Recent approaches to the total synthesis of phytoprostanes, isoprostanes and neuroprostanes as important products of lipid oxidative stress and biomarkers of disease

Chemicke Listy

Volumn 108, Issue 4, 2014, Pages 301-319

  Jahn, Emanuela ^a   Durand, Thierry ^b   Galano, Jean Marie ^b   Jahn, Ullrich ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUT CHARLES GERHARDT   (France)

Author keywords

Isoprostanes; Lipids; Neuroprostanes; Oxidative stress; Phytoprostanes; Total synthesis

Indexed keywords

EID: 84899717583     PISSN: 00092770     EISSN: 12137103     Source Type: Journal    
DOI: None     Document Type: Article

References (70)

1. Oxidative Stress in Vertebrates and Invertebrates: Molecular Aspects of Cell Signaling(Farooqui T., Farooqui A. A., eds.), Wiley-Blackwell, Hoboken 2012.
2. Oxidative Stress: Diagnostics, Prevention, And Therapy(Andreescu S., Hepel M., eds.), ACS Symposium Series, Vol. 1083 ACS Washington, DC 2011.
3. Polyunsaturated Fatty Acids: Sources, Antioxidant Properties and Health Benefits(Catalá A., ed.), Nova Science Publishers, Hauppauge, NY 2013.
4. Lipid Peroxidation(Catalá A., ed.), InTech, Rijeka 2012.
5. Jahn U., Galano J.-M., Durand T.: Angew. Chem. Int. Ed. 47, 5894 (2008).
6. Yin H., Xu L., Porter N. A.: Chem. Rev. 111, 5944 (2011).
7. Porter N. A.: J. Org. Chem. 78, 3511 (2013).
8. Prostaglandins: Biochemistry, Functions, Types and Roles(Goodwin G. M., ed.), Nova Science Publishers, Hauppauge, NY 2010.
9. Das S., Chandrasekhar S., Yadav J. S., Gree R.: Chem. Rev. 107, 3286 (2007).
10. Prostaglandins, Leukotrienes and Essential Fatty Acids(Horrobin D. F., Manku M. S., Sirois P., Borgeat P., eds.), Churchill Livingstone, Edinburgh 2002.
11. Marks F., Fürstenberger G.: Prostaglandins, Leukotrienes, and Other Eicosanoids, Wiley-VCH, Weinheim 1999.
12. Milne G. L., Yin H., Hardy K. D., Davies S. S., Roberts II L. J.: Chem. Rev. 111, 5973 (2011).
13. Jahn U., Galano J.-M., Durand T.: Prostaglandins Leukotrienes Essent. Fatty Acids 82, 83 (2010).
14. Galano J.-M., Mas E., Barden A., Mori T. A., Signorini C., De Felice C., Barrett A., Opere C., Pinot E., Schwedhelm E., Benndorf R., Roy J., Le Guennec J.-Y., Oger C., Durand T.: Prostaglandins Other Lipid Mediators 107, 95 (2013).
15. Higdon A., Diers A. R., Oh J. Y., Landar A., Darley-Usmar V. M.: Biochem. J. 442, 453 (2012).
16. Biomarkers For Antioxidant Defense And Oxidative Damage: Principles And Practical Applications(Aldini G., Yeum K.-J., Niki E., Russell R. M., eds.), Blackwell, Ames 2010.
17. El Fangour S., Guy A., Vidal J.-P., Rossi J.-C., Durand T.: J. Org. Chem. 70, 989 (2005).
18. Pinot E., Guy A., Guyon A.-L., Rossi J.-C., Durand T.: Tetrahedron: Asymmetry 16, 1893 (2005).
19. Pinot E., Guy A., Fournial A., Balas L., Rossi J.-C., Durand T.: J. Org. Chem. 73, 3063 (2008).
20. Mueller M. J.: Prostaglandins, Leukotrienes Essent. Fatty Acids 82, 71 (2010).
21. Auvinet A.-L., Eignerová B., Guy A., Kotora M., Durand T.: Tetrahedron Lett. 50, 1498 (2009).
22. Noyori R., Tomino I., Tanimoto Y., Nishizawa M.: J. Am. Chem. Soc. 106, 6709 (1984).
23. Perlikowska W., Mikołajczyk M.: Synthesis 2009, 2715.
24. Mikołajczyk M., Perlikowska W.: Synthesis 2007, 1225.
25. Perlikowska W., Mikołajczyk M.: Tetrahedron: Asymmetry 22, 1767 (2011).
26. Miura A., Kuwahara S.: Tetrahedron 65, 3364 (2009).
27. Vázquez-Romero A., Cárdenas L., Blasi E., Verdaguer X., Riera A.: Org. Lett. 11, 3104 (2009).
28. Vázquez-Romero A., Verdaguer X., Riera A.: Eur. J. Org. Chem. 2013, 1716.
29. Iqbal M., Evans P., Lledó A., Verdaguer X., Pericàs M. A., Riera A., Loeffler C., Sinha A. K., Mueller M. J.: ChemBioChem 6, 276 (2005).
30. Robert F., Milet A., Gimbert Y., Konya D., Greene A. E.: J. Am. Chem. Soc. 123, 5396 (2001).
