Geometrical trans lipid isomers: A new target for lipidomics

ChemBioChem

Volumn 6, Issue 10, 2005, Pages 1722-1734

  Ferreri, Carla ^a   Chatgilialoglu, Chryssostomos ^a  

^a CNR   (Italy)

Author keywords

Fatty acids; Isomerization; Lipidomics; Lipids; Phospholipids

Indexed keywords

ARACHIDONIC ACID; BIOCHEMICAL MARKER; FATTY ACID DERIVATIVE; FREE RADICAL; LIPID; TRANS FATTY ACID;

BIOMIMETICS; CELL MEMBRANE; CIS TRANS ISOMERISM; EUKARYOTIC CELL; GEOMETRY; HUMAN; ISOMERISM; ISOMERIZATION; LIPID ANALYSIS; LIPID METABOLISM; LIPOGENESIS; METABOLIC REGULATION; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; SIGNAL TRANSDUCTION; TRANS ISOMER;

ANIMALS; CELL MEMBRANE; HUMANS; ISOMERISM; LIPID METABOLISM; MEMBRANE LIPIDS; STRUCTURE-ACTIVITY RELATIONSHIP; TRANS FATTY ACIDS;

EUKARYOTA;

EID: 26944461594     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200500109     Document Type: Review

References (119)

