Advertisement

Carotenoids

  • Einar Skarstad Egeland
Chapter
Part of the Developments in Applied Phycology book series (DAPH, volume 6)

Abstract

Carotenoids are essential for photosynthesis, and are therefore present in all organisms traditionally considered as algae. Around 200 different carotenoids has been encountered in algae, and the study of carotenoids is often used to determine the distribution of algae in ocean water.

The chapter gives a full overview of the various algal pigment groups, from the major ones as green algae down to rare pigment combinations that might be known only from a single to a few species. Extensive references are included for further study, together with figures presenting the molecular structure of the characteristic carotenoids, making it possible for the reader to see the structural diversity of carotenoids found in mostly planktonic algae.

The distribution of carotenoids in algae is followed by a presentation of the biosynthesis of carotenoids. This starts with the biosynthetic steps from small molecules to give carotenes, carotenoids consisting of only carbon and hydrogen. Further, the biosynthetic routes to major oxygen-containing carotenoids are described, before the various biosynthetic routes are linked together to large overviews including even rare algal carotenoids. A brief presentation of stress-induced carotenoid synthesis and biosynthetic cycles are included.

An overview about the practical laboratory work for the isolation and analyses of carotenoids follows. First, common precautions for work with carotenoids is presented, important as carotenoids are unstable compounds and will easily degrade during laboratory handling. Several practical tips are included, based on the author’s long experience in the field. The chapter gives recommendations for sample storage, extraction of pigments from the cells and the separation of the various carotenoids by chromatography. After separation, spectroscopic techniques are described for identification of the isolated carotenoids. The practical laboratory work ends with a presentation of common degradation products often observed when analysing carotenoids, compounds that may be misidentified as natural carotenoids.

The chapter ends with examples of uses for algal carotenoids followed by a brief presentation of large-scale production, also here with references for further studies.

Keywords

Carotenoids Pigments Carotenoid distribution Carotenoid biosynthesis Chemical analysis Secondary carotenoids Chromatography Spectroscopy Carotenoid degradation products 

Notes

Acknowledgements

The library at University of Nordland gets my sincere thanks for once again have provided several hundreds article copies and also some books loaned from other libraries. Always promptly, always with a smile, never questioning why I need it or why I need all that much. Luckily for you, this time, most of the literature needed was available through electronic access, and not so many had to be ordered manually.

