Gas Chromatography/ Mass Spectrometry

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1 Gas Chromatography/ Mass Spectrometry Edited by H.F. Linskens and J.F. Jackson Contributors R.S. Bandurski G. Combaut A.Ehmann P.Hedden B.Janistyn H.Kameoka H.Kodama D.V.Lynch J.K.MacLeod H.Nyberg L.M.S.Palni L.Rivier R.R. Selvendran B.J.H. Stevens S.A.B.Tay G.A. Thompson Jr.,L.Witte With 98 Figures Springer-Verlag Berlin Heidelberg New York Tokyo

2 Contents The Use of Combined Gas Chromatography-Mass Spectrometry in the Analysis of Plant Growth Substances P. HEDDEN (With 8 Figures) 1 Introduction 1 2 Identification by GC-MS Derivatisation Methylation Trimethylsilylation Permethylation Gas Chromatography Qualitative Mass Spectrometry Quantitative Mass Spectrometry 5 3 Gibberellins Extraction and Purification GC-MS 11 4 Abscisic Acid and Related Compounds Qualitative GC-MS Quantitative GC-MS 17 5 Brassinosteroids 18 References 19 Applications of Mass Spectrometry for the Examination of Pectic Polysaccharides R. R. SELVENDRAN and B. J. H. STEVENS (With 6 Figures) 1 Introduction 23 2 Structural Analysis of Pectic Polysaccharides 23 3 Determination of the Nature of the Glycosidic Linkages 24 4 Separation and Identification of Partially Methylated Alditol Acetates Extensions of Methylation Analysis Controlled Partial Acid Hydrolysis Studies /?-Eliminative Degradation Studies Neutral Glycosyl Residues Linked to Galacturonosyl Residues Glycosyl Residues Linked to 0-4 of 2,4-Linked Rhamnopyranosyl Residues 32 6 Sequencing of Sugar Residues in Pectins Partial Acid Hydrolysis Characterisation of Oligosaccharides as Permethylated Derivatives 34

3 Contents IX 6.2 Partial Acetolysis Enzymatic Hydrolysis 38 7 Sequencing of Pectic Polysaccharides by Partial Depolymerisation of Permethylated Derivatives 38 8 Experimental 40 References 43 GC-MS Methods for Cyclic Nucleotides in Higher Plants and for Free High Unsaturated Fatty Acids in Oils B. JANISTYN (With 10 Figures) 1 Introduction 47 2 Methods of GC-MS 48 3 Adenosine-3': 5'-Monophosphate (camp) in Maize Seedlings (Zea mays) 48 4 An Isotope Dilution GC-MS Spectrometric Assay for camp in Cultured Tobacco Tissue 51 5 Stability of Cyclic Purine Nucleotides in the Presence of Hydrochloric Acid During Extraction 55 6 Guanosine-3': 5'-Monophosphate (cgmp) in Maize Seedlings (Zea mays) 56 7 GC-Separation of Synthetic camp and cgmp in a Mixture 59 8 Cyclic Pyrimidine Nucleotides in Plants? 60 9 Free High Unsaturated Fatty Acids in Oils Conclusions 64 References 65 GC-MS Methods for Lower Plant Glycolipid Fatty Acids H. NYBERG (With 4 Figures) 1 Introduction Extraction of the Plant Material Handling and Storage Extraction with Organic Solvents Purification of the Extract 69 3 Separation of Glycolipids from the Total Lipid Extract Column Chromatography Thin-Layer Chromatography (TLC) Other Applications 73 4 Isolation of the Glycolipids Thin-Layer Chromatography Localization of the Glycolipids on TLC Removing the Spots from the TLC Plates 76 5 Derivatization of the Glycolipid Fatty Acids for GC-MS General Features Formation of Methyl Esters Silylation and Other Methods 77

4 X Contents 6 GLC Instrumentation for Fatty Acid Analysis General Features Carrier Gas System Injection and Injectors The Detector -, Column Selection for Fatty Acid GLC Analysis Column Types Supports, Liquid Phases, and Their Characteristics 84 8 Interpretation of GC Data and Calculation of Results Identification of Peaks Using Standard Compounds Quantitation of Results External and Internal Standardization 89 9 Fatty Acid Ester Structure Determination by GC-MS Equivalent Chain Lengths (ECL) Semilogarithmic Correlations Mass Spectrometers and Their Function Principles Interpretation of Mass Spectra of Fatty Acid Esters Abbreviations 94 References 95 Analysis of Phospholipid Molecular Species by Gas Chromatography and Coupled Gas Chromatography-Mass Spectrometry D. V. LYNCH and G. A. THOMPSON, Jr. (With 6 Figures) 1 Introduction Lipid Preparation Lipid Extraction Purification of Phospholipids Column Chromatography Thin Layer Chromatography Formation of Derivatives for GC or GC-MS Phospholipase C Treatment Conversion of Diacylglycerols to Silyl Derivatives Formation of Trimethylsilyl Derivatives Formation of tert-butyldimethylsilyl Derivatives Gas Chromatography Mass Spectrometry Instrumentation Ill 5.2 Operating Conditions..Ill 5.3 Identification of Molecular Species Ill 5.4 Quantitation of Molecular Species by GC-MS Quantitation of Molecular Species by GC-MS Following Reduction of Double Bonds Using Deuterium Direct MS Analysis of Underivatized Phospholipids Determination of Positional Distribution of Acyl Chains Using Phospholipase A Conclusion 118 References 119

