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Development of Anti-Inflammatory Agents from the Aromatic

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Development of Anti-Inflammatory Agents from the Aromatic DEVELOPMENT OF ANTI-INFLAMMATORY AGENTS FROM THE AROMATIC PLANTS, ORIGANUM SPP. AND MENTHA SPP., AND ANALYTICAL METHODS ON THE QUALITY CONTROL OF BIOACTIVE PHENOLIC COMPOUNDS by DIANDIAN SHEN A dissertation submitted to the Graduate School-New Brunswick Rutgers, The State University of New Jersey for the degree of Doctor of Philosophy Graduate Program in Medicinal Chemistry Written under the direction of Dr. James E. Simon and approved by ________________________ ________________________ ________________________ ________________________ ________________________ New Brunswick, New Jersey October , 2008 ABSTRACT OF THE DISSERTATION DEVELOPMENT OF ANTI-INFLAMMATORY AGENTS FROM THE AROMATIC PLANTS, ORIGANUM SPP. AND MENTHA SPP., AND ANALYTICAL METHODS ON THE QUALITY CONTROL OF BIOACTIVE PHENOLIC COMPOUNDS by DIANDIAN SHEN Dissertation Director: Dr. James E. Simon The development of new anti-inflammatory drugs comes at high cost and risk, as evidenced by the fact that several novel prescription non-steroidal anti-inflammatory drugs (NSAIDs) have been withdrawn from the market due to potential health risks. Meanwhile, natural dietary supplements with anti-inflammatory activities are gaining increased interest by consumers and industry as they are perceived to be of lower cost, with fewer adverse effects and yet function as complementary and alternative medicines. We successfully identified the anti-inflammatory constituents from post-distillation material of oregano, an aromatic plant long prized as a food seasoning and spice in western and Middle Eastern cuisine and a rich source of essential oil. The anti-inflammatory compounds in oregano were identified as rosmarinic acid, oleanolic acid and ursolic acid by using bioactivity-guided isolation, LC/MS and NMR techniques. We subsequently elucidated their possible inhibitory mechanisms during the inflammatory cell signaling pathways by screening different bioassays, and a synergistic action for the combination of these three compounds was observed on the LPS-induced ii nitrite production assay. An LC/MS (SIM mode) method employing a tandem column system was developed for the simultaneous quantitation of these three compounds in oregano. Validation for this method showed a precision (relative standard deviation) ranging from 4.84% to 6.41%, and the recoveries varied from 92.2% to 100.8% for the three analytes. In order to investigate genetic diversity between species and within a species relative to the anti-inflammatory compounds, different oregano species, varieties and breeding lines were collected from around the world, vegetatively field transplanted into a Rutgers Agricultural Research Experiment Station farm, where the plants were field grown, harvested and quantitated for their anti-inflammatory contents based upon the LC/MS method developed in this study. We next examed mint, another aromatic plant in the Lamiaceae family, and proved that these three anti-inflammatory compounds also accumulated in this plant. An analytical survey was further performed to determine anti-inflammatory agent-rich sources from eight commercial mint species as well as many specialty varieties within the different species. To facilitate the frequent quality control requirement and material pre-evaluation, we developed and validated a near-infrared spectroscopy (NIR) method for the fast quantitation of anti-inflammatory constituents in oregano and mint. Finally, we investigated the anti-inflammatory compound distribution and related chemical properties of the oregano post-distillation materials. iii ACKNOWLEDGEMENTS I thank Dr. James E. Simon for his encouragement, direction and assistance throughout this research project. I would like to extend my appreciation to Dr. Chi-Tang Ho, Dr. Edmond LaVoie, Dr. Thomas Hartman, Dr. Qingli Wu and Dr. Mingfu Wang for their valuable advice and support. I acknowledge Dr. Chung-Heon Park for his help in providing oregano and mint samples from the Rutgers plant breeding and germplasm programs. I would also like to thank the other members of Dr. Simon’s lab group for their help as well as personal insight of making this experience more comfortable and encouraging. I acknowledge Dr. Arthur Tucker for providing the species authentication and taxonomy for all the mints; Dayton Jones and Dan Shiley for NIR spectra collection and multivariate analysis; and Dr. Lenore Rasmussen for her assistance and instruction on the 2D NMR experiment. I would like to offer my special thanks to my wife, Xihao Li, for her love and support. iv DEDICATION I dedicate this work to my wife Xihao Li and my daughter Lindsay Shen. v TABLE OF CONTENTS ABSTRACT OF THE DISSERTATION ............................................................................ ii ACKNOWLEDGEMENTS............................................................................................... iv DEDICATION .................................................................................................................... v TABLE OF CONTENTS................................................................................................... vi LIST OF TABLES ............................................................................................................. xi LIST OF FIGURS............................................................................................................xiii LIST OF ABBREVIATIONS ......................................................................................... xvii CHAPTER 1. INTRODUCTION ....................................................................................... 1 1.1. ANTI-INFLAMMATION: BACKGROUND ON THE DEFINITION, CAUSES AND CURRENT TREATMENTS INCLUDING THE TYPES AND UNDERLYING MECHANISMS OF ACTION OF CURRENT ANTI-INFLAMMATORY DRUGS ........................................................................... 2 1.2. SAFETY ISSUES AS TO ANTI-INFLAMMATORY DRUGS .......................... 8 1.3. OPPORTUNITIES FOR THEN NEXT GENERATION OF NEWER ANTI-INFLAMMATORY AGENTS AND DIETARY SUPPLEMENTS................. 9 1.4. BACKGROUND AS TO ANTI-INFLAMMATORY PROPERTIES OF OREGANO AND HYPOTHESIS ............................................................................ 12 1.5. RESEARCH OUTLINE .................................................................................... 15 1.6. REFERENCES .................................................................................................. 19 CHAPTER 2. IDENTIFICATION OF THE ANTI-INFLAMMATORY CONSTITUENTS IN OREGANO AND THEIR BIOACTIVE PROPERTIES............................................. 24 2.1. INTRODUCTION ............................................................................................. 25 2.2. MATERIALS AND METHODS ....................................................................... 26 2.2.1. Folin-Ciocalteu’s Method on Total Phenolic Content Determination. ... 26 2.2.2. DPPH Radical Scavenging Assay. .......................................................... 27 2.2.3. Isolation and Identification of Rosmarinic, Oleanolic and Ursolic Acids. ........................................................................................................................... 28 2.2.4. Anti-inflammatory Assays for Plant Extract, Pure Compound and Synergistic Action Study................................................................................... 29 2.2.5. Cell Culture............................................................................................. 29 2.2.6. Nitrite Assay............................................................................................ 30 2.2.7. Western Blotting. .................................................................................... 31 2.2.8. Secretory Phospholipase A 2 Screening Assay......................................... 32 2.2.9. 5-Lipoxygenase Screening Assay. .......................................................... 34 2.3. RESULTS AND DISCUSSION......................................................................... 35 2.3.1. Preliminary Tests on Oregano Extract. ................................................... 35 2.3.2. LC/UV/MS Guided Preparative HPLC Separation. ............................... 37 2.3.3. Identification of Rosmarinic Acid, Oleanolic Acid and Ursolic Acid. ... 38 2.3.4. Anti-inflammatory Activities of Rosmarinic Acid, Oleanolic Acid and vi Ursolic Acid on Nitrite Assay and Synergistic Study. ...................................... 42 2.3.5. Western Blotting on iNOS and COX-2 Protein Levels........................... 45 2.3.6. Secretory Phospholipase A 2 Inhibitor Screening. ................................... 47 2.3.7. 5-Lipoxygenase Inhibitor Screening....................................................... 49 2.3.8. The in vivo Anti-inflammatory Activities of Rosmarinic Acid Reported in Literature........................................................................................................... 52 2.4. PHARMACOKINETIC FEATURES OF ROSMARINIC ACID, OLEANOLIC ACID AND URSOLIC ACID................................................................................... 54 2.5. COMPOUND SAFETY EVALUATION........................................................... 57 2.6. CONCLUSIONS................................................................................................ 59 2.7. REFERENCES .................................................................................................. 60 CHAPTER 3. DEVELOPMENT OF ANALYTICAL METHOD (LC/MS-SIM MODE) ON SIMULTANEOUS DETERMINATION OF ANTI-INFLAMMATORY CONSTITUENTS IN ORIGANUM
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