Abstract
Vicinal diols are important signaling metabolites of various inflammatory diseases, and some of them are potential biomarkers for some diseases. Utilizing the rapid reaction between diol and 6-bromo-3-pyridinylboronic acid (BPBA), a selective and sensitive approach was established to profile these vicinal diols using liquid chromatography-post column derivatization coupled with double precursor ion scan-mass spectrometry (LC-PCD-DPIS-MS). After derivatization, all BPBA-vicinal-diol esters gave a pair of characteristic isotope ions resulting from 79Br and 81Br. The unique isotope pattern generated two characteristic fragment ions of m/z 200 and 202. Compared to a traditional offline derivatization technique, the new LC-PCD-DPIS-MS method retained the capacity of LC separation. In addition, it is more sensitive and selective than a full scan MS method. As an application, an in vitro study of the metabolism of epoxy fatty acids by human soluble epoxide hydrolase was tested. These vicinal-diol metabolites of individual regioisomers from different types of polyunsaturated fatty acids were easily identified. The limit of detection (LOD) reached as low as 25 nM. The newly developed LC-PCD-DPIS-MS method shows significant advantages in improving the selectivity and therefore can be employed as a powerful tool for profiling vicinal-diol compounds from biological matrices.
Highlights
Vicinal diols are a large family of compounds that widely exist in biological systems, such as carbohydrates, nucleosides, nucleotide, and lipids
Studies from our laboratory have demonstrated that dihydroxyoctamonoenoic acids (DiHOMEs) (a.k.a., leukotoxin-diols) are more toxic than the corresponding epoxy fatty acids (EpFAs) (a.k.a., leukotoxin), and leukotoxin-diols are the toxic mediators involved in acute respiratory distress syndrome [19,20]
This paper demonstrates the efficacy and usefulness of a new Liquid chromatography (LC)-post column derivatization (PCD)-double precursor ion scan (DPIS)-MS
Summary
Vicinal diols (or 1,2-diols) are a large family of compounds that widely exist in biological systems, such as carbohydrates, nucleosides, nucleotide, and lipids. Among the latter, there are unique and important vicinal-diol metabolites that are generally produced from epoxy fatty acids (EpFAs) by epoxide hydrolases, which are ubiquitous cellular enzymes [1]. Unlike EpFAs, the vicinal diols are mostly reported as largely fewer active metabolites of the beneficial epoxides or for their putative toxicity and pro-inflammation effects [16]. Fatty acid 1,2-diols are potential biomarkers for inflammatory and other diseases. Establishing a rapid and selective method to profile these vicinal diols—present in trace amounts—is essential to discover their biological roles, as well as for establishing new markers of diseases
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
