Part 1. Biologically Active Compounds From Agelas Sponges. Part 2. Barnacle Settlement Inhibitors From Octocorallia (Antifouling, Antibacterial, Renillafoulins, Antiviral, Caribbean)
Keifer, Paul Allen
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Permalink
https://hdl.handle.net/2142/70347
Description
Title
Part 1. Biologically Active Compounds From Agelas Sponges. Part 2. Barnacle Settlement Inhibitors From Octocorallia (Antifouling, Antibacterial, Renillafoulins, Antiviral, Caribbean)
Author(s)
Keifer, Paul Allen
Issue Date
1986
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
Biologically active extracts of the Caribbean sponges Agelas coniferin and Agelas cf. mauritiana have been found to contain seven new bromopyrroles (1a, 3a-8a), as well as the known debromooroidin-dimer sceptrin (2a). These compounds, isolated as the diacetate salts, were found to be antibacterial and antiviral, and were active in barnacle settlement and biochemical prophage induction assays. The structures, with tentative stereochemistries, were based on spectroscopic comparisons to sceptrin (2a) and two-dimensional NMR data.
Systematic gradient high pressure liquid chromatography (HPLC) of sixty-five different Agelas sponge extracts were performed using compounds 1a-8a as chromatographic standards. The composition of each crude extract was correlated with its biological activity as determined by a battery of qualitative and quantitative bioassays. The application of this technique to chemotaxonomy is discussed.
Extracts of the sea pansy Renilla reniformis, which inhibit the settlement of barnacle larvae, have been found to contain three new diterpenes: renillafoulins A (1), B (2), and C (3). All three compounds inhibit barnacle settlement, with EC(,50) values ranging from 0.02 to 0.2 (mu)g/mL. The structures were elucidated using two-dimensional NMR data and spectroscopic comparisons to briarein-type diterpenes isolated from other Pennatulacea. Single crystal X-ray diffraction data for 3 confirmed the structure.
Other extracts with antifouling activity, obtained from Leptogorgia virgulata, were found to contain the known diterpenes pukalide (5) and 11(beta), 12(beta)-pukalide (6), as well as two other active metabolites. The oxidative decomposition products of 5 and 6 are discussed.
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