I= ISOLATION AND STRUCTURAL STUDIES ON THE CHEMICAL CONSTITUENTS OF WITHANIA SOMNIFERA, FUMARIA FLABLELLATA AND X-RAY DIFFRACTION STUDIES
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Title of Thesis
ISOLATION AND STRUCTURAL STUDIES ON THE CHEMICAL CONSTITUENTS OF WITHANIA SOMNIFERA, FUMARIA FLABLELLATA AND X-RAY DIFFRACTION STUDIES

Author(s)
Farzana Akhtar
Institute/University/Department Details
H.E.J Research Institute Of Chemistry/ University Of Karachi
Session
1997
Subject
Chemistry
Number of Pages
275
Keywords (Extracted from title, table of contents and abstract of thesis)
withania somnifera, fumaria flablellata, x-ray diffraction, withanolide, isoqunioline, x-ray crystal, crystal lattice

Abstract
This dissertation describes the phytochemical investigations on two medicinally important plants namely withania somnifera and fumaria flabellata. A separate section on X-ray diffraction studies o some natural and synthetic products is also included in this thesis.

Studies on chemical constituents of withania somnifera have led to isolation of a new withanolide, somilactone (101) along with the four known withanolides, (-)-sominolide (102), (-)sominohe (103), mindabeolide-1(104), and withanolide-R (105).

A new isoquinoline alkaloid flabelline (106) has been isolated form fumaria flabellata, of Turkish origin. In addition eleven known alkaloids corydaldine(107), Oxyhydrastine (108), fumaritine (109), protopine (110), fumariline (111), tetrahydropalmatine (112), N-feruloy1tyramine (113), juziphine (114), (+)-bicuclline (115), (-)corlumine (116), and O-methy1fumarophcine (117) have also been isolated for the first time form this source.

Structures of these new and known natural product were determined on the basis of extensive spectroscopic studies including one-, two-and inverse two-dimensional NMR experiments (such as COSY, HOHAHA, HMQC, HMBC etc.).

The second half of this thesis comprises on three dimensional structural determination of natural and synthetic products by X-ray diffraction analysis. Structure of a novel triterpene perovskone (130) isolated from perovuskia abrotanoides, two antifungal diterpenoidal non-alkaloids 8-acety1herophllisine (131), and panicutine(132), and a non-alkaloid 3-hydroxy-2-methy1-4H-pyran-4-one (133) isolated form delphinium denudatum, structures of three triterpenoidal compounds azadiraone (134), azadirone (135) and kulactone(136) isolated form azadirachta indica, were determined. Three new synthetic products 3,6-nahydro-4-O-[p-toluneesulfoney1] –D-glucal (137). 2(R),3(R), 2,4-dihydroxy-3-tosy1-terahydrofuran (138) and 7-[α-(hydroxyl)-m-nitrobenzy1]-8-quinolinol (139) have also been determined by X-Ray diffraction techniques.

Download Full Thesis
3045.45 KB
S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents
133.45 KB
2 1 Introduction 1
557.34 KB
  1.1 Withania Somnifera 5
  1.2 Fumaria Flabellata 28
3 2 Results And Discussion 44
626.95 KB
  2.1 New Withanolide From W. Somnifera 45
  2.2 Known Withanolides From W. Somnifera 57
  2.3 New Isoqunioline Alkaloid Isolated From F. Flabellata 69
  2.4 Known Isoqunioline Alkaloid Isolated Fro The First Time Form F. Flabellata 74
4 3 Experimental 96
254.46 KB
  3.1 General Experimental Conditions 97
  3.2 Withania Somnifera 99
  3.3 Fumaria Flabellata 106
5 4 X-Ray Diffraction Studies 122
300.4 KB
  4.1 History 124
  4.2 Application Of X-Ray Crystal Structure Analysis 127
  4.3 Background And Theory Of X-Ray Diffraction 137
  4.4 Crystal 140
  4.5 Unit Cell 141
  4.6 Crystal Systems 141
  4.7 Crystal Lattice 142
  4.8 Space Group 142
  4.9 Primitive Lattices 142
  4.10 Non-Primitive Lattice 142
  4.11 Bravais Lattice 143
  4.12 Experimental Analysis 143
6 5 Results And Discussion - X-Ray Diffraction Studies 150
879.57 KB
  5.1 X-Ray Diffraction Studies On Some Natural Products 150
  5.2 X-Ray Diffraction Studies Of Some Of Some Synthetic Products 198
7 6 Experimental - X-Ray Diffraction Studies 219
243.88 KB
  6.1 Instrumental Details 219
  6.2 General Experimental Procedure Of X-Ray Diffraction Studies 220
  6.3 Experimental Details Of X-Ray Analysis Of Perovskone (130) 225
  6.4 Experimental Details Of X-Ray Analysis Of 8-Acety1heteroph11isnie (131) 226
  6.5 Experimental Details Of X-Ray Analysis Of Panicutine (132) 227
  6.6 Experimental Details Of X-Ray Analysis Of 3-Hydroxy -2-Methy1-4-H-Pyran-4-One (133) 228
  6.7 Experimental Details Of X-Ray Analysis Of Azadiradione(134) 229
  6.8 Experimental Details Of X-Ray Analysis Of Azadirone(135) 230
  6.9 Experimental Details Of X-Ray Analysis Of Kulactone (136) 231
  6.10 Experimental Details Of X-Ray Analysis Of 3,6-Anhydro-4-O-(P-Toluenesulfony1)-D-Glucal (137) 232
  6.11 Experimental Details Of X-Ray Analysis Of 2(R) -3(R), 4-2,4-Dihydroxy-3-Toys1tetrahydrofurance(138) 233
  6.12 Experimental Details Of X-Ray Analysis Of 7-[Α-(Hydroxy)-M-Nitrobenzy1]-8-Quinolinol(139) 239
8 7 References 235
377.06 KB
  7.1 Glossary 265
  7.2 Key And Symbols 268
  7.3 Subject Index 270
  7.4 List Of Publications 274