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PHYTOCHEMCIAL STUDIES OF SOPHORA GRIFFITHII, PETCHIA CEYLANICA AND ZIZYPHUS LOTUS AND SYNTHESIS OF ASARONE ANALOGUES

Muhammad, Saleh Ajaz (1993) PHYTOCHEMCIAL STUDIES OF SOPHORA GRIFFITHII, PETCHIA CEYLANICA AND ZIZYPHUS LOTUS AND SYNTHESIS OF ASARONE ANALOGUES. PhD thesis, University of Karachi, Karachi.

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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

Item Type:Thesis (PhD)
Uncontrolled Keywords:sophora griffithii, petchia ceylanica, zizyphus lotus, asarone analogues, sophoattarine, sophohehjrine, sophosalimine, n-methylsopholupisine, sopholupanozidone, sparteine n-oxide, cytisine, argentine, dihydroxypetchenol, lotusanine
Subjects:Physical Sciences (f) > Chemistry(f2)
ID Code:1228
Deposited By:Mr. Muhammad Asif
Deposited On:04 Jan 2007
Last Modified:04 Oct 2007 21:05

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