Fatty acids and oxylipins as semiochemicals

Lipids in Aquatic Ecosystems

Volumn 9780387893662, Issue , 2009, Pages 65-92

  Watson, Susan B ^a   Caldwell, Gary ^a,b   Pohnert, Georg ^a,c  

^a ENVIRONMENT CANADA   (Canada)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

^c EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951802670     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-0-387-89366-2_4     Document Type: Chapter

References (148)

1. Adolph, S., Poulet, S. A., and Pohnert, G. 2003. Synthesis and biological activity of a, b, g, dunsaturated aldehydes from diatoms. Tetrahedron 59:3003-3008.
2. Adolph, S., Bach, S., Blondel, M., Cueff, A., Moreau, M., Pohnert, G., Poulet, S., Wichard, T., and Zuccaro, A. 2004. Cytotoxicity of diatom-derived oxylipins in organisms belonging to different phyla. J. Exp. Biol. 207:2935-2946.
3. Alekseev, V. and Lampert, W. 2001. Maternal control of resting-egg productoin in Daphnia. Nature 414:899-900.
4. Ban, S. H. 1994. Effect of temperature and food concentration on post-embryonic development, egg production and adult body size of the calanoid copepod Eurytemora affinis. J. Plankton Res. 16:721-735.
5. Ban, S., Burns, C., Castel, J., Chaudron, Y., Christou, E., Escribano, R., Umani, S. F., Gasparini, S., Ruiz, F. G., Hoffmeyer, M., Ianora, A., Kang, H. K., Laabir, M., Lacoste, A., Miralto, A., Ning, X., Poulet, S., Rodriguez, V., Runge, J., Shi, J., Starr, M., Uye, S., and Wang, Y. 1997. The paradox of diatom-copepod interactions. Mar. Ecol. Prog. Ser. 157:287-293.
6. Barofsky, A., and Pohnert, G. 2007. Biosynthesis of polyunsaturated short chain aldehydes in the diatom Thalassiosira rotula. Org. Lett. 9:1017-1020.
7. Barreiro, A., Guisande, C., Maneiro, I., Vergara, A. R., Riveiro, I., and Iglesias, P. 2007. Zooplankton interactions with toxic phytoplankton: some implications for food web studies and algal defense strategies of feeding selectivity behaviour, toxin dilution and phytoplankton population diversity. Acta Oecol. 32:279-290.
8. Bell, M. V., Dick, J. R., Thrush, M., and Navarro, J. C. 1996. Decreased 20:4n-6/20:5n-3 ratio in sperm from cultured sea bass, Dicentrarchus labrax, broodstock compared with wild fish. Aquaculture 144:189-199.
9. Boland, W. 1995. The chemistry of gamete attraction: chemical structures, biosynthesis, and abiotic degradation of algal pheromones. Proc. Natl Acad. Sci. U. S. A. 92:37-43.
10. Boland, W., Marner, F., Jaenicke, L., Mueller, D., and Foelster, E. 1983. Comparative receptor study in gamete chemotaxis of the seaweeds Ectocarpus siliculosus and Cutleria multifida: an approach to interspecific communication of algal gametes. Eur. J. Biochem. 134:97-104.
11. Bottrell, H. H., Duncan, A., Gliwics, Z. M., Grygierek, E., and Herzig, A. 1976. A review of some problems in zooplankton production. Norw. J. Zool. 24:419-456.
12. Bradow, J., and Connick, J. W. 1990. Volatile seed germination inhibitors from plant residues. J. Chem. Ecol. 16:645-667.
13. Bricelj, V. M., Connell, L., Konoki, K., MacQuarrie, S. P., Scheuer, T., Catterall, W. A., and Trainer, V. L. 2005. Sodium channel mutation leading to saxitoxin resistance in clams increases risk of PSP. Nature 434:763-767.
14. Bury, N. R., Codd, G. A., Bonga, S. E. W., and Flik, G. 1998. Fatty acids from the cyanobacterium Microcystis aeruginosa with potent inhibitory effects on fish gill Na +/K+-ATPase activity. J. Exp. Biol. 201:81-89.
15. Caldwell, G. S., Olive, P. J. W., and Bentley, M. G. 2002. Inhibition of embryonic development and fertilization in broadcast spawning marine invertebrates by water soluble diatom extracts and the diatom toxin 2-trans, 4-trans decadienal. Aquat. Toxicol. 60:123-137.
