Dalbergia monetaria proanthocyanidin Structural elucidation of an atropoisomeric entcassiflavan-(4beta-->8)-epicatechin isolated from Dalbergia monetaria L.f based on ECD calculations in comparison to experimental data

DOI

A rare dihydoxyflavan-epicatechin proanthocyanidin, entcassiflavan-(4  8)-epicatechin, has been 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.

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InChI=1S/C30H26O9/c31-16-4-1-14(2-5-16)26-12-19(18-7-6-17(32)10-27(18)38-26)28-24(36)13-22(34)20-11-25(37)29(39-30(20)28)15-3-8-21(33)23(35)9-15/h1-10,13,19,25-26,29,31-37H,11-12H2/t19-,25-,26-,29-/m1/s1

Identifier
DOI https://doi.org/10.22000/528
Related Identifier https://doi.org/10.3390/molecules27082512
Metadata Access https://www.radar-service.eu/oai/OAIHandler?verb=GetRecord&metadataPrefix=datacite&identifier=10.22000/528
Provenance
Creator Homobono Brito de Moura, Patricia (Natural Products Research Institute (IPPN), Center of Health Sciences, Federal University of Rio de Janeiro (UFRJ), Rio de Janeiro, RJ, Brazil; Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), Germany); Brandt, Wolfgang (Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), Germany); Porzel, Andrea (Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), Germany); Martins, Roberto Carlos Campos (Natural Products Research Institute (IPPN), Center of Health Sciences, Federal University of Rio de Janeiro (UFRJ), Rio de Janeiro, RJ, Brazil); Correa Ramos Leal, Ivana (Natural Products and Food Department, Pharmacy Faculty, Center of Health Sciences, Federal University of Rio de Janeiro (UFRJ), Rio de Janeiro, RJ, Brazil); Wessjohann, Ludger A. (Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), Germany)
Publisher Leibniz Institute of Plant Biochemistry (IPB), Weinberg 3, 06120 Halle (Saale), Germany
Contributor RADAR
Publication Year 2022
Funding Reference Coordenação de Aperfeicoamento de Pessoal de Nível Superior (CAPES), PDSE 88881 133771 2016 01; Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), 312045 2014 0; Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ), E 26 202 817 2015; Leibniz-Institut für Pflanzenbiochemie
Rights CC BY 4.0 Attribution
OpenAccess true
Representation
Language English
Resource Type NMR, MS, ECD spectra, calculated ECD spectra; Dataset
Format application/zip
Discipline Chemistry; Natural Sciences