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Chemical Profile and Some Biological Activities of Extracts from Polygonum Glabrum L

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Chemical Profile and Some Biological Activities of Extracts from Polygonum Glabrum L Chemical Profile and some Biological Activities of Extracts from Polygonum glabrum L. By Nidal Ibrahim Jalal Awad B. Sc. (Honours) in Botany, Faculty of Science, University of Khartoum, 2011 A Thesis Submitted to the University of Khartoum in Fulfillment of the Requirements for Degree of M. Sc. in Botany (Biochemistry) Supervisors: Dr. Abdelazim Ali Ahmed (2014 - 2015) Dr. Gihan Omer Mohammed (July - 2016) Department of Botany Faculty of Science November, 2016 ACKNOWLEDGEMENTS Most of all I thank "Almighty Allah", with countless thanks and gratitude, for all his blessing and for giving me this great opportunity to complete this work. I gratefully acknowledge my unique, splendid and dear supervisor Dr. Abdelazim Ali Ahmed, who is an inspiring person and motivator of an entire generation of young scientists. His valuable guidance and encouragement enabled me to carry out this research work successfully. I am particularly indebted to him for his support, understanding and patience. I would like to express profound gratitude to my other supervisor Dr. Gihan Omer Mohammed for her guidance and encouragement during this study and her support of my research efforts. No word can express my deep appreciation and gratitude to Dr. Missa Mohammed Saleh, National Center for Research, for her unlimited help. I would like to acknowledge with sincere thanks and grateful all staff of Department of Botany, Faculty of Science, University of Khartoum. I would like to offer thanks to my dear friends specially Miss. Ayat Ahmed Alrasheid, who helped me during laboratory work and during thesis preparation. I am very grateful to my father, mother and my brothers for their encouragement, patience and strong support. They have always showed great interest in my education encouraging me at all time. I wish them a happy and long life. Nidal Ibrahim Jalal 2016 I CONTENTS Acknowledgements……………………………………………….. I Contents………………………………………………………….... Ii Abstract…………………………………………………………… Vi Abstract in Arabic……………………………………………….... Vii List of Tables…………………………………………………….... viii List of Figures…………………………………………………….. Ix List of Plates………………………………………………………. X CHAPTER ONE INTRODUCTION 1.1 Background…………………………………………………... 1 1.2 Objectives of the study……………………………………….. 2 CHAPTER TWO LITERATURE REVIEW 2.1 Polygonaceae family…………………………………………. 4 2.2 Study plant (Polygonum glabrum)…………………………… 4 2.2.1 Botanical description……………………………………….. 5 2.2.2 Distribution in the world and Sudan……………………….. 5 2.2.3 Traditional uses…………………………………………….. 5 2.2.4 Chemistry of the genus Polygonum………………………... 6 2.3 Metabolites in plants…………………………………………. 6 2.3.1 Primary and secondary metabolites………………………... 6 2.3.2 Secondary metabolites……………………………………... 9 2.3.2.1 Phenolic compounds……………………………………... 10 2.3.2.2 Flavonoids………………………………………………... 10 II 2.3.2.3 Tannins………………………………………………….... 11 2.3.2.4 Alkaloids…………………………………………………. 12 2.4 Antimicrobial agents…………………………………………. 14 2.5 Antioxidant activity………………………………………...… 15 2.6 Cytotoxicity and anticancer………………………………….. 