16. Caldwell, G. S., Bentley, M. G., and Olive, P. J. W. 2004a. First evidence of sperm motility inhibition by the diatom aldehyde 2E, 4E-decadienal. Mar. Ecol. Prog. Ser. 273:97-108.
17. Caldwell, G. S., Watson, S. B., and Bentley, M. G. 2004b. How to assess toxin ingestion and postingestion partitioning in zooplankton? J. Plankton Res. 26:1369-1377.
18. Caldwell, G. S., Lewis, C., Olive, P. J. W., and Bentley, M. G. 2005. Exposure to 2, 4-decadienal negatively impacts upon marine invertebrate larval fitness. Mar. Environ. Res. 59:405-417.
19. Camazine, S. M., Resch, J. F., Eisner, T., and Meinwald, J. 1983. Mushroom chemical defense: pungent sesquiterpenoid dialdehyde antifeedant to opossum. J. Chem. Ecol. 9:1439-1447.
20. Carotenuto, Y., and Lampert, W. 2004. Ingestion and incorporation of freshwater diatoms by Daphnia pulicaria: do morphology and oxylipin production matter? J. Plankton Res. 26:563-569.
21. Carotenuto, Y., Wichard, T., Pohnert, G., and Lampert, W. 2005. Life-history responses of Daphnia pulicaria to diets containing freshwater diatoms: effects of nutritional quality versus polyunsaturated aldehydes. Limnol. Oceanogr. 50:449-454.
22. Casotti, R., Mazza, S., Brunet, C., Vantrepotte, V., Ianora, A., and Miralto, A. 2005. Growth inhibition and toxicity of the diatom aldehyde 2-trans, 4-trans-decadienal on Thalassiosira weissflogii (Bacillariophyceae). J. Phycol. 41:7-20.
23. Cavill, G. W. K., and Hinterberger, H. 1960. The chemistry of ants IV. Terpenoid constituents of some Dolichoderus and Iridomyrmex species. Aust. J. Chem. 13:514-519.
24. Cembella, A. D. 2003. Chemical ecology of eukaryotic microalgae in marine ecosystems. Phycologia 42:420-447.
25. Charnov, E. L. 1997. Trade-off-invariant rules for evolutionary stable life histories. Nature 387:3993-3994.
26. Chaudron, Y., Poulet, S. A., Laabir, M., Ianora, A., and Miralto, A. 1996. Is hatching success of copepod eggs diatom density-dependent? Mar. Ecol. Prog. Ser. 144:185-193.
27. Chen, W. H., and Folt, C. L. 1993. Measures of food quality as demographic predictors in freshwater copepods. J. Plankton Res. 15:1247-1261.
28. Chiang, I. Z., Huang, W. Y., and Wu, J. T. 2004. Allelochemicals of Botryococcus braunii (Chlorophyceae). J. Phycol. 40:474-480.
29. Chuecas, L., and Riley, J. P. 1969. Component fatty acids of the total lipids of some marine phytoplankton. J. Mar. Biol. Ass. U. K. 49:97-116.
30. Clare, A. S., and Walker, G. 1986. Further studies on the control of the hatching process in Balanus balanoides (L). J. Exp. Mar. Biol. Ecol. 97:295-304.
31. Cook, H. W. 1996. Fatty acid desaturation and chain elongation in eukaryotes, pp. 129-152. In D. E. Vance and J. E. Vance (eds.), Biochemistry of Lipids, Lipoproteins and Membranes. Elsevier, Amsterdam.
32. Cook, A., and Elvidge, J. 1951. Fertilization in the Fucaceae: investigations of the nature of the chemotacatic substance produced by eggs of Fucus serratus and Fvesiculosus. Proc. R. Soc. Lond. Ser. B 138:97-114.
33. Cutignano, A., d'Ippolito, G., Romano, G., Lamari, N., Cimino, G., Febbraio, F., Nucci, R., and Fontana, A. 2006. Chloroplastic glycolipids fuel aldehyde biosynthesis in the marine diatom Thalassiosira rotula Chem. BioChem. 7:450-456.
34. Derenbach, J. B., and Pesando, D. 1986. Investigations into a small fraction of volatile hydrocarbons. iii. Two diatom cultures produce ectocarpene, a pheromone of brown algae. Mar. Chem. 19:337-342.
35. Dicke, M., and Sabelis, M. W. 1988. Infochemical terminology: based on cost-benefit analysis rather than origin of compounds? Funct. Ecol. 2:131-139.
