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Fatty Acids from Lipids of Marine Organisms: Molecular Biodiversity, Roles as Biomarkers, Biologically Active Compounds, and Economical Aspects

  • Jean-Pascal BergéEmail author
  • Gilles Barnathan
Chapter
Part of the Advances in Biochemical Engineering/Biotechnology book series (ABE, volume 96)

Abstract

Because of their characteristic living environments, marine organisms produce a variety of lipids. Fatty acids constitute the essential part of triglycerides and wax esters, which are the major components of fats and oils. Nevertheless, phospholipids and glycolipids have considerable importance and will be taken into account, especially the latter compounds that excite increasing interest regarding their promising biological activities. Thus, in addition to the major polyunsaturated fatty acids (PUFA) such as eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids, a great number of various fatty acids occur in marine organisms, e.g. saturated, mono- and diunsaturated, branched, halogenated, hydroxylated, methoxylated, non-methylene-interrupted. Various unprecedented chemical structures of fatty acids, and lipid-containing fatty acids, have recently been discovered, especially from the most primitive animals such as sponges and gorgonians. This review of marine lipidology deals with recent advances in the field of fatty acids since the end of the 1990s. Different approaches will be followed, mainly developing biomarkers of trophic chains in marine ecosystems and of chemotaxonomic interest, reporting new structures, especially those with biological activities or biosynthetic interest. An important part of this review will be devoted to the major PUFA, their relevance to health and nutrition, their biosynthesis, their sources (usual and promising) and market.

Lipids Fatty acids Marine organisms Biomarkers Nutrition 

Abbreviations

AA

arachidonic acid 20:4(n-6)

DHA

docosahexaenoic acid 22:6(n-3)

EPA

eicosapentaenoic acid 20:5(n-3)

