2. Academic Validation
  3. Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve

Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve

  • J Nat Prod. 2017 Apr 28;80(4):1007-1014. doi: 10.1021/acs.jnatprod.6b01013.
Alexander E Fox Ramos 1,  Charlotte Alcover 1,  Laurent Evanno 1,  Alexandre Maciuk 1,  Marc Litaudon 2,  Christophe Duplais 3,  Guillaume Bernadat 4,  Jean-François Gallard 2,  Jean-Christophe Jullian 1,  Elisabeth Mouray 5,  Philippe Grellier 5,  Philippe M Loiseau 6,  Sébastien Pomel 6,  Erwan Poupon 1,  Pierre Champy 1,  Mehdi A Beniddir 1
Affiliations

Affiliations

  • 1 Équipe "Pharmacognosie-Chimie des Substances Naturelles" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
  • 2 Institut de Chimie des Substances Naturelles, CNRS, ICSN UPR 2301, Université Paris-Saclay , 21 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
  • 3 CNRS, UMR8172 EcoFoG, AgroParisTech, Cirad, INRA, Université des Antilles, Université de Guyane , 23 Avenue Pasteur, 97300 Cayenne, France.
  • 4 Équipe "Molécules Fluorées et Chimie Médicinale" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 rue J.-B. Clément, 92290 Châtenay-Malabry, France.
  • 5 Unité Molécules de Communication et Adaptation des Microorganismes (MCAM, UMR 7245), Muséum National d'Histoire Naturelle, CNRS, Sorbonne Universités, CP52 , 57 Rue Cuvier, 75005 Paris, France.
  • 6 Équipe "Chimiothérapie Antiparasitaire" BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay , 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France.
PMID: 28282127 DOI: 10.1021/acs.jnatprod.6b01013
Abstract

Three new Monoterpene Indole Alkaloids (1-3) have been isolated from the bark of Geissospermum laeve, together with the known Alkaloids (-)-leuconolam (4), geissolosimine (5), and geissospermine (6). The structures of 1-3 were elucidated by analysis of their HRMS and NMR spectroscopic data. The absolute configuration of geissolaevine (1) was deduced from the comparison of experimental and theoretically calculated ECD spectra. The isolation workflow was guided by a molecular networking-based dereplication strategy using an in-house database of Monoterpene Indole Alkaloids. In addition, five known compounds previously undescribed in the Geissospermum genus were dereplicated from the G. laeve alkaloid extract network and were assigned with various levels of identification confidence. The antiparasitic activities against Plasmodium falciparum and Leishmania donovani as well as the cytotoxic activity against the MRC-5 cell line were determined for compounds 1-5.

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