1. a) F. Spener, M. Lagarde, A. Géloën, M. Record, Eur. J. Lipid Sci. Technol. 2003, 105, 481-482;
2. b) M. Lagarde, A. Géloën, M. Record, D. Vance, F. Spener, Biochim. Biophys. Acta 2003, 1634, 61.
3. http://www.lipidmaps.org
4. http://www.musc.edu/BCMB/cobre
5. http://www.lipidomics.net
6. a) Lipid Second Messengers (Eds.: S. G. Laychock, R. P. Rubin), CRC Press, New York, 1998;
7. b) K. Sato, S. Ueno, J. Yano, Prog. Lipid Res. 1999, 38, 91-116;
8. c) Biochemistry of Lipids, Lipoproteins and Membranes (Eds.: D. E. Vance, J. E. Vance), 4th ed., Elsevier, Amsterdam, 2002;
9. d) R. Bittman, Chem. Phys. Lipids 2004, 129, 111-131;
10. e) X. Han, Cell. Mol. Life Sci. 2004, 61, 1896-1906.
11. a) M. Pulfer, R. C. Murphy, Mass Spectrom. Rev. 2003, 22, 332-364;
12. b) X. Han, R. W. Gross, J. Lipid Res. 2003, 44, 1071-1079;
13. c) Y. Y. Hsu, J. Turk, J. Am. Soc. Mass Spectrom. 2003, 14, 352-363;
14. d) H. Y. Kim, T. C. L. Wang, Y. C. Ma, Anal. Chem. 1994, 66, 3977-3982.
15. I. M. Cristea, M. Degli Esposti, Chem. Phys. Lipids 2004, 129, 133-160.
16. J. S. Forrester, S. B. Milne, P. T. Ivanova, H. A. Brown, Mol. Pharmacol. 2004, 65, 813-821.
17. a) F. A. Kummerow, Q. Zhou, M. M. Mahfouz, M. R. Smiricky, C. M. Grieshop, D. J. Schaeffer, Life Sci. 2004, 74, 2707-2723;
18. b) A. Ascherio, Am. J. Med. 2002, 113, 9S-12S;
19. c) W. C. Willett, M. J. Stampfer, J.E. Manson, G. A. Colditz, F. E. Speizer, B. A. Rosner, L. A. Sampson, C. H. Hennekens, Lancet 1993, 341, 581-585.
20. J. F. Wilson, Scientist 2003, 17, 34-36.
21. S. J. Vayttaden, S. M. Ajay, U.S. Bhalla, ChemBioChem 2004, 5, 1365-1374.
22. Free Radicals in Biology and Medicine, 3rd ed. (Eds.: B. Halliwell, J. M. C. Gutteridge), Oxford University Press, Oxford, 2001.
23. a) Z. Z. Chong, J. Q. Kang, K. Maiese, Antioxid. Redox Signaling 2004, 6, 277-287;
24. b) A. W. Girotti, T. Kriska, Antioxid. Redox Signaling 2004, 6, 301-310.
25. H. Sies, Free Radical Biol. Med. 1999, 27, 916-921.
26. V. E. Kagan, P. J. Quinn, Antioxid. Redox Signaling 2004, 6, 199-202.
27. C. Chatgilialoglu, C. Ferreri, Acc. Chem. Res. 2005, 38, 441-448.
28. B. G. Fox, K. S. Lyle, C. E. Rogge, Acc. Chem. Res. 2004, 37, 421-429.
29. Results from a search in the ISI Web database for the topic "trans fatty acid" over the period 1998-2004.
30. H. Keweloh, H. J. Heipieper, Lipids 1996, 31, 129-137.
31. C. Wayne Moss, M. A. Lambert-Fair, J. Clin. Microbiol. 1989, 27, 1467-1470;
32. C. Wayne Moss, M. J. Daneshvar, J. Clin. Microbiol. 1992, 30, 2511-2512.
33. a) H. J. Heipieper, F. Meinhardt, A. Segura, FEMS Microbiol. Lett. 2003, 229, 1-7;
34. b) H. J. Heipeiper, G. Neumann, N. Kabelitz, M. Kastner, H. H. Richnow, Appl. Microbiol. Biotechnol. 2004, 66, 285-290;
35. c) V. Pedrotta, B. Witholt, J. Bacteriol. 1999, 181J, 3256-3261;
36. d) H. Okuyama, A. Ueno, D. Enari, N. Morita, T. Kusano, Arch. Microbiol. 1998, 169, 29-35.
37. R. Holtwick, F. Meinhardt, H. Keweloh, Appl. Environ. Microbiol. 1997, 63, 4292-4297
38. R. Holtwick, H. Keweloh, F. Meinhardt, Appl. Environ. Microbiol. 1999, 65, 2644-2649
39. L. J. Halverson, M. K. Firestone, Appl. Environ. Microbiol. 2000, 66, 2414-2421.
40. L. P. L. van de Vijver, A. F. M. Kardinaal, C. Couet, A. Aro, A. Kafatos, L. Steingrimdottir, J. A. Amorim Cruz, O. Moreiras, W. Becker, J. M. M. van Amelsvoort S. Vidal-Jessel, I. Salminen, J. Moschandreas, N. Sigfusson, I. Martins, A. Carbajal, A. Ytterfors, G. van Poppel, Eur. J. Clin. Nutr. 2000, 54, 126-135.
41. W. Schwarz, Eur. J. Lipid Sci. Technol. 2000, 102, 633-635.
42. Trans Fatty Acids in Human Nutrition (Eds.: J. L. Sébédio, W. W. Christie), The Oily Press, Dundee, 1998.
43. A. Romero, C. Cuesta, F. J. Sanchez-Muniz, Nutr. Res. 2000, 20, 599-608.
44. A. Aro in Trans Fatty Acids in Human Nutrition (Eds.: J. L. Sébédio, W. W. Christie) The Oily Press, Dundee, 1998, pp. 235-260.
