DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>

DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>

A phytochemical investigation of the foliose lichen <i>Parmotrema tsavoense</i> (Krog and Swinscow) Krog and Swinscow (Parmeliaceae) resulted in the isolation of a new trichlorinated xanthone, isodemethylchodatin. The structure elucidation of this new norlichexanthone derivative proved t...

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Main Authors: Thuc-Huy Duong, Mehdi A. Beniddir, Joël Boustie, Kim-Phi-Phung Nguyen, Warinthorn Chavasiri, Guillaume Bernadat, Pierre Le Pogam
Format: Article
Language:English
Published: MDPI AG 2019-04-01
Series:Molecules
Subjects:
lichen
xanthone
norlichexanthone
<i>Parmotrema</i>
DFT-NMR
Online Access:https://www.mdpi.com/1420-3049/24/8/1527
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spelling doaj-24e6dd5c288c4a42a54cc05bb3b0bfbd2020-11-25T00:19:11ZengMDPI AGMolecules1420-30492019-04-01248152710.3390/molecules24081527molecules24081527DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>Thuc-Huy Duong0Mehdi A. Beniddir1Joël Boustie2Kim-Phi-Phung Nguyen3Warinthorn Chavasiri4Guillaume Bernadat5Pierre Le Pogam6Department for Management of Science and Technology Development, Ton Duc Thang University, Ho Chi Minh City 748355, VietnamÉquipe “Pharmacognosie–Chimie des Substances Naturelles”, BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 5 Rue Jean-Baptiste Clément, 92290 Châtenay-Malabry, FranceCNRS, ISCR (Institut des Sciences Chimiques de Rennes)–UMR 6226, Univ Rennes, F-35000 Rennes, FranceDepartment of Organic Chemistry, University of Science, National University–Ho Chi Minh City, 227 Nguyen Van Cu Str., Dist. 5, Ho Chi Minh City 748355, VietnamNatural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Rd., Patumwan, Bangkok 10330, ThailandÉquipe “Pharmacognosie–Chimie des Substances Naturelles”, BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 5 Rue Jean-Baptiste Clément, 92290 Châtenay-Malabry, FranceÉquipe “Pharmacognosie–Chimie des Substances Naturelles”, BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 5 Rue Jean-Baptiste Clément, 92290 Châtenay-Malabry, FranceA phytochemical investigation of the foliose lichen <i>Parmotrema tsavoense</i> (Krog and Swinscow) Krog and Swinscow (Parmeliaceae) resulted in the isolation of a new trichlorinated xanthone, isodemethylchodatin. The structure elucidation of this new norlichexanthone derivative proved tricky owing to proton deficiency, and to the lack of NMR data of closely related analogues. The structure of this compound was determined based on an integrated interpretation of <sup>13</sup>C-NMR chemical shifts, MS spectra, and DP4-based computational chemistry was also performed to provide an independent and unambiguous validation of the determined structure. Isodemethylchodatin represents the first chlorinated lichexanthone/norlichexanthone derivative bearing a methoxy group at C-5.https://www.mdpi.com/1420-3049/24/8/1527lichenxanthonenorlichexanthone<i>Parmotrema</i>DFT-NMR
collection DOAJ
language English
format Article
sources DOAJ
author Thuc-Huy Duong
Mehdi A. Beniddir
Joël Boustie
Kim-Phi-Phung Nguyen
Warinthorn Chavasiri
Guillaume Bernadat
Pierre Le Pogam
spellingShingle Thuc-Huy Duong
Mehdi A. Beniddir
Joël Boustie
Kim-Phi-Phung Nguyen
Warinthorn Chavasiri
Guillaume Bernadat
Pierre Le Pogam
DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>
Molecules
lichen
xanthone
norlichexanthone
<i>Parmotrema</i>
DFT-NMR
author_facet Thuc-Huy Duong
Mehdi A. Beniddir
Joël Boustie
Kim-Phi-Phung Nguyen
Warinthorn Chavasiri
Guillaume Bernadat
Pierre Le Pogam
author_sort Thuc-Huy Duong
title DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>
title_short DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>
title_full DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>
title_fullStr DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>
title_full_unstemmed DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen <i>Parmotrema tsavoense</i>
title_sort dp4-assisted structure elucidation of isodemethylchodatin, a new norlichexanthone derivative meager in h-atoms, from the lichen <i>parmotrema tsavoense</i>
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2019-04-01
description A phytochemical investigation of the foliose lichen <i>Parmotrema tsavoense</i> (Krog and Swinscow) Krog and Swinscow (Parmeliaceae) resulted in the isolation of a new trichlorinated xanthone, isodemethylchodatin. The structure elucidation of this new norlichexanthone derivative proved tricky owing to proton deficiency, and to the lack of NMR data of closely related analogues. The structure of this compound was determined based on an integrated interpretation of <sup>13</sup>C-NMR chemical shifts, MS spectra, and DP4-based computational chemistry was also performed to provide an independent and unambiguous validation of the determined structure. Isodemethylchodatin represents the first chlorinated lichexanthone/norlichexanthone derivative bearing a methoxy group at C-5.
topic lichen
xanthone
norlichexanthone
<i>Parmotrema</i>
DFT-NMR
url https://www.mdpi.com/1420-3049/24/8/1527
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