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Free-radical Destruction of Sphingolipids Resulting in 2-hexadecenal Formation.

Shadyro O, Lisovskaya A, Semenkova G, Edimecheva I, Amaegberi N - Lipid Insights (2015)

Bottom Line: These findings prove the existence of a nonenzymatic pathway of sphingolipid destruction leading to the formation of Hex, which possesses a wide spectrum of biological activity.Analysis of the effect of HOCl on transplantable rat glioma C6 cells and human embryonic kidney 293 cells points to the formation of Hex.This suggests that the described mechanism of free-radical destruction of sphingolipids may be replicated on cell culture under the stress of active chlorine forms.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Belarusian State University, Minsk, Belarus.

ABSTRACT
The action of hypochlorous acid (HOCl) and γ-radiation on aqueous lysosphingolipid dispersions was found to produce 2-hexadecenal (Hex). This process includes the stages of formation of nitrogen-centered radicals from the starting molecules and the subsequent fragmentation of these radicals via the rupture of C-C and O-H bonds. These findings prove the existence of a nonenzymatic pathway of sphingolipid destruction leading to the formation of Hex, which possesses a wide spectrum of biological activity. Analysis of the effect of HOCl on transplantable rat glioma C6 cells and human embryonic kidney 293 cells points to the formation of Hex. This suggests that the described mechanism of free-radical destruction of sphingolipids may be replicated on cell culture under the stress of active chlorine forms.

No MeSH data available.


Related in: MedlinePlus

Mass spectrum of mono- and dichloramine derivatives of SPH formed in HOCl-treated deaerated aqueous SPH dispersions.
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Related In: Results  -  Collection


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f2-lpi-8-2015-001: Mass spectrum of mono- and dichloramine derivatives of SPH formed in HOCl-treated deaerated aqueous SPH dispersions.

Mentions: We examined the compositions of product mixtures formed on the addition of HOCl solutions (pH 5) to SPH, SPC, S1P, and SM dispersions. The reaction of HOCl with the sphingolipids was shown to yield chlorinated derivatives, which were identified by ESI-MS (see Methods). For example, in the mass spectrum of products formed in aqueous SPH dispersions treated with HOCl solutions (Fig. 2), mono- and dichlorinated SPH derivatives can be identified in positive mode by the molecular ion peaks [M + Na]+ at m/z 356 and 390, respectively, as well as by their characteristic fragmentation patterns.


Free-radical Destruction of Sphingolipids Resulting in 2-hexadecenal Formation.

Shadyro O, Lisovskaya A, Semenkova G, Edimecheva I, Amaegberi N - Lipid Insights (2015)

Mass spectrum of mono- and dichloramine derivatives of SPH formed in HOCl-treated deaerated aqueous SPH dispersions.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4376205&req=5

f2-lpi-8-2015-001: Mass spectrum of mono- and dichloramine derivatives of SPH formed in HOCl-treated deaerated aqueous SPH dispersions.
Mentions: We examined the compositions of product mixtures formed on the addition of HOCl solutions (pH 5) to SPH, SPC, S1P, and SM dispersions. The reaction of HOCl with the sphingolipids was shown to yield chlorinated derivatives, which were identified by ESI-MS (see Methods). For example, in the mass spectrum of products formed in aqueous SPH dispersions treated with HOCl solutions (Fig. 2), mono- and dichlorinated SPH derivatives can be identified in positive mode by the molecular ion peaks [M + Na]+ at m/z 356 and 390, respectively, as well as by their characteristic fragmentation patterns.

Bottom Line: These findings prove the existence of a nonenzymatic pathway of sphingolipid destruction leading to the formation of Hex, which possesses a wide spectrum of biological activity.Analysis of the effect of HOCl on transplantable rat glioma C6 cells and human embryonic kidney 293 cells points to the formation of Hex.This suggests that the described mechanism of free-radical destruction of sphingolipids may be replicated on cell culture under the stress of active chlorine forms.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Belarusian State University, Minsk, Belarus.

ABSTRACT
The action of hypochlorous acid (HOCl) and γ-radiation on aqueous lysosphingolipid dispersions was found to produce 2-hexadecenal (Hex). This process includes the stages of formation of nitrogen-centered radicals from the starting molecules and the subsequent fragmentation of these radicals via the rupture of C-C and O-H bonds. These findings prove the existence of a nonenzymatic pathway of sphingolipid destruction leading to the formation of Hex, which possesses a wide spectrum of biological activity. Analysis of the effect of HOCl on transplantable rat glioma C6 cells and human embryonic kidney 293 cells points to the formation of Hex. This suggests that the described mechanism of free-radical destruction of sphingolipids may be replicated on cell culture under the stress of active chlorine forms.

No MeSH data available.


Related in: MedlinePlus