References

  1. Aakermann T, Skulberg OM, Liaaen-Jensen S (1992) A comparison of the carotenoids of strains of Oscillatoria and Spirulina (Cyanobacteria). Biochem Syst Ecol 30:761–769CrossRefGoogle Scholar
  2. Aakermann T, Guillard RRL, Liaaen-Jensen S (1993) Algal carotenoids 55. Structure elucidation of (3S,5R,6R,3′S,5′R,6′S)-13′-cis-7′,8′-dihydroneoxanthin-20′-al 3′-β-D-lactoside (P457). Part 1. Reisolation, derivatization and synthesis of model compounds. Acta Chem Scand 47:1207–1213CrossRefGoogle Scholar
  3. Abbas A, Josefson M, Abrahamsson K (2011) Characterization and mapping of carotenoids in the algae Dunaliella and Phaeodactylum using Raman and target orthogonal partial least squares. Chemom Intell Lab 107:174–177CrossRefGoogle Scholar
  4. Abe K, Mihara H, Hirano M (1998) Characteristics of growth and carotenoid accumulation of the aerial microalga Trentepohlia aurea in liquid culture. J Mar Biotechnol 6:53–58Google Scholar
  5. Abe K, Hattori H, Hirano M (2007) Accumulation and antioxidant activity of secondary carotenoids in the aerial microalga Coelastrella striolata var. multistriata. Food Chem 100:656–661CrossRefGoogle Scholar
  6. Adl SM, Simpson AGB, Farmer MA, Andersen RA, Anderson OR, Barta JR, Bowser SS, Brugerolle G, Fensome RA, Fredericq S, James TY, Karpov S, Kugrens P, Krug J, Lane CE, Lewis LA, Lodge J, Lynn DH, Mann DG, McCourt RM, Mendoza L, Moestrup Ø, Mozley-Standridge SE, Nerad TA, Shearer CA, Smirnov AV, Spiegel FW, Taylor MFJR (2005) The new higher level classification of eukaryotes with emphasis on the taxonomy of protists. J Eukaryot Microbiol 52:399–451PubMedCrossRefGoogle Scholar
  7. Airs RL, Garrido JL (2011) Liquid chromatography-mass spectrometry for pigment analysis. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 314–342CrossRefGoogle Scholar
  8. Andersen RA (1987) Synurophyceae classis nov., a new class of algae. Am J Bot 74:337–353CrossRefGoogle Scholar
  9. Bailey JC, Bidigare RR, Christensen SJ, Andersen RA (1998) Phaeothamniophyceae classis nova: a new lineage of chromophytes based upon photosynthetic pigments, rbcL sequence analysis and ultrastructure. Protist 149:245–263CrossRefGoogle Scholar
  10. Ben-Amotz A, Polle JEW, Rao DVS (eds) (2009) The alga Dunaliella: biodiversity, physiology, genomics and biotechnology. Science Publishers, Enfield, 557 ppGoogle Scholar
  11. Bernhard K (1995) Chromatography: Part II column chromatography. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1A, Isolation and Analysis. Birkhäuser Verlag, Basel, pp 117–130Google Scholar
  12. Bjerkeng B (2008) Carotenoids in aquaculture: fish and crustaceans. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 4, Natural Functions. Birkhäuser Verlag, Basel, pp 237–254CrossRefGoogle Scholar
  13. Bjørnland T, Aguilar-Martinez M (1976) Carotenoids in red algae. Phytochemistry 15:291–296CrossRefGoogle Scholar
  14. Bjørnland T, Liaaen-Jensen S (1989) Distribution patterns of carotenoids in relation to chromophyte phylogeny and systematics. In: Green JC, Leadbeater BSC, Diver WL (eds) The chromophyte algae: problems and perspectives. Clarendon Press, Oxford, pp 37–60Google Scholar
  15. Bjørnland T, Borch G, Liaaen-Jensen S (1984) Configurational studies on red algae carotenoids. Phytochemistry 8:1711–1715CrossRefGoogle Scholar
  16. Bjørnland T, Borch G, Liaaen-Jensen S (1986) Additional oxa-biocyclo[2.2.1]heptane carotenoids from Eutreptiella gymnastica. Phytochemistry 25:201–205CrossRefGoogle Scholar
  17. Bjørnland T, Liaaen-Jensen S, Throndsen J (1989) Carotenoids of the marine chrysophyte Pelagococcus subviridis. Phytochemistry 28:3347–3353CrossRefGoogle Scholar
  18. Bjørnland T, Haxo FT, Liaaen-Jensen S (2003) Carotenoids of the Florida red tide dinoflagellate Karenia brevis. Biochem Syst Ecol 31:1147–1162CrossRefGoogle Scholar
  19. Bodył A, Moszczyński K (2007) Did the peridinin plastid evolve through tertiary endosymbiosis? A hypothesis. Eur J Phycol 41:435–448CrossRefGoogle Scholar
  20. Böhme K, Wilhelm C, Goss R (2002) Light regulation of carotenoid biosynthesis in the prasinophycean alga Mantoniella squamata. Photochem Photobiol Sci 1:619–628PubMedCrossRefGoogle Scholar
  21. Boonyaratpalin M, Thongrod S, Supamattaya K, Britton G, Schlipalius LE (2001) Effects of β-carotene source, Dunaliella salina, and astaxanthin on pigmentation, growth, survival and health of Penaeus monodon. Aquac Res 32(Suppl 1):182–190CrossRefGoogle Scholar
  22. Boonyareth M, Saranak J, Pinthong D, Sanvarinda Y, Foster KW (2009) Roles of cyclic AMP in regulation of phototaxis in Chlamydomonas reinhardtii. Biologia 64:1058–1065CrossRefGoogle Scholar
  23. Borowitzka MA (2010) Carotenoid production using microorganisms. In: Cohen Z, Ratledge C (eds) Single cell oils. Microbial and algal oils. AOCS Press, Urbana, pp 225–240CrossRefGoogle Scholar
  24. Borowitzka MA (2013a) High-value products from microalgae–their development and commercialisation. J Appl Phycol 25:743–756CrossRefGoogle Scholar
  25. Borowitzka MA (2013b) Dunaliella: biology, production, and markets. In: Richmond A, Hu Q (eds) Handbook of microalgal culture. Wiley, Oxford, pp 359–368CrossRefGoogle Scholar
  26. Borowitzka MA (2016) Systematics, taxonomy and species names: do they matter? In: Borowitzka MA, Beardall J, Raven JA (eds) The physiology of microalgae. Springer, Dordrecht, pp 655–681Google Scholar
  27. Borowitzka MA, Borowitzka LJ, Kessley D (1990) Effects of salinity increase on carotenoid accumulation in the green alga Dunaliella salina. J Appl Phycol 2:111–119CrossRefGoogle Scholar
  28. Bosma R, Wijffels RH (2003) Marine biotechnology in education: a competitive approach. Biomol Eng 20:125–131PubMedCrossRefGoogle Scholar
  29. Boussiba S (2000) Carotenogenesis in the green alga Haematococcus pluvialis: cellular physiology and stress response. Physiol Plant 108:111–117CrossRefGoogle Scholar
  30. Breithaupt DE (2008) Xanthophylls in poultry feeding. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 4, Natural functions. Birkhäuser Verlag, Basel, pp 255–264CrossRefGoogle Scholar
  31. Britton G (1995) UV/Visible spectroscopy. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1B, Spectroscopy. Birkhäuser Verlag, Basel, pp 13–62Google Scholar
  32. Britton G (2008a) Functions of intact carotenoids. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 4, Natural functions. Birkhäuser Verlag, Basel, pp 189–212CrossRefGoogle Scholar
  33. Britton G (2008b) Functions of carotenoid metabolites and breakdown products. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 4, Natural functions. Birkhäuser Verlag, Basel, pp 309–324CrossRefGoogle Scholar
  34. Britton G, Liaaen-Jensen S, Pfander H (eds) (1996) Carotenoids, vol 2, Synthesis. Birkhäuser Verlag, Basel, 359 ppGoogle Scholar
