Investigation of interfacial behavior of glycyrrhizin with a lipid raft model via a Langmuir monolayer study

Biochimica et Biophysica Acta - Biomembranes

Volumn 1828, Issue 4, 2013, Pages 1271-1283

  Sakamoto, Seiichi ^a   Nakahara, Hiromichi ^a   Uto, Takuhiro ^a   Shoyama, Yukihiro ^a   Shibata, Osamu ^a  

^a NAGASAKI INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

Glycyrrhizin; Langmuir monolayer; Lipid raft; Membrane disruption; Saponin

Indexed keywords

CHOLESTEROL; DIOLEOYLPHOSPHATIDYLCHOLINE; GLYCYRRHIZIC ACID; N PALMITOYL DEXTRO ERYTHRO SPHINGOSYLPHOSPHORYLCHOLINE; PHOSPHATIDYLCHOLINE; SAPONIN; SPHINGOMYELIN; UNCLASSIFIED DRUG;

ARTICLE; BREWSTER ANGLE MICROSCOPY; CELL MEMBRANE; CELL STRUCTURE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DESORPTION; FLUORESCENCE MICROSCOPY; GLYCYRRHIZA; HYDROGEN BOND; ISOTHERM; LANGMUIR BLODGETT FILM; LIPID MONOLAYER; LIPID RAFT; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN LIPID INTERACTION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; SURFACE PROPERTY; SURFACE TENSION; THERMODYNAMICS;

CHOLESTEROL; GLYCYRRHIZIC ACID; MEMBRANE MICRODOMAINS; MICROSCOPY, FLUORESCENCE; PHOSPHATIDYLCHOLINES; PHOSPHORYLCHOLINE; SPHINGOSINE;

EID: 84874376715     PISSN: 00052736     EISSN: 18792642     Source Type: Journal    
DOI: 10.1016/j.bbamem.2013.01.006     Document Type: Article

References (76)

