Monolayer membranes and bilayer vesicles characterized by α- and β-anomer of sulfoquinovosyldiacyglycerol (SQDG)

Chemistry and Physics of Lipids

Volumn 133, Issue 2, 2005, Pages 203-214

  Matsumoto, Kenjiro ^a   Sakai, Hideki ^a   Ohta, Keisuke ^a   Kameda, Hiroshi ^a   Sugawara, Fumio ^a   Abe, Masahiko ^a   Sakaguchi, Kengo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Bilayer; Cholesterol; Head group; Monolayer; Stereochemistry; Sulfolipid; Vesicle

Indexed keywords

DIACYLGLYCEROL DERIVATIVE;

ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; ENTHALPY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID BILAYER; LIPID MEMBRANE; LIPID MONOLAYER; LIPID VESICLE; MICROSCOPY; PHASE TRANSITION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; TEMPERATURE; TURBIDITY;

CALORIMETRY, DIFFERENTIAL SCANNING; CHOLESTEROL; GLYCOLIPIDS; LIPID BILAYERS; LIPOSOMES; MOLECULAR CONFORMATION; NEPHELOMETRY AND TURBIDIMETRY; PHASE TRANSITION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SURFACE PROPERTIES; TEMPERATURE;

EID: 11844280854     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2004.10.004     Document Type: Article

References (46)