  35. Britton G, Liaaen-Jensen S, Pfander H (eds) (1998) Carotenoids, vol 3, Biosynthesis and metabolism. Birkhäuser Verlag, Basel, 414 ppGoogle Scholar
  36. Britton G, Liaaen-Jensen S, Pfander H (eds) Mercadante AZ, Egeland ES (compilers) (2004) Carotenoids: handbook. Birkhäuser Verlag, Basel, 647 ppGoogle Scholar
  37. Britton G, Liaaen-Jensen S, Pfander H (eds) (2008) Carotenoids, vol 4, Natural functions. Birkhäuser Verlag, Basel, 370 ppGoogle Scholar
  38. Britton G, Liaaen-Jensen S, Pfander H (eds) (2009) Carotenoids, vol 5, Nutrition and health. Birkhäuser Verlag, Basel, 431 ppGoogle Scholar
  39. Brunet C, Johnsen G, Lavaud J, Roy S (2011) Pigments and photoacclimation processes. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 445–471CrossRefGoogle Scholar
  40. Buchecker R, Noack K (1995) Circular dichroism. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1B, Spectroscopy. Birkhäuser Verlag, Basel, pp 63–116Google Scholar
  41. Campo JAD, García-González M, Guerrero MG (2007) Outdoor cultivation of microalgae for carotenoid production: current state and perspectives. Appl Microbiol Biotechnol 74:1163–1174PubMedCrossRefGoogle Scholar
  42. Cavalier-Smith T (2007) Evolution and relationships of algae: major branches of the tree of life. In: Brodie J, Lewis J (eds) Unravelling the algae: the past, present, and future of algal systematics. CRC Press, Boca Raton, pp 21–55CrossRefGoogle Scholar
  43. Cazzonelli CI, Pogson BJ (2010) Source to sink: regulation of carotenoid biosynthesis in plants. Trends Plant Sci 15:266–274PubMedCrossRefGoogle Scholar
  44. Chen M, Schliep M, Willows RD, Cai Z-L, Neilan BA, Scheer H (2010) A red-shifted chlorophyll. Science 329:1318–1319PubMedCrossRefGoogle Scholar
  45. Chen M, Li Y, Birch D, Willows RD (2012) A cyanobacterium that contains chlorophyll f – a red-absorbing photopigment. FEBS Lett 586:3249–3254PubMedCrossRefGoogle Scholar
  46. Chen L, Zhang L, Zhang W, Liu T (2015) Comparative analysis of growth and carotenoid accumulation of Trentepohlia arborum in aerial, subaerial, and aquatic cultivation. J Appl Phycol 27:1079–1087CrossRefGoogle Scholar
  47. Christensen T (1980–1994) Algae: a taxonomic survey. AiO Print, Odense. 472 ppGoogle Scholar
  48. Collins AM, Jones HDT, Han D, Hu Q, Beechem TE, Timlin JA (2011) Carotenoid distribution in living cells of Haematococcus pluvialis (Chlorophyceae). PLoS One 6:e24302PubMedPubMedCentralCrossRefGoogle Scholar
  49. Colombo-Pallotta MF, García-Mendoza E, Ladah LB (2006) Photosynthetic performance, light absorption, and pigment composition of Macrocystis pyrifera (Laminariales, Phaeophyceae) blades from different depths. J Phycol 42:1225–1234CrossRefGoogle Scholar
  50. Cordero BF, Obraztsova I, Martín L, Couso I, León R, Vargas MÁ, Rodríguez H (2010) Isolation and characterization of a lycopene β-cyclace gene from the astaxantin-producing green alga Chlorella zofingiensis (Chlorophyta). J Phycol 46:1229–1238CrossRefGoogle Scholar
  51. Cordero BF, Obraztsova I, Couso I, Leon R, Vargas MA, Rodriguez H (2011) Enhancement of lutein production in Chlorella sorokiniana (Chlorophyta) by improvement of culture conditions and random mutagenesis. Mar Drugs 9:1607–1624PubMedPubMedCentralCrossRefGoogle Scholar
  52. Crespo C, Rodríguez H, Segade P, Iglesias R, García-Estévez JM (2009) Coccomyxa sp. (Chlorophyta: Chlorococcales), a new pathogen in mussels (Mytilus galloprovincialis) of Vigo estuary (Galicia, NW Spain). J Invertebr Pathol 102:214–219PubMedCrossRefGoogle Scholar
  53. Cunningham FX, Gantt E (2011) Elucidation of the pathway to astaxanthin in the flowers of Adonis aestivalis. Plant Cell 23:3055–3069PubMedPubMedCentralCrossRefGoogle Scholar
  54. Delwiche CF (1999) Tracing the thread of plastid diversity through the tapestry of life. Am Nat 154:S164–S177PubMedCrossRefGoogle Scholar
  55. Demmig-Adams B, Adams WW (1993) The xanthophyll cycle. In: Young A, Britton G (eds) Carotenoids in photosynthesis. Chapman and Hall, London, pp 206–251CrossRefGoogle Scholar
  56. Descy J-P, Hardy M-A, Sténuite S, Pirlot S, Leporcq B, Kimirei I, Sekadende B, Mwaitega SR, Sinyenza D (2005) Phytoplankton pigments and community composition in Lake Tanganyika. Freshw Biol 50:668–684CrossRefGoogle Scholar
  57. Descy J-P, Tarbe A-L, Stenuite S, Pirlot S, Stimart J, Vanderheyden J, Leporcq B, Stoyneva MP, Kimirei I, Sinyinza D, Plisnier P-D (2010) Drivers of phytoplankton diversity in Lake Tanganyika. Hydrobiologia 653:29–44CrossRefGoogle Scholar
  58. Dobrzyn P, Tatur A, Keck A (2009) Photosynthetic pigments as indicators of phytoplankton development during spring and summer in Adventfjorden (Spitsbergen). Oceanology 49:368–376CrossRefGoogle Scholar
  59. Dufossé L (2009) Microbial and microalgal carotenoids as colourants and supplements. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 5, Nutrition and health. Birkhäuser Verlag, Basel, pp 83–98CrossRefGoogle Scholar
  60. Dufossé L, Galaup P, Yaron A, Arad SM, Blanc P, Murthy KNC, Ravishankar GA (2005) Microorganisms and microalgae as sources of pigments for food use: a scientific oddity or an industrial reality? Trends Food Sci Technol 16:389–406CrossRefGoogle Scholar
  61. Edvardsen B, Eikrem W, Shalchian-Tabrizi K, Riisberg I, Johnsen G, Naustvoll L, Throndsen J (2007) Verruchophora farcimen gen. et sp. nov. (Dictyochophyceae, Heterokonta)–a bloom-forming ichthyotoxic flagellate from the Skagerrak, Norway. J Phycol 43:1054–1070CrossRefGoogle Scholar
  62. Egeland ES (1996) Algekarotenoider og kjemosystematikk. Dr ing thesis no. 1996:92, Norwegian University of Science and Technology, Trondheim, 221 ppGoogle Scholar
  63. Egeland ES (2011a) Data sheets aiding identification of phytoplankton carotenoids and chlorophylls. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 665–822Google Scholar
  64. Egeland ES (2011b) Minimum identification criteria for phytoplankton pigments. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 650–652CrossRefGoogle Scholar
  65. Egeland ES (2011c) Specific absorption coefficients for major algal chlorophylls, bacteriochlorophylls and carotenoids. Electronic supplement to Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, 49 pp. Downloadable from http://www.cambridge.org/download_file/212953
  66. Egeland ES, Schlüter L (2011) Appendix E: commercial suppliers of phytoplankton pigments. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 658–663CrossRefGoogle Scholar
  67. Egeland ES, Johnsen G, Liaaen-Jensen S (1996) Variable carotenoid composition in a prasinophycean phytoplankton acclimated to three different irradiances. In: 11th international symposium on carotenoids, abstract of poster presentations, Leiden, p 92Google Scholar
