cis-trans Isomerization of monounsaturated fatty acid residues in phospholipids by thiyl radicals

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4593-4601

  Chatgilialoglu, Chryssostomos ^a   Ferreri, Carla ^a,b   Ballestri, Marco ^a   Mulazzani, Quinto G ^a   Landi, Laura ^c  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DIOLEOYLPHOSPHATIDYLCHOLINE; MONOUNSATURATED FATTY ACID; OLEIC ACID; OXYGEN; PHOSPHOLIPID; RADICAL;

ARTICLE; CIS TRANS ISOMERISM; MEMBRANE FLUIDITY; PHOSPHOLIPID VESICLE;

EID: 0034679015     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994169s     Document Type: Article

References (96)

1. (a) Lang, J.; Vigo-Pelfrey, C.; Martin, F. Chem. Phys. Lipids 1990, 53, 91-101.
2. (b) For hydrogenated vegetable and marine oils, see: Ovesen, L.; Leth, T.; Hausen, K. Lipids 1996, 31, 971-975 and references therein.
3. Keweloh, H.; Heipieper, H. J. Lipids 1996, 31, 129-137.
4. Tung, B. S.; Unger, E. R.; Levin, B.; Brasitus, T. A.; Getz, G. S. J. Lipid Res. 1991, 32, 1025-1038.
5. Basu, J.; Kundo, M.; Chakrabarti, P. Arch. Biochem. Biophys. 1986, 250, 382-389.
6. Wolff, R. L.; Entressangles, B. Biochim. Biophys. Acta 1994, 1211, 198-206.
7. Loffeld, B.; Keweloh, H. Lipids 1996, 31 811-815.
8. Okuyama, H.; Okajima, N.; Sasaki, S.; Higashi, S.; Murata, N. Biochim. Biophys. Acta 1991, 1084, 13-20.
9. (a) Heipieper, H.-J.; Diefenbach, R.; Keweloh, H. Appl. Environ. Microbiol. 1992, 58, 1847-1852.
10. (b) Keweloh, H.; Heipieper, H. J. Lipids 1996, 31, 129-137.
11. Helmkamp, G. M., Jr. Biochemistry 1980, 19, 2050-2056.
12. (a) Ratnayake, W. M. N.; Chen, Z.-Y. Lipids 1996, 31 (Suppl.), 279-282 and references therein.
13. (b) For a review, see: Katan, M. B.; Zock, P. L.; Mensink, R. P. Annu. Rev. Nutr. 1995, 15, 473-493.
14. For some representative reviews, see: Porter, N. A. Acc. Chem. Res. 1986, 19, 262-268. Niki, E. In Organic Peroxides; Ando, W., Ed.; Wiley: New York; 1992; pp 764-787. Barclay, L. C. R. Can. J. Chem. 1993, 33, 1-16.
15. For some representative reviews, see: Porter, N. A. Acc. Chem. Res. 1986, 19, 262-268. Niki, E. In Organic Peroxides; Ando, W., Ed.; Wiley: New York; 1992; pp 764-787. Barclay, L. C. R. Can. J. Chem. 1993, 33, 1-16.
16. For some representative reviews, see: Porter, N. A. Acc. Chem. Res. 1986, 19, 262-268. Niki, E. In Organic Peroxides; Ando, W., Ed.; Wiley: New York; 1992; pp 764-787. Barclay, L. C. R. Can. J. Chem. 1993, 33, 1-16.
17. For the autoxidation of methyl oleate, see: Porter, N. A.; Mills, K. A.; Carter, R. L. J. Am. Chem. Soc. 1994, 116, 6690-6696.
18. Muller, S. N.; Batra, R.; Senn, M.; Giese, B.; Kisel M.; Shadyro, O. J. Am. Chem. Soc. 1997, 119, 2795-2803.
19. For example, see: Sonnet, P. E. Tetrahedron 1980, 36 557-604. Saltiel, J.; Sears, D. F., Jr.; Ko, D.-H.; Park, K.-M. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. H., Song, P. S., Eds.; CRC Press: Boca Raton, 1995; Chapter 1.
