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Isolation and Identification of House Fly, Musca Domestica L., Repellents In

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Isolation and Identification of House Fly, Musca Domestica L., Repellents In Nationai Library d Canada The quality of this microform is La qualite de cette microforme heavily dependent upon the depend grandement de la qualite quaiity 00 the original thests de la thBse soumise au submitted for microfilming. M1l;erdiimage. Nous avons tout Every effort has been made to fait pour assurer une qualit6 ensure the highest quality of superieure de reproduction. reproduction possiMe. If pages are missing, contact the S'il manque des pages, veuiliez university which granted the communiquer avec I'universite degree. qui a confere le grade. Some pages may have indistinct La qualite d'impression de print especially if the original certaines pages peut laisser a pages were typed with a poor desirer, surtout si les pages typewriter ribbon or if the originales ont ete university sent us an inferior dactylographiees a I'aide d'un phobcopy. ruban use ou si l'universite nous a fait parvenir une photocopie de qualit6 inferieure. Reproduction in full or in part of La reproduction, meme partielle, this microform is governed by de cette microforme est soumise the Canadian Copyright Act, ii la Loi canadienne sur le droit R 4970, c. C-30, 2nd d'aaateur, SRC 1970, c. C-30,e4 subsequent amendments. ses amendements subs6quents. BSc. (Hons.), University of Kelaniya, Kelaniya, Sri Lanka, 1985 A TKESIS SUBMImD IN PARTIAL FULFELNIENT OF TKE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE in the Department of Chemistry @ Priyantha Dharshana Chandmakumara Wimalaratne, 1993 SIMON FRASER UNIVERSI?TY July 1993 rights reserved. This thesis may not be reproduced in whole or in part, by photocopy or other means, without permission of the author. Acquisitions and Direction des acquisitions et BiMii~aphicServices Branch cfes services bibl~lgraphiques The author has granted an Cauteur a accorde une licence irrevocable non-exclusive licence irrevocable et non exclusive aliowing the Nationai Library of permettant & la Bibliotheque Canada to reproduce, loan, nationale du Canada de distribute or sell copies of reproduire, prgter, distribuer ou - his/her thesis by any means and vendre des copies de sa these in any form or format, making de quelque maniere et sous this thesis available to interested quelque forme que ce soit pour persons. mettre des exemplaires de cette these a fa disposition des personnes interessees. The author retains ownership of L'auteur conserve la propri6t6 du the copyright in his/her thesis. droit d'auteur qui protege sa Neither the thesis nor substantial these. Ni la th9se ni des extraits extracts from it may be printed or substantiels de celle-ci ne otherwise reproduced without doivent Btre imprimes ou his/her permission. autrement reproduits sans son - autorisation. ISBN 0-315-91331-2 Title af Thesis: Isofation and Identification of House Ff_v, Musca domestics L., Repeilents in the Pepper Tree, Schinus molle L. Examining Committee: Chair: Dr. D. Sutton Or. 3.H. Barden (Professor), Biulogical Sciences Committee Member Dr. 5. Holdemfi (&itant Professor) Committee Member InternaI Examiner: Dr. A. Bemet (Assistant Professor) PARTIAL COPYRIGHT LICENSE t hereby grant to Simon Frassr University the right to lend my thesis, projecl or extended essay (the titie of which is shown below) to users of the Simon Frzser University Library, and to make partial or single copies only for such users or in response to a request from the library of any other university, or other educational institution, on its own behalf or for one of its users. I further agree that permission for multiple copying of tnis work for scholarly purposes may be granted by me or the Dean of Graduate Studies. It is understood that copying or publication of this work for finmcial gain shall not be allowed without my written permission. ISOLATION AND IDENTWICATION OF HOUSE FLY, Muscu domestics L., REPEUENTS PN THE PEPPER TREE, Schinus moZle L. Author: ABSTRACT Foliage from the ""pepper" tree, Schinrts molle L., is traditionally used in Ethiopia to 'krepd"house flies, Musca dornestica L, The volatile extracts of pepper tree leaves and berries had repellent and deterrent activity against house flies in a -two-choice laboratory bioassay. Steam distaation and solvent extraction were efficient methods for extracting the active material from leaves and berries, the former providing the volatile oils in a 1% yield. Fractionation of steam-distilled volatiles with two different fractionation schemes monitored by laboratory bioassays demonstrated that activity is asmciated with two compounds. Mass spectral data indicated that both compounds have the molecular composition CIOHlsO and were probably dcahols. The two compounds were identified as cis- menth-2-en-1-ol(& slnd trans-piperibl(I3). The absolute configuration of compound B was