31. Oger C., Brinkmann Y., Bouazzaoui S., Durand T., Galano J.-M.: Org. Lett. 10, 5087 (2008).
32. Oger C., Bultel-Poncé V., Guy A., Durand T., Galano J.-M.: Eur. J. Org. Chem. 2012, 2621.
33. Suzuki T., Morita K., Tsuchida M., Hiroi K.: Org. Lett. 4, 2361 (2002).
34. Oger C., Marton Z., Brinkmann Y., Bultel-Poncé V., Durand T., Graber M., Galano J.-M.: J. Org. Chem. 75, 1892 (2010).
35. Brinkmann Y., Oger C., Guy A., Durand T., Galano J.-M.: J. Org. Chem. 75, 2411 (2010).
36. De Felice C.; Signorini C., Durand T., Oger C., Guy A., Bultel-Poncé V., Galano J.-M., Ciccoli L., Leoncini S., D'Esposito M., Filosa S., Pecorelli A., Valacchi G., Hayek J.: J. Lipid Res. 52, 2287 (2011).
37. Elsner P., Jetter P., Brödner K., Helmchen G.: Eur. J. Org. Chem. 2008, 2551.
38. Helmchen G., Goeke A., Lauer G., Urmann M., Fries J.: Angew. Chem. Int. Ed. 29, 1024 (1990).
39. Bindra J. S., Grodski A., Schaaf T. K., Corey E. J.: J. Am. Chem. Soc. 95, 7522 (1973).
40. Veselý I., Kozmík V., Dědek V., Paleček J., Mostecký J., Stibor I.: Collect. Czech. Chem. Commun. 54, 1683 (1989).
41. Blanchette M. A., Choy W., Davis J. T., Essenfeld A. P., Masamune S., Roush W. R., Sakai T.: Tetrahedron Lett. 25, 2183 (1984).
42. Jahn U., Dinca E.: Chem. Eur. J. 15, 58 (2009).
43. Jahn U., Dinca E.: J. Org. Chem. 75, 4480 (2010).
44. Muzart J.: Synthesis 1993, 11.
45. Chang C.-T., Patel P., Kang N., Lawson J. A., Song W.-L., Powell W. S., FitzGerald G. A., Rokach J.: Bioorg. Med. Chem. Lett. 18, 5523 (2008).
46. Lawson J. A., Kim S., Powell W. S., FitzGerald G. A., Rokach J.: J. Lipid Res. 47, 2515 (2006).
47. Hwang S. W., Adiyaman M., Khanapure S., Schio L., Rokach J.: J. Am. Chem. Soc. 116, 10829 (1994).
48. Patel P., Chang C.-T., Kang N., Lee G.-J., Powell W. S., Rokach J.: Tetrahedron Lett. 48, 5289 (2007).
49. Chang C.-T., Patel P., Gore V., Song W.-L., Lawson J. A., Powell W. S., FitzGerald G. A., Rokach J.: Bioorg. Med. Chem. Lett. 19, 6755 (2009).
50. Kim S., Lawson J. A., Praticò D., FitzGerald G. A., Rokach J.: Tetrahedron Lett. 43, 2801 (2002).
51. Pandya B. A., Snapper M. L.: J. Org. Chem. 73, 3754 (2008).
52. Schrader T. O., Snapper M. L.: Tetrahedron Lett. 41, 9685 (2000).
53. Schrader T. O., Snapper M. L.: J. Am. Chem. Soc. 124, 10998 (2002).
54. Shizuka M., Snapper M. L.: Synthesis 2007, 2397.
55. Shizuka M., Schrader T. O., Snapper M. L.: J. Org. Chem. 71, 1330 (2006).
56. Jung M. E., Berliner J. A., Angst D., Yue D., Koroniak L., Watson A. D., Li R.: Org. Lett. 7, 3933 (2005).
57. Jung M. E., Berliner J. A., Koroniak L., Gugiu B. G., Watson A. D.: Org. Lett. 10, 4207 (2008).
58. Jung M. E., Kers A., Subbanagounder G., Berliner J. A.: Chem. Commun. 2003, 196.
59. Acharya H. P., Miyoshi K., Takashima Y., Ogawa N., Kobayashi Y.: Heterocycles 76, 1181 (2008).
60. Acharya H. P., Miyoshi K., Kobayashi Y.: Org. Lett. 9, 3535 (2007).
61. Egger J., Bretscher P., Freigang S., Kopf M., Carreira E. M.: Angew. Chem. Int. Ed. 52, 5382 (2013).
62. Zhu C., Shen X., Nelson S. G.: J. Am. Chem. Soc. 126, 5352 (2004).
63. Acharya H. P., Kobayashi Y.: Angew. Chem. Int. Ed. 44, 3481 (2005).
64. Oger C., Bultel-Poncé V., Guy A., Balas L., Rossi J.-C., Durand T., Galano J.-M.: Chem. Eur. J. 16, 13976 (2010).
65. Paterson I., Yeung K.-S., Smaill J. B.: Synlett 1993, 774.
66. Brown C. A., Ahuja V. K.: J. Chem. Soc., Chem. Commun. 1973, 553.
67. Oger C., Balas L., Durand T., Galano J.-M.: Chem. Rev. 113, 1313 (2013).
68. Le Guennec J.-Y., Galano J.-M., Oger C., Thireau J., Roy J., Bultel-Poncé V., Guy A., Durand T.: Methods and pharmaceutical composition for the treatment and prevention of cardiac arrhythmias.5-EP12306519.3, December 2012.
69. Taber D. F., Reddy P. G., Arneson K. O.: J. Org. Chem. 73, 3467 (2008).
70. Sarkar T. K., Ghorai B. K., Nandy S. K., Mukherjee B., Banerji A.: J. Org. Chem. 62, 6006 (1997).