Title page for ETD etd-11182002-213441

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
  • Polyprenylated Benzophenone
  • Guttiferone G
  • Garcinia macrophylla
  • Natural products
  • Deoxypodophyllotoxin
  • Bridelia tulasneana
  • Garcinia
  • Bridelia
Date of Defense 2002-09-30
Availability mixed
Through 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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  Appendix.pdf 511.37 Kb 00:02:22 00:01:13 00:01:03 00:00:31 00:00:02
  Chapter1.pdf 296.31 Kb 00:01:22 00:00:42 00:00:37 00:00:18 00:00:01
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  TableofContents.pdf 124.51 Kb 00:00:34 00:00:17 00:00:15 00:00:07 < 00:00:01
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  Vita.pdf 45.84 Kb 00:00:12 00:00:06 00:00:05 00:00:02 < 00:00:01
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