1. I. Fuyuno Will the sun set on Kampo? Nature 480 2011 S96
2. H. Hayashi, and H. Sudo Economic importance of licorice Plant Biotechnol. 26 2009 101 104
3. T.G.J.V. Rossum, A.G. Vulto, R.A.D. Man, J.T. Brouwer, and S.W. Schalm Glycyrrhizin as a potential treatment for chronic hepatitis C Aliment. Pharmacol. Ther. 12 1998 199 205 (Pubitemid 28160013)
4. H. Akamatsu, J. Komura, Y. Asada, and Y. Niwa Mechanism of anti-inflammatory action of glycyrrhizin: effect on neutrophil functions including reactive oxygen species generation Planta Med. 57 1991 119 121
5. S. Amagaya, E. Sugishita, Y. Ogihara, S. Ogawa, K. Okada, and T. Aizawa Comparative studies of the stereoisomers of glycyrrhetinic acid on anti-inflammatory activities J. Pharmacobiodyn. 7 1984 923 928 (Pubitemid 15174849)
6. D. Steinberg, H.D. Sgan-Cohen, A. Stabholz, S. Pizanty, R. Segal, and M.N. Sela The anticariogenic activity of glycyrrhizin: preliminary clinical trials Isr. J. Dent. Sci. 2 1989 153 157
7. S. Thirugnanam, L. Xu, K. Ramaswamy, and M. Gnanasekar Glycyrrhizin induces apoptosis in prostate cancer cell lines DU-145 and LNCaP Oncol. Rep. 20 2008 1387 1392
8. J. Cinatl, B. Morgenstern, G. Bauer, P. Chandra, H. Rabenau, and H.W. Doerr Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus Lancet 361 2003 2045 2046 (Pubitemid 36695048)
9. R. Pompei, O. Flore, M.A. Marccialis, A. Pani, and B. Loddo Glycyrrhizic acid inhibits virus growth and inactivates virus particles Nature 281 1979 689 690 (Pubitemid 10249050)
10. T. Hattori, S. Ikematsu, A. Koito, S. Matsushita, Y. Maeda, M. Hada, M. Fujimaki, and K. Takatsuki Preliminary evidence for inhibitory effect of glycyrrhizin on HIV replication in patients with AIDS Antiviral Res. 11 1989 255 261
11. M. Ito, A. Sato, K. Hirabayashi, F. Tanabe, S. Shigeta, M. Baba, E. De Clercq, H. Nakashima, and N. Yamamoto Mechanism of inhibitory effect of glycyrrhizin on replication of human immunodeficiency virus (HIV) Antiviral Res. 10 1988 289 298 (Pubitemid 19073538)
12. A. Wolkerstorfer, H. Kurz, N. Bachhofner, and O.H.J. Szolar Glycyrrhizin inhibits influenza A virus uptake into the cell Antiviral Res. 83 2009 171 178
13. J.-M. Crance, F. Lévêque, E. Biziagos, H. van Cuyck-Gandré, A. Jouan, and R. Deloince Studies on mechanism of action of glycyrrhizin against hepatitis a virus replication in vitro Antiviral Res. 23 1994 63 76 (Pubitemid 24021216)
14. H. Suzuki, Y. Ohta, T. Takino, K. Fujisawa, and C. Hirayama Effects of glycyrrhizin on biochemical tests in patients with chronic hepatitis-double blind trial Asian Med. J. 26 1983 423 438 (Pubitemid 14210247)
15. A. Tahara, T. Nakata, and Y. Ohtsuka New type of compound with strong sweetness Nature 233 1971 619 620
16. M. Kondo, H. Minamino, G. Okuyama, K. Honda, H. Nagasawa, and Y. Otani Physicochemical properties and applications of α- and β-glycyrrhizins natural surface active agents in licorice root extract J. Soc. Cosmet. Chem. 37 1986 177 189
17. A. Otsuka, Y. Yonezawa, K. Iba, T. Tatsumi, and H. Sunada Physico-chemical properties of glycyrrhizic acid in aqueous media. I. Surface-active properties and formation of molecular aggregates Yakugaku Zasshi 96 1976 203 208
18. A. Otsuka, Y. Yonezawa, and Y. Nakamura Physico-chemical properties of glycyrrhizic acid in aqueous media. II. Effect on flocculation-deflocculation behavior of suspensions of sulfathiazole and graphite J. Pharm. Sci. 67 1978 151 154 (Pubitemid 8309075)
19. Y. Yonezawa, and A. Otsuka Physico-chemical properties of glycyrrhizic acid in aqueous media. III. Solubilizing properties for dyes and medicinal substance YAKUGAKU ZASSHI 101 1981 829 835 (Pubitemid 12219465)
20. E. Azaz, and R. Segal Glycyrrhizin as gelling agents Pharm. Acta Helv. 55 1980 183 186
21. K. Simons, and E. Ikonen Functional rafts in cell membranes Nature 387 1997 569 572 (Pubitemid 27248754)
22. K. Simons, and D. Toomre Lipid rafts and signal transduction Nat. Rev. Mol. Cell Biol. 1 2000 31 39
23. D.A. Brown Seeing is believing: visualization of rafts in model membranes Proc. Natl. Acad. Sci. 98 2001 10517 10518 (Pubitemid 32878648)
24. J.H. Ipsen, G. Karlstrom, O.G. Mouritsen, H. Wennerstrom, and M.J. Zuckermann Phase equilibria in the phosphatidylcholine-cholesterol system Biochim. Biophys. Acta 905 1987 162 172
25. D.J. Recktenwald, and H.M. McConnell Phase equilibria in binary mixtures of phosphatidylcholine and cholesterol Biochemistry 20 1981 4505 4510
26. M.B. Sankaram, and T.E. Thompson Interaction of cholesterol with various glycerophospholipids and sphingomyelin Biochemistry 29 1990 10670 10675
27. S. Munro Lipid rafts: elusive or illusive? Cell 115 2003 377 388 (Pubitemid 37456801)