FA

fatty acid

FATM

fatty-acid trophic markers

GC/MS

gas-chromatography mass spectrometry

PUFA

polyunsaturated fatty acids

LC-PUFA

long-chain polyunsaturated fatty acids

VLC-PUFA

Very-long-chain polyunsaturated fatty acids

MUFA

monounsaturated fatty acids

NMI

non-methylene-interrupted fatty acids

NMID

non-methylene-interrupted dienoic fatty acids

PL

phospholipids

SFA

saturated fatty acids

TL

total lipids

EFA

essential fatty acid

TAG

triacylglycerols

SCO

single-cell oil

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References

  1. 1.
    Sargent JR (1995) Origins and functions of egg lipids: nutritional implications. In: Bromage NR, Roberts RJ (eds.), Broodstock Management and Egg and Larval Quality. Blackwell Science, Oxford, p 353 Google Scholar
  2. 2.
    Sargent JR, Bell MV, Bell JG, Henderson RJ, Tocher DR (1995) Origins and functions of n-3 polyunsaturated fatty acids in marine organisms. In: Cevc G, Paltauf F (eds.), Phospholipids: Characterization, Metabolism and Novel Biological Applications. AOCS, Champaign, Illinois, p 248 Google Scholar
  3. 3.
    Pazos AJ, Roman G, Acosta CP, Sanchez JL, Abad M (1997) Comp Biochem Physiol 117B:393 Google Scholar
  4. 4.
    Ackman RG (ed) (1989) Marine Biogenic Lipids Fats and Oils. Vol I II. CRC, Boca Raton, Florida Google Scholar
  5. 5.
    Rezanka T (1989) Progr Lipid Res 28:147 CrossRefGoogle Scholar
  6. 6.
    Christie WW (ed) (2003) Lipid Analysis, Isolation, Separation, Identification and Structural Analysis of Lipids. The Oily Press, PJ Barnes, Brigwater, UK Google Scholar
  7. 7.
    Hagen W, Auel H (2001) Zoology 104:313 CrossRefGoogle Scholar
  8. 8.
    Dalsgaard J, St John M, Kattner G, Müller-Navarra D, Hagen W (2003) Adv Mar Biol 46:227 Google Scholar
  9. 9.
    Fattorusso E, Mangoni A (1997) Marine Glycolipids. In: Hertz W, Kirby GW, Moore RE, Steiglich W, Tamm W (eds), Progress in the Chemistry of Organic Natural Products. Springer, Wien, p 215 Google Scholar
  10. 10.
    Costantino V, Fattorusso E, Mangoni A, Di Rosa M, Ianaro A (1997) J Am Chem Soc 119:12 465 CrossRefGoogle Scholar
  11. 11.
    Costantino V, Fattorusso E, Imperatore C, Mangoni A (2003) Eur J Org Chem 1433 Google Scholar
  12. 12.
    Crul M, Mathot RAA, Giaccone G, Punt CJA, Rosing H, Hillebrand MJX, Ando Y, Nishi N, Tanaka H, Schellens J, Beijnen JH (2002) Cancer Chemotherap Pharmacol 49:287 CrossRefGoogle Scholar
  13. 13.
    Ackman RG (2002) Anal Chim Acta 465:175 CrossRefGoogle Scholar
  14. 14.
    Napolitano GE, Pollero RJ, Gayoso AN, MacDonald BA, Thompson RJ (1997) Biochem Syst Ecol 25:739 Google Scholar
  15. 15.
    Zhukova NV, Titlyanov EA (2003) Phytochemistry 62:191 CrossRefGoogle Scholar
  16. 16.
    Hooper JNA, Van Soest RWM (2002) Systema Porifera: A Guide to the Classification of Sponges. Kluwer Academic=Plenum, New York Google Scholar
  17. 17.
    Gurr MI, Hardwood JL (1991) Lipid Biochemistry: An Introduction. Chapman Hall, London, UK Google Scholar
  18. 18.
    Cook HW (1996) Fatty acid desaturation and chain elongation in eukaryotes. In: Vance DE, Vance JE (eds) Biochemistry of Lipids, Lipoproteins and Membranes. Elsevier Scientific, Amsterdam, p 129 Google Scholar
  19. 19.
    Sargent JR, Henderson RJ (1986) Lipids. In: Corner EDS, O'Hara SCM (eds) The biological chemistry of marine copepods, Vol 1. Clarendon, Oxford, UK, p 59 Google Scholar
  20. 20.
    Kattner G, Hagen W (1995) ICES J Mar Sci 52:329 CrossRefGoogle Scholar
  21. 21.
    Sprecher H (1992) Omega-3 News 7:1 Google Scholar
  22. 22.
    Sprecher H (2000) Biochim Biophys Acta 1486:219 PubMedGoogle Scholar
  23. 23.
    Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA (2001) J Lipid Res 42:501 PubMedGoogle Scholar
  24. 24.
    Henderson RJ (1999) The production of n-3 polyunsaturated faty acids in marine organisms. In: Lipid Technology. Barnes PJ, UK, p 5 Google Scholar
  25. 25.
    Nichols DS (2003) FEMS Microbiol Lett 219:1 CrossRefPubMedGoogle Scholar
  26. 26.
    Nadjek M, Debobbis D, Miokovic D, Ivancic I (2002) J Plankton Res 24:494 Google Scholar
  27. 27.
    Harvey HR, Macko SA (1997) Organic Geochem 26:531 CrossRefGoogle Scholar
  28. 28.
    Budge SM, Parrish CC (1998) Organic Geochem 29:1547 CrossRefGoogle Scholar
  29. 29.
    Budge SM, Parrish CC, McKenzie CH (2001) Mar Chem 73:285 CrossRefGoogle Scholar
  30. 30.
    Russel NJ, Nichols DS (1999) Microbiology 145:767 PubMedGoogle Scholar
  31. 31.
    Nichols DS, McMeekin TA (2002) J Microbiol Meth 48:161 CrossRefGoogle Scholar
  32. 32.
    Pond DW, Allen CE, Bell MV, Van Dover CL, Fallik AE, Dixon DR, Sargent JR (2002) Mar Ecol Progr Ser 225:219 Google Scholar
  33. 33.
    Yu R, Yamada A, Watanabe K, Yazawa K, Takeyama H, Matsunaga T, Kuranr R (2000) Lipids 35:1061 PubMedGoogle Scholar
  34. 34.
    Hannun YA, Obeid LM, Dbaibo GS (1996) Handbook of Lipid Research, Vol 8, p 177 Google Scholar
  35. 35.
    Wha Sona B, Chul Kima J, Dae Choib H (2001) Lipids 36:427 PubMedGoogle Scholar
  36. 36.
    Dembitsky VM, Srebnik M (2002) Progr Lipid Res 41:315 CrossRefGoogle Scholar
  37. 37.
    Wu M, Milligan KE, Gerwick WH (1997) Tetrahedron 53:15 983 Google Scholar
  38. 38.
    Kan Y, Sakamoto B, Fujita T, Nagai H (1998) J Nat Prod 61:152 CrossRefPubMedGoogle Scholar
  39. 39.
    Mesguiche V,Valls R, Piovetti L, Peiffer G (1999) Tetrahedron Lett 40:7473 CrossRefGoogle Scholar
  40. 40.
    Kan Y, Sakamoto B, Fujita T, Nagai H (2000) J Nat Prod 63:1599 CrossRefPubMedGoogle Scholar
  41. 41.
    Falk-Petersen S, Sargent JR, Henderson J, Hegseth EN, Hop H, Okolodkov YB (1998) Polar Biol 20:41 CrossRefGoogle Scholar
  42. 42.
    Henderson RJ, Hegesth EN, Park MT (1998) Polar Biol 20:48 CrossRefGoogle Scholar
  43. 43.
    Volkman JK, Barett SM, Blackburn SI, Mansour MP, Sikes EL, Gelin F (1998) Organic Geochem 29:1163 CrossRefGoogle Scholar
  44. 44.
    Reuss N, Poulsen LK (2002) Mar Biol 141:423 CrossRefGoogle Scholar
  45. 45.
    Viso AC, Marty JC (1993) Phytochemistry 34:1521 CrossRefGoogle Scholar
  46. 46.
    Viron C, Saunois A, André P, Perly B, Lafosse M (2000) Anal Chim Acta 409:257 CrossRefGoogle Scholar
  47. 47.
    Mostaert AS, Karsten U, Hara Y, Watanabe MM (1998) Phycol Res 46:213 CrossRefGoogle Scholar
  48. 48.
    Cho ES, Rhodes LL, Kim HK (1999) J Fish Sci Tech 2:58–65 Google Scholar
  49. 49.
    Marshall JA, Nichols PD, Hallegraeff GM (2002) J Applied Phycol 14:255 CrossRefGoogle Scholar
  50. 50.
    Khozin-Goldberg I, Zheng Yu H, Adlerstein D, Didi-Cohen S, Heimer YM, Cohen Z (2000) Lipids 35:881 PubMedGoogle Scholar
  51. 51.
    Budge SM, Parrish CC (1999) Phytochemistry 52:561 CrossRefGoogle Scholar
  52. 52.
    Bergé JP, Gouygou JP, Dubacq JP, Durand P (1995) Phytochemistry 39:1017 CrossRefGoogle Scholar
  53. 53.
    Xu XQ, Beardall J, Hallam ND (1998) Phytochemistry 49:1249 CrossRefGoogle Scholar
  54. 54.
    Bell MV, Dick JR, Pond DW (1997) Phytochemistry 45:303 CrossRefGoogle Scholar
  55. 55.
    Arzul G, Gentien P, Bodennec G, Toularastel F, Youenou A, Crassous MP (1998) Potential toxicity of microalgal polyunsaturated fatty acids. In: Baudimant G, Guezennec JH, Roy P, Samain JF (eds) Marine Lipids. IFREMER, Plouzané, France, p 53 Google Scholar
  56. 56.
    Bodennec G, Gentien P, Parrish CC, Crassous MP (1998) Lipid class and fatty acid compositions of toxic Gymnodinium and Heterosigma strains: haemolytic and signature compounds. In: Baudimant G, Guezennec JH, Roy P, Samain JF (eds) Marine Lipids. IFREMER, Plouzané, France, p 66 Google Scholar
  57. 57.
    Mansour MP, Volkman JK, Holdsworth DG, Jackson AE, Blackburn SI (1999) Phytochemistry 50:541 CrossRefGoogle Scholar
  58. 58.
    Mansour MP, Volkman JK, Jackson AE, Blackburn SI (1999) J Phycol 35:710 CrossRefGoogle Scholar
  59. 59.
    Rezanka T (1990) J Chromatogr 513:344 CrossRefGoogle Scholar
  60. 60.
    Van Pelt CK, Huang MC, Tschanz CL, Brenna JT (1999) J Lipid Res 40:1501 PubMedGoogle Scholar
  61. 61.
    Tanaka I, Matsuoka S, Murata M, Tachibana K (1998) J Nat Prod 61:685 CrossRefPubMedGoogle Scholar
  62. 62.
    Li X, Fan L, Lou Q (2002) Phytochemistry 59:157 CrossRefGoogle Scholar
