Structural Elucidation of an Atropisomeric Entcassiflavan-(4β→8)-Epicatechin Isolated from Dalbergia monetaria L.f. Based on NMR and ECD Calculations in Comparison to Experimental Data

Author:

de Moura Patrícia Homobono BritoORCID,Brandt WolfgangORCID,Porzel AndreaORCID,Martins Roberto Carlos CamposORCID,Leal Ivana Correa RamosORCID,Wessjohann Ludger A.ORCID

Abstract

A rare dihydoxyflavan-epicatechin proanthocyanidin, entcassiflavan-(4β→8)-epicatechin, was isolated from Dalbergia monetaria, a plant widely used by traditional people from the Amazon to treat urinary tract infections. The constitution and relative configuration of the compound were elucidated by HR-MS and detailed 1D- and 2D-NMR measurements. By comparing the experimental electronic circular dichroism (ECD) spectrum with the calculated ECD spectra of all 16 possible isomers, the absolute configuration, the interflavan linkage, and the atropisomers could be determined.

Funder

Coordenação de Aperfeicoamento de Pessoal de Nível Superior

National Council for Scientific and Technological Development

Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro

Leibniz Association

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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