Skip to main content
SpringerLink
Log in

Phytotoxic studies of naphthoquinone intermediates from the synthesis of the natural product Naphthotectone

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

1,4-Naphthoquinones exhibit strong activity as antimalarial, antibacterial, antifungal and anticancer agents. These kinds of compounds have also shown phytotoxic activity. The first example of an allelochemical to be described was naphthoquinone juglone (5-hydroxy-1,4-naphthoquinone). This fact led us to conduct a study of the phytotoxic activity and structure–activity relationships of 26 naphthazarin derivatives. The compounds belong to two main groups, 5,8-dioxygenated-1,4-naphthoquinones and 1,4,5,8-tetraoxygenated naphthalenes with different functionalizations and chains at positions 2, 4, 6 and 7. The results show that substitution with halogens and modification of the hydroxyl groups on the aromatic ring with methoxy or acetate groups seems to play an important role in enhancing the activity.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. J.L. Bolton, M.A. Trush, T.M. Penning, G. Dryhurst, T.J. Monks, Chem. Res. Toxicol. 13, 135–160 (2000)

    Article  CAS  Google Scholar 

  2. T.M. Penning, M.E. Burczynski, C.F. Hung, K.D. McCoull, N.T. Palackal, L.S. Tsuruda, Chem. Res. Toxicol. 12, 1–18 (1999)

    Article  CAS  Google Scholar 

  3. A.V. Pinto, S.L. de Castro, Molecules 14, 4570–4590 (2009)

    Article  Google Scholar 

  4. K. Abdelmohsen, P. Patak, C. Von Montfort, I. Melchheier, H. Sies, L.O. Klotz, Methods Enzymol. 378, 258–272 (2004)

    Article  CAS  Google Scholar 

  5. M.J. Shearer, P. Newman, Thromb. Haemost. 100, 530–547 (2008)

    CAS  Google Scholar 

  6. A. Eiguren-Fernandez, A.H. Miguel, E. Di Stefano, D.A. Schmitz, A.K. Cho, S. Thurairatnam, E.L. Avol, J.R. Froines, Aerosol Sci. Technol. 42, 854–861 (2008)

    Article  CAS  Google Scholar 

  7. V.K. Tandon, R.B. Chhor, R.V. Singh, S. Rai, D.B. Yadav, Bioorg. Med. Chem. Lett. 14, 1079–1083 (2004)

    Article  CAS  Google Scholar 

  8. L.-O. Klotz, X. Hou, C. Jacob, Molecules 19, 14902–14918 (2014)

    Article  Google Scholar 

  9. T.J. Donohoe, C.R. Jones, L.C.A. Barbosa, J. Am. Chem. Soc. 133, 16418–16421 (2011)

    Article  CAS  Google Scholar 

  10. A.D. Bolzan, M.S. Bianchi, Mutat. Res. 488, 25–37 (2001)

    Article  CAS  Google Scholar 

  11. S. Jose, in Chemical Ecology of Plants: Allelopathy in Aquatic and Terrestrial Ecosystems, ed. by A. Mallik, Inderjit (Birkhäuser, Basel, 2002), pp. 149–172

    Chapter  Google Scholar 

  12. E.F. Davis, Am. J. Bot. 15, 620 (1928)

    Google Scholar 

  13. R. Durand, M.H. Zenk, Tetrahedron Lett. 12, 3009–3012 (1971)

    Article  Google Scholar 

  14. R.B. Herbert, The Biosynthesis of Secondary Metabolites (Springer, Netherlands, 1989)

    Book  Google Scholar 

  15. Y.P.S. Bajaj, Medicinal and Aromatic Plants XI (Springer, New York, 1999)

    Book  Google Scholar 

  16. G.F. Spencer, L.W. Tjarks, R.E. England, E.P. Seest, J. Nat. Prod. 49, 530–533 (1986)

    Article  CAS  Google Scholar 

  17. G.P. Richard, F.S. Gayland, Biologically Active Natural Products (American Chemical Society, New York, 1988), pp. 211–232