20. For example, see: Sonnet, P. E. Tetrahedron 1980, 36 557-604. Saltiel, J.; Sears, D. F., Jr.; Ko, D.-H.; Park, K.-M. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. H., Song, P. S., Eds.; CRC Press: Boca Raton, 1995; Chapter 1.
21. Chatgilialoglu, C.; Ballestri, M.; Ferreri, C.; Vecchi, D. J. Org. Chem. 1995, 60, 3826-3831.
22. 19
23. (a) Pallen, R. H.; Sivertz, C. Can. J. Chem. 1957, 35, 723-733.
24. (b) Walling, C.; Helmreich, W. J. Am. Chem. Soc. 1959, 81, 1144-1148.
25. (c) For a review of early work, see: Kice, J. L. In Free Radicals; Kochi, J. K., Ed.; Wiley: New York, 1973; Vol. 2, pp 711-740.
26. For recent reviews, see: (a) Chatgilialoglu, C.; Guerra, M. In Supplement S: The Chemistry of Sulfur-containing Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: London, 1993; Chapter 8, pp 363-394.
27. For recent reviews, see: (a) Chatgilialoglu, C.; Guerra, M. In Supplement S: The Chemistry of Sulfur-containing Functional Groups; Patai, S., Rappoport, Z., Eds.; Wiley: London, 1993; Chapter 8, pp 363- 394. (b) Chatgilialoglu, C.; Bertrand, M. P.; Ferreri, C. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; pp 312-354.
28. Sulfur-centered Reactive Intermediates in Chemistry and Biology, Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990.
29. 2SH, as euroneously reported.
30. 24
31. Schöneich, C.; Bonifacic, M.; Dillinger, U.; Asmus, K.-D. In Sulfur-Centered Reactive Intermediates in Chemistry and Biology; Chatgilialoglu, C., Asmus, K.-D., Eds.; Plenum Press: New York, 1990; pp 367-376.
32. Schwinn, J.; Sprinz, H.; Dröβer, K.; Leistner, S.; Brede, O. Int. J. Radiat. Biol. 1998, 74, 359-365.
33. Jiang, H.; Kruger, N.; Lahiri, D. R.; Wang, D.; Vatèle, J.-M.; Balazy, M. J. Biol. Chem. 1999, 274, 16235-16241.
34. Newton, G. L.; Aguilera, J. A.; Kim, T.; Ward, J. F.; Fahey, R. C. Radiat. Res. 1996, 146, 206-215 and references therein.
35. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513 and references therein.
36. Ross, A. B., Mallard, W. G.; Helman, W. P.; Buxton, G. V.; Huie, R. E.; Neta, P. NDRL-NIST Solution Kinetic Database - Ver. 3; Notre Dame Radiation Laboratory; Notre Dame, IN; NIST Standard Reference Data: Gaithersburg, MD, 1998.
37. -1 seems reasonable.
38. Spinks, J. W. T.; Woods, R. J. An Introduction to Radiation Chemistry, 3rd ed.; Wiley: New York, 1990; p 421.
39. Tronche, C.; Martinez, F. N.; Horner, J. H.; Newcomb, M.; Senn, M.; Giese, B. Tetrahedron Lett. 1996, 33, 5845-5848.
40. Moussebois, C.; Dale, J. J. Chem. Soc. 1966, 260-264, 264-267.
41. -4 M.
42. Cipollone, M.; di Palma, C.; Pedulli, G. F. Appl. Magn. Reson. 1992, 3, 98-102.
43. 11 has been measured in water; see: Mark, G.; Schuchmann, M. N.; Schuchmann, H. P.; von Sonntag, C. J. Photochem. Photobiol., A 1990, 55, 157-168. von Piechowski, M.; Thelen, M. A.; Hoigne, J.; Buehler, R. E. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 1448-1454. However, the rate constants for the reaction of an alkyl radical with oxygen are similar in organic solvents (cf. Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095-5099).
