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1. 4-Deoxyphorbol inhibits HIV-1 infection in synergism with antiretroviral drugs and reactivates viral reservoirs through PKC/MEK activation synergizing with vorinostat

Author

De la Torre-Tarazona, H.E., primary, Jiménez, R., additional, Bueno, P., additional, Camarero, S., additional, Román, L., additional, Fernández-García, J.L., additional, Beltrán, M., additional, Nothias, L.F., additional, Cachet, X., additional, Paolini, J., additional, Litaudon, M., additional, Alcami, J., additional, and Bedoya, L.M., additional

Published
2020
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7. Collected mass spectrometry data on monoterpene indole alkaloids from natural product chemistry research

Author

Universitat Rovira i Virgili, Fox Ramos AE, Le Pogam P, Fox Alcover C, Otogo N'Nang E, Cauchie G, Hazni H, Awang K, Bréard D, Echavarren AM, Frédérich M, Gaslonde T, Girardot M, Grougnet R, Kirillova MS, Kritsanida M, Lémus C, Le Ray AM, Lewin G, Litaudon M, Mambu L, Michel S, Miloserdov FM, Muratore ME, Richomme-Peniguel P, Roussi F, Evanno L, Poupon E, Champy P, Beniddir MA, Universitat Rovira i Virgili, and Fox Ramos AE, Le Pogam P, Fox Alcover C, Otogo N'Nang E, Cauchie G, Hazni H, Awang K, Bréard D, Echavarren AM, Frédérich M, Gaslonde T, Girardot M, Grougnet R, Kirillova MS, Kritsanida M, Lémus C, Le Ray AM, Lewin G, Litaudon M, Mambu L, Michel S, Miloserdov FM, Muratore ME, Richomme-Peniguel P, Roussi F, Evanno L, Poupon E, Champy P, Beniddir MA

Abstract

This Data Descriptor announces the submission to public repositories of the monoterpene indole alkaloid database (MIADB), a cumulative collection of 172 tandem mass spectrometry (MS/MS) spectra from multiple research projects conducted in eight natural product chemistry laboratories since the 1960s. All data have been annotated and organized to promote reuse by the community. Being a unique collection of these complex natural products, these data can be used to guide the dereplication and targeting of new related monoterpene indole alkaloids within complex mixtures when applying computer-based approaches, such as molecular networking. Each spectrum has its own accession number from CCMSLIB00004679916 to CCMSLIB00004680087 on the GNPS. The MIADB is available for download from MetaboLights under the identifier: MTBLS142 ( https://www.ebi.ac.uk/metabolights/MTBLS142 ).

Published
2019

9. Welcoming the green metabolomic era: supercritical fluid chromatography, tandem mass spectrometry, and molecular networking, as an efficient workflow to explore metabolome and isolate targeted compound

Author

Nothias-Scaglia, L-F, Boutet-Mercey, S., Cachet, X., de la Torre, H-E, Costa, J., Paolini, J., Bedoya, L-M, Alcami, J., Leyssen, P., Brunelle, A., Roussi, F., Touboul, D., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2016

10. Molecular networking of MS/MS as a tool to target antiviral diterpenoids from Corsican Euphorbia

Author

Esposito, M., Nothias-Scaglia, L-F, Leyssen, P., Roussi, F., Touboul, D., Costa, J., Paolini, J., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2016

12. HPLC-MS² dereplication and profiling of diterpene esters from Euphorbia extracts with anti-chikungunya virus activity

Author

Nothias-Scaglia, L-F, Schmitz-Afonso, Isabelle, Renucci, F., Roussi, F., Leyssen, P., Touboul, D., Costa, J., Litaudon, M., Paolini, J., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2015

13. Massive multi-informative molecular networks : a map to navigate through the chemical space of bioactive Euphorbiaceae

Author

Allard, P.M., Nothias-Scaglia, L-F, Cachet, X., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2015

14. Accelerating Natural Products Research Workflow by MS/MS Molecular Networking: an Efficient Approach Toward the Study of Euphorbia species

Author

Nothias-Scaglia, L-F, Esposito, M., Cachet, X., Roussi, F., Costa, J., Leyssen, P., Paolini, J., Touboul, D., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2015

22. Molecular Networking, an Innovative Tool for Natural Products Research: Application to the Phytochemical Studies of Euphorbia Species

Author

Nothias-Scaglia, L-F, Esposito, M., Cachet, X., Costa, J., Roussi, F., Paolini, J., Touboul, D., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2015

23. Molecular Networking for Structure-Guided Purification of Diterpene Esters from Euphorbia Species

Author

Nothias-Scaglia, L-F, Esposito, M., Cachet, X., Costa, J., Roussi, F., Paolini, J., Touboul, D., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2015

