I= STUDIES ON THE CHEMICAL CONSTITUENTS OF CADABA FARINOSA
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Title of Thesis
STUDIES ON THE CHEMICAL CONSTITUENTS OF CADABA FARINOSA

Author(s)
Aziz-Ur-Rehman Amber
Institute/University/Department Details
University of Karachi./H.E.J. Research Institute of Chemistry.
Session
1990
Subject
Chemistry
Number of Pages
148
Keywords (Extracted from title, table of contents and abstract of thesis)
cadaba farinosa, (synfruticosa, l. druce.), a-b-dihydro ferulic acid, spermidine alkaloid, cadabicine methyl ether, capparisine, cadabicilone, cadabicine diacetate

Abstract
The “Studies on the chemical constituents of cadaba farinose forssk (synfruticosa, L. Druce.)” have led to the isolation of three novel spermidine alkaloids, one novel sesquiterpenoid, alongwith another spermidine alkaloid, pprisine and an aromatic acid, a,b-Dihydro ferulic acid. The last two mpoounds were isolated from this genus for the first time.

The thesis also includes the total synthesis of a spermidine alkaloid, iabicine methyl ether. The three novel spermidine alkaloids named as cadabicine, cadibicine methyl ether and cadabicine diaceteate, have the same skeletal system. They are rocyclic alkloids containing hydroxylated, methoxylated or acetylated, trans ferulic acid residues which are linked to each other through oxygen bridge and spermidine, through amide bonds. These type of compounds may exist in two to isomeric forms with respect to spermidine moiety. The spectral data londing, UV, IR, 1H-NMR cannot decide the exact structure of such ers but their structure can be confirmed by X-rays crystallography or ugh mass spectral fragmentation pattern.

The structure of cadabicine was confirmed through X-ray analysis. The structure of cadabicine methyl ether was elucidated by mass spectral sentation and comparison with cadabicine and inally confirmed by its total thesis. Similarly the structure of cadabicine diacetate was confirmed through spectral fragmentation pattern, other modern spectroscopic methods and it comparison with cadabicine and its diacetyl derivative. Their structures live below.

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S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Cotents
31.98 KB
2 1 Summary 1
43.3 KB
3 2 Introduction 7
268.57 KB
  2.1 General Introduction 8
  2.2 Spermidine alkaloids 15
  2.3 Sesquiterpenes 28
  2.4 Botanical description of Cadaba farinose 38
  2.5 Medical Importance of Cadaba farinose 39
  2.6 Literature Review Cadaba farinose 40
4 3 Present work (Results and Discussion) 44
516.26 KB
  3.1 Cadabicine 45
  3.2 Cadabicine methyl ether 60
  3.3 Synthesis of cadabicine methyl ether 73
  3.4 Cadabicine diacetate 80
  3.5 Capparisine 91
  3.6 Cadabicilone 99
  3.7 a-B-Dihydroferulic acid 108
5 4 Experimental 115
243.31 KB
  4.1 General Notes 116
  4.2 Isolation of cadabicine 119
  4.3 Acetylation of cadabicine 121
  4.4 Isolation of cadabicine methyl ether 123
  4.5 Formation of N-acetyl cadabicine methyl ether 126
  4.6 Synthesis of cadabicine methyl ether 128
  4.7 Isolation of Cadabicine diacetate 134
  4.8 Isolation of Capparisine 137
  4.9 Isolation of Cadabicilone 139
  4.10 Isolation of a-B-Dihydro ferulic acid 141
6 5 References 143
45.35 KB
7 6 Publications 147
26.5 KB