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类异戊二烯醇易被单线态氧和羟基自由基氧化。

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

作者信息

Komaszylo Née Siedlecka Joanna, Kania Magdalena, Masnyk Marek, Cmoch Piotr, Lozinska Iwona, Czarnocki Zbigniew, Skorupinska-Tudek Karolina, Danikiewicz Witold, Swiezewska Ewa

机构信息

Department of Lipid Biochemistry, Institute of Biochemistry and Biophysics, Polish Academy of Sciences (PAS), Pawinskiego 5a, 02-106, Warsaw, Poland.

Laboratory of Mass Spectrometry, Institute of Organic Chemistry, Polish Academy of Sciences (PAS), Kasprzaka 44/52, 01-224, Warsaw, Poland.

出版信息

Lipids. 2016 Feb;51(2):229-44. doi: 10.1007/s11745-015-4104-y. Epub 2015 Dec 30.

DOI:10.1007/s11745-015-4104-y
PMID:26715533
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4735226/
Abstract

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.

摘要

类异戊二烯作为所有活细胞的常见成分，会接触到氧化剂，例如活性氧物种，单线态氧或羟基自由基。尽管如此，聚异戊二烯氧化产物从未被表征过。在本研究中，使用单线态氧（在过氧化氢/钼酸盐存在下产生或在卟啉存在下进行光化学反应时产生）、氧气（过氧化氢歧化时形成）或羟基自由基（通过过氧化氢/超声、紫外线/二氧化钛或紫外线/过氧化氢产生）体系对类异戊二烯醇（2- 异戊烯醇和10-异戊烯醇）进行化学氧化。借助质谱（MS）和核磁共振（NMR）方法研究了所得产物（羟基、过氧和杂环衍生物）的结构。此外，电喷雾电离质谱似乎是检测类异戊二烯氧化产物（电喷雾电离质谱分析）以及根据选定离子的碎裂谱确定其结构（电喷雾串联质谱分析）的有用分析工具。综上所述，首次表明了聚异戊二烯醇对各种氧化剂的敏感性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f1b1/4735226/6f6553a25705/11745_2015_4104_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f1b1/4735226/7d772dd586c1/11745_2015_4104_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f1b1/4735226/af54b805c433/11745_2015_4104_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f1b1/4735226/6f6553a25705/11745_2015_4104_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f1b1/4735226/7d772dd586c1/11745_2015_4104_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f1b1/4735226/af54b805c433/11745_2015_4104_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f1b1/4735226/6f6553a25705/11745_2015_4104_Fig3_HTML.jpg

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