Targeted metabolomics of physaria fendleri, an industrial crop producing hydroxy fatty acids

Plant and Cell Physiology

Volumn 55, Issue 3, 2014, Pages 620-633

  Cocuron, Jean Christophe ^a   Anderson, Brooke ^a   Boyd, Alison ^a   Alonso, Ana Paula ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Hydroxy fatty acid; LC MS MS; Lesquerella; Lesquerolic acid; Metabolomics; Physaria fendleri

Indexed keywords

FATTY ACID;

BRASSICACEAE; GENETICS; METABOLISM; METABOLOMICS; PROCEDURES; TANDEM MASS SPECTROMETRY; TRANSGENIC PLANT;

BRASSICACEAE; FATTY ACIDS; METABOLOMICS; PLANTS, GENETICALLY MODIFIED; TANDEM MASS SPECTROMETRY;

EID: 84899102098     PISSN: 00320781     EISSN: 14719053     Source Type: Journal    
DOI: 10.1093/pcp/pcu011     Document Type: Article

References (55)

1. Abbott, T.P., Wu, Y.V., Carlson, K.D., Slodki, M.E. and Kleiman, R. (1994) Isolation and preliminary characterization of Lesquerella fendleri gums from seed, presscake, and defatted meal. J. Agric. Food Chem. 42: 1678-1685
2. Allen, D.K., Ohlrogge, J.B. and Shachar-Hill, Y. (2009) The role of light in soybean seed filling metabolism. Plant J. 58: 220-234
3. Alonso, A.P., Dale, V.L. and Shachar-Hill, Y. (2010a) Understanding fatty acid synthesis in Developing maize embryos using metabolic flux analysis. Metab. Eng. 12: 488-497
4. Alonso, A.P., Goffman, F.D., Ohlrogge, J.B. and Shachar-Hill, Y. (2007) Carbon conversion efficiency and central metabolic fluxes in Developing sunflower (Helianthus annuus L.) embryos. Plant J. 52: 296-308
5. Alonso, A.P., Piasecki, R.J., Wang, Y., LaClair, R.W. and Shachar-Hill, Y. (2010b) Quantifying the labeling and the levels of plant cell wall precursors using ion chromatography tandem mass spectrometry. Plant Physiol. 153: 915-924
6. Alonso, A.P., Val, D.L. and Shachar-Hill, Y. (2011) Central metabolic fluxes in the endosperm of developing maize seeds and their implications for metabolic engineering. Metab. Eng. 13: 96-107
7. Bafor, M., Smith, M.A., Jonsson, L., Stobart, K. and Stymne, S. (1991) Ricinoleic acid biosynthesis and triacylglycerol assembly in microsomal preparations from developing castor-bean (Ricinus communis) endosperm. Biochem. J. 280: 507-514
8. Bajad, S.U., Lu, W., Kimball, E.H., Yuan, J., Peterson, C. and Rabinowitz, J.D. (2006) Separation and quantitation of water soluble cellular metabolites by hydrophilic interaction chromatography-Tandem mass spectrometry. J. Chromatogr. A 1125: 76-88
9. Barclay, A.S., Gentry, H.S. and Jones, Q. (1962) The search of new energy crops II: Lesquerella (Cruciferae) as source of new oilseeds. Econ. Bot. 16: 95-100
10. Baud, S. and Lepiniec, L. (2010) Physiological and developmental regulation of seed oil production. Prog. Lipid Res. 49: 235-249
11. Brahim, K., Stumpf, D.K., Ray, D.T. and Dierig, D.A. (1996) Lesquerella fendleri seed oil content and composition: Harvest date and plant population effects. Ind. Crop Prod. 5: 245-252
12. Browse, J. and Slack, C.R. (1985) Fatty-Acid synthesis in plastids from maturing safflower and linseed cotyledons. Planta 166: 74-80
13. Carlson, K.D., Chaudhry, A. and Bagby, M.O. (1990) Analysis of oil and meal from Lesquerella fendleri seed. J. Amer. Oil Chem. Soc. 67: 438-442
14. Cermak, S.C., Brandon, K.B. and Isbell, T.A. (2006) Synthesis and physical properties of estolides from lesquerella and castor fatty acid esters. Ind. Crop Prod. 23: 54-64
15. Chen, G.Q. (2011) Effective reduction of chimeric tissue in transgenics for the stable genetic transformation of Lesquerella fendleri. Hortscience 46: 86-90
16. Cocuron, J.C. and Alonso, A.P. (2014) Liquid chromatography tandem mass spectrometry for measuring 13C-labeling in intermediaries of the glycolysis and pentose-phosphate pathway. Methods Mol. Biol. 1090: 131-142
