (2011) Biosynthesis of cholesterol and other sterols. Chem Rev 111:6423–6451

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Nichols PD, Volkman JK, Palmisano AC, Smith GA, White DC (1988) Occurrence of an isoprenoid C25 diunsaturated alkene and high neutral lipid content in Antarctic sea-ice diatom communities. J Phycol 24:90–96

    Article  CAS  Google Scholar 

  • Olofsson M, Lamela T, Nilsson E, Berge JP, Del Pino V, Uronen P, Legrand C (2012) Seasonal variation of lipids and fatty acids of the microalgae Nannochloropsis oculata grown in outdoor large-scale photobioreactors. Energies 5:1577–1592

    Article  CAS  Google Scholar 

  • Olofsson M, Lamela T, Nilsson E, Berge JP, Del Pino V, Uronen P, Legrand C (2014) Combined effects of nitrogen concentration and seasonal changes on the production of lipids in Nannochloropsis oculata. Mar Drugs 12:1891–1910

    Article  PubMed  PubMed Central  Google Scholar 

  • Pal D, Khozin-Goldberg I, Cohen Z, Boussiba S (2011) The effect of light, salinity, and nitrogen availability on lipid production by Nannochloropsis sp. Appl Microbiol Biotechnol 90:1429–1441

    Article  PubMed  CAS  Google Scholar 

  • Pan H, Culp RA, Sun MY (2017) Influence of physiological states of Emiliania huxleyi cells on their lipids and associated molecular isotopic compositions during microbial degradation. J Exp Mar Biol Ecol 488:1–9

    Article  CAS  Google Scholar 

  • Patterson GW (1969) Sterols of Chlorella. III. Species containing ergosterol. Comp Biochem Physiol 31:391–394

    Article  CAS  Google Scholar 

  • Patterson GW, Gladu PK, Wikfors GH, Lusby WR (1992) Unusual tetraene sterols in some phytoplankton. Lipids 27:154–156

    Article  CAS  Google Scholar 

  • Patterson GW, Tsitsa-Tzardis E, Wikfors GH, Gladu PK, Chitwood DJ, Harrison D (1994a) Sterols and alkenones of Isochrysis. Phytochemistry 35:1233–1236

    Article  CAS  Google Scholar 

  • Patterson GW, Tsitsa-Tzardis E, Wikfors GH, Ghosh P, Smith BC, Gladu PK (1994b) Sterols of eustigmatophytes. Lipids 29:661–664

    Article  PubMed  CAS  Google Scholar 

  • Pedro Canavate J, Armada I, Luis Rios J, Hachero-Cruzado I (2016) Exploring occurrence and molecular diversity of betaine lipids across taxonomy of marine microalgae. Phytochemistry 124:68–78

    Article  CAS  Google Scholar 

  • Pelusi A, Hanawa Y, Araie H, Suzuki I, Giordano M, Shiraiwa Y (2016) Rapid detection and quantification of haptophyte alkenones by Fourier transform infrared spectroscopy (FTIR). Algal Res Biomass Biofuels Bioprods 19:48–56

    Google Scholar 

  • Poulin M, Massé G, Belt ST, Delavault P, Rousseau F, Robert JM, Rowland SJ (2004) Morphological, biochemical and molecular evidence for the transfer of Gyrosigma nipkowii Meister to the genus Haslea (Bacillariophyta). Eur J Phycol 39:181–195

    Article  CAS  Google Scholar 

  • Prahl FG, Wakeham SG (1987) Calibration of unsaturation patterns in long-chain ketone compositions for palaeotemperature assessment. Nature 330:367–369

    Article  CAS  Google Scholar 

  • Prahl FG, Muehlhausen LA, Zahnle DL (1988) Further evaluation of long-chain alkenones as indicators of paleoceanographic conditions. Geochim Cosmochim Acta 52:2303–2310

    Article  CAS  Google Scholar 

  • Prahl FG, Wolfe GV, Sparrow MA (2003) Physiological impacts on alkenone paleothermometry. Paleoceanography 18(2), art. no.-1025. https://doi.org/10.1029/2002PA000803

    Google Scholar 

  • Prahl FG, Rontani J-F, Volkman JK, Sparrow MA, Royer IM (2006) Unusual C35 and C36 alkenones in a paleoceanographic benchmark strain of Emiliania huxleyi. Geochim Cosmochim Acta 70:2856–2867

