Investigation of the Natural Products Chemistry of the Fungus Phoma herbarum westend 1852

Show simple item record

dc.contributor.advisor Copp, B en
dc.contributor.author Gordon, Hugo en
dc.date.accessioned 2019-10-08T02:50:23Z en
dc.date.issued 2019 en
dc.identifier.uri http://hdl.handle.net/2292/48424 en
dc.description Full Text is available to authenticated members of The University of Auckland only. en
dc.description.abstract Fungal natural products have been used for spiritual and medicinal purposes through history and have given the world answers to some of the most pressing medical issues of our time. With more than 5 million species of fungi spanning the globe and inhabiting most niches, fungi have become an invaluable source of bioactive natural products. From Phoma herbarum westend 1852, a rust fungus that infects grasses and pasture legumes; six natural products were isolated. Fractionation of crude extract using a standard extraction procedure led to the isolation of two α-pyrones; taiwapyrone and xylariolide D, two furanones; (2Z)-cillifuranone and (2E)-cillifuranone, one acetamide; N-(5-hydroxypentyl) acetamide, and one anthraquinone; pachybasin. None of the natural products isolated showed significant activity against a variety of human pathogens. The total synthesis of xylariolide D was attempted, however progress came to a halt when dehydrogenation of the α-pyrone ring failed. (2Z)-Cillifuranone was postulated to exist as it is a critical moiety in another class of larger natural products; the sorbifuranones. Previous studies have isolated both (2E)-cillifuranone and sorbifuranone A -C in the same extract, therefore it was postulated that (2Z)-cillifuranone must exist under fungal conditions. A time-controlled experiment was conducted, and it was shown that in ambient temperature and light (2Z)-cillifuranone spontaneously isomerises to (2E)-cillifuranone. Interestingly the proposed biosynthesis of (2Z)-cillifuranone can double as a proposed biosynthesis for taiwapyrone if an alternative ring closure process occurs. A 1-13C acetate labelled experiment to determine the biosynthesises of these natural products was performed. It was shown that pachybasin is biosynthesised via cyclisation of an octaketide, biosynthesised from the acetate polyketide pathway. Literature values for pachybasin were found to be incorrect and were corrected using extensive 1D/ 2D NMR and a1-13C acetate labelled experiment. en
dc.publisher ResearchSpace@Auckland en
dc.relation.ispartof Masters Thesis - University of Auckland en
dc.relation.isreferencedby UoA99265182113302091 en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. en
dc.rights Restricted Item. Full Text is available to authenticated members of The University of Auckland only. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.rights.uri http://creativecommons.org/licenses/by-nc-sa/3.0/nz/ en
dc.title Investigation of the Natural Products Chemistry of the Fungus Phoma herbarum westend 1852 en
dc.type Thesis en
thesis.degree.discipline Chemistry en
thesis.degree.grantor The University of Auckland en
thesis.degree.level Masters en
dc.rights.holder Copyright: The author en
pubs.elements-id 783666 en
pubs.record-created-at-source-date 2019-10-08 en


Files in this item

Find Full text

This item appears in the following Collection(s)

Show simple item record

Share

Search ResearchSpace


Browse

Statistics