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ISOLATION, CHARACTERIZATION OF BIOACTIVE NATURAL PRODUCTS FROM TANACETUM ARTEMISIOIDES EUPHORBIA DECIEPIENS AND RANUNCULUS LAETUS

Hussain, Javid (2004) ISOLATION, CHARACTERIZATION OF BIOACTIVE NATURAL PRODUCTS FROM TANACETUM ARTEMISIOIDES EUPHORBIA DECIEPIENS AND RANUNCULUS LAETUS. PhD thesis, University of Karachi, Karachi.

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Abstract

The Ph. D. dissertation in hand is based on research work carried out on phytochemical and biological studies on Euphorbia decipiens Part-A, Tanacetum artemisioides Part-B, Ranunculus leatus Part-C, Synthesis and characterizations of Organotin Complexes Part-D Part-A, the work on Iranian plant Euphorbia decipiens led to the isolation of five new myrsinol diterpenoids. 3,5,13,17-tetra-O-acetyl-7-O-benzoyl-15-hydroxymyrsinol(50), 3,5,15,17-tetra-O-acetyl-7-O-butanoyl-13-hydroxymyrsinol(51), 7,15-di-O-acetyl-3-O-butanoyl-5-O-benzoyl-13, 14-dihydroxoymyrsinol (52), 3,7,15-tri-O-acetyl-5-O-niootinoyl-13,14-dihydroxy-myrsinol (53), and 5,7,17-tri-O-acetyl-3-O-benzoyl-15-hydroxycheiradone (54). The first two compounds (50) and (51) are tricyclic diterpenoids, while remaining three (52), (53) and (54) are tetracyclic diterpenoids. Compounds 7,15-di-O-acetyl-3-O-nicotinoyl-13, 14-dihydroxymyrsinol (53) contain hemiacetal ring between C-17 and C-15 while, compounds 5,7,17-tri-O-acetyl-3-O-benzoyl-15-hydroxycheiradone (54) contains another ring as a tetrahydrofuranmoiety due to epoxy bridge between C-10 and C-13 where as a known compound 3,7,17-tri-O-acetyl-5-O-butanoyl-13, 15-dihydroxymyrsinol (55) has also been isolated Compounds 50, 51 and 52 exhibited inhibitory activity against urease enzyme while compounds 53 and 54, exhibited inhibitory activity against prolyl endopeptidase enzyme New compounds from Euphorbia decipiens 1. 3,5,13,17-tetra-O-acetyl-7-O-benzoyl-15-hydroxymyrsinol (50) 2. 3,5,15,17-tetra-O-acetyl-7-O-butanoyl-13-hydroxymyrsinol (51) 3. 7,15-Di-O-acetyl-3-O-butanoyl-5-O-benzoyl-13,14-dihydrixoymyrsinol (52) 4. 3,7,15-Tri-O-acetyl-5-O-nicotinoyl-13,14-dihydroxymyrsinol (53) 5. 5,7,17-Tri-O-acetyl-3-O-benzoyl-15-hydroxycheiradone (54) Known compound 6. 3,7,17-Tri-O-acetyl-5-O-butanoyl-13,15-dihydroxymyrsinol (55) Part-B, Phytochemical investigation on Tanacetum artemisioides, resulted in the isolation and characterization of three new ceramides i.e. tanacetamide A (15), tanacetamide B (16) and tanacetamide C (17), along with seven known compounds i.e. stigmasterol (18), stigmasterol 3-O-B-D-glucoside (19), 5,4-dihydroxy-3,6,7-trimethoxyflavone (20) 5-hydroxy-3,6,7,4-tetramethoxyflavone (21) oleanolic acid (22) B-sitosterol (23) and leukodin (24). Compound (15) and (16) exhibited inhibitory activity against acetyl cholinesterase enzyme New Compounds from Tanacetum artemisioides 1. Tanacetamide A. 2. Tanacetamide B. 3. Tanacetamide C. Part-C, Phytochemical investigation on whole plant Ranunculus laetus resulted in the isolation and characterization of six known compounds for the first time from this source namely 6,7-dimethoxycoumarin (1), B-sitosterol 3-O-B-D-glucoside (2), Jacedin 5-O-B-D-glucoside (4), Centaurein (5), and B-amyrin (6) Part-D, Synthesis of organotin (IV) complexes culminated in two series of complexes including triorganotin (IV) and diorganotin (IV) complexes of the general formula R4-nSnLn (where R = Ch3 C4H9, C6H5, n = 1,2 and HL are different carboxylate ligands) which were prepared by reacting glutaric anhydride with different alcohols have been synthesized by the reaction of caroxylate ligands and different organotin halides in 1:1 and 2:1 (ligand : metal) molar ratio respectively. All of the compounds have been characterized by IR, UV, 1H-NMR, 13C-NMR and mass spectrometry. Diorganotin (IV) compounds are Dimethyltine (IV) bis mono-n-propyl glutarate, dimethyltin (IV) bis monomethyl glutarate, dibutyltin (IV) bis monoisopropyl glutarate, dibutyltin (IV) bis mono n-propyl glutarate and dibutyltin (IV) bis monomethyl glutarate. The triorganotin (IV) complexes are triphenyltin (IV) Monomethyl glutarate and triphenyltin (IV) Mono n-propyl glutarate

Item Type:Thesis (PhD)
Uncontrolled Keywords:euphorbia decipiens, tanacetum artemisioides, ranunculus leatus, organotin complexes, urease enzyme, diterpenoids, myrisinol diterpenoids, prolyl endopeptidase
Subjects:Physical Sciences (f) > Chemistry(f2)
ID Code:1325
Deposited By:Mr. Muhammad Asif
Deposited On:27 Jan 2007
Last Modified:04 Oct 2007 21:05

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