    Google Scholar 

  18. V.P. Papageorgiou, Planta Med. 38, 193–203 (1980)

    Article  CAS  Google Scholar 

  19. V.P. Papageorgiou, A.N. Assimopoulou, E.A. Couladouros, D. Hepworth, K.C. Nicolaou, Angew. Chem. Int. Ed. 38, 270–301 (1999)

    Article  Google Scholar 

  20. D.S. Seigler, Plant Secondary Metabolism (Springer US, New York, 1998), pp. 76–93

    Book  Google Scholar 

  21. C.J. Krishna, P. Singh, R.T. Pardasani, Planta Med. 32, 71–75 (1977)

    Article  CAS  Google Scholar 

  22. R.M. Khan, S.M. Mlungwana, Phytochemistry 50, 439–442 (1999)

    Article  CAS  Google Scholar 

  23. R. Lacret, R. Varela, J.G. Molinillo, C. Nogueiras, F. Macías, J. Chem. Ecol. 37, 1341–1348 (2011)

    Article  CAS  Google Scholar 

  24. J.M. Sánchez-Calvo, G.R. Barbero, G. Guerrero-Vásquez, A.G. Durán, M. Macías, M.A. Rodríguez-Iglesias, J.M.G. Molinillo, F.A. Macías, Med. Chem. Res. 25, 1274–1285 (2016)

    Article  Google Scholar 

  25. G.A. Guerrero-Vasquez, C.K.Z. Andrade, J.M.G. Molinillo, F.A. Macias, Eur. J. Org. Chem. 2013, 6175–6180 (2013)

    Article  CAS  Google Scholar 

  26. A. Terada, Y. Tanoue, A. Hatada, H. Sakamoto, Bull. Chem. Soc. Jpn. 60, 205–213 (1987)

    Article  CAS  Google Scholar 

  27. C.R. Hancock, H.W.B. Barlow, H.J. Lacey, J. Exp. Bot. 15, 166–176 (1964)

    Article  Google Scholar 

  28. J.P. Nitsch, C. Nitsch, Plant Physiol. 31, 94–111 (1956)

    Article  CAS  Google Scholar 

  29. A. Martín Andrés, J.D. Luna del Castillo, Bioestadística para las Ciencias de la Salud (Norma, Madrid, 1990)

    Google Scholar 

  30. F.A. Macias, D. Castellano, J.M.G. Molinillo, J. Agric. Food Chem. 48, 2512–2521 (2000)

    Article  CAS  Google Scholar 

  31. D. Castellano, F.A. Macías, M. Castellano, R.M. Cambronero, FITOMED (Automated system for measurement of variable lengths). Spain Patent P9901565, 16 April 2001 (1999)

  32. G. Software, PRISM 4.0 (San Diego, CA, 2003)

  33. S. Inc., Statistica for Windows (Tulsa, OK, 2010)

  34. P. Jeschke, Pest Manag. Sci. 66, 10–27 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the Spanish Ministry of Science and Technology, Project No. AGL2013-42238-R, and Consejería de Innovación, Ciencia e Industria (AGR-5822). We also acknowledge the Spanish Ministry of Science and Technology for fellowships.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, INBIO (Institute of Biomolecules), School of Sciences, University of Cadiz, Campus de Excelencia Internacional Agroalimentario, ceiA3, C/República Saharaui, n 7, 11510, Puerto Real, Spain

    Nuria Chinchilla, Guillermo A. Guerrero-Vásquez, Rosa M. Varela, José M. G. Molinillo & Francisco A. Macías

Authors
  1. Nuria Chinchilla
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Guillermo A. Guerrero-Vásquez
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rosa M. Varela
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. José M. G. Molinillo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Francisco A. Macías
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Francisco A. Macías.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chinchilla, N., Guerrero-Vásquez, G.A., Varela, R.M. et al. Phytotoxic studies of naphthoquinone intermediates from the synthesis of the natural product Naphthotectone. Res Chem Intermed 43, 4387–4400 (2017). https://doi.org/10.1007/s11164-017-2884-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-017-2884-9

Keywords

Search

Navigation