Skip to main content
SpringerLink
Log in

Antioxidant properties ofErigeron annuus extract and its three phenolic constituents

  • Published:
Biotechnology and Bioprocess Engineering Aims and scope Submit manuscript

Abstract

The antioxidant activity of the extract ofErigeron annuus was assessed by means of two differentin vitro tests: bleaching of the stable 1,1-diphenyl-2-picrylhydrazyl radical (DPPH test) and the scavenging of authentic peroxynitrite in company with peroxynitrite generation from 3-morpholinosydnonimine (SIN-1). In both tests, the 85% aq. MeOH andn-BuOH soluble fractions of the crude extract showed a significant scavenging effect on peroxynitrite and DPPH radical in comparison to L-ascorbic acid. And bioassay-guided fractionation of then-BuOH soluble fraction led to the isolation of three compounds: Apigenin (1), quercetin-3-O-glucoside (2), and caffeic acid (3). The structures of the isolated compounds were elucidated on the basis of their spectroscopic data and their antioxidant activities were measured by determining their capacity to scavenge peroxynitrite and the DPPH radical.

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. Fang, Y. Z., S. Yang, and G. Wu (2002) Free radicals, antioxidants, and nutrition.Nutrition 18: 872–879.

    Article  CAS  Google Scholar 

  2. Patel, R. P., J. McAndrew, H. Sellak, C. R. White, H. Jo, B. A. Freeman, and V. M. Darley-Usmar (1999) Biological aspects of reactive nitrogen species.Biochim. Biophys. Acta 1411: 385–400.

    Article  CAS  Google Scholar 

  3. Grace, S. C., M. G. Salgo, and W. A. Pryor (1998) Scavenging of peroxynitrite by a phenolic/peroxidase system prevents oxidative damage to DNA.FEBS Lett. 426: 24–28.

    Article  CAS  Google Scholar 

  4. Virag, L., E. Szabo, P. Gergely, and C. Szabo (2003) Peroxynitrite-induced cytotoxicity: mechanism and opportunities for intervention.Toxicol. Lett. 140–141: 113–124.

    Article  CAS  Google Scholar 

  5. Reiter, R. J., D. X. Tan, and S. Burkhardt (2002) Reactive oxygen and nitrogen species and cellular and organismal decline: amelioration with melatonin.Mech. Ageing Dev. 123: 1007–1019.

    Article  CAS  Google Scholar 

  6. Heijnen, C. G. M., G. R. M. M. Haenen, and J. A. J. M. Vekemans (2001) Peroxynitrite scavenging of flavonoids: Structure activity relationship.Environ. Toxicol. Pharmacol. 10: 199–206.

    Article  CAS  Google Scholar 

  7. Heijnen, C. G. M., G. R. M. M. Haenen, F. A. A. van Acker, W. J. F. van der Vijgh, and A. Bast (2001) Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups.Toxicol. In Vitro 15: 3–6.

    Article  CAS  Google Scholar 

  8. Chung, H. Y., H. R. Choi, H. J. Park, J. S. Choi, and W. C. Choi (2001) Peroxynitrite scavenging and cytoprotective activity of 2,3,4-tribromo-4,5-dihydroxybenzyl methyl ether from the marine algaSymphycladia latiuscula.J. Agric. Food Chem. 49: 3614–3621.

    Article  CAS  Google Scholar 

  9. Blois, M. S. (1958) Antioxidant determination by the use of a stable free radical.Nature 181: 1199–1202.

    Article  CAS  Google Scholar 

  10. Lee, H. J., Y. A. Kim, J. W. Ahn, B. J. Lee, S. G. Moon, and Y. Seo (2004) Screening of peroxynitrite and DPPH radical scavenging activities from salt marsh plants.Kor. J. Biotechnol. Bioeng. 19: 57–61.

    Google Scholar 

  11. Lee, H. J., K. E. Park, J. S. Yoo, J. W. Ahn, B. J. Lee, and Y. Seo (2004) Studies on screening of seaweed extracts for peroxynitrite and DPPH radical scavenging activities.Ocean and Polar Research 26: 59–64.

    Google Scholar 

  12. Bennington, C. C. and D. A. Stratton (1998) Field tests of density and frequency-dependent selection inErigeron annuus (Compositae).Am. J. Bot. 85: 540–545.

    Article  Google Scholar 

  13. Kim, T. S. and H. J. Lee (1991) Life history and growth pattern on theErigeron annuus.Kor. J. Ecol. 14: 211–231.

    Google Scholar 

  14. Kim, T. S., H. J. Lee, and D. W. Byun (1992) Germination, shade tolerance and community characteristics ofErigeron annuus L. in Cheju,Kor. J. Ecol. 15: 103–116.

    Google Scholar 

  15. Shanghai Scientific Technological Publishers and Shougakukan. (eds.).Dictionary of Chinese Materia Medica. vol. 1. Shougakukan, Tokyo, 1985, pp. 25.

    Google Scholar 

  16. Oh, H., S. Lee, H. S. Lee, D. H. Lee, S. Y. Lee, H. T. Chung, T. S. Kim, and T. O. Kwon (2002) Germination inhibitory constituents fromErigeron annuus.Phytochemistry 61: 175–179.

    Article  CAS  Google Scholar 

  17. Iijima, T., Y. Yaoita, and M. Kikuchi (2003) Two new cyclopentenone derivatives and a new cyclooctadienone derivative fromErigeron annuus (L.) PERS.,Erigeron philadelphicus L., andErigeron sumatrensis RETZ.Chem. Pharm. Bull. 51: 894–896.