16 CHAPTER THREE MATERIALS AND METHODS 3.1 Plant materials………………………………………………... 17 3.1.1 Preparation of plant extracts……………………………….. 17 3.2 Chemicals…………………………………………………….. 17 3.3 Methodology………………………………………………..... 17 3.3.1 Proximate analysis…………………………………………. 17 3.3.1.1 Determination of moisture content………………………. 17 3.3.1.2 Determination of ash content……………………….….. 18 3.3.1.3 Determination of crude fiber content……………….….. 18 3.3.1.4 Determination of crude protein of content…………….. 19 3.3.1.5 Determination of oil content………………………….... 19 3.3.1.6 Determination of total carbohydrate…………………... 20 3.3.1.7 Determination of ascorbic acid……………………….... 20 3.3.2 Mineral contents……………………………………………. 20 3.3.3 Phytochemical analysis…………………………………….. 21 3.3.3.1 Qualitative phytochemical screening………………….…. 21 3.3.3.1.1 Alkaloids……………………………………………….. 21 3.3.3.1.2 Flavonoids…………………………………………….... 22 3.3.3.1.3 Sterols…………………………………………………... 22 III 3.3.3.1.4 Triterpenes……………………………………………... 22 3.3.3.1.5 Tannins…………………………………………….…. 23 3.3.3.1.6 Saponins………………………………………………... 23 3.3.3.1.7 Coumarins……………………………………………… 23 3.3.3.2 Thin Layer Chromatography (TLC)……………………... 23 3.3.3.3 Quantitative analysis……………………………………... 25 3.3.3.3.1 Total flavonoids content……………………………... 25 3.3.3.3.2 Total tannins content……….………………………… 25 3.3.3.3.3 Total polyphenols content…..………………………….. 27 3.3.3.3.4 Gas Chromatography–Mass Spectrometry (GC/MS) 27 Analysis…………………………………………………………... 3.3.4 Bioassay methods…………………………………………... 30 3.3.4.1 Determination of antimicrobial activity………………….. 30 3.3.4.1.1 Assay for antibacterial activity………………………… 32 3.3.4.1.2 Bioassay for antifungal activity………………………... 32 3.3.4.2 Determination of antioxidant activity……………………. 33 3.3.4.3 Cytotoxicity assay……………………………………….. 33 CHAPTER FOUR RESULTS AND DISCUSSION 4.1 Proximate analysis and vitamin C content………………….. 36 4.2 Mineral content……………………………………………..… 38 4.3 Phytochemical analysis……………………………………….. 40 4.3.1 Yield and physical characteristics………………………..... 40 4.3.2 Qualitative phytochemical screening………………………. 40 4.3.3 Thin Layer Chromatography (TLC)……………………..... 44 4.3.4 Quantitative analysis……………………………………….. 46 IV 4.3.4.1 Flavonoids content……………………………………….. 46 4.3.4.2 Tannins content…………………………………………... 48 4.3.4.3 Polyphenols content……………………………………... 48 4.3.4.4 Gas Chromatography–Mass Spectrometry (GC/MS) analysis……………………………………………………………. 51 4.4 Biological activities…………………………………………... 59 4.4.1 Antimicrobial activity……………………………………... 59 4.4.2 Antioxidant activity……………………………………….. 69 4.4.3 Cytotoxicity………………………………………………... 72 CONCLUSION…………………………………………………... 75 RECOMMENDATIONS……………………………………….... 76 REFERENCES.………………………………………………….. 77 V Abstract Traditionally, Polygonum glaburm has been used as a leafy vegetable food (young leaves) and in the treatment of some diseases. This study aimed at evaluating the phytochemicals of the plant and their biological activities as well as the nutrient components of the young leaves. Moisture, ash, fiber, crude protein, oil, carbohydrate, mineral, vitamin C, flavonoid, tannin, polyphenol and alkaloid contents were quantitatively determined. Colorimetric, spectrophotometric, Atomic Emission Spectroscopy and Gas Chromatography–Mass Spectrometry methods were used for chemical