44. 11 has been measured in water; see: Mark, G.; Schuchmann, M. N.; Schuchmann, H. P.; von Sonntag, C. J. Photochem. Photobiol., A 1990, 55, 157-168. von Piechowski, M.; Thelen, M. A.; Hoigne, J.; Buehler, R. E. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 1448-1454. However, the rate constants for the reaction of an alkyl radical with oxygen are similar in organic solvents (cf. Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095-5099).
45. 11 has been measured in water; see: Mark, G.; Schuchmann, M. N.; Schuchmann, H. P.; von Sonntag, C. J. Photochem. Photobiol., A 1990, 55, 157-168. von Piechowski, M.; Thelen, M. A.; Hoigne, J.; Buehler, R. E. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 1448-1454. However, the rate constants for the reaction of an alkyl radical with oxygen are similar in organic solvents (cf. Maillard, B.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1983, 105, 5095-5099).
46. Barclay, L. R. C.; McNeil, J. M.; VanKessel, J.; J. Forrest, B.; Porter, N. A.; Lehman, L. S.; Smith, K. J.; Ellington, J. C., Jr. J. Am. Chem. Soc. 1984, 106, 6740-6747.
47. The transesterification in an alkaline medium is preferable, as reported by Kramer, J. F. K.; Fellner, V.; Dugan, M. E. R.; Sauer, F. D.; Mossoba M. M.; Yurawecz, M. P. Lipids 1997, 32, 1219-1228.
48. Handbook of Chemistry and Physics, 74th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, 1993-94.
49. Wagner, P. J.; Sedon, J. H.; Lindstrom, M. J. J. Am. Chem. Soc. 1978, 100, 2579-2580.
50. Ito, O. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; pp 193-224.
51. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323.
52. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
53. -1.
54. (a) Chatgilialoglu, C.; Dickhaut, J.; Giese, B. J. Org. Chem. 1991, 56, 6399-6403.
55. (b) Chatgilialoglu, C.; Newcomb, M. Adv. Organomet. Chem. 1999, 44, 67-112.
56. (a) Chatgilialoglu, C.; Ballestri, M.; Vecchi, D.; Curran, D. P. Tetrahedron Lett. 1996, 37, 6383-6386.
57. (b) Haque, M. B.; Roberts, B. P.; Tocher, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 2881-2889.
58. 3SiH concentrations of 0.4, 0.6, 0.7, 0.8, 0.9, and 1.0 M, respectively.
59. -1.
60. • radicals from a variety of substituted radicals 2 (eq 11) using this methodology is in progress.
61. -1 (Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710-2716. Simakov, P. A.; Martinez, F. N.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 1226-1232). For a general discussion on the preexponential factor, see: Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
62. -1 (Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710-2716. Simakov, P. A.; Martinez, F. N.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 1226-1232). For a general discussion on the preexponential factor, see: Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
63. -1 (Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710-2716. Simakov, P. A.; Martinez, F. N.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 1226-1232). For a general discussion on the preexponential factor, see: Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
64. -1 (Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710-2716. Simakov, P. A.; Martinez, F. N.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 1226-1232). For a general discussion on the preexponential factor, see: Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
65. Liposomes a practical approach; New, R. R. C., Ed.; IRL Press: Oxford, 1990.
66. •H.
67. •H atoms reacted with 2-propanol (eqs 4 and 5).
68. 2] ≅ 0.04 mM.
69. -1. Under our experimental conditions this reaction is considered to be unimportant. For a recent review, see: Wardman, P. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; pp 289-309.