36. Di Marzo, V., De Petrocellis, L., Gianfrani, C., and Cimino, G. 1993. Biosynthesis, structure and biological activity of hydroxyeicosatetraenoic acids in Hydra vulgaris. Biochem. J. 295:23-29.
37. Dittberner, U., Eisenbrand, G., and Zankl, H. 1995. Genotoxic effects of the a, b-unsaturated aldehydes 2-trans-butenal, 2-trans-hexenal and 2-trans, 6-cis-nonadienal. Mutat. Res. 335:259-265.
38. Dutz, J., Koski, M., and Jonasdottir, S. H. 2008. Copepod reproduction is unaffected by diatom aldehydes or lipid composition. Limnol. Oceanogr. 53:225-235.
39. Feussner, I., and Wasternack, C. 2002. The lipoxygenase pathway. Ann. Rev. Plant Biol. 53:275-297.
40. Findlay, J. A., and Patil, A. D. 1984. Antibacterial constituents of the diatom Navicula delognei. J. Nat. Prod. 47:815-818.
41. Fink, P., von Elert, E., and Jüttner, F. 2006. Volatile foraging kairomones in the littoral zone: attraction of an herbivorous freshwater gastropod to algal odors. J. Chem. Ecol. 32:1867-1831.
42. Fontana, A., d'Ippolito, G., Cutignano, A., Romano, G., Lamari, N., Gallucci, A. M., Cimino, G., Miralto, A., and Ianora, A. 2007. LOX-induced Lipid peroxidation mechanism responsible for the detrimental effect of marine diatoms on zooplankton grazers. Chembiochem: A European Journal of Chemical Biology 8:1810-1818.
43. Fu, M., Koulman, A., Van Rijssel, M., Luetzen, A., De Boer, M. K., Tyl, M. R., and Liebezeit, G. 2004. Chemical characterisation of three haemolytic compounds from the microalgal species Fibrocapsa japonica (Raphidophyceae). Toxicon 43:355-363.
44. Gerwick, W. H. 1994. Structure and biosynthesis of marine algal oxylipins. Biochim. Biophys. Acta 1211:243-255
45. Guisande, C., Maneiro, I., and Riveiro, I. 1999. Homeostasis in the essential amino acid composition of the marine copepod Euterina acutifrons. Limnol. Oceanogr. 44:691-696.
46. Hairston, N. G., Holtmeier, C. L., Lampert, W., Weider, L. J., Post, D. M., Fischer, J. M., Caceres, C. E., Fox, J. A., and Gaedke, U. 2001. Natural selection for grazer resistance to toxic cyanobacteria: evolution of phenotypic plasticity? Evolution 55:2203-2214.
47. Hansen, L. R., Kristiansen, J., and Rasmussen, J. V. 1994. Potential toxicity of the freshwater Chrysochromulina species C. parva (Prymnesiophyceae). Hydrobiologia 287:157-159.
48. Hansen, E., Even, Y., and Genevière, A. M. 2004a. The a, b, g, d-unsaturated aldehyde 2-trans-4-trans-decadienal disturbs DNA replication and mitotic events in early sea urchin embryos. Toxicol. Sci. 81:190-197.
49. Hansen, E., Ernstsen, A., and Eilertsen, H. C. 2004b. Isolation and characterisation of a cytotoxic polyunsaturated aldehyde from the marine phytoplankter Phaeocystis pouchetii (Hariot) Lagerheim. Toxicology 199:207-217.
50. Harrison, K. E. 1990. The role of nutrition in maturation, reproduction and embryonic development of decapod crustaceans: a review. J. Shellfish Res. 9:1-28.
51. Hombeck, M., and Boland, W. 1998. Biosynthesis of the algal pheromone fucoserratene by the freshwater diatom Asterionella formosa (Bacillariophyceae). Tetrahedron 54:11033-11042.
52. Hombeck, M., Pohnert, G., and Boland, W. 1999. Biosynthesis of dictyopterene A: stereoselectivity of a lipoxygenase/hydroperoxide lyase from Gomphonema parvulum (Bacillariophyceae). Chem. Commun. 3:243-244.
53. Huntley, M. E. 1982. Yellow water in La Jolla Bay, California, July 1980. II. Suppression of zooplankton grazing. J. Exp. Mar. Biol. Ecol. 63:81-91.
54. Huntley, M., Sykes, P., Rohan, S., and Marin, V. 1986. Chemically mediated rejection of dinoflagellate prey by the copepods Calanus pacificus and Paracalanus parvus - mechanism, occurrence and significance. Mar. Ecol. Prog. Ser. 28:105-120.
