Date of Award
Fall 2007
Document Type
Thesis - Restricted
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
Donaldson, William A,
Abstract
Amphidinol 1, a bioactive compound, was isolated from a dinoflagellate in 1991. The compound (AMI) shows greater antifungal activity against Aspergillus niger than the pharmaceutical agent amphotericin B and also exhibits hemolytic activity. Other compounds in the amphidinol series exhibit these activities while the amphidinols increase cellular permeability. It was found that AM3 didn't destroy the cell membrane. The atom connectivity of the AMs have been published by several groups. However, AM3 is the only member, which was fully identified in terms of relative · stereochemistry and absolute configuration. Interestingly, the structurally similar luteophanols do not show bioactivity against the fungus. The unique structure of AMs consist of polyhydroxyl groups, two tetrahydropyan rings and a conjugated triene. Recently, amphidinol 7 (AM7) has been isolated and studied. This compound shows less bioactivity for Asp ergillus niger compared to AM3. The polyene side chain and two oxane rings present in AM7 are also contained in other AMs, however AM7 has a shorter polyol side chain than AM3. The relative stereochemistry of this polyol segment of AM7 has not detem1ined. Model compounds will be prepared to elucidate the structure of the polyol chain.
Recommended Citation
Chung, Seung Won, "Synthetic Studies Directed Toward the Marine Derived Amphidinol Natural Products C(5)-C(14), C(56), and C(57) Segments of AM7" (2007). Master's Theses (1922-2009) Access restricted to Marquette Campus. 5538.
https://epublications.marquette.edu/theses/5538