Total Synthesis and the Biological Activities of (±)-Norannuradhapurine

The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aure...

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Autores principales: Nimgirawath, Surachai, Lorpitthaya, Rujee, Wanbanjob, Asawin, Taechowisan, Thongchai, Shen, Yue-Mao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2008
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6253887/
https://www.ncbi.nlm.nih.gov/pubmed/19127240
http://dx.doi.org/10.3390/molecules14010089
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author Nimgirawath, Surachai
Lorpitthaya, Rujee
Wanbanjob, Asawin
Taechowisan, Thongchai
Shen, Yue-Mao
author_facet Nimgirawath, Surachai
Lorpitthaya, Rujee
Wanbanjob, Asawin
Taechowisan, Thongchai
Shen, Yue-Mao
author_sort Nimgirawath, Surachai
collection PubMed
description The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (±)-norannuradhapurine inhibits the production of NO, PGE(2), TNF-a, IL-1b and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro.
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spelling pubmed-62538872018-11-30 Total Synthesis and the Biological Activities of (±)-Norannuradhapurine Nimgirawath, Surachai Lorpitthaya, Rujee Wanbanjob, Asawin Taechowisan, Thongchai Shen, Yue-Mao Molecules Article The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (±)-norannuradhapurine inhibits the production of NO, PGE(2), TNF-a, IL-1b and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro. Molecular Diversity Preservation International 2008-12-29 /pmc/articles/PMC6253887/ /pubmed/19127240 http://dx.doi.org/10.3390/molecules14010089 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Nimgirawath, Surachai
Lorpitthaya, Rujee
Wanbanjob, Asawin
Taechowisan, Thongchai
Shen, Yue-Mao
Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
title Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
title_full Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
title_fullStr Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
title_full_unstemmed Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
title_short Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
title_sort total synthesis and the biological activities of (±)-norannuradhapurine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6253887/
https://www.ncbi.nlm.nih.gov/pubmed/19127240
http://dx.doi.org/10.3390/molecules14010089
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