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Goo, Yang Mo 2014-12-13T20:10:53Z 2014-12-13T20:10:53Z 10000-01-01 1979 1979 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. Made available in DSpace on 2014-12-13T20:10:53Z (GMT). No. of bitstreams: 1 8017944.pdf: 14096719 bytes, checksum: 74b53de07e7103e066a624735386ee3b (MD5) Previous issue date: 1979 Embargo set by: Seth Robbins for item 67398 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 533 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1979. http://hdl.handle.net/2142/67220 (UMI)AAI8017944 eng Chemistry, Organic Constituents of Aplysina Fistularis text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.