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TERPENES and FLAVONOIDS from SALVIA APIANA and THEIR AFFINITIES to CANNABINOID and OPIOID RECEPTORS By: Taylor Hayes a Thesis Su

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TERPENES and FLAVONOIDS from SALVIA APIANA and THEIR AFFINITIES to CANNABINOID and OPIOID RECEPTORS By: Taylor Hayes a Thesis Su TERPENES AND FLAVONOIDS FROM SALVIA APIANA AND THEIR AFFINITIES TO CANNABINOID AND OPIOID RECEPTORS By: Taylor Hayes A thesis submitted to the faculty of The University of Mississippi in partial fulfillment of the requirements of the Sally McDonnell Barksdale Honors College Oxford, MS May 2016 Approved by _________________________ Advisor: Dr. Samir A. Ross _________________________ Reader: Dr. Stephen J. Cutler _________________________ Reader: Dr. John M. Rimoldi © 2016 Taylor Josephine Hayes ALL RIGHTS RESERVED ii ACKNOWLEDGEMENTS I first want to thank my advisor, Dr. Samir A. Ross, and Dr. Sri Vedavyasa Sri Radhakrishnan for their guidance and encouragement. I am very thankful for Dr. Ross allowing me to work with in his lab in order to complete this process. I am extremely thankful for Dr. Radhakrishnan for the countless hours he has devoted to teaching me about the process of research and scientific writing. I would not have been able to finish this project without their support. Thank you to Dr. Stephen J. Cutler and Dr. John M. Rimoldi for serving as readers for this thesis. It would not have been possible without their input and willingness to help out. All of this Research was made possible by the Institutional Development Award (IDeA) Grant Number P20GM104932 from the National Institute of General Medical Sciences (NIGMS) and the Center of Research Excellence in Natural Products Neuroscience at the University of Mississippi. I would also like to thank the Sally McDonnell Barksdale Honors College for giving me the opportunity and the push that I needed take on a thesis. Dr. John Samonds was very helpful in answering all of my questions and concerns through this process. Lastly, I could not have done this without the support of my family and friends. I could not have made it this far without the encouragement they have shown me in all of my academic endeavors. iii ABSTRACT TAYLOR JOSEPHINE HAYES: Terpenes and flavonoids from Salvia apiana and their binding affinities to cannabinoid and opioid receptors (Under the direction of Dr. Samir Ross) Salvia apiana (white sage, Lamiacae family) plant is native to southern California and parts of Mexico. Some Native American tribes local to this region consider S. apiana to be sacred and burn the leaves as incense for purification ceremonies. The plant has been used to treat sore throats, coughs, chest colds, upper respiratory infections, and poison oak rashes. Native Americans widely used this plant in traditional Chumash healing. Infusion of the leaves is used as a diaphoretic and diuretic. The aqueous ethanolic extract of S. apiana showed moderate activity towards the CB1 receptor (58.3% displacement). The extract was fractionated on silica gel column chromatography using hexanes-acetone gradient to yield 15 fractions. Further fractionation using column chromatography led to isolation of nine compounds. The structures of the isolated compounds were determined by their 1D, 2D NMR and MS spectral data. They were identified to be four diterpenes: rosmadial, carnosol, 16-hydroxycarnosol, and sageone; two flavonoids: cirsimaritin, and salvigenin; and three triterpenes: oleanolic acid, uvaol, and ursolic acid. All the fractions and isolated compounds were submitted for biological studies for cannabinoid and opioid receptor binding. One diterpene, sageone, was found to be active towards CB1 (72.5% displacement) and CB2 (79.8% displacement) and moderately active towards the mu opioid receptor (54.7% displacement). iv TABLE OF CONTENTS LIST OF TABLES AND FIGURES………………….………………………………………….vi LIST OF ABBREVIATIONS……………….……………………………………………….…...ix BACKGROUND…………………………...……………………………………………………..1 METHODS………………………………………………………………………………………..5 ISOLATED COMPOUNDS…..………………………………………………………..………..11 BIOASSAY RESULTS………………………………………………………………………….37 CONCLUSION……………………………………………………………………………..……40 LIST OF REFERENCES.………………………………………………………………………..41 v LIST OF TABLES AND FIGURES Figure 1 Salvia apiana……………………………………………………………...………1 Figure 2 Salvia apiana smoking……………………………………………...……………..2 Figure 3 Plant material being filtered of after an ethanol extraction.………………….……5 Figure 4 Two normal phase columns ………………………………………………………6 Figure 5 A fraction being evaporated with a rotavapor …………………………………….7 Figure 6 Flow chart of isolated compounds ………………………………………………..8 Figure 7 1H NMR results for rosmadial …………………………………………………..12 Figure 8 13C NMR spectrum for rosmadial………………………………………………..13 Figure 9 HRMS for rosmadial……………………………………………………………..13 Figure 10 Chemical structure of rosmadial (I)……...………………………………………14 Figure 11 1H NMR results for carnosol……….