Skip to main content
Log in

Progress in the Chemistry of Amino-Acid Derivatives of Isocoumarins and 3,4-Dihydroisocoumarins

  • Published:
Chemistry of Natural Compounds Aims and scope

Approaches to the synthesis of isocoumarins and 3,4-dihydroisocoumarins containing natural or synthetic amino-acid fragments are reviewed. Most attention is paid to the two most numerous groups of natural 3,4-dihydroisocoumarins, i.e., ochratoxins and amicoumacins.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R. D. Barry, Chem. Rev., 64 (3), 229 (1964).

    Article  CAS  Google Scholar 

  2. R. A. Hill, Prog. Chem. Org. Nat. Prod., 49, 1 (1986).

    CAS  Google Scholar 

  3. R. P. Singh and J. N. Srivastava, J. Indian Counc. Chem., 12 (1), 23 (1996).

    CAS  Google Scholar 

  4. E. Napolitano, Org. Prep. Proced. Int., 29, 631 (1997).

    Article  CAS  Google Scholar 

  5. S. V. Shilin, O. V. Shablykina, V. V. Ishchenko, and V. P. Khilya, Chem. Nat. Compd., 50, 638 (2014).

    Article  CAS  Google Scholar 

  6. S. V. Shilin, O. V. Shablikina, V. V. Ishchenko, and V. P. Khilya, Dopov. Nats. Akad. Nauk Ukr., No. 3, 141 (2009).

  7. Z.-H. Jiang, X.-Y. Wen, T. Tanaka, S.-Y. Wu, Z. Liu, H. Iwata, Y. Hirose, S. Wu, and I. Kouno, J. Nat. Prod., 71 (4), 719 (2008).

    Article  CAS  PubMed  Google Scholar 

  8. J. Alfaro, S. Belmar, et al., US Pat. Appl. 20190185451, Jun. 20, 2019.

  9. N. Matsumoto, T. Nakashima, K. Isshiki, H. Kuboki, S. Hirano, H. Kumagai, T. Yoshioka, M. Ishizuka, and T. Takeuchi, J. Antibiot., 54 (3), 285 (2001).

    Article  CAS  Google Scholar 

  10. C. Darsih, V. Prachyawarakorn, S. Wiyakrutta, C. Mahidol, S. Ruchirawat, and P. Kittakoop, RSC Adv., 5 (86), 70595 (2015).

