Pyrrovobasine, hybrid alkylated pyrraline monoterpene indole alkaloid pseudodimer discovered using a combination of mass spectral and NMR-based machine learning annotations - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2021

Pyrrovobasine, hybrid alkylated pyrraline monoterpene indole alkaloid pseudodimer discovered using a combination of mass spectral and NMR-based machine learning annotations

Véronique Fontaine
Franck Meyer

Résumé

A new vobasine–tryptamine-based monoterpene indole alkaloid pseudodimer was isolated from the stem bark of Voacanga africana. As a minor constituent occurring in a thoroughly investigated plant, this molecule was targeted based on a molecular networking strategy and a rational MS -guided phytochemical investigation led to its isolation. Its structure was formally established based on HRMS, 1D/2D NMR data, and the application of the tool Small Molecule Accurate Recognition Technology (SMART 2.0). Its absolute configuration was assigned by the exciton chirality method and TD-DFT ECD calculations. Besides featuring an unprecedented intermonomeric linkage in the small group of vobasine/tryptamine hybrids, pyrrovobasine also represents the first pyrraline-containing representative in the whole monoterpene indole alkaloids group. Biosynthetic hypotheses possibly underpinning these structural oddities are proposed here.

Domaines

Chimie
Fichier principal
Vignette du fichier
Fouotsa_org_biomol_chem_2022.pdf (842.29 Ko) Télécharger le fichier

Dates et versions

hal-04082218 , version 1 (15-01-2024)

Identifiants

Citer

Hugues Fouotsa, Pierre Mkounga, Alain Meli Lannang, Jérôme Vanheuverzwijn, Zhiyu Zhou, et al.. Pyrrovobasine, hybrid alkylated pyrraline monoterpene indole alkaloid pseudodimer discovered using a combination of mass spectral and NMR-based machine learning annotations. Organic & Biomolecular Chemistry, 2021, 20 (1), pp.98-105. ⟨10.1039/d1ob01791h⟩. ⟨hal-04082218⟩
28 Consultations
54 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More