55. Ianora, A., Miralto, A., and Poulet, S. A. 1999. Are diatoms good or toxic for copepods? Reply to comment by Jónasdottir et al. Mar. Ecol. Prog. Ser. 177:305-308.
56. Ianora, A., Miralto, A., Poulet, S. A., Carotenuto, Y., Buttino, I., Romano, G., Casotti, R., Pohnert, G., Wichard, T., Colucci-D'Amato, L., Terrazzano, G., and Smetacek, V. 2004. Aldehyde suppression of copepod recruitment in blooms of a ubiquitous planktonic diatom. Nature 429:403-407.
57. Ikawa, M., Haney, J. F., and Sasner, J. J. 1996. Inhibition of Chlorella growth by the lipids of cyanobacterium Microcystis aeruginosa. Hydrobiologia 331:167-170.
58. d'Ippolito, G., Romano, G., Caruso, T., Spinella, A., Cimino, G., and Fontana, A. 2003. Production of octadienal in the marine diatom Skeletonema costatum. Organ. Lett. 5:885-887.
59. d'Ippolito, G., Tucci, S., Cutignano, A., Romano, G., Cimino, G., Miralto, A., and Fontana, A. 2004. The role of complex lipids in the synthesis of bioactive aldehydes of the marine diatom Skeletonema costatum. Biochim Biophys. Acta 1686:100-107.
60. d'Ippolito, G., Cutignano, A., Briante, R., Febbraio, F., Cimino, G., and Fontana, A. 2005. New C-16 fatty-acid-based oxylipin pathway in the marine diatom Thalassiosira rotula. Org. Biomol. Chem. 3:4065-4070.
61. d'Ippolito, G., Cutignano, A., Tucci, S., Romano, G., Cimino, G., and Fontana, A. 2006. Biosynthetic intermediates and stereochemical aspects of aldehyde biosynthesis in the marine diatom Thalassiosira rotula. Phytochemistry 67:314-322.
62. Irigoien, X., Harris, R. P., Verheye, H. M., Joly, P., Runge, J., Starr, M., Pond, D., Campbell, R., Shreeve, R., Ward, P., Smith, A. N., Dam, H. G., Peterson, W., Tirelli, V., Koski, M., Smith, T., Harbour, D., and Davidson, R. 2002. Copepod hatching success in marine ecosystems with high diatom concentrations. Nature 419:387-389.
63. Jeckel, W. H., de Moreno, J. E. A., Oreno, V., and Moreno, V. J. 1989. Biochemical composition, lipid classes and fatty acids in the male reproductive system of the shrimp Pleoticus muelleri Bate. Comp. Biochem. Physiol. B 93:807-811.
64. Jónasdóttir, S. H., and Kiørboe, T. 1996. Copepod recruitment and food composition: do diatoms affect hatching success? Mar. Biol. 125:743-750.
65. Jones, R. H., and Flynn, K. J. 2005. Nutritional status and diet composition affect the value of diatoms as copepod prey. Science 307:1457-1459.
66. Jüttner, F. 1981. Detection of lipid degradation products in the water of a reservoir during a bloom of Synura uvella. Appl. Environ. Microbiol. 41:100-106.
67. Jüttner, F. 1984. Dynamics of the volatile organic substances associated with cyanobacteria and algae in a eutrophic shallow lake. Appl. Environ. Microbiol. 47:815-820.
68. Jüttner, F. 1992. Flavour compounds in weakly polluted rivers as a means to differentiate pollution sources. Water Sci. Technol. 25:155-164.
69. Jüttner, F. 1995. Physiology and biochemistry of odourous compounds from freshwater cyanobacteria and algae. Water Sci. Technol. 31:69-78.
70. Jüttner, F. 2001. Liberation of 5, 8, 11, 14, 17-eicosapentaenoic acid and other polyunsaturated fatty acids from lipids as a grazer defense reaction in epilithic diatom biofilms. J. Phycol. 37:744-755.
71. Jüttner, F. 2005. Evidence that polyunsaturated aldehydes of diatoms are repellents for pelagic crustacean grazers. Aquatic Ecol. 39:271-282.
72. Jüttner, F., and Müller, H. 1979. Excretion of octadiene and octatrienes by a freshwater diatom. Naturwissenschaften 66:363-364.
73. Jüttner, F., and Dürst, U. 1997. High lipoxygenase activities in epilithic biofilms of diatoms. Archiv. Hydrobiol. 138:451-463.