  68. Egeland ES, Guillard RRL, Liaaen-Jensen S (1997) Additional carotenoid prototype representatives and a general chemosystematic evaluation of carotenoids in Prasinophyceae (Chlorophyta). Phytochemistry 44:1087–1097CrossRefGoogle Scholar
  69. Egeland ES, Garrido JL, Zapata M, Maestro MA, Liaaen-Jensen S (2000) Algal carotenoids. Part 64. Structure and chemistry of 4-keto-19′-hexanoyloxyfucoxanthin with a novel carotenoid end group. J Chem Soc Perkin Trans 1:1223–1230CrossRefGoogle Scholar
  70. Eikrem W, Romari K, Latasa M, Gall FL, Throndsen J, Vaulot D (2004) Florenciella parvula gen. et sp. nov. (Dictyochophyceae, Heterokontophyta), a small flagellate isolated from the English Channel. Phycologia 43:658–668CrossRefGoogle Scholar
  71. Englert G (1995) NMR spectroscopy. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1B, Spectroscopy. Birkhäuser Verlag, Basel, pp 147–260Google Scholar
  72. Enzell CR, Back S (1995) Mass spectrometry. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1B, Spectroscopy. Birkhäuser Verlag, Basel, pp 261–320Google Scholar
  73. Esteban R, Martínez B, Fernández-Marín B, Becerril JM, García-Plazaola JI (2009) Carotenoid composition in Rhodophyta: insights into xanthophyll regulation in Corallina elongata. Eur J Phycol 44:221–230CrossRefGoogle Scholar
  74. Eugster CH (1995) Chemical derivatization: microscale tests for the presence of common functional groups in carotenoids. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1A, Isolation and analysis. Birkhäuser Verlag, Basel, pp 71–80Google Scholar
  75. Evertsen J, Johnsen G (2009) In vivo and in vitro differences in chloroplast functionality in the two north Atlantic sacoglossans (Gastropoda, Opisthobranchia) Placida dendritica and Elysia viridis. Mar Biol 156:847–859CrossRefGoogle Scholar
  76. Falkowski PG, Raven JA (2007) Aquatic photosynthesis, 2nd edn. Princeton University Press, Princeton, 484 ppGoogle Scholar
  77. Fiksdahl A, Liaaen-Jensen S (1988) Diacetylenic carotenoids from Euglena viridis. Phytochemistry 27:1447–1450CrossRefGoogle Scholar
  78. Fiksdahl A, Bjørnland T, Liaaen-Jensen S (1984a) Algal carotenoids with novel end groups. Phytochemistry 23:649–655CrossRefGoogle Scholar
  79. Fiksdahl A, Withers N, Guillard RRL, Liaaen-Jensen S (1984b) Carotenoids of the Raphidophyceae–a chemosystematic contribution. Comp Biochem Physiol 78B:265–271Google Scholar
  80. Foss P, Guillard RRL, Liaaen-Jensen S (1984) Prasinoxanthin–a chemosystematic marker for algae. Phytochemistry 23:1629–1633CrossRefGoogle Scholar
  81. Foss P, Guillard RRL, Liaaen-Jensen S (1986) Carotenoids from eukaryotic ultraplankton clones (Prasinophyceae). Phytochemistry 25:119–124CrossRefGoogle Scholar
  82. Furuya K, Lirdwitayaprasit T (2000) Pigment composition of Pedinomonas noctilucae (Pedinophyceae), and endosymbiont of green Noctiluca (Dinophyceae). La Mer 38:95–97Google Scholar
  83. Ganesan P, Noda K, Manabe Y, Ohkubo T, Tanaka Y, Maoka T, Sugawara T, Hirata T (2011) Siphonaxanthin, a marine carotenoid from green algae, effectively induces apoptosis in human leukemia (HL-60) cells. Biochim Biophys Acta 1810:497–503PubMedCrossRefGoogle Scholar
  84. Gao Z, Meng C, Zhang X, Xu D, Zhao Y, Wang Y, Lv H, Yang L, Chen L, Ye N (2012a) Differential expression of carotenogenic genes, associated changes of astaxanthin production and photosynthesis features induced by JA in H. pluvialis. PLoS One 7:e42243PubMedPubMedCentralCrossRefGoogle Scholar
  85. Gao Z, Meng C, Zhang X, Xu D, Miao X, Wang Y, Yang L, Lv H, Chen L, Ye N (2012b) Induction of salicylic acid (SA) on transcriptional expression of eight carotenoid genes and astaxanthin accumulation in Haematococcus pluvialis. Enzym Microb Technol 51:225–230CrossRefGoogle Scholar
  86. Gin KYH, Zhang S, Lee YK (2003) Phytoplankton community structure in Singapore’s coastal waters using HPLC pigment analysis and flow cytometry. J Plankton Res 25:1507–1519CrossRefGoogle Scholar
  87. Goodwin TW (1980) The biochemistry of carotenoids, vol 1, 2nd edn, Plants. Chapman and Hall, London, 377 ppCrossRefGoogle Scholar
  88. Graham JE, Bryant DA (2008) The biosynthetic pathway for synechoxanthin, an aromatic carotenoid synthesized by the euryhaline, unicellular cyanobacterium Synechococcus sp. strain PCC 7002. J Bacteriol 190:7966–7974PubMedPubMedCentralCrossRefGoogle Scholar
  89. Graham JE, Lecomte JTJ, Bryant DA (2008) Synechoxanthin, an aromatic C40 xanthophyll that is a major carotenoid in the cyanobacterium Synechococcus sp. PCC 7002. J Nat Prod 71:1647–1650PubMedCrossRefGoogle Scholar
  90. Graham LE, Graham JM, Wilcox LW (2009) Algae, 2nd edn. Benjamin Cummings, San Francisco, 698 ppGoogle Scholar
  91. Greenberger S, Harats D, Salameh F, Lubish T, Harari A, Trau H, Shaish A (2012) 9-cis-Rich β-carotene powder of the alga Dunaliella reduces the severity of chronic plaque psoriasis: a randomized, double-blind, placebo-controlled clinical trial. J Am Coll Nutr 31:320–326PubMedCrossRefGoogle Scholar
  92. Grosser K, Zedler L, Schmitt M, Dietzek B, Popp J, Pohnert G (2012) Disruption-free imaging by Raman spectroscopy reveals a chemical sphere with antifouling metabolites around macroalgae. Biofouling 28:687–696PubMedCrossRefGoogle Scholar
  93. Grung M, Liaaen-Jensen S (1993) Algal carotenoids 52; secondary carotenoids of algae 3; carotenoids in a natural bloom of Euglena sanguinea. Biochem Syst Ecol 21:757–763CrossRefGoogle Scholar
  94. Grung M, D’Souza FML, Borowitzka MA, Liaaen-Jensen S (1992) Algal carotenoids 51. Secondary carotenoids 2. Haematococcus pluvialis aplanospores as a source of (3S,3′S)-astaxanthin esters. J Appl Phycol 4:165–171CrossRefGoogle Scholar
  95. Gruszecki WI (2010) Carotenoids in lipid membranes. In: Landrum JT (ed) Carotenoids: physical, chemical and biological functions and properties. CRC Press, Boca Raton, pp 19–30Google Scholar
  96. Guaratini T, Cardozo KHM, Pinto E, Colepicolo P (2009) Comparison of diode array and electrochemical detection in the C30 reverse phase HPLC analysis of algae carotenoids. J Braz Chem Soc 20:1609–1616CrossRefGoogle Scholar
  97. Guedes AC, Amaro HM, Malcata FX (2011) Microalgae as sources of carotenoids. Mar Drugs 9:625–644PubMedPubMedCentralCrossRefGoogle Scholar
  98. Guidi-Rontani C, Maheswari U, Jabbari K, Bowler C (2010) Comparative ecophysiology and genomics of the toxic unicellular alga Fibrocapsa japonica. New Phytol 185:446–458PubMedCrossRefGoogle Scholar
  99. Guil-Guerrero JL, Rebolloso-Fuentes MM (2008) Nutrient composition of Chlorella spp. and Monodus subterraneus cultured in a bubble column reactor. Food Biotechnol 22:218–233CrossRefGoogle Scholar
  100. Guillou L, Chrétiennot-Dinet MJ, Medlin LK, Claustre H, Goër SL-d, Vaulot D (1999) Bolidomonas: a new genus with two species belonging to a new algal class, the Bolidophyceae (Heterokonta). J Phycol 35:368–381CrossRefGoogle Scholar
