SpringerLink
Log in

Biomacromolecules of Algae and Plants and their Fossil Analogues

  • Published:
Plant Ecology Aims and scope Submit manuscript

Abstract

A review of our current understanding of resistant biomacromolecules derived from present and past algae and higher plants is presented. Insight in the nature of recent and fossil macromolecules is strongly hampered by the difficulties in obtaining the material in pure and unaltered form. For the extant material, avoiding artificial condensation and structural alteration as a result of chemical isolation and purification of biomacromolecules requires constant attention. To date, several types of sporopollenin seem to occur. One type is characterised by oxygenated aromatic building blocks, in particular p-coumaric acid and ferrulic acid. The other type is thought to consist predominantly of an aliphatic biopolymer. In this review it is concluded that extant sporopollenin consists of the aromatic type, whereas the aliphatic component of fossil sporopollenin is due to early-diagenetic oxidative polymerization of unsaturated lipids. The cuticles of most higher plants contain the aliphatic biopolyester cutin. Additionally, cuticles of drought-adapted, mostly CAM plants, seem to contain the non-hydrolysable aliphatic biopolymer cutan. Only a very few algae are able to biosynthesize resistant, (fossilisable) cell walls: some Chlorophyta, Eustigmatophyta and Prasinophyta produce the aliphatic biopolymer algaenan. Some Dinophyta are also capable of producing algaenan cell walls. Additionally, some taxa produce highly resistant cyst-walls with a high proportion of aromatic moieties. For the morphologically well-preserved fossil material, contamination by organic particles other than the target taxon is hard to eliminate and can contribute to either the aliphatic or aromatic signal. Furthermore, post-mortem migration of aliphatic moieties into, and their condensation onto the macromolecule might occur, e.g. by oxidative polymerization. These phenomena hamper the evaluation of the aliphatic signature of fossil plant material and may for example explain the preservation of initially cutin-based cuticles or non-algaenan containing algae. The extent to which migration and in situ formation of aromatic moieties plays a role in modifying resistant algal macromolecules, notably under elevated temperature and/or pressure conditions, still remains an open question.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • M.E. Aken R.N. Pienaar (1985) ArticleTitlePreliminary investigations on the chemical composition of the scale-boundary and cyst wall of Pyramimonas pseudoparkeae (Prasinophyceae) S. Afr. J. Bot. 51 408–416 Occurrence Handle1:CAS:528:DyaL28Xls1ymurk%3D

    CAS  Google Scholar 

  • B. Allard J. Templier (2000) ArticleTitleComparison of neutral lipid profile of various trilaminar outer cell wall (TLS)-containing microalgae with emphasis on algaenan occurrence Phytochemistry 54 369–380 Occurrence Handle10897477 Occurrence Handle1:CAS:528:DC%2BD3cXkslOgtb4%3D

    PubMed  CAS  Google Scholar 

  • B. Allard J. Templier (2001) ArticleTitleHigh molecular weight lipids from the trilaminar outer wall (TLS)-containing microalgae Chlorella emersonii, Scenedesmus communis and Tetraedron minimum Phytochemistry 57 459–467 Occurrence Handle11393527 Occurrence Handle1:CAS:528:DC%2BD3MXjtFCms7g%3D

    PubMed  CAS  Google Scholar 

  • B. Allard J. Templier C. Largeau (1998) ArticleTitleAn improved method for the isolation of artifact-free algaenans from microalgae Org. Geochem. 28 543–548 Occurrence Handle1:CAS:528:DyaK1cXktlWru7w%3D

    CAS  Google Scholar 

  • K. Arouri P.F. Greenwood M.R. Walter (1999) ArticleTitleA possible chlorophycean affinity of some Neoproterozoic acritarchs Org. Geochem. 30 1323–1337 Occurrence Handle1:CAS:528:DyaK1MXnvVyrtbk%3D

    CAS  Google Scholar 

  • K.R. Arouri P.F. Greenwood M.R. Walter (2000) ArticleTitleBiological affinities of Neoproterozoic acritarchs from Australia: microscopic and chemical characterisation Org. Geochem. 31 75–89 Occurrence Handle1:CAS:528:DC%2BD3cXhtF2rtLk%3D

    CAS  Google Scholar 

  • M. Ashraf M.B.E. Godward (1980) ArticleTitleUltrastructure and chemistry of the zygospore wall of Spirogyra Ann. Bot. 46 485–487 Occurrence Handle1:CAS:528:DyaL3MXmtFKrtg%3D%3D

    CAS  Google Scholar 

  • A.W. Atkinson SuffixJr B.E.S. Gunning P.C.L. John (1972) ArticleTitleSporopollenin in the cell wall of Chlorella and other algae: ultrastructure, chemistry and incorporation of 14C-acetate, studied in synchronous cultures Planta 107 1–32 Occurrence Handle1:CAS:528:DyaE38XltFWmsLo%3D

    CAS  Google Scholar 

  • D.J. Batten (1996) Green and blue-green algae. Colonial Chlorococcales J. Jansonius D.C. McGregor (Eds) Palynolog: Principles and Applications AASP Foundation Salt Lake City 191–203

    Google Scholar 

  • D.J. Batten H.R. Grenfell (1996) Green and blue-green algae. Botryococcus J. Jansonius D.C. McGregor (Eds) Palynology: Principles and Applications AASP Foundation Salt Lake City 205–214

    Google Scholar 

  • C. Berkaloff E. Casadevall C. Largeau P. Metzger S. Peracca J. Virlet (1983) ArticleTitleThe resistant polymer of the walls of the hydrocarbon-rich alga Botryococcus braunii Phytochemistry 22 389–397 Occurrence Handle1:CAS:528:DyaL3sXlslant7w%3D

    CAS  Google Scholar 

  • P.F. Bergen Particlevan (1994) Palaeobotany of Propagules: An Investigation combining Microscopy and Chemistry. Ph.D. Thesis University of London London

