{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,6]],"date-time":"2026-04-06T14:03:05Z","timestamp":1775484185205,"version":"3.50.1"},"reference-count":51,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2016,9,25]],"date-time":"2016-09-25T00:00:00Z","timestamp":1474761600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2016,11,15]]},"abstract":"<jats:sec>\n                    <jats:title>Rationale<\/jats:title>\n                    <jats:p>\n                      (\n                      <jats:italic>O<\/jats:italic>\n                      \u2010acyl)\u2010hydroxy fatty acids (OAHFAs) are a recently discovered class of endogenous lipids, generating significant interest for their correlation with enhanced glucose tolerance. Structural variants that differ in the position of the ester linkage have been described, including the \u03c9\u2010OAHFA sub\u2010class, that plays a key role in stabilizing the human tear film. Developing analytical tools for rapid and unambiguous structural elucidation of OAHFAs is essential to understanding their diverse physiological functions.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Methods<\/jats:title>\n                    <jats:p>\n                      Commercially available and synthesized OAHFA standards were dissolved in chloroform and subsequently diluted into methanol with 1.5\u00a0mM ammonium acetate. Negative ion collision\u2010induced dissociation (CID) MS\n                      <jats:sup>n<\/jats:sup>\n                      spectra were acquired using chip\u2010based nano\u2010electrospray ionization (Advion TriVersa NanoMate) coupled to an Orbitrap Elite mass spectrometer (Thermo Fisher Scientific).\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Results<\/jats:title>\n                    <jats:p>\n                      Major product ions observed during CID of [OAHFA \u2013 H]\n                      <jats:sup>\u2212<\/jats:sup>\n                      ions readily identify the constituent fatty acid and hydroxy fatty acid; however, isomers are not easily distinguished. Interrogation of the hydroxy fatty acid and dehydrated hydroxy fatty acid product ions by MS\n                      <jats:sup>n<\/jats:sup>\n                      and ion\u2010molecule reactions yielded diagnostic ions that readily pinpoint hydroxylation position and, thus, the OAHFA ester location. Conversely, these ions are characteristically absent in the MS\n                      <jats:sup>3<\/jats:sup>\n                      spectra of \u03c9\u2010OAHFAs. Unimolecular dissociation mechanisms are proposed, which are shown to be consistent with prior isotopic labelling experiments.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Conclusions<\/jats:title>\n                    <jats:p>\n                      A mechanistic rationale is provided to explain the unimolecular dissociation of [OAHFA \u2013 H]\n                      <jats:sup>\u2212<\/jats:sup>\n                      ions in an ion trap mass spectrometer, thus enabling near\u2010complete\n                      <jats:italic>de novo<\/jats:italic>\n                      structural elucidation of OAHFAs in shotgun lipidomics workflows, even if synthetic standards are unavailable for comparison. Copyright \u00a9 2016 John Wiley &amp; Sons, Ltd.\n                    <\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.7715","type":"journal-article","created":{"date-parts":[[2016,8,12]],"date-time":"2016-08-12T21:18:42Z","timestamp":1471036722000},"page":"2351-2359","source":"Crossref","is-referenced-by-count":33,"title":["Determination of ester position in isomeric (\n                    <i>O<\/i>\n                    \u2010acyl)\u2010hydroxy fatty acids by ion trap mass spectrometry"],"prefix":"10.1002","volume":"30","author":[{"given":"David L.","family":"Marshall","sequence":"first","affiliation":[{"name":"Central Analytical Research Facility Queensland University of Technology  Brisbane QLD 4001 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jennifer T.","family":"Saville","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Wollongong  Wollongong NSW 2522 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alan T.","family":"Maccarone","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Wollongong  Wollongong NSW 2522 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ramesh","family":"Ailuri","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Wollongong  Wollongong NSW 2522 Australia"},{"name":"Illawarra Health and Medical Research Institute University of Wollongong  Wollongong NSW 2522 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael J.","family":"Kelso","sequence":"additional","affiliation":[{"name":"School of Chemistry University of Wollongong  Wollongong NSW 2522 Australia"},{"name":"Illawarra Health and Medical Research Institute University of Wollongong  Wollongong NSW 2522 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Todd W.","family":"Mitchell","sequence":"additional","affiliation":[{"name":"School of Medicine University of Wollongong  Wollongong NSW 2522 Australia"},{"name":"Illawarra Health and Medical Research Institute University of Wollongong  Wollongong NSW 2522 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stephen J.","family":"Blanksby","sequence":"additional","affiliation":[{"name":"Central Analytical Research Facility Queensland University of Technology  Brisbane QLD 4001 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2016,9,25]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cell.2005.01.024"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13361-012-0410-2"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.anchem.111808.073705"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/mas.20284"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/mas.20342"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527655946"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11745-998-0214-x"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.3090"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac300953j"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5AN00838G"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5AN02062J"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.7430"},{"key":"e_1_2_6_14_1","volume-title":"Tandem Mass Spectrometry of Lipids: Molecular Analysis of Complex Lipids","author":"Murphy R. C.","year":"2015"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11745-998-0215-9"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11746-003-0786-x"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cell.2014.09.035"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2016.040"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1194\/jlr.M900252-JLR200"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1167\/iovs.13-12916"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1194\/jlr.M044826"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2014.04.082"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.exer.2013.05.010"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.exer.2013.06.016"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02540517"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11746-001-0304-1"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.6503"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13361-015-1328-2"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1186\/s13321-015-0104-4"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmeth1060"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac7017684"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-60761-322-0_21"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp012929r"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1194\/jlr.E400004-JLR200"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1194\/jlr.M033506"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1044-0305(00)00159-8"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.520"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/a706571j"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/a708654g"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.1545"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00326a039"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00217a003"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/0168-1176(90)80028-2"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp0019714"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00343a029"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00274a005"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/0378-4347(95)00212-2"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/1044-0305(95)00628-1"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbalip.2011.04.015"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3AN01712E"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.5b04001"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ab.2010.10.006"}],"container-title":["Rapid Communications in Mass Spectrometry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Frcm.7715","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Frcm.7715","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/rcm.7715","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T12:31:10Z","timestamp":1761481870000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/rcm.7715"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,9,25]]},"references-count":51,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2016,11,15]]}},"alternative-id":["10.1002\/rcm.7715"],"URL":"https:\/\/doi.org\/10.1002\/rcm.7715","archive":["Portico"],"relation":{},"ISSN":["0951-4198","1097-0231"],"issn-type":[{"value":"0951-4198","type":"print"},{"value":"1097-0231","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,9,25]]}}}