Skip to main content
SpringerLink
Log in

Use of Liposomes to Evaluate the Role of Membrane Interactions on Antioxidant Activity

  • Protocol
  • First Online:
Liposomes

Part of the book series: Methods in Molecular Biology™ ((MIMB,volume 606))

Abstract

Cellular membranes, which contain abundant phospholipids, such as phosphatidylcholine, are major targets subjected to the damage caused by free radicals. Cellular damage due to lipid oxidation is strongly associated with ageing, carcinogenesis and other diseases. In addition, lipid oxidation is an important deteriorative reaction in the processing and storage of lipid-containing foods. Liposomes have been used extensively as biological models for in vitro lipid oxidation studies. The resemblance between the liposomal and membrane bilayer core makes liposomes a very useful tool to investigate the significance of the antioxidant-membrane interactions for antioxidant activity. The antioxidant activity of a compound is strongly influenced by numerous factors including the nature of the lipid substrate, the hydrophilic-lipophilic balance of the antioxidant, the physical and chemical environments of the lipids, and various other interfacial interactions. Thus, compounds that are effective antioxidants in one model system or food matrix may be unsuitable in other systems.

This chapter describes fluorescent probes-based methods commonly used for testing antioxidant activity in liposomes and stresses the need to combine antioxidant assays and drug-membrane interaction studies to get a better description of the antioxidants’ profile considering their location in lipid bilayer and their effect on membrane fluidity and consequently provide additional information to that obtained currently from assays performed in aqueous buffer media.

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

Access this chapter

Log in via an institution
Protocol
USD 49.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 89.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 119.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Halliwell B, Gutteridge JMC (1990) Role of free radicals and catalytic metal ions in human disease: an overview. In: Packer L and Glazer AN (eds) Methods in enzymology. Academic, San Diego, NY

    Google Scholar 

  2. Davies MJ, Dean RT (1997) The pathology of protein oxidation. In: Radical-mediated protein oxidation. Oxford Science Publications, Oxford, UK

    Google Scholar 

  3. Mattson MP (2004) Metal-catalyzed disruption of membrane protein and lipid signaling in the pathogenesis of neurodegenerative disorders. Ann N Y Acad Sci 1012:37-50

    Article  CAS  PubMed  Google Scholar 

  4. Poon HF, Calabrese V, Scapagnini G, Butterfield DA (2004) Free radicals: key to brain aging and heme oxygenase as a cellular response to oxidative stress. J Gerontol A Biol Sci Med Sci 59:478-493

    PubMed  Google Scholar 

  5. Schroepfer GJ (2000) Oxysterols: modulators of cholesterol metabolism and other processes. Physiol Rev 80:361-554

    CAS  PubMed  Google Scholar 

  6. Schnitzer E, Pinchuk I, Lichtenberg D (2007) Peroxidation of liposomal lipids. Eur Biophys J 36:499-515

    Article  CAS  PubMed  Google Scholar 

  7. van Ginkel G, Sevanian A (1994) Lipid peroxidation-induced membrane structural alterations. Methods Enzymol 233:273-288

    Article  PubMed  Google Scholar 

  8. Mason RP, Walter M, Mason P (1997) Effect of oxidative stress on membrane structure: small-angle X-ray diffraction analysis. Free Radic Biol Med 23:419-425

    Article  CAS  PubMed  Google Scholar 

  9. Spiteller G (2003) Are lipid peroxidation processes induced by changes in the cell wall structure and how are these processes connected with diseases? Med Hypotheses 60:69-83

    Article  PubMed  Google Scholar 

  10. Al-Ismail KM, Aburjai T (2004) Antioxidant activity of water and alcohol extracts of chamomile flowers, anise seeds and dill seeds. J Sci Food Agric 84:173-178

    Article  CAS  Google Scholar 

  11. Viljanen K, Kylli P, Kivikari R, Heinonen M (2004) Inhibition of protein and lipid oxidation in liposomes by berry phenolics. J Agric Food Chem 52:7419-7424

    Article  CAS  PubMed  Google Scholar 

  12. Diaz M, Decker EA (2004) Antioxidant mechanisms of caseinophosphopeptides and casein hydrolysates and their application in ground beef. J Agric Food Chem 52:8208-8213

    Article  CAS  PubMed  Google Scholar 

  13. Halliwell B, Gutteridge JMC (1998) Free radicals in biology and medicine. Oxford University Press, Oxford, UK

    Google Scholar 

  14. Baublis A, Decker EA, Clydesdale FM (2000) Antioxidant effect of aqueous extracts from wheat based ready-to-eat breakfast cereals. Food Chem 68:1-6

    Article  CAS  Google Scholar 

  15. Hassimotto NMA, Genovese MI, Lajolo FM (2005) Antioxidant activity of dietary fruits, vegetables, and commercial frozen fruit pulps. J Agric Food Chem 53:2928-2935

