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Phytochemical Analysis of Antileishmanial Plants: a Drug

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Phytochemical Analysis of Antileishmanial Plants: a Drug PHYTOCHEMICAL ANALYSIS OF ANTILEISHMANIAL PLANTS: A DRUG DISCOVERY APPROACH by SAMON SHRESTHA A THESIS Submitted in partial fulfillment of the requirements for the degree of Master in Science in Chemistry to The School of Graduate Studies of The University of Alabama in Huntsville HUNTSVILLE, ALABAMA 2015 In presenting this thesis in partial fulfillment of the requirements for a master's degree from The University of Alabama in lluntsville. 1 agree that the Library of this University shall make it freely available for inspection. 1 further agree that permission for extensive copying for scholarly purposes may be granted by my advisor or. in his absence, by the Chair of the Department or the Dean of the School of Graduate Studies, h is also understood that due recognition shall be given to me and to The University of Alabama in I Iimtsville in any scholarly use which may be made of any material in this thesis. THESIS APPROVAL FORM Submitted by Samon Shrestha in partial fulfillment of the requirements for the degree of Master ol'Science in Chemistry and accepted on behalf of the Faculty of the School of Graduate Studies by the thesis committee. We. the undersigned members of the Graduate Faculty ol'The University of Alabama in I luntsville. certify that we have advised and/or supervised the candidate on the work described in this thesis. We further certify that we have reviewed the thesis manuscript and approve it in partial fulfillment of the requirements for the degree of Master of Science in Chemistry. ^ThA./, Committee chair Department Chair College Dean Graduate Dean Ml ABSTRACT The School of Graduate Studies The University of Alabama in Huntsville Dearee Master of Science College/Dcpt. Science/Chemistry Name of Candidate Samoa Shrestha Title 1'hvlochemical Analysis oi'Antileishmanial Plants: A Druti Discovery Approach Phytochemical analysis of three antileishmanial plants from Monteverde. Costa Rica and Abaco Island. Bahamas, has been carried out by use of column chromatography for phytoseparation. and NMR and IR spectroscopy for structural elucidation. Ruyschui phyltadenia contained betulinic acid as major component, with significant amount of lupeol. Eugenia monteverdensis contained (i-Sitosterol. betulinic acid and barbinervic acid. Tahehuia huluunensis contained large amount of ursolic acid. Betulinic acid inhibited promastigotes of A. amazonensis signilleanlly hut was also toxic to mouse maerophages. Lupeol and betulinic acid did not show antimicrobial activity while |5- Sitosterol inhibited Aspergillus niger strongly, Barbinervic acid expressed good inhibition of Bacillus cereus. Ursolic acid was very active againsi MCF-7 cancer cells and inhibited Staphylococcus aureus significantly. R. phyttadenia and '/'. bahamensis stand out as major sources of medicinally important compounds betulinic acid and ursolic acid respectively. Abstract Approval: Committee Chair ^> Department Chair Graduate Dean IV ACKNOWLEDGEMENTS My sincere gratitude goes to my advisor and committee member Dr. William N. Setzer for allowing me to work on this project, his understanding, and guidance with chromatographic techniques and phytochemical analysis. I would like to thank other members of my committee; Dr. Bernhard Vogler for constant helps with NMR use and structural elucidation, and Dr. Robert L. McFeeters for his valuable suggestions and belief in me. The co-operation and support of the committee members were immense and valuable for completion of this project. I am thankful to the members of Natural Product and Drug Discovery lab for making the time spent in lab enjoyable, especially Bhuwan Chhetri for his help with the chromatographic separation of Tabebuia bahamensis, and Noura Dosoky for performing the cytotoxicity tests. Thanks to Dr. Lianet Monzote and group from Institute of Tropical Medicine Pedro Kouri for performing the antileishmanial tests. Support for this work was provided in part by grants from the National Institute of Health (Grants 1 R15 GM46120-01A1 and 1 R15 CA74343-01). Dr William Haber and Dr. Robert Lawton helped in plant identification and location. I am thankful to them. Special thanks to my parents, family and friends for their support and understanding. v TABLE OF CONTENTS Page List of Figures viii List of Tables xii List of Abbreviations xiii Chapters ONE INTRODUCTION 1 1.1 Leishmaniasis 1 1.2 Plants and medicines 7 1.3 Plants and leishmaniasis 10 1.4 Plant collection site 16 1.4.1 Monteverde cloud forest 16 1.4.2 Abaco island 19 1.5 Ruyschia phylladenia 20 1.6 Eugenia monteverdensis 23 1.7 Tabebuia bahamensis 28 TWO EXPERIMENTAL 31 2.1 