Quantification of Free Sterols, Sterol Esters, Sterol Glucosides and Acylated Sterol Glucosides in Plants by
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1 Quantification of Free Sterols, Sterol Esters, Sterol Glucosides and Acylated Sterol Glucosides in Plants by Q-TOF Mass Spectrometry Vera Wewer and Peter Dörmann Seville, Spain, July 2012 Institute of Molecular Physiology and Biotechnology of Plants (IMBIO) University of Bonn
2 Phytosterols: Structural Variety Cholesterol: the most abundant sterol in animals In plants, β-sitosterol and stigmasterol are predominent. Campesterol is the precursor for brassinosteroid synthesis. Ergosterol, a fungal sterol
3 Conjugated Sterol lipids
4 Sterol Distribution in the Plant Cell Free Sterols (FS) HO Sterol Esters (SE) Sterol Glucosides (SG) Acylated Sterol Glucosides (ASG)
5 The need to develop a comprehensive method for sterol measurements Changes of sterol lipids: Abiotic stress: -P, -N, senescence,... Biotic stress: pathogens (bacteria, fungi), symbiotic interactions (mycorrhiza, nodulation) Traditional method: TLC separation + quantification of sterols or fatty acids by GC or GC-MS
6 Strategy to measure all 4 sterol lipid classes Direct infusion MS/MS similar to the lipidomics measurements by Ruth Welti Avoid time consuming LC procedures Nanospray (low sample amount): 1 µ/min Lipid enrichment prior to MS: SPE with silica columns Use two internal standards (small, large) to correct for size dependence of signal Use saturated standards to measure the plant sterols (which are unsaturated)
7 Sterol Analysis: Workflow Q-TOF MS TLC / GC Wewer et al 2011 Wewer et al., 2011 J.Lip.Res.
8 Tandem Mass Spectrometry Direct infusion of lipid extract Selection of desired ions in Q1 Fragmentation of selected ions in Q2 (MS/MS) Time of Flight separation of fragment ions
9 Problems to overcome: Standards Free sterols: Saturated sterols: commercially available Sterol Esters: cholesterol esters: commercial available Sterol glucosides: synthesized ed from free saturated ated sterols s and glucopyranosyl-bromide-tetrabenzoate Acylated sterol glucosides saturated ASG: hydrogenation of ASG from soybean
10 Fragmentation Patterns of Sterols Free Sterols (FS) (betainylated) Improve ionization Introduce good Leaving group Sterol Esters (SE) Use of cholesterol esters as internal standards Sterol glucosides (SG) Acylated sterol glucosides (ASG) Saturated ASGs and SGs fragment differently than unsaturated ones
11 ASG Molecular Species ASG Arabidopsis leaf 16:0-Glc-Sitosterol 18:3-Glc-Sitosterol 18:2-Glc-Sitosterol
12 SE Molecular Species SE Arabidopsis leaf 18:3-Sitosterol 18:2-Sitosterol
13 Method Validation GC vs. Q-TOF MS GC Q-TOF Analysis of Arabidopsis WT leaves by GC and Q-TOF MS. Proof of concept Advantages of Q-TOF MS Only small amounts of plant tissue required Easy sample preparation allows for a large number of samples Direct measurement of conjugated sterols present at low abundances (esp. ASG)
14 Method Application Arabidopsis thaliana +P -P
15 Sterol Analysis in Arabidopsis under Phosphate Deprivation WT pho1 1, WT leaf (+P) 2, pho1 leaf (-P) + P -P 3, WT leaf +P 4, WT leaf P 5, WT root, +P 6, WT root, -P No major changes in the composition of sterol species. (here: free sterols, distribution similar in SE, SG and ASG)
16 Sterol Analysis in Arabidopsis under Phosphate Deprivation WT pho1 1, WT leaf (+P) 2, pho1 leaf (-P) * 3, WT leaf +P 4, WT leaf P 5, WT root, +P 6, WT root, -P P -P
17 Sterol Analysis in Arabidopsis under Phosphate Deprivation WT pho1 1, WT leaf (+P) 2, pho1 leaf (-P) * 3, WT leaf +P 4, WT leaf P 5, WT root, +P 6, WT root, -P P -P Sterol Ester amounts increase during P conditions, but also in plants grown in sterile culture: Sterol Ester accumulate during different stress conditions.
18 Sterol Analysis in Arabidopsis under Phosphate Deprivation WT pho1 1, WT leaf (+P) 2, pho1 leaf (-P) * 3, WT leaf +P 4, WT leaf P 5, WT root, +P 6, WT root, -P P -P Glycosylated sterols (SG, ASG) are increased during P conditions in leaves
19 Sterol Analysis in Arabidopsis under Phosphate Deprivation ASG WT pho1 1, WT leaf (+P) 2, pho1 leaf (-P) 3, WT leaf +P 4, WT leaf P 5, WT root, +P 6, WT root, -P + P -P 16:0-ASG decreased, and 18:3-ASG increased during Pi deprivation.
20 Conclusion Arabidopsis thaliana SG and ASG increased at Pi Glyosylated sterols replace phospholipids. (also see: Anderson et al JBC, Tjellström et al FASEB J) 18:3-ASG increased, 16:0-ASG decreased at - Pi
21 University of Bonn Institute Molecular Physiology Biotechnology of Plants (IMBIO) Instit te of Molec lar Ph siolog and Biotechnolog Vera Wewer Isabel Dombrink Katharina vom Dorp Peter Dörmann
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