Quantifi cation of sterol lipids in plants by quadrupole time-of-fl ight mass spectrometry

Journal of Lipid Research

Volumn 52, Issue 5, 2011, Pages 1039-1054

  Wewer, Vera ^a   Dombrink, Isabel ^a   Vom Dorp, Katharina ^a   Dörmann, Peter ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Arabidopsis; Campesterol; Cholesterol; Phosphate limitation; Phytosterol; Sitosterol; Stigmasterol

Indexed keywords

ACYLATED STEROL GLYCOSIDE; FREE STEROL; PHYTOSTEROL; STEROL ESTER; STEROL GLYCOSIDE; UNCLASSIFIED DRUG; CAMPESTEROL; CHOLESTEROL; DRUG DERIVATIVE; LIPID; SITOSTEROL; SITOSTEROL DERIVATIVE; STEROL; STIGMASTEROL;

ARABIDOPSIS; ARTICLE; CONTROLLED STUDY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID ANALYSIS; MASS SPECTROMETRY; NONHUMAN; PHYTOCHEMISTRY; PLANT LEAF; PLANT ROOT; PRIORITY JOURNAL; QUADRUPOLE TIME OF FLIGHT MASS SPECTROMETRY; QUANTITATIVE ANALYSIS; SENSITIVITY ANALYSIS; VALIDITY; CHEMISTRY; METHODOLOGY; PLANT; THIN LAYER CHROMATOGRAPHY;

ARABIDOPSIS; CHOLESTEROL; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, THIN LAYER; LIPIDS; MASS SPECTROMETRY; PHYTOSTEROLS; PLANTS; SITOSTEROLS; STEROLS; STIGMASTEROL;

EID: 79955008153     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.D013987     Document Type: Article

References (51)

