Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide

A novel stereoisomer of eushearilide, 23-demethyleushearilide, was synthesized, and the structure–activity relationships of this compound along with known eushearilide stereoisomers were investigated in order to design novel lead compounds for the treatment of fungal infections. It was discovered th...

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Autores principales: Tonoi, Takayuki, Inohana, Takehiko, Sato, Teruyuki, Noda, Yuuki, Ikeda, Miyuki, Akutsu, Miku, Murata, Takatsugu, Maekawa, Yutaro, Tanaka, Anna, Seki, Rio, Ohkusu, Misako, Kamei, Katsuhiko, Ishiwada, Naruhiko, Shiina, Isamu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804234/
https://www.ncbi.nlm.nih.gov/pubmed/31546686
http://dx.doi.org/10.3390/molecules24193437
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author Tonoi, Takayuki
Inohana, Takehiko
Sato, Teruyuki
Noda, Yuuki
Ikeda, Miyuki
Akutsu, Miku
Murata, Takatsugu
Maekawa, Yutaro
Tanaka, Anna
Seki, Rio
Ohkusu, Misako
Kamei, Katsuhiko
Ishiwada, Naruhiko
Shiina, Isamu
author_facet Tonoi, Takayuki
Inohana, Takehiko
Sato, Teruyuki
Noda, Yuuki
Ikeda, Miyuki
Akutsu, Miku
Murata, Takatsugu
Maekawa, Yutaro
Tanaka, Anna
Seki, Rio
Ohkusu, Misako
Kamei, Katsuhiko
Ishiwada, Naruhiko
Shiina, Isamu
author_sort Tonoi, Takayuki
collection PubMed
description A novel stereoisomer of eushearilide, 23-demethyleushearilide, was synthesized, and the structure–activity relationships of this compound along with known eushearilide stereoisomers were investigated in order to design novel lead compounds for the treatment of fungal infections. It was discovered that all of these congeners, together with the natural product, exhibited a wide range of antimicrobial activity against not only fungi but also against bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE).
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spelling pubmed-68042342019-11-18 Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide Tonoi, Takayuki Inohana, Takehiko Sato, Teruyuki Noda, Yuuki Ikeda, Miyuki Akutsu, Miku Murata, Takatsugu Maekawa, Yutaro Tanaka, Anna Seki, Rio Ohkusu, Misako Kamei, Katsuhiko Ishiwada, Naruhiko Shiina, Isamu Molecules Article A novel stereoisomer of eushearilide, 23-demethyleushearilide, was synthesized, and the structure–activity relationships of this compound along with known eushearilide stereoisomers were investigated in order to design novel lead compounds for the treatment of fungal infections. It was discovered that all of these congeners, together with the natural product, exhibited a wide range of antimicrobial activity against not only fungi but also against bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). MDPI 2019-09-22 /pmc/articles/PMC6804234/ /pubmed/31546686 http://dx.doi.org/10.3390/molecules24193437 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tonoi, Takayuki
Inohana, Takehiko
Sato, Teruyuki
Noda, Yuuki
Ikeda, Miyuki
Akutsu, Miku
Murata, Takatsugu
Maekawa, Yutaro
Tanaka, Anna
Seki, Rio
Ohkusu, Misako
Kamei, Katsuhiko
Ishiwada, Naruhiko
Shiina, Isamu
Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide
title Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide
title_full Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide
title_fullStr Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide
title_full_unstemmed Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide
title_short Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16Z,20E)-Eushearilide and (16E,20E)-Eushearilide
title_sort total synthesis and antimicrobial evaluation of 23-demethyleushearilide and extensive antimicrobial evaluation of all synthetic stereoisomers of (16z,20e)-eushearilide and (16e,20e)-eushearilide
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804234/
https://www.ncbi.nlm.nih.gov/pubmed/31546686
http://dx.doi.org/10.3390/molecules24193437
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