  101. Harada K-I, Ozaki K, Tsuzuki S, Kato H, Hasegawa M, Kuroda EK, Arii S, Tsuji K (2009) Blue color formation of cyanobacteria with β-cyclocitral. J Chem Ecol 35:1295–1301PubMedCrossRefGoogle Scholar
  102. Harker M, Hirschberg J (1997) Biosynthesis of ketocarotenoids in transgenic cyanobacteria expressing the algal gene for β-C-4-oxygenase, crtO. FEBS Lett 404:129–134PubMedCrossRefGoogle Scholar
  103. Haugan JA, Liaaen-Jensen S (1994a) Algal carotenoids 54. Carotenoids of brown algae (Phaeophyceae). Biochem Syst Ecol 22:31–41CrossRefGoogle Scholar
  104. Haugan JA, Liaaen-Jensen S (1994b) Blue carotenoids. Part 2. The chemistry of the classical colour reaction of common carotenoid 5,6-epoxides with acid. Acta Chem Scand 48:152–159CrossRefGoogle Scholar
  105. Haugan JA, Liaaen-Jensen S (1994c) Blue carotenoids. Part 1. Novel oxonium ions derived from fucoxanthin. Acta Chem Scand 48:68–75CrossRefGoogle Scholar
  106. Hertzberg S, Liaaen-Jensen S, Siegelman HW (1971) The carotenoids of blue-green algae. Phytochemistry 10:3121–3127CrossRefGoogle Scholar
  107. Higgins HW, Mackey DJ, Clementson ML (2006) Phytoplankton distribution in the Bismarck Sea north of Papua New Guinea: the effect of the Sepik river outflow. Deep-Sea Res I 53:1845–1863CrossRefGoogle Scholar
  108. Hirschberg J (1998) Molecular biology of carotenoid biosynthesis. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 3, Biosynthesis and metabolism. Birkhäuser Verlag, Basel, pp 149–194Google Scholar
  109. Horath T, Neu TR, Bachofen R (2006) An endolithic microbial community in Dolomite rock in Central Switzerland: characterization by reflection spectroscopy, pigment analysis, scanning electron microscopy and laser scanning microscopy. Microb Ecol 51:353–364PubMedCrossRefGoogle Scholar
  110. Horn S, Ehlers K, Fritzsch G, Gil-Rodríguez MC, Wilhelm C, Schnetter R (2007) Synchroma grande spec. nov. (Synchromophyceae class. nov., Heterokontophyta): an amoeboid marine alga with unique plastid complexes. Protist 158:277–293PubMedCrossRefGoogle Scholar
  111. Huang YY, Beal CM, Cai WW, Ruoff RS, Terentjev EM (2009) Micro-Raman spectroscopy of algae: composition analysis and fluorescence background behaviour. Biotechnol Bioeng 105:889–898Google Scholar
  112. Hynes N, Egeland ES, Koppe W, Baardsen G, Kiron V (2009) Calanus oil as a natural source for flesh pigmentation in Atlantic salmon (Salmo salar L.). Aquac Nutr 15:202–208CrossRefGoogle Scholar
  113. IUPAC Commission on the Nomenclature of Organic Chemistry, IUPAC–IUB Commission on Biochemical Nomenclature (1975) Nomenclature of carotenoids (Rules approved 1974). Pure Appl Chem 41:405–431Google Scholar
  114. IUPAC, Division of Chemical Nomenclature and Structure Representation (2014) Nomenclature of organic chemistry. IUPAC recommendations and preferred names 2013. Prepared by Favre HA, Powell WH, Royal Society of Chemistry, Cambridge, 1611 ppGoogle Scholar
  115. Jeffrey SW, Egeland ES (2009) Pigments of green and red forms of Dunaliella, and related chlorophytes. In: Ben-Amotz A, Polle JEW, Rao DVS (eds) The alga Dunaliella: biodiversity, physiology, genomics and biotechnology. Science Publishers, Enfield, pp 111–145CrossRefGoogle Scholar
  116. Jeffrey SW, Mantoura RFC, Wright SW (1997) Phytoplankton pigments in oceanography: guidelines to modern methods. Unesco Publishing, Paris, 661 ppGoogle Scholar
  117. Jeffrey SW, Wright SW, Zapata M (2011) Microalgal classes and their signature pigments. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 3–77CrossRefGoogle Scholar
  118. Jin E, Polle JEW, Lee HK, Hyun SM, Chang M (2003) Xanthophylls in microalgae: from biosynthesis to biotechnological mass production and application. J Microbiol Biotechnol 13:165–174Google Scholar
  119. Jodłowska S, Latała A (2013) Combined effects of light and temperature on growth, photosynthesis, and pigment content in the mat-forming cyanobacterium Geitlerinema amphibium. Photosynthetica 51:202–214CrossRefGoogle Scholar
  120. Johansen JE, Svec WA, Liaaen-Jensen S, Haxo FT (1974) Carotenoids of the Dinophyceae. Phytochemistry 13:2261–2271CrossRefGoogle Scholar
  121. Ju ZY, Deng D-F, Dominy WG (2011) Pigmentation of Pacific white shrimp, Litopenaeus vannamei, by dietary astaxanthin extracted from Haematococcus pluvialis. J World Aquacult Soc 42:633–644CrossRefGoogle Scholar
  122. Jüttner F, Watson SB, Ev E, Köster O (2010) β-Cyclocitral, a grazer defence signal unique to the cyanobacterium Microcystis. J Chem Ecol 36:1387–1397PubMedCrossRefGoogle Scholar
  123. Kai A, Yoshii Y, Nakayama T, Inouye I (2008) Aurearenophyceae classis nova, a new class of Heterokontophyta based on a new marine unicellular alga Aureareana cruciata gen. et sp. nov. inhabiting sandy beaches. Protist 159:435–457PubMedCrossRefGoogle Scholar
  124. Kawachi M, Inouye I, Honda D, O’Kelly CJ, Bailey JC, Bidigare RR, Andersen RA (2002) The Pinguiophyceae classis nova, a new class of photosynthetic stramenophiles whose members produce large amounts of omega-3 fatty acids. Phycol Res 50:31–47CrossRefGoogle Scholar
  125. Kawai H, Maeba S, Sasaki H, Okuda K, Henry EC (2003) Schizocladia ischiensis: a new filamentous marine chromophyte belonging to a new class, Schizocladiophyceae. Protist 154:211–228PubMedCrossRefGoogle Scholar
  126. Keeling PJ, Burger G, Durnford DG, Lang BF, Lee RW, Pearlman RE, Roger AJ, Gray MW (2005) The tree of eukaryotes. Trends Ecol Evol 20:670–676PubMedCrossRefGoogle Scholar
  127. Khalil ZI, Asker MMS, El-Sayed S, Kobbia IA (2010) Effect of pH on growth and biochemical responses of Dunaliella bardawil and Chlorella ellipsoidea. World J Microbiol Biotechnol 26:1225–1231PubMedCrossRefGoogle Scholar
  128. Kleinegris DMM, Janssen M, Brandenburg WA, Wijffels RH (2011) Two-phase systems: potential for in situ extraction of microalgal products. Biotechnol Adv 29:502–507PubMedCrossRefGoogle Scholar
  129. Kobayashi M (2003) Astaxanthin biosynthesis enhanced by reactive oxygen species in the green alga Haematococcus pluvialis. Biotechnol Bioproc Eng 8:322–330CrossRefGoogle Scholar
  130. Kotrbáček V, Skřivan M, Kopecký J, Pěnkava O, Hudečkova P, Uhríková I, Doubek J (2013) Retention of carotenoids in egg yolks of laying hens supplemented with heterotrophic Chlorella. Czech J Anim Sci 58:193–200Google Scholar
  131. Küster A, Schaible R, Schubert H (2005) Sex-specific light acclimation of Chara canescens (Charophyta). Aquat Bot 83:129–140CrossRefGoogle Scholar
  132. Lamers PP, Laak CCW, Kaasenbrood PS, Lorier J, Janssen M, Vos RCHD, Bino RJ, Wijffels RH (2010) Carotenoid and fatty acid metabolism in light-stressed Dunaliella salina. Biotechnol Bioeng 106:638–648PubMedCrossRefGoogle Scholar