70. Deems, R. A.; Dennis, E. A. Methods Enzymol. 1981, 71, 703-711.
71. For reviews on sulfuranyl radicals, see: (a) Chatgilialoglu, C. In The Chemistry of Sulphenic Acids and their Derivatives; Patai, S., Ed.; Wiley: Chichester, 1990; pp 549-569. (b) Margaretha, P. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; pp 277-288.
72. For reviews on sulfuranyl radicals, see: (a) Chatgilialoglu, C. In The Chemistry of Sulphenic Acids and their Derivatives; Patai, S., Ed.; Wiley: Chichester, 1990; pp 549-569. (b) Margaretha, P. In S-Centered Radicals; Alfassi, Z. B., Ed.; Wiley: Chichester, 1999; pp 277-288.
73. Rationalizations similar to those in ref 48 are valid also for compounds 7-9 and 11-13.
74. The effect of ionizing radiations on sulfur-containing molecules of biological interest has been investigated for the last half-century. The following selection of references is of interest to this work: Jayson, G. G.; Stirling, D. A.; Shallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156. Lal, M. Can. J. Chem. 1976, 54, 1092-1097. Lal, M. Radiat. Phys. Chem. 1982, 19, 427-434. Sjöberg, L.; Eriksen, T. E.; Revész, L. Radiat. Res. 1982, 89, 255-261. Hiller, K.-O.; Masloch, B.; Gobl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010-12015. Goez, M.; Rozwadowski, J.; Marciniak, B. J. Am. Chem. Soc. 1996, 118, 2882-2891.
75. The effect of ionizing radiations on sulfur-containing molecules of biological interest has been investigated for the last half-century. The following selection of references is of interest to this work: Jayson, G. G.; Stirling, D. A.; Shallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156. Lal, M. Can. J. Chem. 1976, 54, 1092-1097. Lal, M. Radiat. Phys. Chem. 1982, 19, 427-434. Sjöberg, L.; Eriksen, T. E.; Revész, L. Radiat. Res. 1982, 89, 255-261. Hiller, K.-O.; Masloch, B.; Gobl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010-12015. Goez, M.; Rozwadowski, J.; Marciniak, B. J. Am. Chem. Soc. 1996, 118, 2882-2891.
76. The effect of ionizing radiations on sulfur-containing molecules of biological interest has been investigated for the last half-century. The following selection of references is of interest to this work: Jayson, G. G.; Stirling, D. A.; Shallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156. Lal, M. Can. J. Chem. 1976, 54, 1092-1097. Lal, M. Radiat. Phys. Chem. 1982, 19, 427-434. Sjöberg, L.; Eriksen, T. E.; Revész, L. Radiat. Res. 1982, 89, 255-261. Hiller, K.-O.; Masloch, B.; Gobl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010-12015. Goez, M.; Rozwadowski, J.; Marciniak, B. J. Am. Chem. Soc. 1996, 118, 2882-2891.
77. The effect of ionizing radiations on sulfur-containing molecules of biological interest has been investigated for the last half-century. The following selection of references is of interest to this work: Jayson, G. G.; Stirling, D. A.; Shallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156. Lal, M. Can. J. Chem. 1976, 54, 1092-1097. Lal, M. Radiat. Phys. Chem. 1982, 19, 427-434. Sjöberg, L.; Eriksen, T. E.; Revész, L. Radiat. Res. 1982, 89, 255-261. Hiller, K.-O.; Masloch, B.; Gobl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010-12015. Goez, M.; Rozwadowski, J.; Marciniak, B. J. Am. Chem. Soc. 1996, 118, 2882-2891.
78. The effect of ionizing radiations on sulfur-containing molecules of biological interest has been investigated for the last half-century. The following selection of references is of interest to this work: Jayson, G. G.; Stirling, D. A.; Shallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156. Lal, M. Can. J. Chem. 1976, 54, 1092-1097. Lal, M. Radiat. Phys. Chem. 1982, 19, 427-434. Sjöberg, L.; Eriksen, T. E.; Revész, L. Radiat. Res. 1982, 89, 255-261. Hiller, K.-O.; Masloch, B.; Gobl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010-12015. Goez, M.; Rozwadowski, J.; Marciniak, B. J. Am. Chem. Soc. 1996, 118, 2882-2891.
