Interaction between Plectranthus barbatus herbal tea components and acetylcholinesterase: Binding and activity studies

Food and Function

Volumn 3, Issue 11, 2012, Pages 1176-1184

  Falé, Pedro L V ^a   Ascensão, Lia ^a   Serralheiro, M Luisa ^a   Haris, Parvez I ^b  

^a UNIVERSITY OF LISBON   (Portugal)

^b DE MONTFORT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ASSOCIATION REACTIONS; BRAIN; DEUTERIUM; FLAVONOIDS; HYDROGEN BONDS; PHENOLS; PLANT EXTRACTS;

ACETYLCHOLINESTERASE; ACETYLCHOLINESTERASE ACTIVITY; ACETYLCHOLINESTERASE INHIBITION; AMINO ACID RESIDUES; FTIR ANALYSIS; HYDROGEN-DEUTERIUM EXCHANGE; HYDROPHOBIC ASSOCIATION; INHIBITOR MOLECULES; INTERMOLECULAR INTERACTIONS; INTRAPERITONEAL ADMINISTRATION; PHENOLIC COMPOUNDS; SECONDARY STRUCTURES; SOLVENT ACCESSIBILITY; SPECTROSCOPIC DATA; STRUCTURAL FEATURE; THERMODYNAMIC PARAMETER; WATER EXTRACTS;

ENZYME INHIBITION;

PLECTRANTHUS; PLECTRANTHUS BARBATUS; RATTUS;

ACETYLCHOLINESTERASE; ANTIOXIDANT; CHOLINESTERASE INHIBITOR; FLAVONOID; PLANT EXTRACT;

ARTICLE; BEVERAGE; BINDING SITE; CHEMICAL PHENOMENA; CHEMISTRY; HYDROGEN BOND; INFRARED SPECTROSCOPY; METABOLISM; PLECTRANTHUS; PROTEIN SECONDARY STRUCTURE; THERMODYNAMICS;

ACETYLCHOLINESTERASE; ANTIOXIDANTS; BEVERAGES; BINDING SITES; CHOLINESTERASE INHIBITORS; FLAVONOIDS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; PLANT EXTRACTS; PLECTRANTHUS; PROTEIN STRUCTURE, SECONDARY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 84872166906     PISSN: 20426496     EISSN: 2042650X     Source Type: Journal    
DOI: 10.1039/c2fo30032j     Document Type: Article

References (36)