    Google Scholar 

  • P.F. Bergen Particlevan P. Blokker M.E. Collinson J.S. Sinninghe Damsté J.W. Leeuw Particlede (2004) Structural biomacromolecules in plants. What can be learnt from the fossil record? A.R. Hemsley I. Poole (Eds) Evolution of Plant Physiology Elsevier Amsterdam 133–154

    Google Scholar 

  • van Bergen P.F., Collinson M.E., Blokker P., Van Moerkerken P., Barrie P.J. and de Leeuw J.W. Chemical characterization of (fossil) sporopollenin: a molecular comparison of Azolla microspore massulae and Kurtzipites pollen with a review of previous literature, in press

  • P.F. Bergen Particlevan M.E. Collinson D.E.G. Briggs J.W. Leeuw Particlede A.C. Scott R.P. Evershed P. Finch (1995) ArticleTitleResistant biomacromolecules in the fossil record Acta Bot. Neerl. 44 319–345

    Google Scholar 

  • P.F. Bergen Particlevan M.E. Collinson J.W. Leeuw Particlede (1993) ArticleTitleChemical composition and ultrastructure of fossil and extant salvinialean microspore massulae and megaspores Grana Suppl. 1 18–30

    Google Scholar 

  • O. Bertheas P. Metzger C. Largeau (1999) ArticleTitleA high molecular weight complex lipid, aliphatic polyaldehyde tetraterpenediol polyacetal from Botryococcus braunii (L. race) Phytochem. 50 85–96 Occurrence Handle1:CAS:528:DyaK1MXjvVKnuw%3D%3D

    CAS  Google Scholar 

  • S. Biedlingmaier G. Wanner A. Schmidt (1987) ArticleTitleA correlation between detergent tolerance and cell wall structure in green algae Z. Naturforsch. 42 245–250 Occurrence Handle1:CAS:528:DyaL2sXktF2jt7o%3D

    CAS  Google Scholar 

  • B.J. Binder D.M. Anderson (1990) ArticleTitleBiochemical composition and metabolic activity of Scripsiella trochoidea (Dinophyceae) resting cysts J. Phycol. 26 289–298 Occurrence Handle1:CAS:528:DyaK3MXhs1Sms7k%3D

    CAS  Google Scholar 

  • P. Blokker (2000) ArticleTitleStructural analysis of resistant polymers in extant algae and ancient sediments Geol. Ultratrajectina 193 1–145

    Google Scholar 

  • P. Blokker S. Schouten J.W. Leeuw Particlede J.S. Sinninghe Damsté H. Ende Particlevan den (1999) ArticleTitleMolecular structure of the resistant biopolymer in the zygospore cell walls of Chlamydomonas monoica Planta 207 539–543 Occurrence Handle1:CAS:528:DyaK1MXhslKis70%3D

    CAS  Google Scholar 

  • P. Blokker S. Schouten J.W. Leeuw Particlede J.S. Sinninghe Damsté H. Ende Particlevan den (2000) ArticleTitleA comparitive study of fossil and extant algaenans using ruthenium tetroxide degradation Geochim. Cosmochim. Acta 64 2055–2065 Occurrence Handle1:CAS:528:DC%2BD3cXjvFGqt78%3D

    CAS  Google Scholar 

  • P. Blokker S. Schouten H. Ende Particlevan den J.W. Leeuw Particlede P.G. Hatcher J.S. Sinninghe Damsté (1998a) ArticleTitleChemical structure of algaenans from the fresh water algae Tetraedron minimum, Scenedesmus communis and Pediastrum boryanum Org. Geochem. 29 1453–1468 Occurrence Handle1:CAS:528:DyaK1MXpvVWnug%3D%3D

    CAS  Google Scholar 

  • P. Blokker S. Schouten H. Ende Particlevan den J.W. Leeuw Particlede J.S. Sinninghe Damsté (1998b) ArticleTitleCell wall specific ω-hydroxy fatty acids in freshwater green microalgae Phytochem. 49 691–695 Occurrence Handle1:CAS:528:DyaK1cXmsF2qtb0%3D

    CAS  Google Scholar 

  • P. Blokker P. Bergen Particlevan R. Pancost M.E. Collinson J.W. Leeuw Particlede J.S. Sinninghe Damsté (2001) ArticleTitleThe chemical structure of Gloeocapsamorpha prisca microfossils: Implications for their origin Geochim. Cosmochim. Acta 65 885–900 Occurrence Handle1:CAS:528:DC%2BD3MXhslemsrk%3D

    CAS  Google Scholar 

  • A.V. Blom (1936) ArticleTitleQuelques remarques sur le mécanisme de séchage des peintures à l'huile Peintures, Pigments, Vernis 13 156–162 Occurrence Handle1:CAS:528:DyaA2sXjvF2qsg%3D%3D

    CAS  Google Scholar 

  • A. Boom (2004) A Geochemical Study of Lacustrine Sediments: Towards Palao-climatic Econstructions of High Andean Biomes in Colombia University of Amsterdam Amsterdam 125

    Google Scholar 

  • Boom A., Sinninghe Damsté J.S. and de Leeuw J.W. 2005. Cutan, a common aliphatic biopolymer in cuticles of drought-adapted plants. Org. Geochem. 36: 596–601

  • D.E.G. Briggs A.J. Kear M. Baas J.W. Leeuw Particlede S. Rigby (1995) ArticleTitleDecay and composition of the hemichordate Rhabdopleura: implications for the taphonomy of graptolites Lethaia 28 15–23

    Google Scholar 

  • U. Brunner R. Honegger (1985) ArticleTitleChemical and ultrastructural studies on the distribution of sporopollenin like biopolymers in six genera of lichen phycobionts Can. J. Bot. 63 2221–2230 Occurrence Handle1:CAS:528:DyaL28XhsVGhsr8%3D