1. Joyard , J. , M. A. Block , A. Malhèrbe , E. Maréchal , and R. Douce. 1994. Origin and synthesis of galactolipid and sulfolipid head groups In Lipid Metabolism In Plants. T. S. J. Moore , editor. CRC Press , Boca Raton (FL). 231-258.
2. Benning , C. , and H. Ohta. 2005. Three enzyme systems for galactoglycerolipid biosynthesis are coordinately regulated in plants. J. Biol. Chem. 280 : 2397-2400. (Pubitemid 40189336)
3. Markham , J. E. , and J. G. Jaworski. 2007. Rapid measurement of sphingolipids from Arabidopsis thaliana by reversed-phase highperformance liquid chromatography coupled to electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 21 : 1304-1314. (Pubitemid 46506586)
4. Markham , J. E. , J. Li , E. B. Cahoon , and J. G. Jaworski. 2006. Separation and identification of major plant sphingolipid classes from leaves. J. Biol. Chem. 281 : 22684-22694.
5. Benveniste , P. 2004. Biosynthesis and accumulation of sterols. Annu. Rev. Plant Biol. 55 : 429-457. (Pubitemid 38940939)
6. Fujioka , S. , S. Takatsuto , and S. Yoshida. 2002. An early C-22 oxidation branch in the brassinosteroid biosynthetic pathway. Plant Physiol. 130 : 930-939. (Pubitemid 35224793)
7. Kemp , R. J. , and E. I. Mercer. 1968. The sterol esters of maize seedlings. Biochem. J. 110 : 111-118.
8. Zinser , E. , F. Paltauf , and G. Daum. 1993. Sterol composition of yeast organelle membranes and subcellular distribution of enzymes involved in sterol metabolism. J. Bacteriol. 175 : 2853-2858. (Pubitemid 23148716)
9. Banas , A. , A. S. Carlsson , B. Huang , M. Lenman , W. Banas , M. Lee , A. Noiriel , P. Benveniste , H. Schaller , P. Bouvier-Navé , et al. 2005. Cellular sterol ester synthesis in plants is performed by an enzyme (phospholipid: Sterol acyltransferase) different from the yeast and mammalian acyl-CoA: Sterol acyltransferases. J. Biol. Chem. 280 : 34626-34634. (Pubitemid 41504593)
10. Chen , Q. , L. Steinhauer , J. Hammerlindl , W. Keller , and J. Zou. 2007. Biosynthesis of phytosterol esters: Identification of a sterol O-acyltransferase in Arabidopsis. Plant Physiol. 145 : 974-984. (Pubitemid 350127599)
11. Bouvier-Navé , P. , A. Berna , A. Noiriel , V. Compagnon , A. S. Carlsson , A. Banas , S. Stymne , and H. Schaller. 2010. Involvement of the phospholipid sterol acyltransferase 1 in plant sterol homeostasis and leaf senescence. Plant Physiol. 152 : 107-119.
12. Grunwald , C. 1971. Effects of free sterols, steryl ester, and steryl glycoside on membrane permeability. Plant Physiol. 48 : 653-655.
13. Grille , S. , A. Zaslawski , S. Thiele , J. Plat , and D. Warnecke. 2010. The functions of steryl glycosides come to those who wait: Recent advances in plants, fungi, bacteria and animals. Prog. Lipid Res. 49 : 262-288.
14. Warnecke , D. C. , M. Baltrusch , F. Buck , F. P. Wolter , and E. Heinz. 1997. UDP-glucose: Sterol glucosyltransferase: Cloning and functional expression in Escherichia coli. Plant Mol. Biol. 35 : 597-603. (Pubitemid 27433936)
15. DeBolt , S. , W. R. Scheible , K. Schrick , M. Auer , F. Beisson , V. Bischoff , P. Bouvier-Navé , A. Carroll , K. Hematy , Y. Li , et al. 2009. Mutations in UDP-glucose: Sterol glucosyltransferase in Arabidopsis cause transparent testa phenotype and suberization defect in seeds. Plant Physiol. 151 : 78-87.
16. Frasch , W. , and D. Grunwald. 1976. Acylated steryl glycoside synthesis in seedlings of Nicotiana tabacum L. Plant Physiol. 58 : 744-748.
17. Warnecke , D. , R. Erdmann , A. Fahl , B. Hube , F. Müller , T. Zank , U. Zähringer , and E. Heinz. 1999. Cloning and functional expression of UGT genes encoding sterol glucosyltransferases from Saccharomyces cerevisiae , Candida albicans , Pichia pastoris , and Dictyostelium discoideum. J. Biol. Chem. 274 : 13048-13059.
18. Griebel , T. , and J. Zeier. 2010. A role for b -sitosterol to stigmasterol conversion in plant-pathogen interactions. Plant J. 63 : 254-268.
