Study of the orientational ordering of carotenoids in lipid bilayers by resonance-Raman spectroscopy

Ven, Martin van de; Kattenberg, Mark; Ginkel, G. van; Levine, Y.K.

doi:10.1016/s0006-3495(84)84269-1

Cited by 82 publications

(40 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It has been reported that the length of the dihydroxycarotenoid molecules (the distance between hydroxyl groups is 30.2 Å) is matched to the thickness of the hydrocarbon interior of the phosphatidylcholine bilayer, and it is assumed that lutein and zeaxanthin adopt an orientation mainly perpendicular to the membrane surface (33). Van de Ven et al (34) indicated that the orientation of ␤-carotene is parallel to the membrane surface in the dioleoylphosphatidylcholine bilayer, perpendicular to the membrane surface in a soybean-phosphatidylcholine bilayer, and both parallel and perpendicular in dimyristoylphosphatidylcholine membranes (34). It was also reported that the localization of macular xanthophylls, such as zeaxanthin and lutein, in detergent-soluble membranes was about six times more abundant than in the detergent-resistant membranes considered as lipid rafts (35).…”

Section: Discussionmentioning

confidence: 99%

Inhibitory Effect of Carotenoids on the Degranulation of Mast Cells via Suppression of Antigen-induced Aggregation of High Affinity IgE Receptors

Sakaï

Sugawara

Matsubara

et al. 2009

Journal of Biological Chemistry

View full text Add to dashboard Cite

Carotenoids have been demonstrated to possess antioxidative and anti-inflammatory effects. However, there is no report that the effects of carotenoids on degranulation of mast cell is critical for type I allergy. In this study, we focused on the effect of carotenoids on antigen-induced degranulation of mast cells. Fucoxanthin, astaxanthin, zeaxanthin, and ␤-carotene significantly inhibited the antigen-induced release of ␤-hexosaminidase in rat basophilic leukemia 2H3 cells and mouse bone marrow-derived mast cells. Those carotenoids also inhibited antigen-induced aggregation of the high affinity IgE receptor (Fc⑀RI), which is the most upstream of the degranulating signals of mast cells. Furthermore, carotenoids inhibited Fc⑀RI-mediated intracellular signaling, such as phosphorylation of Lyn kinase and Fyn kinase. It suggests that the inhibitory effect of carotenoids on the degranulation of mast cells were mainly due to suppressing the aggregation of Fc⑀RI followed by intracellular signaling. In addition, those carotenoids inhibited antigen-induced translocation of Fc⑀RI to lipid rafts, which are known as platforms of the aggregation of Fc⑀RI. We assume that carotenoids may modulate the function of lipid rafts and inhibit the translocation of Fc⑀RI to lipid rafts. This is the first report that focused on the aggregation of Fc⑀RI to investigate the mechanism of the inhibitory effects on the degranulation of mast cells and evaluated the functional activity of carotenoids associated with lipid rafts.Mast cells play pivotal roles in inflammation and immediatetype allergic reactions by secreting biologically active substances including histamine, eicosanoids, proteolytic enzymes, cytokines, and chemokines. The antigen-induced aggregation of the high affinity IgE receptor (Fc⑀RI) 2 expressed on the cell surface triggers the degranulation of mast cells. Fc⑀RI has a tetrameric structure comprised of an IgE binding ␣-chain, a ␤-chain, and a disulfide-linked ␥-chain dimer (1). The aggregation of Fc⑀RI by means of multivalent antigen-IgE complexes activates cytosolic Src protein-tyrosine kinases, such as Fyn and Lyn, which then regulate the activation of mast cells (2). Fyn kinase plays a key role in mast cell degranulation and in cytokine production by regulating Gab2 and phosphatidylinositol 3-kinase (3). Phosphorylated Lyn activates immunoreceptor tyrosine-based activation motifs of the ␤-and ␥-chains, and the phosphorylated immunoreceptor tyrosine-based activation motifs of the ␥-chain phosphorylate Syk kinase. Thereafter, a number of other signaling and adaptor molecules, such as phospholipase C␥ and protein kinase C (PKC), are phosphorylated (4). Phospholipase C␥ catalyzes the generation both of inositol 1,4,5-trisphosphate and diacylglycerol. Inositol 1,4,5-trisphosphate is an inducer of intracellular Ca 2ϩ mobilization, which is critical for degranulation, and diacylglycerol is an activator of PKC (5). Activated PKC is translocated from the cytosol to the plasma membrane fraction. PKC regulates many functions of ma...

