Biologically Active Compounds From Caribbean Sponges
Phillipson, Douglas Wayne
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https://hdl.handle.net/2142/70294
Description
Title
Biologically Active Compounds From Caribbean Sponges
Author(s)
Phillipson, Douglas Wayne
Issue Date
1985
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
The isolation and structure elucidation of a number of 1,2-dioxolane and 1,2 dioxane acids and esters from two caribbean sponges is described. Interest in these compounds was motivated by the acid's pharmacological activities when tested in vitro against various gram positive bacteria, yeasts and fungi. The corresponding esters were relatively inactive as antibacterial agents but because they were more stable and easier to purify, they were the compounds chosen for the structural studies. Structure elucidation of the purified esters was based on interpretation of the compounds high resolution nuclear magnetic resonance and mass spectra. Confirmation of some of the structures was accomplished by an ozonolysis degradation sequence and formation of a lactone from the ester carbonyl and one of the peroxide oxygens and spectroscopic characterization of the derivatives.
The carboxylic acids were difficult to purify in the quantities needed for complete biological testing and the peroxides were unstable on standing and very sensitive to alkali, therefore conversion of the esters to the acids using the usual hydrolytic conditions failed. In order to avoid these problems while obtaining the quantities needed for in vitro testing, the six membered ring peroxides were converted to their acids by reduction of the ester to an alcohol followed by oxidation to the acid. The five membered ring peroxides were unstable to all attempts at reduction and were not fully tested for biological activity.
A rapid isolation of (+) aeroplysinin-I from Aplysina archeri is also described. In addition the literature on recent developments in marine sources of brominated tyrosine metabolites as well as a complete review of all the marine 1,2 dioxanes of non-sterol biosynthetic origin is discussed. We believe that the present report of 1,2 dioxolanes is the first report of such compounds from a marine source. As is often the case, we cannot be sure that these compounds are true sponge metabolites and not products of a simboiant.
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