  63. 63.
    Fleurence J, Gutbier G, Mabeau S, Leray C (1994) J Applied Phycol 6:527 CrossRefGoogle Scholar
  64. 64.
    Khotimchenko SV, Vaskovsky VE, Titlyanova TV (2002) Botanica Marina 45:17 CrossRefGoogle Scholar
  65. 65.
    Graeve M, Kattner G, Wiencke C, Karsten U (2002) Mar Ecol Progr Ser 231:67 Google Scholar
  66. 66.
    Sajiki J, Kakimi H (1998) J Chromatogr 795A:227 CrossRefGoogle Scholar
  67. 67.
    Kornprobst JM, Barnathan G (1998) Recent Res Dev Lipid Res 2:371 Google Scholar
  68. 68.
    Carballeira NM (2002) Progr Lipd Res 41:433 Google Scholar
  69. 69.
    Barnathan G, Bourgougnon N, Kornprobst JM (1998) Phytochemistry 47:761 CrossRefGoogle Scholar
  70. 70.
    Smith SL, Schnack-Schiel SB (1990) Polar zooplankton. In: Smith WO (ed) Polar Oceanography, Part B: Chemistry, Biology and Geology. Academic, San Diego, California, p 527 Google Scholar
  71. 71.
    Albers CS, Kattner G, Hagen W (1996) Mar Chem 55:347 CrossRefGoogle Scholar
  72. 72.
    Atkinson A, Snyder R (1997) Mar Ecol Progr 160:63 Google Scholar
  73. 73.
    Mayzaud P, Albessard E, Cuzin-Roudy J (1998) Mar Ecol Progr Ser 173:19 Google Scholar
  74. 74.
    Pond DW, Sargent JR (1998) J Plankton Res 20:169 Google Scholar
  75. 75.
    Kattner G, Hagen W, Graeve M, Albers C (1998) Mar Chem 61:219 CrossRefGoogle Scholar
  76. 76.
    Kattner G, Hagen W (1998) Mar Ecol Progr Ser 170:203 Google Scholar
  77. 77.
    Falk-Petersen S, Sargent JR, Lonne OJ, Timofeev SF (1999) Polar Biol 21:37 CrossRefGoogle Scholar
  78. 78.
    Falk-Petersen S, Hagen W, Kattner G, Clarke A, Sargent J (2000) Can J Fish Aquat Sci 57:178 CrossRefGoogle Scholar
  79. 79.
    Falk-Petersen S, Dahl TM, Scott CL, Sargent JR, Gulliksen B, Kwasniewski S, Hop H, Millar RM (2002) Mar Ecol Progr Ser 187:187 Google Scholar
  80. 80.
    Scott CL, Falk-Petersen S, Dahl TM, Sargent JR, Hop H, Lonne AJ, Poltermann M (1999) Polar Biol 21:65 CrossRefGoogle Scholar
  81. 81.
    Scott CL, Kwasniewski S, Falk-Petersen S, Millar RM, Sargent JR, (2000) Polar Biol 23:510 CrossRefGoogle Scholar
  82. 82.
    Jones PJH, MacDougall DE, Ntanios P,Vanstone CA, Mayzaud P, Albessard E, Cuzin-Roudy J (1998) Mar Biol Progr Ser 173:149 Google Scholar
  83. 83.
    Cripps GC, Watkins JL, Hill HJ, Atkinson A (1999) Mar Ecol Progr Ser 181:177 Google Scholar
  84. 84.
    Cho KW, Shin J, Jung K (1999) Ocean Res 21:109 Google Scholar
  85. 85.
    Nelson MM, Phleger CF, Mooney BD, Nichols PD (2000) Lipids 35:551 PubMedGoogle Scholar
  86. 86.
    Nelson MM, Mooney B, Nichols PD, Phleger CF (2001) Mar Chem 73:53 CrossRefGoogle Scholar
  87. 87.
    Phleger CF, Nelson MM, Mooney B, Nichols PD (2000) Polar Biol 23:329 CrossRefGoogle Scholar
  88. 88.
    Phleger CF, Nichols PD, Virtue P (1998) Comp Biochem Physiol 120B:311 Google Scholar
  89. 89.
    Phleger CF, Nelson MM, Mooney B, Nichols PD (1999) Comp Biochem Physiol 124B:295 Google Scholar
  90. 90.
    Swadling KM, Nichols PD, Gibson JAE, Ritz DA (2000) Mar Ecol Prog Ser 208:171 Google Scholar
  91. 91.
    Litchfield C, Morales RW (1976) Are Demospongiae membranes unique in living organisms? In: Harrison FW, Cowden RR (eds.), Aspects of Sponge Biology. Academic, New York, p 183 Google Scholar
  92. 92.
    Bergquist P (ed) (1978) Sponges. Hutchinson University Library, London Google Scholar
  93. 93.
    Djerassi C, Lam WK (1991) Acc Chem Res 24:69 CrossRefGoogle Scholar
  94. 94.
    Christie WW, Brechany EY, Marekov IN, Stefanov KL, Andreev SN (1994) Comp Biochem Physiol 109B:245 Google Scholar
  95. 95.
    Carballeira NM, Emiliano A, Hernandez-Alonso N, Gonzalez FA (1998) J Nat Prod 61:1543 CrossRefPubMedGoogle Scholar
  96. 96.
    Barnathan G, Kornprobst JM (1998) Fatty acids from marine organisms: recent research developments. In: Baudimant G, Guezennec J, Roy P, Samain JF (eds) Marine Lipids. IFREMER, Brest, France, p 35 Google Scholar
  97. 97.
    Barnathan G, Kornprobst JM (1998) Recent Res Devel Lipids Res 2:235 Google Scholar
  98. 98.
    Carballeira NM, Shalabi F (1993) J Nat Prod 56:739 CrossRefPubMedGoogle Scholar
  99. 99.
    Barnathan G, Kornprobst JM, Doumenq P, Mirallès J (1995) Lipids 31:193 Google Scholar
  100. 100.
    Carballeira NM (1997) Recent Res Develop Lipid Res 1:9 Google Scholar
  101. 101.
    Carballeira NM, Alicea J (2001) Lipids 36:83 PubMedGoogle Scholar
  102. 102.
    Barnathan G, Genin E, Velosaotsy NE, Kornprobst JM, Al-Lihaibi S, Al-Sofyani, Nongonierma R (2003) Comp Biochem Physiol 135B:297 Google Scholar
  103. 103.
    Makarieva TN, Santalova EA, Gorshkova IA, Dmitrenok AS, Guzii AG, Gorbach VI, Svetashev VI, Stonik VA (2002) Lipids 37:75 PubMedGoogle Scholar
  104. 104.
    Rodkina SA, Latyshev NA, Imbs AB (2003) Russ J Bioorg Chem 29:382 CrossRefGoogle Scholar
  105. 105.
    Meyer M, Guyot M (2002) Lipids 37:1109 PubMedGoogle Scholar
  106. 106.
    Nemoto T, Yoshino G, Ojika M, Sakagami Y (1997) Tetrahedron 53:166 699 CrossRefGoogle Scholar
  107. 107.
    Li Y, Ishibashi M, Sasaki T, Kabayashi J (1995) J Chem Res (S):126 Google Scholar
  108. 108.
    Li Y, Ishibashi M, Sasaki T, Kabayashi J (1995) J Chem Res (M):901 Google Scholar
  109. 109.
    Carballeira NM, Medina JR (1994) J Nat Prod 57:1688 CrossRefPubMedGoogle Scholar
  110. 110.
    Carballeira NM, Reyes M (1995) J Nat Prod 58:1689 CrossRefPubMedGoogle Scholar
  111. 111.
    Carballeira NM, Reyes ED, Sostre A, Rodriguez AD, Rodriguez JL, Gonzales FA (1997) J Nat Prod 60:502 CrossRefPubMedGoogle Scholar
  112. 112.
    Kawakami A, Miyamoto T, Higuchi R, Uchiumi T, Kuwano M, Van Soest RWM (2001) Tetrahedron Lett 42:3335 CrossRefGoogle Scholar
  113. 113.
    Carballeira NM, Pagan M (2000) J Nat Prod 63:666 CrossRefPubMedGoogle Scholar
  114. 114.
    Nechev J, Christie WW, Robaina R, de Diego F, Popov S, Stefanov K (2002) Eur J Lipid Sci Technol 104:800 CrossRefGoogle Scholar
  115. 115.
    Nechev J, Christie WW, Robaina R, de Diego FM, Ivanova A, Popov S, Stefanov K (2002) Hydrobiologia 489:91 CrossRefGoogle Scholar
  116. 116.
    Nechev J, Christie WW, Robaina R, de Diego F, Popov S, Stefanov K (2004) Comp Biochem Physiol 137A:365 Google Scholar
  117. 117.
    Carballeira NM, Pagan M (2001) J Nat Prod 64:620 CrossRefPubMedGoogle Scholar
  118. 118.
    Thiel V, Jenisch A, Worheide G, Lowenberg A, Reitner J, Michaelis W (1999) Org Geochem 30:1 CrossRefGoogle Scholar
  119. 119.
    Kornprobst JM, Barnathan G (2000) Recent Res Progr Lipid Res 2:371 Google Scholar
  120. 120.
    Ayanoglu E, Kornprobst JM, Aboud-Bichara A, Djerassi C (1983) Tetrahedron Lett 24:1111 CrossRefGoogle Scholar
  121. 121.
    Ayanoglu E, Popov S, Kornprobst JM, Aboud-Bichara A, Djerassi C (1983) Lipids 18:830 Google Scholar
  122. 122.
    Carballeira NM, Alicea J (2002) Lipids 37:305 PubMedGoogle Scholar
  123. 123.
    Carballeira NM, Colon R (1999) Tetrahedron Asymmetry 10:3785 CrossRefGoogle Scholar
  124. 124.
    Soderquist JA, Rosado I, Marrero Y (1998) Tetrahedron Lett 39:3115 CrossRefGoogle Scholar
  125. 125.
    Quinn RJ, Tucker DJ (1985) Tetrahedron Lett 26:1671 CrossRefGoogle Scholar
  126. 126.
    Hirsch SC, Carmely S, Kashman Y (1987) Tetrahedron 43:3257 CrossRefGoogle Scholar
  127. 127.
    Van Soest RWM, Fusetani N, Andersen RJ (1997) Straight-chain acetylenes as chemotaxonomic markers of the marine Haplosclerida. In: Watanabe Y, Fusetani N (eds) Sponge Sciences–Multidisciplinary Perspectives. Springer-Verlag, Berlin Heidelberg New York, p 3 Google Scholar
  128. 128.
    Pham NB, Butler MS, Hooper JNA, Moni RW, Quinn RJ (1999) J Nat Prod 62:1439 CrossRefPubMedGoogle Scholar
  129. 129.
    Matsunaga S, Okada Y, Fusetani N, Van Soest RWM (2000) J Nat Prod 63:690 CrossRefPubMedGoogle Scholar
  130. 130.
    Lee HS, Rho JR, Sim CJ, Shin J (2003) J Nat Prod 66:566 CrossRefPubMedGoogle Scholar
  131. 131.
    Fujita M, Nakao Y, Matsunaga S, Van Soest RWM, Itoh Y, Seiki M, Fusetani N (2003) J Nat Prod 66:569 CrossRefPubMedGoogle Scholar
  132. 132.
    Zhao QC, Lee SY, Hong JK, Lee CO, Im KS, Lee DS, Sim CJ, Jung JH (2003) J Nat Prod 66:408 CrossRefPubMedGoogle Scholar
  133. 133.