  133. Larkum AW (2016) Photosynthesis and light harvesting in algae. In: Borowitzka MA, Beardall J, Raven JA (eds) Physiology of microalgae. Springer, Dordrecht, pp 67–87Google Scholar
  134. Larkum AWD, Douglas SE, Raven JA (eds) (2003) Photosynthesis in algae. Advances in photosynthesis and respiration, vol 14. Kluwer Academic Publishers, Dordrecht, 480 ppGoogle Scholar
  135. Laza-Martinez A, Seoane S, Zapata M, Orive E (2007) Phytoplankton pigment patterns in a temperate estuary: from unialgal cultures to natural assemblages. J Plankton Res 29:913–929CrossRefGoogle Scholar
  136. Lee Y-K, Zhang D-H (1999) Production of astaxanthin by Haematococcus. In: Cohen Z (ed) Chemicals from microalgae. Taylor & Francis, London, pp 173–195Google Scholar
  137. Lemoine Y, Schoefs B (2010) Secondary ketocarotenoid astaxanthin and biosynthesis in algae: a multifunctional response to stress. Photosynth Res 106:155–177PubMedCrossRefGoogle Scholar
  138. Li Y, Sommerfeld M, Chen F, Hu Q (2008) Consumption of oxygen by astaxanthin biosynthesis: a protective mechanism against oxidative stress in Haematococcus pluvialis (Chlorophyceae). J Plant Physiol 165:1783–1797PubMedCrossRefGoogle Scholar
  139. Li Z, Ma X, Li A, Zhang C (2012) A novel potential source of β-carotene: Eustigmatos cf. polyphem (Eustigmatophyceae) and pilot β-carotene production in bubble column and flat panel photobioreactors. Bioresour Technol 117:257–263PubMedCrossRefGoogle Scholar
  140. Liaaen-Jensen S (1998) Carotenoids in chemosystematics. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 3, Biosynthesis. Birkhäuser Verlag, Basel, pp 217–247Google Scholar
  141. Liaaen-Jensen S, Egeland ES (1999) Microalgal carotenoids. In: Cohen Z (ed) Chemicals from microalgae. Taylor & Francis, London, pp 145–172Google Scholar
  142. Lichtenthaler HK, Schwender J, Disch A, Rohmer M (1997) Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Lett 400:271–274PubMedCrossRefGoogle Scholar
  143. Lichtlé C, Arsalane W, Duval JC, Passaquet C (1995) Characterization of the light-harvesting complex of Giraudyopsis stellifer (Chrysophyceae) and effects of light stress. J Phycol 31:380–387CrossRefGoogle Scholar
  144. Loebich LA (1982) Photosynthesis and pigments influenced by light intensity and salinity in the halophile Dunaliella salina (Chlorophyceae). J Mar Biol Assoc U K 62:493–508CrossRefGoogle Scholar
  145. Lohr M (2011) Carotenoid metabolism in phytoplankton. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 113–161CrossRefGoogle Scholar
  146. Lohr M, Wilhelm C (1999) Algae displaying the diadinoxanthin cycle also possess the violaxanthin cycle. Proc Natl Acad Sci U S A 96:8784–8789PubMedPubMedCentralCrossRefGoogle Scholar
  147. Lohr M, Schwender J, Polle JEW (2012) Isoprenoid biosynthesis in eukaryotic phototrophs: a spotlight on algae. Plant Sci 185–186:9–22PubMedCrossRefGoogle Scholar
  148. Louda JW (2008) HPLC-based chemotaxonomy of Florida Bay phytoplankton: difficulties in coastal environments. J Liq Chromatogr Relat Technol 31:295–323CrossRefGoogle Scholar
  149. Mackey MD, Mackey DJ, Higgins HW, Wright SW (1996) CHEMTAX–a program for estimating class abundances from chemical markers: application to HPLC measurements of phytoplankton. Mar Ecol Prog Ser 144:265–283CrossRefGoogle Scholar
  150. Maoka T, Akimoto N, Tsushima M, Komemushi S, Mezaki T, Iwase F, Takahashi Y, Sameshima N, Mori M, Sakagami Y (2011a) Carotenoids in marine invertebrates living along the Kuroshio current coast. Mar Drugs 9:1419–1427PubMedPubMedCentralCrossRefGoogle Scholar
  151. Maoka T, Etoh T, Kishimoto S, Sakata S (2011b) Carotenoids and their fatty acid esters in the petals of Adonis aestivalis. J Oleo Sci 60:47–52PubMedCrossRefGoogle Scholar
  152. Marin B, Melkonian M (2010) Molecular phylogeny and classification of the Mamiellophyceae class. nov. (Chlorophyta) based on sequence comparisons of the nuclear- and plastid-encoded rRNA operons. Protist 161:304–336PubMedCrossRefGoogle Scholar
  153. Matsumoto T, Kawachi M, Miyashita H, Inagaki Y (2012) Prasinoxanthin is absent in the green-colored dinoflagellate Lepidodinium chlorophorum strain NIES-1868: pigment composition and 18S rRNA phylogeny. J Plant Res 125:705–711PubMedCrossRefGoogle Scholar
  154. McGowan S, Barker P, Haworth EY, Leavitt PR, Maberly SC, Pates J (2012) Humans and climate as drivers of algal community change in Windermere since 1850. Freshw Biol 57:260–277CrossRefGoogle Scholar
  155. Meyer-Harms B, Pollehne F (1998) Alloxanthin in Dinophysis norvegica (Dinophysiales, Dinophyceae) from the Baltic Sea. J Phycol 34:280–285CrossRefGoogle Scholar
  156. Milledge JJ (2011) Commercial applications of microalgae other than as biofuels: a brief review. Rev Environ Sci Biotechnol 10:31–41CrossRefGoogle Scholar
  157. Moewus F (1938) Carotinoide as Sexualstoffe von Algen. Jahrb Wiss Bot 86:753–783Google Scholar
  158. Moewus F (1940) Carotinoid-Derivate als geschlechtsbestimmende Stoffe von Algen. Biol Zbl 60:143–166Google Scholar
  159. Mogedas B, Casal C, Forján E, Vílchez C (2009) β-Carotene production enhancement by UV-A radiation in Dunaliella bardawil cultivated in laboratory reactors. J Biosci Bioeng 108:47–51PubMedCrossRefGoogle Scholar
  160. Mohamed HE, Meene AML, Roberson RW, Vermaas WFJ (2005) Myxoxanthophyll is required for normal cell wall structure and thylakoid organization in the cyanobacterium Synechocystis sp. strain PCC 6803. J Bacteriol 187:6883–6892PubMedPubMedCentralCrossRefGoogle Scholar
  161. Mortensen A (2009) Supplements. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 5, Nutrition and health. Birkhäuser Verlag, Basel, pp 67–82CrossRefGoogle Scholar
  162. Nakanishi K (1991) 11-cis-retinal, a molecule uniquely suited for vision. Pure Appl Chem 63:161–170CrossRefGoogle Scholar
  163. Norgård S, Svec WA, Liaaen-Jensen S, Jensen A, Guillard RRL (1974) Chloroplast pigments and algal systematics. Biochem Syst Ecol 2:3–6CrossRefGoogle Scholar
  164. Ocampo-Alvarez H, García-Mendoza E, Govindjee (2013) Antagonist effect between violaxanthin and de-epoxidated pigments in nonphotochemical quenching induction in the qE deficient brown alga Macrocystis pyrifera. Biochim Biophys Acta 1827:427–437PubMedCrossRefGoogle Scholar
  165. Ohi Y, Namiki T, Katatae M, Tsukahara H, Kitamura A (2009) Effects of the addition of the natural carotenoid astaxanthin from microalgae Haematococcus pluvialis on the physical properties of bread. Nippon Shokuhin Kagaku Kogaku Kaishi 56:579–584CrossRefGoogle Scholar
  166. Orosa M, Franqueira D, Cid A, Abalde J (2005) Analysis and enhancement of astaxanthin accumulation in Haematococcus pluvialis. Bioresour Technol 96:373–378PubMedCrossRefGoogle Scholar
  167. Palinska KA, Deventer B, Hariri K, Łotocka M (2011) A taxonomic study on Phormidium-group (cyanobacteria) based on morphology, pigments, RAPD molecular markers and RFLP analysis of the 16S rRNA gene fragment. Fottea 11:41–51CrossRefGoogle Scholar