    Article  CAS  Google Scholar 

  • Rampen SW, Schouten S, Hopmans EC, Abbas B, Noordeloos AAM, Geenevasen JAJ, Moldowan JM, Denisevich P, Sinninghe Damsté JS (2009a) Occurrence and biomarker potential of 23-methyl steroids in diatoms and sediments. Org Geochem 40:219–228

    Article  CAS  Google Scholar 

  • Rampen SW, Volkman JK, Hur SB, Abbas BA, Schouten S, Jameson ID, Holdsworth DG, Bae JH, Sinninghe Damsté JS (2009b) Occurrence of gorgosterol in diatoms of the genus Delphineis. Org Geochem 40:144–147

    Article  CAS  Google Scholar 

  • Rampen SW, Abbas BA, Schouten S, Sinninghe Damsté JS (2010) A comprehensive study of sterols in marine diatoms (Bacillariophyta): implications for their use as tracers for diatom productivity. Limnol Oceanogr 55:91–105

    Article  CAS  Google Scholar 

  • Rampen SW, Schouten S, Sinninghe Damsté JS (2011) Occurrence of long chain 1,14-diols in Apedinella radians. Org Geochem 42:572–574

    Article  CAS  Google Scholar 

  • Rampen SW, Datema M, Rodrigo-Gamiz M, Schouten S, Reichart G-J, Sinninghe Damsté JS (2014) Sources and proxy potential of longchain alkyl diols in lacustrine environments. Geochim Cosmochim Acta 144:59–71

    Article  CAS  Google Scholar 

  • Rechka JA, Maxwell JR (1988) Unusual long chain ketones of algal origin. Tetrahedron Lett 29:2599–2600

    Article  CAS  Google Scholar 

  • Rezanka T, Lukaysky J, Nedbalova L, Sigler K (2017) Lipidomic profile in three species of dinoflagellates (Amphidinium carterae, Cystodinium sp., and Peridinium aciculiferum) containing very long chain polyunsaturated fatty acids. Phytochemistry 139:88–97

    Article  PubMed  CAS  Google Scholar 

  • Rieley G, Teece MA, Peakman TM, Raven AM, Greene KJ, Clarke TP, Murray M, Leftley JW, Campbell CN, Harris RP, Parkes RJ, Maxwell JR (1998) Long-chain alkenes of the haptophytes Isochrysis galbana and Emiliania huxleyi. Lipids 33:617–625

    Article  PubMed  CAS  Google Scholar 

  • Rontani J-F, Marchand D, Volkman JK (2001) NaBH4 reduction of alkenones to the corresponding alkenols: a useful tool for their characterisation in natural samples. Org Geochem 32:1329–1341

    Article  CAS  Google Scholar 

  • Rontani J-F, Beker B, Volkman JK (2004) Long-chain alkenones and related compounds in the benthic haptophyte Chrysotila lamellosa Anand HAP 17. Phytochemistry 65:117–126

    Article  PubMed  CAS  Google Scholar 

  • Rontani J-F, Prahl FG, Volkman JK (2006a) Characterization of unusual alkenones and alkyl alkenoates by electron ionization gas chromatography/mass spectrometry. Rapid Comm Mass Spectrom 20:583–588

    Article  CAS  Google Scholar 

  • Rontani J-F, Prahl FG, Volkman JK (2006b) Re-examination of the double bond positions of alkenones and derivatives: biosynthetic implications. J Phycol 42:800–813

    Article  CAS  Google Scholar 

  • Rontani J-F, Harji R, Guasco S, Prahl FG, Volkman JK, Bhosle NB, Bonin P (2008) Degradation of alkenones by aerobic heterotrophic bacteria: selective or not? Org Geochem 39:34–51

    Article  CAS  Google Scholar 

  • Rosell-Melé A (1998) Interhemispheric appraisal of the value of alkenone indices as temperature and salinity proxies in high-latitude locations. Paleoceanography 13:694–703

    Article  Google Scholar 

  • Rowland SJ, Robson JN (1990) The widespread occurrence of highly branched acyclic C20, C25 and C30 hydrocarbons in recent sediments and biota – a review. Mar Env Res 30:191–216