5 Contents XI GC-MS of Plant Sterol Analysis G. COMBAUT (With 2 Figures) 1 Introduction Development of GC-MS Plant Sterol Analysis Operations Before GC-MS Sterol Analysis Extraction and Isolation of Plant Sterols Free Sterols and (or) Sterols from Steryl-Esters Purification of Sterolic Fractions Derivatization Characterization of Sterols Characterization of Sterols by GC Data Characterization of Sterols by MS Data Characterization of Sterols by GC and MS Data A Typical Analysis of 4-Demethyl and 4,4-Dimethyl Sterols from Zea mays Co-Occurrence of A 5 - and z! 7 -Sterols in Tracheophytes Side Chain-Hydroxylated Sterols from Red Algae... : Methyl Sterols of Dinoflagellates Conclusion 130 References 131 GC-MS Methods for Terpenoids L. WlTTE 1 Introduction Isolation Methods Prefractionation and Ancillary Reactions Gas Chromatography Retention Data Mass Spectrometry 140 References 142 GC-MS of Auxins L. RIVIER (With 22 Figures) 1 Introduction The Compounds Involved Reference Compounds Extraction Purification Columns for GC Injection Techniques Derivatisation Interface Between GC and MS Mass Spectrometer Data Systems Ionization 163

6 XII Contents 13 GC-MS Strategy for Auxin Analysis Quantification The Internal Standard Experimental Procedure Conclusions : 185 References 185 GC-MS Methods for the Quantitative Determination and Structural Characterization of Esters of Indole-3-Acetic Acid and myo-inositol R. S. BANDURSKI and A. EHMANN (With 4 Figures) 1 Introduction Discovery of IAA-Inositols Occurrence of IAA Conjugates Importance of Measuring and Identifying Hormone Conjugates Quantitative Analysis and Identification of the IAA-Inositols Analysis After Hydrolysis Methods for Hydrolysis of IAA Conjugates Use of Internal Standards Analysis Before Hydrolysis A Quantitative Estimation of IAA-Inositol Using [ 3 H]-IAAmyo-Inositol as an Internal Standard Qualitative Analysis of IAA-Inositols The Inositol Moiety Derivitization of IAA-Inositols for GC-MS Mass Spectral Fragmentation Pattern l-dl-l-o-(indole-3-acetyl)-myo-inositol (6 TMS, MW 769) O-(Indole-3-Acetyl)-myo-Inositol(6TMSMW769) Di-O-[N-(Trimethylsilyl) Indole-3-Acetyl]-O-Tetra-O- Trimethylsilyl-myo-Inositol Tri-O-[N-(Trimethylsilyl) Indole-3-Acetyl]-O-Tri-O- Trimethylsilyl-myo-Inositol IAA-myo-Inositol-Arabinoside and IAA-myo-Inositol- Galactoside Uses of GC-MS to Identify and Characterize IAA-Esters Conclusions Abbreviations 211 References. 211 GC-MS Methods for Cytokinins and Metabolites L. M. S. PALNI, S. A. B. TAY, and J. K. MACLEOD (With 8 Figures) 1 Introduction Gas Chromatography (GC) Instrumentation Liquid Stationary Phases and Columns Injectors Detectors 224

7 Contents XIII 2.2 Derivatisation of Cytokinins Trimethylsilyl (TMSi) Derivatives Permethyl Derivatives tert.-butyldimethylsilyl (t-budmsi) Derivatives Trifluoroacetyl (TFA) Derivatives Preparative GC Mass Spectrometry Instrumentation Sample Introduction Ionisation Methods Analysers Data Systems Combined Gas Chromatography-Mass Spectrometry (GC-MS) Applications of Mass Spectrometry in Cytokinin Analysis Structural Studies Quantification of Cytokinins Internal Standards Stable Isotope Dilution Mass Spectrometry Quantification Using GC-MS Probe Analysis Metabolic Profiling General Remarks and Conclusion 245 References 245 GC-MS Method for Volatile Flavor Components of Foods H. KAMEOKA (With 8 Figures) 1 Introduction GC-MS Methods Preparation Methods of Flavor Samples Operational Methods Volatile Flavor Components Fruits Vegetables Mushrooms Tea Beans and Nuts Grains Jams Fermentation Products 273 References 274 GC-MS Methods for Tobacco Constituents H. KODAMA (With 20 Figures) 1 Introduction Cembranoids and Their Degraded Compounds 277

8 XIV Contents 3 Labdanoids and Their Degraded Compounds Carotenoid-Degraded Compounds Sesquiterpenoids Terpenoid Glycosides Linked Scanning 294 References 298 Subject Index 299

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