    CAS  Google Scholar 

  • J. Burczyk (1987a) ArticleTitleBiogenic relationships between ketocarotenoids and sporopollenins in green algae Phytochemistry 26 113–119

    Google Scholar 

  • J. Burczyk (1987b) ArticleTitleCell wall carotenoids in green algae which form sporopollenins Phytochemistry 26 121–128

    Google Scholar 

  • J. Burczyk B. Šmietana K. Terminska-Pabis M. Zych P. Kowalowski (1999) ArticleTitleComparison of nitrogen content amino acid composition and glucosamine content of cell walls of various chlorococcalean algae Phytochemistry 51 491–497 Occurrence Handle1:CAS:528:DyaK1MXktVCjs78%3D

    CAS  Google Scholar 

  • N.J. Butterfield R.H. Rainbird (1998) ArticleTitleDiverse organic-walled fossils, including 'possible dinoflagellates' from the early Neoproterozoic of arctic Canada Geology 26 963–966

    Google Scholar 

  • M.E. Collinson B. Mösle P. Finch A.C. Scott R. Wilson (1998) ArticleTitleStructure, biosynthesis and biodegradation of cutin and suberin Ancient Biomol. 2 251–265 Occurrence Handle1:CAS:528:DyaK1MXmsFequrw%3D

    CAS  Google Scholar 

  • M.E. Collinson P.F. Bergen Particlevan (2004) Evolution of angiosperm fruit and seed physiology: anatomical and chemical evidence from fossils A.R. Hemsley I. Poole (Eds) Evolution of Plant Physiology Elsevier Amsterdam 343–377

    Google Scholar 

  • M.E. Collinson P.F. Bergen Particlevan A.C. Scott J.W. Leeuw Particlede (1994) ArticleTitleThe oil-generating potential of plants from coal and coal-bearing strata through time: a review with new evidence from Carboniferous plants Geol. Soc. Spec. Publ. 77 31–70

    Google Scholar 

  • A. Combaz (1971) Themal degradation of sporopollenin and genesis of hydrocarbons J. Brooks (Eds) et al. Sporopollenin Academic Press London 621–653

    Google Scholar 

  • G. Corre J. Templier C. Largeau B. Rousseau C. Berkaloff (1996) ArticleTitleInfluence of cell wall composition on the resistance of two Chlorella species (Chlorophyta) to detergents J. Phycol. 32 584–590 Occurrence Handle1:CAS:528:DyaK28XlvVWisbo%3D

    CAS  Google Scholar 

  • B. Dale (1976) ArticleTitleCyst formation, sedimentation, and preservation: factors affecting dinoflagellate assemblages in recent sediments from Trondheimsfjord Norway. Rev. Palaeobot. Palynol. 22 39–60

    Google Scholar 

  • Dammers N. 2003. Chemical characterization of the organic-walled dinoflagellate cyst taxa Nematosphaeropsis labyrinthus, Polysphaeridium zoharii, Brigantedinium spp. and Palaeoperidinium spp. and a review on algaenan and dinosterol. Masters Thesis, Department of Geochemistry, Utrecht University, 43 pp

  • J.W. Leeuw Particlede C. Largeau (1993) A review of macromolecular compounds that comprise living organisms and their role in kerogen, coal and petroleum formation M.H. Engel S.A. Macko (Eds) Organic Geochemistry. Principles and Applications Plenum Press New York 23–72

    Google Scholar 

  • P.J.R. Vries Particlede J. Simons A.P. Beem Particlevan (1983) ArticleTitleSporopollenin in the spore wall of Spirogyra (Zygnemataceae, Chlorophyceae) Acta Bot. Neerl. 32 252–258

    Google Scholar 

  • S. Derenne C. Largeau F. Behar (1994) ArticleTitleLow polarity pyrolysis products of Permian to Recent Botryoccus-rich sediments: first evidence for the contribution of an isoprenoid algaenan to kerogen formation Geochim. Cosmochim. Acta 58 3703–3711 Occurrence Handle1:CAS:528:DyaK2cXmtVylsrY%3D

    CAS  Google Scholar 

  • S. Derenne C. Largeau C. Berkaloff (1996) ArticleTitleFirst example of an algaenan yielding an aromatic-rich pyrolysate. Possible geochemical implications on marine kerogen formation Org. Geochem. 24 617–627 Occurrence Handle1:CAS:528:DyaK28Xms1Ogsbw%3D

    CAS  Google Scholar 

  • S. Derenne C. Largeau C. Berkaloff B. Rousseau C. Wilhelm P.G. Hatcher (1992a) ArticleTitleNon-hydrolysable macromolecular constituents from outer walls of Chlorella fusca and Nanochlorum eucaryotum Phytochemistry 31 1923–1929 Occurrence Handle1:CAS:528:DyaK38Xks1Kiu7o%3D

    CAS  Google Scholar 

  • S. Derenne C. Largeau E. Casadevall C. Berkaloff B. Rousseau (1991) ArticleTitleChemical 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 55 1041–1050 Occurrence Handle1:CAS:528:DyaK3M**tlaht74%3D

    CAS  Google Scholar 

  • S. Derenne C. Largeau M. Hetényi A. Brukner-Wein J. Conan B. Lugardon (1997) ArticleTitleChemical structure of the organic matter in a Pliocene maar-type shale: implicated Botryococcus race strains and formation pathways Geochim. Cosmochim. Acta 61 1879–1889 Occurrence Handle1:CAS:528:DyaK2sXjtl2qtL8%3D

    CAS  Google Scholar 

  • S. Derenne P. Metzger C. Largeau P.F. Bergen Particlevan J.P. Gatellier J.S. Sinninghe Damsté J.W. Leeuw Particlede C. Berkaloff (1992) ArticleTitleSimilar morphological and chemical variations of Gloeocapsomorpha prisca in Ordovician sediments and cultured Botryococcus braunii as a response to changes in salinity Org. Geochem. 19 299–313 Occurrence Handle1:CAS:528:DyaK3sXktFWktbk%3D

