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

1
Department for Management of Science and Technology Development, Ton Duc Thang University, Ho Chi Minh City 748355, Vietnam
2
Faculty of Applied Sciences, Ton Duc Thang University, Ho Chi Minh City 748355, Vietnam
3
Équipe “Pharmacognosie–Chimie des Substances Naturelles”, BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 5 Rue Jean-Baptiste Clément, 92290 Châtenay-Malabry, France
4
CNRS, ISCR (Institut des Sciences Chimiques de Rennes)–UMR 6226, Univ Rennes, F-35000 Rennes, France
5
Department of Organic Chemistry, University of Science, National University–Ho Chi Minh City, 227 Nguyen Van Cu Str., Dist. 5, Ho Chi Minh City 748355, Vietnam
6
Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Rd., Patumwan, Bangkok 10330, Thailand
*
Authors to whom correspondence should be addressed.
Academic Editor: Wolfgang Robien
Molecules 2019, 24(8), 1527; https://doi.org/10.3390/molecules24081527
Received: 28 February 2019 / Revised: 14 April 2019 / Accepted: 15 April 2019 / Published: 18 April 2019
(This article belongs to the Special Issue NMR Spectroscopy in Natural Product Structure Elucidation)
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Abstract

A phytochemical investigation of the foliose lichen Parmotrema tsavoense (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 13C-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. View Full-Text
Keywords: lichen; xanthone; norlichexanthone; Parmotrema; DFT-NMR lichen; xanthone; norlichexanthone; Parmotrema; DFT-NMR
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Duong, T.-H.; Beniddir, M.A.; Boustie, J.; Nguyen, K.-P.-P.; Chavasiri, W.; Bernadat, G.; Le Pogam, P. DP4-Assisted Structure Elucidation of Isodemethylchodatin, a New Norlichexanthone Derivative Meager in H-Atoms, from the Lichen Parmotrema tsavoense. Molecules 2019, 24, 1527.

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