Characterization of sphingolipids from sunflower seeds with altered fatty acid composition

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 23, 2011, Pages 12486-12492

  Salas, Joaquín J ^a   Markham, Jonathan E ^b   Martínez Force, Enrique ^a   Garcés, Rafael ^a  

^a INSTITUTO DE LA GRASA   (Spain)

^b DONALD DANFORTH PLANT SCIENCE CENTER   (United States)

Author keywords

Helianthus annuus; seed kernel; sphingoid bases; Sphingolipids; sunflower mutant

Indexed keywords

BASE COMPOSITION; CERAMIDES; FATTY ACID COMPOSITION; FATTY ACID SYNTHESIS; HELIANTHUS ANNUUS; LONG-CHAIN FATTY ACIDS; PLANT TISSUES; SPHINGOID BASIS; SPHINGOLIPIDS; SUNFLOWER MUTANT; SUNFLOWER SEEDS;

AMIDES; LIPIDS; MASS SPECTROMETRY; SEED; SUGARS; TISSUE;

FATTY ACIDS;

CERAMIDE; FATTY ACID; SPHINGOLIPID;

ARTICLE; CHEMISTRY; GENETICS; MASS SPECTROMETRY; MUTATION; PLANT SEED; SUNFLOWER;

CERAMIDES; FATTY ACIDS; HELIANTHUS; MASS SPECTROMETRY; MUTATION; SEEDS; SPHINGOLIPIDS;

EID: 83055169924     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf203366z     Document Type: Article

References (34)

