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• W43330981 abstract "This thesis discusses chemical aspects of the problems relating to a small tree. Terminalia oblongata which grows over a large area of Central Western Queensland and which is toxic to sheep and cattle.The discovery that the toxin which produces Terminalia oblongata poisoning or McKenzie River Disease is extracted from the plant by water, and tests and procedures which demonstrate that polyphenolic compounds and tannins constitute the bulk of the aqueous extract are discussed.Current knowledge of the chemistry of the type of hydrolysable tannins which have been found in plants of the Terminalia species is summarized, as is the evidence available in the literature concerning the toxicity of the tannins and their hydrolysis products.. Similarity between poisoning of cattle by Terminalia oblongata and poisoning of cattle by oak (Quercus havardi) in the United States are discussed, since oak poisoning has been attributed to tannins.Studies on toxic aqueous extracts from Terminalia oblongata are reported. The isolation and characterization of gallic acid (3,4,5-trihydroxybenzoic acid) and ellagic acid (2,3,7,8-tetrahydroxy[1]benzopyrano[5,4,3-cde] benzopyran-5,10-dione) which are both known compounds is discussed. Partial elucidation of the structure of the major tannin of the toxic aqueous extract, an ellagitannin which has been assigned the letter symbol A, is considered. It is shown that on acid or base hydrolysis ellagitannin A gives four important products - gallic acid, ellagic acid, glucose and a polyphenolic molecule J which has been identified as a dimer of ellagic acid, involving a C-C link between aromatic rings on two ellagic acid molecules. Derivatives of J have been prepared, isolated and studied with the aid of a variety of techniques, as have the molecules in which J is still associated with the glucose molecule. It has been shown that in the ellagitannin the two lactone rings of one of the ellagic acid molecules are open and the two acid groups which result are esterified to glucose, probably at positions 3 and 6. The second ellagic acid molecule which goes to make up the dimer is intact and forms a side chain.It is suggested, but not proven, that the remainder of the tannin structure consists of gallic acid esterified at position 1 and 4,5,6,4’,5',6'-hexahydroxybiphenyl-2,2'-dicarboxylic acid esterified across positions 2 and 4 of glucose. This molecule is the source of the ellagic acid which is one of the hydrolysis products.Aspects of the metabolism of the polyphenols in the animal body are introduced as is discussion of the relationship between the polyphenols of the leaves and those of the fruit and bark of Terminalia oblongata. Similarities between the polyphenols of the leaves of Terminalia oblongata and of Terminalia porphyrocarpa, another native Central Queensland tree which has caused deaths of livestock, are considered." @default.
• W43330981 created "2016-06-24" @default.
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• W43330981 date "1975-01-01" @default.
• W43330981 modified "2023-09-27" @default.
• W43330981 title "Chemical studies on Terminalia oblongata" @default.
• W43330981 hasPublicationYear "1975" @default.
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