    Article  CAS  Google Scholar 

  • Rowland SJ, Belt ST, Cooke DA, Hird SJ, Neeley S, Robert J-M (1995) Structural characterisation of saturated through heptaunsaturated highly branched isoprenoids. In: Grimalt J, Dorronsoro C (eds) Organic geochemistry: developments and applications to energy, climate, environment and human history. A.I.G.O.A. Donostia-San Sebastian, Spain, pp 580–582

    Google Scholar 

  • Rowland SJ, Allard WG, Belt ST, Massé G, Robert J-M, Blackburn S, Frampton D, Revill AT, Volkman JK (2001) Factors influencing the distributions of polyunsaturated terpenoids in the diatom, Rhizosolenia setigera. Phytochemistry 58:717–728

    Article  PubMed  CAS  Google Scholar 

  • Sachs JP, Maloney AE, Gregersen J, Paschall C (2016) Effect of salinity on 2H/1H fractionation in lipids from continuous cultures of the coccolithophorid Emiliania huxleyi. Geochim Cosmochim Acta 189:96–109

    Article  CAS  Google Scholar 

  • Sanz PC, Smik L, Belt ST (2016) On the stability of various highly branched isoprenoid (HBI) lipids in stored sediments and sediment extracts. Org Geochem 97:74–77

    Article  CAS  Google Scholar 

  • Scholz MJ, Weiss TL, Jinkerson RE, Jing J, Roth R, Goodenough U, Posewitz MC, Gerken HG (2014) Ultrastructure and composition of the Nannochloropsis gaditana cell wall. Eukaryot Cell 13:1450–1464

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Schouten S, Klein Breteler WCM, Blokker P, Rijpstra WIC, Grice K, Baas M, Sinninghe Damsté JS (1998) Biosynthetic effects on the stable carbon isotopic compositions of algal lipids: implications for deciphering the carbon isotopic biomarker record. Geochim Cosmochim Acta 62:1397–1406

    Article  CAS  Google Scholar 

  • Serive B, Nicolau E, Bérard JB, Kaas R, Pasquet V, Picot L, Cadoret JP (2017) Community analysis of pigment patterns from 37 microalgae strains reveals new carotenoids and porphyrins characteristic of distinct strains and taxonomic groups. PLoS One 12(2). https://doi.org/10.1371/journal.pone.0171872

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Shiratake T, Sato A, Minoda A, Tsuzuki M, Sato N (2013) Air-drying of cells, the novel conditions for stimulated synthesis of triacylglycerol in a green alga, Chlorella kessleri. PLoS One 8(11). https://doi.org/10.1371/journal.pone.0079630

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Shukla M, Dhar DW (2013) Biotechnological potentials of microalgae: past and present scenario. Vegetos 26:229–237

    Google Scholar 

  • Sikes EL, Volkman JK (1993) Calibration of alkenone unsaturation ratios (\( {U}_{37}^{K^{\prime }} \)) for paleotemperature estimation in cold polar waters. Geochim Cosmochim Acta 57:1883–1889

    Article  CAS  Google Scholar 

  • Sikes EL, Sicre MA (2002) Relationship of the tetra-unsaturated C37 alkenone to salinity and temperature: implications for paleoproxy applications. Geochem Geophys Geosyst 3:Article 1063. https://doi.org/10.1029/2002GC000345

    Article  Google Scholar 

  • Sinninghe Damsté JS, Rijpstra WIC, Schouten S, Peletier H, van der Maarel MJEC, Gieskes WWC (1999a) A C25 highly branched isoprenoid alkene and C25 and C27 n-polyenes in the marine diatom Rhizosolenia setigera. Org Geochem 30:95–100

    Article  Google Scholar 

  • Sinninghe Damsté JS, Schouten S, Rijpstra WIC, Hopmans EC, Peletier H, Gieskes WWC, Geenevasen JAJ (1999b) Structural identification of the C25 highly branched isoprenoid pentaene in the marine diatom Rhizosolenia setigera. Org Geochem 30:1581–1583

    Article  Google Scholar 

  • Sinninghe Damsté JS, Rampen S, Rijpstra WIC, Abbas B, Muyzer G, Schouten S (2003) A diatomaceous origin for long-chain diols and mid-chain hydroxy methyl alkanoates widely occurring in Quaternary marine sediments: indicators for high-nutrient conditions. Geochim Cosmochim Acta 67:1339–1348