1. M. Heinrich H. L. Teoh Galanthamine from snowdrop - the development of a modern drug against Alzheimer's disease from local Caucasian knowledge J. Ethnopharmacol. 2004 92 147 162 (Pubitemid 38610095)
2. M. Harel L. K. Sonoda I. Silman J. L. Sussman T. L. Rosenberry Crystal structure of thioflavin T bound to the peripheral site of Torpedo californica acetylcholinesterase reveals how thioflavin T acts as a sensitive fluorescent reporter of ligand binding to the acylation site J. Am. Chem. Soc. 2008 130 7856 7861 (Pubitemid 351875060)
3. M. Shinitzky Y. Dudai I. Silman Spectral evidence for the presence of tryptophan in the binding site of acetylcholinesterase FEBS Lett. 1973 30 125 128
4. J. R. Lakowicz, in Principles of Fluorescence Spectroscopy, Springer, New York, 3rd edn, 2006, ch. 8, pp. 278-292
5. P. Taylor S. Lappi Interaction of fluorescence probes with acetylcholinesterase. The site and specificity of propidium binding Biochemistry 1975 14 1989 1997
6. D. J. Epstein H. A. Berman P. Taylor Ligand-induced conformational changes in acetylcholinesterase investigated with fluorescent phosphonates Biochemistry 1979 18 4749 4754
7. P. K. Mukjerjee V. Kumar M. Mal P. J. Houghton Acetylcholinesterase inhibitors from plants Phytomedicine 2007 14 289 300 (Pubitemid 46415622)
8. P. L. Falé C. Borges P. J. A. Madeira L. Ascensão M. E. M. Araújo M. H. Florêncio M. L. M. Serralheiro Rosmarinic acid, scutellarein 40-methyl ether 7-O-glucuronide and (16S)-coleon E are the main compounds responsible for the antiacetylcholinesterase and antioxidant activity in herbal tea of Plectranthus barbatus ("falso boldo") Food Chem. 2009 114 798 805
9. S. Porfírio P. L. V. Falé P. J. A. Madeira M. H. Florêncio L. Ascensão M. L. M. Serralheiro Antiacetylcholinesterase and antioxidant activities of Plectranthus barbatus tea, after in vitro gastrointestinal metabolism Food Chem. 2010 122 179 187
10. P. L. V. Falé P. J. A. Madeira M. H. Florêncio L. Ascensão M. L. M. Serralheiro Function of Plectranthus barbatus herbal tea as neuronal acetylcholinesterase inhibitor Food Funct. 2011 2 130 136
11. I. Erlung Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability, and epidemiology Nutr. Res. 2004 24 851 874
12. J. R. Lakowicz G. Weber Quenching of fluorescence by oxygen. Probe for structural fluctuations in macromolecules Biochemistry 1973 12 4161 4170
13. J. Jin X. Zhang Spectrophotometric studies on the interaction between pazufloxacin mesilate and human serum albumin or lysozyme J. Lumin. 2008 128 81 86 (Pubitemid 47374181)
14. Y. Yang Q. Hua Y. Fan H. Shen Study on the binding of luteolin to bovine serum albumin Spectrochim. Acta, Part A 2008 69 432 436 (Pubitemid 351172902)
15. P. D. Ross S. Subramanian Thermodynamics of protein association reactions: forces contributing to stability Biochemistry 1981 20 3096 3102
16. P. I. Haris F. Severcan FTIR spectroscopic characterization of protein structure in aqueous and non-aqueous media J. Mol. Catal. B: Enzym. 1999 7 207 221 (Pubitemid 29408531)
17. J. Xiao M. Suzuki X. Jiang X. Chen K. Yamamoto F. Ren M. Xu Influence of B-ring hydroxylation on interactions of flavonols with bovine serum albumin J. Agric. Food Chem. 2008 56 2350 2356 (Pubitemid 351570424)
18. R. Tantipolphan T. Rades A. J. McQuillan N. J. Medlicott Adsorption of bovine serum albumin (BSA) onto lecithin studied by attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy Int. J. Pharm. 2007 337 40 47 (Pubitemid 46756032)
19. W. He Y. Li J. Tang F. Luan J. Jin Z. Hu Comparison of the characterization on binding of alpinetin and cardamonin to lysozyme by spectroscopic methods Int. J. Biol. Macromol. 2006 39 165 173 (Pubitemid 44602201)
20. P. I. Haris D. C. Lee D. Chapman A Fourier transform infrared investigation of the structural differences between ribonuclease A and ribonuclease S Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1986 874 255 265
21. M. Jackson P. I. Haris D. Chapman Fourier transform infrared spectroscopic studies of calcium-binding proteins Biochemistry 1991 30 9681 9686
22. U. Gorne-Tschelnokow D. Naumann C. Weise F. Hucho Secondary structure and temperature behaviour of acetylcholinesterase studies by Fourier-transform infrared spectroscopy Eur. J. Biochem. 1993 213 1235 1242 (Pubitemid 23152234)
23. Y. Bourne J. Grassi P. E. Bougis P. Marchot Conformational flexibility of the acetylcholinesterase tetramer suggested by X-ray crystallography J. Biol. Chem. 1999 274 30370 30376
24. A. Hvidt K. Wallevik Conformational changes in human serum albumin as revealed by hydrogen-deuterium exchange studies J. Biol. Chem. 1972 247 1530 1535
25. D. J. Hartshorne A. Stracher Deuterium-hydrogen exchange of muscle proteins Biochemistry 1965 4 1917 1923
26. R. Z. Cer U. Mudunuri R. Stephens F. J. Lebeda IC50-to-K i: a web-based tool for converting IC50 to Ki values for inhibitors of enzyme activity and ligand binding Nucleic Acids Res. 2009 37 W441 W445
27. M. T. H. Khan I. Orhan F. S. Senol M. Kartal B. Sener M. Dvorska K. Smejkal T. Slapetova Cholinesterase inhibitory activities of some flavonoid derivatives and chosen xanthone and their molecular docking studies Chem.-Biol. Interact. 2009 181 383 389
28. R. Sheng X. Lin J. Zhang K. S. Chol W. Huang B. Yang Q. He Y. Hu Design, synthesis and evaluation of flavonoid derivatives as potent AChE inhibitors Bioorg. Med. Chem. 2009 17 6692 6698
29. Y. Bourne Z. Radić P. Taylor P. Marchot Conformational remodeling of femtomolar inhibitor - acetylcholinesterase complexes in the crystalline state J. Am. Chem. Soc. 2010 132 18292 18300
30. B. Sanson J. P. Colletier Y. Xu P. T. Lang H. Jiang I. Silman J. L. Sussman M. Weik Backdoor opening mechanism in acetylcholinesterase based on X-ray crystallography and molecular dynamics simulations Protein Sci. 2011 20 1114 1118
31. M. Harel I. Schalk L. Ehret-Sabatier F. Bouet M. Goeldner C. Hirth P. H. Axelsen I. Silman J. L. Sussman Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase Proc. Natl. Acad. Sci. U. S. A. 1993 90 9031 9035 (Pubitemid 23306445)
32. J. Sebestík S. M. Marques P. L. Falé S. Santos D. M. Arduíno S. M. Cardoso C. R. Oliveira M. L. Serralheiro M. A. Santos Bifunctional phenolic-choline conjugates as anti-oxidants and acetylcholinesterase inhibitors J. Enzyme Inhib. Med. Chem. 2011 26 485 497
33. H.-F. Ji H.-Y. Zhang Theoretical evaluation of flavonoids as multipotent agents to combat Alzheimer's disease THEOCHEM 2006 767 3 9
34. K. Ingkaninan P. Temkitthawon K. Chuenchon T. Yuyaem W. Thongnoi Screening for acetylcholinesterase inhibitory activity in plants used in Thai traditional rejuvenating and neurotonic remedies J. Ethnopharmacol. 2003 89 261 264 (Pubitemid 37378200)
35. M. Kubista R. Sjoback S. Eriksson B. Albinsson Experimental correction for the inner-filter effect in fluorescence spectra Analyst 1994 119 417 419
36. P. I. Haris D. Chapman R. A. Harrison K. F. Smith S. J. Perkins Conformational transition between native and reactive center cleaved forms of α1-antitrypsin by Fourier transform infrared spectroscopy and small-angle neutron scattering Biochemistry 1990 29 1377 1380 (Pubitemid 20063364)