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Chemical Composition of Lantana (Lantana Camara L.) Leaves Essential Oil and Its Antimicrobial Activity

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Chemical Composition of Lantana (Lantana Camara L.) Leaves Essential Oil and Its Antimicrobial Activity Chemical Composition of Lantana (Lantana camara L.) Leaves Essential Oil and its Antimicrobial Activity By Nosiba Hassan Elsheikh Idris B.Sc. (Honors) in Agricultural Sciences (Horticultural Sciences) Faculty of Agricultural Sciences, University of Gezira (1998) M.Sc. in Horticultural Sciences, University of Gezira, (2008) A Thesis Submitted to the University of Gezira in Fulfillment of the Requirements for the Award of the Degree of Doctor of Philosophy in Oil Chemistry National Oil Seed Processing Research Institute (NOPRI) University of Gezira August, 2013 Chemical Composition of Lantana (Lantana camara L.) Leaves Essential Oil and its Antimicrobial Activity By Nosiba Hassan Elsheikh Idris Supervision Committee: Name Position Signature Dr. Nour Ahmed Osman Main Supervisor ……… Prof. Nafisa Elmahi Ahmed Co- Supervisor ………. Dr. Atif Abdel monium Ahmed Co- Supervisor ……… i Chemical Composition of Lantana (Lantana camara L.) Leaves Essential Oil and its Antimicrobial Activity By Nosiba Hassan Elsheikh Idris Examination Committee: Name Position Signature Dr. Nour Ahmed Osman Chairman ………………. Dr. Salah Mohamed Nour External Examiner …….………… Dr. Salih Mohamed A. Abbaker Internal Examiner ……………….. Date of Examination: 15/8/2013 ii Declaration I here declare that the results and findings of this research are original graphs, tables , figures and photos are genuine and they are not reproduced or extracted from any other research. Nosiba iii Dedication For My Brothers Elsir and Zahir iv ACKNOWLEDGEMENTS I would like to thank all those who participated in this work. Special thanks to my supervisor Dr. Nour Ahmed Osman who generously provided her time, effort and advice to make this work possible. Her support has been valuable during all the stages of the work. She spent much of her time organizing and discussing the different aspects especially in the identification and elucidation of the active ingredients my heart felt gratitude to my co-supervisors Prof. Nafisa Elmahi Ahmed, ARC and Dr. Atif Abdelmonium Ahmed, NOPRI, for all the kind efforts exerted in guiding me and the valuable comments and suggestions offenet during this study. My deeps thanks are due to Prof. Salah Ahmed Ali Elhussien for this topic, his genuine guidance and invaluable support. I am also greatly indebted to the staff of the food Technology Laboratory, Ustaz Hassan Ansary and his steam, University of Gezira, Ustaz Khalid Dafalla Abu Idris (ARC) Plant Pathology Lab and his team, Ustaz Betijowk (ARC) Plant Pathology Lab Research Program for their great help and advice. Finally my family my father, my mother, brothers, sister, husband and daughters for their support. Sincere thanks are due to Miss Ayda Yousif for formatting this thesis. v Chemical Composition of Lantana (Lantana camara L.) Leaves Essential Oil and its Antimicrobial Activity Nosiba Hassan Elsheikh Idris A Ph.D. in Oil Chemistry (August , 2013) National Oil Seed Processing Research Institute (NOPRI) University of Gezira ABSTRACT Lantana camara (L), of the family Verbenaceae, is listed as one of the important medicinal plants of the world. The plant is an evergreen aromatic plant, found in tropical and subtropical areas around the world. In