show abstract

Section: Discussionmentioning

confidence: 99%

Inhibitory Effect of Carotenoids on the Degranulation of Mast Cells via Suppression of Antigen-induced Aggregation of High Affinity IgE Receptors

Sakaï

Sugawara

Matsubara

et al. 2009

Journal of Biological Chemistry

View full text Add to dashboard Cite

show abstract

“…Orientation of polar and nonpolar carotenoids (including their cis -forms) in the lipid-bilayer membrane has been investigated by many laboratories [19,44,47,58,59]. It is suggested that the presence of polar hydroxyl groups at the ends of carotenoid molecules and their transmembrane orientation (as in the case of zeaxanthin and lutein) enhance their antioxidant properties , as compared with the antioxidant properties of monopolar (β-cryptoxanthin) and nonpolar (β-carotene) carotenoids [40,60].…”

Section: Antioxidant Potency Of Macular Xanthophylls In Membranesmentioning

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

View full text Add to dashboard Cite

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.

show abstract

“…The length of a typical carotenoid matches the thickness of the hydrophobic membrane core (6). The molecular architecture of these pigments is responsible for their localization and orientation in the membranes and for their effects on the membrane properties (7)(8)(9)(10). Studies on a mixture of liposomes and carotenoids demonstrated that formation of the hydroxy derivatives of these compounds not only increased the rigidity of the lipid phase, but also blocked the penetration of protons through the membrane (11) and significantly decreased the oxygen diffusionconcentration product in the hydrocarbon region of model membranes (12).…”

mentioning

confidence: 99%

Low-temperature-induced accumulation of xanthophylls and its structural consequences in the photosynthetic membranes of the cyanobacterium Cylindrospermopsis raciborskii : An FTIR spectroscopic study

Várkonyi

Masamoto

Debreczeny

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

The effects of the growth temperature on the lipids and carotenoids of a filamentous cyanobacterium, Cylindrospermopsis raciborskii, were studied., The relative amounts of polyunsaturated glycerolipids and myxoxanthophylls in the thylakoid membranes increased markedly when this cyanobacterium was grown at 25°C instead of 35°C. Fourier transform infrared spectroscopy was used to analyze the low-temperature-induced structural alterations in the thylakoid membranes. Despite the higher amount of unsaturated lipids there, conventional analysis of the symCH2 band (characteristic of the lipid disorder) revealed more tightly arranged fatty-acyl chains for the thylakoids in the cells grown at 25°C as compared with those grown at 35°C. This apparent controversy was resolved by a two-component analysis of the symCH2 band, which demonstrated very rigid, myxoxanthophyll-related lipids in the thylakoid membranes. When this rigid component was excluded from the analysis of the thermotropic responses of the symCH2 bands, the expected higher fatty-acyl disorder was observed for the thylakoids prepared from cells grown at 25°C as compared with those grown at 35°C. Both the carotenoid composition and this rigid component in the thylakoid membranes were only growth temperature-dependent; the intensity of the illuminating light during cultivation had no apparent effect on these parameters. We propose that, besides their well-known protective functions, the polar carotenoids in particular may have structural effects on the thylakoid membranes. These effects should be exerted locally-by forming protective patches, in-membrane barriers of low dynamics-to prevent the access of reactive radicals generated in either enzymatic or photosynthetic processes to sensitive spots of the membranes.

show abstract

Study of the orientational ordering of carotenoids in lipid bilayers by resonance-Raman spectroscopy

Cited by 82 publications

References 18 publications

Inhibitory Effect of Carotenoids on the Degranulation of Mast Cells via Suppression of Antigen-induced Aggregation of High Affinity IgE Receptors

Inhibitory Effect of Carotenoids on the Degranulation of Mast Cells via Suppression of Antigen-induced Aggregation of High Affinity IgE Receptors

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

Low-temperature-induced accumulation of xanthophylls and its structural consequences in the photosynthetic membranes of the cyanobacterium Cylindrospermopsis raciborskii : An FTIR spectroscopic study

Contact Info

Product

Resources

About