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 dis...

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Main Authors:	Takayuki Tonoi, Takehiko Inohana, Teruyuki Sato, Yuuki Noda, Miyuki Ikeda, Miku Akutsu, Takatsugu Murata, Yutaro Maekawa, Anna Tanaka, Rio Seki, Misako Ohkusu, Katsuhiko Kamei, Naruhiko Ishiwada, Isamu Shiina
Format:	Article
Language:	English
Published:	MDPI AG 2019-09-01
Series:	Molecules
Subjects:	eushearilide demethyl congener total synthesis lactonization MNBA antimicrobial activity
Online Access:	https://www.mdpi.com/1420-3049/24/19/3437

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spelling	doaj-b61ca53b31344e698809d22ed2ead0802020-11-25T02:45:40ZengMDPI AGMolecules1420-30492019-09-012419343710.3390/molecules24193437molecules24193437Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-EushearilideTakayuki Tonoi0Takehiko Inohana1Teruyuki Sato2Yuuki Noda3Miyuki Ikeda4Miku Akutsu5Takatsugu Murata6Yutaro Maekawa7Anna Tanaka8Rio Seki9Misako Ohkusu10Katsuhiko Kamei11Naruhiko Ishiwada12Isamu Shiina13Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanDepartment of Infectious Diseases, Medical Mycology Research Center, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba-shi, Chiba 260-8673, JapanDepartment of Infectious Diseases, Medical Mycology Research Center, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba-shi, Chiba 260-8673, JapanDepartment of Infectious Diseases, Medical Mycology Research Center, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba-shi, Chiba 260-8673, JapanDepartment of Infectious Diseases, Medical Mycology Research Center, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba-shi, Chiba 260-8673, JapanDepartment of Applied Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, JapanA 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 <i>Staphylococcus aureus</i> (MRSA) and vancomycin-resistant enterococci (VRE).https://www.mdpi.com/1420-3049/24/19/3437eushearilidedemethyl congenertotal synthesislactonizationMNBAantimicrobial activity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Takayuki Tonoi Takehiko Inohana Teruyuki Sato Yuuki Noda Miyuki Ikeda Miku Akutsu Takatsugu Murata Yutaro Maekawa Anna Tanaka Rio Seki Misako Ohkusu Katsuhiko Kamei Naruhiko Ishiwada Isamu Shiina
spellingShingle	Takayuki Tonoi Takehiko Inohana Teruyuki Sato Yuuki Noda Miyuki Ikeda Miku Akutsu Takatsugu Murata Yutaro Maekawa Anna Tanaka Rio Seki Misako Ohkusu Katsuhiko Kamei Naruhiko Ishiwada Isamu Shiina Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-Eushearilide Molecules eushearilide demethyl congener total synthesis lactonization MNBA antimicrobial activity
author_facet	Takayuki Tonoi Takehiko Inohana Teruyuki Sato Yuuki Noda Miyuki Ikeda Miku Akutsu Takatsugu Murata Yutaro Maekawa Anna Tanaka Rio Seki Misako Ohkusu Katsuhiko Kamei Naruhiko Ishiwada Isamu Shiina
author_sort	Takayuki Tonoi
title	Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-Eushearilide
title_short	Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-Eushearilide
title_full	Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-Eushearilide
title_fullStr	Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-Eushearilide
title_full_unstemmed	Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-Eushearilide
title_sort	total synthesis and antimicrobial evaluation of 23-demethyleushearilide and extensive antimicrobial evaluation of all synthetic stereoisomers of (16<i>z</i>,20<i>e</i>)-eushearilide and (16<i>e</i>,20<i>e</i>)-eushearilide
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2019-09-01
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 <i>Staphylococcus aureus</i> (MRSA) and vancomycin-resistant enterococci (VRE).
topic	eushearilide demethyl congener total synthesis lactonization MNBA antimicrobial activity
url	https://www.mdpi.com/1420-3049/24/19/3437
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Total Synthesis and Antimicrobial Evaluation of 23-Demethyleushearilide and Extensive Antimicrobial Evaluation of All Synthetic Stereoisomers of (16<i>Z</i>,20<i>E</i>)-Eushearilide and (16<i>E</i>,20<i>E</i>)-Eushearilide

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