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New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica

The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa, collected in Corsica, allowed for the identification of three new compounds (1, 2, and 4) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysi...

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Autores principales: Esselin, Hélène, Tomi, Félix, Bighelli, Ange, Sutour, Sylvain
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017553/
https://www.ncbi.nlm.nih.gov/pubmed/29561818
http://dx.doi.org/10.3390/molecules23040720
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author Esselin, Hélène
Tomi, Félix
Bighelli, Ange
Sutour, Sylvain
author_facet Esselin, Hélène
Tomi, Félix
Bighelli, Ange
Sutour, Sylvain
author_sort Esselin, Hélène
collection PubMed
description The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa, collected in Corsica, allowed for the identification of three new compounds (1, 2, and 4) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysis. Compounds 1 and 2 are two C(15)-acetogenins sharing the same ring system: a tetrahydropyran linked by a methylene to a tetrahydrofuran ring. Compound 1 exhibits a bromoallene unit whereas compound 2 possesses an uncommon α-bromo-α,β-unsaturated aldehyde terminal unit. Compound 4 is the first diterpene exhibiting a 19(4 [Formula: see text] 3)abeo-labdane skeleton isolated from a Laurencia species. Isolation of concinndiol (compound 3) together with compound 4 suggests a common biosynthetic origin. Additionally, five known compounds, namely sagonenyne, laurene, α-bromocuparene, microcladallene A, and β-snyderol were identified in chromatographic fractions by NMR analysis using a computerized method that was developed in our laboratory.
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spelling pubmed-60175532018-11-13 New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica Esselin, Hélène Tomi, Félix Bighelli, Ange Sutour, Sylvain Molecules Article The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa, collected in Corsica, allowed for the identification of three new compounds (1, 2, and 4) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysis. Compounds 1 and 2 are two C(15)-acetogenins sharing the same ring system: a tetrahydropyran linked by a methylene to a tetrahydrofuran ring. Compound 1 exhibits a bromoallene unit whereas compound 2 possesses an uncommon α-bromo-α,β-unsaturated aldehyde terminal unit. Compound 4 is the first diterpene exhibiting a 19(4 [Formula: see text] 3)abeo-labdane skeleton isolated from a Laurencia species. Isolation of concinndiol (compound 3) together with compound 4 suggests a common biosynthetic origin. Additionally, five known compounds, namely sagonenyne, laurene, α-bromocuparene, microcladallene A, and β-snyderol were identified in chromatographic fractions by NMR analysis using a computerized method that was developed in our laboratory. MDPI 2018-03-21 /pmc/articles/PMC6017553/ /pubmed/29561818 http://dx.doi.org/10.3390/molecules23040720 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
Esselin, Hélène
Tomi, Félix
Bighelli, Ange
Sutour, Sylvain
New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica
title New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica
title_full New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica
title_fullStr New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica
title_full_unstemmed New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica
title_short New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica
title_sort new metabolites isolated from a laurencia obtusa population collected in corsica
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017553/
https://www.ncbi.nlm.nih.gov/pubmed/29561818
http://dx.doi.org/10.3390/molecules23040720
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