Skip to main content
SpringerLink
Log in

Structural and Electronic Characterization of Antioxidants from Marine Organisms

  • Regular Article
  • Published:
Theoretical Chemistry Accounts Aims and scope Submit manuscript

Abstract

Density functional theory was employed to investigate the molecular properties of new systems that serve as antioxidants in the marine environment. The B3LYP/6-311++G** protocol was used for all computations. Investigation, performed in gas phase and in solvent, was devoted mainly to the determination of the O–H bond dissociation enthalpies and the ionization potentials of examined compounds, since these quantities represent the most important parameters on which the biological activity can be rationalized. The results, interpreted in terms of conjugation and delocalization effects acting on molecules and all their possible radicals, showed that between the studied systems the hydroquinone derivatives have the greatest potentiality as antioxidants.

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

Similar content being viewed by others

References

  1. Abdel-Lateff A, König GM, Fisch KM, Höller U, Jones PG, Wright AD (2002). J Nat Prod 65:1605 and references therein

    Article  CAS  Google Scholar 

  2. Tanaka M, Nara F, Yamasato Y, Ono Y, Ogita T (1999). J Antibiot 52:827

    CAS  Google Scholar 

  3. Wright JS, Johnson ER, Di Labio GA (2001). J Am Chem Soc 123:1173

    Article  CAS  Google Scholar 

  4. Gaussian 03 Revision A1 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala P Y, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov B B, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, and Pople JA (2004). Gaussian 03 Revision A1 Frisch, Gaussian Inc., Wallingford CT

  5. Becke AD (1993). J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  6. Lee C, Yang W, Parr RG (1988). Phys Rev B 37:785

    Article  CAS  Google Scholar 

  7. McLean AD, Chandler GS (1980). J Chem Phys 72:5639

    Article  CAS  Google Scholar 

  8. Krisknan R, Binkley JS, Seeger R, Pople JA (1980). J Chem Phys 72:650

    Article  Google Scholar 

  9. Weinhold F, Carpenter JE (1988). Plenum, Newyork P 227 (and references therein)

  10. Miertos S, Scrocco E, Tomasi J (1981). J Chem Phys 55:117

    Article  Google Scholar 

  11. Miertos S, Tomasi J (1982). J Chem Phys 65:239

    Article  Google Scholar 

  12. Cossi M, Barone V, Commi R, Tomasi (1996). J Chem Phys Lett 255:327

    Article  CAS  Google Scholar 

  13. Barone V, Cossi M, Tomasi J (1997). J Chem Phys 107:3210

    Article  CAS  Google Scholar 

  14. Leopoldini M, Marino T, Russo N, Toscano M (2004). J Phys Chem A 108:4916

    Article  CAS  Google Scholar 

  15. Leopoldini M, Pietro Pitarch I, Russo N, Toscano M (2004). J Phys Chem A 108:92

    Article  CAS  Google Scholar 

  16. Leopoldini M, Marino T, Russo N, Toscano M (2004). Theor Chem Acc 111:210

    CAS  Google Scholar 

  17. DiLabio GA, Pratt DA, LoFaro AD, Wright JS (1999). J Phys Chem A 103:1653

    Article  CAS  Google Scholar 

  18. Himo F, Eriksson LA, Blomberg MRA, Siegbahn PEM (2000). Int J Quantum Chem 76:714

    Article  CAS  Google Scholar 

  19. Mulder P, Saastad OW, Griller D (1988). J Am Chem Soc 110:4090

    Article  CAS  Google Scholar 

  20. Denisov ET, Khudyakov IV. (1987). Chem Rev 87:1313

    Article  CAS  Google Scholar 

  21. Wayner DDM, Lusztyk E, Pagé D, Ingold KU, Mulder P, Laarhoven LJJ, Aldrich HS (1995). J Am Chem Soc 117:8737

    Article  CAS  Google Scholar 

  22. Arnett EM, Flowers RA (1993). Chem Soc Rev 9:22

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Chimica and Centro di Calcolo ad Alte Prestazioni per Elaborazioni Parallele e Distribuite-Centro d‘Eccellenza MIUR, Universita’ della Calabria, 87030, Arcavacata di Rende (CS), Italy

    Marcella Belcastro, Tiziana Marino, Nino Russo & Marirosa Toscano

Authors
  1. Marcella Belcastro
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tiziana Marino
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nino Russo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Marirosa Toscano
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nino Russo.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Cite this article

Belcastro, M., Marino, T., Russo, N. et al. Structural and Electronic Characterization of Antioxidants from Marine Organisms. Theor Chem Acc 115, 361–369 (2006). https://doi.org/10.1007/s00214-006-0077-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00214-006-0077-5

Keywords

Search

Navigation