1. B. Asgharian, and D.A. Cadenhead A comparative monomolecular film study of 1,2-di-O-palmitoyl-3-O-(α- and β-d-glucopyranosyl)-sn-glycerols Biochemistry 28 1989 7102 7106
2. A.D. Bangham, M.M. Standish, and J.C. Watkins Diffusion of univalent ions across the lamellae of swollen phospholipids J. Mol. Biol. 13 1965 238 252
3. J. Barber, and K. Gounaris What role does sulfolipid play within the thylakoid membrane Photosynth. Res. 9 1986 239 249
4. C. Benning Biosynthesis and function of the sulfolipid sulfoquinovosyl diacylglycerol Annu. Rev. Plant Physiol. Plant Mol. Biol. 49 1998 53 75
5. J.P. Berge, E. Debiton, J. Dumay, P. Durand, and C. Barthomeuf In vitro anti-inflammatory and anti-proliferative activity of sulfolipids from the red alga Porphyridium crurentum J. Agric. Food Chem. 50 2002 6227 6232
6. C. Bernsdorff, A. Wolf, R. Winter, and E. Gratton Effect of hydrostatic pressure on water penetration and rotational dynamics in phospholipids- cholesterol bilayers Biophys. J. 72 1997 1264 1277
7. D.G. Bishop, J.R. Kenrick, J.H. Bayston, A.S. Macpherson, and S.R. Johns Monolayer properties of chloroplast lipids Biochim. Biophys. Acta 602 1980 248 259
8. A. Blume A comparative study of the phase transitions of phospholipid bilayers and monolayers Biochim. Biophys. Acta 557 1979 32 44
9. J.M. Boggs Lipid intermolecular hydrogen bonding: influence on structural organization and membrane function Biochim. Biophys. Acta 906 1987 353 404
10. R.A. Cedergren, and R.I. Hollingsworth Occurrence of sulfoquinovosyl diacylglycerol in some members of the family Rhizobiaceae J. Lipid Res. 35 1994 1452 1461
11. G. Cevc, and D. Marsh Phospholipid Bilayers 1987 John Wiley & Sons New York
12. J. Golik, J.K. Dickey, G. Todderud, D. Lee, J. Alford, S. Huang, S. Klohr, D. Eustice, A. Aruffo, and M.L. Agler Isolation and structure determination of sulfonoquinovosyl dipalmitoyl glyceride, a P-selectin receptor inhibitor from the alga Dictyochloris fragrans J. Nat. Prod. 60 1997 387 389
13. S. Güler, A. Seeliger, H. Härtel, G. Renger, and C. Benning A Null mutant of Synechococus sp. PCC7942 deficient in the sulfolipid sulfoquinovosyl diacylglycerol J. Biol. Chem. 271 1996 7501 7507
14. K.R. Gustafson, J.H Cardellina II., R.W. Fuller, O.S. Weislow, R.F. Kiser, K.M. Snader, G.M.L. Patterson, and M.R. Boyd AIDS-antiviral sulfolipids from cyanobacteria (blue-green algae) J. Natl. Cancer Inst. 81 1989 1254 1258
15. S. Hanashima, Y. Mizushina, K. Ohta, T. Yamazaki, F. Sugawara, and K. Sakaguchi Structure-activity relationship of a novel group of mammalian DNA polymerase inhibitors, synthetic sulfoquinovosylacylglycerols Jpn. J. Cancer Res. 91 2000 1073 1083
16. S. Hanashima, Y. Mizushina, T. Yamazaki, K. Ohta, S. Takahashi, H. Koshino, H. Sahara, K. Sakaguchi, and F. Sugawara Structural determination of sulfoquinovosyldiacylglycerol by chiral syntheses Tetrahedron Lett. 41 2000 4403 4407
17. S. Hanashima, Y. Mizushina, T. Yamazaki, K. Ohta, S. Takahashi, H. Sahara, K. Sakaguchi, and F. Sugawara Synthesis of sulfoquinovosylacylglycerols, inhibitors of eukaryotic DNA polymerase α and β Bioorg. Med. Chem. 9 2001 367 376
18. K.P. Howard, and J.H. Prestegard Conformation of sulfoquinovosyldiacylglycerol bound to a magnetically oriented membrane system Biophys. J. 71 1996 2573 2582
19. H.C. Jarrell, A.J. Wand, J.B. Giziewicz, and I.C.P. Smith The dependence of glyceroglycolipid orientation and dynamics on head-group structure Biochim. Biophys. Acta 897 1987 69 82
20. 2H NMR study of head group orientation, ordering, and effects on lipid aggregate structure Biochemistry 25 1986 3950 3957
21. Y.H. Kim, J.S. Yoo, and M.S. Kim Structural characterization of sulfoquinovosyl, monogalactosyl and digalactosyl diacylglycerols by FAB-CID-MS/MS J. Mass Spectrom. 32 1997 968 977
22. B.D. Ladbrooke, R.M. Williams, and D. Chaoman Studies on lecithin-cholesterol-water interactions by differential scanning calorimetry and X-ray diffraction Biochim. Biophys. Acta 150 1968 333 340
23. S. Loya, V. Reshef, E. Mizrachi, C. Silberstein, Y. Rachamim, S. Carmeli, and A. Hizi The inhibition of the reverse transcriptase of HIV-1 by the natural sulfoglycolipids from cyanobacteria: contribution of different moieties to their high potency J. Nat. Prod. 61 1998 891 895
24. S. Lund-Katz, H.M. Laboda, L.R. Mclean, and M.C. Phillips Influence of molecular packing and phospholipid type on rates of cholesterol exchange Biochemistry 27 1988 3416 3423
