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Connection of Isolated Stereoclusters by Combining (13)C-RCSA, RDC, and J-Based Configurational Analyses and Structural Revision of a Tetraprenyltoluquinol Chromane Meroterpenoid from Sargassum muticum

The seaweed Sargassum muticum, collected on the southern coast of Galicia, yielded a tetraprenyltoluquinol chromane meroditerpene compound known as 1b, whose structure is revised. The relative configuration of 1b was determined by J-based configurational methodology combined with an iJ/DP4 statistic...

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Detalles Bibliográficos
Autores principales: Fuentes-Monteverde, Juan Carlos C., Nath, Nilamoni, Forero, Abel M., Balboa, Elena M., Navarro-Vázquez, Armando, Griesinger, Christian, Jiménez, Carlos, Rodríguez, Jaime
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9319238/
https://www.ncbi.nlm.nih.gov/pubmed/35877755
http://dx.doi.org/10.3390/md20070462
Descripción
Sumario:The seaweed Sargassum muticum, collected on the southern coast of Galicia, yielded a tetraprenyltoluquinol chromane meroditerpene compound known as 1b, whose structure is revised. The relative configuration of 1b was determined by J-based configurational methodology combined with an iJ/DP4 statistical analysis and further confirmed by measuring two anisotropic properties: carbon residual chemical shift anisotropies ((13)C-RCSAs) and one-bond (1)H-(13)C residual dipolar couplings ((1)D(CH)-RDCs). The absolute configuration of 1b was deduced by ECD/OR/TD-DFT methods and established as 3R,7S,11R.