28. A. Radhakrishnan, and H.M. McConnell Cholesterol-phospholipid complexes in membranes J. Am. Chem. Soc. 121 1999 486 487
29. J.C. Lawrence, D.E. Saslowsky, J. Michael Edwardson, and R.M. Henderson Real-time analysis of the effects of cholesterol on lipid raft behavior using atomic force microscopy Biophys. J. 84 2003 1827 1832 (Pubitemid 36322944)
30. N. Periasamy, H. Teichert, K. Weise, R.F. Vogel, and R. Winter Effects of temperature and pressure on the lateral organization of model membranes with functionally reconstituted multidrug transporter LmrA Biochim. Biophys. Acta 1788 2009 390 401
31. H.A. Rinia, M.M.E. Snel, J.P.J.M. van der Eerden, and B. de Kruijff Visualizing detergent resistant domains in model membranes with atomic force microscopy FEBS Lett. 501 2001 92 96 (Pubitemid 33712494)
32. C. Yuan, J. Furlong, P. Burgos, and L.J. Johnston The size of lipid rafts: an atomic force microscopy study of ganglioside GM1 domains in sphingomyelin/DOPC/cholesterol membranes Biophys. J. 82 2002 2526 2535 (Pubitemid 34441292)
33. K. Ha̧c-Wydr, P. Dynarowicz-Ła̧tka, P. Wydro, and K. Ba̧k Edelfosine disturbs the sphingomyelin-cholesterol model membrane system in a cholesterol-dependent way-the Langmuir monolayer study Colloids Surf. B: Biointerfaces 88 2011 635 640
34. E. Prenner, G. Honsek, D. Hönig, D. Möbius, and K. Lohner Imaging of the domain organization in sphingomyelin and phosphatidylcholine monolayers Chem. Phys. Lipids 145 2007 106 118 (Pubitemid 46080418)
35. K. Bacia, D. Scherfeld, N. Kahya, and P. Schwille Fluorescence correlation spectroscopy relates rafts in model and native membranes Biophys. J. 87 2004 1034 1043 (Pubitemid 39095082)
36. T. Baumgart, S.T. Hess, and W.W. Webb Imaging coexisting fluid domains in biomembrane models coupling curvature and line tension Nature 425 2003 821 824 (Pubitemid 37351463)
37. R.F.M. de Almeida, J. Borst, A. Fedorov, M. Prieto, and A.J.W.G. Visser Complexity of lipid domains and rafts in giant unilamellar vesicles revealed by combining imaging and microscopic and macroscopic time-resolved fluorescence Biophys. J. 93 2007 539 553 (Pubitemid 47057819)
38. J. Juhasz, F.J. Sharom, and J.H. Davis Quantitative characterization of coexisting phases in DOPC/DPPC/cholesterol mixtures: comparing confocal fluorescence microscopy and deuterium nuclear magnetic resonance Biochim. Biophys. Acta 1788 2009 2541 2552
39. M.T. Stöckl, and A. Herrmann Detection of lipid domains in model and cell membranes by fluorescence lifetime imaging microscopy Biochim. Biophys. Acta 1798 2010 1444 1456
40. S.L. Veatch, I.V. Polozov, K. Gawrisch, and S.L. Keller Liquid domains in vesicles investigated by NMR and fluorescence microscopy Biophys. J. 86 2004 2910 2922 (Pubitemid 38552695)
41. G. Wheeler, and K.M. Tyler Widefield microscopy for live imaging of lipid domains and membrane dynamics Biochim. Biophys. Acta 1808 2011 634 641
42. T. Nakamura, T. Fujii, and A. Ichihara Enzyme leakage due to change of membrane permeability of primary cultured rat hepatocytes treated with various hepatotoxins and its prevention by glycyrrhizin Cell. Biol. Toxicol. 1 1985 285 295 (Pubitemid 16257883)
43. S. Harada The broad anti-viral agent glycyrrhizin directly modulates the fluidity of plasma membrane and HIV-1 envelope Biochem. J. 392 2005 191 199 (Pubitemid 41689415)
44. A.D. Bangham, R.W. Horne, A.M. Glauert, J.T. Dingle, and J.A. Lucy Action of saponin on biological cell membranes Nature 196 1962 952 955
45. E. Baumann, G. Stoya, A. Völkner, W. Richter, C. Lemke, and W. Linss Hemolysis of human erythrocytes with saponin affects the membrane structure Acta Histochem. 102 2000 21 35 (Pubitemid 30120643)
46. M. Chwalek, N. Lalun, H. Bobichon, K. Plé, and L. Voutquenne-Nazabadioko Structure-activity relationships of some hederagenin diglycosides: haemolysis, cytotoxicity and apoptosis induction Biochim. Biophys. Acta 1760 2006 1418 1427 (Pubitemid 44389805)
47. R.R. Dourmashkin, R.M. Dougherty, and R.J. Harris Electron microscopic observations on Rous sarcoma virus and cell membranes Nature 194 1962 1116 1119
48. P. Seeman, D. Cheng, and G.H. Iles Structure of membrane holes in osmotic and saponin hemolysis J. Cell. Biol. 56 1973 519 527
49. C.N. Armah, A.R. Mackie, C. Roy, K. Price, A.E. Osbourn, P. Bowyer, and S. Ladha The membrane-permeabilizing effect of avenacin A-1 involves the reorganization of bilayer cholesterol Biophys. J. 76 1999 281 290 (Pubitemid 29202456)
50. E.A.J. Keukens, T. de Vrije, C. van den Boom, P. de Waard, H.H. Plasman, F. Thiel, V. Chupin, W.M.F. Jongen, and B. de Kruijff Molecular basis of glycoalkaloid induced membrane disruption Biochim. Biophys. Acta 1240 1995 216 228 (Pubitemid 26005549)