74. Jüttner, F., Hoflacher, B., and Wurster, K. 1986. Seasonal analysis of volatile organic biogenic substances in freshwater phytoplankton populationsdominated by Dinobryon Microcystis and Aphanizomenon. J. Phycol. 22:169-175.
75. Kainz, M., Arts, M. T., and Mazumder, A. 2004. Essential fatty acids in the planktonic food web and their ecological role for higher trophic levels. Limnol. Oceanogr. 49:1784-1793.
76. Kamiya, H., Naka, K., and Hashimoto, K. 1979. Ichthyotoxicity of a flagellate Uroglena volvox Bull. Jpn Soc. Sci. Fish. 45:129.
77. Kieber, R., Hydro, L., and Seaton, P. 1997. Photooxidation of triglycerides and fatty acids in seawater: implication toward the formation of marine humic substances. Limnol. Oceanogr. 42:1454-1462.
78. Kleppel, G. S. 1993. On the diets of calanoid copepods. Mar. Ecol. Prog. Ser. 99:183-195.
79. Koski, M., Wichard, T., and Jónasdóttir, S. 2008. "Good" and "bad" diatoms: development, growth and juvenile mortality of the copepod Temora longicornis on diatom diets. Mar. Biol. 154:719-734.
80. Kubo, I., Lee, Y.-W., Pettei, M., Pilkiewicz, F., and Nakanishi, K. 1976. Potent army worm antifeedants from the east African Warburgia plants. Chem. Commun. 24:1013-1014.
81. Laabir, M., Poulet, S. A., Ianora, A., Miralto, A., and Cueff, A. 1995. Reproductive response of Calanus helgolandicus. II. In situ inhibition of embryonic development. Mar. Ecol. Prog. Ser. 129:97-105.
82. Laabir, M., Poulet, S. A., Cueff, A., and Ianora, A. 1999. Effect of diet on levels of amino acids during embryonic and naupliar development of the copepod Calanus helgolandicus. Mar. Biol. 134:89-98.
83. La Montagne, J. M., and McCauley, E. 2001. Maternal effects in Daphnia: what mothers are telling their offspring and do they listen? Ecol. Lett. 4:64-71.
84. Leeper, D. A., and Porter, K. G. 1995. Toxicity of the mixotrophic chrysophyte Poterioochromonas malhamensis to the cladoceran Daphnia ambigua. Arch. Hydrobiol. 134:207-222.
85. Lewis, C., Caldwell, G. S., Bentley, M. G., and Olive, P. J. W. 2004. Effects of a bioactive diatomderived aldehyde on developmental stability in Nereis virens (Sars) larvae: an analysis using fluctuating asymmetry. J. Exp. Mar. Biol. Ecol. 304:1-16.
86. Lincoln, J. A., Turner, J. T., Bates, S. S., Leger, C., and Gauthier, D. A. 2001. Feeding, egg production, and egg hatching success of the copepods Acartia tonsa and Temora longicornis on diets of the toxic diatom Pseudo-nitzschia multiseries and the non-toxic diatom Pseudo-nitzschia pungens Hydrobiologia 453:107-120.
87. Loureiro, A. P. M., Di Masco, P., Gomes, O. F., and Medeiros, M. H. G. 2000. trans, trans-2, 4-Decadienal-induced 1, N-2-etheno-2'-deoxyguanosine adduct formation. Chem. Res. Toxicol. 13:601-609.
88. Mann, D. 1999. The species concept in diatoms. Phycologia 38:437-495.
89. Matsui, K. 2006. Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism. Curr. Opin. Plant Biol. 9:274-280.
90. Matsutani, T., and Nomura, T. 1987. In vitro effects of serotonin and prostaglandins on release of eggs from the ovary of the scallop, Patinopecten yessoensis. Gen. Comp. Endocrinol. 67:111-118.
91. McGrattan, D., Sullivan, J., and Ikawa, M. 1976. Inhibition of Chlorella (Chlorophyceae) growth by fatty acids, using the paper disk method. J. Phycol. 12:129-131.
92. Meijer, L., Brash, A., Bryant, R., Ng, K., Maclouf, J., and Sprecher, H. 1986. Stereospecific induction of starfish oocyte maturation by (8r)-hydroxyeicosatetraenoic acid. J. Biol. Chem. 261:7040-7047.
93. Miralto, A., Barone, G., Romano, G., Poulet, S., Ianora, A., Russo, G., Buttino, I., Mazzarella, G., Laabir, M., Cabrini, M., and Giacobbe, M. 1999. The insidious effect of diatoms on copepod reproduction. Nature 402:173-176.