established as (IS,GS).piperitol by comparison of acetyl lactate derivatives. Racemic A adB, were synthesized from piperitone and bioassayed with house flies. These results indicate that compound B is the mzjor active house fly repellent in the pepper tree. To my mother and in memory of my father "God in his wisdom made the fly And then forgot to tell us why ... #I - C&EN, April 12,1993 - I wish to express my sincere gratitude to my supervisor Professor K.N. Slessor for his support, guidance, encouragement and for providing an excellent work environment. I would also like to thank Professor J.H. Borden for his invaluable help, guidance and for the many helpful discussions during the course of this work. Without the benefit of generous cooperation from many others, the work described in this thesis would not have been possible. f gratefully acknowledge the time and talents that those individuals have provided, in particular, Ms. Leslie Chong for the laboratory bioassay development, Dr. Harold Pierce Jr., for his technical support during the preparation of repellent extracts, Mr. Ed Danneberg and Ms. Monika Syrzycka for performing the laboratory bioassays, and Mr. Sarath Banneheka for the statistical analysis. The skilled technical assistance of Mr. Greg Owen and Mrs. Marcelline Tracey is gratefidly acknowledged. I owe my thanks to Ms. Erika Plettner for her generosity in proof reading this thesis. Page .. APPROVAL 11 ... AESmurn 111 DEDICATION iv QUOTAT][ON v ACKNOWLEDGEMENTS vi TABU3 OF CONTENTS vii UlST OF FIGURES X .. LIST OF TABLES xlll LIST OF SCHEMES xv LIST" OF ABB-TIONS INTRODUCTION 1.1. The hcuse fly, Musca domestics L. 1.2. The pepper tree, Schinus rnolle L. 3.3 Objective EXTRACTION PROCEDURES AND RESULTS 3. ISOLATION OF REPELLENTS 13 3.1. Analytied gas-liquid chromatography 13 3.2. Fractionation of repellent extracts 13 3.2.1. Column chromatography 18 3.2.2. High performance liquid chromatography 20 3.2.3. Results 25 4. ANALYSIS OF HOUSE FLY REPELLENTS 47 4.1. Experimental 47 4.1.1. Gas-liquid chromatogmphy and Gas chromatography-mass spectrometry 4.1.2. Acetylation 4.1.3. Hydrogenation 4.1-4. Oxidation 49 4.1.5. Chiral determination using acetyl S-lactyl chloride 49 4.2. Results 50 4.2.1. Identification of house fly repellents A and B 50 4.2.2. Determination of chirality of pepper tree derived, trans-piperitol 61 5. SYNTHESES AND BIOASSAY OF CIS-MENTH-2-EN-1-OL (A) AND TRANS-PIPERITOL (B) 66 5.1. Synthetic approaches 66 5.2. Synthesis hmpiperitone 5.3. Stereoselective metal hydride reduction 5.3. I. Experimental 5.4. Acid at;at!yz& reamngemeift of cis-piperitol 5.4.1. Experimental Comparison of synthetic and natural materials Bioassay of synthetic repellents REFERENCES Page Figure 3.1 GC chromatctgram (GG-1) of the pentane extract of steam-distilled volatile extracts of pepper tree leaves 15 Figure 3-2 GC chromatqpm (GC-1) of the final behaviorally active fraction 5 (Table 3.8) obtained from the repeated HPLC fractionation (HP-1,2 and 3) of active principle in fraction 7 (Table 3.5) that eluted with 50% e&er!penfane in LC fractionation of steam- distilled volatile extracts of pepper tree leaves, Comprrmds A and B are the major constituents 35 Figure 3.3 GC chromatogram (GC-1) of the behaviorally active &action 4 (Table 3-91eluted with 15%etherhexane in dire& HPLC fractionation (HB-4) of steam-distilled volatile extracts of pepper tree leaves. Compounds A and B correspond to the same compounds in Figure 3.2 36 Figure 3.4 GC chomabgram (GC-1) of the final behaviorally active fraction 14 (Table 3.11) obtained from the repeated fractionation of active principle in fraction 4 in Table 3.9 that eluted with 15%etherhexane by HPLC fractionation (KP-1 and 2) of steam-distilled volatile extracts of pepper tree leaves. Compounds A and B correspond to the same compounds in Figure 3.2 43 Figure 3.5 GC chromatog~am(GC-1) ofthe behaviorally active fraction 4 (Table 3.5) eluted with 10% eether/pentane in LC fractionation of steam- distZed vulatde extracts of pepper tree leaves, Cornpound A cornsponds to the same compound in Figure 3.2 45 Figure 3.6 GC: chromatogram (GC-1) of the bhaviorafly active fraction 7 (Table 3.5) duted with 50% ether/peniane in in fractionation of steam- &stifled volatile extracts of pepper tree leaves. Compounds A and B correspond to the same compsunds in Figure 3.2 46 Figure 4.3 GC chromatagram (GC-1) of the acety1ai;ed final behaviorally active fraction. Compound C is identical fa compohlnd A in Figure 3.2 and compund It) is the acetyiated Gerivative of compound B in Figure 3.2 53 Figure 4.4 Ef-MS S~~&TUI][Zof cornpound D (Figure 4.3) in acetylated din& kha~oralliyactive fkaction Figure 4.5 GC chmatog-am (GC-1) of the hydrogenated find behaviodfy- active fraction. Compounds E, F and G represent the hydrogenated products of cornpounds A aad B in Figwe 3.2 Figure 4.6 GC ehromabgrarn (GC-1) ofthe products obtained from hydrogenation of acetylated behaviorally active fraction.
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