    CAS  Google Scholar 

  • A. P. Deshmukh A.J. Simpson P.G. Hatcher (1964) ArticleTitleEvidence for cross-linking in tomato cutin using HR-MAS NMR spectroscopy Phytochemistry 64 1163–1170

    Google Scholar 

  • E. Domínguez J.A. Mercado M.A. Quesada A. Heredia (1999) ArticleTitlePollen sporopollenin: degradation and structural elucidation Sex. Plant Reprod. 12 171–178

    Google Scholar 

  • R.A. Fensome et al. (1993) A Classification of Modern and Fossil Dinoflagellates Sheridan Press Hanover 351

    Google Scholar 

  • R.A. Fensome J.F. Saldarriaga F.J.R. Taylor (1999) ArticleTitleDinoflagellate phylogeny revisited: reconciling morphological and molecular based phylogenies Grana 38 66–80

    Google Scholar 

  • P. Fjällström B. Andersson C. Nilsson K. Andersson (2002) ArticleTitleDrying of linseed oil paints: a laboratory study of aldehyde emissions Indust. Crop. Prod. 16 173–184

    Google Scholar 

  • C.B. Foster M.H. Stephenson C. Marshall G.A. Logan P.F. Greenwood (2002) ArticleTitleA revision of Reduviasporonites Wilson 1962: description, illustration, comparison and biological affinities Palynology 26 35–58

    Google Scholar 

  • N.I. Gabarayeva S. Blackmore J.R. Rowley (2003) ArticleTitleObservations on the experimental destruction and substructural organisation of the pollen wall of some selected Gymnosperms and Angiosperms Rev. Palaeobot. Palynol. 124 203–226

    Google Scholar 

  • B. Geel Particlevan H.R. Grenfell (1996) Green and blue-green algae. Spores of Zygnemataceae J. Jansonius D.C. McGregor (Eds) Palynology: Principles and Applications AASP Foundation Salt Lake City 173–179

    Google Scholar 

  • F. Gelin I. Boogers A.A.M. Noordeloos J.S. Sinninghe Damsté R. Riegman J.W. Leeuw Particlede (1997) ArticleTitleResistant biomacromolecules in marine microalgae of the classes Eustigmatophyceae and Chlorophyceae: Geochemical applications Org. Geochem. 26 659–675 Occurrence Handle1:CAS:528:DyaK1cXhs1SmsA%3D%3D

    CAS  Google Scholar 

  • F. Gelin J.K. Volkman C. Largeau S. Derenne J.S. Sinninghe Damsté J.W. Leeuw Particlede (1999) ArticleTitleDistribution of aliphatic nonhydrolyzable biopolymers in marine microalgae Org. Geochem. 30 147–159 Occurrence Handle1:CAS:528:DyaK1M**tVaksL4%3D

    CAS  Google Scholar 

  • B.H. Good R.L. Chapman (1978) ArticleTitleThe ultrastructure of Phycopeltis (Chroolepidaceae: Chlorophyta). I. Sporopollenin in the cell walls Am. J. Bot. 65 27–33 Occurrence Handle1:CAS:528:DyaE1cXhtVWgsrc%3D

    CAS  Google Scholar 

  • K. Goth J.W. Leeuw Particlede W. Püttmann E.W. Tegelaar (1988) ArticleTitleOrigin of messel oil shale kerogen Nature 336 759–761 Occurrence Handle1:CAS:528:DyaL1MXnvV2mtw%3D%3D

    CAS  Google Scholar 

  • J. Gray A.J. Boucot (1989) ArticleTitleIs Moyeria a euglenoid? Lethaia 22 447–456

    Google Scholar 

  • P.F. Greenwood K.R. Arouri S.C. George (2000) ArticleTitleTricyclic terpenoid composition of Tasmanites kerogen as determined by pyrolysis GC-MS Geochim. Cosmochim. Acta 64 1249–1263 Occurrence Handle1:CAS:528:DC%2BD3cXhvF2ltrc%3D

    CAS  Google Scholar 

  • W.J. Guilford D.M. Schneider J. Labovitz S.J. Opella (1988) ArticleTitleHigh resolution solid state 13C NMR spectroscopy of sporopollenin from different plant taxa Plant Physiol. 86 134–136 Occurrence Handle16665854 Occurrence Handle1:CAS:528:DyaL1cXht1ymsbo%3D

    PubMed  CAS  Google Scholar 

  • D. Gunnison M. Alexander (1975) ArticleTitleBasis for the resistance of several algae to microbial decomposition Appl. Microbiol. 29 729–738 Occurrence Handle808166 Occurrence Handle1:CAS:528:DyaE2MXkvFektb0%3D

    PubMed  CAS  Google Scholar 

  • D. Guy-Ohlson (1996) Green and blue-green algae. Prasinophyceanalgae J. Jansonius D.C. McGregor (Eds) Palynology: Principles and Applications AASP Foundation Salt Lake City 181–189

    Google Scholar 

  • W.A. Hartgers J.S. Sinninghe Damsté J.W. Leeuw Particlede (1995) ArticleTitleCurie-point pyrolysis of sodium salts of functionalized fatty acids J. Anal. Appl. Pyrolysis 34 191–217 Occurrence Handle1:CAS:528:DyaK2MXnt1Kqsbk%3D

    CAS  Google Scholar 

  • R. Hayatsu R.E. Botto R.L. Mcbeth R.G. Scott R.E. Winans (1988) ArticleTitleChemical alteration of a biological polymer 'sporopollenin' during coalification: origin, formation, and transformation of the coal maceral sporinite Energy Fuel 2 843–847 Occurrence Handle1:CAS:528:DyaL1cXlvFentr8%3D