  168. Pennington FC, Haxo FT, Borch G, Liaaen-Jensen S (1985) Carotenoids of Cryptophyceae. Biochem Syst Ecol 13:215–219CrossRefGoogle Scholar
  169. Pennington F, Guillard RRL, Liaaen-Jensen S (1988) Carotenoid distribution patterns in Bacillariophyceae (Diatoms). Biochem Syst Ecol 16:589–592CrossRefGoogle Scholar
  170. Pereira MG, Icely J, Mudge S, Newton A, Rodrigues R (2013) Temporal and spatial variation of phytoplankton pigments in the western part of Ria Formosa Lagoon, Southern Portugal. Environ Forensic 8:205–220CrossRefGoogle Scholar
  171. Pfander H, Riesen R (1995) Chromatography: Part IV high-performance liquid chromatography. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1A, Isolation and analysis. Birkhäuser Verlag, Basel, pp 145–190Google Scholar
  172. Pinckney JL, Millie DF, Heukelem LV (2011) Update on filtration, storage and extraction solvents. In: Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, pp 627–635CrossRefGoogle Scholar
  173. Poole CF (2003) The essence of chromatography. Elsevier, Amsterdam, 925 ppGoogle Scholar
  174. Raman V, Ravi S (2011) Effect of salicylic acid and methyl jasmonate on antioxidant systems of Haematococcus pluvialis. Acta Physiol Plant 33:1043–1049CrossRefGoogle Scholar
  175. Reuss N, Conley DJ, Bianchi TS (2005) Preservation conditions and the use of sediment pigments as a tool for recent ecological reconstruction in four Northern European estuaries. Mar Chem 95:283–302CrossRefGoogle Scholar
  176. Řezanka T, Nedbalová L, Sigler K, Cepák V (2008) Identification of astaxanthin diglucoside diesters from snow alga Chlamydomonas nivalis by liquid chromatography–atmospheric pressure chemical ionization mass spectrometry. Phytochemistry 69:479–490PubMedCrossRefGoogle Scholar
  177. Řezanka T, Nedbalová L, Kolouchová I, Sigler K (2013) LC–MS/APCI identification of glucoside esters and diesters of astaxanthin from the snow alga Chlamydomonas nivalis including their optical stereoisomers. Phytochemistry 88:34–42PubMedCrossRefGoogle Scholar
  178. Roesler CS, Culbertson CW, Etheridge SM, Goericke R, Kiene RP, Miller LG, Oremland RS (2002) Distribution, production, and ecophysiology of Picocystis strain ML in Mono Lake, California. Limnol Oceanogr 47:440–452CrossRefGoogle Scholar
  179. Rotenstreich Y, Harats D, Shaish A, Pras E, Belkin M (2010) Treatment of a retinal dystrophy, fundus albipunctatus, with oral 9-cis-β-carotene. Br J Ophthalmol 94:616–621PubMedCrossRefGoogle Scholar
  180. Roy S, Llewellyn CA, Egeland ES, Johnsen G (eds.) (2011) Phytoplankton pigments: characterization, chemotaxonomy and applications in oceanography. Cambridge University Press, Cambridge, 845 ppGoogle Scholar
  181. Saha M, Rempt M, Grosser K, Pohnert G, Weinberger F (2011) Surface-associated fucoxanthin mediates settlement of bacterial epiphytes on the rockweed Fucus vesiculosus. Biofouling 27:423–433PubMedCrossRefGoogle Scholar
  182. Salguero A, Morena B, Vigara J, Vega JM, Vilchez C, León R (2003) Carotenoids as protective response against oxidative damage in Dunaliella bardawil. Biomol Eng 20:249–253PubMedCrossRefGoogle Scholar
  183. Sasa T, Takaichi S, Hatakeyama N, Watanabe MM (1992) A novel carotenoid ester, loroxanthin dodecenoate, from Pyramimonas parkeae (Prasinophyceae) and a chlorarachniophycean alga. Plant Cell Physiol 33:921–925Google Scholar
  184. Schiedt K (1995) Chromatography: Part III thin-layer chromatography. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1A, Isolation and analysis. Birkhäuser Verlag, Basel, pp 131–144Google Scholar
  185. Schiedt K, Liaaen-Jensen S (1995) Isolation and analysis. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 1A, Isolation and analysis. Birkhäuser Verlag, Basel, pp 81–108Google Scholar
  186. Schmidt M, Horn S, Flieger K, Ehlers K, Wilhelm C, Schnetter R (2012) Synchroma pusillum sp. nov. and other new algal isolates with chloroplast complexes confirm the Synchromophyceae (Ochrophyta) as a widely distributed group of amoeboid algae. Protist 163:544–559PubMedCrossRefGoogle Scholar
  187. Schubert N, García-Mendoza E, Pacheco-Ruiz I (2006) Carotenoid composition of marine red algae. J Phycol 42:1208–1216CrossRefGoogle Scholar
  188. Schubert N, García-Mendoza E, Enríquez S (2011) Is the photo-acclimatory response of Rhodophyta conditioned by the species carotenoid profile? Limnol Oceanogr 56:2347–2361CrossRefGoogle Scholar
  189. Schwender J, Zeidler J, Gröner R, Müller C, Focke M, Braun S, Lichtenthaler FW, Lichtenthaler HK (1997) Incorporation of 1-deoxy-D-xylulose into isoprene and phytol by higher plants and algae. FEBS Lett 414:129–134PubMedCrossRefGoogle Scholar
  190. Seoane S, Zapata M, Orive E (2009) Growth rates and pigment patterns of haptophytes isolated from estuarine waters. J Sea Res 62:286–294CrossRefGoogle Scholar
  191. Shi DY, Han LJ, Sun J, Li S, Wang SJ, Yang YC, Fan X, Shi JG (2005) A new halogenated biindole and a new apo-carotenone from green alga Chaetomorpha basiretorsa [sic!] Setchell. Chin Chem Lett 16:777–780Google Scholar
  192. Sigaud-Kutner TCS, Neto AMP, Pinto E, Colepicolo P (2005) Diel activities of antioxidant enzymes, photosynthetic pigments and malondialdehyde content in stationary-phase cells of Tetraselmis gracilis (Prasinophyceae). Aquat Biol 82:239–249CrossRefGoogle Scholar
  193. Six C, Thomas JC, Brahamsha B, Lemoine Y, Partensky F (2004) Photophysiology of the marine cyanobacterium Synechococcus sp. WH8102, a new model organism. Aquat Microb Ecol 35:17–29CrossRefGoogle Scholar
  194. Solovchenko AE (2012) Physiological role of neutral lipid accumulation in eukaryotic microalgae under stresses. Russ J Plant Physiol 59:167–176CrossRefGoogle Scholar
  195. Solovchenko AE (2013) Physiology and adaptive significance of secondary carotenogenesis in green microalgae. Russ J Plant Physiol 60:1–13CrossRefGoogle Scholar
  196. Sommer TR, D’Souza FML, Morrissy NM (1992) Pigmentation of adult rainbow trout, Oncorhynchus mykiss, using the green alga Haematococcus pluvialis. Aquaculture 106:63–74CrossRefGoogle Scholar
  197. Spangenberg B, Poole CF, Weins C (2011) Quantitative thin-layer chromatography: a practical survey. Springer, Heidelberg, 388 ppCrossRefGoogle Scholar
  198. Stahl E (1962) Dünnschicht-Chromatographie: Ein Laboratoriumshandbuch. Prepared by Bolliger HR, Brenner M, Gänshirt H, Mangold HK, Seiler H, Stahl E, Waldi D. Springer-Verlag, Berlin, 534 pp. (English translation available)Google Scholar
  199. Stauber JL, Jeffrey SW (1988) Photosynthetic pigments in fifty-one species of marine diatoms. J Phycol 24:158–172CrossRefGoogle Scholar
  200. Strand A, Herstad O, Liaaen-Jensen S (1998) Fucoxanthin metabolites in egg yolks of laying hens. Comp Biochem Physiol A 119:963–974CrossRefGoogle Scholar
