Hydrophilic Carotenoids: Surface Properties and Aggregation of Crocin as a Biosurfactant

Naess, Stine Nalum; Elgsaeter, Arnljot; Foss, Bjarne A.; Li, Baojun; Sliwka, Hans‐Richard; Partali, Vassilia; Melø, Thor Bernt; Naqvi, K. Razi

doi:10.1002/hlca.200690011

Cited by 39 publications

(28 citation statements)

References 40 publications

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“…A direct transcriptional role for crocin is unclear, but it is conceivable that its ER stress-modulating effects might stem from its suppression of inflammation and free radical generation. Although crocin had no apparent suppressive effects on T cell proliferation, it exerted a robust neuroprotective effect by reducing ER stress and inflammation in the CNS during EAE, underscoring its direct effects on CNS, perhaps because of its highly lipophilic properties (66). When crocin was administered to EAE mice 7 d post-EAE induction, the resulting neuropathology was reduced, as evident by the preserved axonal counts in treated EAE animals.…”

Section: Discussionmentioning

confidence: 97%

Neuroinflammation and Endoplasmic Reticulum Stress Are Coregulated by Crocin To Prevent Demyelination and Neurodegeneration

Deslauriers

Afkhami-Goli

Paul

et al. 2011

The Journal of Immunology

113

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Endoplasmic reticulum (ER) stress is a homeostatic mechanism, which is used by cells to adapt to intercellular and intracellular changes. Moreover, ER stress is closely linked to inflammatory pathways. We hypothesized that ER stress is an integral component of neuroinflammation and contributes to the development of neurological diseases. In autopsied brain specimens from multiple sclerosis (MS) and non-MS patients, XBP-1 spliced variant (XBP-1/s) was increased in MS brains (p < 0.05) and was correlated with the expression of the human endogenous retrovirus-W envelope transcript, which encodes the glycoprotein, Syncytin-1 (p < 0.05). In primary human fetal astrocytes transfected with a Syncytin-1–expressing plasmid, XBP-1/s, BiP, and NOS2 were induced, which was suppressed by crocin treatment (p < 0.05). Crocin also protected oligodendrocytes exposed to cytotoxic supernatants derived from Syncytin-1–expressing astrocytes (p < 0.05) and NO-mediated oligodendrocytotoxicity (p < 0.05). During experimental autoimmune encephalomyelitis (EAE), the transcript levels of the ER stress genes XBP-1/s, BiP, PERK, and CHOP were increased in diseased spinal cords compared with healthy littermates (p < 0.05), although CHOP expression was not involved in the EAE disease phenotype. Daily treatment with crocin starting on day 7 post-EAE induction suppressed ER stress and inflammatory gene expression in spinal cords (p < 0.05), which was accompanied by preserved myelination and axonal density, together with reduced T cell infiltration and macrophage activation. EAE-associated neurobehavioral deficits were also ameliorated by crocin treatment (p < 0.05). These findings underscored the convergent roles of pathogenic ER stress and immune pathways in neuroinflammatory disease and point to potential therapeutic applications for crocin.

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Section: Discussionmentioning

confidence: 97%

Neuroinflammation and Endoplasmic Reticulum Stress Are Coregulated by Crocin To Prevent Demyelination and Neurodegeneration

Deslauriers

Afkhami-Goli

Paul

et al. 2011

The Journal of Immunology

113

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“…[38,47,50] The synthesis and properties of Carox 3, the surface and aggregation properties of 9, and the antioxidant activity of 8 and 9 will be reported elsewhere. C30est 5, C30ald 6, and Asta 7 were kindly provided by H. Ernst, BASF AG (Ludwigshafen, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…[22] The surface and aggregate properties of the natural neutral bolaamphiphile crocin "Croc" 8 have also been determined [47] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Electron‐ and Energy‐Transfer Properties of Hydrophilic Carotenoids

Sliwka

Melø

Foss

et al. 2007

Chemistry A European J

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The antioxidant activities-expressed as the electron-donating properties-of five hydrophilic carotenoids (carotenoid surfactants) and three related hydrophobic carotenoids were investigated by flash photolysis. The electron-transfer rates of the carotenoids to the triplet state of the sensitizer 2-nitronaphthalene and the energy transfer rates of triplet 2-nitronaphthalene to the carotenoids were determined. The results demonstrate that the electron-donating effects of the hydrophilic and hydrophobic carotenoids were comparable when evaluated in acetonitrile. In the presence of water, however, electron transfer (i.e., antioxidant efficiency) was enhanced by a factor of four for the hydrophilic carotenoids. The increased hydrophilicity of carotenoids, therefore, could expand their antioxidant properties, thus facilitating their use as aqueous-phase radical scavengers. At the same time, it was shown that supramolecular assembly ("aggregation") of the amphiphilic carotenoids prevented electron transfer, thus deactivating the antioxidant function. Modulation of the biophysical properties of carotenoids through synthetic modification is capable of increasing the biological and medical utility of this natural class of predominantly hydrophobic antioxidant compound.

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“…Acids 11 and 12 were obtained after purification and hydrolysis of crocin (Fluka) and C30 ethyl ester 13. [46,47] Preparation and Work-Up Procedure: Car (1) (20 mg, 0.067 mmol) was dissolved under a strong stream of N 2 in dry deoxygenated DMSO or DMF (4 mL). MeOK (25 % in MeOH, 100 µL) was added and the reaction stirred at room temperature under a continuous stream of N 2 for 2 h. The reaction became evident by a color change from orange 1 to blue 3.…”

Section: Concluding Remarkmentioning

confidence: 99%

Facile Electron Uptake by Carotenoids Under Mild, Non‐Radiative Conditions: Formation of Carotenoid Anions

2010

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Hydrophilic Carotenoids: Surface Properties and Aggregation of Crocin as a Biosurfactant

Cited by 39 publications

References 40 publications

Neuroinflammation and Endoplasmic Reticulum Stress Are Coregulated by Crocin To Prevent Demyelination and Neurodegeneration

Neuroinflammation and Endoplasmic Reticulum Stress Are Coregulated by Crocin To Prevent Demyelination and Neurodegeneration

Electron‐ and Energy‐Transfer Properties of Hydrophilic Carotenoids

Facile Electron Uptake by Carotenoids Under Mild, Non‐Radiative Conditions: Formation of Carotenoid Anions

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