45. T. L. Roberts, D. A. Wood, R. A. Riemersma, P. J. Gallagher, F. C. Lampe, Lancet 1995, 345, 278-282.
46. E. Larquè, S. Zamora, A. Gil, Early Hum. Dev. 2001, 65, 531-541.
47. F. B. Hu, M. J. Stampfer, J. E. Manson, E. Rimm, G. A. Colditz, B. A. Rosner, C. H. Hennekens, W. C. Willett, N. Engl. J. Med. 1997, 337, 1491-1499.
48. M. Bender Brandt, L. A. LeGault, J. Food Compos. Anal. 2003, 16, 383-393.
49. K. W. J. Wahle, S. D. Heys, D. Rotondo, Prog. Lipid Res. 2004, 43, 553-587.
50. a) R. H. Coots, J. Lipid Res. 1964, 5, 473-476;
51. b) P. O. Egwim, D. S. Sgoutas, J. Nutr. 1971, 101, 307-314;
52. c) R. L. Anderson, C. S. Fullmer, Jr., E. J. Hollenbach, J. Nutr. 1975, 105, 393-400;
53. d) I. Reichwald-Hacker, S. Grosse-Oetringhaus, I. Kiewitt, K. D. Mukherjee, Biochim. Biophys. Acta 1979, 575, 327-334.
54. a) R. L. Wolff, B. Entressangles, Biochim. Biophys. Acta 1994, 1211, 198-206;
55. b) B. Koletzko, T. Decsi, Clin. Nutr. 1997, 16, 229-237;
56. c) J. L. Sébédio, S. H. F. Vermunt, I. M. Chardigny, B. Beaufrére, R. P. Mensink, R. A. Armstrong, W. W. Christie, J. Niemela, G. Hènon, R. A. Riemersma, Eur. J. Clin. Nutr. 2000, 54, 104-113.
57. U. Roy, O. Loreau, M. Balazy, Bioorg. Med. Chem. Lett. 2004, 14, 1019-1022.
58. M. Guzman, W. Klein, T. G. del Pulgar, M. J. Geelen, Lipids 1999, 34, 381-386.
59. A. Gurvitz, B. Hamilton, H. Ruis, A. Hartig, J. Biol. Chem. 2001, 276, 895-903.
60. O. Berdeaux, J. M. Chardigny, J. L. Sébédio, T. Mairot, D. Poullain, J. M. Vatèle, J. P. Noël, J. Lipid Res. 1996, 37, 2244-2250.
61. O. Berdeaux, J. P. Blond, L. Bretillon, J. M. Chardigny, T. Mairot, J. M. Vatèle, D. Poullain, J. L. Sébédio, Mol. Cell. Biochem. 1998, 185, 17-25.
62. F. A. Kummerow, Q. Zhou, M. M. Mahfouz, M. R. Smiricky, C. M. Grieshop, D. J. Schaeffer, Life Sci. 2004, 74, 2707-2723.
63. D. Anagnostopoulos, C. Chatgilialoglu, C. Ferreri, A. Samadi, A. Siafaka-Kapadai, Bioorg. Med. Chem. Lett. 2005, 15, 2766-2770.
64. S. Schreiber, Chem. Eng. News 2003, 81, 51-61.
65. Phospholipids Handbook (Ed.: G. Cevc), Marcel Dekker, New York, 1993.
66. J. E. Baezinger, H. C. Jarrell, I. C. P. Smith, Biochemistry 1992, 31, 3377-3385.
67. a) C. Chatgilialoglu, L. Zambonin, A. Altieri, C. Ferreri, Q. G. Mulazzani, L. Landi, Free Radical Biol. Med. 2002, 33, 1681-1692;
68. b) C. Chatgilialoglu, C. Ferreri, M. Ballestri, Q. G. Mulazzani, L. Landi, J. Am. Chem. Soc. 2000, 122, 4593-4601.
69. R. M. Sargis, P. V. Subbaiah, Biochemistry 2003, 42, 11533-11543.
70. C. Roach, S. E. Feller, J. A. Ward, S. Raza Shaikh, M. Zerouga, W. Stillwell, Biochemistry 2004, 43, 6344-6351.
71. S.-L. Niu, D. C. Mitchell, B. J. Litman, Biochemistry 2005, 44, 4458-4465.
72. a) H. W. Cook, Biochim. Biophys. Acta 1978, 531, 245-256;
73. b) G. M. Helmkamp, Jr., Biochemistry 1980, 19, 2050-2056;
74. c) F. A. Kummerow, Q. Zhou, M. M. Mahfouz, Am. J. Clin. Nutr. 1999, 70, 832-838;
75. d) J. Rauch, J. Gumperz, C. Robinson, M. Skold, C. Roy, D. C. Young, M. Lafleur, D. B. Moody, M. B. Brenner, C. E. Costello, S. M. Behar, J. Biol. Chem. 2003, 278, 47508-47515.
76. a) C. Walling, W. Helmreich, J. Am. Chem. Soc. 1959, 81, 1144-1148;
77. b) D. S. Sgoutas, F. A. Kummerow, Lipids 1969, 4, 283-287;
78. c) C. Chatgilialoglu, M. Ballestri, C. Ferreri, D. Vecchi, J. Org. Chem. 1995, 60, 3826-3831.
79. C. Chatgilialoglu, A. Altieri, H. Fischer, J. Am. Chem. Soc. 2002, 124, 12816-12823.
80. C. Chatgilialoglu, A. Samadi, M. Guerra, H. Fischer, ChemPhysChem 2005, 6, 286-291.
81. C. Ferreri, C. Costantino, L. Perrotta, L. Landi, Q. G. Mulazzani, C. Chatgilialoglu, J. Am. Chem. Soc. 2001, 123, 4459-4468.
82. P. Wardman in S-Centered Radicals (Ed.: Z. B. Alfassi), Wiley, Chichester, 1999, pp. 289-309.
