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Analysis and Comparison of Essential Oil Components Extracted from the Heartwoods of Leyland Cypress, Alaska Yellow Cedar, and Monterey Cypress

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Analysis and Comparison of Essential Oil Components Extracted from the Heartwoods of Leyland Cypress, Alaska Yellow Cedar, and Monterey Cypress AN ABSTRACT OF THE THESIS OF Xinfeng Liu for the degree of Master of Science in Wood Science presented on March 17, 2009. Title: Analysis and Comparison of Essential Oil Components Extracted from the Heartwoods of Leyland Cypress, Alaska Yellow Cedar, and Monterey Cypress. Abstract approved: ___________________________ Joseph J. Karchesy The essential oil components of cedar heartwoods play an important role in the durability of these trees. Yet, the composition of these oils and identity of many of the compounds remains unknown, or incompletely know for some commercially important cedar heartwoods. The essential oil extracts of Alaska Yellow Cedar (Chamaecyparis nootkatensis), Monterey Cypress (Cupressus macrocarpa), and Leyland Cypress (xCupressoparis leylandii ) which is an intergenetic hybrid of the first two species is such a case. GC-MS analyses were carried out on the heartwood essential oil extracts of these three species in order to determine the chemical composition of each essential oil and to compare the composition of the intergenetic hybrid (Leyland Cypress) with its parent species. Analyses were carried out on both steam distilled (6 and 12 hour) and solvent extracted oils. For example in the 6 hour distilled oils, Carvacrol was the major component of all three oils, 27% (Alaska Cedar), 67% (Leyland Cypress) and 82% (Monterey Cypress). Terpinen-4-ol and nootkatin were also found in all three oils, but in lesser amounts (3-6%). Only the oils from Alaska cedar and Leyland cypress contained the eremophilane sesquiterpenoids valencene, nootkatene, epinootkatol, nootkatol, 13-hydroxy valencene and nootkatone. This family of compounds was completely absent in Monterey cypress oil. Carvacrol, nootkatin and the eremophlianes make up 68-90% of the oils of all three species. Similar results were obtained with the 12 hour steam distilled and solvent extracts. As an intergenetic species, the components in the essential oil from Leyland Cypress show an intermediate amount of the above compounds when compared to its parents. However, the amount of hinokitiol (a monoterpene tropolone) in Leyland cypress surpassed both of its parents. It is expected that Leyland Cypress should have similar antifungal and insect resistant properties as Alaska cedar according to the essential oil components, which needs to be confirmed by future studies. Leyland cypress also shows promise for a source of important biobased chemicals such as nootkatone and its related compounds given the fast growth of this tree. ©Copyright by Xinfeng Liu March 17, 2009 All Rights Reserved Analysis and Comparison of Essential Oil Components Extracted from the Heartwoods of Leyland Cypress, Alaska Yellow Cedar, and Monterey Cypress. by Xinfeng Liu A THESIS Submitted to Oregon State University in partial fulfillment of the requirements for the degree of Master of Science Presented March 17, 2009 Commencement June 2009 Master of Science thesis of Xinfeng Liu presented on March 17, 2009. APPROVED: ________________________________________ Major Professor, representing Wood Science and Engineering ________________________________________ Head of the Wood Science and Engineering ________________________________________ Dean of the Graduate School I understand that my thesis will become part of the permanent collection of Oregon State University libraries. My signature below authorizes release of my thesis to any reader upon request. __________________________________ __ Xinfeng Liu, Author ACKNOWLEDGEMENTS First of all, all my thanks cannot express my appreciation of Dr. Joe Karchesy enough who is my major professor. It is your supports that bring me here in Oregon State University. It is your encouragement that makes me heading to the higher level of my education. And it is your love that makes me feel home here in U.S. all myself alone. Last but not least, it is your guide that makes me who I am today not only for study but also for life. Also, my thanks should go to Dr. Hong Liu who is my minor Professor and Dr. Kaichang Li for being my committee member. I learned a lot from you in the classes and thanks for your time and patience for helping me reviewing my thesis. I would like to thank Dr. Rick Kelsey from USDA Forest Service for helping me with the GC-MS, and Dr. Sheeba Veluthoor for helping me solving all the problems during the experiments. Last but not least, I should thank my parents for all those unlimited supports and love. I love you so much. TABLE OF CONTENTS PAGE Introduction......................................................................................................15 