    Article  CAS  PubMed  Google Scholar 

  16. Yi O, Jovel EM, Towers GHN, Wahbe TR, Cho D (2007) Antioxidant and antimicrobial activities of native Rosa sp from British Columbia. Canada Int J Food Sci Nutr 58:178-189

    Article  Google Scholar 

  17. Roberts WG, Gordon MH (2003) Determination of the total antioxidant activity of fruits and vegetables by a liposome assay. J Agric Food Chem 51:1486-1493

    Article  CAS  PubMed  Google Scholar 

  18. Yen WJ, Chang LW, Duh PD (2005) Antioxidant activity of peanut seed testa and its antioxidative component, ethyl protocatechuate. LWT-Food Sci Technol 38:193-200

    Article  CAS  Google Scholar 

  19. Frankel EN, Waterhouse AL, Teissedre PL (1995) Principal phenolic phytochemicals in selected California wines and their antioxidant activity in inhibiting oxidation of human low-density lipoproteins. J Agric Food Chem 43:890-894

    Article  CAS  Google Scholar 

  20. Tedesco I, Russo GL, Nazzaro F, Russo M, Palumbo R (2001) Antioxidant effect of red wine anthocyanins in normal and catalase-inactive human erythrocytes. J Nutr Biochem 12:505-511

    Article  CAS  PubMed  Google Scholar 

  21. Morel I, Abalea V, Sergent O, Cillard P, Cillard J (1998) Involvement of phenoxyl radical intermediates in lipid antioxidant action of myricetin in iron-treated rat hepatocyte culture. Biochem Pharmacol 55:1399-1404

    Article  CAS  PubMed  Google Scholar 

  22. Daglia M, Papetti A, Gregotti C, Berte F, Gazzani G (2000) In vitro antioxidant and ex vivo protective activities of green and roasted coffee. J Agric Food Chem 48:1449-1454

    Article  CAS  PubMed  Google Scholar 

  23. Mora A, Paya M, Rios JL, Alcaraz MJ (1990) Structure-activity-relationships of polymethoxyflavones and other flavonoids as inhibitors of nonenzymatic lipid-peroxidation. Biochem Pharmacol 40:793-797

    Article  CAS  PubMed  Google Scholar 

  24. Plumb GW, Chambers SJ, Lambert N, Wanigatunga S, Williamson G (1997) Influence of fruit and vegetable extracts on lipid peroxidation in microsomes containing specific cytochrome P450. Food Chem 60:161-164

    Article  CAS  Google Scholar 

  25. van Acker SABE, van den Berg D-J, Tromp MNJL, Griffioen DH, van Bennekom WP, van der Vijgh WJF, Bast A (1996) Structural aspects of antioxidant activity of flavonoids. Free Radic Biol Med 20:331-342

    Article  PubMed  Google Scholar 

  26. de Beer D, Joubert E, Gelderblom WCA, Manley M (2005) Antioxidant activity of South African red and white cultivar wines and selected phenolic compounds: in vitro inhibition of microsomal lipid peroxidation. Food Chem 90:569-577

    Article  Google Scholar 

  27. Roginsky V, Barsukova T (2001) Chain-breaking antioxidant capability of some beverages as determined by the clark electrode technique. J Med Food 4:219-229

    Article  CAS  PubMed  Google Scholar 

  28. Shi H, Noguchi N, Niki E (1999) Comparative study on dynamics of antioxidative action of alpha-tocopheryl hydroquinone, ubiquinol, and alpha-tocopherol against lipid peroxidation. Free Radic Biol Med 27:334-346

    Article  CAS  PubMed  Google Scholar 

  29. Goñi MF, Alonso A (1989) Studies of phospholipid peroxidation in liposomes. In: CRC handbook of free radicals and antioxioxidants in biomedicine. CRC, Boca Raton, FL

    Google Scholar 

  30. Murakami M, Yamaguchi T, Takamura H, Matoba T (2002) A comparative study on the various in vitro assays of active oxygen scavenging activity in foods. J Food Sci 67:539-541

    Article  CAS  Google Scholar 

  31. Niki E, Noguchi N (2000) Evaluation of antioxidant capacity. What capacity is being measured by which method? Life 50:323-329

    CAS  PubMed  Google Scholar 

  32. Fernandes E, Costa D, Toste SA, Lima JLFC, Reis S (2004) In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs. Free Radic Biol Med 37:1895-1905

    Article  CAS  PubMed  Google Scholar 

  33. Kachel K, Asuncion-Punzalan E, London E (1998) The location of fluorescent probes with charged groups in model membranes. Biochim Biophys Acta 1374:63-76

    Article  CAS  PubMed  Google Scholar 

  34. Kaiser RD, London E (1998) Location of diphenylhexatriene (DPH) and its derivatives within membranes: comparison of different fluorescence quenching analysis of membrane depth. Biochemistry 37:8180-8190

    Article  CAS  PubMed  Google Scholar 

  35. Ou B, Hampsch-Woodill M, Prior RL (2001) Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J Agric Food Chem 49:4619-4626