    Article  CAS  Google Scholar 

  18. Iijima, T., Y. Yaoita, and M. Kikuchi (2003) Five new sesquiterpenoids and a new diterpenoid fromErigeron annuus (L.) PERS.,Erigeron philadelphicus L. andErigeron sumatrensis RETZ.Chem. Pharm. Bull. 51: 545–549.

    Article  CAS  Google Scholar 

  19. Kooy, N. W., J. A. Royall, H. Ischiropoulos, and J. S. Beckman (1994) Peroxynitrite-mediated oxidation of dihydrorhodamine 123.Free Radic. Biol. Med. 16: 149–156.

    Article  CAS  Google Scholar 

  20. Wagner, H. and V. M. Chari (1976)13C-NMR spektren naturlich vorkommender flavonoide.Tetrahedron Lett. 21: 1799–1802.

    Article  Google Scholar 

  21. Saleem, M., H. J. Kim, C. Jin, and Y. S. Lee (2004) Antioxidant caffeic acid derivatives from leaves of Parthenocissus tricuspidata.Arch. Pharm. Res. 27: 300–304.

    Article  CAS  Google Scholar 

  22. Harborne, J. B. (1982)The Flavonoids: Advances in Research. pp. 60. Champman and Hall, London, UK.

    Google Scholar 

  23. Harborne, J. B. (1994)The Flavonoids: Advances in Research. pp. 453. Champman and Hall.

  24. Niwa, T., U. Doi, Y. Kato, and T. Osawa (1999) Inhibitory mechanism of sinapinic acid against peroxynitritemediated tyrosine nitration of proteinin vitro.FEBS Lett. 459: 43–46.

    Article  CAS  Google Scholar 

  25. Pannala, A. S., R. Razaq, B. Halliwell, S. Singh, and C. A. Rice-Evans (1998) Inhibition of peroxynitrite dependent tyrosine nitration by hydroxycinnamates: nitration or electron donation?Free Radic. Biol. Med. 24: 594–606.

    Article  CAS  Google Scholar 

  26. Ippoushi, K., K. Azuma, H. Ito, H. Horie, and H. Higashio (2003) [6]-Gingerol inhibits nitric oxide synthesis in activated J774.1 mouse macrophages and prevents peroxynitrite-induced oxidation and nitration reactions.Life Sci. 73: 3427–3437.

    Article  CAS  Google Scholar 

  27. Robards, K., P. D. Prenzler, G. Tucker, P. Swatsitang, and W. Glover (1999) Phenolic compounds and their role in oxidative processes in fruits.Food Chem. 66: 401–436.

    Article  CAS  Google Scholar 

  28. Tsuda, T., Y. Kato, and T. Osawa (2000) Mechanism for the peroxynitrite scavenging activity by anthocyanins.FEBS Lett. 484: 207–210.

    Article  CAS  Google Scholar 

  29. Hur, Y. S., T. H. Hong, and W. H. Hong (2004) Effective extraction of oligomeric proanthocyanidin (OPC) from wild grape seeds.Biotechnol. Bioprocess Eng. 9: 471–475.

    Article  Google Scholar 

  30. Liebert, M., U. Licht, V. Bohm, and R. Bitsch (1999) Antioxidant properties and total phenolics content of green and black tea under different brewing conditions.Z. Lebensm. Unters. Forsch. A 208: 217–220.

    Article  CAS  Google Scholar 

  31. Johnson, M. K. and G. Loo (2000) Effects of epigallocatechin gallate and quercetin on oxidative damage to cellular DNA.Mutat. Res. 459: 211–218.

    CAS  Google Scholar 

  32. Ketsawatsakul, U., M. Whiteman, and B. Halliwell (2000) A reevaluation of the peroxynitrite scavenging activity of some dietary phenolics.Biochem. Biophys. Res. Commun. 279: 692–699.

    Article  CAS  Google Scholar 

  33. Kono, Y., K. Kobayashi, S. Tagawa, K. Adachi, A. Ueda, Y. Sawa, and H. Shibata (1997) Antioxidant activity of polyphenolics in diets rate constants of reactions of chlorogenic acid and caffeic acid with reactive species of oxygen and nitrogen.Biochim. Biophys. Acta 1335: 335–342.

    CAS  Google Scholar 

  34. Shutenko, Z., Y. Henry, E. Pinard, J. Seylaz, P. Potier, F. Berthet, P. Girard and R. Sercombe (1999) Influence of the antioxidant quercetinin vivo on the level of nitric oxide determined by electron paramagnetic resonance in rat brain during global ischemia and reperfusion.Biochem. Pharmacol. 57: 199–208.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute of Marine Science and Technology (RIMST), Korea Maritime University, 606-791, Busan, Korea

    Hee Jung Lee

  2. Division of Marine Environment and Bioscience, Korea Maritime University, 606-791, Busan, Korea

    Youngwan Seo

Authors
  1. Hee Jung Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Youngwan Seo
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Youngwan Seo.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lee, H.J., Seo, Y. Antioxidant properties ofErigeron annuus extract and its three phenolic constituents. Biotechnol. Bioprocess Eng. 11, 13–18 (2006). https://doi.org/10.1007/BF02931862

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02931862

Keywords

Search

Navigation