Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one

The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the a...

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Autores principales: Nimgirawath, Surachai, Udomputtimekakul, Phansuang, Pongphuttichai, Samathi, Wanbanjob, Asawin, Taechowisan, Thongchai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2008
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245467/
https://www.ncbi.nlm.nih.gov/pubmed/19043347
http://dx.doi.org/10.3390/molecules13122935
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author Nimgirawath, Surachai
Udomputtimekakul, Phansuang
Pongphuttichai, Samathi
Wanbanjob, Asawin
Taechowisan, Thongchai
author_facet Nimgirawath, Surachai
Udomputtimekakul, Phansuang
Pongphuttichai, Samathi
Wanbanjob, Asawin
Taechowisan, Thongchai
author_sort Nimgirawath, Surachai
collection PubMed
description The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.
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spelling pubmed-62454672018-11-26 Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one Nimgirawath, Surachai Udomputtimekakul, Phansuang Pongphuttichai, Samathi Wanbanjob, Asawin Taechowisan, Thongchai Molecules Article The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028. MDPI 2008-11-28 /pmc/articles/PMC6245467/ /pubmed/19043347 http://dx.doi.org/10.3390/molecules13122935 Text en © 2008 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
Udomputtimekakul, Phansuang
Pongphuttichai, Samathi
Wanbanjob, Asawin
Taechowisan, Thongchai
Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
title Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
title_full Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
title_fullStr Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
title_full_unstemmed Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
title_short Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
title_sort total synthesis and antimicrobial activity of (±)-laurelliptinhexadecan-1-one and (±)-laurelliptinoctadecan-1-one
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245467/
https://www.ncbi.nlm.nih.gov/pubmed/19043347
http://dx.doi.org/10.3390/molecules13122935
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