25. D.A. Mannock, R.N.A.H. Lewis, and R.N. McElhaney Physical properties of glycosyl diacylglycerols. 1. Calorimetric studies of a homologous series of 1,2-di-O-acyl-3-O-(α-d-glucopyranosyl)-sn-glycerols Biochemistry 29 1990 7790 7799
26. 18, derived from sea urchin Transplant. Proc. 32 2000 2051 2053
27. Y. Matsumoto, H. Sahara, T. Fujita, K. Shimozawa, M. Takenouchi, T. Torigoe, S. Hanashima, T. Yamazaki, S. Takahashi, F. Sugawara, Y. Mizushina, K. Ohta, N. Takahashi, S. Gasa, K. Jimbow, K. Sakaguchi, and N. Sato An immunosuppressive effect by synthetic sulfonolipids deduced from sulfoquinovosyl diacylglycerols of sea urchin Transplantation 74 2002 261 267
28. K. Matsumoto, M. Takenouchi, K. Ohta, Y. Ohta, T. Imura, M. Oshige, Y. Yamamoto, H. Sahara, H. Sakai, M. Abe, F. Sugawara, N. Sato, and K. Sakaguchi Design of vesicles of 1,2-di-O-acyl-3-O-(β-D-sulfoquinovosyl)-glyceride bearing two stearic acids (β-SQDG-C18), a novel immunosuppressive drug Biochem. Pharmacol. 68 2004 2379 2386
29. H.M. McConell, and A. Radhakridhnan Condensed complexes of cholesterol and phospholipids Biochim. Biophys. Acta 1610 2003 159 173
30. T.P.W. McMullen, R.N.A.H. Lewis, and R.N. McElhaney Differential scanning calorimetric study of the effect of cholesterol on the thermotropic phase behavior of a homologous series of linear saturated phosphatidylcholines Biochemistry 32 1993 516 522
31. C. Murakami, T. Kumagai, T. Haba, U. Kanekazu, S. Nakazawa, S. Kamisuki, N. Maeda, X. Xu, H. Yoshida, F. Sugawara, K. Sakaguchi, and Y. Mizushina Effects of glycolipids from spinach on mammalian DNA polymerases Biochem. Pharmacol. 65 2003 259 267
32. K. Ohta, Y. Mizushina, N. Hirata, M. Takemura, F. Sugawara, A. Matsukage, S. Yoshida, and K. Sakaguchi Sulfoquinovosyldiacylglycerol, KM043, a new potent inhibitor of eukaryotic DNA polymerases and HIV-reverse transcriptase type 1 from a marine red alga, Gigartina tenella Chem. Pharm. Bull. 46 1998 684 686
33. N. Oku, D.A. Kendall, and R.C. Macdonald A simple procedure for the determination of the trapped volume of liposomes Biochim. Biophys. Acta 691 1982 332 340
34. M.C. Phillips, and D. Chapman Monolayer characteristics of saturated 1,2-diacyl phosphatidylcholines (lecithins) and phosphatidylethanolamines at the air-water interface Biochim. Biophys. Acta 163 1968 301 313
35. H. Sahara, M. Ishikawa, N. Takahashi, S. Ohtani, N. Sato, S. Gasa, T. Akino, and K. Kikuchi In vivo anti-tumor effect of 3′-sulfoquinovosyl 1′-monoacylglyceride isolated from sea urchin (Strongylocetroutus intermedius) intestine Br. J. Cancer 75 1997 324 332
36. G.L. Sassaki, P.A.J. Gorin, C.A. Tischer, and M. Iacomini Sulfoglycolipids from the lichenized basidiomycete Dictyonema glabratum: isolation, NMR, and ESI-MS approaches Glycobiology 11 2001 345 351
37. N. Sato, K. Sonoike, M. Tsuzuki, and A. Kawaguchi Impaired photosystem II in a mutant of Chlamydomonas reinhardtii defective in sulfoquinovosyl diacylglycerol Eur. J. Biochem. 234 1995 16 23
38. J. Senior, and G. Gregoriadis Stability of small unilamellar liposomes in serum and clearance from the circulation: the effect of the phospholipid and cholesterol components Life Sci. 14 1982 2123 2136
39. G.G. Shipley, J.P. Green, and B.W. Nichols The phase behavior of monogalactosyl and sulfoquinovosyl diglycerides Biochim. Biophys. Acta 311 1973 531 544
40. J.P. Slotte, A.L. Ostman, E.R. Kumar, and R. Bittman Cholesterol interacts with lactosyl and maltosyl cerebrosides but not with glucosyl or cerebrosides in mixed monolayers Biochemistry 32 1993 7886 7892
41. J.M. Smaby, M. Maureen, V.S. Kulkarni, and R.E. Brown Cholesterol-induced interfacial area condensations of galactosylceramides and sphingomyelins with identical acyl chains Biochemistry 35 1996 5696 5704
42. C. Tanford The Hydrophobic Effect: Formation of Micelles and Biological Membranes 1980 John Wiley & Sons New York
43. M.S. Webb, and B.R. Green Permeability properties of large unilamellar vesicles of thylakoid lipids Biochim. Biophys. Acta 984 1989 41 49
44. M.S. Webb, and B.R. Green Biochemical and biophysical properties of thylakoid acyl lipids Biochim. Biophys. Acta 1060 1991 133 158
45. P.L. Yeagle Cholesterol and the cell membrane Biochim. Biophys. Acta 822 1985 267 287
46. B. Yu, and C. Benning Anionic lipids are required for chloroplast structure and function in Arabidopsis Plant J. 36 2003 762 770