Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals

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• 作者：Joanna Komaszylo née Siedlecka ; Magdalena Kania ; Marek Masnyk ; Piotr Cmoch…
• 关键词：Isoprenoid oxidation ; Singlet oxygen ; Hydrogen peroxide ; Sodium molybdate ; Porphyrin ; Hydroxyl radical ; Oxygen ; UV irradiation
• 刊名：Lipids
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：51
• 期：2
• 页码：229-244
• 全文大小：594 KB
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• 作者单位：Joanna Komaszylo née Siedlecka (1)
  Magdalena Kania (2)
  Marek Masnyk (2)
  Piotr Cmoch (2)
  Iwona Lozinska (3)
  Zbigniew Czarnocki (3)
  Karolina Skorupinska-Tudek (1)
  Witold Danikiewicz (2)
  Ewa Swiezewska (1)
  
  1. Department of Lipid Biochemistry, Institute of Biochemistry and Biophysics, Polish Academy of Sciences (PAS), Pawinskiego 5a, 02-106, Warsaw, Poland
  2. Laboratory of Mass Spectrometry, Institute of Organic Chemistry, Polish Academy of Sciences (PAS), Kasprzaka 44/52, 01-224, Warsaw, Poland
  3. Faculty of Chemistry, University of Warsaw, Warsaw, Poland
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Life Sciences
  Biochemistry
  Medicinal Chemistry
  Microbial Genetics and Genomics
  Nutrition
  Bioorganic Chemistry
  Medical Biochemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1558-9307

文摘

Isoprenoids, as common constituents of all living cells, are exposed to oxidative agents—reactive oxygen species, for example, singlet oxygen or hydroxyl radicals. Despite this fact, products of oxidation of polyisoprenoids have never been characterized. In this study, chemical oxidation of isoprenoid alcohols (Prenol-2 and -10) was performed using singlet oxygen (generated in the presence of hydrogen peroxide/molybdate or upon photochemical reaction in the presence of porphyrin), oxygen (formed upon hydrogen peroxide dismutation) or hydroxyl radical (generated by the hydrogen peroxide/sonication, UV/titanium dioxide or UV/hydrogen peroxide) systems. The structure of the obtained products, hydroxy-, peroxy- and heterocyclic derivatives, was studied with the aid of mass spectrometry (MS) and nuclear magnetic resonance (NMR) methods. Furthermore, mass spectrometry with electrospray ionization appeared to be a useful analytical tool to detect the products of oxidation of isoprenoids (ESI–MS analysis), as well as to establish their structure on the basis of the fragmentation spectra of selected ions (ESI–MS/MS analysis). Taken together, susceptibility of polyisoprenoid alcohols to various oxidizing agents was shown for the first time. Keywords Isoprenoid oxidation Singlet oxygen Hydrogen peroxide Sodium molybdate Porphyrin Hydroxyl radical Oxygen UV irradiation