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Title:Constituents of Aplysina Fistularis
Author(s):Goo, Yang Mo
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:The constituents of three species of a marine sponge, Aplysina fistularis, were examined by gas chromatography/mass spectrometry (GC/MS), high pressure liquid chromatography (HPLC) and classical fractionation and purification procedures. GC/MS indicated that many brominated tyrosine metabolites were accumulated in two A. fistularis samples, #852 and #947. By employing this technique, brominated hydroquinones; brominated phenylacetonitriles; brominated phenylacetamides; aeroplysinins; brominated 2-hydroxy-4-methoxyphenylacetic acid lactones; 2,6-dibromo-4-hydroxy-2,5-cyclohexadienone-4-acetamide, its monobromo analog and its ketals; and brominated phenylacetic acids were identified in the extracts of samples #852 and #947.
HPLC study of sample #852 gave identified and allowed isolation of several brominated tyrosine metabolites. Antimicrobial activity of this sample was mostly due to aeroplysinin-1, 2,6-dibromo-4-hydroxy-2,5-cyclohexadienone-4-acetamide and the acetic acid analog of the latter.
Fractionation and purification of the extract of sample #947 on a large scale gave aerothionin as a major constituent. Attempts to isolate antimicrobial compounds in this extract were unsuccessful.
Purification of the antimicrobial principles of sample IBE-12-III-77-1-3 gave two major antimicrobial compounds (2,6-dibromo-4-hydroxy-2,5-cyclohexadienone-4-acetamide and 2,6-dibromo-4-hydroxy-2-cyclohexenone-4-acetamide-5N-lactam). The latter was previously unidentified natural product with strong, broad antimicrobial activity. Dichloro and bromochloro analogs of both compounds were also identified.
Issue Date:1979
Type:Text
Language:English
Description:533 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1979.
URI:http://hdl.handle.net/2142/67220
Other Identifier(s):(UMI)AAI8017944
Date Available in IDEALS:2014-12-13
Date Deposited:1979


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