51. F. Lin, and R. Wang Hemolytic mechanism of dioscin proposed by molecular dynamics simulations J. Mol. Model. 16 2010 107 118
52. H. Nakahara, O. Shibata, and Y. Moroi Examination of surface adsorption of cetyltrimethylammonium bromide and sodium dodecyl sulfate J. Phys. Chem. B 115 2011 9077 9086
53. C.L. Wennberg, D. van der Spoel, and J.S. Hub Large influence of cholesterol on solute partitioning into lipid membranes J. Am. Chem. Soc. 134 2012 5351 5361
54. R. Maget-Dana The monolayer technique: a potent tool for studying the interfacial properties of antimicrobial and membrane-lytic peptides and their interactions with lipid membranes Biochim. Biophys. Acta 1462 1999 109 140
55. V. Vogel, and D. Möbius Local surface potentials and electric dipole moments of lipid monolayers: contributions of the water/lipid and the lipid/air interfaces J. Colloid Interface Sci. 126 1988 408 420
56. M.L. Fanani, and B. Maggio Liquid-liquid domain miscibility driven by composition and domain thickness mismatch in ternary lipid monolayers L. Phys. Chem. B 115 2011 41 49
57. H. Brockman Dipole potential of lipid membranes Chem. Phys. Lipids 37 1994 57 79 (Pubitemid 24299188)
58. S.A. Simon, and T.J. McIntosh Magnitude of the solvation pressure depends on dipole potential Proc. Natl. Acad. Sci. U. S. A. 86 1989 9263 9267 (Pubitemid 20010405)
59. H. Nakahara, S. Lee, M.P. Krafft, and O. Shibata Fluorocarbon-hybrid pulmonary surfactants for replacement therapy - a Langmuir monolayer study Langmuir 26 2010 18256 18265
60. G.L. Gaines Jr. Insoluble Monolayers at Liquid-Gas Interfaces 1966 Interscience New York 288
61. J. Marsden, and J.H. Schulman Molecular interaction in monolayers Trans. Faraday Soc. 34 1938 748 758
62. D.O. Shah, and J.H. Schulman Influence of calcium, cholesterol, and unsaturation on lecithin monolayers J. Lipid Res. 8 1967 215 226
63. P. Dynarowicz-Łatka, and K. Ha̧c-Wydro Interactions between phosphatidylcholines and cholesterol in monolayers at the air/water interface Colloids Surf. B: Biointerfaces 37 2004 21 25 (Pubitemid 39164190)
64. P. Wydro, S. Knapczyk, and M. Lapczyńska Variations in the condensing effect of cholesterol on saturated versus unsaturated phosphatidylcholines at low and high sterol concentration Langmuir 27 2011 5433 5444
65. Y. Barenholz, and T.E. Thompson Sphingomyelins in bilayers and biological membranes Biochim. Biophys. Acta 604 1980 129 158
66. A. Björkbom, T. Róg, P. Kankaanpää, D. Lindroos, K. Kaszuba, M. Kurita, S. Yamaguchi, T. Yamamoto, S. Jaikishan, L. Paavolainen, J. Päivärinne, T.K.M. Nyholm, S. Katsumura, I. Vattulainen, and J.P. Slotte N- and O-methylation of sphingomyelin markedly affects its membrane properties and interactions with cholesterol Biochim. Biophys. Acta 1808 2011 1179 1186
67. H. Yokoyama, H. Nakahara, T. Nakagawa, S. Shimono, K. Sueishi, and O. Shibata Miscibility behavior of two-component monolayers at the air-water interface: perfluorocarboxylic acids and DMPE J. Colloid Interface Sci. 337 2009 191 200
68. H. Nakahara, M.P. Krafft, A. Shibata, and O. Shibata Interaction of a partially fluorinated alcohol (F8H11OH) with biomembrane constituents in two-component monolayers Soft Matter 7 2011 7325 7333
69. P. Joos, and R.A. Demel The interaction energies of cholesterol and lecithin in spread mixed monolayers at the air-water interface Biochim. Biophys. Acta 183 1969 447 457
70. L.J. Pike, X. Han, K.-N. Chung, and R.W. Gross Lipid rafts are enriched in arachidonic acid and plasmenylethanolamine and their composition is independent of caveolin-1 expression: a quantitative electrospray ionization/mass spectrometric analysis Biochemistry 41 2002 2075 2088 (Pubitemid 34132282)
71. R.A. Demel, W.S.M. Geurts Van Kessel, R.F.A. Zwaal, B. Roelofsen, and L.L.M. Van Deenen Biochim. Biophys. Acta 406 1975 97 107
72. R.A. Demel Monomolecular layers in the study of biomembranes Subcell. Biochem. 23 1994 83 120
73. D. Marsh Lateral pressure in membranes Biochim. Biophys. Acta 1286 1996 183 223 (Pubitemid 26426521)
74. R.F.M. de Almeida, A. Fedorov, and M. Prieto Sphingomyelin/ phosphatidylcholine/cholesterol phase diagram: boundaries and composition of lipid rafts Biophys. J. 85 2003 2406 2416 (Pubitemid 37210789)
75. O.Y. Gluschenko, N.E. Polyakov, and T.V. Leshina NMR relaxation study of cholesterol binding with plant metabolites Appl. Magn. Reson. 41 2011 283 294
76. J.M. Augustin, V. Kuzina, S.B. Andersen, and S. Bak Molecular activities, biosynthesis and evolution of triterpenoid saponins Phytochemistry 72 2011 435 457