Combination of Machine Learning and Empirical Computation for the Structural Validation of Trirosaline, a Natural Trimeric Monoterpene Indole Alkaloid from Catharanthus roseus .

Autor: Szwarc S; Équipe 'Chimie des Substances Naturelles' Université Paris-Saclay, CNRS, BioCIS, 17 avenue des Sciences, 91400 Orsay, France., Jagora A; Équipe 'Chimie des Substances Naturelles' Université Paris-Saclay, CNRS, BioCIS, 17 avenue des Sciences, 91400 Orsay, France., Derbré S; Université Angers, SONAS, SFR QUASAV, Faculty of Health Sciences, Department of Pharmacy, 16 Bd Daviers, 49045 CEDEX 01 Angers, France., Leblanc K; Équipe 'Chimie des Substances Naturelles' Université Paris-Saclay, CNRS, BioCIS, 17 avenue des Sciences, 91400 Orsay, France., Rharrabti S; Équipe 'Chimie des Substances Naturelles' Université Paris-Saclay, CNRS, BioCIS, 17 avenue des Sciences, 91400 Orsay, France., Said-Hassane C; Unité Mixte Processus Infectieux en Milieu Insulaire Tropical, Université de la Réunion, INSERM U1187, CNRS UMR 9192, IRD UMR 249, Plateforme Technologique CYROI, 97490 Sainte Clotilde, La Réunion, France., El Kalamouni C; Unité Mixte Processus Infectieux en Milieu Insulaire Tropical, Université de la Réunion, INSERM U1187, CNRS UMR 9192, IRD UMR 249, Plateforme Technologique CYROI, 97490 Sainte Clotilde, La Réunion, France., Gallard JF; Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, 91198 Gif-sur-Yvette, France., Le Pogam P; Équipe 'Chimie des Substances Naturelles' Université Paris-Saclay, CNRS, BioCIS, 17 avenue des Sciences, 91400 Orsay, France., Beniddir MA; Équipe 'Chimie des Substances Naturelles' Université Paris-Saclay, CNRS, BioCIS, 17 avenue des Sciences, 91400 Orsay, France.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Jan 12; Vol. 26 (1), pp. 274-279. Date of Electronic Publication: 2023 Dec 22.
DOI: 10.1021/acs.orglett.3c03972
Abstrakt: Chemical investigation of the emblematic Catharanthus roseus led to the discovery of trirosaline ( 1 ), the first example of a tris-ajmalicine-type monoterpene indole alkaloid and the first natural trimeric MIA ever reported from this deeply dug plant species. Its structure was primarily elucidated based on NMR and HRESIMS analyses, and the nature of its unique intermonomeric linkages was firmly confirmed based on a combination of empirical computation and ML- J -DP4 study. Its absolute configuration was mitigated by comparison of experimental and TDDFT-simulated electronic circular dichroism (ECD) spectra. A possible biosynthetic pathway for trirosaline ( 1 ) was postulated.
Databáze: MEDLINE
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