    Hattori T, Adachi K, Shizuri Y (1998) J Nat Prod 61:823 CrossRefPubMedGoogle Scholar
  134. 134.
    Venkateswarlu Y, Srinivasa Reddy N, Ramesh P, Rama Rao M, Siva Ram T (1998) Indian J Chem 37B:1264 Google Scholar
  135. 135.
    Lo JM, Wang WL, Chiang YM, Chen CM (2001) J Chin Chem Soc 48:821 Google Scholar
  136. 136.
    Natori T, Morita M, Akimoto K, Koezuka Y (1994) Tetrahedron 50:2771 CrossRefGoogle Scholar
  137. 137.
    Li HY, Matsunaga S, Fusetani N (1995) Tetrahedron 51:2273 CrossRefGoogle Scholar
  138. 138.
    Koezuka Y, Motoki K, Sakai T, Natori T (1999) Recent Res Dev Cancer 1:341 Google Scholar
  139. 139.
    Costantino V, Fattorusso E, Mangoni A, Di Rosa M, Ianaro M (1997) J Am Chem Soc 119:12 465 CrossRefGoogle Scholar
  140. 140.
    Costantino V, Fattorusso E, Mangoni A (2000) Tetrahedron 56:5953 CrossRefGoogle Scholar
  141. 141.
    Costantino V, Fattorusso E, Mangoni A (2001) Glycolipids with immunomodulating activity from marine sponges. In: Tringali C (ed), Bioactive Compounds from Natural Sources. Taylor Francis, London, New York, Chap 14 p. 557 Google Scholar
  142. 142.
    Meguro S, Namikoshi M, Kobayashi H (2002) J Antibiotics 55:256 Google Scholar
  143. 143.
    Hayakawa Y, Rovero S, Forni G, Smyth MJ (2003) Proc Nat Acad Sci 100:9464 CrossRefPubMedGoogle Scholar
  144. 144.
    Kobayashi E, Motoki K, Uchida T, Fukushima H, Koezuka Y (1998) Oncol Res 7:529 Google Scholar
  145. 145.
    Morita M, Motoki K, Natori T, Sakai T, Sawa E, Yamaji K, Koezuka K, Kobayashi E, Fukushima H (1995) J Med Chem 38:2176 CrossRefPubMedGoogle Scholar
  146. 146.
    Costantino V, Fattorusso E, Imperatore C, Mangoni A (2002) J Nat Prod 65:883 CrossRefPubMedGoogle Scholar
  147. 147.
    Vysotskii MV, Svetashev VI (1991) Biochim Biophys Acta 1083:161 PubMedGoogle Scholar
  148. 148.
    Vysotskii MV, Svetashev VI (1998) Comp Biochem Physiol 119B:73 Google Scholar
  149. 149.
    Mirallès J, Barnathan G, Galonnier R, Sall T, Samb A, Gaydou EM, Kornprobst JM (1995) Lipids 30:459 PubMedGoogle Scholar
  150. 150.
    Carballeira NM, Sostre A, Rodriguez AD (1996) Comp Biochem Physiol 113B:781 Google Scholar
  151. 151.
    Carballeira NM, Sostre A, Rodriguez AD (1997) Comp Biochem Physiol 118B:257 Google Scholar
  152. 152.
    Carballeira NM, Emiliano A, Rodriguez J, Reyes E (1992) Lipids 27:681 PubMedGoogle Scholar
  153. 153.
    Barnathan G, Doumenq P, Mirallès J, Boury-Esnault N, Kornprobst JM (1993) J Nat Prod 56:2104 CrossRefGoogle Scholar
  154. 154.
    Carballeira NM, Miranda C, Rodriguez AD (2002) Comp Biochem Physiol 131B:83 Google Scholar
  155. 155.
    Urvois PA, Barnathan G, Biard JF, Débitus C, Verbist JF (1998) Fatty acid composition of the New Caledonian gorgonian Rumphella aggregata: identification of 9-methyl-6,9-heptadecadienoic acid. In: Baudimant G, Guezennec J, Roy P, Samain JF (eds) Marine Lipids. IFREMER, Brest, p 44 Google Scholar
  156. 156.
    Mancini I, Guerriero A, Bakken T, Zibrowius G, Pietra F (1999) Helv Chim Acta 82:677 CrossRefGoogle Scholar
  157. 157.
    Henderson RJ, Burkow IC, Buzzi M, Bayer A (1998) Biochim Biophys Acta 1392:309 PubMedGoogle Scholar
  158. 158.
    Henderson RJ (2000) J Mar Biol Ass UK 80:311 CrossRefGoogle Scholar
  159. 159.
    Yamashiro H, Oku H, Higa H, Chinen I, Sakai K (1999) Comp Biochem Physiol 122B:397 Google Scholar
  160. 160.
    Jeong TS, Ahn JA, Kim YK, Bok SH, Kwon BM (1999) Bioorganic Medicinal Chem Lett 7:1481 CrossRefGoogle Scholar
  161. 161.
    Ota T, Chihara Y, Itabashi Y, Tagaki T (1994) Fisheries Sci 60:171 Google Scholar
  162. 162.
    McKenzie JD, Black KD, Kelly MS, Newton LC, Handley LL, Scrimpgeour CM, Raven JA, Henderson RJ (2000) J Mar Biol Ass UK 80:311 CrossRefGoogle Scholar
  163. 163.
    Kawasaki KI, Nabeshima YI, Ishihara K, Kaneniwa M, Ooizumi T (2000) Fisheries Sci 66:614 CrossRefGoogle Scholar
  164. 164.
    Ishihara K, Murata M, Kaneniwa M (1998) Lipids 33:1107 PubMedGoogle Scholar
  165. 165.
    Sato D, Ando Y, Tsujimoto R, Kawasaki K (2001) Lipids 36:1371 PubMedGoogle Scholar
  166. 166.
    Inagaki M, Isobe R, Kawano Y, Miyamoto T, Komori T, Higuchi R (1998) Eur J Org Chem 129 Google Scholar
  167. 167.
    Yamada K, Matsubara R, Kaneko M, Miyamoto T, Higuchi R (2001) Chem Pham Bull 49:447 CrossRefGoogle Scholar
  168. 168.
    Yamada K, Sasaki K, Harada Y, Isobe R, Higuchi R (2002) Chem Pham Bull 50:1467 CrossRefGoogle Scholar
  169. 169.
    Yamada K, Hamada A, Kisa F, Miyamoto T, Higuchi R (2003) Chem Pham Bull 51:46 CrossRefGoogle Scholar
  170. 170.
    Jeong BY, Ohshima T, Koizumi C (1996) Lipids 31:9 PubMedGoogle Scholar
  171. 171.
    Pond DW, Sargent JR (1998) J Plankton Res 20:169 Google Scholar
  172. 172.
    Viracaoundin I, Barnathan G, Gaydou EM, Aknin M (2003) Lipids 38:85 PubMedGoogle Scholar
  173. 173.
    Kraffe E, Soudant P, Marty Y, Kervarec N, Jehan P (2002) Lipids 37:507 PubMedGoogle Scholar
  174. 174.
    Freites L, Fernandez-Reiriz MJ, Labarta U (2002) Aquaculture 207:97 CrossRefGoogle Scholar
  175. 175.
    Galap C, Netchitailo P, Leboulenger F, Grillot JP (1999) Comp Biochem Physiol 122A:241 Google Scholar
  176. 176.
    Kraffe E, Soudant P, Marty Y, Kervaec N, Jehan P (2002) Lipids 37:507 PubMedGoogle Scholar
  177. 177.
    Freites L, Fernandez-Reiriz MJ, Labarta U (2002) Comp Biochem Physiol 132B:453 Google Scholar
  178. 178.
    Caers M, Coutteau P, Cure K, Morales V, Gajardo G, Sorgeloos P (1999) Comp Biochem Physiol 123B:97 Google Scholar
  179. 179.
    Soudant P, Ryckeghem KV, Marty Y, Moal J, Samain JF, Sorgeloos P (1999) Comp Biochem Physiol 123B:209 Google Scholar
  180. 180.
    Garrido JL, Medina I (2002) Analytica Chim Acta 465:409 CrossRefGoogle Scholar
  181. 181.
    Murphy KJ, Mooney BD, Mann NJ, Nichols PD, Sinclair AJ (2002) Lipids 37:587 PubMedGoogle Scholar
  182. 182.
    Abad M, Ruiz, C, Martinez D, Mosquera G, Sanchez JL (1995) Comp Biochem Physiol 110C:109 Google Scholar
  183. 183.
    Labarta U, Fernandez-Reiriz MJ, Perez-Camacho A (1999) Comp Biochem Physiol 123A:249 Google Scholar
  184. 184.
    Soudant P, Moal J, Marty Y, Samain JF (1997) J Exp Mar Biol Ecol 215:103 CrossRefGoogle Scholar
  185. 185.
    Brazao S, Morais S, Boaventura D, Re P, Narciso L, Hawkins SJ (2003) Comp Biochem Physiol 136B:425 Google Scholar
  186. 186.
    Fernandez-Reiriz MJ, Labarta U, Albentosa M, Perez-Camacho A (1999) Comp Biochem Physiol 124B:309 Google Scholar
  187. 187.
    Le Pennec M, Beninger PG, Dorange G, Paulet YM (1991) J Mar Biol Assoc UK 71:451 Google Scholar
  188. 188.
    Pazos AJ, Roman G, Acosta CP, Sanchez JL, Abad M (1997) Comp Biochem Physiol 117B:393 Google Scholar
  189. 189.
    Le Pennec G, Le Pennec M, Beninger PG (2001) J Mar Biol Assoc UK 81:663 Google Scholar
  190. 190.
    Caers M, Coutteau P, Cure K, Morales V, Gajardo G, Sorgeloos P (1999) Comp Biochem Physiol 123B:89 Google Scholar
  191. 191.
    Caers M, Coutteau P, Sorgeloos P (1999) Aquaculture 170:307 CrossRefGoogle Scholar
  192. 192.
    Marty Y, Soudant P, Perrotte S, Moal J, Dussauze J, Samain JF (1999) J Chromatogr A 839:119 CrossRefGoogle Scholar
  193. 193.
    Jeong BY, Ohshima T, Koizumi C (1999) Comp Biochem Physiol 122B:415 Google Scholar
  194. 194.
    de Moreno JEA, Moreno VJ, Ricci L, Roldan M, Gerpe M (1998) Comp Biochem Physiol 119B:631 Google Scholar
  195. 195.
    Hayashi K, Kishimura H (2002) J Oleo Sci 51:523 Google Scholar
  196. 196.
    Suprayudi MA, Takeuchi T, Hamasaki K (2004) Aquaculture 231:403 CrossRefGoogle Scholar
  197. 197.
    Takeuchi T, Satoh N, Sekiya S, Shimizu T, Watanabe T (1999) Nippon Suisan Gakkaishi 65:988 Google Scholar
  198. 198.
    Kobayashi T, Takeuchi T, Arai D, Sekiya S (2000) Nippon Suisan Gakkaishi 66:1006 Google Scholar
  199. 199.
    Hamasaki K, Suprayudi MA, Takeuchi T (2002) Suisan Zoshoku 50:333 Google Scholar
  200. 200.
    Suprayudi MA, Takeuchi T, Hamasaki K, Hirokawa J (2002) Suisan Zoshoku 50:205 Google Scholar
  201. 201.
    Suprayudi MA, Takeuchi T, Hamasaki, K, Hirokawa, J (2002) Fish Sci 68:1295 CrossRefGoogle Scholar
  202. 202.
    Lahdes E, Balogh G, Fodor E, Farkas T (2000) Lipids 35:1093 PubMedGoogle Scholar