94. Morimoto, M., Tanimoto, K., Sakatani, A., and Komai, K. 2002. Antifeedant activity of an anthraquinone aldehyde in Galium aparine L.against Spodoptera litura. Phytochemistry 60:163-166.
95. Murakami, M., Makebe, K., Yamaguchi, K., and Konosu, S. 1989. Cytotoxic polyunsaturated fatty acid from Pediastrum. Phytochemistry 28:625-626.
96. Okamoto, T., and Katoh, S. 1977. Linolenic acid binding by chloroplasts. Plant Cell Physiol. 18:539-550.
97. Okamoto, T., Katoh, S., and Murakuami, S. 1977. Effects of linolenic acid on spinach chloroplast structure. Plant Cell Physiol. 18:551-560.
98. Olive, P. J. W. 1992. The adaptive significance of seasonal reproduction in marine invertebrates: the importance of distinguishing between models. Invertebr. Reprod. Dev. 22:165-174.
99. Paffenhöfer, G. A., Ianora, A., Miralto, A., Turner, J., Kleppel, G. S., Ribera d'Alcalà, M., Casotti, R., Caldwell, G., Pohnert, G., Fontana, A., Müller-Navarra, D., Jónasdóttir, S., Armbrust, V., Båmstedt, U., Ban, S., Bentley, M. G., Boersma, M., Bundy, M., Buttino, I., Calbet, A., Carlotti, F., Carotenuto, Y., d'Ippolito, G., Frost, B., Guisande, C., Lampert, W., Lee, R., Mazza, S., Mazzocchi, M., Nejstgaard, J. C., Poulet, S. A., Romano, G., Smetacek, V., Uye, S., Wakeham, S., Watson, S., and Wichard, T. 2005. Colloquium on diatom-copepod interactions. 2005. Mar. Ecol. Prog. Ser. 286:293-305.
100. Pohnert, G. 2000. Wound-activated chemical defense in unicellular planktonic algae. Angew. Chem. Int. Ed. Engl. 39:4352-4354.
101. Pohnert, G. 2002. Phospholipase A2 activity triggers the wound-activated chemical defense in the diatom Thalassiosira rotula. Plant Physiol. 129:103-111.
102. Pohnert, G. 2005. Diatom/copepod interactions in plankton: the indirect chemical defense of unicellular algae. Chem. BioChem. 6:946-959.
103. Pohnert, G., and Boland, W. 1996. Biosynthesis of the algal pheromone hormosirene by the freshwater diatom Gomphonema parvulum (Bacillariophyceae). Tetrahedron 52:10073-10082.
104. Pohnert, G., and Boland, W. 2002. The oxylipin chemistry of attraction and defense in brown algae and diatoms. Nat. Prod. Rep. 19:108-122.
105. Pohnert, G., Adolph, S., and Wichard, T. 2004. Short synthesis of labeled and unlabeled 6Z, 9Z, 12Z, 15-hexadecatetraenoic acid as metabolic probes for biosynthetic studies on diatoms. Chem. Phys. Lipids 131:159-166.
106. Poulet, S. A., and Marsot, P. 1978. Chemosensory grazing by calanoid copepods (Arthropoda: Crustacea). Science 200:1403-1405.
107. Poulet, S. A., Ianora, A., Miralto, A., and Meijer, L. 1994. Do diatoms arrest embryonic development in copepods? Mar. Ecol. Prog. Ser. 111:79-86.
108. Poulet, S. A., de Forges, M. R., Cueff, A., and Lennon, J. F. 2003. Double-labelling methods used to diagnose apoptotic and necrotic cell degradations in copepod nauplii. Mar. Biol. 143:889-895.
109. Poulet, S. A., Cueff, A., Wichard, T., Marchetti, J., Dancie, C., and Pohnert, G. 2007. Influence of diatoms on copepod reproduction. III. Consequences of abnormal oocyte maturation on reproductive factors in Calanus helgolandicus. Mar. Biol.. 152:415-428.
110. Reinikainen, M., Meriluoto, J. A. O., Spoof, L., and Harada, K. 2001. The toxicities of a polyunsaturated fatty acid and a microcystin to Daphnia magna. Exp. Toxicol. 16:444-448.
111. Rengefors, K., and Legrande, C. 2001. Toxicity in P eridinium aciculiferum - an adaptive strategy to outcompete other winter phytoplankton? Limnol. Oceanogr. 46:1990-1997.