    CAS  Google Scholar 

  • E. Hegewald T.R. Deason (1988) ArticleTitlePseudoschroederia punctata (Chlorophyta, Chlorococcales), a new species with an unusual cell wall Arch. Hydrobiol. Suppl. 78 465–473

    Google Scholar 

  • E. Hegewald T.R. Deason (1989) ArticleTitlePseudodidymocystis, a new genus of Scenedesmaceae (Chlorophyceae) Arch. Hydrobiol. Suppl. 82 119–127

    Google Scholar 

  • A.R. Hemsley P.J. Barrie W.G. Chaloner A.C. Scott (1993) ArticleTitleThe composition of sporopollenin and its use in living and fossil plant systematics Grana Suppl. 1 2–11

    Google Scholar 

  • A.R. Hemsley P.J. Barrie W.G. Chaloner (1994) ArticleTitleStudies of fossil and modern spore and pollen wall biomacromolecules using 13C solid state NMR NERC Spec. Publ. 94 15–19

    Google Scholar 

  • P.J. Holloway (1982) The chemical constitution of plant cutins D.F. Cutler (Eds) et al. The Plant Cuticle Elsevier Amsterdam 45–85

    Google Scholar 

  • R. Honegger U. Brunner (1981) ArticleTitleSporopollenin in the cell walls of Coccomyxa and Myrmecia phycobionts of various lichens: an ultrastructural and chemical investigation Can. J. Bot. 59 2713–2734 Occurrence Handle1:CAS:528:DyaL38XhtF2jt78%3D

    CAS  Google Scholar 

  • J.A. Hopkins F.M.G. McCarthy (2002) ArticleTitlePost-depositional palynomorph degradation in Quaternary shelf sediments: a laboratory experiment studying the effects of progressive oxidation Palynology 26 167–184

    Google Scholar 

  • H.M. Hull R.W. Hoshaw J.-C. Wang (1985) ArticleTitleInterpretation of zygospore wall structure and taxonomy of Spirogyra and Sirogonium (Zygnemataceae, Chlorophyta) Phycologia 24 231–239

    Google Scholar 

  • V.A.R. Huss C. Frank E.C. Hartmann M. Hirmer A. Kloboucek B.M. Seidel P. Wenzeler E. Kessler (1999) ArticleTitleBiochemical taxonomy and molecular phylogeny of the genus Chlorella sensu lato (Chlorophyta) J. Phycol. 35 587–598 Occurrence Handle1:CAS:528:DyaK1MXksl2hsrY%3D

    CAS  Google Scholar 

  • E. Javaux A.H. Knoll M. Walter (2003) ArticleTitleRecognizing and interpreting the fossils of early eukaryotes Origin. Life Evol. Biosph. 33 75–94 Occurrence Handle1:CAS:528:DC%2BD3sXktVKns7s%3D

    CAS  Google Scholar 

  • A. Kadouri S. Derenne C. Largeau E. Casadevall C. Berkaloff (1988) ArticleTitleResistant biopolymer in the outer walls of Botryococcus braunii, B race Phytochemistry 27 551–557 Occurrence Handle1:CAS:528:DyaL1cXhsVKrs7s%3D

    CAS  Google Scholar 

  • G. Kjellström (1968) ArticleTitleRemarks on the chemistry and ultrastructure of the cell wall of some Palaeozoic leiospheres Geol. Föreningens Stockholm Förhandl. 90 221–228

    Google Scholar 

  • A.H. Knoll (1992) ArticleTitleThe early evolution of eukaryotes: a geological perspective Science 256 622–627 Occurrence Handle1585174 Occurrence Handle1:STN:280:By2B28zgvFY%3D

    PubMed  CAS  Google Scholar 

  • A.H. Knoll (1996) Archean and Proterozoic paleontology J. Jansonius D.C. McGregor (Eds) Palynology: Principles and Applications AASP Foundation Salt Lake City 51–80

    Google Scholar 

  • J.P. Kokinos T.I. Eglinton M.A. Goñi J.J. Boon P.A. Martoglio D.M. Anderson (1998) ArticleTitleCharacterisation of a highly resistant biomacromolecular material in the cell wall of a marine dinoflagellate resting cyst Org. Geochem. 28 265–288 Occurrence Handle1:CAS:528:DyaK1cXjtFeitb4%3D

    CAS  Google Scholar 

  • P.E. Kolattukudy (1981) ArticleTitleStructure, biosynthesis and biodegradation of cutin and suberin Ann. Rev. Plant Physiol 32 539–576 Occurrence Handle1:CAS:528:DyaL3MXkt1Whsbo%3D

    CAS  Google Scholar 

  • J. König E. Peveling (1980) ArticleTitleVorkommen von sporopollenin in der zellwand des phycobionten Trebouxia Z. Pflanzenphysiol. 98 459–464

    Google Scholar 

  • J. König E. Peveling (1984) ArticleTitleCell walls of the phycobionts Trebouxia and Pseudotrebouxia: constituents and their localisation Lichenology 16 129–144

    Google Scholar 

  • A. Kozubek J.H.P. Tyman (1999) ArticleTitleResorcinolic lipids, the natural non-isoprenic amphiphiles and their biological activity Chem. Rev. 99 1–26 Occurrence Handle11848979 Occurrence Handle1:CAS:528:DyaK1cXotFaju74%3D

    PubMed  CAS  Google Scholar 

  • M.M.M. Kuypers P. Blokker E.C. Hopmans H. Kinkel R.D. Pancost S. Schouten J.S. Sinninghe Damsté (2002) ArticleTitleArchaeal remains dominate marine organic matter from the early Albian oceanic anoxic event 1b Palaeogeogr. Palaeoclimatol. Palaeoecol. 185 211–234

    Google Scholar 

  • U. Leppig M. Montenari (2000) ArticleTitleOrganic-walled microfossils of possible dinoflagellate affinity from the Lower Permian of Sonora (northwest Mexico) Mar. Micropaleontol. 40 1–8