  203. 203.
    Fodor E, Jones RH, Buda C, Kitajka K, Dey I (1995) Lipids 30:1119 PubMedGoogle Scholar
  204. 204.
    Cunnane SC (2003) Prog Lipid Res 42:544 CrossRefPubMedGoogle Scholar
  205. 205.
    Wada H, Gombos Z, Murata N (1990) Nature 347:200 CrossRefPubMedGoogle Scholar
  206. 206.
    Miquel M, James D, Dooner H, Browse J (1993) Proc Natl Acad Sci USA 90:6208 PubMedGoogle Scholar
  207. 207.
    Meves H (1994) Prog Neurobiol 43:175 CrossRefPubMedGoogle Scholar
  208. 208.
    Xiao YF, Ke Q, Wang SY, Auktor K, Yang Y, Wang GK, Morgan JP, Leaf A (2001) Proc Natl Acad Sci USA 98:3606 CrossRefPubMedGoogle Scholar
  209. 209.
    Schmidt A, Wolde M, Thiele C, Fest W, Kratzin H, Podtelejnikov AV, Witke W, Huttner WB, Söling HD (1999) Nature 401:133 CrossRefPubMedGoogle Scholar
  210. 210.
    Wallis JG, Browse J (2002) Prog Lipid Res 41:254 CrossRefPubMedGoogle Scholar
  211. 211.
    Goldberg EM, Zidovetzki R (1997) Biophys J 73:2603 PubMedGoogle Scholar
  212. 212.
    Tsutsumi T, Yamauci E, Suzuki E, Watanbe S, Kobayashi T, Okuyama H (1995) Biol Pharm Bull 18:664 PubMedGoogle Scholar
  213. 213.
    Wallis JG, Watts JL, Browse J (2002) Trends Biochem Sci 27:467 CrossRefPubMedGoogle Scholar
  214. 214.
    Napier JA (2002) Trends Plant Sci 7:51 CrossRefPubMedGoogle Scholar
  215. 215.
    Connor WE (2000) Am J Clin Nutr 71:171S PubMedGoogle Scholar
  216. 216.
    Albert, CM, Hennekens CH, O'Donnell CJ, Ajani UA, Carey VJ, Willett WC, Ruskin JN, Manson JE (1998) JAMA 279:23 CrossRefPubMedGoogle Scholar
  217. 217.
    Kromhout D (1998) JAMA 279:65 CrossRefPubMedGoogle Scholar
  218. 218.
    Krauss RM, Eckel RH, Howard B, Appel LJ, Daniels SR, Deckelbaum RJ, Erdman JW, Kris-Etherton P, Goldberg IJ, Kotchen TA, Lichtenstein AH, Mitch WE, Mullis R, Robinson K, Wylie-Rosett J, St Jeor S, Suttie J, Tribble DL, Bazzarre TL (2000) Circulation 102:2284 PubMedGoogle Scholar
  219. 219.
    O'Keefe Jr, James H, Harris WS (2000) Am J Cardiol 85:1239 CrossRefPubMedGoogle Scholar
  220. 220.
    Oomen CM, Feskens EJ, Räsänen L, Fidanza F, Nissinen AM, Menotti A, Kok FJ, Kromhout D (2000) Am J Epidemiol 151:999 PubMedGoogle Scholar
  221. 221.
    Torres IC, Mira L, Ornelas CP, Melim A (2000) Br J Nutr 83:371 PubMedGoogle Scholar
  222. 222.
    Iso H, Rexrode KM, Stampfer MJ, Manson JE, Colditz GA, Speizer FE, Hennekens CH, Willett WC (2001) JAMA 285:304 CrossRefPubMedGoogle Scholar
  223. 223.
    Hu FB, Bronner L, Willett WC, Stampfer MJ, Rexrode KM, Albert CM, Hunter D, Manson JE (2002) JAMA 287:1815 CrossRefPubMedGoogle Scholar
  224. 224.
    He K, Rimm EB, Merchant A, Rosner BA, Stampfer MJ, Willett WC, Ascherio A (2002) JAMA 288:3130 CrossRefPubMedGoogle Scholar
  225. 225.
    Calder PC (2003) Ital Heart J 4:427 PubMedGoogle Scholar
  226. 226.
    Thies F, Garry JMC, Yaqoob P, Rerkasem K, Williams J, Shearman CP, Gallagher PJ, Calder PC, Grimble RF (2003) The Lancet 361:477 CrossRefGoogle Scholar
  227. 227.
    Madsen, T, Skou HA, Hansen VE, Fog L, Christensen JH, Toft E, Schmidt EB (2001) Am J Cardiol 88:1139 CrossRefPubMedGoogle Scholar
  228. 228.
    Albert CM, Campos H, Stampfer MJ, Ridker PM, Manson JE, Willett WC, Ma J (2002) N Engl J Med 346:1113 CrossRefPubMedGoogle Scholar
  229. 229.
    Rosenberg IH (2002) New Engl J Med 346:1102 CrossRefPubMedGoogle Scholar
  230. 230.
    Christensen JH, Skou HA, Fog L, Hansen V, Vesterlund T, Dyerberg J, Toft E, Schmidt EB (2001) Circulation 103:651 Google Scholar
  231. 231.
    Bigger JT, El-Sherif T (2001) Circulation 103:623 PubMedGoogle Scholar
  232. 232.
    De Caterina R, Madonna R, Zucchi R, La Rovere MT (2003) Am Heart J 146:420 CrossRefPubMedGoogle Scholar
  233. 233.
    Dallongeville J, Yarnell J, Ducimetière P, Arveiler D, Ferrières J, Montaye M, Luc G, Evans A, Bingham A, Hass B, Ruidavets JB (2003) Circulation 108:820 CrossRefPubMedGoogle Scholar
  234. 234.
    Marchioli R, Schweiger C, Tavazzi L, Valagussa F (2001) Lipids 36:S119 PubMedGoogle Scholar
  235. 235.
    Marchioli R, Barzi F, Bomba E, Chieffo C, Di Gregorio D, Di Mascio R, Franzosi MG, Geraci E, Levantesi G, Maggioni AP, Mantini L, Marfisi RM, Mastrogiuseppe G, Mininni N, Nicolosi GL, Santini M, Schweiger C, Tavazzi L, Tognoni G, Tucci C, Valagussa F, GISSI-Prevenzione Investigators (2002) Circulation 105:1897 CrossRefPubMedGoogle Scholar
  236. 236.
    Leaf A (2002) Circulation 105:1874 CrossRefPubMedGoogle Scholar
  237. 237.
    Lemaitre RN, King IB, (2003) n-3 polyunsaturated FA, fatal ischemic heart disease, and nonfatal myocardial infarction in older adults: the cardiovascular health study. Am J Clin Nutr 77:319 PubMedGoogle Scholar
  238. 238.
    Harris WS (2003) Am J Clin Nutr 77:279 PubMedGoogle Scholar
  239. 239.
    Cobiac L, Nestel PJ, Wing LM, Howe PR (1991) Clin Exp Pharmacol Physiol 18:265 PubMedGoogle Scholar
  240. 240.
    Radack K, Deck C, Huster G (1991) Arch Intern Med 151:1173 CrossRefPubMedGoogle Scholar
  241. 241.
    Appel LJ, Miller ER, Seidler AJ, Whelton PK (1993) Arch Intern Med 153:1429 CrossRefPubMedGoogle Scholar
  242. 242.
    Morris MC, Sacks F, Rosner B (1993) Circulation 88:523 PubMedGoogle Scholar
  243. 243.
    Toft I, Bonaa KH, Ingebretsen OC, Nordoy A, Jenssen T (1995) Ann Intern Med 123:911 PubMedGoogle Scholar
  244. 244.
    Connor WE (1995) Ann Intern Med 123:950 PubMedGoogle Scholar
  245. 245.
    Andreassen AK, Hartmann A, Offstad J, Geiran O, Kvernebo K, Simonsen S (1997) J Am Coll Cardiol 29:1324 CrossRefPubMedGoogle Scholar
  246. 246.
    Bao DQ, Mori TA, Burke V, Puddey IB, Beilin LJ (1998) Hypertension 32:710 PubMedGoogle Scholar
  247. 247.
    Mori TA, Bao DQ, Burke V, Puddey IB, Watts GF, Beilin LJ (1999) Am J Clin Nutr 70:817 PubMedGoogle Scholar
  248. 248.
    Stark KD, Park EJ, Maines VA, Holub BJ (2000) Am J Clin Nutr 72:389 PubMedGoogle Scholar
  249. 249.
    Laidlaw M, Holub BJ (2003) Am J Clin Nutr 77:37 PubMedGoogle Scholar
  250. 250.
    Goodfellow J, Bellamy MF, Ramsey MW, Jones CJ, Lewis MJ (2000) J Am Coll Cardiol 35:265 CrossRefPubMedGoogle Scholar
  251. 251.
    Flaten H, Hostmark AT, Kierulf P, Lystad E, Trygg K, Bjerkedal T, Osland A (1990) Am J Clin Nutr 52:300 PubMedGoogle Scholar
  252. 252.
    Norrish AE, Skeaff CM, Arribas GL, Sharpe SJ, Jackson RT (1999) Br J Cancer 81:1238 CrossRefPubMedGoogle Scholar
  253. 253.
    Terry P, Lichtenstein P, Feychting M, Ahlbom A, Wolk A (2001) The Lancet 357:1764 CrossRefGoogle Scholar
  254. 254.
    Takezaki T, Hirose K, Inoue M, Hamajima N, Yatabe Y, Mitsudomi T, Sugiura T, Kuroishi T, Tajima K (2001) Br J Cancer 84:1199 CrossRefPubMedGoogle Scholar
  255. 255.
    Barber MD, Ross JA, Voss AC, Tisdale MJ, Fearon KC (1999) Br J Cancer 81:80 CrossRefPubMedGoogle Scholar
  256. 256.
    Gogos CA, Ginopoulos P, Salsa B, Apostolidou E, Zoumbos NC, Kalfarentzos F (1998) Cancer 82:395 CrossRefPubMedGoogle Scholar
  257. 257.
    Kremer JM (2000) Am J Clin Nutr 71:349S PubMedGoogle Scholar
  258. 258.
    Volker D, Fitzgerald P, Major G, Garg M (2000) J Rheumatol 27:2343 PubMedGoogle Scholar
  259. 259.
    Cleland LG, James MJ (2000) J Rheumatol 27:2305 PubMedGoogle Scholar
  260. 260.
    Navarro E, Esteve M, Olivé A, Klaassen J, Cabré E, Tena X, Fernandez-Bañares F, Pastor C, Gassull MA (2000) J Rheumatol 27:298 PubMedGoogle Scholar
  261. 261.
    Darlington LG, Stone TW (2001) Brit J Nutr 85:251 PubMedGoogle Scholar
  262. 262.
    Mayser P, Mrowietz U, Arenberger P, Bartak P, Buchwald J, Christophers E, Jablonska S, Salmhofer W, Schill WB, Krämer HJ, Schlotzer E, Mayer K, Seeger W, Grimminger F (1998) J Am Acad Dermatol 38:539 PubMedGoogle Scholar
  263. 263.
    Danno K, Sugie N (1998) J Dermat 25:703 Google Scholar
  264. 264.
    Hodge L, Salome CM, Peat JK, Haby MM, Xuan W, Woolcock AJ (1996) Med J Aust 164:137 PubMedGoogle Scholar
  265. 265.
    Broughton KS, Johnson CS, Pace BK, Liebman M, Kleppinger KM (1997) Am J Clin Nut 65:1011 Google Scholar
  266. 266.
    Katz DP, Manner T, Furst P, Askanazi J (1996) Nutrition 12:334 CrossRefPubMedGoogle Scholar
  267. 267.
    Schwartz J (2000) Am J Clin Nutr 71:393S PubMedGoogle Scholar