1. Karlsson, K. A. Sphingolipid long chain bases Lipids 1970, 5, 878-891
2. Sperling, P.; Heinz, E. Plant sphingolipids: Structural diversity, biosynthesis, first genes and functions Biochim. Biophys. Acta 2003, 1632, 1-15
3. Hanada, K. Serine palmitoyltransferase, a key enzyme of sphingolipid metabolism Biochim. Biophys. Acta 2003, 1632, 16-30
4. Obeid, L. M.; Okamoto, Y.; Mao, C. Yeast sphingolipids: Metabolism and biology Biochim. Biophys. Acta 2002, 1585, 163-171
5. Lynch, D. V.; Dunn, T. M. An introduction to plant sphingolipids and a review of recent advances in understanding their metabolism and function New Phytol. 2004, 161, 677-702
6. Chen, M.; Markham, J. E.; Dietrich, C. R.; Jaworski, J. G.; Cahoon, E. B. Sphingolipid long-chain base hydroxylation is important for growth and regulation of sphingolipid content and composition in arabidopsis Plant Cell 2008, 20, 1862-1878
7. Ryan, P. R.; Liu, Q.; Sperling, P.; Dong, B.; Franke, S.; Delhaize, E. A higher plant D8 sphingolipid desaturase with a preference for (Z)-isomer formation confers aluminum tolerance to yeast and plants Plant Physiol. 2007, 144, 1968-1977
8. Abrahamsson, S.; Pascher, I.; Larsson, K; Karlsson, K.-A. Molecular arrangements in glycosphingolipids Chem. Phys. Lipids 1972, 8, 152-179
9. Kaul, K.; Lester, R. L. Isolation of six novel phosphoinositol containing sphingolipids from tobacco leaves Biochemistry 1978, 17, 3569-3575
10. Chen, M.; Han, G.; Dietrich, C. R.; Dunn, T. M.; Cahoon, E. B. The essential nature of sphingolipids in plants as revealed by the functional identification and characterization of the arabidopsis LCB1 subunit of serine palmitoyltransferase Plant Cell 2006, 12, 3576-3593
11. Markham, J. E.; Li, J.; Cahoon, E. B.; Jaworski, J. G. Separation and identification of major plant sphingolipid classes from leaves J. Biol. Chem. 2006, 281, 22684-22694
12. Heinz, E. Plant glycolipids: Structure, isolation and analysis. In Advances in Lipid Methodology I; The Oily Press: Dundee, United Kingdom, 1996; pp 211-332.
13. Youl, J. J.; Bacic, A.; Oxley, D. Arabinogalactan-proteins from Nicotiana alata and Pyrus communis contain glycosylphosphatidylinositol membrane anchors Proc. Natl. Acad. Soc. U.S.A. 1998, 95, 7921-7926
14. Lynch, D. V. Sphingolipids. In Lipid Metabolism in Plants; CRC Press: Boca Raton, FL, 1993; pp 211-332.
15. Markham, J. E.; Jaworski, J. G. Rapid measurement of sphingolipids from Arabidopsis thaliana by reversed-phase high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry Rapid Commun. Mass Spectrom. 2007, 21, 1304-1314
16. Berra, B.; Colombo, I.; Sottocornola, E.; Giacosa, A. Dietary sphingolipids in colorectal cáncer prevention Eur. J. Cancer Prev. 2002, 11, 193-197
17. Ahn, E. H.; Schroeder, J. J. Bioactive sphingolipids are constituents of soy and dairy products J. Food Sci. 2002, 67, 522-524
18. Moreno-Pérez, A. J.; Martínez-Force, E.; Garcés, R.; Salas, J. J. Sphingolipid base modifying enzymes in sunflower (Helianthus annuus): cloning and characterization of a C4-hydroxylase gene and a new paralogous Δ8-desaturase gene J. Plant Physiol. 2011, 168, 831-839
19. Garcés, R.; García, J. M.; Mancha, M. Lipid characterization in seeds of a high oleic acid sunflower mutant Phytochemistry 1989, 28, 2597-2600
20. Álvarez-Ortega, R.; Cantisán, S.; Martínez-Force, E.; Garcés, R. Characterization of polar and non-polar seed lipid classes from highly saturated fatty acid sunflower mutants Lipids 1997, 32, 833-837
21. Sperling, P.; Zahringer, U.; Heinz, E. A sphingolipid desaturase from higher plants: identification of a new cytochrome b5 fusion protein J. Biol. Chem. 1998, 273, 28590-28596
22. Bonaventure, G.; Salas, J. J.; Pollard, M. R.; Ohlrogge, J. B. Disruption of the FatB gene in Arabidopsis demonstrates an essential role of saturated fatty acids in plant growth Plant Cell 2003, 15, 1020-1033
23. Markham, J. E.; Li, J.; Cahoon, E. B.; Jaworski, J. E. Separation and Identification of major plant sphingolipid classes from Leaves J. Biol. Chem. 2006, 281, 22684-22694
24. Coursol, S.; Fan, L. M.; Le Stunff, H.; Spiegel, S.; Gilroy, S.; Assman, S. M. Sphingolipid signaling in Arabidopsis guard cells involves heterotrimeric G proteins Nature 2003, 423, 651-654
25. Liang, H.; Yao, N.; Song, J. T.; Luo, S.; Lu, H.; Greenberg, J. T. Ceramide phosphorylation modulates programmed cell death in plants Genes Dev. 2003, 17, 2636-2641
26. González-Mellado, D.; von Wettstein-Knowles, P.; Garcés, R.; Martínez-Force, E. The role of β-ketoacyl-acyl carrier protein synthase III in the condensation steps of fatty acid biosynthesis in sunflower Planta 2010, 231, 1277-1289
27. Salas, J. J.; Youssar, L.; Martínez-Force, E.; Garcés, R. The biochemical characterization of a high-stearic acid sunflower mutant reveals the coordinated regulation of stearoyl-acyl carrier protein desaturases Plant Physiol. Biochem. 2008, 46, 109-116
28. Cantisán, S.; Martínez-Force, E.; Álvarez-Ortega, R.; Garcés, R. Lipid characterization in vegetative tissues of high saturated fatty acid sunflower mutants J. Agric. Food Chem. 1999, 47, 78-82
29. Turnham, E.; Northcote, D. H. Changes in the activity of acetyl-CoA carboxylase during rape-seed formation Biochem. J. 1983, 212, 223-229
30. Salas, J. J.; Martínez-Force, E.; Garcés, R. Very long chain fatty acid synthesis in sunflower kernels J. Agric. Food Chem. 2005, 53, 2710-2716
31. Mitchell, A. G.; Martin, C. E. Fah1p, a Saccharomyces cerevisiae cytochromeb5 fusion protein, and its Arabidopsis thaliana homolog that lacks the cytochromeb5 domain both function in the α-hydroxylation of sphingolipid-associated very long chain fatty acids J. Biol. Chem. 1997, 272, 28281-28288
32. Imai, H.; Yamamoto, K.; Shibahara, A.; Miyatani, S.; Nakayama, T. Determining double-bond positions in monoenoic 2-hydroxy fatty acids of glucosylceramides by gas chromatography-mass spectrometry Lipids 2000, 35, 233-236
33. Ohnishi, M.; Fujino, Y. Sphingolipids in immature and mature soybeans Lipids 1982, 17, 803-810
34. Imai, H.; Morimoto, Y.; Tamura, K. Sphingoid base composition of monoglucosylceramide in Brassicaceae J. Plant Physiol. 2000, 157, 453-456