    Article  CAS  Google Scholar 

  • Sinninghe Damsté JS, Muyzer G, Abbas B, Rampen SW, Massé G, Allard WG, Belt ST, Robert JM, Rowland SJ, Moldowan JM, Barbanti SM, Fago FJ, Denisevich P, Dahl J, Trindade LAF, Schouten S (2004) The rise of the rhizosolenid diatoms. Science 304:584–587

    Article  CAS  Google Scholar 

  • Smik L, Belt ST (2017) Distributions of the Arctic sea ice biomarker proxy IP25 and two phytoplanktonic biomarkers in surface sediments from West Svalbard. Org Geochem 105:39–41

    Article  CAS  Google Scholar 

  • Sorigué D, Légeret B, Cuiné S, Morales P, Mirabella B, Guédeney G, Li-Beisson Y, Jetter R, Peltier G, Beisson F (2016) Microalgae synthesize hydrocarbons from long-chain fatty acids via a light-dependent pathway. Plant Physiol 171:2393–2405

    PubMed  PubMed Central  Google Scholar 

  • Stonik V, Stonik I (2015) Low-molecular-weight metabolites from diatoms: structures, biological roles and biosynthesis. Mar Drugs 13:3672–3709

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Stranska-Zachariasova M, Kastanek P, Dzuman Z, Rubert J, Godula M, Hajslova J (2016) Bioprospecting of microalgae: proper extraction followed by high performance liquid chromatographic-high resolution mass spectrometric fingerprinting as key tools for successful metabolom characterization. J Chrom B Analyt Techol Biomed Life Sci 1015:22–33

    Article  CAS  Google Scholar 

  • Tegelaar EW, de Leeuw JW, Derenne S, Largeau CA (1989) A reappraisal of kerogen formation. Geochim Cosmochim Acta 53:3103–3106

    Article  CAS  Google Scholar 

  • Templier J, Diesendorf C, Largeau C, Casadevall E (1992) Metabolism of normal-alkadienes in the A Race of Botryococcus braunii. Phytochemistry 31:113–120

    Article  CAS  Google Scholar 

  • Templier J, Largeau C, Casadevall E (1993) Variations in external and internal lipids associated with inhibition of the resistant biopolymer from the a race of Botryococcus braunii. Phytochemistry 33:1079–1086

    Article  CAS  Google Scholar 

  • Theroux S, D’Andrea WJ, Toney J, Amaral-Zettler L, Huang Y (2010) Phylogenetic diversity and evolutionary relatedness of alkenone-producing haptophyte algae in lakes: implications for continental paleotemperature reconstructions. Earth Planet Sci Lett 300:311–320

    Article  CAS  Google Scholar 

  • Theroux S, Toney J, Amaral-Zettler L, Huang Y (2013) Production and temperature sensitivity of long chain alkenones in the cultured haptophyte Pseudoisochrysis paradoxa. Org Geochem 62:68–73

    Article  CAS  Google Scholar 

  • Toney JL, Theroux S, Andersen RA, Coleman A, Amaral-Zettler L, Huang YS (2012) Culturing of the first 37:4 predominant lacustrine haptophyte: geochemical, biochemical, and genetic implications. Geochim Cosmochim Acta 78:51–64

    Article  CAS  Google Scholar 

  • Versteegh GJM, Bosch HJ, de Leeuw JW (1997) Potential palaeoenvironmental information of C24 to C36 mid-chain diols, keto-ols and mid-chain hydroxy fatty acids: a critical review. Org Geochem 27:1–13

    Article  CAS  Google Scholar 

  • Versteegh GJM, Riegman R, de Leeuw JW, Jansen JHF (2001) \( {U}_{37}^{K^{\prime }} \) values for Isochrysis galbana as a function of culture temperature, light intensity and nutrient concentrations. Org Geochem 32:785–794

    Article  CAS  Google Scholar 

  • Villanueva L, Besseling M, Rodrigo-Gamiz M, Rampen SW, Verschuren D, Sinninghe Damsté JS (2014a) Potential biological sources of long chain alkyl diols in a lacustrine system. Org Geochem 68:27–30

    Article  CAS  Google Scholar 

  • Villanueva L, Rijpstra WIC, Schouten S, Sinninghe Damsté JS (2014b) Genetic biomarkers of the sterol-biosynthetic pathway in microalgae. Env Microbiol Rep 6:35–44

