I= CHEMICAL AND BIOLOGICAL STUDIES ON SOME MEMBERS OF ASTERACEAE FAMILY AND PSEUDOCALYMMA ELEGANS, A NATIVE OF BRAZIL
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Title of Thesis
CHEMICAL AND BIOLOGICAL STUDIES ON SOME MEMBERS OF ASTERACEAE FAMILY AND PSEUDOCALYMMA ELEGANS, A NATIVE OF BRAZIL

Author(s)
Muhammad Jahangir
Institute/University/Department Details
H.E.J. Research Institute of Chemistry/ University of Karachi
Session
2001
Subject
Chemistry
Number of Pages
212
Keywords (Extracted from title, table of contents and abstract of thesis)
asteraceae family, pseudocalymma elegans, terrestrial plant, bignoniaceous plant, asteraceous plants, pulicaria gnaphalodes (vent.) boiss, tridax procumbens l., artemisia scoparia waldst, pseudocalymma elegans(vell.) kuhlm

Abstract
The work embodied in this dissertation in mainly concerned with the isolation and characterization of chemical constituents from terrestrial plant. The isolated compounds were either new or previously been reported in the literature. They were characterization by various sophisticated spectroscopic techniques available at this institution.

The first chapter is a general article describing about medicinally important plants and drugs from them as a gift of nature to us. The same chapter describes various steps involved in drug discovery.

The second chapter entitled “Pulicaria gnaphalodes” shows the chemical analysis of the titled pant belonging to the family asteracease. As a results of this analysis, a new dimmer of sequiterpene (gnapholide) was isolated and characterized, along with another known dimmer of the same skeleton, a sesquiterpenoid, four flavonoids and a benzoic acid derivative reported for the first time form this source.

The third chapter entitled “Tridax Procumbens” covers the phytochemical investigations as well as syntheses of oleanolic acid derivatives, which was obtained form the titled source of the same family in good amount for biological studies. During the phytochemical analysis a new dimmer of bithiophene (tridbisbithiophene) was obtained along with four commonly known triterpenoids reported first time form this source.

The next chapter (fourth) entitled “Artemisia scoparia” shows the isolation purification and characterization of tow new benzene derivatives (scopariendiol and scoparal) a new isocoumarin (Scoparin) along with pair of isomeric coumarins (sabandin-A and B) which were ambiguously characterized previously by Reyes in 1970, together with a flavone, tow steroids and their glucosides for the first time form the is source.

The fifth and second last chapter of the dissertation is based on a plant named pseudocalymma elegens, a native of Brazil, belonging to the family bignoniaceae which was selected for phytochemical screening due to its significant toxicological features. As a re results of phytochemical screening, two new iriboiae glucosides(eleganoside- B and C) along with two flavone of glycosides were obtained for the fist time from this source.

The final chapter (sixth) covers the results obtained from four bioassays of various crude extracts, semi-pure fraction, pure compounds of above mentioned sources and enzyme inhibition study by oleanolic acid and its synthetic derivatives. The various purified samples could not be tested biologically due to, either lack of their amounts or solubility. In the end of the thesis, a list of publications made by author and published papers (to date) related to the work described in the dissertation are bound. It is to clarify here that each chapter has corresponding references, descriptions of investigated plant, survey. During the phytochemical search, altogether nine new several known constituents were obtained. As a results of this research, up till now two paper have been published, tow are submitted for publication and the remaining two are in under preparation

