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

Journal: Organic & biomolecular chemistry
PMID: 34596204

Abstract

A new vobasine-tryptamine-based monoterpene indole alkaloid pseudodimer was isolated from the stem bark of . 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.

Authors

  • Hugues Fouotsa
    Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Pierre Mkounga
    Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon.
  • Alain Meli Lannang
    Department of Chemistry, Higher Teachers Training College, University of Maroua, P.O. Box 55, Maroua, Cameroon.
  • Jérôme Vanheuverzwijn
    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.
  • Zhiyu Zhou
    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.
  • Karine Leblanc
    Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Somia Rharrabti
    Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Augustin Ephrem Nkengfack
    Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon.
  • Jean-François Gallard
    Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay, 91198 Gif-sur-Yvette, France.
  • Véronique Fontaine
    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.
  • Franck Meyer
    Laboratory of Biopolymers and Supramolecular Nanomaterials, Faculté de Pharmacie, Université Libre de Bruxelles (ULB), Campus Plaine (CP 206/4), Boulevard du Triomphe, 1050 Brussels, Belgium.
  • Erwan Poupon
    Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Pierre Le Pogam
    Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.
  • Mehdi A Beniddir
    Équipe "Chimie des Substances Naturelles" Université Paris-Saclay, CNRS, BioCIS, 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France. pierre.le-pogam-alluard@universite-paris-saclay.fr.

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