    Google Scholar 

  • J. Lewis A.S.D. Harris K.J. Jones R.L. Edmonds (1999) ArticleTitleLong-term survival of marine planktonic diatoms and dinoflagellates in stored sediment samples J. Plankton Res. 21 343–354

    Google Scholar 

  • Ü. Lille (2003) ArticleTitleCurrent knowledge on the origin and structure of Estonian Kukersite kerogen Oil Shale 20 253–263 Occurrence Handle1:CAS:528:DC%2BD3sXotFyrs74%3D

    CAS  Google Scholar 

  • H.J. Marchant (1977) ArticleTitleCell division and colony formation in the green alga Coelastrum (Chlorococcales) J. Phycol. 13 102–110

    Google Scholar 

  • F. Marret (1993) ArticleTitleLes effets de l'acétolyse sur les assemblages des kystes de dinoflagellés Palynoscience 2 267–272

    Google Scholar 

  • D.E. McKinney J.M. Bortiatynski D.M. Carson D.J. Clifford J.W. Leeuw Particlede P.G. Hatcher (1996) ArticleTitleTetramethylammonium hydroxide (TMAH) thermochemolysis of the aliphatic biopolymer cutan: insights into the chemical structure Org. Geochem. 24 641–650 Occurrence Handle1:CAS:528:DyaK28Xms1Ogtr0%3D

    CAS  Google Scholar 

  • P. Metzger C. Largeau (1994) ArticleTitleA new type of ether lipid comprising phenolic moieties in Botryococcus braunii. Chemical structure and abundance, and geochemical implications Org. Geochem. 22 801–814 Occurrence Handle1:CAS:528:DyaK2MXktVGgsro%3D

    CAS  Google Scholar 

  • P. Metzger C. Largeau (2002) Natural polyacetals S. Matsumura A. Steinbüchel (Eds) Miscellaneous Biopolymers and Biodegradation of Synthetic Polymers Wiley-VCH Weinheim 113–127

    Google Scholar 

  • J.M. Moldowan J. Dahl S.R. Jacobson B.J. Huizinga F.J. Fago R. Shetty D.S. Watt K.E. Peters (1996) ArticleTitleChemostratigraphic reconstruction of biofacies: molecular evidence linking cyst-forming dinoflagellates with pre-Triassic ancestors Geology 24 159–162

    Google Scholar 

  • A. Montsant A. Zarka S. Boussiba (2001) ArticleTitlePresence of a nonhydrolysable biopolymer in the cell wall of vegetative cells and astaxanthin-rich cysts of Haematococcus pluvialis (Chlorophyceae) Mar. Biotechnol. 3 515–521 Occurrence Handle14961323 Occurrence Handle1:CAS:528:DC%2BD38XotVWhsw%3D%3D

    PubMed  CAS  Google Scholar 

  • L.C. Morrill A.R. Loeblich SuffixIII (1981) ArticleTitleThe dinoflagellate pellicular wall layer and its occurrence in the division Pyrrophyta J. Phycol. 17 315–323

    Google Scholar 

  • van Mourik A. 2000. Chemical characterization of fossil palynomorphs; gonyaulacoid, peridinioid dinoflagellate cysts and sporomorphs. Masters Thesis Department of Geochemistry, Utrecht University, 49 pp

  • B. Mösle P. Finch M.E. Collinson A.C. Scott (1997) ArticleTitleComparison of modern and fossil plant cuticles by selective chemical extraction monitored by flash pyrolysis-gas chromatography-mass spectroscopy and electron microscopy J. Anal. Appl. Pyrolysis 40–41 585–597

    Google Scholar 

  • M.M. Mulder E.R.E. Hage Particlevan der J.J. Boon (1992) ArticleTitleAnalytical in source pyrolytic methylation electron impact mass spectrometry of phenolic acids in biological matrices Phytochem. Anal. 3 165–172 Occurrence Handle1:CAS:528:DyaK38XmtVyhu7o%3D

    CAS  Google Scholar 

  • P.J. Müller G. Kirst G. Ruhland I. Von Storch A. Rosell-Melé (1998) ArticleTitleCalibration of the alkenone paleotemperature index based on coretops from the eastern South Atlantic and global ocean (60°N-60°S) Geochim. Cosmochim. Acta 62 1757–1772

    Google Scholar 

  • R.A. Porcella P.L. Walne (1980) ArticleTitleMicroarchitecture and envelope development in Dysmorphococcus globosus (Phacotaceae, Chlorophyceae) J. Phycol. 16 280–290

    Google Scholar 

  • F. Puel C. Largeau G. Giraud (1987) ArticleTitleOccurrence of a resistant biopolymer in the outer walls of the parasitic alga Prototheca wickerhamii (Chlorococcales): ultrastructure and chemical studies J. Phycol. 23 649–656 Occurrence Handle1:CAS:528:DyaL1cXht1yitLk%3D

    CAS  Google Scholar 

  • N. Rascio G. Casadoro C. Andreoli (1979) ArticleTitleUltrastructural features of Chlorella nana sp. nov Bot. Mar. 22 223–227

    Google Scholar 

  • M.C. Rodríguez A.S. Cerezo (1996) ArticleTitleThe resistant 'biopolymer' in cell walls of Coelastrum sphaericum Phytochemistry 43 731–734

    Google Scholar 

  • M.C. Rodríguez M.D. Noseda A.S. Cerezo (1999) ArticleTitleThe fibrillar polysaccharides and their linkage to algaenan in the trilaminar layer of the cell wall of Coelastrum sphaericum (Chlorophyceae) J. Phycol. 35 1025–1031