analysis. The extracted phytocomponents were assayed for their antibacterial (Staphylococccus aureus, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi) and antifungal (Candida albicans and Aspergillus niger), antioxidant and cytotoxic properties using disc diffusion, radical scavenging and microculture tetrazolium methods, respectively. Chemical analysis revealed that young leaves contained high amount of carbohydrate (53.04%), K (17260 ppm), Ca (16650 ppm), Fe (3631 ppm) and moderate amount of crude protein (7.63%), vitamin C (62.82 mg/100g) and low amount of oil content (1.87%). Amount of flavonoids in plant parts was ranging from 12 – 58.8 mg/g, tannin from 16.32 – 37.1 mg/g and polyphenols from 9.6 –31.3 mg/g. Methyl 4-(2-phenyl-1H-benzimidazole- 1-yl) phenyl ether (9.32%), imidazol-1-yl-3-methylbut-2-en-1-one (0.23%) and 2H- imidazole-2-thione (0.85%) compounds were detected in the dry leaves. These alkaloid compounds and their derivatives have been reported to possess a number of interesting biological activities. Pseudomonas aeruginosa growth was inhibited by leaves (30 mm), flowers (28 mm) and stems (24 mm) extracts. Methanol extract of the flowers had potent antioxidant activity (91.6%, IC50 = 4.134 mg/ml). Plant extracts were not toxic to normal cells (IC50< 100 ppm). To summarize, the richness of young leaves in micronutrients (minerals, vitamin C and antioxidants) and carbohydrates could support it’s used as leafy vegetable food especially in rural areas. Plant extracts which showed antibacterial and antioxidant activities strength the traditional use of the plant in folk medicine. المستخلص VI تقليدياً يستخدم نبات التمساحية )الصفصاف( كغذاء )اﻷوراق الحديثة( ولمعالجة بعض اﻷمراض. هدفت هذه الدراسة لتقييم المواد الفيتوكيميائية، النشاطات البيولوجية والمكونات المغذية لﻷوراق الحديثة. تم تحديد كمية الرطوبة، الرماد، اﻷلياف، البروتينات، الزيوت، الكاربوهيدرات، العناصر المعدنية، فيتامين جـ، الفﻻفنويدات، التانينات، الفينوﻻت العديدة و القلويدات. أستخدمت طرق القياس اللوني، المطياف الضوئي، مطياف اﻹنبعاث الذري وكروماتوغرافيا الغاز/ مطياف الكتلة لتحليل المكونات الكيميائية. أختبرت مستخلصات المركبات النباتية كمضادات للبكتريا )المكورة العنقودية الذهبية، اﻻشريشية القولونية، الزائفة الزنجارية والسالمونيﻻ التيفودية( ومضادات للفطريات )المبيضة البيضاء والرشاشية السوداء(، مضادات لﻷكسدة وخواص سميتها تجاه الخﻻيا وذلك بإستخدام طرق قرص اﻹنتشار، إزالة الجذور والتزريع المصغر للتيترازوليم، على التوالي. أظهر التحليل الكيميائي أن اﻷوراق الحديثة إحتوت على كمية كبيرة من الكربوهيدرات )53.04٪(، البوتاسيوم )17260 جزء من المليون(، الكالسيوم )16650 جزء من المليون(، الحديد )3631 جزء من المليون( وكمية معتدلة من البروتين الخام )7.63٪(، وفيتامين جـ )62.82 ملج/100ج( وكمية قليلة من الزيت )1.87٪(. تراوحت كمية الفﻻفنويدات في أجزاء النبات من 12 - 58.8 ملج/ج، التانينات من 16.32 - 37.1 ملج/ج والفينوﻻت العديدة من 9.6 - 31.3 ملج/ج. تم الكشف عن مركبات ميثيل 4- )2- فينيل -1- هيدروجين – بنزيميدازول -1- يل( اﻹيثر فينيل )0.32٪(، إيميدازول -1- يل - 3- ميثيل بيوت -2- )0.23٪( و2- هيدروجين – إيميدازول – -2 ثيون )0.85٪( في اﻷوراق الجافة. هذه المركبات القلويديه ومشتقاتها وجد أن لها عدد من اﻷنشطة البيولوجية المهمة. تم تثبيط نمو بكتيريا الزائفة الزنجارية بواسطة مستخلصات اﻷوراق )30 ملم( واﻷزهار )28 ملم( والسيقان )24 ملم(. مستخلص اﻷزهار الميثانولي
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