Type of Document Master's Thesis Author Williams, Russell Brian URN etd-11182002-213441 Title Isolation and Structure Elucidation of Cytotoxic Natural Products from Suriname and Madagascar Degree Master of Science Department Chemistry Advisory Committee
Advisor Name Title Kingston, David G. I. Committee Chair Gandour, Richard D. Committee Member Taylor, Larry T. Committee Member Keywords
- Polyprenylated Benzophenone
- Guttiferone G
- Garcinia macrophylla
- Natural products
- Bridelia tulasneana
Date of Defense 2002-09-30 Availability mixed AbstractThrough a continuing search for anticancer compounds as part of an International
Cooperative Biodiversity Grant program, the extracts of two plants were selected for study
on the basis of their cytotoxic activity. These extracts were further fractionated to yield
four compounds. The structures of these compounds were elucidated with mass
spectrometry and 1-D and 2-D NMR spectroscopy.
The ethyl acetate extract of the twigs of Garcinia macrophylla from Suriname was
weakly cytotoxic in the A2780 human ovarian cancer cell bioassay. The known
benzophenone guttiferone A and a new guttiferone analog, named guttiferone G, were
isolated from the extract and found to be responsible for the bioactivity. A known
triterpene, friedelin, was also isolated from the extract and found to be inactive. The
structure of guttiferone A was determined by comparison of its NMR data to those found in
the literature. The structure of guttiferone G was determined by comparison to guttiferone
A and through careful examination of both 1D and 2D NMR data.
An extract of Bridelia tulasneana from Madagascar yielded one compound. It was
identified as the known lignan deoxypodophyllotoxin and was responsible for the
bioactivity. It was identified by a comparison of its spectral data to those found in the
literature and those of an authentic sample.
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