    Article  CAS  PubMed  Google Scholar 

  36. Broniowska KA, Kirilyuk I, Wisniewska A (2007) Spin-labelled lutein as a new antioxidant in protection against lipid peroxidation. Free Radical Res 41:1053-1060

    Article  CAS  Google Scholar 

  37. Barclay L, Vinqvist MR (1994) Membrane peroxidation: inhibiting effects of water soluble antioxidants on phospholipids of different charge types. Free Radic Biol Med 16:779-788

    Article  CAS  PubMed  Google Scholar 

  38. Gutiérrez ME, García AF, Africa de Mandariaga M, Sagrista ML, Casadó FJ, Mora M (2003) Interaction of tocopherols and phenolic compounds with membrane lipid components: evaluation of their antioxidant activity in a liposomal model system. Life Sci 72:2337-2360

    Article  PubMed  Google Scholar 

  39. Saija A, Scalese M, Lanza M, Marzullo D, Bonina F, Castelli F (1995) Flavonoids as antioxidant agents: importance of their interaction with biomembranes. Free Radic Biol Med 19:481-486

    Article  CAS  PubMed  Google Scholar 

  40. Lúcio M, Ferreira H, Lima JLFC, Reis S (2007) Use of liposomes to evaluate the role of membrane interactions on antioxidant activity. Anal Chim Acta 597:163-170

    Article  PubMed  Google Scholar 

  41. Brooks P (1998) Use and benefits of nonsteroidal anti-inflammatory drugs. Am J Med 104:9S-13S

    Article  Google Scholar 

  42. Kitamura K, Imayoshi N, Goto T, Shiro H, Mano T, Nakai Y (1995) Second derivative spectrophotometric determination of partition coefficients of chlorpromazine and promazine between lecithin bilayer vesicles and water. Anal Chim Acta 304:101-106

    Article  CAS  Google Scholar 

  43. Kitamura K, Imayoshi N (1992) Second-derivative spectrophotometric determination of the binding constant between chlorpromazine and -cyclodextrin in aqueous solutions. Anal Sci 8:497-501

    Article  CAS  Google Scholar 

  44. Ferreira H, Lúcio M, Castro B, Gameiro P, Lima JLFC, Reis S (2003) Partition and location of nimesulide in EPC liposomes: a spectrophotometric and fluorescence study. Anal Bioanal Chem 377:293-298

    Article  CAS  PubMed  Google Scholar 

  45. Lakowicz JR (1999) Principles of fluorescence spectroscopy. Kluwer Academic/Plenum, New York

    Google Scholar 

  46. Lentz BR (1993) Use of fluorescent probes to monitor molecular order and motions within liposome bilayers. Chem Phys Lipids 64:99-116

    Article  CAS  PubMed  Google Scholar 

  47. Barclay LRC, Artz JD, Mowat JJ (1995) Partitioning and antioxidant action of the water-soluble antioxidant, trolox, between the aqueous and lipid phases of phosphatidylcholine membranes - C-14 tracer and product studies. Biochim Biophys Acta 1237:77-85

    Article  PubMed  Google Scholar 

  48. Wang S, Beechem JM, Gratton E, Glaser M (1991) Orientational distribution of 1, 6-diphenyl- 1, 3, 5-hexatriene in phospholipid vesicles as determined by global analysis of frequency domain fluorimetry data. Biochemistry 30:5565-5512

    Article  CAS  PubMed  Google Scholar 

  49. Repáková J, Holopainen JM, Morrow MR, McDonald MC, Capková P, Vattulainen I (2005) Influence of DPH on the structure and dynamics of a DPPC bilayer. Biophys J 88:3398-3410

    Article  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. REQUIMTE, Faculdade de Farmácia, Universidade do Porto, Porto, Portugal

    Salette Reis, Marlene Lúcio, Marcela Segundo & José L. F. C. Lima

Authors
  1. Salette Reis
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marlene Lúcio
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marcela Segundo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. José L. F. C. Lima
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Salette Reis .

Editor information

Editors and Affiliations

  1. College of Pharmacy, Midwestern University, N. 59th Avenue 19555, Glendale, 85308, U.S.A.

    Volkmar Weissig

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Humana Press, a part of Springer Science+Business Media, LLC

About this protocol

Cite this protocol

Reis, S., Lúcio, M., Segundo, M., Lima, J.L.F.C. (2010). Use of Liposomes to Evaluate the Role of Membrane Interactions on Antioxidant Activity. In: Weissig, V. (eds) Liposomes. Methods in Molecular Biology™, vol 606. Humana Press. https://doi.org/10.1007/978-1-60761-447-0_13

Download citation

  • DOI: https://doi.org/10.1007/978-1-60761-447-0_13

  • Published:

  • Publisher Name: Humana Press

  • Print ISBN: 978-1-60761-446-3

  • Online ISBN: 978-1-60761-447-0

  • eBook Packages: Springer Protocols

Publish with us

Policies and ethics

Search

Navigation