The Journal of Nutritional Biochemistry
Volume 21, Issue 8 , Pages 726-735 , August 2010

Oleuropein aglycon prevents cytotoxic amyloid aggregation of human amylin

  • Stefania Rigacci

      Affiliations

    • Department of Biochemical Sciences, University of Florence, Viale Morgagni 50, 50134 Florence, Italy
    • Corresponding Author InformationCorresponding author. Tel.: +39 055 4598346; fax: +39 055 4598905.
  • ,
  • Valentina Guidotti

      Affiliations

    • Department of Biochemical Sciences, University of Florence, Viale Morgagni 50, 50134 Florence, Italy
  • ,
  • Monica Bucciantini

      Affiliations

    • Department of Biochemical Sciences, University of Florence, Viale Morgagni 50, 50134 Florence, Italy
    • Research Center on the Molecular Basis of Neurodegeneration, Viale Morgagni, 50, 50134 Florence, Italy
  • ,
  • Matteo Parri

      Affiliations

    • Department of Biochemical Sciences, University of Florence, Viale Morgagni 50, 50134 Florence, Italy
  • ,
  • Chiara Nediani

      Affiliations

    • Department of Biochemical Sciences, University of Florence, Viale Morgagni 50, 50134 Florence, Italy
  • ,
  • Elisabetta Cerbai

      Affiliations

    • Department of Preclinical and Clinical Pharmacology, University of Florence, Viale Pieraccini 6, 50139 Florence, Italy
  • ,
  • Massimo Stefani

      Affiliations

    • Department of Biochemical Sciences, University of Florence, Viale Morgagni 50, 50134 Florence, Italy
    • Research Center on the Molecular Basis of Neurodegeneration, Viale Morgagni, 50, 50134 Florence, Italy
  • ,
  • Andrea Berti

      Affiliations

    • Department of Biochemical Sciences, University of Florence, Viale Morgagni 50, 50134 Florence, Italy
    • Research Center on the Molecular Basis of Neurodegeneration, Viale Morgagni, 50, 50134 Florence, Italy

Received 3 December 2008 ,Revised 6 April 2009 ,Accepted 22 April 2009.