    Article  CAS  Google Scholar 

  • Volkman JK, Johns RB (1977) The geochemical significance of positional isomers of unsaturated fatty acids from an intertidal zone sediment. Nature 267:693–694

    Article  CAS  Google Scholar 

  • Volkman JK, Eglinton G, Corner EDS, Sargent JR (1980a) Novel unsaturated straight-chain C37–C39 methyl and ethyl ketones in marine sediments and a coccolithophorid Emiliania huxleyi. In: Douglas AG, Maxwell JR (eds) Advances in organic geochemistry 1979. Pergamon Press, Oxford, pp 219–227

    Google Scholar 

  • Volkman JK, Eglinton G, Corner EDS, Forsberg TEV (1980b) Long chain alkenes and alkenones in the marine coccolithophorid Emiliania huxleyi. Phytochemistry 19:2619–2622

    Article  Google Scholar 

  • Volkman JK (1986) A review of sterol markers for marine and terrigenous organic matter. Org Geochem 9:83–99

    Article  CAS  Google Scholar 

  • Volkman JK, Burton HR, Everitt DA, Allen DI (1988) Pigment and lipid compositions of algal and bacterial communities in Ace Lake, Vestfold Hills, Antarctica. Hydrobiologia 165:41–57

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Dunstan GA, Jeffrey SW (1992) C30–C32 alkyl diols and unsaturated alcohols in microalgae of the class Eustigmatophyceae. Org Geochem 18:131–138

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Dunstan GA, Jeffrey SW (1993) Geochemical significance of the occurrence of dinosterol and other 4-methyl sterols in a marine diatom. Org Geochem 20:7–15

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Dunstan GA (1994a) C25 and C30 highly branched isoprenoid alkenes in laboratory cultures of two marine diatoms. Org Geochem 21:407–413

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Dunstan GA, Jeffrey SW (1994b) Sterol biomarkers for microalgae from the green algal class Prasinophyceae. Org Geochem 21:1211–1218

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Blackburn SI, Sikes EL (1995) Alkenones in Gephyrocapsa oceanica: implications for studies of paleoclimate. Geochim Cosmochim Acta 59:513–520

    Article  CAS  Google Scholar 

  • Volkman JK, Farmer CL, Barrett SM, Sikes EL (1997) Unusual dihydroxysterols as chemotaxonomic markers for microalgae from the order Pavlovales (Haptophyceae). J Phycol 33:1016–1023

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Blackburn SI, Mansour MP, Sikes EL, Gelin F (1998) Microalgal biomarkers: a review of recent research developments. Org Geochem 29:1163–1179

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Blackburn SI (1999a) Eustigmatophyte microalgae are potential sources of C29 sterols, C22–C28 n-alcohols and C28–C32 n-alkyl diols in freshwater environments. Org Geochem 30:307–318

    Article  CAS  Google Scholar 

  • Volkman JK, Barrett SM, Blackburn SI (1999b) Fatty acids and hydroxy fatty acids in three species of freshwater eustigmatophytes. J Phycol 35:1005–1012

    Article  CAS  Google Scholar 

  • Volkman JK (2000) Ecological and environmental factors affecting alkenone distributions in seawater and sediments. Geochem Geophys Geosyst 1: Paper number 2000GC000061

    Article  Google Scholar 

  • Volkman JK (2003) Sterols in microorganisms. Appl Microbiol Biotechnol 60:495–506

    Article  PubMed  CAS  Google Scholar 

  • Volkman JK, Brown MR (2005) Nutritional value of microalgae and applications. In: Subba Rao DV (ed) Algal cultures, analogues of blooms and applications, vol 1. Science Publishers, Enfield, pp 407–457

    Google Scholar 

  • Volkman JK (2014) Acyclic isoprenoid biomarkers and evolution of biosynthetic pathways in green microalgae of the genus Botryococcus. Org Geochem 75:36–47

    Article  CAS  Google Scholar 

  • Volkman JK (2016) Sterols in microalgae. In: Borowitzka M, Beardall J, Raven JA (eds) The physiology of microalgae, Developments in applied phycology series 6. Springer, Cham, pp 485–505