79. The effect of ionizing radiations on sulfur-containing molecules of biological interest has been investigated for the last half-century. The following selection of references is of interest to this work: Jayson, G. G.; Stirling, D. A.; Shallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156. Lal, M. Can. J. Chem. 1976, 54, 1092-1097. Lal, M. Radiat. Phys. Chem. 1982, 19, 427-434. Sjöberg, L.; Eriksen, T. E.; Revész, L. Radiat. Res. 1982, 89, 255-261. Hiller, K.-O.; Masloch, B.; Gobl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010-12015. Goez, M.; Rozwadowski, J.; Marciniak, B. J. Am. Chem. Soc. 1996, 118, 2882-2891.
80. The effect of ionizing radiations on sulfur-containing molecules of biological interest has been investigated for the last half-century. The following selection of references is of interest to this work: Jayson, G. G.; Stirling, D. A.; Shallow, A. J. Int. J. Radiat. Biol. 1971, 19, 143-156. Lal, M. Can. J. Chem. 1976, 54, 1092-1097. Lal, M. Radiat. Phys. Chem. 1982, 19, 427-434. Sjöberg, L.; Eriksen, T. E.; Revész, L. Radiat. Res. 1982, 89, 255-261. Hiller, K.-O.; Masloch, B.; Gobl, M.; Asmus, K.-D. J. Am. Chem. Soc. 1981, 103, 2734-2743. Zhao, R.; Lind, J.; Merényi, G.; Eriksen, T. E. J. Am. Chem. Soc. 1994, 116, 12010-12015. Goez, M.; Rozwadowski, J.; Marciniak, B. J. Am. Chem. Soc. 1996, 118, 2882-2891.
81. Rauk, A.; Yu, D.; Armostrong, D. A. J. Am. Chem. Soc. 1998, 120, 8848-8855 and references therein.
82. 3.
83. Collin, G. J.; Perrin, P. M. Garneau, F. X. Can. J. Chem. 1974, 52, 2337-2340.
84. (a) TMA-DPH = 1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatriene p-toluenesulfonate.
85. (b) Andrich, M. P.; Vanderkooi, J. M. Biochemistry 1976, 15, 1257-1261.
86. It is known that liposomes composed from phospholipids with saturated hydrocarbon chains yielded, for example, longer blood circulation, maintaining high biocompatibility. For a review, see: Lasic, D. D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1685-1698.
87. 61
88. Nakazawa, T.; Nagatsuka, S. Int. J. Radiat. Biol. 1980, 38, 537-544.
89. Stark, G. Biochim. Biophys. Acta 1991, 1071, 103-122 and references therein.
90. Konings, A. W. T.; Damen, J.; Trieling, W. B. Int. J. Radiat. Biol. 1979, 35, 343-350.
91. Ferreri, C.; Costantino, C.; Perrotta, L.; Mulazzani, Q. G.; Landi, L., Chatgilialoglu, C. Manuscript in preparation.
92. Trost, B. M.; Ziman, S. D. J. Org. Chem. 1973, 38, 932-936.
93. Salerni, O. L.; Clark, R. N.; Smart, B. E. J. Chem. Soc. C 1966, 645-648.
94. It is worth noting that, under these conditions, it was also possible to separate the positional isomers of octadecenoic acid methyl esters and it was found that only Δ9 isomers are present in the reaction.
95. Reference 29, p 100.
96. The average diameter of the unilamellar vesicles was found to be ca. 90 nm; see: Fiorentini, D.; Cipollone, M.; Pugnaloni, A.; Biagini, G.; Landi, L. Free Radical Res. 1994, 21, 329-339.