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STUDIES ON BIOACTIVE CONSTITUENTS FROM SPHAERANTHUS INDICUS AND BERBERIS PARKERIANA

Shah, Pir Muazzam (1991) STUDIES ON BIOACTIVE CONSTITUENTS FROM SPHAERANTHUS INDICUS AND BERBERIS PARKERIANA. PhD thesis, University of Karachi, Karachi.

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Abstract

The isolation and structure determination of those compounds are described here which are either new or which have been isolated for the first time from the plants (See below). The thesis is divided into two parts. In the fist part is described investigation of the chemical constituents of the flowers of Sphaeranthus indicus (Compositae), which afforded four new sesquiterpenes one new sesquiterpene glycoside, one known sesquiterpese, and one known steroid. The new compounds were identified as 11a, 13-dihydro-3a-(B-glucopyransoyl),7a-hydroxyfrullanolide (76) 11a, 13-dihydro-7a-hydroxy-13-methoxyfrullanolide (78), 7a-hydroxyeudesm-4-ene-6, 12-B-olide(79), 11a, 13-dihydro-7a-13-dihydroxyfrullnolide (80), 11a-13-dihydro-3a-7a-dihydroxyfrullanolide (81) while the known are caryophyllene-a-oxide (82) and 24S-stigmasta-5, 22E-diene-3B-ol (83). The second part of the thesis described studies on these chemical constituents of the roots of Berberis paarkeriana (Berberidancae). These studies have led to the isolation and identification of twonew protoberberine bases i.e parkerine (159) and 8-formylprotoberine (162). In addition five more bases have been detected. They are oxyberberine (164). 8-trichloromethyldihydroprotoberberine (165 artifact), berbamine (166), 24R-stigmast-5-ene-3B-ol (167), berberin cation (168). In addition another (supposedly new) parotoberberine base of molecular weight 366.1391, molecular formula (c2H2cNO5) has been isolated. Its structure however remain to be elucidated the proposed structure is (163). For elucidation of structures modern spectroscopic techniques, including one and two-dimensional NMR studies such as COSY, long-rang hetero-COSY, HOHAHA, 2DJ-resolved, COLOC, INADEQUATE and GASPE experiments were carrid out. X-ray crystallographic studies were performed in the case of caryophyllene-a-oxide (82). Some of the newly isolated compounds have shown some interesting biological activity (see results and discussion). In addition to this we have also investigated the chemical constituent of ficus bangolansus, which resulted in epifriendinyl-3-ol (169).

Item Type:Thesis (PhD)
Uncontrolled Keywords:sphaeranthus indicus, berberis parkeriana, terpenes, terpenoids, biosynthesis, sesquiterpenes, triterpenes, steroids, antimicrobial activity, immunestimulating activity
Subjects:Social Sciences(g) > Education(g6)
ID Code:702
Deposited By:Mr. Muhammad Asif
Deposited On:27 Sep 2006
Last Modified:04 Oct 2007 21:02

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