Alaska-Cedar....................................................................................................1 Monterey cypress............................................................................................4 Leyland cypress ...............................................................................................7 Literature Review..............................................................................................13 Alaska cedar ..................................................................................................13 Monterey Cypress..........................................................................................18 Leyland Cypress.............................................................................................20 In Summary ...................................................................................................20 EXPERIMENTALS................................................................................................23 General Experimental Procedure ...................................................................23 Extraction of the Essential Oil ........................................................................24 Steam distillation:..........................................................................................25 Solvent Extraction..........................................................................................27 Spectroscopic analysis ...................................................................................27 Retention Indices...........................................................................................28 RESULTS AND DISCUSSION ................................................................................29 GC – MS.........................................................................................................29 Discussion......................................................................................................34 Steam distillation ....................................................................................... 34 TABLE OF CONTENTS (Continued) PAGE Board vs Wood........................................................................................... 37 Solvent extraction ...................................................................................... 38 Conclusions.......................................................................................................40 Bibliography......................................................................................................42 Appendix...........................................................................................................47 LIST OF FIGURES Figure Page 1 THE NATIVE RANGE OF ALASKA-CEDAR. ...........................................................3 2 THE NATIVE RANGE OF MONTEREY CYPRESS IN MACROSCOPE ........................5 3 THE NATIVE RANGE OF MONTEREY CYPRESS IN DETAILED MAP........................6 4 PARTIAL SEQUENCES OF RBCL IN LEYLAND CYPRESS , MONTEREY CYPRESS , AND ALASKA CYPRESS ..................................................................................9 5 SOME OF THE STRUCTURES OF THE COMPOUNDS FOUND INSIDE THE ESSENTIAL OIL FROM ALASKA CEDAR MONTEREY CYPRESS AND ALASKA CEDAR........................................................................................................17 6 STRUCTURE OF TROPOLONE, P-MENTHANE, P-CYMENE AND EREMOPHILANE ...................................................................................................................22 7 APPARATUS FOR STEAM DISTILLATION ...........................................................26 8 THE SCHEMATIC STRUCTURE OF P-METHANE, P-CYMENE AND EREMOPHILANE FAMILY AND EXAMPLES IN THE ESSENTIAL OIL FROM ALASKA CEDAR, MONTEREY CYPRESS AND LEYLAND CYPRESS. ............................................36 9 THE CONVERSION OF NOOTKATOL AND EPI-NOOTKATOL TO NOOTKATENE AND NOOTKATONE.............................................................................................38 LIST OF TABLES Table Page 1 PERCENTAGE COMPOSITION OF MONOTERPENE HYDROCARBON MIXTURES OF OILS ISOLATED FROM SOME SAMPLES OF LEYLAND CYPRESS FOLIAGE.........19 2 THE COMPONENTS OF THE 1ST 6HR DISTILLATION FRACTION FROM ALASKA CEDAR, LEYLAND CYPRESS AND MONTEREY CYPRESS ANALYZED BY GC-MS ......29 3 THE COMPONENTS OF THE 6-12HR DISTILLATION FRACTION FROM ALASKA CEDAR, LEYLAND CYPRESS AND MONTEREY CYPRESS ANALYZED BY GC-MS ......30 4 THE COMPONENTS OF THE 6HR DISTILLATION FRACTION FROM ALASKA CEDAR FRESH WOOD AND LUMBER ANALYZED BY GC-MS.................................31 5 THE COMPONENTS OF THE 24HR SOLVENT EXTRACTION FRACTION FROM ALASKA CEDAR, LEYLAND CYPRESS AND MONTEREY CYPRESS ANALYZED BY GC-MS...............................................................................................................32 6 THE COMPONENTS OF THE 24HR AND 24-48 HR SOLVENT EXTRACTION FRACTION FROM MONTEREY CYPRESS
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