………………………………………….....15 Figure 12 13C NMR spectrum for carnosol…………………………………………………16 Figure 13 HRMS for carnosol ……………………………………………………………...16 Figure 14 Chemical structure of carnosol (II)...…………………………………………….17 Figure 15 1H NMR results for 16-hydroxycarnosol ………………………………………..18 Figure 16 13C NMR spectrum for 16-hydroxycarnosol …………………………………….19 Figure 17 HRMS for 16-hydroxycarnosol …………………………………………………19 Figure 18 Chemical structure of 16-hydroxycarnosol (III)………………………………...20 Figure 19 1H NMR results for sageone …………………………………………………….21 vi Figure 20 13C NMR spectrum for sageone …………………………………………………22 Figure 21 HRMS for sageone ………………………………………………………………22 Figure 22 Chemical structure of sageone (IV).…………………………………………..…23 Figure 23 1H NMR results for cirsimaritin …………………………………..……………..24 Figure 24 13C NMR spectrum for cirsimaritin ……………………………………………..25 Figure 25 HRMS for cirsimaritin …………………………………………………………..25 Figure 26 Chemical structure of cirsimaritin (V)…………...………………………………26 Figure 27 1H NMR results for salvigenin …………………………………………………..27 Figure 28 13C NMR spectrum for salvigenin……………………………………………….28 Figure 29 HRMS for salvigenin ……………………………………………………………28 Figure 30 Chemical structure of salvigenin (VI).…………………………………………..29 Figure 31 1H NMR results for oleanolic acid ………………………………………...…….29 Figure 32 13C NMR spectrum for oleanolic acid ………………..…………………………30 Figure 33 HRMS for oleanolic acid ……………………...………………………………...30 Figure 34 Chemical structure of oleanolic acid (VII)...……………………………...……..31 Figure 35 1H NMR results for uvaol ………………………………………….…………....33 Figure 36 13C NMR spectrum for uvaol…………………………………..…………….…..33 Figure 37 Chemical structure of uvaol (VIII)…..………………….……………………….34 Figure 38 1H NMR results for ursolic acid ……………………………………………..…..35 Figure 39 13C NMR spectrum for ursolic acid……………………………………………...35 Figure 40 Chemical structure of ursolic acid (IX)………………………………………….36 Table 1 1H NMR and 13C NMR data for rosmadial………………………………………11 Table 2 1H NMR and 13C NMR data for carnosol ………………...……………………..14 vii Table 3 1H NMR and 13C NMR data for 16-hydroxycarnosol…………...……...……….17 Table 4 1H NMR and 13C NMR data for sageone………………………………..……….20 Table 5 1H NMR and 13C NMR data for cirsimaritin………...…………………...……...23 Table 6 1H NMR and 13C NMR data for salvigenin ………...…….……………………..26 Table 7 1H NMR and 13C NMR data for uvaol…………………………………..............31 Table 8 Table 8: Bioassay results of crude extract and 15 fractions…………...…………38 Table 9 Bioassay results of the nine isolated compounds ………………………………..39 viii LIST OF ABBREVIATIONS brd Broad CB1 Cannabinoid receptor type 1 CB2 Cannabinoid receptor type 2 CDCl3 Deuterated Chloroform 13C NMR Carbon nuclear magnetic resonance d Doublet DCM Dichloromethane DMEM Dulbecco’s modified Eagle’s medium DMSO Dimethyl sulfoxide EtOAc Ethyl acetate g Gram 1H NMR Proton nuclear magnetic resonance HRESIMS High-resolution electrospray ionisation mass spectrometry HRMS High resolution mass spectra MHz Megahertz m Multiplet mL Milliliters nM Nanomoles NMR Nuclear magnetic resonance q Quartet ix sept. Septet t Triplet TLC Thin layer chromatography TMS Tetramethylsilyl µg Microgram µM Micromole x Background I. Salvia apiana Figure 1: Salvia apiana (Weldon, 2010) Salvia apiana, a member of the Lamiaceae family, is commonly known as white sage. The shrub has long, thin, velvety leaves and colors ranging from shades of gray to green. Small flowers grow on white sage that can be purple or white with long anthers (Adams and Garcia, 2005). S. apiana can be found scattered throughout southwestern North America, with the highest concentration in Southern California (Borek et al., 2006). Natives to the southern California region have been known to use the leaves in traditional Chumash healing. Chumash healing involves prayer, relaxation, and natural plant-based remedies. In this practice, white sage is infused into water in order to relax the patient (Adams and Garcia, 2005). The leaves have been smoked and eaten to treat sore throats, upper respiratory infections, coughs, colds, and even poison oak rashes 1 (Takeoka et al., 2008). The plant is also administered for diaphoretic and diuretic effects (Luis et al., 1996). The leaves are thought to be sacred by some native tribes and burned during purification ceremonies, or simply for the aroma (Dentali and Hoffman, 1990). Figure 2: Salvia apiana smoking (Moving Towards Peace, 2010) II. Receptors Cannabinoid and Opioid receptors are classified as G-protein coupled receptors, which are signaling receptors that recognize and transduce messages across cell membranes (Boackaert and Pin, 1999). The main subtypes of cannabinoid receptors are the CB1 and CB2 receptors, and the most prominent opioid receptors are mu (µ), kappa (κ), and delta (δ). In humans, the CB1 receptor is found throughout the central nervous system in the brain and spinal cord, while the CB2 receptor is more abundant in the peripheral nervous
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