19. Wunder , C. , Y. Churin , F. Winau , D. Warnecke , M. Vieth , B. Lindner , U. Zähringer , H-J. Mollenkopf , E. Heinz , and T. Meyer. 2006. Cholesterol glucosylation promotes immune evasion by Helicobacter pylori. Nat. Med. 12 : 1030-1038. (Pubitemid 44353384)
20. Oku , M. , D. Warnecke , T. Noda , F. Müller , E. Heinz , H. Mukaiyama , N. Kato , and Y. Sakai. 2003. Peroxisome degradation requires catalytically active sterol glucosyltransferase with a GRAM domain. EMBO J. 22 : 3231-3241. (Pubitemid 36834854)
21. Dörmann , P. , and C. Benning. 2002. Galactolipids rule in seed plants. Trends Plant Sci. 7 : 112-118. (Pubitemid 36726436)
22. Tjellström , H. , L. I. Hellgren , A. Wieslander , and A. S. Sandelius. 2010. Lipid asymmetry in plant plasma membranes: Phosphate defi ciency-induced phospholipid replacement is restricted to the cytosolic leafl et. FASEB J. 24 : 1128-1138.
23. Christie , W. , S. Gill , J. Nordback , Y. Itabashi , S. Sanda , and A. Slabas. 1998. New procedures for rapid screening of leaf lipid components from Arabidopsis. Phytochem. Anal. 9 : 53-57. (Pubitemid 28161828)
24. Andersson , M. X. , K. E. Larsson , H. Tjellström , C. Liljenberg , and A. S. Sandelius. 2005. Phosphate-limited oat. The plasma membrane and the tonoplast as major targets for phospholipid-to-glycolipid replacement and stimulation of phospholipases in the plasma membrane. J. Biol. Chem. 280 : 27578-27586. (Pubitemid 41076869)
25. Wenk , M. 2005. The emerging field of lipidomics. Nat. Rev. Drug Discov. 4 : 594-610. (Pubitemid 40975712)
26. Welti , R. , W. Li , M. Li , Y. Sang , H. Biesiada , H-E. Zhou , C. Rajashekar , T. Williams , and X. Wang. 2002. Profiling membrane lipids in plant stress responses. Role of phospholipase D a in freezing-induced lipid changes in Arabidopsis. J. Biol. Chem. 277 : 31994-32002. (Pubitemid 34969009)
27. Devaiah , S. P. , M. R. Roth , E. Baughman , M. Li , P. Tamura , R. Jeannotte , R. Welti , and X. Wang. 2006. Quantitative profi ling of polar glycerolipid species from organs of wild-type Arabidopsis and a PHOSPHOLIPASE Da1 knockout mutant. Phytochemistry. 67 : 1907-1924. (Pubitemid 44291405)
28. Ejsing , C. S. , J. L. Sampaio , V. Surendranath , E. Duchoslav , K. Ekroos , R. W. Klemm , K. Simons , and A. Shevchenko. 2009. Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry. Proc. Natl. Acad. Sci. U S A. 106 : 2136-2141.
29. Karu , K. , M. Hornshaw , G. Woffendin , K. Bodin , M. Hamberg , G. Alvelius , J. Sjövall , J. Turton , Y. Wang , and W. Griffiths. 2007. Liquid chromatography-mass spectrometry utilizing multi-stage fragmentation for the identification of oxysterols. J. Lipid Res. 48 : 976-987. (Pubitemid 46562412)
30. Liebisch , G. , M. Binder , R. Schifferer , T. Langmann , B. Schulz , and G. Schmitz. 2006. High throughput quantifi cation of cholesterol and cholesteryl ester by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Biochim. Biophys. Acta. 1761 : 121-128.
31. Honda , A. , K. Yamashita , H. Miyazaki , M. Shirai , T. Ikegami , G. Xu , M. Numazawa , T. Hara , and Y. Matsuzaki. 2008. Highly sensitive analysis of sterol profi les in human serum by LC-ESI-MS/MS. J. Lipid Res. 49 : 2063-2073.
32. Johnson , D. W. , H. J. ten Brink , and C. Jakobs. 2001. A rapid screening procedure for cholesterol and dehydrocholesterol by electrospray ionization tandem mass spectrometry. J. Lipid Res. 42 : 1699-1705. (Pubitemid 33020103)
33. Jiang , X. , D. Ory , and X. Han. 2007. Characterization of oxysterols by electrospray ionization tandem mass spectrometry after one-step derivatization with dimethylglycine. Rapid Commun. Mass Spectrom. 21 : 141-152. (Pubitemid 46095472)
34. Murashige , T. , and F. Skoog. 1962. A revised medium for rapid growth and bio assays with tobacco tissue cultures. Physiol. Plant. 15 : 473-497.
