Orientation of lutein in a lipid bilayer - revisited

• Authors: Marta Pasenkiewicz-Gierula , Krzysztof Baczyński , Krzysztof Murzyn , Michał Markiewicz
• Languages of publication: EN

Abstracts

EN

Lutein is present in the human retina and lens, where it plays a protective role. As lutein is associated with the lipid matrix of biomembranes, the role depends on its membrane location. Experimental studies predicted two orientations of lutein in a phosphatidylcholine (PC) bilayer: vertical and horizontal. Using a molecular dynamics simulation, we observed, in two different PC bilayers, both orientations of lutein, and in each bilayer, a single change from vertical to horizontal orientation or vice versa. Both orientations were stabilized by hydrogen bonding of lutein OH groups with mainly carbonyl but also phosphate oxygen atoms of PC.

Keywords

EN

molecular modeling; tilt angle; macular pigment

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2012
• Volume: 59
• Issue: 1
• Pages: 115-118

Dates

published

2012

received

2011-10-17

accepted

2012-03-01

(unknown)

2012-03-17

Contributors

author

Marta Pasenkiewicz-Gierula

• Department of Computational Biophysics and Bioinformatics, Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, Kraków, Poland

author

Krzysztof Baczyński

• Department of Computational Biophysics and Bioinformatics, Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, Kraków, Poland

author

Krzysztof Murzyn

• Department of Computational Biophysics and Bioinformatics, Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, Kraków, Poland

author

Michał Markiewicz

• Department of Computational Biophysics and Bioinformatics, Faculty of Biochemistry, Biophysics and Biotechnology, Jagiellonian University, Kraków, Poland

References

• Avogadro: an open-source molecular builder and visualization tool. Version 1.0.3.
• Bernstein PS, Khachik F, Carvalho LS, Muir GJ, Zhao DY, Katz NB (2001) Identification and quantitation of carotenoids and their metabolites in the tissues of the human eye. Exp Eye Res 72: 215-223.
• Essmann U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG (1995) A smooth particle mesh Ewald method. J Chem Phys 103: 8577-8593.
• Gasteiger J, Marsili M (1980) Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron 36: 3219-3228.
• Gaussian 09, Revision B.01 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov A,F Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2010) Gaussian, Inc., Wallingford CT.
• Group A-REDS (2001) A randomized, placebo-controlled, clinical trial of high-dose supplementation with vitamins c and e, beta carotene, and zinc for age-related macular degeneration and vision loss: Areds report no. 8. Arch Ophthalmol 119: 1417-1436.
• Gruszecki WI (2004) Carotenoid Orientation: Role in Membrane Stabilization. In Carotenoids in Health and Disease. Krinsky NI, Mayne ST, Sies H, eds, pp 151-162. Marcel Dekker Inc., New York.
• Hammond BR, Curran-Celentano J, Judd S, Fuld K, Krinsky NI, Wooten BR, Snodderly DM (1996) Sex differences in macular pigment optical density: relation to plasma carotenoid concentrations and dietary patterns. Vision Res 36: 2001-2012.
• Hammond BR, Wooten BR, Snodderly DM (1997) Individual variations in the spatial profile of human macular pigment. J Opt Soc Am A Opt Image Sci Vis 14: 1187-1196.
• Hess B, Bekker H, Berendsen HJC, Fraaije JGEM (1997) LINCS: a linear constraint solver for molecular simulations. J Compt Chem 18: 1463-1472.
• Hess B, Kutzner C, van der Spoel D, Lindahl E (2008) Gromacs 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation. J Chem Theor Comput 4: 435-447.
• Hoover WG (1985) Canonical dynamics: Equilibrium phase-space distributions. Phys Rev A 31: 1695-1697.
• Jorgensen WL, Chandrasekhar J, Madura JD, Impey RW, Klein ML (1983) Comparison of simple potential functions for simulating liquid water. J Chem Phys 79: 926-935.
• Jorgensen WL, Maxwell DS, Tirado-Rives J (1996) Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J Am Chem Soc 118: 11225-11236.
• Khachik F, Bernstein PS, Garland DL (1997) Identification of lutein and zeaxanthin oxidation products in human and monkey retinas. Invest Ophthalmol Vis Sci 38: 1802-1811.
• Landrum JT, Chatfield DC, Mebel AM, Alvarez-Calderon F, Fernandez MV (2010) The conformation of end-groups is one determinant of carotenoid topology suitable for high fidelity molecular recognition: a study of beta- and epsilon-end-groups. Arch Biochem Biophys 493: 169-74.
• Mayo SL, Olafson BD, Goddard WA (1990) DREIDING: a generic force field for molecular simulations. J Phys Chem 94: 8897-8909.
• Moeller SM, Voland R, Tinker L, Blodi BA, Klein ML, Gehrs KM, Johnson EJ, Snodderly DM, Wallace RB, Chappell RJ, Parekh N, Ritenbaugh C, Mares JA, CAREDS Study Group, Women's Health Initiative (2008) Associations between age-related nuclear cataract and lutein and zeaxanthin in the diet and serum in the carotenoids in the age-related eye disease study, an ancillary study of the women's health initiative. Arch Ophthalmol 126: 354-364.
• Parrinello M, Rahman A (1981) Polymorphic transitions in single crystals: A new molecular dynamics method. J Appl Phys 52: 7182-7190.
• Plesnar E, Subczynski WK, Pasenkiewicz-Gierula M (2012) Saturation with cholesterol increases vertical order and smoothes the surface of the phosphatidylcholine bilayer: A molecular simulation study. Biochim Biophys Acta 1818: 520-529.
• Richer S (1999) Armd-pilot (case series) environmental intervention data. J Am Optom Assoc 70: 24-36.
• Richer S, Stiles W, Statkute L, Pulido J, Frankowski J, Rudy D, Pei K, Tsipursky M, Nyland J (2004) Double-masked, placebo-controlled, randomized trial of lutein and antioxidant supplementation in the intervention of atrophic age-related macular degeneration: the veterans last study (lutein antioxidant supplementation trial). Optometry 75: 216-230.
• Seelig J, Waespe-Sarcevic N (1978) Molecular order in cis and trans unsaturated phospholipid bilayers. Biochemistry 17: 3310-3315.
• Snodderly DM, Auran JD, Delori FC (1984) The macular pigment. II. Spatial distribution in primate retinas. Invest Ophthalmol Vis Sci 25: 674-685.
• Sujak A, Gabrielska J, Grudziński W, Borc R, Mazurek P, Gruszecki WI (1999) Lutein and zeaxanthin as protectors of lipid membranes against oxidative damage: the structural aspects. Arch Biochem Biophys 371: 301-7.
• Sujak A, Okulski W, Gruszecki WI (2000) Organisation of xanthophyll pigments lutein and zeaxanthin in lipid membranes formed with dipalmitoylphosphatidylcholine. Biochim Biophys Acta 1509: 255-63.
• Vereshchagin AN, Vulfson SG (1966) Inductive interaction of weak dipoles in saturated hydrocarbons and their derivatives. Russ Chem Bul 16: 1186-1189.