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Analysis of Medicinal Plant Phenoloids by Coupled Tandem Mass Spectrometry

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Analysis of Medicinal Plant Phenoloids by Coupled Tandem Mass Spectrometry Analysis of medicinal plant phenoloids by coupled tandem mass spectrometry Ph.D. Thesis Balázs Blazics Semmelweis University, Department of Pharmacognosy Semmelweis University Doctoral School of Pharmaceutical Sciences Supervisor: Dr. Ágnes Kéry, Ph.D. Referees: Dr. Mária Báthori, Ph.D., D.Sc. Dr. László Drahos, Ph.D. Chair of exam comittee: Dr. Imre Klebovich, Ph.D., D.Sc. Exam comittee: Dr. Éva Lemberkovics, Ph.D. Dr. Károly Vékey, Ph.D., D.Sc. Budapest 2010 Contents Contents CONTENTS ...................................................................................................................................2 LIST OF ABBREVIATIONS ......................................................................................................4 1. INTRODUCTION ....................................................................................................................6 1.1. PRELIMINARIES ................................................................................................................................6 2. AIMS OF STUDIES ................................................................................................................8 3. BIBLIOGRAPHY REVIEW ..................................................................................................10 3.1. MASS SPECTROMETRY IN PHENOLOID ANALYTICS ..................................................................................10 3.1.1. Phenoloids .........................................................................................................................10 3.1.2. Extraction and sample preparation...................................................................................14 3.1.3. Conditions and instrumentation........................................................................................15 3.1.4. Mass spectrometry of phenolic acids, salicylates and derivatives ....................................17 3.1.5. Mass spectrometry of flavonoid aglycons.........................................................................20 3.1.6. Mass spectrometry of flavonoid glycosides.......................................................................25 3.2. OTHER METHODS COMMONLY USED FOR THE INVESTIGATION OF PHENOLOIDS (HPLC, NMR, IN VITRO ASSAYS ) .........................................................................................................................................................28 3.3. MODEL PLANTS ..............................................................................................................................30 3.3.1. Euphrasia rostkoviana HAYNE (Scrophulariaceae)............................................................31 3.3.2. Satureja hortensis L. (Lamiaceae).....................................................................................32 3.3.3. Filipendula ulmaria L. MAXIM (Rosaceae)........................................................................33 3.3.4. Sempervivum tectorum L. (Crassulaceae) ........................................................................34 3.3.5. Epilobium parviflorum Schreb. (Onagraceae) ..................................................................35 4. MATERIALS AND METHODS ..........................................................................................37 4.1. GENERAL ......................................................................................................................................37 4.1.1. Solvents and chemicals......................................................................................................37 4.1.2. Solid-phase extraction.......................................................................................................37 4.1.3. Liquid chromatography-mass spectrometry apparatus ....................................................38 4.2. EUPHRASIA ROSTKOVIANA HAYNE ......................................................................................................38 4.2.1. Plant material....................................................................................................................38 4.2.2. Extraction, fractionation and isolation..............................................................................38 4.2.3. Content of main groups of compounds .............................................................................39 4.2.4. Antioxidant activity assay .................................................................................................39 4.2.5. High performance liquid chromatographic conditions......................................................40 4.2.6. Triple quadrupole mass spectrometric conditions.............................................................41 4.2.7. Time-of-flight mass spectrometric conditions...................................................................41 4.2.8. NMR spectroscopy, apparatus and conditions..................................................................42 4.2.9. Method validation.............................................................................................................42 4.3. SATUREJA HORTENSIS L. ..................................................................................................................44 4.3.1. Plant material....................................................................................................................44 4.3.2. Extraction and sample preparation...................................................................................44 4.3.3. High performance liquid chromatographic conditions......................................................44 4.3.4. Triple quadrupole mass spectrometric conditions.............................................................45 4.3.5. Testing of method performance........................................................................................45 4.4. FILIPENDULA ULMARIA L. MAXIM ....................................................................................................45 4.4.1. Plant material....................................................................................................................45 4.4.2. Extraction and sample preparation...................................................................................46 4.4.3. High performance liquid chromatographic conditions......................................................46 2 Contents 4.4.4. Triple quadrupole mass spectrometric conditions.............................................................46 4.4.5. Method validation.............................................................................................................47 4.5. SEMPERVIVUM TECTORUM L. ...........................................................................................................48 4.5.1. Plant material....................................................................................................................48 4.5.2. Extraction and sample preparation...................................................................................48 4.5.3. High performance liquid chromatographic conditions......................................................49 4.5.4. Triple quadrupole mass spectrometric conditions.............................................................49 4.6. EPILOBIUM PARVIFLORUM SCHREB . ...................................................................................................49 4.6.1. Plant material....................................................................................................................49 4.6.2. Extraction and sample preparation...................................................................................50 4.6.3. High performance liquid chromatographic conditions......................................................50 4.6.4. Triple quadrupole mass spectrometric conditions.............................................................50 5. RESULTS AND DISCUSSION ...........................................................................................52 5.1. EUPHRASIA ROSTKOVIANA HAYNE ......................................................................................................52 5.1.1. Polyamide fractionation and isolation ..............................................................................52 5.1.2. Antioxidant effect..............................................................................................................53 5.1.3. Qualitative analysis ...........................................................................................................55 5.1.4. Quantitation of acteoside..................................................................................................64 5.1.5. NMR spectroscopy.............................................................................................................65 5.1.6. Quantitative result and method validation .......................................................................66 5.1.7. Summary ...........................................................................................................................68 5.2. SATUREJA HORTENSIS L. ..................................................................................................................68 5.3. FILIPENDULA ULMARIA L. MAXIM ....................................................................................................72 5.3.1. Qualitative analysis ...........................................................................................................72 5.3.2. Quantitative analysis.........................................................................................................77
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