Synthesis of analogues of ochratoxin A

Natural Product Research

Volumn 26, Issue 19, 2012, Pages 1799-1805

  Plastina, Pierluigi ^a   Fazio, Alessia ^a   Attya, Mohamed ^a   Sindona, Giovanni ^a   Gabriele, Bartolo ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

diastereomeric analogues; ochratoxin A; ochratoxin analogues; OTA; synthesis

Indexed keywords

ALANINE DERIVATIVE; FUNCTIONAL GROUP; LEUCINE; OCHRATOXIN; SERINE DERIVATIVE; TRYPTOPHAN DERIVATIVE;

ARTICLE; DIASTEREOISOMER; POLYMERIZATION; PURIFICATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALANINE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OCHRATOXINS; SERINE; TRIAZOLES;

EID: 84866553894     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2011.613385     Document Type: Article

References (52)

1. Anli, E., & Bayram, M. (2009). Ochratoxin A in wines. Food Reviews International, 25, 214-232.
2. Bunge, I., Dirheimer, G., & Röschenthaler, R. (1978). In vivo and in vitro inhibition of protein synthesis in Bacillus stearothermophilus by ochratoxin A. Biochemical and Biophysical Research Communications, 83, 398-405. (Pubitemid 8391839)
3. Clark, H.A., & Snedeker, S.M. (2006). Ochratoxin A: Its cancer risk and potential for exposure. Journal of Toxicology and Environmental Health. Part B, Critical Reviews, 9, 265-296.
4. Cramer, B., Harrer, H., Nakamura, K., Uemura, D., & Humpf, H.-U. (2010). Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers. Bioorganic & Medicinal Chemistry, 18, 343-347.
5. Cramer, B., Koenigs, M., & Humpf, H.-U. (2008). Identification and in vitro cytotoxicity of ochratoxin A degradation products formed during coffee roasting. Journal of Agricultural and Food Chemistry, 56, 5673-5681.
6. Creppy, E.E., Kern, D., Steyn, P.S., Vleggaar, R., Röschenthaler, R., & Dirheimer, G. (1983). Comparative study of the effect of ochratoxin A analogues on yeast aminoacyl-tRNA synthetases and on the growth and protein synthesis of hepatoma cells. Toxicology Letters, 19, 217-224. (Pubitemid 14208518)
7. Creppy, E.E., Lugnier, A.A.J., Fasiolo, F., Heller, K., Röschenthaler, R., & Dirheimer, G. (1979). In vitro inhibition of yeast phenylalanyl-tRNA synthetase by ochratoxin A. Chemico-Biological Interactions, 24, 257-261. (Pubitemid 9139457)
8. Duarte, S.C., Pena, A., & Lino, C.M. (2010). A Review on Ochratoxin A Occurrence and effects of processing of cereal and cereal derived food products. Food Microbiology, 27, 187-198.
9. El Khoury, A., & Atoui, A. (2010). Ochratoxin A: General overview and actual molecular status. Toxins, 4, 461-493.
10. Gabriele, B., Attya, M., Fazio, A., Di Donna, L., Plastina, P., & Sindona, G. (2009). A new and expedient total synthesis of ochratoxin A and d5-ochratoxin A. Synthesis, 11, 1815-1820.
11. Hadidane, R., Bacha, H., Creppy, E.E., Hammami, M., Ellouze, F., & Dirheimer, G. (1992). Isolation and structure determination of natural analogs of the mycotoxin ochratoxin A produced by aspergillusochraceus. Toxicology, 76, 233-243. (Pubitemid 23011044)
12. Hoehler, D., Marquardt, R.R., McIntosh, A.R., & Hatch, G.M. (1997). Induction of free radicals in hepatocytes, mitochondria and microsomes of rats by ochratoxin A and its analogs. Biochimica et Biophysica Acta, 1357, 225-233. (Pubitemid 27278046)
13. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans (1993). Ochratoxin, A. in some naturally occurring substances: Food items and constituents, heterocyclic aromatic amines and mycotoxins, IARC and WHO: Lyon, 56, 489-521.
14. Jalili, M., Jinap, S., & Radu, S. (2010). Natural occurrence of ochratoxin A contamination in commercial black and white pepper products. Mycopathologia, 170, 251-258.
15. Mally, A., Pepe, G., Ravoori, S., Fiore, M., Gupta, R.C., Dekant, W., & Mosesso, P. (2005). Ochratoxin A causes DNA damage and cytogenetic effects but no DNA adducts in rats. Chemical Research in Toxicology, 18, 1253-1261. (Pubitemid 41170249)