Study area and collection of plants 31 2.2 Antileishmanial screening of plant extracts 34 2.2.1 Antipromastigote assay 34 2.2.2 Antiamastigote assay 34 2.2.3 Cytotoxicity assay (CC50) 35 2.3 Chromatographic separation of Ruyschia phylladenia 36 2.4 Chromatographic separation of Eugenia monteverdensis 38 vi 2.5 Chromatographic separation of Tabebuia bahamensis 39 2.6 IR experiments 41 2.7 NMR experiments 41 2.8 Antimicrobial screening 42 2.9 Cytotoxicity test 43 THREE RESULTS 44 3.1 Compounds from Ruyschia phylladenia 44 3.1.1 Characterization of compound A 44 3.1.2 Characterization of compound B 57 3.2 Compounds from Eugenia monteverdensis 72 3.2.1 Characterization of compound C 72 3.2.2 Characterization of compound D 85 3.2.3 Characterization of compound E 88 3.3 Compounds from Tabebuia bahamensis 100 3.3.1 Characterization of compound F 101 3.4 Result of antileishmanial assay 113 3.5 Results of antimicrobial tests 113 3.5 Results of cytotoxicity assay 113 FOUR DISCUSSION 114 FIVE CONCLUSION 121 REFERENCES 123 vii LIST OF FIGURES Figures Page 1.1 Lifecycle of Leishmania spp. 3 1.2 Drugs used in current treatment of Leishmaniasis 6 1.3 Traditionally used medicines from plants 11 1.4 Phytochemicals used traditionally against Leishmaniasis 17 1.5 Cloudzone over Monteverde 21 1.6 Seven lifezones of Monteverde 21 1.7 Abaco Island, Bahamas 22 1.8 Ruyschia phylladenia plant 24 1.9 Leaves and fruits of Ruyschia phylladenia (a) fresh (b) dried 24 1.10 Eugenia monteverdensis tree with fruits 27 1.11 Dried leaves of Eugenia monteverdensis 27 1.12 Leaves of Tabebuia bahamensis 30 1.13 Tabebuia bahamensis plant 30 2.1 Plant collection from Monteverde, Costa Rica 32 2.2 Soxhlet extraction of crude extract 33 2.3 Column chromatography (a) empty cylinder (b) active running column 37 2.4 Chromatographic separation scheme for Ruyschia phylladenia extract 37 2.5 TLC plates under UV light 38 2.6 Chromatographic separation scheme for Eugenia monteverdensis extract 39 2.7 Crystals of SF D after Toluene slow cooling recrystallization 40 2.8 Chromatographic separation scheme for Tabebuia bahamensis extract 41 3.1 Chemical structure of lupeol 44 viii 3.2 Key HMBC correlation of compound A 46 3.3 Proton spectrum of compound A 48 3.4 Proton spectrum of compound A (major peaks) 49 3.5 Carbon spectrum of compound A 50 3.6 Carbon spectrum of compound A (closer view) 51 3.7 HSQC spectrum of compound A 52 3.8 HSQC spectrum of compound A (closer view) 53 3.9 HMBC spectrum of compound A 54 3.10 HMBC spectrum of compound A (closer view) 55 3.11 IR spectrum of compound A 56 3.12 Chemical structure of betulinic acid 57 3.13 Key HMBC and COSY correlations of compound B 59 3.14 Proton spectrum of compound B in chloroform-d 61 3.15 Proton spectrum of compound B in chloroform-d (Major peaks) 62 3.16 Proton spectrum of compound B in DMSO -d6 63 3.17 Carbon spectrum of compound B in chloroform-d 64 3.18 Carbon spectrum of compound B (closer view) 65 3.19 HSQC spectrum of compound B 66 3.20 HSQC spectrum of compound B (closer view) 67 3.21 HMBC spectrum of compound B 68 3.22 HMBC spectrum of compound B (closer view) 69 3.23 COSY spectrum of compound B 70 3.24 IR spectrum of compound B 71 3.25 Chemical structure of β-Sitosterol 72 3.26 Key HMBC and COSY correlations of compound C 74 ix 3.27 Proton spectrum of compound C 76 3.28 Proton spectrum of compound C (Major peaks) 77 3.29 Carbon spectrum of compound C 78 3.30 Carbon spectrum of compound C (closer view) 79 3.31 HSQC spectrum of compound C 80 3.32 HSQC spectrum of compound C (closer view) 81 3.33 HMBC spectrum of compound C 82 3.34 HMBC spectrum of compound C (closer view) 83 3.35 COSY spectrum of compound C 84 3.36 Proton spectrum of compound D 86 3.37 Carbon spectrum of compound D 87 3.38 Chemical structure of barbinervic acid 88 3.39 Key HMBC and COSY correlations of compound E 90 3.40 Proton spectrum of compound E 92 3.41 Proton spectrum of compound E (Major peaks) 93 3.42 Carbon spectrum of compound E 94 3.43 Carbon spectrum of compound E (closer view) 95 3.44 HSQC spectrum of compound E 96 3.45 HSQC spectrum of compound E (closer view) 97 3.46 HMBC spectrum of compound E 98 3.47 HMBC spectrum of compound E (closer view) 99 3.48 COSY spectrum of compound E 100 3.49 Chemical structure of ursolic acid 101 3.50 Key HMBC and COSY correlations of compound F 103 3.51 Proton spectrum of compound F 105 x 3.52 Proton spectrum of compound F (Major peaks) 106 3.53 Carbon spectrum of compound F 107 3.54 Carbon spectrum of compound F (closer view) 108 3.55 HSQC spectrum of compound F 109 3.56 HSQC spectrum of compound F (closer view) 110 3.57 HMBC spectrum of compound F 111 3.58 HMBC spectrum of compound F (closer view) 112 xi LIST OF TABLES Tables Page 1.1 Taxonomic classification of pathogenic Leishmania spp.
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