    Article  CAS  Google Scholar 

  11. M. A. Khaimova, I. A. Atanasova, and A. I. Nakov, Chem. Heterocycl. Compd., 20 (3), 256 (1984).

    Article  Google Scholar 

  12. F. Sakamoto, S. Ikeda, and G. Tsukamoto, Chem. Pharm. Bull., 31 (8), 2698 (1983).

    Article  CAS  Google Scholar 

  13. M.-J. Luo, M. Hu, R.-J. Song, D.-L. He, and J.-H. Li, Chem. Commun., 55 (8), 1124 (2019).

    Article  CAS  Google Scholar 

  14. M.-J. Luo, T.-T. Zhang, F.-J. Cai, J.-H. Li, and D.-L. He, Chem. Commun., 55 (50), 7251 (2019).

    Article  CAS  Google Scholar 

  15. H. Natsugari, H. Tawada, and H. Ikeda, US Pat. 5,198,462, Mar. 30, 1993.

  16. S. Ponra, A. Nyadanu, S. Maurin, L. El Kaim, L. Grimaud, and M. R. Vitale, Synthesis, 50 (6), 1331 (2018).

    Article  CAS  Google Scholar 

  17. E. Soleimani and M. Zainali, J. Org. Chem., 76 (24), 10306 (2011).

    Article  CAS  PubMed  Google Scholar 

  18. E. Soleimani, M. Zainali, N. Ghasemi, and B. Notash, Tetrahedron, 69 (46), 9832 (2013).

    Article  CAS  Google Scholar 

  19. E. B. Knott, J. Chem. Soc., 402 (1963).

  20. E. B. Knott, J. Chem. Soc., 6204 (1964).

  21. C. Yan, Y. Yu, B. Peng, and X. Huang, Eur. J. Org. Chem., 2020 (6), 723 (2020).

    Article  CAS  Google Scholar 

  22. M. S. Weerasinghe, S. T. Karlson, Y. Lu, and K. A. Wheeler, Cryst. Growth Des., 16 (4), 1781 (2016).

    Article  CAS  Google Scholar 

  23. M. A. Hernandez, J. C. Powers, J. Glinski, J. Oleksyszyn, J. Vijayalakshmi, and E. F. Meyer, Jr., J. Med. Chem., 35 (6), 1121 (1992).

