Issue 1, 2022

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
12 sept. 2021
Accepted
27 sept. 2021
First published
27 sept. 2021

Org. Biomol. Chem., 2022,20, 98-105

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

H. Fouotsa, P. Mkounga, A. M. Lannang, J. Vanheuverzwijn, Z. Zhou, K. Leblanc, S. Rharrabti, A. E. Nkengfack, J. Gallard, V. Fontaine, F. Meyer, E. Poupon, P. Le Pogam and M. A. Beniddir, Org. Biomol. Chem., 2022, 20, 98 DOI: 10.1039/D1OB01791H

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