  268. 268.
    Stevens LJ, Zentall SS, Deck JL, Abate ML, Watkins BA, Lipp SR, Burgess JR (1995) Am J Clin Nutr 62:761 PubMedGoogle Scholar
  269. 269.
    Burgess JR, Stevens L, Zhang W, Peck L (2000) Am J Clin Nutr 71:327S PubMedGoogle Scholar
  270. 270.
    Stordy BJ (2000) Am J Clin Nutr 71:323S PubMedGoogle Scholar
  271. 271.
    Heude, B, Ducimetière P, Berr C, Study E (2003) Am J Clin Nutr 77:803 PubMedGoogle Scholar
  272. 272.
    Edwards R, Peet M, Shay J, Horrobin D (1998) J Affect Disord 48:149 CrossRefPubMedGoogle Scholar
  273. 273.
    Calabrese, JR, Rapport DJ, Shelton MD (1999) Arch Gen Psychiatry 56:413 CrossRefPubMedGoogle Scholar
  274. 274.
    Kyle DJ, Schaefer E, Patton G, Beiser A (1999) Lipids 34:S245 PubMedGoogle Scholar
  275. 275.
    Severus, WE, Ahrens B, Stoll AL (1999) Arch Gen Psychiatry 56:380 CrossRefPubMedGoogle Scholar
  276. 276.
    Stoll AL, Severus WE, Freeman MP, Rueter S, Zboyan HA, Diamond E, Cress KK, Marangell LB (1999) Arch Gen Psychiatry 56:407 CrossRefPubMedGoogle Scholar
  277. 277.
    Bruinsma KA, Taren DL (2000) Nut Rev 58:98 Google Scholar
  278. 278.
    Conquer JA, Tierney MC, Zecevic J, Bettger WJ, Fisher RH (2000) Lipids 35:1305 PubMedGoogle Scholar
  279. 279.
    Joy CB, Mumby-Croft R, Joy LA (2000) Cochrane Database Syst Rev 4 Google Scholar
  280. 280.
    Richardson AJ, Easton T, Puri BK (2000) European Neuropsychopharmacology 10:189 CrossRefPubMedGoogle Scholar
  281. 281.
    Tanskanen A, Hibbeln JR, Hintikka J, Haatainen K, Honkalampi K, Viinamäki H (2001) Arch Gen Psychiatry 58:512 CrossRefPubMedGoogle Scholar
  282. 282.
    Peet M, Horrobin DF (2002) Arch Gen Psychiat 59:913 CrossRefPubMedGoogle Scholar
  283. 283.
    Small MF (2002) New Scientist, August 24:34 Google Scholar
  284. 284.
    Levine BS (1997) Nutrition Today 32:248 Google Scholar
  285. 285.
    Fidler N, Sauerwald T, Pohl A, Demmelmair H, Koletzko B (2000) J Lipid Res 41:1376–83 PubMedGoogle Scholar
  286. 286.
    Olsen S,Secher NJ (2002) Brit Med J 324:1 Google Scholar
  287. 287.
    Jensen CL, Maude M, Anderson RE, Heird WC (2000) Am J Clin Nutr 71:292S PubMedGoogle Scholar
  288. 288.
    Makrides M, Gibson RA (2000) Am J Clin Nutr 71:307S PubMedGoogle Scholar
  289. 289.
    Connor WE, Lowensohn R, Hatcher L (1996) Lipids 31:S183 PubMedGoogle Scholar
  290. 290.
    Cunnane SC, Francescutti V, Brenna JT, Crawford MA (2000) Lipids 35:105 PubMedGoogle Scholar
  291. 291.
    Carlson SE (1999) Acta Paediatr Suppl 88:72 CrossRefGoogle Scholar
  292. 292.
    Mitchell EA, Aman MG, Turbott SH, Manku M (1987) Clin Pediatr 26:406 Google Scholar
  293. 293.
    Uauy-Dagach R, Valenzuela A (1996) Nutr Rev 54:S102 PubMedGoogle Scholar
  294. 294.
    Pepping J (1999) Am J Health-Syst Ph 56:719 Google Scholar
  295. 295.
    Simopoulos AP (2002) Biomed Pharmacother 56:365 CrossRefPubMedGoogle Scholar
  296. 296.
    de Lorgeril M RS, Mamelle N, Salen P, Martin JL, Mon-jaud I, Guidollet J, Touboul P, Delaye J (1994) Lancet 343:1454 CrossRefPubMedGoogle Scholar
  297. 297.
    Bartram HP, Gostner A, Reddy BS, Rao CV, Scheppach W, Dusal G, Richter A, Richter F, Kasper H (1995) Eur J Cancer Prev 4:231 Google Scholar
  298. 298.
    Maillard V, Bougnoux P, Ferrari P, Jourdan M-L, Pinault M, Lavillonnieree FF, Body G, Le Floch O, Chajes V (2002) Int J Cancer 98:78 CrossRefPubMedGoogle Scholar
  299. 299.
    James MJ, Cleland LG (1997) Semin Arthritis Rheum 27:85 CrossRefPubMedGoogle Scholar
  300. 300.
    Heath and Welfare Canada (1990). Table 19. Summary of examples of recommended nutrients based on energy expressed as daily rates. In: Nutrition Recommendations. The reports of the scientific review committee. Health and Welfare Canada, Scientific review committee, Ottawa, 203 (H49-42=1990E) Google Scholar
  301. 301.
    ISSFAL (1999) Adequate intakes. International Society for the Study of FA and Lipids (ISSFAL), Devon ( http://www.issfal.org.uk/adequateintakes.htm )
  302. 302.
    BNF (2000) British Nutrition Foundation (BNF), London Google Scholar
  303. 303.
    IOM (2002) Dietary reference intakes for energy, carbohydrates, fiber, fat, protein and amino acids (macronutrients). National Academy of Sciences, food and nutrition board, Institute of Medicine (IOM). National Academy Press (NAP), Washington, DC, 335–432 Google Scholar
  304. 304.
    Watkins BA, Lippman HE, Le Bouteiller L, Seifert MF (2001) Prog Lipid Res 40:125 CrossRefPubMedGoogle Scholar
  305. 305.
    Ucciani E (1995) Nouveau Dictionnaire des Huiles Végétales. Compositions en acides gras. Lavoisier TEC&DOC, Paris (France) Google Scholar
  306. 306.
    Abbadi A, Domergue F, Meyer A, Riedel K, Sperling P, Zank TK, Heinz E (2001) Eur J Lipid Sci Technol 103:106 CrossRefGoogle Scholar
  307. 307.
    Naylor RL, Goldburg RJ, Primavera JH, Kautsky N, Beveridge MC, Clay J, Folke C, Lubchenco J, Mooney H, Troell M (2000) Nature 405:1017 CrossRefPubMedGoogle Scholar
  308. 308.
    Tocher DR, Leaver MJ, Hodgson PA (1998) Prog Lipid Res 37:73 CrossRefPubMedGoogle Scholar
  309. 309.
    Shanklin J, Cahoon EB (1998) Annu Rev Plant Physiol Plant Mol Biol 49:611 CrossRefPubMedGoogle Scholar
  310. 310.
    Pereira SL, Leonard AE, Mukerji P (2003) Protaglandins, Leukotrienes and essential FA 68:97 CrossRefGoogle Scholar
  311. 311.
    Napier JA, Sayanova O, Sperling P, Heinz E (1999) Trends Plant Sci 4:2 CrossRefGoogle Scholar
  312. 312.
    Napier JA, Michaelson LV, Sayanova O (2003) Prostaglandins Leukot Essent Fatty Acids 68:135 CrossRefGoogle Scholar
  313. 313.
    Satouchi K, Hirano K, Sakaguchi M, Takehara H, Matsuura F (1993) Lipids 28:837 PubMedGoogle Scholar
  314. 314.
    Beaudoin F, Michaelson LV, Hey SJ, Lewis, MJ, Shewry PR, Sayanova O, Napier J (2000) Proc Natl Acad Sci USA 97:6421 CrossRefPubMedGoogle Scholar
  315. 315.
    Napier JA, Michaelson LV (2001) Lipids 36:761 PubMedGoogle Scholar
  316. 316.
    Watts JL, Browse J (2002) Proc Natl Acad Sci USA 99:5854 CrossRefPubMedGoogle Scholar
  317. 317.
    Parker-Barnes JM, Das T, Bobik E, Leonard AE, Thurmond JM, Chaung LT, Huang YS, Mukerji P (2000) Proc Natl Acad Sci USA 97:8284 CrossRefPubMedGoogle Scholar
  318. 318.
    Gunstone FD (1994) Prog Lipid Res 33:19 CrossRefPubMedGoogle Scholar
  319. 319.
    Khozin I, Adlerstein D, Bigongo C, Heimer YM, Cohen Z (1997) Plant Physiol 114:223 PubMedGoogle Scholar
  320. 320.
    Wallis JG, Browse J (1999) Arch Biochem Biophys 365:307 CrossRefPubMedGoogle Scholar
  321. 321.
    Qi B, Beaudoin F, Fraser T, Stobart AK, Napier JA, Lazarus CM (2002) FEBS Lett 510:159 CrossRefPubMedGoogle Scholar
  322. 322.
    Qiu X, Hong H, Mc Kenzie SL (2001) J Biol Chem 276:31 561 Google Scholar
  323. 323.
    Voss A, Reinhart M, Sankarappa S, Sprecher H (1991) J Biol Chem 266:19 995 Google Scholar
  324. 324.
    Moore SA, Hurt E, Yoder E, Sprecher H, Spector AA (1995) J Lipid Res 36:2433 PubMedGoogle Scholar
  325. 325.
    Ferdinandusse S, Denis S, Mooijer PA, Zhang Z, Reddy JK, Spector AA, Wanders RJ (2001) J Lipid Res 42:1987 PubMedGoogle Scholar
  326. 326.
    Su HM, Moser AB, Moser HW, Watkins PA (2001) J Biol Chem 276:38 115 Google Scholar
  327. 327.
    de Antueno RJ, Knickle, LC, Smith H, Elliot ML, Allen SJ, Nwaka S, Winther MD (2001) FEBS Lett 509:77 CrossRefPubMedGoogle Scholar
  328. 328.
    D'andrea S, Guillou H, Jan S, Catheline D, Thibault JN, Bouriel M, Rioux V, Legrand P (2002) Biochem J 364:49 PubMedGoogle Scholar
  329. 329.
    Metz JG, Roessler P, Facciotti D, Levering C, Dittrich F, Lassner M, Valentine R, Lardizabval K, Domergue F, Yamada A, Yazawa K, Knauf V, Browse J (2001) Science 293:290 CrossRefPubMedGoogle Scholar
  330. 330.
    Napier JA, Michaelson LV, Stobart AK (1999) Curr Opin Plant Biol 2:123 CrossRefPubMedGoogle Scholar
  331. 331.
    Cho HP, Nakamura M, Clarke SD (1999) J Biol Chem 274:37 335 Google Scholar
  332. 332.
    Leonard AE, Kelder B, Bobik EG, Chuang LT, Parker-Barnes JM, Thurmond JM, Kroeger PE, Kopchick JJ, Huang YS, Mukerji P (2000) Biochem J 347:719 CrossRefPubMedGoogle Scholar
  333. 333.
    Watts JL, Browse J (1999) Arch Biochem Biophys 362:175 CrossRefPubMedGoogle Scholar
