Journal of Natural Products, volume 80, issue 4, pages 1007-1014

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

Fox Ramos Alexander E 1
Fox Alcover Charlotte 1
Evanno Laurent 1
Maciuk Alexandre 1
Litaudon Marc 2
Duplais Christophe 3
Bernadat Guillaume 4
Gallard Jean-François 2
Jullian Jean-Christophe 1
Mouray E. 5
Grellier Philippe 5
Loiseau Philippe M. 6
Pomel Sebastien 6
Poupon Erwan 1
Champy P. 1
Beniddir Mehdi A. 1
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
6
 
Équipe “Chimiothérapie Antiparasitaire” BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 5 Rue J.-B. Clément, 92290 Châtenay-Malabry, France
Publication typeJournal Article
Publication date2017-03-10
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.1
ISSN01633864, 15206025
Organic Chemistry
Drug Discovery
Pharmacology
Pharmaceutical Science
Molecular Medicine
Complementary and alternative medicine
Analytical Chemistry
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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Fox Ramos A. E. et al. Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve // Journal of Natural Products. 2017. Vol. 80. No. 4. pp. 1007-1014.
GOST all authors (up to 50) Copy
Fox Ramos A. E., Fox Alcover C., Evanno L., Maciuk A., Litaudon M., Duplais C., Bernadat G., Gallard J., Jullian J., Mouray E., Grellier P., Loiseau P. M., Pomel S., Poupon E., Champy P., Beniddir M. A. Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve // Journal of Natural Products. 2017. Vol. 80. No. 4. pp. 1007-1014.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.jnatprod.6b01013
UR - https://doi.org/10.1021%2Facs.jnatprod.6b01013
TI - Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve
T2 - Journal of Natural Products
AU - Gallard, Jean-François
AU - Jullian, Jean-Christophe
AU - Litaudon, Marc
AU - Bernadat, Guillaume
AU - Beniddir, Mehdi A.
AU - Fox Ramos, Alexander E
AU - Fox Alcover, Charlotte
AU - Evanno, Laurent
AU - Maciuk, Alexandre
AU - Duplais, Christophe
AU - Mouray, E.
AU - Grellier, Philippe
AU - Loiseau, Philippe M.
AU - Pomel, Sebastien
AU - Poupon, Erwan
AU - Champy, P.
PY - 2017
DA - 2017/03/10 00:00:00
PB - American Chemical Society (ACS)
SP - 1007-1014
IS - 4
VL - 80
SN - 0163-3864
SN - 1520-6025
ER -
BibTex |
Cite this
BibTex Copy
@article{2017_Fox Ramos,
author = {Jean-François Gallard and Jean-Christophe Jullian and Marc Litaudon and Guillaume Bernadat and Mehdi A. Beniddir and Alexander E Fox Ramos and Charlotte Fox Alcover and Laurent Evanno and Alexandre Maciuk and Christophe Duplais and E. Mouray and Philippe Grellier and Philippe M. Loiseau and Sebastien Pomel and Erwan Poupon and P. Champy},
title = {Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve},
journal = {Journal of Natural Products},
year = {2017},
volume = {80},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021%2Facs.jnatprod.6b01013},
number = {4},
pages = {1007--1014},
doi = {10.1021/acs.jnatprod.6b01013}
}
MLA
Cite this
MLA Copy
Fox Ramos, Alexander E., et al. “Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve.” Journal of Natural Products, vol. 80, no. 4, Mar. 2017, pp. 1007-1014. https://doi.org/10.1021%2Facs.jnatprod.6b01013.
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