112. Ribalet, F., Wichard, T., Pohnert, G., Ianora, A., Miralto, A., and Casotti, R. 2007a. Age and nutrient limitation enhance polyunsaturated aldehyde production in marine diatoms. Phytochemistry 68:2059-2067.
113. Ribalet, F., Berges, J. A., Ianora, A., Casotti, R. 2007b. Growth inhibition of cultured marine phytoplankton by toxic algal-derived polyunsaturated aldehydes. Aquat. Toxicol. 85:219-227.
114. Romano, G., Russo, G. L., Buttino, I., Ianora, A., and Miralto, A. 2003. A marine diatom-derived aldehyde induces apoptosis in copepod and sea urchin embryos. J. Exp. Biol. 2006:3487-3494.
115. Rukmini, C. 1990. Reproductive toxicology and nutritional studies on manhua oil (Madhuca latifolia). Food Chem. Toxicol. 28:601-605.
116. Sandgren C. 1988. The ecology of chrysophyte flagellates: their growth and perenniation strategies as freshwater phytoplankton, pp. 99-105. In Sandgren C. (ed.), Growth and Reproductive Strategies of Freshwater Phytoplankton. Cambridge University Press, Cambridge.
117. Schnitzler, I., Pohnert, G., Hay, M., and Boland, W. 2001. Chemical defense of brown algae (Dictyopteris spp.) against the herbivorous amphipod Ampithoe longimana. Oecologia 126:515-521.
118. Schuel, H., Moss, R., and Schuel, R. 1985. Induction of polyspermic fertilization in sea urchins by the leukotriene antagonist FPL-55712 and the 5-lipoxygenase inhibitor BW755C. Gamete Res. 11:41-50.
119. Scutt, J. 1964. Autoinhibition production by Chorella vulgaris. Am. J. Bot. 51:581-584.
120. Sellem, F., Pesando, D., Bodennec, G., El Abed, A., and Girard, J. P. 2000. Toxic effects of Gymnodinium cf.mikimotoi unsaturated fatty acids to gametes and embryos of the seaurchin Paracentrotus lividus. Water Res. 34:550-556.
121. Shilo, M. 1981. The toxic principles of Prymnesium parvum, pp. 37-47. In W. W. Carmichael (ed.), Algal Toxins and Health. Plenum, New York.
122. Stanley-Samuelson, D. W. 1994. The biological significance of prostaglandins and related eicosanoids in invertebrates. Am. Zool. 34:589-598.
123. Støttrup, J. G., and Jensen, J. 1990. Influence of algal diet on feeding and egg production of the calanoid copepod Acartia tonsa Dana. J. Exp. Mar. Biol. Ecol. 141:87-105.
124. Taylor, F. J. R. 1985. The taxonomy and relationships of red tide flagellates, pp. 11-26. In D. Anderson, A. White, and D. Baden (eds.), 3rd International Conference on Toxic Dinoflagellates. Elsevier, New York.
125. Tosti, E., Romano, G., Buttino, I., Cuomo, A., Ianora, A., and Miralto, A. 2003. Bioactive aldehydes from diatoms block the fertilization current in ascidian oocytes. Mol. Reprod. Dev. 66:72-80.
126. Trombetta, D., Saija, A., Bisignano, G., Arena, S., Caruso, S., Mazzanti, G., Uccella, N., and Castelli, F. 2002. Study on the mechanisms of the antibacterial action of some plant alpha, betaunsaturated aldehydes. Lett. Appl. Microbiol. 35:285-290.
127. Tsubo, Y. 1961. Chemotaxis and sexual behavior in Chlamydomonas. J. Protozool. 8:114-121.
128. Vardi, A., Formiggini, F., Casotti, R., Martino, A., Ribalet, F., Miralto, A., and Bowler, C. 2006. A stress surveillance system based on calcium and nitric oxide in marine diatoms. PLOS Biol. 4:411-419.
129. Walton, W., and Sandgren, C. 1995. The influence of zooplankton herbivory on the biogeography of chrysophyte algae, pp. 269-302. In C. Sandgren, J. Smol, and J. Kristiansen (eds.), Chrysophyte Algae. Cambridge University Press, Cambridge.
130. Watson, S. B. 2003. Cyanobacterial and eukaryotic algal odour compounds: signals or by-products? A review of their biological activity. Phycologia 42:332-350.
131. Watson, S. B., and Satchwill, T. 2003. Chrysophyte odour production: the impact of resources at the cell and population levels. Phycologia 42:393-405.