  334. 334.
    Michaelson LV, Napier JA, Lewis M, Griffiths G, Lazarus CM, Stobart, AK (1998) FEBS Lett 439:215 CrossRefPubMedGoogle Scholar
  335. 335.
    Michaelson LV, Lazarus CM, Griffiths G, Napier JA, Stobart AK (1998) J Biol Chem 273:19 055 CrossRefGoogle Scholar
  336. 336.
    Knutzon DS, Thurmond JM, Huang YS, Chaudhary S, Bobik Jr EG, Chan GM, Kirchner SJ, Mukerji P (1998) J Biol Chem 273:29 360 CrossRefGoogle Scholar
  337. 337.
    Cho HP, Nakamura M, Clarke SD (1999) J Biol Chem 274:471 CrossRefPubMedGoogle Scholar
  338. 338.
    Napier JA, Hey SJ, Lacey DJ, Shewry PR (1998) Biochem J 330:611 PubMedGoogle Scholar
  339. 339.
    Sayanova O, Smith MA, Lapinskas P, Stobart AK, Dobson G, Christie WW, Shewry PR, Napier JA (1997) Proc Natl Acad Sci USA 94:4211 CrossRefPubMedGoogle Scholar
  340. 340.
    Sperling P, Lee M, Girke T, Zähringer U, Stymne S, Heinz E (2000) Eur J Biochem 267:3801 CrossRefPubMedGoogle Scholar
  341. 341.
    Girke T, Schmidt H, Zähringer U, Reski R, Heinz E (1998) Plant J 15:39 CrossRefPubMedGoogle Scholar
  342. 342.
    Yuan L, Kirchner SJ, Mukerji P, Knutzon DS (1999) Lipids 34:649 PubMedGoogle Scholar
  343. 343.
    Sakuradani E, Kobayashi M, Shimizu S (1999) Gene 238:445 CrossRefPubMedGoogle Scholar
  344. 344.
    Spychalla JP, Kinney AK, Browse J (1997) Proc Natl Acad Sci USA 94:1142 CrossRefPubMedGoogle Scholar
  345. 345.
    Zank TK, Zähringer U, Lerchl JE, Heinz E (2000) Biochem Soc Trans 28:654 CrossRefPubMedGoogle Scholar
  346. 346.
    Nichols D, Bowman J, Sanderson K, Mancuso-Nichols C, Lewis T, McMeekin, T, Nichols PD (1999) Curr Opin Biotechnol 10:240 CrossRefPubMedGoogle Scholar
  347. 347.
    Yazawa K (1996) Lipids 31:S297 PubMedGoogle Scholar
  348. 348.
    Watanabe K, Yazawa K, Kondo K, Kawaguchi A (1997) J Biochem 122:467 PubMedGoogle Scholar
  349. 349.
    Bisang C Long PF, Cortés J, Westcott J, Crosby J, Matharu AL, Cox RJ, Simpson TJ, Staunton J, Leadlay PF (1999) Nature 401:502 CrossRefPubMedGoogle Scholar
  350. 350.
    Heath RJ, Rock CO (2000) Nature 406:145 CrossRefPubMedGoogle Scholar
  351. 351.
    Allen EE, Facciotti D, Bartlett DH (1999) Appl Environ Microbiol 65:1710 PubMedGoogle Scholar
  352. 352.
    Tanaka M, Ueno A, Kawasaki K, Yumoto I, Ohgiya S, Hoshino T, Ishizaki K, Okuyama H, Morita N (1999) Biotechnol Lett 21:939 CrossRefGoogle Scholar
  353. 353.
    Leonard AE, Bobik EG, Dorado J, Kroeger PE, Chuang LT, Thurmond JM, Parker-Barnes JM, Das T, Huang YS, Mukerji P (2000) Biochem J 350:765 CrossRefPubMedGoogle Scholar
  354. 354.
    Huang J, Aki T, Yocochi T, Nakahara T, Honda D, Kawamoto S, Shigeta S, Ono K, Suzuki O (2003) Mar Biotechnol 5:451 CrossRefGoogle Scholar
  355. 355.
    Müller-Navarra DC, Brett MT, Liston AM, Goldman CR (2000) Nature 403:74 CrossRefPubMedGoogle Scholar
  356. 356.
    Iida I, Nakahara T, Yocochi T, Kamisaka Y, Yagi H, Yamaoka M, Suzuki O (1996) Journal Ferment Bioeng 81:76 CrossRefGoogle Scholar
  357. 357.
    Yokochi T, Honda D, Higashihara T, Nakahara T (1998) Appl Microbiol Biotechnol 49:72 CrossRefGoogle Scholar
  358. 358.
    Barclay WR, Meager KM, Abril JR (1994) J Appl Phycol 6:123 CrossRefGoogle Scholar
  359. 359.
    Lewis TE, Mooney BD, McMeekin TA, Nichols PD (1998) Chem Aust 65:37 Google Scholar
  360. 360.
    Vazhappilly R, Chen F (1998) Bot Mar 41:553 Google Scholar
  361. 361.
    Singh A, Ward OP (1997) Microbial production of docosahexaenoic acid (DHA, C22:6). In: Neidleman SL, Laskin AI (eds) Adv Appl Microbiol, Vol 45, pp 271–312 Google Scholar
  362. 362.
    Ratledge C (1998) Opportunities for marine microorganisms for the production of polyunsaturated FA. In: Le Gal Y, Muller-Feuga A (eds), Marine Microorganisms for Industry. Actes de colloque 21. IFREMER, Plouzane, France, pp 18–25 Google Scholar
  363. 363.
    Lewis TE, Nichols PD, McMeekin TA (1999) Mar Biotechnol 1:580 PubMedGoogle Scholar
  364. 364.
    Ratledge C (1993) Trends Biotechnol 11:278 Circular 886 (Rev 1) 1 CrossRefPubMedGoogle Scholar
  365. 365.
    Sajbidor J, Dobronova S, Certik M (1990) Biotechnol Lett 12:455 CrossRefGoogle Scholar
  366. 366.
    Gandhi SR, Weete JD (1991) J Gen Microbiol 137:1825 PubMedGoogle Scholar
  367. 367.
    Nichols DS, Nichols PD, McMeekin TA (1993) Antarct Sci 5:149 Google Scholar
  368. 368.
    Jøstensen, JP, Landfald B (1997) FEMS Microbiol Lett 151:95 CrossRefGoogle Scholar
  369. 369.
    Watanabe K, Sezaki K, Yazawa K, Hino A (1992) Nipp Suis Gakk 58:271 Google Scholar
  370. 370.
    Nichols DS, Hart P, Nichols PD, McMeekin TA (1996) Aquaculture 147:115 CrossRefGoogle Scholar
  371. 371.
    Lewis TE, Nichols PD, Hart PR, Nichols DS, McMeekin TA (1998) J World Aquacult Soc 29:313 Google Scholar
  372. 372.
    Gonzalezbaro MD, Pollero RJ (1998) Comp Biochem Physiol 119:747 Google Scholar
  373. 373.
    Erwin J, Bloch K (1964) Science 143:1006 PubMedGoogle Scholar
  374. 374.
    Zhukova NV, Kharlamenko VI (1999) Aquat Microb Ecol 17:153 Google Scholar
  375. 375.
    DeLong EF, Yayanos AA (1987) Appl Environ Microbiol 51:730 Google Scholar
  376. 376.
    Bowman JP, McCammon SA, Nichols DS, Skerratt JS, Rea SM, Nichols PD, McMeekin TA (1997) Int J Syst Bacteriol 47:1040 PubMedGoogle Scholar
  377. 377.
    Bowman JP, Gosink JJ, McCammon SA, Lewis TE, Nichols DS, Nichols PD, Skerratt JH, Staley JT, McMeekin TA (1998) Int J Syst Bacteriol 48:1171 Google Scholar
  378. 378.
    Hugenholtz P, Goebel BM, Pace NR (1998) J Bacteriol 180:4765 PubMedGoogle Scholar
  379. 379.
    Yano Y, Nakayama A, Yoshida K (1997) Appl Environ Microbiol 63:2572 Google Scholar
  380. 380.
    Kato C (1999) Molecular analysis of the sediment and isolation of extreme barophiles from the deepest Mariana Trench. In: Tsujii K (ed) Extremophiles in Deep-Sea Environments. Springer-Verlag, Tokyo, pp. 27–38 Google Scholar
  381. 381.
    Venkateswaren K, Dollhopf ME, Aller R, Stackebrandt E, Nealson KH (1998) Int J Syst Bacteriol 48:965 PubMedGoogle Scholar
  382. 382.
    Ivanova EP, Mikhailov VV (2001) Microbiology 70:10 CrossRefGoogle Scholar
  383. 383.
    Bozal N, Montes MJ, Tudela E, Jimenez F, Guinea J (2002) Int J Syst Evol Microbiol 52:195 PubMedGoogle Scholar
  384. 384.
    Nogi, Y, Kato C, Horikoshi K (1998) J Gen Appl Microbiol 44:289 CrossRefPubMedGoogle Scholar
  385. 385.
    Deming JW, Somers LK, Sraube WL, Swartz DG, MacDonnell MT (1988) Syst Appl Microbiol 10:152 Google Scholar
  386. 386.
    Yumoto I, Kawasaki K, Iwata H, Matsuyama H, Okuyama H (1998) Int J Syst Bacteriol 48:1357 PubMedGoogle Scholar
  387. 387.
    Urakawa H, Kita-Tsukamoto K, Steven S, Ohwada K, Colwell RR (1998) FEMS Microbiol Lett 165:373 CrossRefPubMedGoogle Scholar
  388. 388.
    Nogi Y, Kato C (1999) Extremophiles 3:71 CrossRefPubMedGoogle Scholar
  389. 389.
    Benediktsdóttir E, Verdonck L, Sproër C, Helgason S, Swings J (2000) Int J Syst Evol Microbiol 50:479 PubMedGoogle Scholar
  390. 390.
    Mountfort DO, Rainey FA, Burghardt J, Kaspar HF, Stackebrandt E (1998) Arch Microbiol 169:231 CrossRefPubMedGoogle Scholar
  391. 391.
    Nogi Y, Kato C, Horikoshi K (2002) Int J Syst Evol Microbiol 52:1527 CrossRefPubMedGoogle Scholar
  392. 392.
    Kawasaki K, Nogi Y, Hishinuma M, Nodasaka Y, Matsuyama H, Yumoto I (2002) Int J Syst Evol Microbiol 52:1455 CrossRefPubMedGoogle Scholar
  393. 393.
    Bowman JP, McCammon SA, Lewis TE, Skerratt JH, Brown JL, Nichols DS, McMeekin TA (1998) Microbiology 144:1601 PubMedGoogle Scholar
  394. 394.
    Nogi Y, Masui N, Kato C (1998) Extremophiles 2:1 CrossRefPubMedGoogle Scholar
  395. 395.
    Iwanami H, Yamaguchi T, Takeuchi M (1995) Nipp Suis Gakk 61:205 Google Scholar
  396. 396.
    Watanabe K, Ishikawa C, Ohtsuka I, Kamata M, Tomita M, Yazawa K, Muramatsu H (1997) Lipids 32:975 PubMedGoogle Scholar
  397. 397.
    Barbieri E, Paster BJ, Hughes D, Zurek L, Moser, DP, Teske A, Sogin ML (2001) Environ Microbiol 3:151 CrossRefPubMedGoogle Scholar
  398. 398.
    Ederington MC, Mcmanus GB, Harvey HR (1995) Limnol Oceanogr 40:860 Google Scholar
  399. 399.
