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

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Fuentes-Monteverde, Juan Carlos
Nath, Nilamoni
Forero, Abel M.
Balboa, Elena M.
Navarro-Vázquez, Armando
Griesinger, Christian

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Fuentes-Monteverde, J.C.C.; Nath, N.; Forero, A.M.; Balboa, E.M.; Navarro-Vázquez, A.; Griesinger, C.; Jiménez, C.; Rodríguez, J. Connection of Isolated Stereoclusters by Combining 13C-RCSA, RDC, and J-Based Configurational Analyses and Structural Revision of a Tetraprenyltoluquinol Chromane Meroterpenoid from Sargassum muticum. Mar. Drugs 2022, 20, 462. https://doi.org/10.3390/md20070462

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Abstract

[Abstract] 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 (13C-RCSAs) and one-bond 1H-13C residual dipolar couplings (1DCH-RDCs). The absolute configuration of 1b was deduced by ECD/OR/TD-DFT methods and established as 3R,7S,11R.

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This article belongs to the Special Issue Marine Drugs Research in Spain

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Atribución 4.0 Internacional (CC BY 4.0)
Atribución 4.0 Internacional (CC BY 4.0)

Except where otherwise noted, this item's license is described as Atribución 4.0 Internacional (CC BY 4.0)