Scholarly
    Communications Project


Document Type:Dissertation
Name:Chongming Wu
Email address:wcming@vt.edu
URN:1998/00949
Title:Structural and Synthetic Studies of Potential Antitumor Natural Products
Degree:Doctor of Philosophy
Department:Chemistry
Committee Chair: David G. I. Kingston
Chair's email:Dkingston@chemserver.chem.vt.edu
Committee Members:Michael Calter
Neal Castagnoli
Harry C. Dorn
Richard Gandour
Keywords:natural products, antitumor, sesquiterpenoid, furanonaphthoquinone
Date of defense:August 13, 1998
Availability:Release the entire work for Virginia Tech access only.
After one year release worldwide only with written permission of the student and the advisory committee chair.

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.

List of Attached Files

Appendix.pdf Body.pdf Table.pdf
VITA.pdf

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