{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/70347"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/70347","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Part 1. Biologically Active Compounds From Agelas Sponges. Part 2. Barnacle Settlement Inhibitors From Octocorallia (Antifouling, Antibacterial, Renillafoulins, Antiviral, Caribbean)","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Keifer, Paul Allen"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-15T23:18:50Z","date_published":"2014-12-15T23:18:50Z","updated_at":"2026-07-22T22:26:02Z","subjects":["Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8701527"],"render_values":[{"text":"(UMI)AAI8701527","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/70347","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Keifer, Paul Allen"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-15T23:18:50Z","10000-01-01","1986"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/70347","(UMI)AAI8701527"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["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.","Made available in DSpace on 2014-12-15T23:18:50Z (GMT). No. of bitstreams: 1 8701527.pdf: 6873371 bytes, checksum: 0a31ce880bd72f87c4b8fbd1682277be (MD5) Previous issue date: 1986","Embargo set by: Seth Robbins for item 70513 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","255 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1986."]},{"key":"dc:title","label":"Title","values":["Part 1. Biologically Active Compounds From Agelas Sponges. Part 2. Barnacle Settlement Inhibitors From Octocorallia (Antifouling, Antibacterial, Renillafoulins, Antiviral, Caribbean)"]}]}],"canonical_facts":{"dc:creator":["Keifer, Paul Allen"],"dc:date":["2014-12-15T23:18:50Z","10000-01-01","1986"],"dc:description":["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.","Made available in DSpace on 2014-12-15T23:18:50Z (GMT). No. of bitstreams: 1 8701527.pdf: 6873371 bytes, checksum: 0a31ce880bd72f87c4b8fbd1682277be (MD5) Previous issue date: 1986","Embargo set by: Seth Robbins for item 70513 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","255 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1986."],"dc:identifier":["http://hdl.handle.net/2142/70347","(UMI)AAI8701527"],"dc:subject":["Chemistry, Organic"],"dc:title":["Part 1. Biologically Active Compounds From Agelas Sponges. Part 2. Barnacle Settlement Inhibitors From Octocorallia (Antifouling, Antibacterial, Renillafoulins, Antiviral, Caribbean)"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:02Z"}