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

Hugues Fouotsa; Pierre Mkounga; Alain Meli Lannang; Jérôme Vanheuverzwijn; Zhiyu Zhou; Karine Leblanc; Somia Rharrabti; Augustin Ephrem Nkengfack; Jean-François Gallard; Véronique Fontaine; Franck Meyer; Erwan Poupon; Pierre Le Pogam; Mehdi A. Beniddir

doi:10.1039/D1OB01791H

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

Hugues Fouotsa,

^abc Pierre Mkounga,^c Alain Meli Lannang,^d Jérôme Vanheuverzwijn,^b Zhiyu Zhou,^b Karine Leblanc,^a Somia Rharrabti,^a Augustin Ephrem Nkengfack,^c Jean-François Gallard,^e Véronique Fontaine,^b Franck Meyer,^b Erwan Poupon,

^a Pierre Le Pogam

*^a and Mehdi A. Beniddir

*^a

Author affiliations

* Corresponding authors

^a Équipe “Chimie des Substances Naturelles” Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France
E-mail: pierre.le-pogam-alluard@universite-paris-saclay.fr, mehdi.beniddir@universite-paris-saclay.fr

^b Faculty of Pharmacy, Microbiology, Bioorganic and Macromolecular Chemistry Unit, Université Libre de Bruxelles, Campus de la Plaine-CP 206/04, Boulevard du Triomphe, ACC.2, Po Box 1050, Belgium

^c Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon

^d Department of Chemistry, Higher Teachers Training College, University of Maroua, P.O. Box 55, Maroua, Cameroon

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

Abstract

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 MS²-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.

This article is part of the themed collection: Chemical Biology in OBC

Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Article information

Download Citation

Permissions

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

Social activity

Search articles by author

Spotlight

Advertisements