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.
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References
Barclay, A.S., H.S. Gentry and Q. Jones,Econ. Bot. 16:95 (1962).
Miller, R.W., F.R. Earle and I.A. Wolff,J. Am. Oil Chem. Soc. 42:817 (1965).
Senft, D.,Agric. Res. 40:16 (1992).
Mikolajczak, K.L., F.R. Earle and I.A. Wolff,J. Am. Oil Chem. Soc. 39:78 (1962).
Bender, R.G., and A. Lee,J. Org. Chem. 31:1477 (1966).
Payne-Wahl, K., R.D. Plattner, G.F. Spencer and R. Kleiman,Lipids 14:601 (1979).
Hayes, D.G., and R. Kleiman,J. Am. Oil Chem. Soc. 69:982 (1992).
Bartle, K.D., and T.A. Clifford,Advances in Applied Lipid Research, edited by F.B. Padley, JAI Press, London, 1992, p. 217.
Raynor, M.W., K.D. Bartle, A.A. Clifford, J.M. Chalmers, T. Katase, C.A. Rouse, R.E. Markides and M.L. Lee,J. Chrom. 505:179 (1990).
Berg, B.E., E.M. Hansen, S. Gjorven and T. Greibrokk,J. High Res. Chrom. 16:358 (1993).
Kleiman, R., G. Spencer, F.R. Earle, H.J. Nieschlag and A.S. Barclay,Lipids 7:660 (1972).
Plattner, R.D., K. Payne-Wahl, L.W. Tjarks and R. Kleiman, Ibid.:576 (1979).
Payne-Wahl, K., and R. Kleiman,J. Am. Oil Chem. Soc. 60:1011 (1983).
Aitzetmuller, K., Y. Xin, G. Werner and M. Gronheim,J. Chrom. 603:165 (1992).
Sprecher, H.W., R. Maier, M. Barber and R.T. Holman,Biochemistry 4:1856 (1965).
Mikolajczak, K.L., C.R. Smith Jr. and I.A. Wolff,Lipids 3:215 (1968).
Powell, R.G., R. Kleiman and C.R. Smith Jr., Ibid.:450 (1969).
Phillips, B.E., and C.R. Smith Jr.,Biochim. Biophys. Acta. 218:71 (1970).
Madrigal, R.V., and C.R. Smith,Lipids 17:650 (1982).
Morris, L.J., and S.W. Hall, Ibid.:188 (1965).
Rajiah, A., M.R. Subbaram and K.T. Achaya, Ibid.:87 (1976).
Mikolajczak, K.L., and C.R. Smith Jr.,Biochim. Biophys. Acta 152:244 (1968).
Herbin, G.A., and P.A. Robins,Phytochemistry 7:1325 (1968).
Corrigan, D., R.F. Timoney and D.M.X. Donnelly, Ibid.:907 (1978).
Fransch, R.A., L.G. Wells and P.T. Holland, Ibid.:1617 (1978).
Tulloch, A.P., and L. Bergter, Ibid.:2711 (1981).
Schulten, H.R., N. Simmleit and H.H. Rump,Chem. Phys. Lipids 41:209 (1986).
Gunthardt-Goerg, M.S.,Eur. J. For. Path. 16:400 (1986).
Matsumura, S., and J. Takahashi,Makromol. Chem. Rapid Commun. 7:369 (1986).
Makita, A., T. Nihira and Y. Yamada,Tetrah. Lett. 28:805 (1987).
Neissner, V.R.,Fat. Sci. Technol. 82:183 (1980).
Chaudhry, A., R. Kleiman and K.D. Carlson,J. Am. Oil Chem. Soc. 67:863 (1990).
Brockerhoff, H., and M. Yurkowski,J. Lipid Res. 7:62 (1966).
Rollins, R.C., and E.A. Shaw,The Genus Lesquerella (Cruciferae) in North America, Harvard University Press, Cambridge, 1973.
Mulligan, G.A.,Can. J. Bot. 46:735 (1968).
Rollins, R.C.,Rhodora 41:392 (1939).
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Hayes, D.G., Kleiman, R. & Phillips, B.S. The triglyceride composition, structure, and presence of estolides in the oils ofLesquerella and related species. J Am Oil Chem Soc 72, 559–569 (1995). https://doi.org/10.1007/BF02638857
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DOI: https://doi.org/10.1007/BF02638857