Terpenoids from terrestrial and marine sources
department or school: Science, Faculty of
department or school: Chemistry, Department of
data provider: DSpace
degree campus: UBCV
creator: Hirkala-Schaefer, Truman
issued: 2021-04-30T07:00:00Z
issued: 2020
related degree: Master of Science - MSc
degree grantor: University of British Columbia
description: The prehistoric Australian conifer Wollemia nobilis was thought to be extinct until the discovery of living specimens in 1992. Due to its threatened status and restricted distribution, investigations into its metabolic constituents have been limited. Chapter 2 details the phytochemical investigation of Wollemia nobilis. Crude organic extracts from the leaves Wollemia nobilis collected on UBC campus were screened for bioactivity against a series of pathogens. Bioassay guided fractionation led to the isolation and structural elucidation of the novel compound 2.12, which upon examination of the experimental data was found to be the true structure of the previously reported compound wollemolide (2.11). Additionally, two new endoperoxide diterpenoids (2.14 & 2.15), several known compounds new to the Wollemia genus (2.13 & 2.16-2.18), as well as sandaracopimaric acid (2.4) previously reported from Wollemia nobilis were isolated and structurally elucidated. The pure compounds demonstrated no in vitro activity against the screened pathogens Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa, Candida albicans and methicillin resistant Staphylococcus aureus (MRSA). The Indonesian sponge Petrosia contignata has been the source of several novel bioactive metabolites. Though previously examined, the crude sponge extracts of Petrosia contignata were investigated for less abundant metabolites. Chapter 3 describes the isolation and structural elucidation of the new tetrahydroxylated steroid petrosiasterol (3.9). as well as three known steroids new to the Petrosia genus (3.7, 3.8, & 3.11) and one previously reported from the Petrosia genus (3.10).
aggregated CHO: https://circle.library.ubc.ca/rest/handle/2429/74187
note: Terpenoids from Terrestrial and Marine Sources by Truman Hirkala-Schaefer B.Sc., University of Victoria, 2015 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE in THE FACULTY OF GRADUATE AND POSTDOCTORAL STUDIES (Chemistry) THE UNIVERSITY OF BRITISH COLUMBIA (Vancouver) April 2020 © Truman Hirkala-Schaefer, 2020 ii The following individuals certify that they have read, and recommend to the Faculty of Graduate and Postdoctoral Studies for acceptance, the thesis entitled: Terpenoids from Terrestrial and Marine Sources submitted by Truman Hirkala-Schaefer in partial fulfillment of the requirements for the degree of Master of Science in Chemistry Examining Committee: Dr. Raymond J. Andersen, Professor, Chemistry, UBC Supervisor Dr. Katherine Ryan, Associate Professor, Chemistry, UBC Supervisory Committee Member Dr. Stephen Withers, Professor, Chemistry, UBC Supervisory Committee Member iii Abstract The prehistoric Australian conifer Wollemia nobilis was thought to be extinct until the discovery of living specimens in 1992. Due to its threatened status and restricted distribution, investigations into its metabolic constituents have been limited. Chapter 2 details the phytochemical investigation of Wollemia nobilis. Crude organic extracts from the leaves Wollemia nobilis collected on UBC campus were screened for bioactivity against a series of pathogens. Bioassay guided fractionation led to the isolation and structural elucidation of the novel compound 2.12, which upon examination of the experimental data was found to be the true structure of the previously reported compound wollemolide (2.11). Additionally, two new endoperoxide diterpenoids (2.14 & 2.15), several known compounds new to the Wollemia genus (2.13 & 2.16-2.18), as well as sandaracopimaric acid (2.4) previously reported from Wollemia nobilis were isolated and structurally elucidated. The pure compounds demonstrated no in vitro activity against the screened patho…
has type: Thesis/Dissertation
date issued: 2020-05
is shown at: 10.14288/1.0389990
language: eng
degree discipline: Chemistry
provider: Vancouver : University of British Columbia Library
publisher: University of British Columbia
rights: Attribution-NonCommercial-NoDerivatives 4.0 International
rights URI: http://creativecommons.org/licenses/by-nc-nd/4.0/
scholar level: Graduate
type: Text
identifier URI: http://hdl.handle.net/2429/74187