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Phytochemical and Biological Studies of Croton Bonplandianum (Euphorbiaceae)

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Phytochemical and Biological Studies of Croton Bonplandianum (Euphorbiaceae) Phytochemical and biological studies of Croton bonplandianum (Euphorbiaceae) By Muhammad Naeem Qaisar A thesis submitted in partial fulfillment of the requirements for the degree of Doctorate of Philosophy in Pharmaceutical Chemistry FACULTY OF PHARMACY BAHAUDDIN ZAKARIYA UNIVERSITY MULTAN PAKISTAN 2015 1 Brief Contents Serial No. Contents Page No. 1 List of Abbreviations 2 List of Tables 3 List of Figures 4 Introduction 1 5 Literature review 9 6 Materials and Methods 64 7 Results 89 8 Discussions 117 9 References 120 2 Acknowledgement In the name of Allah, who has given me strength and courage to accomplish this work in the benefit of mankind. I bow my head on thanks and gratitude to Allah for his countless blessings. It is great pleasure to express my indebted gratitude to my supervisor Professor Dr. Bashir Ahmad Chaudhary for instilling in me the value of hard work, dedication and thirst for knowledge. I am greatly thankful to him for his constant care, encouragement and especially for his kind behavior. I am also thankful to Dr. Khalid Husain Janbaz, Dean Faculty of Pharmacy, Bahauddin Zakariya University Islamabad for his supportive attitude. I wish to express best regards to my co supervisor Dr. Muhammad Uzair for providing me the opportunity to work under his kind guidance and for his supportive attitude. I am also thankful to administrative staff of Faculty of Pharmacy, Bahauddin Zakariya University. I am blessed by having a friend like Sajid Nawaz Hussain who always provided support and motivation to me. His encouraging behaviour and help were always there where things didn’t seem to work. I would also like to thank my friends and lab fellows Farook Azam, Khurram Afzal, and Sadd Ullaha for providing me nice company during my research work. I would like to pay my heartiest thanks to my parents and my grandmother for their prayers, untiring efforts, supporting and encouraging behavior. Perhaps I would not be able to present this work in present form without co-operation of Higher Education Commission (HEC) Pakistan for funding me through Indigenous PhD fellowship programme. 3 Abbreviations 13C-NMR Carbon-13 Nuclear Magnetic Resonance 1H-NMR Proton Nuclear Magnetic Resonance CC Column chromatography DCM Dichloromethane DPPH 1, 1-Diphenyl-2-picrylhydrazyl HR-EI Masspec High Resolution Electron Impact mass spectroscopy IR Infrared MeOH Methanol HRMS High Resolution mass spectrometry NaOH Sodium Hydroxyde NMR Nuclear Magnetic Resonance TLC Thin layer chromatography UV Ultraviolet 4 Abstract The research work was carried out for the phytochemical and biological studies of Croton bonplandianum (Euphorbiaceae). Preliminary phytochemical screening revealed the presence of alkaloids, saponins, flavonoids, tannins and terpenoids while anthraquinone glycosides and cardiac glycosides were absent. The extraction of dried plant material was affected by dichloromethane and methanol successively. Both dichloromethane and methanol extracts were subjected to biological activities such as antibacterial, antifungal, antioxidant, α-chymotrypsin inhibitory, urease inhibitory, α-glucosidase inhibitory and butyrylcholinesterase