Files in this item
|(no description provided)|
|Title:||Constituents of Aplysina Fistularis|
|Author(s):||Goo, Yang Mo|
|Department / Program:||Chemistry|
|Degree Granting Institution:||University of Illinois at Urbana-Champaign|
|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.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1979.
|Date Available in IDEALS:||2014-12-13|