    Nichols PD, Nichols DS, Lewis T, Bowman JP, Skerrat JH, McMeekin TA (1998) Novel bacteria as alternate sources of polyunsaturated FA for use in aquaculture and other industries. In: Le Gal Y, Muller-Feuga A (eds) Marine microorganisms for industry. IFREMER, Plouzané, France 26–32 Google Scholar
  400. 400.
    Russell NJ (1992) Physiology and molecular biology of psychrophilic micro-organisms. In: Herbert RA, Sharpe RJ (eds) Molecular Biology and Biotechnology of Extremeophiles. Blackie, Glasgow, pp 203–224 Google Scholar
  401. 401.
    Cronan JE, Rock CO (1996) Biosynthesis of membrane lipids. In: Neidhardt FC et al. (ed) Escherichia coli and Salmonella typhimurium: Cellular and Molecular Biology, p 612. American Society for Microbiology, Washington DC 149–160 Google Scholar
  402. 402.
    Fujii DK, Fulco AJ (1977) J Biol Chem 252:3660 PubMedGoogle Scholar
  403. 403.
    Rawlings BJ (1998) Nat Prod Rep 15:275 CrossRefPubMedGoogle Scholar
  404. 404.
    Siegenthaler PA, Belsky MM, Goldstein S (1967) Science 155:93 Google Scholar
  405. 405.
    Porter D (1990) Phylum Labyrinthulomycota. In: Margulis L, Corliss JO, Melkonian M, Chapman DJ (eds) Handbook of Protoctista. Jones and Bartlett, Boston pp 388–398 Google Scholar
  406. 406.
    Bahnweg G, Sparrow FK (1974) Am J Bot 61:754 Google Scholar
  407. 407.
    Raghukumar S, Gaertner A (1980) Veroff Inst Meeresforsch Bremerhaven 18:289 Google Scholar
  408. 408.
    Raghukumar S (1988) Transcr Br Mycol Soc 90:627 Google Scholar
  409. 409.
    Honda D, Yokochi T, Nakahara T, Erata M, Higashihara T (1998) Mycol Res 102:439 CrossRefGoogle Scholar
  410. 410.
    Naganuma T, Takasugi H, Kimura H (1998) Mar Ecol Prog Ser 162:105 Google Scholar
  411. 411.
    Cavalier-Smith T, Allsopp MTEP, Chao EE (1994) Philos Trans R Soc Lond B Biol Sci 346:387 Google Scholar
  412. 412.
    Nakahara T, Yokochi T, Higashihara T, Tanaka S, Yaguchi T, Honda D (1996) J Am Oil Chem Soc 73:1421 Google Scholar
  413. 413.
    Yaguchi T, Tanaka S, Yokochi T, Nakahara T, Higashihara T (1997) J Am Oil Chem Soc 74:1431 Google Scholar
  414. 414.
    Bajpai P, Bajpai BP, Ward OP (1991) Appl Microbiol Biotechnol 35:706 CrossRefGoogle Scholar
  415. 415.
    Bajpai P, Bajpai BP, Ward OP (1991) J Am Oil Chem Soc 68:509 Google Scholar
  416. 416.
    Li ZY, Ward OP (1994) J Indust Microbiol 13:238 CrossRefGoogle Scholar
  417. 417.
    Singh A, Ward OP (1996) J Indust Microbiol 16:370 CrossRefGoogle Scholar
  418. 418.
    Singh A, Wilson S, Ward OP (1996) World J Microbiol Biotechnol 12:76 CrossRefGoogle Scholar
  419. 419.
    Weete JD, Kim H, Ghandhi SR, Wang Y, Dute R (1997) Lipids 32:839 PubMedGoogle Scholar
  420. 420.
    Ellenbogen BB, Aaronson S, Goldstein S, Belsky M (1969) Comp Biochem Physiol 29:805 CrossRefGoogle Scholar
  421. 421.
    Findlay RH, Fell JW, Coleman NK, Vestal JR (1986) Biochemical indicators of the role of fungi and thraus-tochytrids in mangrove detrital systems. In: Moss ST (ed), The Biology of Marine Fungi. Cambridge University Press, Cambridge, pp 91–103 Google Scholar
  422. 422.
    Barclay W (1992) US Patent 5,130,242 Google Scholar
  423. 423.
    Bowles RD, Hunt AE, Bremer GB, Duchars MG, Eaton RA (1999) J Biotechnol 70:193 CrossRefGoogle Scholar
  424. 424.
    Huang J, Aki T, Hachida K, Yokochi T, Kawamoto S, Shigeta S, Ono K, Suzuki O (2001) J Am Oil Chem Soc 78:605 Google Scholar
  425. 425.
    Hammond BG, Mayhew DA, Naylor MW, Ruecker FA, Mast RW, Sander WJ (2001) Regul Toxicol Pharmacol 33:192 CrossRefPubMedGoogle Scholar
  426. 426.
    Barclay WR (1994) US Patent 5,340,742 Google Scholar
  427. 427.
    Barclay W, Zeller S (1996) J World Aquacult Soc 27:314 Google Scholar
  428. 428.
    Hammond BG, Mayhew DA, Robinson K, Mast RW, Sander WJ (2001) Regul Toxicol Pharmacol 33:356 CrossRefPubMedGoogle Scholar
  429. 429.
    Hammond BG, Mayhew DA, Naylor MW, Holson JF, Nemec MD, Mast RW, Sander WJ (2001) Regul Toxicol Pharmacol 33:205 CrossRefPubMedGoogle Scholar
  430. 430.
    Fitch Haumann B (1999) INFORM 9:1108 Google Scholar
  431. 431.
    Narciso I, Pousao-Ferreira P, Passos A, Luis O (1999) Aquacult Res 30:21 CrossRefGoogle Scholar
  432. 432.
    Carter CG, Bransden MP, Lewis TE, Nichols PD (2003) Mar Biotechnol 5:480 CrossRefPubMedGoogle Scholar
  433. 433.
    Bull AT, Goodfellow M, Slater JH (1992) Annu Rev Microbiol 46:219 CrossRefPubMedGoogle Scholar
  434. 434.
    Bull AT, Ward AC, Goodfellow M (2000) Microbiol Mol Biol R 46:573 CrossRefGoogle Scholar
  435. 435.
    Certik M, Shimizu S (1999) J Biosci Bioeng 87:1 CrossRefGoogle Scholar
  436. 436.
    Becker CC, Kyle DJ (1998) Food Technol 52:68 Google Scholar
  437. 437.
    Arts MT, Ackman RG, Holub BJ (2001) Can J Fish Aquat Sci 58:122 CrossRefGoogle Scholar
  438. 438.
    Sargent JR, Tacon AGJ (1999) P Nutr Soc 58:377 Google Scholar
  439. 439.
    Sargent JR (1995) (n-3) polyunsaturated FA and farmed fish. In: Hamilton, RJ, Rice, RD (eds.), Fish Oil: Technology, Nutrition and Marketing. Barnes and Associates, Bucks, pp 67–94 Google Scholar
  440. 440.
    Peng J, Larondelle Y, Ackman RG, Rollin X (2003) Comp Biochem Physiol Pt B 134:335 CrossRefGoogle Scholar
  441. 441.
    Bell JG, Tocher DR, Farndale BM, Cox DI, McKinney RW, Sargent JR (1997) Lipids 32:515 PubMedGoogle Scholar
  442. 442.
    Ackman RG (1980) Fish lipids. In: Connell, JJ (ed.), Advances in Fish Science and Technology. Fishing News, Farnham, p 86 Google Scholar
  443. 443.
    Viga A, Grahl-Nielsen O (1990) Comp Biochem Physiol Pt B 96:721 CrossRefGoogle Scholar
  444. 444.
    Pickova J, Kiessling A, Petterson A, Dutta PC (1999) Fish Physiol Biochem 21:147 CrossRefGoogle Scholar
  445. 445.
    Ould El Kebir MV, Barnathan G, Siau Y, Miralles J, Gaydou EM (2003) J Agric Food Chem 51:1942 CrossRefPubMedGoogle Scholar
  446. 446.
    Fodor E, Jones RH, Buda C, Kitajka K, Dey I, Farkas T (1995) Lipids 30:1119 PubMedGoogle Scholar
  447. 447.
    Lee KH, Jeong ICH, Suh JS, Jung WJ, Kim CG, Lee BH (1986) Han'guk Susan Hakhoechi 19:423 Google Scholar
  448. 448.
    Tritar B, Attia-Chaouch S, Hammami M (1997) Ichtyophysiol Acta 20:67 Google Scholar
  449. 449.
    Saito H, Ishihara K, Murase T (1997) J Sci Food Agric 73:53 CrossRefGoogle Scholar
  450. 450.
    Bandarra MN, Batista I, Nunes ML, Empis JM, Christie WW (1997) J Food Sci 62:40 Google Scholar
  451. 451.
    Gamez-Meza N, Higuera-Ciapara I, Calderon de la Barca AM, Vazquez-Moreno L, Noriega-Rodriguez J, Angulo-Guerrero O (1999) Lipids 34:639 PubMedGoogle Scholar
  452. 452.
    Tanakol R, Yazici Z, Sener E, Sencer, E (1999) Lipids 34:291 PubMedGoogle Scholar
  453. 453.
    Marquez-Ruiz G, Velasco J, Dobarganes C (2000) Eur Food Res Technol 211:13 CrossRefGoogle Scholar
  454. 454.
    Hilbert G, Lillemark L, Balchen S, Højskov CS (1998) Chemosphere 37:1241 CrossRefPubMedGoogle Scholar
  455. 455.
    Njinkoué JM, Barnathan G, Mirallès J, Gaydou EM, Samb A (2002) Comp Biochem Physiol 131B:395 Google Scholar
  456. 456.
    Gunstone FD (2002) Market report. Lipid Technology Newsletter 8:5 Google Scholar
  457. 457.
    Rees JF, Cure K, Piyatiratitivorakul S, Sorgeloos P, Menasveta P (1994) Aquaculture 122:193 CrossRefGoogle Scholar
  458. 458.
    Salhi M, Izquierdo MS, Hernandezcruz CM, Gonzalez M, Fernandezpalacios H (1994) Aquaculture 124:275 CrossRefGoogle Scholar
  459. 459.
    Pike IH, Barlow SM (1999) Fish meal and oil to the year 2010: supplies for aquaculture. Presented at World Aquaculture 1999, Sydney, Australia, April 26–May 2 1999, Abstract, p 603 Google Scholar
  460. 460.
    Molyneaux M, Chong ML (1998) Food Technol 52:56 Google Scholar
  461. 461.
    Barlow SM (2002) 2nd Seafood By-Products Conference, Alaska, USA Google Scholar
  462. 462.
    Mukherjee KD (1999) INFORM 10:308 Google Scholar

Authors and Affiliations

  1. 1.Centre de Nantes, Laboratoire Génie Alimentaire, Département Valorisation des ProduitsInstitut Français pour l'Exploitation de la Mer (IFREMER)Nantes Cedex 03France
  2. 2.Pole Mer et Littoral, Laboratoire de Chimie Marine, Groupe SMAB (EA 2160), Substances marines à activité biologiqueUniversité de NantesNantes Cedex 03France

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