Title page for ETD etd-72198-18137


Type of Document Dissertation
Author Wu, Chongming Jr.
Author's Email Address wcming@vt.edu
URN etd-72198-18137
Title Structural and Synthetic Studies of Potential Antitumor Natural Products
Degree PhD
Department Chemistry
Advisory Committee
Advisor Name Title
Kingston, David G. I. Committee Chair
Calter, Michael A. Committee Member
Castagnoli, Neal Jr. Committee Member
Dorn, Harry C. Committee Member
Gandour, Richard D. Committee Member
Keywords
  • natural products
  • antitumor
  • sesquiterpenoid
  • furanonaphthoquinone
Date of Defense 1998-08-13
Availability unrestricted
Abstract
Bioassay directed fractionation of the methyl ethyl ketone extract of Chiloscyphus rivularis yielded eight sesquiterpenoids, and detailed spectroscopic interpretation led to the assignment of their structures as 12-hydroxychiloscyphone, chiloscypha-2,7-dione, 12-hydroxychiloscypha-2,7-dione, chiloscypha-2,7,9-trione, rivulalactone, 4-hydroxy oppositant-7-one, chiloscyphone, and intermedeol. The structure and stereochemistry of rivulalactone, a novel trinorsesquiterpenoid, was confirmed by its synthesis starting from chiloscyphone. 12-Hydroxychiloscyphone, chiloscypha-2,7-dione, 12-hydroxychiloscypha-2,7-dione, chiloscypha-2,7,9-trione, rivulalactone are new. 12-Hydroxychiloscyphone showed selective bioactivity towards DNA repair-deficient yeast mutants and cytotoxicity to human lung carcinoma cells.

In order to improve the activity of cytotoxic furanonaphthoquinones by affixing a hydroxyamino side chain, 2-methyl-2-[2'-(4',9'-dihydronaphtho[2',3'-b]furan-4',9'-dionyl methyl)amino]-1,3-propanediol and its analogs have been synthesized. Bioassay data showed they act by a different mechanism of action than their parental furanonaphthoquinone derivatives.

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