35. Estelle , M. A. , and C. Somerville. 1987. Auxin-resistant mutants of Arabidopsis thaliana with an altered morphology. Mol. Gen. Genet. 206 : 200-206.
36. Gaude , N. , Y. Nakamura , W-R. Scheible , H. Ohta , and P. Dörmann. 2008. Phospholipase C5 (NPC5) is involved in galactolipid accumulation during phosphate limitation in leaves of Arabidopsis. Plant J. 56 : 28-39.
37. Delhaize , E. , and P. J. Randall. 1995. Characterization of a phosphate- accumulator mutant of Arabidopsis thaliana. Plant Physiol. 107 : 207-213.
38. Hamburger , D. , E. Rezzonico , J. MacDonald-Comber Petétot , C. Somerville , and Y. Poirier. 2002. Identification and characterization of the Arabidopsis PHO1 gene involved in phosphate loading to the xylem. Plant Cell. 14 : 889-902. (Pubitemid 34519610)
39. Iga , D. P. , S. Iga , R. R. Schmidt , and M-C. Buzasc. 2005. Chemical synthesis of cholesteryl beta-D-galactofuranoside and -pyranoside. Carbohydr. Res. 340 : 2052-2054. (Pubitemid 41033072)
40. Buseman , C. M. , P. Tamura , A. A. Sparks , E. J. Baughman , S. Maatta , J. Zhao , M. R. Roth , S. W. Esch , J. Shah , T. D. Williams , et al. 2006. Wounding stimulates the accumulation of glycerolipids containing oxophytodienoic acid and dinor-oxophytodienoic acid in Arabidopsis leaves. Plant Physiol. 142 : 28-39. (Pubitemid 44412226)
41. Dörmann , P. , S. Hoffmann-Benning , I. Balbo , and C. Benning. 1995. Isolation and characterization of an Arabidopsis mutant deficient in the thylakoid lipid digalactosyl diacylglycerol. Plant Cell. 7 : 1801-1810. (Pubitemid 3019799)
42. Schaller , H. , B. Grausem , P. Benveniste , M-L. Chye , C-T. Tan , Y-H. Song , and N-H. Chua. 1995. Expression of the Hevea brasiliensis (H.B.K.) Müll. Arg. 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1 in tobacco results in sterol overproduction. Plant Physiol. 109 : 761-770. (Pubitemid 3009544)
43. Li , Y. L. , X. Su , P. D. Stahl , and M. L. Gross. 2007. Quantification of diacylglycerol molecular species in biological samples by electrospray ionization mass spectrometry after one-step derivatization. Anal. Chem. 79 : 1569-1574.
44. Vassel , B. , and W. G. Skelly. 1963. N-Chlorobetainyl chloride. Org Synth. 4 : 154.
45. Ejsing , C. S. , E. Duchoslav , J. Sampaio , K. Simons , R. Bonner , C. Thiele , K. Ekroos , and A. Shevchenko. 2006. Automated identification and quantifi cation of glycerophospholipid molecular species by multiple precursor ion scanning. Anal. Chem. 78 : 6202-6214. (Pubitemid 44360134)
46. Brügger , B. , G. Erben , R. Sandhoff , F. T. Wieland , and W. D. Lehmann. 1997. Quantitative analysis of biological membrane lipids at the low picomole level by nano-electrospray ionization tandem mass spectrometry. Proc. Natl. Acad. Sci. U S A. 94 : 2339-2344. (Pubitemid 27136876)
47. Han , X. , and R. Gross. 2001. Quantitative analysis and molecular species fi ngerprinting of triacylglyceride molecular species directly from lipid extracts of biological samples by electrospray ionization tandem mass spectrometry. Anal. Biochem. 295 : 88-100. (Pubitemid 32721744)
48. Hutchins , P. M. , R. M. Barkley , and R. C. Murphy. 2008. Separation of cellular nonpolar neutral lipids by normal-phase chromatography and analysis by electrospray ionization mass spectrometry. J. Lipid Res. 49 : 804-813.
49. Gachotte , D. , R. Meens , and P. Benveniste. 1995. An Arabidopsis mutant deficient in sterol biosynthesis: Heterologous complementation by ERG3 encoding a D 7 -sterol-C-5-desaturase from yeast. Plant J. 8 : 407-416.
50. Poirier , Y. , S. Thoma , C. Somerville , and J. Schiefelbein. 1991. Mutant of Arabidopsis deficient in sylem loading of phosphate. Plant Physiol. 97 : 1087-1093. (Pubitemid 21914331)
51. Dyas , L. , and L. Goad. 1993. Steryl fatty acylesters in plants. Phytochemistry. 34 : 17-29.