Lipid Ozonation Products Activate Phospholipases A2, C, and D

Kafoury, Ramzi M.; Pryor, William A.; Squadrito, G; Salgo, Maria G.; Zou, Xiaoyan; Friedman, Mitchell

doi:10.1006/taap.1998.8418

Cited by 60 publications

(63 citation statements)

References 56 publications

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“…Previous studies have determined the impact that ozonization of lipids, particularly polyunsaturated fatty acids (PUFA), may have on O 3 -associated toxic effects. These studies demonstrated that ozonization of PUFAs and the formation of lipid ozonization products can mimic many of the adverse health effects observed after exposure to O 3 (5,(7)(8)(9). However, the involvement of cholesterol ozonization products requires further study.…”

mentioning

confidence: 98%

Ozone-derived Oxysterols Affect Liver X Receptor (LXR) Signaling

Speen

Kim

Bauer

et al. 2016

Journal of Biological Chemistry

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mentioning

confidence: 98%

Ozone-derived Oxysterols Affect Liver X Receptor (LXR) Signaling

Speen

Kim

Bauer

et al. 2016

Journal of Biological Chemistry

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“…The high reactivity of O 3 and its low solubility in water would prevent it from passing through the lung epithelial lining fluid to act directly on the underlying epithelial cells (3). Since the lung epithelial lining fluid is composed of lipids to a large extent, it has been suggested that O 3 exerts its toxic effects via oxidized lipid mediators that can act as signaling molecules (3)(4)(5)(6)(7).…”

mentioning

confidence: 99%

Vγ1+ T Cells and Tumor Necrosis Factor-Alpha in Ozone-Induced Airway Hyperresponsiveness

Matsubara

Takeda

Jin

et al. 2009

Am J Respir Cell Mol Biol

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“…Lung epithelial lining fluid, which contains pulmonary surfactant, is composed of almost 95% lipids (Sadana et al, 1988;Hall et al, 1994); thus, it has been proposed that ozone exerts its toxic effects via a lipid mediator, which is formed during the interaction of ozone with lipids in the pulmonary surfactant (Pryor et al, 1995;Postlethwait et al, 1998). Various studies have shown that oxidized lipids can act as signaling molecules (Kafoury et al, 1998;Uhlson et al, 2002); for example, lysophospholipids, which could potentially be formed during ozonolysis, have been shown to initiate PAF-like activity (Marathe et al, 1999).…”

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confidence: 99%

Ozone Exposure in Vivo and Formation of Biologically Active Oxysterols in the Lung

Pulfer¹,

Taube²,

Gelfand³

et al. 2004

J Pharmacol Exp Ther

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Ozone toxicity in the lung is thought to be mediated by products derived from the reaction of ozone with components of the lung epithelial lining fluid. Cholesterol is an abundant component of this epithelial lining fluid, and it is susceptible to ozonolysis, yielding several stable products including 3␤-hydroxy-5-oxo-5,6-secocholestan-6-al and 5␤,6␤-epoxycholesterol. Both 5␤,6␤-epoxycholesterol and its metabolite, cholestan-6-oxo-3,5-diol, have been shown to cause cytotoxicity in vitro, suggesting that they may be potential mediators of ozone toxicity in vivo. An ozone-sensitive mouse strain, C57BL/6J, was exposed to varying concentrations of ozone (0.5-3.0 ppm), and subsequently the levels of these cholesterol ozonolysis products were quantitated by electrospray ionization mass spectrometry in bronchoalveolar lavage fluid, lavaged cells, and lung homogenate. An ozone dosedependent formation of these biologically active oxysterols was observed in vivo, supporting a role for these compounds in ozone toxicity. Since the 5␤,6␤-epoxycholesterol metabolite, cholestan-6-oxo-3,5-diol, was isobaric with other cholesterol ozonolysis products, 3␤-hydroxy-5-oxo-5,6-secocholestan-6-al and its aldol condensation product, 3␤-hydroxy-5␤-hydroxy-B-norcholestan-6␤-carboxaldehyde, detailed mass spectral analysis using electron impact ionization was utilized to differentiate these isobaric cholesterol ozonolysis products. The specific detection of cholestan-6-oxo-3,5-diol in lung homogenate after ozone exposure established formation of 5␤,6␤-epoxycholesterol within the lung after exposure to 0.5 ppm ozone.

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Lipid Ozonation Products Activate Phospholipases A2, C, and D

Cited by 60 publications

References 56 publications

Ozone-derived Oxysterols Affect Liver X Receptor (LXR) Signaling

Ozone-derived Oxysterols Affect Liver X Receptor (LXR) Signaling

Vγ1+ T Cells and Tumor Necrosis Factor-Alpha in Ozone-Induced Airway Hyperresponsiveness

Ozone Exposure in Vivo and Formation of Biologically Active Oxysterols in the Lung

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