Sudan it is commonly grown as an ornamental plant and displays several flower colors combing different shades of red- yellow- purple- violet- white- orange and yellow and orange. The essential oil of Lantana camara showed a wide spectrum of antibacterial, antimicrobial, and antifungal activities. The aims of this study were to evaluate chemical composition of locally grown Lantana plants, to evaluate their content of leaf essential oil and to assay biological activities of crude and purified constituents of the essential oil against a selected bacterium and a fungus. The plants, collected from the Gezira area around Wad-Medani, were extracted by using hydro- distillation method and cold extraction technique. The crude essential oil extracts of lantana Camara Var. aculeata were tested for growth inhibition of Agrobactrium tumefaciens and Aspergillus niger using the disc diffusion method and well fungal- growth disc diffusion method. Chemical fractionations and component identification were performed using TLC, PTLC, GC/MS, MS, UV, and FTIR. The results indicated that the crude essential oils of lantana Camara Var. aculeate possessed considerable antibacterial activities, with lethal concentration (LC50) between 160- 200μl/ml and minimum inhibitory concentration (MIC) between 4 and 8 μl/ml. On the other hand, the essential oil showed significant antifungal activity resulting in 100% kill at doses of 280 and 300 μl/ml, and LC50 of 160μL/ml, and 8-12μL/ml for MIC. Of nine separated components, eluted from PTLC-plate, only two (C1 and C6) were found active against A. niger (causing antifungal inhibition of 14% and 55% respectively). The major constituents of the essential oil of Lantana camara dependent on GC/MS were limonene, C6-Ketone, the sesquiterpene -cayrophyllene, representing more than 30% of the oil. Compared with Iran(14%), China(12%), and Nigeria(13%). vi المكونات الكيميائية للزيت الطيار من أوراق الﻻنتانا وتضاده الميكروبي نسيبة حسن الشيخ إدريس دكتوراه الفلسفة في كيمياء الزيوت )أغسطس 2013م( المعهد القومي لبحوث تصنيع الحبوب الزيتية )نوبري( جامعة الجزيرة الخﻻصة نبات الﻻنتانا .Lantana camara L أحد النباتات الطبية والعطريةة الااةةة ةل العةالي ونةل تنت ةل للعائلة الفيربينية وتوجد ل ال ناطق ذات ال ناخ ال عتدل وغير ال عتدل حول العالي. ل السةواا تةع ك بنبةات للعينةة حةول ال نةةا ل وتت يةع بالواناةةا ال تلفةة التةةل ت تةون سلةة البنفسة – اﻷصةةفر – الةو ان – اﻷح ةةر – اﻷبةةي – البرتقةةالل – اﻷصةةفر والبرتقةةالل. أااةةر العيةة الطيةةا لﻻنتانةةا ةقةةد ساليةةة للت ةةاا الب تيةةرن وال ي روبل والفطرن. الادف ةن نذه الد اسةة نةو تقيةيي عاليةة العية العطةرن ال ةا وة وناتة دةد النطةاط اﻹحيائل و تي تصنيف النبات بنا ًء سل لةو اﻷ نةا ولة ل السةاب ﻹ باﻹدةا ة ل عر ةة النسةبة ال زويةة للعية الطيا ل أنواك اﻷ نا ة تلفة اﻷلوا . تي ج ع أو اب الﻻنتانةا ةةن حةول ةدينةة واةةدنل ةل وجيةة ال عيةر واسةةت لا العيةة ةناةةا بواسةةطة طريقةةة التقطيةةر ال ةةائل وباجسةةت ﻻب البةةا ا ﻹ تةةي ااتبةةا عاليةةة العيةة ال سةةت لا ةةةن Lantana camara var. aculeata دةةد ب تريةةا العقةةد ال ذ يةةة Agrobacterium tumefaciens و طر العفن اﻷسوا Aspergillus niger باسةت دا طريقةة اجنتطةا سةن طريةق نةرب ةةن الةةو ب وبطريقةةة اجنتطةةا سةةن طريةةق نةةرب نةةاةل ةةةن الفطةةر ةةل اﻷجةةا . أجريةة ت اليةةل بي يائيةةة ل عر ةةة ال ونات الرئيسية للعي الطيا لعدا تسع سينات ةن الﻻنتانا باست دا )بروةاتوجرا يا الغا /ةطيا ية ال تلةة وةطيا ية ال تلة ب ا ت ةعر ة نوية ال ربب الفعال باست دا ةطياف اﻷلةعة ت ة ال ةراء ال ةعوا ب ةول و ييةﻹ ةطيا ية اﻷلعة وب البنفس يةﻹ بروةاتوجرا يا الطبقة الرنيقةﻹ )بروةاتوجرا يا الغا /ةطيا ية ال تلة وةطيا ية ال تلة. ألا