    Article  CAS  PubMed  Google Scholar 

  24. K. J. van der Merwe, P. S. Steyn, L. Fourie, De B. Scott, and J. J. Theron, Nature, 205 (4976), 1112 (1965).

    Article  PubMed  Google Scholar 

  25. M. D. Northolt, H. P. van Egmond, and W. E. Paulsch, J. Food Prot., 42, 485 (1979).

    Article  CAS  PubMed  Google Scholar 

  26. R. R. Marquardt and A. A. Frohlich, J. Anim. Sci., 70, 3968 (1992).

    Article  CAS  PubMed  Google Scholar 

  27. IARC, IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, 56, 489 (1993).

  28. A. Belmadani, G. Tramu, A. M. Betbeder, P. S. Steyn, and E. E. Creppy, Arch. Toxicol., 72 (10), 656 (1998).

    Article  CAS  PubMed  Google Scholar 

  29. P. S. Steyn and C. W. Holzapfel, Tetrahedron, 23, 4449 (1967).

    Article  CAS  PubMed  Google Scholar 

  30. K. J. van der Merwe, P. S. Steyn, and L. Fourie, J. Chem. Soc., 7083 (1965).

  31. J. C. Roberts and P. Woollven, J. Chem. Soc. C, 278 (1970).

  32. A. Bouisseau, A. Roland, F. Reillon, R. Schneider, and F. Cavelier, Org. Lett., 15 (15), 3888 (2013).

    Article  CAS  PubMed  Google Scholar 

  33. P. Plastina, A. Fazio, M. Attya, G. Sindona, and B. Gabriele, Nat. Prod. Res., 26 (19), 1799 (2012).

    Article  CAS  PubMed  Google Scholar 

  34. B. Gabriele, M. Attya, A. Fazio, L. Di Donna, P. Plastina, and G. Sindona, Synthesis, 2009 (11), 1815 (2009).

    Article  CAS  Google Scholar 

  35. B. Cramer, H. Harrer, K. Nakamura, D. Uemura, and H.-U. Humpf, Bioorg. Med. Chem., 18 (1), 343 (2010).

    Article  CAS  PubMed  Google Scholar 

  36. W. Li, M. P. Wiesenfeldt, and F. Glorius, J. Am. Chem. Soc., 139 (7), 2585 (2017).

    Article  CAS  PubMed  Google Scholar 

  37. H. Xiao, R. R. Marquardt, A. A. Frohlich, and Y. Z. Ling, J. Agric. Food Chem., 43 (2), 524 (1995).

    Article  CAS  Google Scholar 

  38. A. McClay, H. van den Berg, et al., WO 2006/46071, May 4, 2006.

  39. J. A. Ardus, I. G. Gillman, and R. A. Manderville, Can. J. Chem., 76 (6), 907 (1998).

    Article  CAS  Google Scholar 

  40. I. G. Gillman, T. N. Clark, and R. A. Manderville, Chem. Res. Toxicol., 12 (11), 1066 (1999).

    Article  CAS  PubMed  Google Scholar 

  41. R. D. Wei and F. S. Chu, Experientia, 30 (2), 174 (1974).

    Article  CAS  PubMed  Google Scholar 

  42. S. Grabley, M. Gareis, W. Bockers, and J. Thiem, Synthesis, 1992 (11), 1078 (1992).

    Article  Google Scholar 

  43. P. S. Steyn and B. E. Payne, S. Afr. J. Chem., 52 (2–3), 69 (1999).

    CAS  Google Scholar 

  44. S. Li, R. Marquardt, and A. A. Frohlich, Food Chem. Toxicol., 38 (2–3), 141 (2000).

    Article  CAS  PubMed  Google Scholar 

  45. A. Pittet, D. Tornare, A. Huggett, and R. Viani, J. Agric. Food Chem., 44 (11), 3564 (1996).

    Article  CAS  Google Scholar 

  46. B. Cramer, M. Koenigs, and H.-U. Humpf, J. Agric. Food Chem., 56 (14), 5673 (2008).

    Article  CAS  PubMed  Google Scholar 

  47. M. W. Bredenkamp, J. L. M. Dillen, P. H. van Rooyen, and P. S. Steyn, J. Chem. Soc., Perkin Trans. 2, No. 11, 1835 (1989).

    Article  Google Scholar 

  48. I. G. Gillman, J. M. Yezek, and R. A. Manderville, Chem. Commun., 6, 647 (1998).

    Article  Google Scholar 

  49. M. E. Brow, J. Dai, G. Park, M. W. Wright, I. G. Gillman, and R. A. Manderville, Photochem. Photobiol., 76 (6), 649 (2002).

    Article  CAS  PubMed  Google Scholar 

  50. J. Dai, G. Park, M. W. Wright, M. Adams, S. A. Akman, and R. A. Manderville, Chem. Res. Toxicol., 15 (12), 1581 (2002).

    Article  CAS  PubMed  Google Scholar 

  51. K. Hadjeba-Medjdoub, M. Tozlovanu, A. Pfohl-Leszkowicz, C. Frenette, R. J. Paugh, and R. A. Manderville, Chem. Res. Toxicol., 25 (1), 181 (2012).

    Article  CAS  PubMed  Google Scholar 

  52. P. G. Mantle, V. Faucet-Marquis, R. A. Manderville, B. Squillaci, and A. Pfohl-Leszkowicz, Chem. Res. Toxicol., 23 (1), 89 (2010).

    Article  CAS  PubMed  Google Scholar 

  53. A. Bittner, B. Cramer, and H.-U. Humpf, J. Agric. Food Chem., 61 (51), 12737 (2013).

    Article  CAS  PubMed  Google Scholar 

  54. Y. Shen, Z. Shi, J. T. Fan, and B. Yan, Toxicol. Lett., 332, 171 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. Y. Li, Z. Li, K. Yamanaka, Y. Xu, W. Zhang, H. Vlamakis, R. Kolter, B. S. Moore, and P.-Y. Qian, Sci. Rep., 5, Art. No. 9383 (2015).

  56. S. S. Terekhov, A. S. Nazarov, Y. A. Mokrushina, M. N. Baranova, N. A. Potapova, M. V. Malakhova, E. N. Ilina, I. V. Smirnov, and A. G. Gabibov, Antibiotics, 9 (4), 157 (2020).

    Article  CAS  PubMed Central  Google Scholar 

  57. I. V. Prokhorova, K. A. Akulich, D. S. Makeeva, I. A. Osterman, D. A. Skvortsov, P. V. Sergiev, O. A. Dontsova, G. Yusupova, M. M. Yusupov, and S. E. Dmitriev, Sci. Rep., 6, Art. No. 27720 (2016).

  58. J. Itoh, S. Omoto, T. Shomura, N. Nishizawa, S. Miyado, Y. Yuda, U. Shibata, and S. Inouye, J. Antibiot., 34 (5), 611 (1981).

