Interaction of isomeric forms of xanthophyll pigment zeaxanthin with dipalmitoylphosphatidylcholine studied in monomolecular layers

Milanowska, J.; Polit, Agnieszka; Wasylewski, Zygmunt; Gruszecki, Wiesław I.

doi:10.1016/j.jphotobiol.2003.08.009

Cited by 29 publications

(22 citation statements)

References 20 publications

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“…Alternatively, all polar groups of a xanthophyll molecule can remain with contact with the same polar headgroup region of the membrane. Such orientation has been proposed for xanthophylls in a conformation cis [39]. Interestingly, lutein characterised by the rotational freedom around the 6′-7′ single bond is believed to adopt 2 orthogonal orientations: one roughly vertical and the other horizontal to the lipid bilayer [40,41].…”

Section: Localisation Within Model Membranesmentioning

confidence: 85%

Characterisation of Carotenoids Involved in the Xanthophyll Cycle

Kuczyńska¹,

Jemioła-Rzemińska²,

KazimierzStrzalka³

2017

Carotenoids

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Carotenoids are known for versatile roles they play in living organisms; however, their most pivotal function is involvement in scavenging reactive oxygen species (ROS) and photoprotection. In plant kingdom, an important photoprotective mechanism, referred to as the xanthophyll cycle, has been developed by photosynthetic organism to avoid excess light that might lead to photoinhibition and inactivation of photosystems and induce the formation of reactive oxygen species (ROS), resulting in photodamage and long-term changes in the cells caused by oxidative stress. Apart from high-light driven enzymatic conversion of violaxanthin (Viola) to zeaxanthin (Zea) that occurs mostly in higher plants, mosses and lichens, other less known types of the xanthophyll cycle have been hitherto described. The work is aimed at summarising the current knowledge on the pigments engaged in the xanthophyll cycles operating in various organisms.

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Section: Localisation Within Model Membranesmentioning

confidence: 85%

Characterisation of Carotenoids Involved in the Xanthophyll Cycle

Kuczyńska¹,

Jemioła-Rzemińska²,

KazimierzStrzalka³

2017

Carotenoids

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“…Monopolar β-cryptoxanthin is also less soluble in the lipid bilayer than macular xanthophylls [41]. Interestingly, the tendency of cis -isomers of xanthophylls to aggregate is usually much less than their all- trans counterparts [42,43], and they also affect membrane properties more strongly (the effect of zeaxanthin on membrane properties increases in the direction: all- trans < 9- cis ≤ 13- cis [44]). Cis -isomers are also more readily solubilized, absorbed, and transported [42].…”

Section: Transport Of Macular Xanthophylls and Their Solubility And Omentioning

confidence: 99%

Location of macular xanthophylls in the most vulnerable regions of photoreceptor outer-segment membranes

Subczynski

Wiśniewska

Widomska

2010

Archives of Biochemistry and Biophysics

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Lutein and zeaxanthin are two dietary carotenoids that compose the macular pigment of the primate retina. Another carotenoid, meso-zeaxanthin, is formed from lutein in the retina. A membrane location is one possible site where these dipolar, terminally dihydroxylated carotenoids, named macular xanthophylls, are accumulated in the nerve fibers and photoreceptor outer segments. Macular xanthophylls are oriented perpendicular to the membrane surface, which ensures their high solubility, stability, and significant effects on membrane properties. It was recently shown that they are selectively accumulated in membrane domains that contain unsaturated phospholipids, and thus are located in the most vulnerable regions of the membrane. This location is ideal if they are to act as lipid antioxidants, which is the most accepted mechanism through which lutein and zeaxanthin protect the retina from age-related macular degeneration. In this mini-review, we examine published data on carotenoid-membrane interactions and present our hypothesis that the specific orientation and location of macular xanthophylls maximize their protective action in membranes of the eye retina.

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“…Figure 3 presents the analysis of molecular interactions in the two-component DPPC-CAN monolayers, in terms of the additivity rule, in the concentration range below 5 mol% carotenoid. The molecular areas of the two-component films formed with DPPC and other xanthophyll pigments (e.g., lutein and zeaxanthin) are overadditive [19,20], which indicates that the mean molecular area values are located above the theoretical linear dependencies (such as that one presented in Figure 3), representing the ideal mixing. Such an effect was particularly pronounced at low molecular fractions of the pigments, below the aggregation threshold in the monolayers.…”

Section: Resultsmentioning

confidence: 89%

Organization of two-component monomolecular layers formed with dipalmitoylphosphatidylcholine and the carotenoid pigment, canthaxanthin

Sujak

Gagoś

Serra

et al. 2007

Molecular Membrane Biology

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Canthaxanthin is a carotenoid pigment of physiological importance owing to potential modulation of the dynamic and structural properties of biomembranes. The effect of canthaxanthin on the organization of lipid membranes formed with dipalmitoylphosphatidylcholine (DPPC) was studied with application of monomolecular layer technique, FTIR spectroscopy and linear dichroism-FTIR. The specific molecular areas of the two-component monomolecular layers of canthaxanthin-DPPC show pronounced underadditivity in the concentration range below 2 mol% carotenoid with respect to the lipid, corresponding to the monomeric organization of the pigment. Additionally, the analysis of the FTIR spectra of the two-component monolayers deposited to the solid support shows that organization of the carotenoid in the lipid monolayer is governed primarily by van der Waals interactions between the pigment chromophore and lipid alkyl chains. This interaction is responsible for an ordering effect of canthaxanthin with respect to lipids. Analysis of FTIR spectra of two-component monolayers suggests the possibility of hydrogen bonding between the lipid polar headgroups and the keto groups of canthaxanthin via water bridges.

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Interaction of isomeric forms of xanthophyll pigment zeaxanthin with dipalmitoylphosphatidylcholine studied in monomolecular layers

Cited by 29 publications

References 20 publications

Characterisation of Carotenoids Involved in the Xanthophyll Cycle

Characterisation of Carotenoids Involved in the Xanthophyll Cycle

Location of macular xanthophylls in the most vulnerable regions of photoreceptor outer-segment membranes

Organization of two-component monomolecular layers formed with dipalmitoylphosphatidylcholine and the carotenoid pigment, canthaxanthin

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