    Google Scholar 

  • J. Rozema R.A. Broekman P. Blokker B.B. Meijkamp N. Bakker Particlede J. Staaij Particlevan de A. Beem Particlevan F. Ariese S.M. Kars (2001) ArticleTitleUV-B absorbance and UV-B absorbing compounds (para-cumaric acid) in pollen and sporopollenin: the perspective to track historic UV-B levels J. Photochem. Photobiol. 62 108–117 Occurrence Handle1:CAS:528:DC%2BD3MXns1eku74%3D

    CAS  Google Scholar 

  • J. Rozema B. Geel Particlevan L.O. Björn J. Lean S. Madronich (2002) ArticleTitleToward solving the UV puzzle Science 296 1621–1622 Occurrence Handle12040167 Occurrence Handle1:CAS:528:DC%2BD38XktlChsb0%3D

    PubMed  CAS  Google Scholar 

  • J. Rullkötter (1993) The thermal alteration of kerogen and the formation of oil M.H. Engel S.A. Macko (Eds) Organic Geochemistry. Principles and Applications Plenum Press New York 377–96

    Google Scholar 

  • W.A. Sarjeant (1978) ArticleTitleArpylorus antiquus Calandra, emend., a dinoflagellate cyst from the Upper Silurian Palynol. 2 167–179

    Google Scholar 

  • P.A. Schenck J.W. Leeuw Particlede G. Graas Particlevan J. Haverkamp M. Bouman (1981) Analysis of recent spores and pollen and of thermally altered sporopollenin by flash pyrolysis-mass spectrometry and flash pyrolysis-gas chromatography-mass spectrometry J. Brooks (Eds) Organic Maturation Studies and Fossil Fuel Exploration Academic Press London 225–237

    Google Scholar 

  • S. Schouten E.C. Hopmans E. Schefuss J.S. Sinninghe Damsté (2002) ArticleTitleDistributional variations in marine crenarchaeotal membrane lipids: a new tool for reconstructing ancient sea water temperatures? Earth Planet. Sci. Lett. 204 265–274 Occurrence Handle1:CAS:528:DC%2BD38XovFensb0%3D

    CAS  Google Scholar 

  • E. Schrank (1988) ArticleTitleEffects of chemical processing on the preservation of peridinioid dinoflagellates: a case from the late cretaceous of NE Africa Rev. Palaeobot. Palynol. 56 123–140

    Google Scholar 

  • G. Shaw (1971) The chemistry of sporopollenin J. Brooks (Eds) et al. Sporopollenin Academic Press London 305–350

    Google Scholar 

  • A.J. Simpson X. Zang R. Kramer P.G. Hatcher (2003) ArticleTitleNew insights on the structure of algaenan from Botryococcus braunii race A and its hexane insoluble botryals based on multidimensional NMR spectroscopy and electrospray-mass spectrometry techniques Phytochem. 62 783–796 Occurrence Handle1:CAS:528:DC%2BD3sXhs1Kisbo%3D

    CAS  Google Scholar 

  • J.S. Sinninghe Damsté F.X.C. Delas Heras P.F. Bergen Particlede J.W. Leeuw Particlede (1993) ArticleTitleCharacterization of tertiary catalan lacustrine oil shales: discovery of extremely organic sulphur-rich Type I kerogens Geochim. Cosmochim. Acta 57 389–415

    Google Scholar 

  • A. Srivastava R. Prasad (2000) ArticleTitleTriglycerides-based diesel fuels Renew. Sust. Energ. Rev. 4 111–133 Occurrence Handle1:CAS:528:DC%2BD3c**sVCks7o%3D

    CAS  Google Scholar 

  • L.A. Staehelin J.D. Picket-Heaps (1975) ArticleTitleThe ultrastructure of Scenedesmus (Chlorophyceae). I. Species with the 'reticulate' or 'warty' type of ornamental layer J. Phycol. 11 163–185

    Google Scholar 

  • B.A. Stankiewicz D.E.G. Briggs R. Michels M.E. Collinson M.B. Flannery R.P. Evershed (2000) ArticleTitleAlternative origin of aliphatic polymer kerogen Geology 28 559–562 Occurrence Handle1:CAS:528:DC%2BD3cXkt1GjtLk%3D

    CAS  Google Scholar 

  • P.K. Strother (1996) Acritarchs J. Jansonius D.C. McGregor (Eds) Palynology: principles and applications AASP Foundation Salt Lake City 81–106

    Google Scholar 

  • E. Swift C.C. Remsen (1970) ArticleTitleThe cell wall of Pyrocystis spp. (Dinophyceae) J. Phycol. 6 79–86

    Google Scholar 

  • P.J. Syrett E.M. Thomas (1973) ArticleTitleThe assay of nitrate reductase in whole cells of Chlorella: strain differences and the effect of cell walls New Phytol. 72 1307–1310 Occurrence Handle1:CAS:528:DyaE2cXjsV2mug%3D%3D

    CAS  Google Scholar 

  • N.M. Talyzina J.M. Moldowan A. Johannisson F.J. Fago (2000) ArticleTitleAffinities of Early Cambrian acritarchs studied by using microscopy, fluorescence flow cytometry and biomarkers Rev. Palaeobot. Palynol. 108 37–53

    Google Scholar 

  • E.W. Tegelaar J.W. Leeuw Particlede S. Derenne C. Largeau (1989) ArticleTitleA reappraisal of kerogen formation Geochim. Cosmochim. Acta 53 3103–3106 Occurrence Handle1:CAS:528:DyaK3cXjvFegsA%3D%3D

    CAS  Google Scholar 

  • E.W. Tegelaar H. Kerp H. Visscher P.A. Schenck J.W. Leeuw Particlede (1991) ArticleTitleBias of the paleobotanical record as a consequence of variations in the chemical composition of higher vascular plant cuticles Paleobiology 17 133–144

    Google Scholar 

  • L.H. Tiffany (1924) ArticleTitleA physiological study of growth and reproduction among certain algae Ohio J. Sci. 24 65–99

