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Variability and Biologically Active Components of Some Lamiaceae

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Variability and Biologically Active Components of Some Lamiaceae Department of Pharmacognosy University of Szeged Variability and biologically active components of some Lamiaceae species Ph.D. Thesis Katalin Veres Supervisor: Dr. Erzsébet Varga Szeged, Hungary 2007 LIST OF PUDLICATION RELATED TO THE THESIS I. Veres K, Varga E, Dobos Á, Hajdú Zs, Máthé I, Pluhár Zs, Bernáth J: Investigation on Essential Oils of Hyssopus officinalis L. populations In: Franz Ch, Máthé Á, Buchbaner G, eds. Essential Oils: Basic and Applied Research Allured Publishing Comparation, 1997, pp 217-220. II. Varga E, Hajdú Zs, Veres K, Máthé I, Németh É, Pluhár Zs, Bernáth J: Hyssopus officinalis L. produkcióbiológiai és kémiai változékonyságának tanulmányozása Acta Pharm. Hung. 1998; 68 : 183-188 III. Veres K, Varga E, Dobos Á, Hajdú Zs, Máthé I, Németh É, Szabó K: Investigation of the Content and Stability of Essential Oils of Origanum vulgare ssp. vulgare L. and O. vulgare ssp. hirtum (Link) Ietswaart Chromatographia 2003; 57 : 95-98 IV. Janicsák G, Veres K , Kállai M, Máthé I: Gas chromatographic method for routine determination of oleanolic and ursolic acids in medicinal plants Chromatographia 2003; 58 : 295-299 V. Janicsák G, Veres K, Kakasy AZ, Máthé I: Study of the oleanolic and ursolic acid contents of some species of the Lamiaceae Biochem. Syst. Ecol. 2006; 34 : 392-396 VI. Veres K , Varga E, Schelz Zs, Molnár J, Bernáth J, Máthé I: Chemical Composition and Antimicrobial Activities of Essential Oils of Four Lines of Origanum vulgare subsp. hirtum (Link) Ietswaart Grown in Hungary Natural Product Communications 2007; 2: 1155-1158 CONTENTS 1. INTRODUCTION............................................................................................................................. 1 2. AIMS OF THE STUDY.................................................................................................................... 2 3. LITERATURE OVERVIEW........................................................................................................... 2 3.1. LAMIACEAE FAMILY ..................................................................................................................... 2 3.1.1. Taxonomy of the family Lamiaceae..................................................................................... 2 3.1.2. Chemical constituents of the family Lamiaceae................................................................... 3 3.1.3. Activity of compounds ......................................................................................................... 4 3.2. HYSSOPUS .................................................................................................................................... 4 3.2.1. Botany of Hyssopus officinalis L. ........................................................................................ 4 3.2.2. Chemistry of Hyssopus officinalis L. ................................................................................... 5 3.2.3. Biological activity and medicinal use of Hyssopus officinalis L. ........................................ 6 3.3. ORIGANUM ................................................................................................................................... 6 3.3.1. Botany of the investigated Origanum species ...................................................................... 6 3.3.2. Chemistry of the investigated Origanum species ................................................................. 8 3.3.3. Biological activity and use of the investigated Origanum species ..................................... 12 4. MATERIALS AND METHODS.................................................................................................... 14 4.1. PLANT MATERIAL ....................................................................................................................... 14 4.2. MORPHOLOGICAL INVESTIGATION ............................................................................................. 14 4.3. CHEMICAL ANALYSIS ................................................................................................................. 14 4.3.1. Essential oils....................................................................................................................... 15 4.3.2. Rosmarinic acid .................................................................................................................. 16 4.3.3. Oleanolic and ursolic acids................................................................................................. 16 4.4. MEASUREMENTS OF BIOLOGICAL ACTIVITY ............................................................................. 17 4.4.1. Bacteriostatic and fungistatic activities .............................................................................. 17 4.4.2. Antioxidant activity ............................................................................................................ 17 5. RESULTS AND DISCUSSION...................................................................................................... 18 5.1. PRELIMINARY STUDIES ............................................................................................................... 18 5.2. HYSSOP ....................................................................................................................................... 19 5.2.1. Morphological studies ........................................................................................................ 19 5.2.2. Studies of the essential oils................................................................................................. 21 5.2.2.1. Quantitative studies..................................................................................................... 21 5.2.2.2. Essential oil composition ............................................................................................ 24 5.2.3. Quantitative determination of rosmarinic acid ................................................................... 28 5.3. ORIGANUM ................................................................................................................................. 31 5.3.1. Studies of the essential oils................................................................................................. 31 5.3.1.1. Quantitative studies..................................................................................................... 31 5.3.1.2. Essential oil composition ............................................................................................ 32 5.3.1.3. Stability studies of the essential oils............................................................................ 33 5.3.2. Quantitative studies of rosmarinic acid .............................................................................. 35 5.3.3. Stock evaluation for selection of chemotypes .................................................................... 35 5.4. ELABORATING A METHOD FOR THE PARALLEL MEASUREMENT OF OLEANOLIC ACID /URSOLIC ACID CONTENTS .......................................................................................................................... 40 5.5. STUDIES OF PHYSIOLOGICAL EFFECTS ........................................................................................ 42 5.5.1. Correlations between essential oil composition and antimicrobial activity........................ 42 5.5.2. Correlations between rosmarinic acid content and antioxidant activity............................. 44 6. SUMMARY...................................................................................................................................... 46 7. REFERENCES................................................................................................................................ 48 ACKNOWLEDGEMENTS APPENDIX Abbreviations GC – gas chromatography GC/MS – gas chromatography/mass spectrometry TLC – thin-layer chromatography SPE – solid-phase extraction LPO – lipid peroxidation MIC – minimal inhibitory concentration SSD – statistically significant difference RA – rosmarinic acid OA – oleanolic acid UA – ursolic acid CA – cholesteryl acetate EtOH – ethanol MeOH – methanol 1. INTRODUCTION Numerous species of the family Lamiaceae which are rich in volatile oils are of great importance as herbs and spices. As regards their morphology and chemical compositions, a substantial proportion of these plants are polymorphic. Such diversity raises important theoretical and practical issues. It can be challenging to classify the species, basic research for the purposes of variety breeding is incomplete, and quality assurance is also often problematic. Consistent with these features, the variability in essential oil composition may alter the gastronomic value of the spices and modify the physiological effects of the herbs in the event of medicinal use. Therefore, it is easy to understand why complex explorative pharmacological studies of the active constituents are playing an increasingly important role over and above chemical and analytical evaluations. Practical evaluations of numerous Lamiaceae species have brought various classes of constituents other than essential oils into focus. These include hydroxycinnamic acid derivatives (mainly rosmarinic acid) as representatives of natural antioxidants, and also triterpene carboxylic acids, characterized by physiological activity. In this context, complex research into the family Lamiaceae was begun some decades ago as a cooperative program in which several Hungarian research centers are engaged in the evaluation of medicinal plants.
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