Type of Document Dissertation Author Wu, Chongming Jr. Author's Email Address email@example.com 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
Date of Defense 1998-08-13 Availability unrestricted AbstractBioassay 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.
Filename Size Approximate Download Time (Hours:Minutes:Seconds)
28.8 Modem 56K Modem ISDN (64 Kb) ISDN (128 Kb) Higher-speed Access Appendix.pdf 657.17 Kb 00:03:02 00:01:33 00:01:22 00:00:41 00:00:03 Body.pdf 728.07 Kb 00:03:22 00:01:44 00:01:31 00:00:45 00:00:03 Table.pdf 71.75 Kb 00:00:19 00:00:10 00:00:08 00:00:04 < 00:00:01 VITA.pdf 34.00 Kb 00:00:09 00:00:04 00:00:04 00:00:02 < 00:00:01
If you have questions or technical problems, please Contact DLA.