Skip to main content
SpringerLink
Log in

Analytical characterization of lichexanthone in lichen: HPLC, UV spectroscopic, and DFT analysis of lichexanthone extracted from Laurera benguelensis (Mull. Arg.) Zahlbr.

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Lichexanthone, the major pigment present in the extract of Laurera benguelensis (Mull. Arg.) Zahlbr., was extracted from lichen, purified, and characterized by high-performance liquid chromatography (HPLC) and ultraviolet (UV) spectroscopy. The geometry of the lichexanthone conformers was optimized at the B3LYP/6-31+G** level of theory. It was found that all conformations have similar energies and that the corresponding lichexanthone radical is planar. In spite of its planarity, there is no significant electron delocalization over the radical. The antioxidant properties of lichexanthone were investigated using the colorimetric assay as Trolox-equivalent antioxidant capacity and at B3LYP/6-31+G** level of theory. Both methods revealed that lichexanthone has weak antioxidant properties. The results confirm the potential of HPLC–UV analysis for taxonomic characterization of lichen species.

Graphical abstract

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.

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

Similar content being viewed by others

References

  1. Yamamoto Y (1991) Production of Lichen Substances. In: Komamine A, Misawa M, DiCosmo F (eds) Plant cell culture in Japan. CMC Co., Tokyo

    Google Scholar 

  2. Langcake P, Pryce RJ (1976) Physiol Plant Pathol 9:77

    Article  CAS  Google Scholar 

  3. Oliveira LFC, Pinto PCC, Marcelli MP, Dos Santos HF, Edwards GMH (2009) J Mol Struct 920:128

    Article  Google Scholar 

  4. Vieira LMM, Kijjoa A (2005) Curr Med Chem 12:2413

    Article  CAS  Google Scholar 

  5. Akao Y, Nakagawa Y, Iinuma M, Nozawa Y (2008) Int J Mol Sci 9:355

    Article  CAS  Google Scholar 

  6. Chen LG, Yang LL, Wang CC (2008) Food Chem Toxicol 46:688

    Article  CAS  Google Scholar 

  7. Pinto MMM, Souza ME, Nascimento MSJ (2005) Curr Med Chem 12:2517

    Article  CAS  Google Scholar 

  8. Yoshikawa M, Harada E, Miki A, Tsukamoto K, Si Qian L, Yamahara J, Murakami N (1994) Yakugaku Zasshi 114:129

    CAS  Google Scholar 

  9. Fan C, Su J (1997) J Chin Agric Chem Soc 35:540

    CAS  Google Scholar 

  10. Vongshewarat K, McCarthy PM, Mongkolsuk P, Boonpagob K (1999) Mycotaxon 70:227

    Google Scholar 

  11. El-Seedi HR, Hazell AC, Torssell KBG (1994) Phytochemistry 35:1297

    Article  CAS  Google Scholar 

  12. Micheletti AC, Beatriz A, Lima DP, Honda NK, Pessoa C, Odorico de Moraes M, Lotufo LV, Magalhães HIF, Carvalho NCP (2009) Quím Nova 32:12

    Article  CAS  Google Scholar 

  13. Wansi JD, Wandji J, Waffo AFK, Ngeufa HE, Ndom JC, Fotso S, Maskey RP, Dieudonné N, Fomum TZ, Laatsch H (2006) Phytochemistry 67:475

    Article  CAS  Google Scholar 

  14. Mayer MJ (2004) Annu Rev Phys Chem 55:363

    Article  CAS  Google Scholar 

  15. Leopoldini M, Pitarch IP, 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. Trouillas P, Fagnère C, Lazzaroni R, Calliste AC, Marfak A, Duroux LJ (2004) Food Chem 88:571

    Article  CAS  Google Scholar 

  18. Huneck S, Yoshimura I (1996) Identification of Lichen Substances. Springer, Berlin

    Google Scholar 

  19. Manojlovic TN, Solujic S, Sukdolak S (2002) Lichenologist 3:83

    Article  Google Scholar 

  20. van Acker SABE, Groot MJ, van der Vijgh WJF, Tromp MNJL, den Kelder GF, van der Vijgh EJF, Bast A (1996) Chem Res Toxicol 9:1305

    Article  Google Scholar 

  21. Rice-Evans CA, Miller NJ, Paganga G (1996) 20:933

  22. Markovic SZ, Manojlovic TN (2009) Monatsh Chem 140:1311

    Article  CAS  Google Scholar 

  23. Cai YZ, Sun M, Xing J, Luo Q, Corke H (2006) Life Sci 78:2872

    Article  CAS  Google Scholar 

  24. Møller S, Andersen KB, Spanget-Larsen J, Yaluk J (1988) Chem Phys Lett 291:51

    Article  Google Scholar 

  25. Szabo A, Ostlund NS (1982) Modern quantum chemistry: introduction to advanced electronic structure theory. Dover, New York

    Google Scholar 

  26. Cai YZ, Luo Q, Sun M, Corke H (2004) Life Sci 74:2157

    Article  CAS  Google Scholar 

  27. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick AD, Rabuck KD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (2003) Gaussian 03, Revision E.01-SMP. Gaussian Inc., Pittsburgh

    Google Scholar 

  28. Becke AD (1992) J Chem Phys 97:9173

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  31. Miertuš S, Scrocco S, Tomasi J (1981) Chem Phys 55:117

    Article  Google Scholar 

  32. Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105:2999

    Article  CAS  Google Scholar 

  33. Jacquemin D, Assfeld X, Preat J, Perpète EA (2007) Mol Phys 105:325

    Article  CAS  Google Scholar 

  34. Zhurko GA, Chemcraft graphical program for working with quantum chemistry results

  35. Merrick JP, Moran DL (2007) J Phys Chem 11:11683

    Google Scholar 

  36. Foster JP, Weinhold F (1980) J Am Chem Soc 102:7211

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge financial support by the Ministry of Science and Environmental of Republic of Serbia (grant no. 142025).

Author information

Authors and Affiliations

  1. Department of Biochemical and Medical Sciences, State University of Novi Pazar, 36300, Novi Pazar, Serbia

    Zoran S. Marković

  2. Department of Pharmacy, Medical Faculty, University of Kragujevac, 34000, Kragujevac, Serbia

    Nedeljko T. Manojlović

Authors
  1. Zoran S. Marković
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nedeljko T. Manojlović
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zoran S. Marković.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Marković, Z.S., Manojlović, N.T. Analytical characterization of lichexanthone in lichen: HPLC, UV spectroscopic, and DFT analysis of lichexanthone extracted from Laurera benguelensis (Mull. Arg.) Zahlbr.. Monatsh Chem 141, 945–952 (2010). https://doi.org/10.1007/s00706-010-0349-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-010-0349-6

Keywords

Search

Navigation