Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis

Abstract A new acylphloroglucinol with a novel architecture including an unprecedented dearomatic dibenzofuran core, named callistemenonone A (1), was isolated from the leaves of Callistemon viminalis (Myrtaceae). The structure was fully characterized on the basis of extensive spectroscopic analysis...

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Autores principales:	Yu-Qing Xiang, Hong-Xin Liu, Li-Yun Zhao, Zhi-Fang Xu, Hai-Bo Tan, Sheng-Xiang Qiu
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/ed9d872af76a4747ba79286549cfbfbf
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spelling	oai:doaj.org-article:ed9d872af76a4747ba79286549cfbfbf2021-12-02T12:30:45ZCallistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis10.1038/s41598-017-02441-52045-2322https://doaj.org/article/ed9d872af76a4747ba79286549cfbfbf2017-05-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-02441-5https://doaj.org/toc/2045-2322Abstract A new acylphloroglucinol with a novel architecture including an unprecedented dearomatic dibenzofuran core, named callistemenonone A (1), was isolated from the leaves of Callistemon viminalis (Myrtaceae). The structure was fully characterized on the basis of extensive spectroscopic analysis, including UV, HRESIMS, as well as 1D and 2D NMR spectral data (HSQC, HMBC, and ROESY). The deduced structure represents the first example of a natural dibenzofuran with two phenyl moieties coupling through tertiary hydroxy and ketal carbons. A plausible biogenetic pathway involving oxidative coupling and dearomatization as key steps is proposed to account for the biosynthesis of this novel class of dibenzofuran. Moreover, antimicrobial assays, in conjunction with the time-killing and biophysical studies, revealed that 1 exerted potent bactericidal activity against a panel of methicillin resistant pathogenic microbes with a unique mechanism.Yu-Qing XiangHong-Xin LiuLi-Yun ZhaoZhi-Fang XuHai-Bo TanSheng-Xiang QiuNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-8 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Yu-Qing Xiang Hong-Xin Liu Li-Yun Zhao Zhi-Fang Xu Hai-Bo Tan Sheng-Xiang Qiu Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis
description	Abstract A new acylphloroglucinol with a novel architecture including an unprecedented dearomatic dibenzofuran core, named callistemenonone A (1), was isolated from the leaves of Callistemon viminalis (Myrtaceae). The structure was fully characterized on the basis of extensive spectroscopic analysis, including UV, HRESIMS, as well as 1D and 2D NMR spectral data (HSQC, HMBC, and ROESY). The deduced structure represents the first example of a natural dibenzofuran with two phenyl moieties coupling through tertiary hydroxy and ketal carbons. A plausible biogenetic pathway involving oxidative coupling and dearomatization as key steps is proposed to account for the biosynthesis of this novel class of dibenzofuran. Moreover, antimicrobial assays, in conjunction with the time-killing and biophysical studies, revealed that 1 exerted potent bactericidal activity against a panel of methicillin resistant pathogenic microbes with a unique mechanism.
format	article
author	Yu-Qing Xiang Hong-Xin Liu Li-Yun Zhao Zhi-Fang Xu Hai-Bo Tan Sheng-Xiang Qiu
author_facet	Yu-Qing Xiang Hong-Xin Liu Li-Yun Zhao Zhi-Fang Xu Hai-Bo Tan Sheng-Xiang Qiu
author_sort	Yu-Qing Xiang
title	Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis
title_short	Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis
title_full	Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis
title_fullStr	Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis
title_full_unstemmed	Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis
title_sort	callistemenonone a, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from callistemon viminalis
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/ed9d872af76a4747ba79286549cfbfbf
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Callistemenonone A, a novel dearomatic dibenzofuran-type acylphloroglucinol with antimicrobial activity from Callistemon viminalis

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