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By identifying and comparing the major, non\u2010polar lipids in normal eye tears with a dry eye model, it may be possible to identify a symptom of, or a contributing factor to, dry eye. Electrospray tandem mass spectrometry (ES\u2010MS\/MS) was used to identify and compare the non\u2010polar lipids, detected as lithium adducts, from normal and dry eye tear samples obtained from rabbits. A limited number of normal human tear samples were also examined for lipid content, and a close resemblance to rabbit was observed. Three distinct regions were delineated in the ES mass spectra of the non polar lipids, <jats:italic>m<\/jats:italic>\/<jats:italic>z<\/jats:italic> 20\u2013500, 500\u2013800 and 800\u20131100. A common feature noted among identified lipid components was a glycerol backbone with fatty acyl substituents attached. Product ion spectra were obtained for lithiated monoacyl\u2010, 1,2\u2010 and 1,3\u2010diacyl\u2010 and triacylglyceride standards. Newly proposed structures and fragmentation pathways for the major product ions are presented for the 1,2\u2010 and 1,3\u2010diglycerides, and also for the monoglyceride. New approaches to distinguishing asymmetric 1,2\u2010diglycerides and 1,2\u2010 from 1,3\u2010diglycerides are proposed. For the rabbit tear samples, the <jats:italic>m<\/jats:italic>\/<jats:italic>z<\/jats:italic> 20\u2013500 range contains monoester diols with empirical formulas C<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub>H<jats:sub>2<jats:italic>n<\/jats:italic><\/jats:sub>O<jats:sub>4<\/jats:sub>, the <jats:italic>m<\/jats:italic>\/<jats:italic>z<\/jats:italic> 500\u2013800 range includes diesters with empirical formulas C<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub>H<jats:sub>2<jats:italic>n<\/jats:italic>\u22122<\/jats:sub>O<jats:sub>5<\/jats:sub> and the <jats:italic>m<\/jats:italic>\/<jats:italic>z<\/jats:italic> 800\u20131100 range contains triesters with empirical formulas C<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub>H<jats:sub>2<jats:italic>n<\/jats:italic>\u22124<\/jats:sub>O<jats:sub>6<\/jats:sub>. Also found in the extracts were three isoprene acetals (terpenoids). Copyright \u00a9 2004 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/jms.725","type":"journal-article","created":{"date-parts":[[2004,11,5]],"date-time":"2004-11-05T16:28:56Z","timestamp":1099672136000},"page":"1321-1336","source":"Crossref","is-referenced-by-count":55,"title":["Identification, quantification and comparison of major non\u2010polar lipids in normal and dry eye tear lipidomes by electrospray tandem mass spectrometry"],"prefix":"10.1002","volume":"39","author":[{"given":"Bryan M.","family":"Ham","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean T.","family":"Jacob","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monica M.","family":"Keese","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Richard B.","family":"Cole","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2004,11,5]]},"reference":[{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1001\/jama.286.17.2114"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1600-0420.1997.tb00774.x"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0002-9394(14)71688-5"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4615-5359-5_99"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1159\/000310154"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1001\/archopht.119.10.1487"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0014-4835(81)80069-3"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4615-5359-5_37"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1017987608937"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF02534237"},{"key":"e_1_2_6_12_2","first-page":"2260","article-title":"Targeted disruption of stearoyl\u2010CoA desaturase1 gene in mice causes atrophy of sebaceous and meibomian glands and depletion of wax esters in the eyelid","author":"Miyazaki M","year":"2001","journal-title":"Nutrient\u2010Gene Express."},{"key":"e_1_2_6_13_2","first-page":"79","article-title":"A compositional based model for the tear film lipid layer","volume":"95","author":"McCulley JP","year":"1997","journal-title":"Trans. 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