I= PHYTOCHEMCIAL STUDIES OF SOPHORA GRIFFITHII, PETCHIA CEYLANICA AND ZIZYPHUS LOTUS AND SYNTHESIS OF ASARONE ANALOGUES
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Title of Thesis
PHYTOCHEMCIAL STUDIES OF SOPHORA GRIFFITHII, PETCHIA CEYLANICA AND ZIZYPHUS LOTUS AND SYNTHESIS OF ASARONE ANALOGUES

Author(s)
Muhammad Saleh Ajaz
Institute/University/Department Details
University of Karachi/ H.E.J. Research Institute of Chemistry
Session
1993
Subject
Chemistry
Number of Pages
159
Keywords (Extracted from title, table of contents and abstract of thesis)
sophora griffithii, petchia ceylanica, zizyphus lotus, asarone analogues, sophoattarine, sophohehjrine, sophosalimine, n-methylsopholupisine, sopholupanozidone, sparteine n-oxide, cytisine, argentine, dihydroxypetchenol, lotusanine

Abstract
Studies on the chemical constituents of Sophora griffithii have led to the isolation of six new alkaloids: sophoattarine (i), sophohejrine (ii) sophosalimine (iii), N-methylsopholupisine (iv) sopholupanizidone (v) and sparteine-N-oxide (vi) In addition, two known compounds cytosine and argentine were also isolated from this source. Modern spectroscopic methods were employed to determine their structures including mass, nmr and ftir spectroscopy. In the mass spectroscopic experiments, high resolution mass spectroscopy, exact mass measurements and link scan experiments were conducted. In nmr spectroscopy, besides routine experiments were conducted. In nmr spectroscopy, besides routine experiments such as 1H-NMR, 13C-NMR, Broad band, DEPT and COSY 45º, some advanced techniques were also employed. These included inverse nmr experiments such as HMGC (one-band C-H connectivities), HMBC (multiple-bond C-H connectivities) and HOHAHA (long range H-H couplings). The stereochemistry of various asymmetric centres was established by extensive NOE difference studies.

Similarly, a new triterpene – dihydroxypetchenol (vii), has also been isolated from petchia ceylanica, a Sri Lankan plant. The modern spectroscopic techniques available at HEJ research institute were employed for the correct assignment of functionalities present in this triterpene

Moreover, a cyclopeptide – lotusanine-A (viii), was also isolated from Zizyphus lotus, a Jordanian plant. Its structure was also confirmed by employing the above mentioned spectroscopic techniques. Biosythetic routes to all the isolated natural products have also been proposed

In addition synthesis of asarone, a natural product containing pesticidal activity, was also accomplished by a simple route. The chloro-analogues of this compound were also synthesized and their pesticidal activities were studied

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1282.53 KB
S. No. Chapter Title of the Chapters Page Size (KB)
1 0 Contents 0
91.47 KB
2 1 Introduction 1
319.52 KB
  1.1 Sophora Griffithii 4
  1.2 Petchia Ceylanica 26
  1.3 Zizyphus Lotus 31
3 2 Results And Discussion 37
723.08 KB
  2.1 Sophoattarine 38
  2.2 Sophohehjrine 53
  2.3 Sophosalimine 64
  2.4 N-Methylsopholupisine 73
  2.5 Sopholupanozidone 78
  2.6 Sparteine N-Oxide 84
  2.7 Cytisine 91
  2.8 Argentine 94
  2.9 Dihydroxypetchenol 98
  2.10 Lotusanine A 107
4 3 General Experimental 112
177.76 KB
  3.1 Instrumental Details 114
  3.2 Sophora Griggithii 118
  3.3 Pethchia Ceylanica 132
  3.4 Zizyphus Lotus 135
5 4 Syntheses Of Asarone Analogues 139
111.93 KB
  4.1 Introduction 139
  4.2 Chemistry Of The Reaction 142
  4.3 Insecticidal Studies 147
  4.4 General Experimental Procedures 150
6 5 References 154
55.18 KB