17. Cruz, J.A., Emery, C., Wust, M., Kramer, D.M. and Lange, B.M. (2008) Metabolite profiling of Calvin cycle intermediates by HPLC-MS using mixed-mode stationary phases. Plant J. 55: 1047-1060
18. Dierig, D.A., Wang, G., McCloskey, W.B., Thorp, K.R., Isbell, T.A., Ray, D.T. et al. (2011) Lesquerella: New crop development and commercialization in the US. Ind. Crop Prod. 34: 1381-1385
19. Donaldson, R.P. (1977) Accumulation of free ricinoleic acid in germinating castor bean endosperm. Plant Physiol. 59: 1064-1066
20. Fatland, B., Anderson, M., Nikolau, B.J. and Wurtele, E.S. (2000) Molecular biology of cytosolic acetyl-CoA generation. Biochem. Soc. Trans. 28: 593-595
21. Goffman, F.D., Alonso, A.P., Schwender, J., Shachar-Hill, Y. and Ohlrogge, J.B. (2005) Light enables a very high efficiency of carbon storage in Developing embryos of rapeseed. Plant Physiol. 138: 2269-2279
22. Grimble, G.K., Barker, H.M. and Taylor, R.H. (1983) Chromatographic analysis of sugars in physiological fluids by postcolumn reaction with cuprammonium: A new and highly sensitive method. Anal. Biochem. 128: 422-428
23. Gu, L., Jones, A.D. and Last, R.L. (2007) LC-MS/MS assay for protein amino acids and metabolically related compounds for large-scale screening of metabolic phenotypes. Anal. Chem. 79: 8067-8075
24. Hill, L.M. and Smith, A.M. (1991) Evidence that glucose-6-phosphate is imported as the substrate for starch synthesis by the plastids of developing pea embryos. Planta 185: 91-96
25. Hills, M.J. (2004) Control of storage-product synthesis in seeds. Curr. Opin. Plant Biol. 7: 302-308
26. Huck, J.H.J., Struys, E.A., Verhoeven, N.M., Jakobs, C. and Van Der Knaap, M.S. (2003) Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: Application to transaldolase deficiency. Clin. Chem. 49: 1375-1380
27. Hunsaker, D.J., Nakayama, F.S., Dierig, D.A. and Alexander, W.L. (1998) Lesquerella seed production: Water requirement and management. Ind. Crop Prod. 8: 167-182
28. Isbell, T.A., Mund, M.S., Evangelista, R.L. and Dierig, D.A. (2008) Method for analysis of fatty acid distribution and oil content on a single Lesquerella fendleri seed. Ind. Crop Prod. 28: 231-235
29. Kang, F. and Rawsthorne, S. (1996) Metabolism of glucose-6-phosphate and utilization of multiple metabolites for fatty acid synthesis by plastids from developing oilseed rape embryos. Planta 199: 321-327
30. Kato, Y. and Numajiri, Y. (1991) Chloride attachment negative-ion mass spectra of sugars by combined liquid chromatography and atmospheric pressure chemical ionization mass spectrometry. J. Chromatogr. 562: 81-97
31. Kelebek, H. and Selli, S. (2011) Determination of volatile, phenolic, organic acid and sugar components in a Turkish cv. Dortyol (Citrus sinensis L. Osbeck) orange juice. J. Sci. Food Agric. 91: 1855-1862
32. Kleppinger-Sparace, K.F., Stahl, R.J. and Sparace, S.A. (1992) Energy requirements for fatty-Acid and glycerolipid biosynthesis from acetate by isolated pea root plastids. Plant Physiol. 98: 723-727
33. Koubaa, M., Cocuron, J-C., Thomasset, B. and Alonso, A.P. (2013) Highlighting the tricarboxilic acid cycle: Liquid and gas chromatography-mass spectrometry analyses of 13C-labeled organic acids. Anal. Biochem. 436: 151-159
34. Koubaa, M., Mghaieth, S., Thomasset, B. and Roscher, A. (2012) Gas chromatography-mass spectrometry analysis of 13C labeling in sugars for metabolic flux analysis. Anal. Biochem. 425: 183-188
35. Luo, B., Groenke, K., Takors, R., Wandrey, C. and Oldiges, M. (2007) Simultaneous determination of multiple intracellular metabolites in glycolysis, pentose phosphate pathway and tricarboxylic acid cycle by liquid chromatography-mass spectrometry. J. Chromatogr. A 1147: 153-164