132. Watson, S. B., Satchwill, T., and McCauley, E. 2000. Drinking water taste and odour: a chrysophyte perspective. Nova Hedwigia 122:119-146.
133. Watson, S. B., Satchwill, T., and McCauley, E. 2001. Under-ice blooms and source-water odour in a nutrient-poor reservoir: biological, ecological and applied perspectives. Freshwater Biol. 46:1-15.
134. Watson, S. B., Jüttner, F., and Köster, O. 2007. Daphnia behavioural responses to taste and odour compounds: ecological significance and application as an inline treatment plant monitoring tool. Water Sci. Technol. 55:23-31.
135. Wee, J. L., Harris, S. A., Smith, J. P., Dionigi, C. P., and Millie, D. F. 1994. Production of the taste/odour compound, trans-2, cis-6-nonadienal within the Synurophyceae. J. Appl. Phycol. 6:365-369.
136. Wendel, T., and Jüttner, F. 1996. Lipoxygenase-mediated formation of hydrocarbons and unsaturated aldehydes in freshwater diatoms. Phytochemistry 41:1445-1449.
137. White, A. W. 1981. Marine zooplankton can accumulate and retain dinoflagellate toxins and cause fish kills. Limnol. Oceanogr. 26:103-109.
138. Wichard, T., and Pohnert, G. 2006. Formation of halogenated medium chain hydrocarbons by a lipoxygenase/hydroperoxide halolyase-mediated transformation in planktonic microalgae. J. Am. Chem. Soc. 128:7114-7115.
139. Wichard, T., Gobel, C., Feussner, I., and Pohnert, G. 2005a. Unprecedented lipoxygenase/hydroperoxide lyase pathways in the moss Physcomitrella patens. Angew. Chem. Int. Ed. Engl. 44:158-161.
140. Wichard, T., Poulet, S., Halsband-Lenk, C., Albaina, A., Harris, R., Liu, D., and Pohnert, G. 2005b. Survey of the chemical defense potential of diatoms: screening of fifty one species for a, β, λ, δ unsaturated aldehydes. J. Chem. Ecol. 31:949-958.
141. Wichard, T., Poulet, S. A., and Pohnert, G. 2005c. Determination and quantification of alpha, beta, gamma, delta-unsaturated aldehydes as pentafluorobenzyl-oxime derivates in diatom cultures and natural phytoplankton populations: application in marine field studies. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci. 814:155-161.
142. Wichard, T., Gerecht, A., Boersma, M., Poulet, S. A., Wiltshire, K., and Pohnert, G. 2007. Lipid and fatty acid composition of diatoms revisited: rapid wound-activated change of food quality parameters influences herbivorous copepod reproductive success. Chembiochem: A European Journal of Chemical Biology 8:1146-1153.
143. Wichard, T., Poulet, S. A., Boulesteix, A. L., Ledoux, J. B., Lebreton, B., Marchetti, J., and Pohnert, G. 2008. Influence of diatoms on copepod reproduction. II. Uncorrelated effects of diatom-derived α, η, χ, δ-unsaturated aldehydes and polyunsaturated fatty acids on Calanus helgolandicus in the field. Prog. Oceanogr. 77:30-44.
144. Wood, W. F. 1983. Chemical ecology: chemical communication in nature. J. Chem. Ed. 60:531-539.
145. Wu, J. T., Chiang, Y. R., Huang, W. Y., and Jane, W. N. 2006. Cytotoxic effects of free fatty acids on phytoplankton algae and cyanobacteria. Aquat. Toxicol. 80:338-345.
146. Yamada, N., Murakami, N., Kawamura, N., and Sakakibara, J. 1994. Mechanism of an early lysis by fatty acids from axenic Phormidium tenue (musty odor-producing cyanobacterium) and its growth prolongation by bacteria. Biol. Pharm. Bull. 17:1277-1281.
147. Yasumoto, T., Underdal, B., Aune, T., Hormazabal, V., Skulberg, O. M., and Oshima, Y. 1990. Screening for hemolytic and ichthyotoxic components of Chrysochromulina polylepis and Gyrodinium aureolum from Norwegian coastal waters, pp. 436-440. In E. Graneli, B. Sundström, L. Edler, and D. M. Anderson (eds.), 4th International Conference on Toxic Marine Phytoplankton. Elsevier, New York.
148. Yongmanitchai, W., and Ward, O. P. 1991. Screening of algae for potential alternative sources of eicosapentaenoic acid. Phytochemistry 31:2963-2967.