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The triglyceride composition,structure, and presence of estolides in the oils ofLesquerella and related species
Authors:Douglas G Hayes  Robert Kleiman  Bliss S Phillips
Affiliation:(1) New Crops Research, NCAUR, ARS, USDA, 61604 Peoria, Illinois;(2) Dept. of Chemical Engineering, University of Alabama in Huntsville, 35899 Huntsville, AL, 35899
Abstract:Members of the genusLesquerella, native to North America, have oils containing large amounts of hydroxy fatty acids and are under investigation as potential new crops. The triglyceride structure of oils from twenty-fiveLesquerella species in the seed collection at our research center has been examined after being hydrolysis-catalyzed by reverse micellar-encapsulated lipase and alcoholysis-catalyzed by immobilized lipase. These reactions, when coupled with supercritical-fluid chromatographic analysis, provide a powerful, labor-saving method for oil triglyceride analysis. A comprehensive analysis of overall fatty acid composition of these oils has been conducted as well.Lesquerella oils (along with oils from two other Brassicaceae:Physaria floribunda andHeliophilia amplexicaulis) have been grouped into five categories: densipolic acid-rich (Class I); auricolic acid-rich (Class II); lesquerolic acid-rich (Class III); an oil containing a mixture of hydroxy acids (Class IV); and lesquerolic and erucic acid-rich (Class V). The majority of Class I and II triglycerides contain one or two monoestolides at the 1- and 3-glycerol positions and a C18 polyunsaturated acyl group at the 2-position. Most Class III and IV oil triglycerides contain one or two hydroxy acids at the 1- and 3-positions and C18 unsaturated acid at the 2-position. A few of the Class III oils have trace amounts of estolides. The Class V oil triglycerides are mostly pentaacyl triglycerides and contain monestolide and small amounts of diestolide. Our triglyceride structure assignments were supported by1H nuclear magnetic resonance data and mass balances.
Keywords:Estolides            1H NMR            Heliophilia amplexicaulis            hydroxy acids  densipolic  lesquerolic and auricolic acids            Lesquerella spp    lipases            Physaria floribunda
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