References 

  1. Stefani M, Dobson CM. Protein aggregation and aggregate toxicity: new insights into protein folding, misfolding diseases and biological evolution. J Mol Med. 2003;81:678–699
  2. Ludvik B, Kautzky-Willer A, Prager R, Thomaseth K, Pacini G. Amylin: history and overview. Diabet Med. 1997;14(Suppl 2):S9–S13
  3. Padrick SB, Miranker AD. Islet amyloid: phase partitioning and secondary nucleation are central to the mechanism of fibrillogenesis. Biochemistry. 2002;41:4694–4703
  4. Rocken C, Linke RP, Saeger W. Immunohistology of islet amyloid polypeptide in diabetes mellitus: semi-quantitative studies in a post-mortem series. Virchows Arch A Pathol Anat Histopathol. 1992;421:339–344
  5. Matveyenko AV, Butler PC. β-cell deficit due to increased apoptosis in the human Islet Amyloid Polypeptide Transgenic (HIP) rat recapitulates the metabolic defects present in Type 2 Diabetes. Diabetes. 2006;55:2106–2114
  6. Höppener JWM, Lips CJ. Role of Islet amyloid in Type 2 diabetes mellitus. Int J Biochem Cell Biol. 2006;38:726–736
  7. Ritzel RA, Butler PC. Replication increases beta-cell vulnerability to human islet amyloid polypeptide-induced apoptosis. Diabetes. 2003;52:1701–1708
  8. Chiti F, Dobson CM. Protein misfolding, functional amyloid, and human disease. Annu Rev Biochem. 2006;75:333–366
  9. Haataja L, Gurlo T, Huang J, Butler PC. Islet amyloid in Type 2 diabetes, and the toxic oligomer hypothesis. Endocrin Rev. 2008;29:303–316
  10. Bucciantini M, Calloni G, Chiti F, Formigli L, Nosi D, Dobson CM, et al. Pre-fibrillar amyloid protein aggregates share common features of cytotoxicity. J Biol Chem. 2004;279:31374–31382
  11. Butterfield AD. Amyloid β-peptide (1-42)-induced oxidative stress and neurotoxicity: implications for neurodegeneration in Alzheimer's disease brain. A review. Free Radic Res. 2002;36:1307–1313
  12. Soler-Rivas C, Espin JC, Wichers HJ. Oleuropein and related compounds. J Sci Food Agric. 2000;80:1013–1023
  13. Visioli F, Poli A, Galli C. Antioxidant and other biological activities of phenols from olives and olive oil. Med Res Rev. 2002;22:65–75
  14. Visioli F, Bellosta S, Galli C. Oleuropein, the bitter principles of olives, enhances nitric oxide production by mouse macrophages. Life Sci. 1998;62:541–546
  15. Carluccio MA, Siculella L, Ancora MA, Massaro M, Scoditti E, Storelli C, et al. Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of mediterranean diet phytochemicals. Arterioscler Thromb Vasc Biol. 2003;23:622–629
  16. Owen RW, Giacosa A, Hull WE, Haubner R, Würtele G, Spiegelhalder B, et al. Olive oil consumption and health: the possible role of antioxidants. Lancet Oncol. 2000;1:107–112
  17. Andreadou I, Sigala F, Iliodromitis EK, Papaefthimiou M, Sigalas C, Aligiannis N, et al. Acute doxorubicin cardiotoxicity is successfully treated with the phytochemical oleuropein through suppression of oxidative and nitrosative stress. J Mol Cell Cardiol. 2007;42:549–558
  18. Andreadou I, Iliodromitis EK, Mikros E, Constantinou M, Agalias A, Magiatis P, et al. The olive constituent oleuropein exhibits anti-ischemic, antioxidative, and hypolipidemic effects in anesthetized rabbits. J Nutr. 2006;136:2213–2219
  19. Bazoti FN, Bergquist J, Markides KE, Tsarbopoulos A. Noncovalent interaction between amyloid-β-peptide (1-40) and oleuropein studied by electrospray ionization mass spectrometry. J Am Soc Mass Spectrom. 2006;17:568–575
  20. Bazoti FN, Bergquist J, Markides K, Tsarbopoulos A. Localization of the noncovalent binding site between amyloid-β-peptide and oleuropein using electrospray ionization FT-ICR mass spectrometry. J Am Soc Mass Spectrom. 2008;19:1078–1085
  21. Meier JJ, Kayed R, Lin CY, Gurlo T, Haataja L, Jayasinghe SJ, et al. Inhibition of human IAPP fibril formation does not prevent β-cell death: evidence for distinct actions of oligomers and fibrils of human IAPP. Am J Physiol Endocrinol Metab. 2006;291:1317–1324
  22. Yan LM, Tatarek-Nossol M, Velkova A, Kazantzis A, Kapurniotu A. Design of a mimic of nonamyloidogenic and bioactive human islet amyloid polypeptide (IAPP) as nanomolar affinity inhibitor of IAPP cytotoxic fibrillogenesis. Proc Natl Acad Sci U S A. 2006;103:2046–2051
  23. Konno K, Hirayama C, Yasui H, Nakamura M. Enzymatic activation of oleuropein: a protein crosslinker used as chemical defence by privet tree. Proc Natl Acad Sci U S A. 1999;96:9159–9162
  24. Bucciantini M, Giannoni E, Chiti F, Baroni F, Formigli L, Zurdo J, et al. Inherent toxicity of aggregates implies a common mechanism for protein misfolding diseases. Nature. 2002;416:507–511
  25. Kayed R, Bernhagen J, Greenfield N, Sweimeh KM, Brunner H, Voelter W, et al. Conformational transitions of islet amyloid polypeptide (IAPP) in amyloid formation in vitro. J Mol Biol. 1999;287:781–796
  26. Porat Y, Mazor Y, Efrat S, Gazit E. Inhibition of islet amyloid polypeptide fibril formation: a potential role for heteroaromatic interactions. Biochemistry. 2004;43:14454–14462
  27. Bucciantini M, Rigacci S, Berti A, Pieri L, Cecchi C, Nosi D, et al. Patterns of cell death triggered in two different cell lines by HypF-N pre-fibrillar aggregates. FASEB J. 2005;19:437–449
  28. Engel MFM, Khemtémourian L, Kleijer CC, Meeldijk HJD, Jacobs J, Verkleij AJ, et al. Membrane damage by human islet amyloid polypeptide through fibril growth at the membrane. Proc Natl Acad Sci U S A. 2008;105:6033–6048
  29. LeVine H. Quantification of beta-sheet amyloid fibril structures with Thioflavine T. Methods Enzymol. 1999;309:274–284
  30. Khemtémourian L, Killian JA, Höppener JWM, Engel MFM. Recent insight in Islet amyloid polypeptide-induced membrane disruption and its role in β-cell death in Type 2 diabetes mellitus. Exp Diabetes Res. 2008;Article ID 421287
  31. Cerdà-Costa N, Esteras-Chopo A, Aviles FX, Serrano L, Villegas V. Early kinetics of amyloid fibril formation reveals conformational reorganisation of initial aggregates. J Mol Biol. 2007;366:1351–1353
  32. Rigacci S, Bucciantini M, Relini A, Pesce A, Gliozzi A, Berti A, et al. The (1-63) region of the p53 transactivation domain aggregates in vitro into cytotoxic amyloid assemblies. Biophys J. 2008;94:3635–3646
  33. Porat Y, Abramowitz A, Gazit E. Inhibition of amyloid fibril formation by polyphenols: structural similarity and aromatic interactions as a common inhibition mechanism. Chem Biol Drug Des. 2006;67:27–37
  34. Visioli F, Bellomo G, Galli C. Free radical-scavenging properties of olive oil polyphenols. Biochem Biophys Res Commun. 1998;247:60–64
  35. Mishra R, Sellin D, Radovan D, Gohlke A, Winter R. Inhibiting islet amyloid polypeptide fibril formation by the red wine compound resveratrol. Chembiochem. 2009;10:445–449
  36. Tracz SM, Abedini A, Driscoll M, Raleigh DP. Role of aromatic interactions in amyloid formation by peptides derived from human amylin. Biochemistry. 2004;43:15901–15908
  37. Vissers MN, Zock PL, Roodengburg AJC, Leenen R, Katan MB. Olive oil phenols are adsorbed in humans. J Nutr. 2002;132:409–417
  38. Corona G, Tzounis X, Dessì MA, Deiana M, Debnam ES, Visioli F, et al. The fate of olive oil polyphenols in the gastrointestinal tract: implications of gastric and colonic microflora-dependent biotransformation. Free Radic Res. 2006;40:647–658

 This work was supported by a grant from the Ente Cassa di Risparmio di Firenze and from the Italian MIUR (grant n. 2007XY59ZJ_001).

PII: S0955-2863(09)00100-4

doi: 10.1016/j.jnutbio.2009.04.010

The Journal of Nutritional Biochemistry
Volume 21, Issue 8 , Pages 726-735 , August 2010