Unifying the configuration of historical alkaloids from Borreria capitata through an extensive spectroscopic reinvestigation.

Borrecapine Borreline Borreria capitata Monoterpene indole alkaloid Rubiaceae Structure Revision

Journal

Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434

Informations de publication

Date de publication:
Aug 2023
Historique:
received: 17 11 2022
revised: 22 05 2023
accepted: 22 05 2023
medline: 15 6 2023
pubmed: 30 5 2023
entrez: 29 5 2023
Statut: ppublish

Résumé

Reinvestigation of the structure of borrecapine and borreline through extensive spectroscopic analysis of their authentic samples led to the assignment of their absolute configurations. Newly acquired spectroscopic data determined that the previously assigned relative configuration for borrecapine was incorrect and that the claimed absolute configuration of borreline should be revised to its enantiomer.

Identifiants

pubmed: 37247764
pii: S0031-9422(23)00157-7
doi: 10.1016/j.phytochem.2023.113741
pii:
doi:

Substances chimiques

Indole Alkaloids 0
Alkaloids 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

113741

Informations de copyright

Copyright © 2023. Published by Elsevier Ltd.

Déclaration de conflit d'intérêts

Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Auteurs

Mehdi A Beniddir (MA)

Équipe "Chimie des Substances Naturelles" BioCIS, CNRS, Université Paris-Saclay, 17, Avenue des Sciences, 91400, Orsay, France. Electronic address: mehdi.beniddir@universite-paris-saclay.fr.

Adrien Jagora (A)

Équipe "Chimie des Substances Naturelles" BioCIS, CNRS, Université Paris-Saclay, 17, Avenue des Sciences, 91400, Orsay, France.

Sarah Szwarc (S)

Équipe "Chimie des Substances Naturelles" BioCIS, CNRS, Université Paris-Saclay, 17, Avenue des Sciences, 91400, Orsay, France.

Wassim Hafidi (W)

Équipe "Chimie des Substances Naturelles" BioCIS, CNRS, Université Paris-Saclay, 17, Avenue des Sciences, 91400, Orsay, France.

Jean-François Gallard (JF)

Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, 91198, Gif-sur-Yvette, France.

Pascal Retailleau (P)

Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, 91198, Gif-sur-Yvette, France.

Alexei V Buevich (AV)

Analytical Research and Development, Merck & Co., Inc., Kenilworth, NJ, 07033, United States.

Pierre Le Pogam (P)

Équipe "Chimie des Substances Naturelles" BioCIS, CNRS, Université Paris-Saclay, 17, Avenue des Sciences, 91400, Orsay, France. Electronic address: pierre.le-pogam-alluard@universite-paris-saclay.fr.

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Classifications MeSH