Fungal Triterpenes

Adam, Hugh Kane (1967) Fungal Triterpenes. PhD thesis, University of Glasgow.

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Abstract

Structural studies on the methyl esters of the triterpene acids from the polypore Daedalea quercina have established the structure of the major component, methyl carbomethoxyacetyl-. quercinate. In common with this compound, three other esters from this fungus are 23-keto-27-carboxylic esters. The first and second of these are methyl 16-hydroxycarbomethoxyacetylquercinate and methyl 16-hydroxyquercinate respectively. The third ester, methyl carbomethoxyacetyldaedaleate, which is the first recorded triterpene based on a skeleton, is highly reactive and has not, as yet, yielded recognisable transformation products. The structure advanced for this compound is based on spectroscopic examination. A minor constituent of Daedalea quercina is thought to be methyl 25-hydroxypolyporenate C. The synthesis and properties of carbomethoxyacetyl and carboxyacetyl derivatives of triterpenes have been studied. Examination of the methyl esters of the triterpene acids from Leptoporus stipticus has established that the major component, methyl tyromycate, is methyl 3-oxolanosta-7,9(11),24-trien-26-oate. Four other compounds from this fungus have been studied. Three of these have been shown to be triterpene glucosides, the first from a fungal source, whose basic nuclei are similar to that of methyl tyromycate. The last ester from Leptoporus stipticus, methyl leptoporate, is the second example of a C32 triterpene. Leptoporus stipticus (Pers.) Quel. , when cultured on malt agar medium, produces eburicoic acid and tumulosic acid. Attempts to influence the metabolite production of this latter fungus are described.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1967
Depositing User: Enlighten Team
Unique ID: glathesis:1967-78438
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 28 Feb 2020 12:09
Last Modified: 28 Feb 2020 12:09
URI: http://theses.gla.ac.uk/id/eprint/78438

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