This item is only available for download by members of the University of Illinois community. Students, faculty, and staff at the U of I may log in with your NetID and password to view the item. If you are trying to access an Illinois-restricted dissertation or thesis, you can request a copy through your library's Inter-Library Loan office or purchase a copy directly from ProQuest.
Permalink
https://hdl.handle.net/2142/67220
Description
Title
Constituents of Aplysina Fistularis
Author(s)
Goo, Yang Mo
Issue Date
1979
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
Language
eng
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.
Use this login method if you
don't
have an
@illinois.edu
email address.
(Oops, I do have one)
IDEALS migrated to a new platform on June 23, 2022. If you created
your account prior to this date, you will have to reset your password
using the forgot-password link below.
