{"id":{"repo_id":"temple","oai_identifier":"oai:scholarshare.temple.edu:20.500.12613/7731"},"canonical_url":"https://search.dev.ndltd.org/etd/temple/oai:scholarshare.temple.edu:20.500.12613/7731","repository":{"repo_id":"temple","name":"Temple University","base_url":"https://scholarshare.temple.edu/server/oai/request"},"display":{"title":"Semi-Synthesis of Melodinine, Taberyunine, and Melosuavine Bis-Indole Alkaloids Through Chemical and Biological Methods","abstract":"The first semi-synthesis of (-)-melodinine K was completed from the monoterpene indole alkaloid (-)-tabersonine through regioselective enzymatic hydroxylation and Polonovski-Potier coupling. Regioselective borylation strategies were used to achieve meta-oxygenated derivatives of (-)-tabersonine for analysis in a Drosophila fruit fly Alzheimer’s phenotype model. A library of oxygenated and epoxidized bis-indole alkaloid analogs in the taberyunine class were prepared to conduct a structure activity relationship (SAR) study of the bis-indole framework against colon cancer and melanoma cell lines. Alkaloid aryl trifluoroborates were synthesized to increase nucleophilicity of arenes for unfavored alpha-arylations of tertiary amines on route to melosuavine bis-indole alkaloids. Overall, nine new bis-indole alkaloids were synthesized in the melodinine, taberyunine, and melosuavine class that showed strong cytotoxicity against a variety of melanoma, colon cancer, and renal cancer cell lines.","abstract_html":"The first semi-synthesis of (-)-melodinine K was completed from the monoterpene indole alkaloid (-)-tabersonine through regioselective enzymatic hydroxylation and Polonovski-Potier coupling. Regioselective borylation strategies were used to achieve meta-oxygenated derivatives of (-)-tabersonine for analysis in a Drosophila fruit fly Alzheimer’s phenotype model. A library of oxygenated and epoxidized bis-indole alkaloid analogs in the taberyunine class were prepared to conduct a structure activity relationship (SAR) study of the bis-indole framework against colon cancer and melanoma cell lines. Alkaloid aryl trifluoroborates were synthesized to increase nucleophilicity of arenes for unfavored alpha-arylations of tertiary amines on route to melosuavine bis-indole alkaloids. Overall, nine new bis-indole alkaloids were synthesized in the melodinine, taberyunine, and melosuavine class that showed strong cytotoxicity against a variety of melanoma, colon cancer, and renal cancer cell lines.","abstract_has_math":false,"creators":["Gardner, Alexander Charles"],"institution":"Temple University. Libraries","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Davis, Franklin A.","Andrade, Rodrigo B."],"committee_chairs":[],"committee_members":["Wengryniuk, Sarah E.","Sieburth, Scott McNeill","Cannon, Kevin C."],"year":2022,"date_issued":"2022","date_published":"2022","updated_at":"2026-07-27T21:19:39Z","subjects":["Organic chemistry","Alkaloids","Biotransformation","Bis-indole","Melodinine K","Natural products","Tabersonine"],"languages":["eng"],"rights":["IN COPYRIGHT- This Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available."],"rights_urls":["http://rightsstatements.org/vocab/InC/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/20.500.12613/7731","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Davis, Franklin A.","Andrade, Rodrigo B."]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["Wengryniuk, Sarah E.","Sieburth, Scott McNeill","Cannon, Kevin C."]},{"key":"dc:creator","label":"Author","values":["Gardner, Alexander Charles"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2022-05-26T18:18:43Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2022-05-26T18:18:43Z"]},{"key":"dc:date.issued","label":"Date","values":["2022"]},{"key":"dc:publisher","label":"Institution","values":["Temple University. 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Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available."]},{"key":"dc:rights.uri","label":"Rights URI","values":["http://rightsstatements.org/vocab/InC/1.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/20.500.12613/7731"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The first semi-synthesis of (-)-melodinine K was completed from the monoterpene indole alkaloid (-)-tabersonine through regioselective enzymatic hydroxylation and Polonovski-Potier coupling. Regioselective borylation strategies were used to achieve meta-oxygenated derivatives of (-)-tabersonine for analysis in a Drosophila fruit fly Alzheimer’s phenotype model. A library of oxygenated and epoxidized bis-indole alkaloid analogs in the taberyunine class were prepared to conduct a structure activity relationship (SAR) study of the bis-indole framework against colon cancer and melanoma cell lines. Alkaloid aryl trifluoroborates were synthesized to increase nucleophilicity of arenes for unfavored alpha-arylations of tertiary amines on route to melosuavine bis-indole alkaloids. Overall, nine new bis-indole alkaloids were synthesized in the melodinine, taberyunine, and melosuavine class that showed strong cytotoxicity against a variety of melanoma, colon cancer, and renal cancer cell lines."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["Ph.D."]},{"key":"dc:title","label":"Title","values":["Semi-Synthesis of Melodinine, Taberyunine, and Melosuavine Bis-Indole Alkaloids Through Chemical and Biological Methods"]}]}],"canonical_facts":{"dc:contributor.advisor":["Davis, Franklin A.","Andrade, Rodrigo B."],"dc:contributor.committeemember":["Wengryniuk, Sarah E.","Sieburth, Scott McNeill","Cannon, Kevin C."],"dc:creator":["Gardner, Alexander Charles"],"dc:date.accessioned":["2022-05-26T18:18:43Z"],"dc:date.available":["2022-05-26T18:18:43Z"],"dc:date.issued":["2022"],"dc:description.abstract":["The first semi-synthesis of (-)-melodinine K was completed from the monoterpene indole alkaloid (-)-tabersonine through regioselective enzymatic hydroxylation and Polonovski-Potier coupling. Regioselective borylation strategies were used to achieve meta-oxygenated derivatives of (-)-tabersonine for analysis in a Drosophila fruit fly Alzheimer’s phenotype model. A library of oxygenated and epoxidized bis-indole alkaloid analogs in the taberyunine class were prepared to conduct a structure activity relationship (SAR) study of the bis-indole framework against colon cancer and melanoma cell lines. Alkaloid aryl trifluoroborates were synthesized to increase nucleophilicity of arenes for unfavored alpha-arylations of tertiary amines on route to melosuavine bis-indole alkaloids. Overall, nine new bis-indole alkaloids were synthesized in the melodinine, taberyunine, and melosuavine class that showed strong cytotoxicity against a variety of melanoma, colon cancer, and renal cancer cell lines."],"dc:description.degree":["Ph.D."],"dc:identifier.uri":["http://hdl.handle.net/20.500.12613/7731"],"dc:language.iso":["eng"],"dc:publisher":["Temple University. Libraries"],"dc:rights":["IN COPYRIGHT- This Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available."],"dc:rights.uri":["http://rightsstatements.org/vocab/InC/1.0/"],"dc:subject":["Organic chemistry","Alkaloids","Biotransformation","Bis-indole","Melodinine K","Natural products","Tabersonine"],"dc:title":["Semi-Synthesis of Melodinine, Taberyunine, and Melosuavine Bis-Indole Alkaloids Through Chemical and Biological Methods"],"dc:type":["Text"]},"updated_at":"2026-07-27T21:19:39Z"}