    Google Scholar 

  • J.-L. Turon (1984) ArticleTitleLe palynoplancton dans l'environnement actuel de l'Atlantique nord-oriental. Évolution climatique et hydrologique depuis le dernier maximum glaciaire Mem. Inst. Geol. Bassin Aquitaine 17 1–313

    Google Scholar 

  • G.J.M. Versteegh P. Blokker G. Wood M.E. Collinson J.S. Sinninghe Damsté J.W. Leeuw Particlede (2004) ArticleTitleOxidative polymerization of unsaturated fatty acids as a preservation pathway for microalgal organic matter Org. Geochem. 35 1129–1139 Occurrence Handle1:CAS:528:DC%2BD2cXnsVGjt78%3D

    CAS  Google Scholar 

  • G.J.M. Versteegh J.H.F. Jansen J.W. Leeuw Particlede R.R. Schneider (2000) ArticleTitleMid-chain diols and keto-ols in sediments. A new tool for tracing past sea surface water masses? Geochim. Cosmochim. Acta 64 1879–1892 Occurrence Handle1:CAS:528:DC%2BD3cXjs1SktLc%3D

    CAS  Google Scholar 

  • G.J.M. Versteegh K.A.F. Zonneveld (2002) ArticleTitleUse of selective degradation to separate preservation from productivity Geology 30 615–618 Occurrence Handle1:CAS:528:DC%2BD38XlvFWisro%3D

    CAS  Google Scholar 

  • Warnaar J. 2001. Chemical characterization of fossil organic walled dinoflagellate cysts. Masters Thesis, Department of Geochemistry, Utrecht University. 26 pp

  • K. Wehling C. Niester J.J. Boon M.T.M. Willemse R. Wiermann (1989) ArticleTitlep-Coumaric acid – a monomer in the sporopollenin skeleton Planta 179 376–380 Occurrence Handle1:CAS:528:DyaL1MXmt12jt7o%3D

    CAS  Google Scholar 

  • R. Wicander C.B. Foster J.D. Reed (1996) Green and blue-green algae. Gloeocapsomorpha J. Jansonius D.C. McGregor (Eds) Palynology: Principles and Applications AASP Foundation Salt Lake City 215–225

    Google Scholar 

  • M.E. Wurdack (1923) ArticleTitleChemical composition of the walls of certain algae Ohio J. Sci. 23 181–191 Occurrence Handle1:CAS:528:DyaB3s**sVGmsw%3D%3D

    CAS  Google Scholar 

  • B.L. Yule S. Roberts J.E.A. Marchall (2000) ArticleTitleThe thermal evolution of sporopollenin Org. Geochem. 31 859–870 Occurrence Handle1:CAS:528:DC%2BD3cXnt1yjtrY%3D

    CAS  Google Scholar 

  • V. Zárský T. Kalina J. Sulek (1985) ArticleTitleNotes on the sexual reproduction of Chlamydomonas geitleri Ettl Arch. Protistenk. 130 343–353

    Google Scholar 

  • J.L. Zelibor SuffixJr L. Romankiw P.G. Hatcher R.R. Colwell (1988) ArticleTitleComparitive analysis of the chemical composition of mixed and pure cultures of green algae and their decomposed residues by 13C nuclear magnetic resonance spectroscopy Appl. Env. Microbiol. 54 1051–1060 Occurrence Handle1:CAS:528:DyaL1cXktF2qtLo%3D

    CAS  Google Scholar 

  • E. Zhang P.G. Hatcher A. Davis (1993) ArticleTitleChemical composition of pseudo-phlobaphinite precursors: implications for the presence of aliphatic biopolymers in vitrinite from coal Org. Geochem. 20 721–734 Occurrence Handle1:CAS:528:DyaK2cXjsVWquw%3D%3D

    CAS  Google Scholar 

  • K.A.F. Zonneveld G.J.M. Versteegh Lange de J. G. (1997) ArticleTitlePreservation of organic walled dinoflagellate cysts in different oxygen regimes: a 10,000 years natural experiment Mar. Micropaleontol. 29 393–405

    Google Scholar 

  • K.A.F. Zonneveld G.J.M. Versteegh G.J. Lange Particlede (2001) ArticleTitlePalaeoproductivity and post-depositional aerobic organic matter decay reflected by dinoflagellate cyst assemblages of the Eastern Mediterranean S1 sapropel Mar. Geol. 172 181–195 Occurrence Handle1:CAS:528:DC%2BD3MXhtFSntLY%3D

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Royal Netherlands Institute for Sea Research, 1797 SZ 't Horntje, Texel, The Netherlands

    Jan W. de Leeuw & Gerard J. M. Versteegh

  2. Organic Geochemistry, Faculty of Geosciences, Utrecht University, Budapestlaan 4, 3584CD, Utrecht, The Netherlands

    Jan W. de Leeuw & Gerard J. M. Versteegh

  3. Palaeoecology, Faculty of Biology, Budapestlaan 4, 3584CD, Utrecht, The Netherlands

    Jan W. de Leeuw

  4. Hanse Wissenschaftskolleg, Lehmkuhlenbusch 4, 27753, Delmenhorst, Germany

    Gerard J. M. Versteegh

  5. Shell Global Solutions International, Badhuisweg 3, 1031 CM, Amsterdam, The Netherlands

    Pim F. van Bergen

Authors
  1. Jan W. de Leeuw
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Gerard J. M. Versteegh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pim F. van Bergen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jan W. de Leeuw.

Rights and permissions

Reprints and permissions

About this article

Cite this article

de Leeuw, J.W., Versteegh, G.J.M. & van Bergen, P.F. Biomacromolecules of Algae and Plants and their Fossil Analogues. Plant Ecol 182, 209–233 (2006). https://doi.org/10.1007/s11258-005-9027-x

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11258-005-9027-x

Keywords

Search

Navigation