36. Moon, H., Smith, M.A. and Kunst, L. (2001) A condensing enzyme from the seeds of Lesquerella fendleri that specifically elongates hydroxy fatty acids. Plant Physiol. 127: 1635-1643
37. Narayan, S.B., Ditewig-Meyers, G., Graham, K.S., Scott, R. and Bennett, M.J. (2011) Measurement of plasma amino acids by utraperformance liquid chromatography. Clin. Chem. Lab. Med. 49: 1177-1185
38. Nelson, J.M., Dierig, D.A. and Nakayama, F.S. (1996) Planting date and nitrogen fertilization effects on lesquerella production. Ind. Crop. Prod. 5: 217-222
39. Neuhaus, H.E., Batz, O., Thom, E. and Scheibe, R. (1993) Purification of highly intact plastids from various heterotrophic plant tissues: Analysis of enzymic equipment and precursor dependency for starch biosynthesis. Biochem. J. 296: 395-401
40. Nikolau, B.J., Oliver, D.J., Schnable, P.S. and Wurtele, E.S. (2000) Molecular biology of acetyl-CoA metabolism. Biochem. Soc. Trans. 28: 591-593
41. Ohlrogge, J.B., Ruuska, S.A. and Schwender, J. (2004) The capacity of green oilseeds to utilize photosynthesis to drive biosynthetic processes. Plant Physiol. 136: 2700-2709
42. Patti, G.J., Yanes, O. and Siuzdak, G. (2012) Innovation: Metabolomics: The apogee of the omics trilogy. Nat. Rev. Mol. Cell Biol. 13: 263-269
43. Puppala, N., Fowler, J.L., Jones, T.L., Gutschick, V. and Murray, L. (2005) Evapotranspiration, yield, and water-use efficiency responses of Lesquerella fendleri at different growth stages. Ind. Crop Prod. 21: 33-47
44. Reed, D.W., Taylor, D.C. and Covello, P.S. (1997) Metabolism of hydroxy fatty acids in Developing seeds in the genera Lesquerella (Brassicaceae) and Linum (Linaceae). Plant Physiol. 114: 63-68
45. Rogatsky, E., Jayatillake, H., Goswami, G., Tomuta, V. and Stein, D. (2005) Sensitive LC MS quantitative analysis of carbohydrates by Cs+ attachment. J. Amer. Soc. Mass Spectrom. 16: 1805-1811
46. Ruiz-Matute, A.I., Hernandez-Hernandez, O., Rodriguez-Sanchez, S., Sanz, M.L. and Martinez-Castro, I. (2011) Derivatization of carbohydrates for GC and GC-MS analyses. J. Chromatogr. B 879: 1226-1240
47. Schwender, J., Goffman, F., Ohlrogge, J.B. and Shachar-Hill, Y. (2004) Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds. Nature 432: 779-782
48. Schwender, J., Shachar-Hill, Y. and Ohlrogge, J.B. (2006) Mitochondrial metabolism in Developing embryos of Brassica napus. J. Biol. Chem. 281: 34040-34047
49. Skarjinskaia, M., Svab, Z. and Maliga, P. (2003) Plastid transformation in Lesquerella fendleri, an oilseed Brassicacea. Transgenic Res. 12: 115-122
50. Skarzhinskaya, M., Landgren, M. and Glimelius, K. (1996) Production of intertribal somatic hybrids between Brassica napus L and Lesquerella fendleri (Gray) wats. Theor. Appl. Genet. 93: 1242-1250
51. Smith, R.G., Gauthier, D.A., Dennis, D.T. and Turpin, D.H. (1992) Malate-dependent and pyruvate-dependent fatty-Acid synthesis in leukoplastids from developing castor endosperm. Plant Physiol. 98: 1233-1238
52. Thiele, B., Stein, N., Oldiges, M. and Hofmann, D. (2012) Direct analysis of underivatized amino acids in plant extracts by LC-MS-MS. Methods Mol. Biol. 828: 317-328
53. Wang, W.Y., Wang, C.G., Huang, B.L. and Huang, B.Q. (2008) Agrobacterium tumefaciens-mediated transformation of Lesquerella fendleri L., a potential new oil crop with rich lesquerolic acid. Plant Cell Tiss. Org. 92: 165-171
54. Wu, Y.V. and Abbott, T.P. (1996) Enrichment of gum content from Lesquerella fendleri seed coat by air classification. Ind. Crop Prod. 5: 47-51
55. Wu, Y.V. and Hojilla-Evangelista, M.P. (2005) Lesquerella fendleri protein fractionation and characterization. J. Amer. Oil Chem. Soc. 82: 53-56