83. O. Augusto, M. B. Bonini, A.M. Amanso, E. Linares, C. C. X. Santos, S. L. De Menezes, Free Radical Biol. Med. 2002, 32, 841-859.
84. H. Jiang, N. Kruger, D. R. Lahiri, D. Wang, J.-M. Vatèle, M. Balazy, J. Biol. Chem. 1999, 274, 16235-16241.
85. R. E. Huie, Toxicology 1994, 89, 193-216.
86. B. Halliwell, M. L. Hu, S. Louie, T. R. Duvall, B. K. Tarkington, P. Motchnik, C. E. Cross, FEBS Lett. 1992, 313, 62-66.
87. E. Ford, M. N. Hughes, P. Wardman, Free Radical Biol. Med. 2002, 32, 1313-1323.
88. C. Ferreri, M. R. Faraone Mennella, C. Formisano, L. Landi, C. Chatgilialoglu, Free Radical Biol. Med. 2002, 33, 1516-1526.
89. J. Bus, I. Sies, M. S. F. Lie Ken Jie, Chem. Phys. Lipids 1977, 18, 130-144.
90. A. Samadi, I. Andreu, C. Ferreri, S. Dellonte, C. Chatgilialoglu, J. Am. Oil Chem. Soc. 2004, 81, 753-758.
91. a) M. R. Tosi, M. T. Rodriguez-Estrada, G. Lercker, A. Poerio, A. Trinchero, A. Reggiani, V. Tugnoli, Int. J. Mol. Med. 2004, 14, 93-100;
92. b) T. Engan, K. S. Bjerve, A. L. Hoe, J. Krane, Blood 1995, 85, 1323-1330;
93. c) J. D. Bell, M. L. Barnard, H. G. Parkes, E. L. Thomas, C. H. Brennan, S. C. Cunnane, P. C. Dagnelie, J. Lipid Res. 1996, 37, 1664-1674;
94. d) P. Pollesello, O. Eriksson, K. Höckerstedt, Anal. Biochem. 1996, 236, 41-48.
95. C. Ferreri, C. Costantino, L. Landi, Q. G. Mulazzani, C. Chatgilialoglu, Chem. Commun. 1999, 407-408.
96. a) S. Adhikari, H. Sprinz, O. Brede, Res. Chem. Intermed. 2001, 27, 549-559;
97. b) H. Sprinz, S. Adhikari, O. Brede, Adv. Colloid Interface Sci. 2001, 89-90, 313-325;
98. c) H. Sprinz, J. Schwinn, S. Naumov, O. Brede, Biochim. Biophys. Acta 2000, 1483, 91-100.
99. C. Ferreri, S. Kratzsch, L. Landi, O. Brede, Cell. Mol. Life Sci. 2005, 62, 834-847.
100. a) Y. Yamamoto, E. Niki, Y. Kamiya, H. Shimasaki, Biochim. Biophys. Acta 1984, 795, 332-340;
101. b) L. R. C. Barclay, Can. J. Chem. 1993, 71, 1-16.
102. A. Prager, N. H. A. Terry, D. Murray, Int. J. Radiat. Biol. 1993, 64, 71-81.
103. a) C. Savoye, C. Swenberg, S. Hugot, D. Sy, R. Sabattier, M. Charlier, M. Spotheim-Maurizot, Int. J. Radiat. Biol. 1997, 71, 193-202;
104. b) J. A. Aguilera, G. L. Newton, R. C. Fahey, J. F. Ward, Radiat. Res. 1992, 130, 194-204;
105. c) A. W. T. Koning, J. Damen, W. B. Trieling, Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 1979, 35, 343-350.
106. M. Shahid Akhlaq, H.-P. Schuchmann, C. von Sonntag, Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 1987, 51, 91-102.
107. Liposomes: a Practical Approach (Ed.: R. R. C. New), IRL Press, Oxford, 1990.
108. C. Ferreri, A. Samadi, F. Sassatelli, L. Landi, C. Chatgilialoglu, J. Am. Chem. Soc. 2004, 126, 1063-1072.
109. R. G. Allen, A. K. Balin in Critical Reviews of Oxidative Stress and Aging (Eds.: R. G. Cutler, H. Rodriguez), World Scientific, Singapore, 2003, pp. 3-23.
110. H. Sies, Free Radical Biol. Med. 1999, 27, 916-921.
111. C. von Sonntag, The Chemical Basis of Radiation in Biology, Taylor and Francis, Oxford, 1987.
112. J. Stubbe, Chem. Commun. 2003, 2511-2513.
113. B. E. Holmes, G. Navon, G. Stein, Nature 1967, 163, 1087-1091.
114. C. Ferreri, I. Manco, M. R. Faraone-Mennella, A. Torreggiani, M. Tamba, C. Chatgilialoglu, ChemBioChem 2004, 5, 1710-1712.
115. a) K. Uchida, E. R. Stadtman, Proc. Natl. Acad. Sci. USA 1992, 89, 4544-4548;
116. b) J. R. Requena, M. X. Fu, M. W. Ahmed, A. I. Jenkins, T. J. Lyons, J. W. Baynes, S. R. Thorpe, Biochem. J. 1997, 322, 317-325;
117. c) L. A. Van-derVeen, A. Druckova, J. N. Riggins, J. L. Sorrells, F. P. Guengerich, L. J. Marnett, Biochemistry 2005, 44, 5024-5033.
118. C. Ferreri, S. Kratzsch, O. Brede, B. Marciniak, C. Chatgilialoglu, Free Radical Biol. Med. 2005, 38, 1180-1187.
119. R. McDonald, M. M. Mossoba in Food Lipids Chemistry, Nutrition and Biotechnology (Eds.: C. C. Akoh, D. B. Min), Marcel Dekker, New York, 2002, pp. 169-204.