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Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis

Wentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against α,α-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative...

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Autores principales: Li, Xin, Li, Xiao-Ming, Wang, Bin-Gui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6356208/
https://www.ncbi.nlm.nih.gov/pubmed/30586855
http://dx.doi.org/10.3390/md17010008
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author Li, Xin
Li, Xiao-Ming
Wang, Bin-Gui
author_facet Li, Xin
Li, Xiao-Ming
Wang, Bin-Gui
author_sort Li, Xin
collection PubMed
description Wentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against α,α-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative (1,10-dihydroxy-3-(hydroxymethyl)-8-methoxydibenzo [b,e]oxepine-6,11-dione, 1) by 1D and 2D NMR experiments. However, the minor differences of the chemical shifts between xanthones and anthraquinones were queried, leading to the structure of 1 to be revised as a xanthone analog (8-hydroxy-6-(hydroxymethyl)-3-methoxy-9-oxo-9H-xanthene-1-carboxylic acid, 2) on the basis of a methylation and subsequent NMR measurements, and was confirmed by X-ray crystallographic analysis. The method established in this paper could be applied to the structural re-examination or revision for some of the reported seco-anthraquinone derivatives.
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spelling pubmed-63562082019-02-05 Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis Li, Xin Li, Xiao-Ming Wang, Bin-Gui Mar Drugs Article Wentiquinone C, which was previously isolated from the marine brown alga-derived endophytic fungus Aspergillus wentii EN-48, was found to be a potent antioxidant against α,α-diphenyl-picrylhydrazyl (DPPH) radical. The structure of wentiquinone C was originally assigned as an anthraquinone derivative (1,10-dihydroxy-3-(hydroxymethyl)-8-methoxydibenzo [b,e]oxepine-6,11-dione, 1) by 1D and 2D NMR experiments. However, the minor differences of the chemical shifts between xanthones and anthraquinones were queried, leading to the structure of 1 to be revised as a xanthone analog (8-hydroxy-6-(hydroxymethyl)-3-methoxy-9-oxo-9H-xanthene-1-carboxylic acid, 2) on the basis of a methylation and subsequent NMR measurements, and was confirmed by X-ray crystallographic analysis. The method established in this paper could be applied to the structural re-examination or revision for some of the reported seco-anthraquinone derivatives. MDPI 2018-12-24 /pmc/articles/PMC6356208/ /pubmed/30586855 http://dx.doi.org/10.3390/md17010008 Text en © 2018 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
Li, Xin
Li, Xiao-Ming
Wang, Bin-Gui
Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
title Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
title_full Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
title_fullStr Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
title_full_unstemmed Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
title_short Structural Revision of Wentiquinone C and Related Congeners from Anthraquinones to Xanthones Using Chemical Derivatization and NMR Analysis
title_sort structural revision of wentiquinone c and related congeners from anthraquinones to xanthones using chemical derivatization and nmr analysis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6356208/
https://www.ncbi.nlm.nih.gov/pubmed/30586855
http://dx.doi.org/10.3390/md17010008
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