  201. Stransky H, Hager A (1970) Das Carotinoidmuster und die Verbreitung des lichtinduzierten Xanthophyllcyclus in verschiedenen Algenklassen. II. Xanthophyceae. Arch Microbiol 71:164–190Google Scholar
  202. Sugimura R, Suda M, Sho A, Takahashi T, Sashima T, Abe M, Hosokawa M, Miyashita K (2012) Stability of fucoxanthin in dried Undaria pinnatifida (Wakame) and baked products (scones) containing wakame powder. Food Sci Technol Res 18:687–693CrossRefGoogle Scholar
  203. Sun N, Wang Y, Li Y-T, Huang J-C, Chen F (2008) Sugar-based growth, astaxanthin accumulation and carotenogenic transcription of heterotrophic Chlorella zofingiensis (Chlorophyta). Process Biochem 43:1288–1292CrossRefGoogle Scholar
  204. Suzuki M, Watanabe K, Fujiwara S, Kurasawa T, Wakabayashi T, Tsuzuki M, Iguchi K, Yamori T (2003) Isolation of peridinin-related norcarotenoids with cell growth-inhibitory activity from the cultured dinoflagellate of Symbiodinium sp., a symbiont of the Okinawan soft coral Clavularia viridis, and analysis of fatty acids of the dinoflagellate. Chem Pharm Bull 51:724–727PubMedCrossRefGoogle Scholar
  205. Suzuki K, Kuwata A, Yoshie N, Shibata A, Kawanobe K, Saito H (2011) Population dynamics of phytoplankton, heterotrophic bacteria, and viruses during the spring bloom in the western subarctic Pacific. Deep-Sea Res I 58:575–589CrossRefGoogle Scholar
  206. Sweeney BM (1976) Pedinomonas noctilucae (Prasinophyceae), the flagellate symbiotic in Noctiluca (Dinophyceae) in Southeast Asia. J Phycol 12:460–464Google Scholar
  207. Takaichi S, Mochimaru M, Uchida H, Murakami A, Hirose E, Maoka T, Tsuchiya T, Mimuro M (2012) Opposite chilarity [sic!] of α-carotene in unusual cyanobacteria with unique chlorophylls, Acaryochloris and Prochlorococcus. Plant Cell Physiol 53:1881–1888PubMedCrossRefGoogle Scholar
  208. Tang G, Russell RM (2009) Carotenoids as provitamin A. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 5, Nutrition and health. Birkhäuser Verlag, Basel, pp 149–172CrossRefGoogle Scholar
  209. Teimouri M, Amirkolaie AK, Yeganeh S (2013) The effects of Spirulina platensis meal as a feed supplement on growth performance and pigmentation of rainbow trout (Oncorhynchus mykiss). Aquaculture 396–399:14–19CrossRefGoogle Scholar
  210. Telfer A, Pascal A, Gall A (2008) Carotenoids in photosynthesis. In: Britton G, Liaaen-Jensen S, Pfander H (eds) Carotenoids, vol 4, Natural functions. Birkhäuser Verlag, Basel, pp 265–308CrossRefGoogle Scholar
  211. Urikura I, Sugawara T, Hirata T (2011) Protective effect of fucoxanthin against UVB-induced skin photoaging in hairless mice. Biosci Biotechnol Biochem 75:757–760PubMedCrossRefGoogle Scholar
  212. Vetter W, Englert G, Rigassi N, Schwieter U (1971) Spectroscopic methods. In: Isler O, Gutmann H, Solms U (eds) Carotenoids. Birkhäuser Verlag, Basel, pp 189–266CrossRefGoogle Scholar
  213. Vílchez C, Forján E, Cuaresma M, Bédmar F, Garbayo I, Vega JM (2011) Marine carotenoids: biological functions and commercial applications. Mar Drugs 9:319–333PubMedPubMedCentralCrossRefGoogle Scholar
  214. Wakahama T, Laza-Martínez A, Taha AIBHM, Okuyama H, Yoshida K, Kogame K, Awai K, Kawachi M, Maoka T, Takaichi S (2012) Structural confirmation of a unique carotenoid lactoside, P457, in Symbiodinium sp. strain NBRC 104787 isolated from a sea anemone and its distribution in dinoflagellates and various marine organisms. J Phycol 48:1392–1402CrossRefGoogle Scholar
  215. Walker TL, Purton S, Becker DK, Collet C (2005) Microalgae as bioreactors. Plant Cell Rep 24:629–641PubMedCrossRefGoogle Scholar
  216. Wang Y, Liu Z, Qin S (2013) Effects of iron on fatty acid and astaxanthin accumulation in mixotrophic Chromochloris zofingiensis. Biotechnol Lett 35:351–357PubMedCrossRefGoogle Scholar
  217. Watson SB (2003) Cyanobacterial and eukaryotic algal odour compounds: signals or by-products? A review of their biological activity. Phycologia 42:332–350CrossRefGoogle Scholar
  218. Weesepoel Y, Vincken J-P, Pop RM, Liu K, Gruppen H (2013) Sodiation as a tool for enhancing the diagnostic value of MALDI-TOF/TOF-MS spectra of complex astaxanthin ester mixtures from Haematococcus pluvialis. J Mass Spectrom 48:862–874PubMedCrossRefGoogle Scholar
  219. Yacobi YZ (2003) Seasonal variation in pigmentation of the dinoflagellate Peridinium gatunense (Dinophyceae) in Lake Kinneret, Israel. Freshw Biol 48:1850–1858CrossRefGoogle Scholar
  220. Yacobi YZ, Ostrovsky I (2008) Downward flux of organic matter and pigments in Lake Kinneret (Israel): relationships between phytoplankton and the material collected in sediment traps. J Plankton Res 30:1189–1202CrossRefGoogle Scholar
  221. Yokohama Y (1981) Distribution of the green light-absorbing pigments siphonaxanthin and siphonein in marine green algae. Bot Mar 24:637–640Google Scholar
  222. Yokohama Y (1983) A xanthophyll characteristic of deep-water green algae lacking siphonaxanthin. Bot Mar 26:45–48CrossRefGoogle Scholar
  223. Yokohama Y, Hirata T, Misonou T, Tanaka J, Yokochi H (1992) Distribution of green light-harvesting pigments, siphonaxanthin and siphonein, and their precursors in marine green algae. Jpn J Phycol 40:25–31Google Scholar
  224. Yoshii Y, Takaichi S, Maoka T, Inouye I (2003) Photosynthetic pigment composition in the primitive green alga Mesostigma viride (Prasinophyceae): phylogenetic and evolutionary implications. J Phycol 39:570–576CrossRefGoogle Scholar
  225. Yoshii H, Yoshii Y, Asai T, Furukawa T, Takaichi S, Fujibayashi Y (2012) Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production. Biochem Biophys Res Commun 417:640–645PubMedCrossRefGoogle Scholar
  226. Young A (1993) Factors that affect the carotenoid composition of higher plants and algae. In: Young A, Britton G (eds) Carotenoids in photosynthesis. Chapman and Hall, London, pp 160–205CrossRefGoogle Scholar
  227. Young A, Britton G (eds) (1993) Carotenoids in photosynthesis. Chapman and Hall, London, 498 ppGoogle Scholar
  228. Zapata M, Jeffrey SW, Wright SW, Rodríguez F, Garrido JL, Clementson L (2004) Photosynthetic pigments in 37 species (65 strains) of Haptophyta: implications for oceanography and chemotaxonomy. Mar Ecol Prog Ser 270:83–102CrossRefGoogle Scholar
  229. Zapata M, Fraga S, Rodríguez F, Garrido JL (2012) Pigment-based chloroplast types in dinoflagellates. Mar Ecol Prog Ser 465:33–52CrossRefGoogle Scholar
  230. Zhao Y, Guan F, Wang G, Miao L, Ding J, Guan G, Li Y, Hui B (2011) Astaxantin preparation by lipase-catalyzed hydrolysis of its esters from Haematococcus pluvialis algal extracts. J Food Sci 76:C643–C650PubMedCrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.Faculty of Biosciences and AquacultureUniversity of NordlandBodøNorway

Personalised recommendations