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1911.89 KB
S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents
125.04 KB
2 1 Thanks God For The Gift Of Medicines 6
232.33 KB
  1.1 The Life 6
  1.2 Plant Kingdom And The Situation In Pakistan 7
  1.3 Search For Biodynamic Substances 7
  1.4 Natural Products As Drugs 8
  1.5 The Medicinal Plants 10
  1.6 Idea Of Drug Designing 12
  1.7 Evolving Aspects Of The Drug Discovery Process 13
  1.8 Questions 13
  1.9 Selection Of Organisms 13
  1.10 Steps In Drug Discovery 16
  1.11 Collaboration 19
  1.12 Hit And Lead 19
  1.13 Patenting The Drug 20
  1.14 Chemical Modifications In Natural Substances 21
  1.15 Drugs And Diseases 21
  1.16 Structural Requirements For A Bioactive Molecule 22
  1.17 Intellectual Property Rights 23
  1.18 Challenges For The New Century For Natural Products 24
  1.19 Recommendations 25
  1.20 Conclusions 25
  1.21 References 26
3 2 Pulicaria Gnaphalodes (Vent.) Boiss 29
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  2.1 Asteraceae ( Compositae ) 29
  2.2 The Genus Pulicaria 29
  2.3 Chemical Literature Survey Of The Genus Pulicaria 30
  2.4 Pulicaria Gnaphalodes 31
  2.5 Chemical Literature Survey Of Pulicaria Gnaphalodes 32
  2.6 Flavonoids 34
  2.7 Physiological Properties Of Flavonoids 39
  2.8 Biosyntheses Of Flavonoids 40
  2.9 Results And Discussion 40
  2.9.1 Terpenoids 42
  2.9.2 Anabsinthin ( 1) 42
  2.9.3 Gnapholide ( 2) 45
  2.9.4 Isointermedeol ( 3) 51
  2.9.5 Flavonoids 52
  2.9.6 Artemetin ( 4) 52
  2.9.7 Casticin ( 5) 55
  2.9.8 Jaceidin ( 6) 57
  2.9.9 6-Hydroxykaempferol-3 ,5,7 -Trimethyl Ether(7) 61
  2.9.10 Benzoic Acid Derivative 63
  2.9.11 P- Methoxy Benzoic Acid( 8) 63
  2.10 Experimental 64
  2.10.1 General Notes 64
  2.10.2 Collection And Identification 65
  2.10.3 Extraction, Isolation And Characterization 65
  2.11 References 73
4 3 Tridax Procumbens L. 75
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  3.1 Botanical Descriptions 75
  3.2 Health Care Properties Of Tridax Procumbens 76
  3.3 Chemical Literature Survey Of Tridax Procumbens 76
  3.4 Biosyntheses Of Triterpenoids 78
  3.5 Oxidative Cyclization Of Squalene 80
  3.6 Cyclization Of Squalene Epoxide In Chair-Chair-Boat Sequence 80
  3.7 Non-Oxidative Cyclization Of Squalene 84
  3.8 Cyclization Of Both Ends Of Squalene 84
  3.9 Results And Discussion 85
  3.9.1 Bithiophene 87
  3.9.2 Tridbisbithiophene ( 3) 87
  3.9.3 Triterpenoids 92
  3.9.4 Taraxasteryl Acetate 92
  3.9.5 Β- Amyrenone ( 15) 94
  3.9.6 Lupeol ( 16) 96
  3.9.7 Oleanolic Acid( 17) 98
  3.9.8 Synthetic Derivative Of Oleanolic Acid 101
  3.9.8 Acetate Derivative Oleanolic Acid( 18) 102
  3.9.9 Oleanolic Acid Methyl Ester( 19)
  3.9.10 Preparation Of 3-Acetoxy-28-Methyl Ester( 20) 103
  3.9.11 Preparation Of Dihydroxy- Olide ( 21) 104
  3.9.12 Preparation Of Diacetate- Olide ( 22) 106
  3.9.13 Preparation Of Dioxo- Olide ( 23) 106
  3.10 Experimental 107
  3.10.1 Collection And Identification 107
  3.10.2 Extraction, Isolation And Characterization 107
  3.10.3 Synthetic Derivatives Of Oleanolic Acid 113
  3.10.4 Preparation Of Compound 18 113
  3.10.5 Preparation Of Compound 19 114
  3.10.6 Preparation Of Compound 20 114
  3.10.7 Preparation Of Compound 21 115
  3.10.8 Preparation Of Compound 22 116
  3.10.9 Preparation Of Compound 23 117
  3.10.10 Bioactivity 118
  3.11 References 119
5 4 Artemisia Scoparia Waldst 121
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  4.1 Botanical Descriptions 121
  4.2 The Genus Artemisia 122
  4.3 Chemical Literature Survey Of The Genus Artemisia 122
  4.4 The Steroid 126
  4.5 Biosyntheses Of Steroids 127
  4.6 Results And Discussion 128
  4.6.1 Benzene Derivatives 130
  4.6.2 Scoparal ( 7) 130
  4.6.3 Scopariendiol ( 8) 133
  4.6.4 Coumarins 134
  4.6.5 Scoparin ( 9) 134
  4.6.6 Sabandin - A( 10) Sabandin -B(11) 137
  4.6.7 Flavone 140
  4.6.8 Cirsimaritin ( 12) 140
  4.6.9 Steroids And Steroidal Glucosides 143
  4.6.10 Β- Sitosterol ( 13) 143
  4.6.11 Β- Sitosterol Glucoside ( 14) 145
  4.6.12 Stigmasterol ( 15) 146
  4.6.13 Stigmasterol Glucoside ( 16) 148
  4.7 Experimental 150
  4.7.1 Collection And Identification 150
  4.7.2 Extraction, Isolation And Characterization 151
  4.8 References 159
6 5 Pseudocalymma Elegans ( Vell .) Kuhlm 162
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  5.1 Family Bignoniaceae 162
  5.2 Medicinal Importance Of Bignoniaceous Plants 162
  5.3 Chemical Literature Survey 163
  5.4 Pseudocalymma Elegans 163
  5.5 Iridoids And Seco-Iridoids 165
  5.6 Biosyntheses Of Iridoids 165
  5.7 Results And Discussion 166
  5.7.1 Iridoid-Glucosides 168
  5.7.2 Eleganoside - A( 2) 168
  5.7.3 Eleganoside - B( 3) & C(4) 172
  5.7.4 Flavone -Glycosides 175
  5.7.5 Sorbarin ( 5) 175
  5.7.6 Triumboidin ( 6) 176
  5.8 Experimental 179
  5.8.1 Collection And Extraction 179
  5.8.2 Isolation, Purification And Characterization 179
  5.9 References 185
7 6 Bioscreening Of Chemically Investigated Plants At Crude Level 186
181.44 KB
  6.1 Aim Of Bioscreening 186
  6.2 Enzyme Inhibition 187
  6.3 Enzyme Inhibition And Drug Designing 187
  6.4 Α- Glucosidase Inhibition 188
  6.5 Oleanolic Acid And Its Derivatives 188
  6.6 Antibacterial Activity 191
  6.7 Antifungal Activity 194
  6.8 Cytotoxicity ( Brien Shrimp Bioassay) 196
  6.9 Phytotoxicity ( Lemna Bioassay 197
  6.10 Procedures For Bioassays 199
  6.10.1 Α- Glucosidase Inhibition 199
  6.10.2 Antibacterial Activity 199
  6.10.3 Antifungal Activity 199
  6.10.4 Cytotoxicity 200
  6.10.5 Phytotoxicity 200
  6.10.6 Conclusions 201
  6.11 References 203
8 7 List Of Publications 204
191.01 KB
  7.1 Published Papers 206