inhibitory activities along with brine-shrimp toxicity, phytotoxicity against Lemna minor. Dichloromethane extract has shown in vitro α-glucosidase inhibitory activity of 97.89 % with IC50 value of 14.93 µg/ml compared to the standard acarbose, which exhibited 92.23 % inhibition with IC50 value of 38.25 µg/ml. Methanol extract appeared with potent butyrylcholinesterase inhibitory activity of 84.14 % with IC50 found to be 31.01 µg/ml compared to the standard eserine, which exhibited 82.82 % inhibition with IC50 value of 30.01 µg/ml. Methanol extract was found toxic with LD50 value of 115.76 (0.0048 - 13.76) µg/ml against Artemia salina and also showed radical scavenging activity (%RSA) of 59.62% with IC50 value of 396.20 µg/ml . Based on these results activity guided isolation of constituents from dichloromethane and methanol extracts were done. Fractionation of dichloromethane extract by column chromatography on silica gel and Sephadex LH 20 using different mobile phase systems led to the purification of compounds (A-I). The structures of these isolated compounds were established by spectroscopic technique such as UV and IR spectroscopy. Proton Nuclear Magnetic Resonance (1H NMR), 13C NMR and Mass spectrophotometry (EIMS, HRMS) were used for elucidation of structure. On the basis of physical and spectral data from literature, these compounds were identified as n-pentacosanyl- n-nonadeca-7′-en-9′-α-ol-1′-oate (A), n-tridecanyl n-octadec-9,12-dienoate (B), nonacosyl hexadecanoate (C), heptacosanoic acid (D), 1,3,5-trihydroxy-2-hexadecanoylamino-(6e,9e)- heptacosdiene (E), coumarin (F), betulin (G), stigmasterol (H), and 3,5-dimethoxy 4-hydroxy cinnamic acid (I) were isolated. All these compounds were screened for in vitro α-glucosidase inhibitory activity, compound F, G and I possessed significant α-glucosidase inhibitory activity in a concentration-dependent manner and explained more potent inhibitory activity with IC50 values ranging from 23.0 to 26.7 μg/ml than that of a positive control acarbose (IC50, 38.2 5 µg/ml). Fractionation of methanol extract by column chromatography on silica gel using different mobile phase system afforded five compounds (J-N). Based on spectral data the chemical structure has been established as 4-hydroxy-3,5-dimethoxybenzoic acid (J), 5,8- dihydroxycoumarin (K), stigmasterol 3-O- β -D-glucoside (L), sparsifol (M) and 6-O-β-D- glucopyranosyl-β-D-(1-O-sinapoyl,6'-O-sinapoyl)-glucopyranose (N) were isolated from methanol extract of Croton bonplandianum. The compounds J, K, L and N exhibited significant butyrylcholinesterase inhibitory activity in a concentration-dependent manner and exhibited potent inhibitory activity with IC50 values ranging from 21.0 to 36.0 μg/ml, than that of a positive control eserine (IC50, 32.0 µg/ml). 6 CONTENTS 1. Introduction 1 1.1 Secondary metabolites 1 1.1.1 Alkaloids 2 1.1.2 Phenolics 2 1.1.3 Terpenoids 3 1.1.4 Tannins 3 1.1.5 Glycosides 4 1.2 Botanical aspects of Euphorbiaceae 4 1.2.1 Classification 4 1.2.2 Botanical aspects of genus Croton 5 1.2.3 Croton bonplandianum 5 1.3 Aims and objective 8 2 Literature review 9 2.1 Ethnomedicinal uses of Croton species 9 2.2 Previous phytochemical reports on genus Croton 20 2.2.1.1 Aporphine 20 2.2.1.2 proaporphine 21 2.2.1.3 Morphinane Dienone 24 2.2.1.4 Protoberberine 25 2.2.1.5 Glutarimide 26 2.2.1.6 Guaiane 26 2.2.1.7 Harman 27 2.2.1.8 Tyramine 27 