16. Mally, A., Zepnik, H., Wanek, P., Eder, E., Dingley, K., Ihmels, H., . . ., Dekant, W. (2004). Ochratoxin A: Lack of formation of covalent DNA adducts. Chemical Research in Toxicology, 17, 234-242. (Pubitemid 38252503)
17. McMasters, D.R., & Vedani, A. (1999). Ochratoxin binding to phenylalanyl-tRNA synthetase: Computational approach to the mechanism of ochratoxicosis and its antagonism. Journal of Medicinal Chemistry, 42, 3075-3086. (Pubitemid 29384042)
18. Müller, G., Burkert, B., Möller, U., Diller, R., Rohrmann, B., Rosner, H., & Köhler, H. (2004). Ochratoxin A and some of its derivatives modulate radical formation of porcine blood monocytes and granulocytes. Toxicology, 199, 251-259. (Pubitemid 38624535)
19. O'Brien, E., & Dietrich, D.R. (2005). Ochratoxin A: The continuing enigma. Critical Reviews in Toxicology, 35, 33-60. (Pubitemid 40179900)
20. Pfohl-Leszkowicz, A., & Manderville, R.A. (2007). Ochratoxin A: An overview on toxicity and carcinogenicity in animals and humans. Molecular Nutrition & Food Research, 51, 61-39.
21. Reddy, K.R.N., Salleh, B., Saad, B., Abbas, H.K., Abel, C.A., & Shier, W.T. (2010). An overview of mycotoxin contamination in foods and its implications for human health. Toxin Reviews, 29, 3-26.
22. Roth, A., Eriani, G., Dirheimer, G., & Gangloff, J. (1993). Kinetic properties of pure overproduced Bacillus subtilis phenylalanyl-tRNA synthetase do not favor its in vivo inhibition by Ochratoxin A. FEBS Letters, 326, 87-91. (Pubitemid 23200253)
23. Steyn, P.S., Vleggaar, R., Du Preez, N.P., Blyth, A.A., & Seegers, J.C. (1975). The in vitro toxicity of analogs of ochratoxin A in monkey epithelial cells. Toxicology and Applied Pharmacology, 32, 198-203.
24. Van der Merwe, K.J., Steyn, P.S., Fourie, L., Scott, D.B., & Theron, J.J. (1965). Ochratoxin A, a toxic metabolite produced by aspergillus ochraceus wilh. Nature, 205, 1112-1113.
25. Xiao, H., Madhyastha, S., Marquardt, R.R., Li, S.Z., Vodela, J.K., Frohlich, A.A., & Kemppainen, B.W. (1996). Toxicity of ochratoxin A, its opened lactone form and several of its analogs: Structure-activity relationships. Toxicology and Applied Pharmacology, 137, 182-192. (Pubitemid 26130136)
26. Xiao, H., Marquardt, R.R., Frohlich, A.A., & Ling, Y.Z. (1995). Synthesis and structural elucidation of analogs of ochratoxin A. Journal of Agricultural and Food Chemistry, 43, 524-530.
27. Anli, E, and, Bayram, M. 2009. Ochratoxin A in wines. Food Reviews International, 25: 214-232.
28. Bunge, I, Dirheimer, G, and, Rschenthaler, R. 1978. Invivo and invitro inhibition of protein synthesis in Bacillus stearothermophilus by ochratoxin A. Biochemical and Biophysical Research Communications, 83: 398-405. (Pubitemid 8391839)
29. Clark, HA, and, Snedeker, SM. 2006. Ochratoxin A: its cancer risk and potential for exposure. Journal of Toxicology and Environmental Health. Part B, Critical Reviews, 9: 265-296.
30. Cramer, B, Harrer, H, Nakamura, K, Uemura, D, and, Humpf, H-U. 2010. Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers. Bioorganic & Medicinal Chemistry, 18: 343-347.
31. Cramer, B, Koenigs, M, and, Humpf, H-U. 2008. Identification and invitro cytotoxicity of ochratoxin A degradation products formed during coffee roasting. Journal of Agricultural and Food Chemistry, 56: 5673-5681.
32. Creppy, EE, Kern, D, Steyn, PS, Vleggaar, R, Rschenthaler, R, and, Dirheimer, G. 1983. Comparative study of the effect of ochratoxin A analogues on yeast aminoacyl-tRNA synthetases and on the growth and protein synthesis of hepatoma cells. Toxicology Letters, 19: 217-224. (Pubitemid 14208518)
33. Creppy, EE, Lugnier, AAJ, Fasiolo, F, Heller, K, Rschenthaler, R, and, Dirheimer, G. 1979. Invitro inhibition of yeast phenylalanyl-tRNA synthetase by ochratoxin A. Chemico-Biological Interactions, 24: 257-261. (Pubitemid 9139457)