    Chapter  Google Scholar 

  • Wang HT, Yao CH, Liu YN, Meng YY, Wang WL, Cao XP, Xue S (2015) Identification of fatty acid biomarkers for quantification of neutral lipids in marine microalgae Isochrysis zhangjiangensis. J Appl Phycol 27:249–255

    Article  CAS  Google Scholar 

  • Weete JD (1976) Algal and fungal waxes. In: Kolattukudy PE (ed) Chemistry and biochemistry of natural waxes. Elsevier, Amsterdam, pp 349–418

    Google Scholar 

  • Wraige EJ, Belt ST, Lewis CA, Cooke DA, Robert J-M, Massé G, Rowland SJ (1997) Variations in structures and distributions of C25 highly branched isoprenoid (HBI) alkenes in cultures of the diatom, Haslea ostrearia (Simonsen). Org Geochem 27:497–505

    Google Scholar 

  • Xu L, Reddy CM, Farrington JW, Frysinger GS, Gaines RB, Johnson CG, Nelson RK, Eglinton TI (2001) Identification of a novel alkenone in Black Sea sediments. Org Geochem 32:633–645

    Article  CAS  Google Scholar 

  • Xu ZB, Yan XJ, Pei LQ, Luo QJ, Xu JL (2008) Changes in fatty acids and sterols during batch growth of Pavlova viridis in photobioreactor. J Appl Phycol 20:237–243

    Article  CAS  Google Scholar 

  • Yon DA, Maxwell JR, Ryback G (1982) 2,6,10-Trimethyl-7-(3-methylbutyl)-dodecane, a novel sedimentary biological marker compound. Tetrahedron Lett 23:2143–2146

    Article  CAS  Google Scholar 

  • Zabeti N, Bonin P, Volkman JK, Jameson ID, Guasco S, Rontani J-F (2010) Potential alteration of \( {U}_{37}^{K^{\prime }} \) paleothermometer due to selective degradation of alkenones by marine bacteria isolated from the haptophyte Emiliania huxleyi. FEMS Microbiol Ecol 73:83–94

    PubMed  CAS  Google Scholar 

  • Zhao JJ, An CB, Longo WM, Dillon JT, Zhao YT, Shi C, Chen YF, Huang Y (2014) Occurrence of extended chain length C41 and C42 alkenones in hypersaline lakes. Org Geochem 75:48–53

    Article  CAS  Google Scholar 

  • Zhang YD, Su YL, Liu ZW, Chen XC, Yu JL, Di XD, Jin M (2015) Long-chain n-alkenes in recent sediment of Lake Lugu (SW China) and their ecological implications. Limnologica 52:30–40

    Article  CAS  Google Scholar 

  • Zhang ZR, Volkman JK (2017) Algaenan structure in the microalga Nannochloropsis oculata characterized by stepwise pyrolysis. Org Geochem 104:1–7

    Article  CAS  Google Scholar 

  • Zheng YS, Dillon JT, Zhang YF, Huang YS (2016) Discovery of alkenones with variable methylene-interrupted double bonds: implications for the biosynthetic pathway. J Phycol 52:1037–1050

    Article  PubMed  CAS  Google Scholar 

  • Zheng YS, Tarozo R, Huang YS (2017) Optimizing chromatographic resolution for simultaneous quantification of long chain alkenones, alkenoates and their double bond positional isomers. Org Geochem 111:136–143

    Article  CAS  Google Scholar 

  • Zink K-G, Leythaeuser D, Melkonian M, Schwark L (2001) Temperature dependency of long-chain alkenone distributions in recent to fossil limnic sediments and in lake waters. Geochim Cosmochim Acta 65:253–265

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to John K. Volkman .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2018 Springer International Publishing AG, part of Springer Nature

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Volkman, J.K. (2018). Lipids of Geochemical Interest in Microalgae. In: Wilkes, H. (eds) Hydrocarbons, Oils and Lipids: Diversity, Origin, Chemistry and Fate. Handbook of Hydrocarbon and Lipid Microbiology . Springer, Cham. https://doi.org/10.1007/978-3-319-54529-5_10-1

Download citation

  • DOI: https://doi.org/10.1007/978-3-319-54529-5_10-1

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, Cham

  • Print ISBN: 978-3-319-54529-5

  • Online ISBN: 978-3-319-54529-5

  • eBook Packages: Springer Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences

Publish with us

Policies and ethics