ت النتائ إل أ ي الﻻنتانةا الطيةا أبةدع عاليةة دةد الب تريةا و صةدت ني ةة جرسةة التربيةةع القاتلةةة LC50 وبانةة بةةين 160-200 ةةةاي روليتر /ةةةل ب ةةا صةةدت ني ةةة ال ةةد اﻷانةة للقتةةل MIC وبانةة بةةين 4-8 ةةةاي روليتر /ةةةةل. أةةةا الفطةةر قةةةد وصةةل نسةةبة القتةةةل إلةة 100% سنةةد ال رسةةةات 280 ةاي روليتر /ةةل و 300 ةةاي روليتر /ةةلﻹ أي ةاً صةدت ني ةة LC50 وبانة سنةد ال رسةة 160 ةةاي روليتر /ةل و MIC وبان بين 8-12 ةاي روليتر /ةل. تي صل تسعة ةرببات للعي الطيا Lantana camara var. aculeata ب روةات را يةا الطبقةة الرنيقةة ووجةد أ ا نةين قة (C6, C1) لا ةا عاليةة دةد طةر العفةن اﻷسوا بنسبة 14% و55% سلل التوالل وند وجد أ ال ونات الرئيسية للعي الطيا لﻻنتانا نةل الﻻي ةونين و ك6-بيتو و سس وتربين بيتا با يو يللين (β- caryophyllene) والذن تفوب نسبت 30% ةقا نة بالنسةبة ال وجوا ل إيرا 14% والصين 12% وني يريا %13. vi LIST OF CONTENT Page Declaration ……………………………………………………………….. iii Dedication …………...…………………………….……..……..………... iv Acknowledgements …..…………………………..…………..…………... v English Abstract …...…..………………………………….……..……...... vi Arabic Abstract ………...………………………………………….……... vi List of Contents............................................................................................ vii List of Tables ….......................................................................................... viii List of Figures….......................................................................................... ix List of Abbreviations……………………………………………………... x CHAPTER ONE:…………………………………………..……………. 1 1. INTRODUCTION …..……………………………………………… 1 1.1. Importance of natural products………………………………… 1 1.2. The plant Lantana camara..…………………………………… 3 CHAPTER TWO: ………………………………………………………. 6 2. LITERATURE REVIEW…………..……………………………… 6 2.1. Natural products……………………………………………….. 6 2.2. Plant-derived natural product …………………………………. 6 2.2.1. Primary plant products ………………………………... 6 2.2.1.1. Carbohydrates ……………………………… 7 2.2.1.2. Amino acids and proteins…………………... 7 2.2.1.3. Lipids ………………………………………. 8 2.2.2. Secondary plant products ……………………………... 10 2.2.2.1. Alkaloids……………………………………. 10 2.2.2.2. Biosynthesis………………………………… 12 2.2.2.3. Phenolic compounds………………………... 12 2.2.2.4. Flavonoid pigments……………………….. 14 2.2.2.5. Classification of flavonoids………………… 14 2.2.2.6. Isoflavonoids……………………………….. 15 2.2.2.7. Terpenoids………………………………….. 15 2.2.2.8. General properties of Terpenoids…………... 16 2.2.2.9. Biosynthetic pathways of terpenoids in plants……………………………………….. 16 2.2.2.10 Tri terpenoids…………………………........ 19 2.2.2.11 Essential (volatile) oils……………………... 22 2.2.2.12 Essential oil classes…………………………. 22 2.2.2.13 Sources of Natural Essential Oils…………. 23 2.2.2.14 Essential Oil Constituents…………………. 29 2.2.2.15 Chemical structures of essential oils……….. 29 vii 2.2.2.16 Mono terpenes……………………….…………. 31 2.2.2.17 Sesqui terpenes…………………………………. 31 2.2.2.18 Phenolic essential oils………………………..…. 32 2.2.2.19 Alcohols…………………………………………. 32 2.2.2.20 Ethers / Esters……………………..……………. 32 2.2.2.21 Ketones…………………………………...……... 32 2.2.2.22 Aldehydes………………………………………... 33 2.2.2.23 Coumarins ……………………………..……….. 33 2.2.2.24 Biosynthesis of essential oils……………..…….. 33 2.2.2.24.1 Essential oils are biosynthesized in plants two pathway………………… 36 2.2.2.25 Extraction of essential oils…………………..….. 37 2.2.2.25.1 Distillation………………………….. 37 2.2.2.25.2 Steam distillation…………………… 37 2.2.2.25.3 Cold pressing……………………….. 38 2.3. Microbes of the study…………………………….. 38 2.3.1. Cell structure and metabolism………………………… 39 2.3.2.
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