34. Duarte, SC, Pena, A, and, Lino, CM. 2010. A Review on Ochratoxin A Occurrence and effects of processing of cereal and cereal derived food products. Food Microbiology, 27: 187-198.
35. el Khoury, A, and, Atoui, A. 2010. Ochratoxin A: general overview and actual molecular status. Toxins, 4: 461-493.
36. 5-ochratoxin A. Synthesis, 11: 1815-1820.
37. Hadidane, R, Bacha, H, Creppy, EE, Hammami, M, Ellouze, F, and, Dirheimer, G. 1992. Isolation and structure determination of natural analogs of the mycotoxin ochratoxin A produced by aspergillus-ochraceus. Toxicology, 76: 233-243. (Pubitemid 23011044)
38. Hoehler, D, Marquardt, RR, McIntosh, AR, and, Hatch, GM. 1997. Induction of free radicals in hepatocytes, mitochondria and microsomes of rats by ochratoxin A and its analogs. Biochimica et Biophysica Acta, 1357: 225-233. (Pubitemid 27278046)
39. IARC Monographs on the Evaluation. of Carcinogenic Risks to Humans (1993). Ochratoxin, A. in some naturally occurring substances: food items and constituents, heterocyclic aromatic amines and mycotoxins, IARC and WHO: Lyon, 56, 489-521
40. Jalili, M, Jinap, S, and, Radu, S. 2010. Natural occurrence of ochratoxin A contamination in commercial black and white pepper products. Mycopathologia, 170: 251-258.
41. Mally, A, Pepe, G, Ravoori, S, Fiore, M, Gupta, RC, Dekant, W, and, Mosesso, P. 2005. Ochratoxin A causes DNA damage and cytogenetic effects but no DNA adducts in rats. Chemical Research in Toxicology, 18: 1253-1261. (Pubitemid 41170249)
42. Mally, A, Zepnik, H, Wanek, P, Eder, E, Dingley, K, Ihmels, H, Dekant, W. 2004. Ochratoxin A: lack of formation of covalent DNA adducts. Chemical Research in Toxicology, 17: 234-242. (Pubitemid 38252503)
43. McMasters, DR, and, Vedani, A. 1999. Ochratoxin binding to phenylalanyl-tRNA synthetase: Computational approach to the mechanism of ochratoxicosis and its antagonism. Journal of Medicinal Chemistry, 42: 3075-3086. (Pubitemid 29384042)
44. Mller, G, Burkert, B, Mller, U, Diller, R, Rohrmann, B, Rosner, H, and, Khler, H. 2004. Ochratoxin A and some of its derivatives modulate radical formation of porcine blood monocytes and granulocytes. Toxicology, 199: 251-259. (Pubitemid 38624535)
45. OBrien, E, and, Dietrich, DR. 2005. Ochratoxin A: the continuing enigma. Critical Reviews in Toxicology, 35: 33-60. (Pubitemid 40179900)
46. Pfohl-Leszkowicz, A, and, Manderville, RA. 2007. Ochratoxin A: an overview on toxicity and carcinogenicity in animals and humans. Molecular Nutrition & Food Research, 51: 61-39.
47. Reddy, KRN, Salleh, B, Saad, B, Abbas, HK, Abel, CA, and, Shier, WT. 2010. An overview of mycotoxin contamination in foods and its implications for human health. Toxin Reviews, 29: 3-26.
48. Roth, A, Eriani, G, Dirheimer, G, and, Gangloff, J. 1993. Kinetic properties of pure overproduced Bacillus subtilis phenylalanyl-tRNA synthetase do not favor its invivo inhibition by Ochratoxin A. FEBS Letters, 326: 87-91. (Pubitemid 23200253)
49. Steyn, PS, Vleggaar, R, Du Preez, NP, Blyth, AA, and, Seegers, JC. 1975. The invitro toxicity of analogs of ochratoxin A in monkey epithelial cells. Toxicology and Applied Pharmacology, 32: 198-203.
50. Van der Merwe, KJ, Steyn, PS, Fourie, L, Scott, DB, and, Theron, JJ. 1965. Ochratoxin A, a toxic metabolite produced by aspergillus ochraceus wilh. Nature, 205: 1112-1113.
51. Xiao, H, Madhyastha, S, Marquardt, RR, Li, SZ, Vodela, JK, Frohlich, AA, and, Kemppainen, BW. 1996. Toxicity of ochratoxin A, its opened lactone form and several of its analogs: structure-activity relationships. Toxicology and Applied Pharmacology, 137: 182-192. (Pubitemid 26130136)
52. Xiao, H, Marquardt, RR, Frohlich, AA, and, Ling, YZ. 1995. Synthesis and structural elucidation of analogs of ochratoxin A. Journal of Agricultural and Food Chemistry, 43: 524-530.