    Article  CAS  Google Scholar 

  59. H. B. Park, C. E. Perez, E. K. Perry, and J. M. Crawford, Molecules, 21 (7), 824 (2016).

    Article  PubMed Central  CAS  Google Scholar 

  60. J. Bai, H. Pan, et al., CN Pat. 107652262, Feb. 2, 2018.

  61. J. Itoh, S. Omoto, N. Nishizawa, Y. Kodama, and S. Inouye, Agric. Biol. Chem., 46 (11), 2659 (1982).

    CAS  Google Scholar 

  62. Y. Hamada, A. Kawai, Y. Kohno, O. Hara, and T. Shioiri, J. Am. Chem. Soc., 111 (4), 1524 (1989).

    Article  CAS  Google Scholar 

  63. S. D. Broady, J. E. Rexhausen, and E. J. Thomas, J. Chem. Soc., Chem. Commun., 10, 708 (1991).

    Article  Google Scholar 

  64. Y. Hamada, O. Hara, A. Kawai, Y. Kohno, and T. Shioiri, Tetrahedron, 47 (40), 8635 (1991).

    Article  CAS  Google Scholar 

  65. T. Suzuki, T. Nagasawa, M. Enomoto, and S. Kuwahara, Tetrahedron, 71 (13), 1992 (2015).

    Article  CAS  Google Scholar 

  66. R. A. Ward and G. Procter, Tetrahedron, 51 (45), 12301 (1995).

    Article  CAS  Google Scholar 

  67. R. A. Ward and G. Procter, Tetrahedron Lett., 33 (23), 3359 (1992).

    Article  CAS  Google Scholar 

  68. S. D. Broady, J. E. Rexhausen, and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1083 (1999).

  69. J. M. Durgnat and P. Vogel, Helv. Chim. Acta, 76 (1), 222 (1993).

    Article  CAS  Google Scholar 

  70. M. Enomoto and S. Kuwahara, J. Org. Chem., 74 (19), 7566 (2009).

    Article  CAS  PubMed  Google Scholar 

  71. M. Enomoto and S. Kuwahara, Angew. Chem. Int. Ed., 48 (6), 1144 (2009).

    Article  CAS  Google Scholar 

  72. M. Enomoto and S. Kuwahara, J. Syn. Org. Chem. Jpn., 68 (4), 387 (2010).

    Article  CAS  Google Scholar 

  73. K. Kurasawa, S. Kuwahara, and M. Enomoto, Tetrahedron Lett., 57 (45), 4997 (2016).

    Article  CAS  Google Scholar 

  74. G. Wu, S. Liu, T. Wang, Z. Jiang, K. Lv, Y. Wang, and C. Sun, Org. Lett., 20 (12), 3566 (2018).

    Article  CAS  PubMed  Google Scholar 

  75. S. Tsukaguchi, M. Enomoto, R. Towada, Y. Ogura, and S. Kuwahara, Eur. J. Org. Chem., 2019 (35), 6110 (2019).

    Article  CAS  Google Scholar 

  76. S. Shinkaruk, B. Bennetau, P. Babin, J.-M. Schmitter, V. Lamothe, C. Bennetau-Pelissero, and M. C. Urdaci, Bioorg. Med. Chem., 16 (20), 9383 (2008).

    Article  CAS  PubMed  Google Scholar 

  77. J. Bai, D. Liu, S. Yu, P. Proksch, and W. Lin, Tetrahedron Lett., 55 (45), 6286 (2014).

    Article  CAS  Google Scholar 

  78. N. Yu, R. Poulain, A. Tartar, and J.-C. Gesquiere, Tetrahedron, 55 (48), 13735 (1999).

    Article  CAS  Google Scholar 

  79. S. V. Shilin, O. V. Shablykina, V. V. Ishchenko, Yu. N. Zabolotnaya, and V. P. Khilya, Chem. Nat. Compd., 52, 595 (2016).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. S. Moskvina.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2021, pp. 179–198.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shablykina, O.V., Shilin, S.V., Moskvina, V.S. et al. Progress in the Chemistry of Amino-Acid Derivatives of Isocoumarins and 3,4-Dihydroisocoumarins. Chem Nat Compd 57, 209–229 (2021). https://doi.org/10.1007/s10600-021-03323-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-021-03323-z

Keywords

Navigation