2.2.1.9 Benzylisoquinoline 27 2.2.1.10 Peptide derivatives 27 2.2.1.11 Miscellaneous alkaloids 27 2.2.2 Flavonoids 29 2.2.3 Terpenoids 31 7 2.2.3.1 Monoterpenes and sesquiterpenes 31 2.2.3.2 Diterpenoids 32 2.2.3.2.1 Acyclic diterpenoids 32 2.2.3.2.2 Bicyclic diterpenoids 33 2.2.3.2.3 Clerodane diterpenoids 33 2.2.3.2.4 Halimanes and an indane derivatives 37 2.2.3.2.5 Labdanes 38 2.2.3.3 Tricyclic diterpenoids 40 2.2.3.3.1 Abietanes 40 2.2.3.3.2 Daphnanes 41 2.2.3.3.3 Pimaranes and isopimaranes 41 2.2.3.4 Tetracyclic diterpenoids 42 2.2.3.4.1 Atisanes 42 2.2.3.4.2 Kauranes 42 2.2.3.5 Pentacyclic diterpenoids 47 2.2.3.6 Macrocyclic diterpenoids 48 2.2.3.7 Limonoids 50 2.2.3.8 Triterpenoids 50 2.2.4 Phytosterols 53 2.2.5 Fixed oils 55 2.3. Previous pharmacological reports on Genus Croton 55 2.3.1 Antioxidant activity 55 2.3.2 Antidiarrhial activity 56 2.3.3 Antimicrobial activity 56 2.3.4 Antimalarial activity 57 2.3.5. Antiulcer activity 58 2.3.6. Anticancer activity 58 2.3.7. Antihypertensive activity 60 2.3.8. Antiinflammatory and antinociceptive 60 2.3.9. Antidepresant activity 61 2.3.10 Antihyperlipidemic and antihypercholestrolemic activity 61 8 2.3.11 Antiviral activity 62 2.3.12 Vasorelaxant activity 62 2.3.13 Antioestrogenic activity 62 2.3.14 Insecticidal activity 62 2.3.15 Antileishmanial activity 62 2.3.16 Antispasmodic activity 63 2.3.17 Phyt otoxic activity 63 3. Material and methods 64 3.1 Collection of plant material 64 3.2 Solvents and chemicals 64 3.3 Preparations of reagents 64 3.3.1 Wagner’s reagent 64 3.3.2 Mayer’s reagent 64 3.3.3 Hager’s reagent 64 3.3.4 Dragendroff’s reagent 65 3.3.5 Godine reagent 65 3.4 Preparation of solutions 65 3.4.1 Preparation of dilute HCl 65 3.4.2 Preparation of dilute ammonia solution 65 3.4.3 Preparation of 70% alcohol 65 3.4.4 Preparation of lead subacetate solution 65 3.4.5 10 M NaOH 65 3.4.6 10% Ferric chloride solution 66 3.4.7 3.5% Ferric chloride in glacial acetic acid 66 3.4.8 1% Gelatin solution in 10% Sodium chloride 66 3.4.9 10% Sulphuric acid 66 3.5 Phytochemical methods 66 3.5.1 Preliminary phytochemical screening of plant material 66 3.5.1.1 Detection of alkaloids 66 9 3.5.1.2 Detection of anthraquinone glycosides 67 3.5.1.3 Detection of cardioactive glycosides 67 3.5.1.4 Detection of tannins 67 3.5.1.4.1 Ferric chloride test 67 3.5.1.4.2 Gelatin test 68 3.5.1.4.3 Catechin test 68 3.5.1.5 Tests for saponin glycosides 68 3.5.1.6 Detection of flavonoids 68 3.5.1.7 Detection of terpenoids 68 3.6 Extraction 68 3.7 Chromatographic Method 69 3.7.1 Thin Layer Chromatography 69 3.7.1.1 Visualisation of components on TLC plates 69 3.7.2 Column Chromatography 69 3.8 Spectroscopy 71 3.9 Physical and Spectroscopic data of isolated compound(A-I) 72 3.9.1 Compound A 72 3.9.2 Compound B 73 3.9.3 Compound C 73 3.9.4 Compound D 74 3.9.5 Compound E 75 3.9.6 Compound F 76 3.9.7 Compound G 77 3.9.8 Compound H 77 3.9.9 Compound I 78 3.9.10 Compound J 79 3.9.11 Compound K 80 3.9.12 Compound L 81 3.9.13 Compound M 82 3.9.14 Compound N 82 3.10 Biological methods 83 10 3.10.1 Antibacterial assay 83 3.10.2 Antifungal assay 84 3.10.3 Antioxidant assay 84 3.10.4 Cytotoxic assay 85 3.10.5 Phytotoxic assay 85 3.10.6 Urease inhibition assay 86 3.10.7 α-Chymotrypsin inhibition assay 86 3.10.8 α-glucosidase inhibition assay 87 3.10.9 Butyrylcholinesterase inhibition assay 87 4.
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