24. Antiviral Activity of Diterpene Esters on Chikungunya Virus and HIV Replication , Phorbol-12,13-didecanoate

Author

Nothias-Scaglia, L-F, Pannecouque, C., Renucci, F., Delang, L., Neyts, J., Roussi, F., Costa, J., Leyssen, P., Litaudon, M., Paolini, J., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
Chikungunya Virus, jatrophane diterpenoids, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Antiviral Activity, daphnane, virus diseases, HIV Replication, tigliane
Abstract

International audience; Recently, new daphnane, tigliane, and jatrophane diterpenoids have been isolated from various Euphorbiaceae species, of which some have been shown to be potent inhibitors of chikungunya virus (CHIKV) replication. To further explore this type of compound, the antiviral activity of a series of 29 commercially available natural diterpenoids was evaluated. Phorbol-12,13-didecanoate (11) proved to be the most potent inhibitor, with an EC50 value of 6.0 ± 0.9 nM and a selectivity index (SI) of 686, which is in line with the previously reported anti-CHIKV potency for the structurally related 12-O-tetradecanoylphorbol-13-acetate (13). Most of the other compounds exhibited low to moderate activity, including an ingenane-type diterpene ester, compound 28, with an EC50 value of 1.2 ± 0.1 μM and SI = 6.4. Diterpene compounds are known also to inhibit HIV replication, so the antiviral activities of compounds 1−29 were evaluated also against HIV-1 and HIV-2. Tigliane- (4β-hydroxyphorbol analogues 10, 11, 13, 15, 16, and 18) and ingenane-type (27 and 28) diterpene esters were shown to inhibit HIV replication in vitro at the nanomolar level. A Pearson analysis performed with the anti-CHIKV and anti-HIV data sets demonstrated a linear relationship, which supported the hypothesis made that PKC may be an important target in CHIKV replication.

Published
2015

25. New Insights on Profiling of Phorbol, Deoxyphorbol, Ingenol and Jatrophane Diterpene Esters by High Performance Liquid Chromatography coupled to Multiple Stage Mass Spectrometry

Author

Nothias, L.F, Schmitz-Afonso, Isabelle, Renucci, F., Roussi, F., Touboul, D., Costa, J., Litaudon, M., Paolini, J., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
Deoxyphorbol, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Phorbol, Ingenol, Diterpene Esters, Jatrophane, HPLC-MS2
Abstract

International audience; This paper reports our effort to develop a comprehensive HPLC-MSn-based dereplication strategy for phorbol ester (PE), deoxyphorbol ester (DE) and ingenol ester (IE) profiling in plant extracts. The method consisted in two sequential analysis exploiting specific hybrid triple quadrupole/linear ion trap instrument modes. A first run was performed using a multiple reaction monitoring (MRM) mode targeting fragmentation of PE and DE/IE coupled with the acquisition of MS2 spectrum for the ions at m/z 311 and m/z 313, respectively. A second run was then completed based on precursor ion scan mode (PIS) and automatic MS2 acquisition for each pseudo-molecular ion. The developed approach was used to investigate ten Euphorbia extracts showing bioactivity against chikungunya virus replication. Experiments allowed partial annotation of three DE/IE but no PE was detected. Results suggested that other types of diterpene esters displayed PE- and DE/IE-like fragmentations. The study of jatrophane ester (JE) standards by CID fragmentation using low and high resolution mass spectrometry confirmed this hypothesis. Highlighting challenges and difficulties of diterpene esters profiling within plant extracts. Nonetheless, the present LC-MSn method can be easily adapted to profile other types of diterpene esters.

Published
2015

26. A Molecular Networking Based Workflow for an Efficient Phytochemical Study of Euphorbia pithyusa L. Plant Species

Author

Esposito, M., Nothias-Scaglia, L-F, Leyssen, P., Roussi, F., Touboul, D., Costa, J., Litaudon, M., Paolini, J., Renucci, Franck, RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2015

27. Prospective écologie chimique

Author

Barthes, N., Jauffret, P., Litaudon, M., Petek, Sylvain, Thomas, O., Hossaert, M. (ed.), Barthes, N. (ed.), Abbadie, L. (collab.), Al-Mourabit, A. (collab.), Bagnères, A.G. (collab.), Caissard, J.C. (collab.), Grison, C. (collab.), Le Bris, N. (collab.), Leblanc, C. (collab.), Litaudon, M. (collab.), Lucas, C. (collab.), Pérez, T. (collab.), Potin, P. (collab.), Rebuffat, S. (collab.), Schatz, B. (collab.), and Smadja, C. (collab.)

Subjects
SGBD, BASE DE DONNEES, ECOLOGIE, METHODOLOGIE, ECOLOGIE CHIMIQUE
Published
2012

28. Antiviral Diterpenes Polyesters from Corsican Euphorbia Species

Author

Nothias-Scaglia, L-F, Dumontet, V., Leyssen, P., Retailleau, P., gallard, J.F., Roussi, F., Paolini, J., Costa, J., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Renucci, Franck

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2014

29. Phytochemical Investigation of Antiviral Euphorbia Species from Corsica

Author

Nothias, L.F, Dumontet, V., Leyssen, P., Retailleau, P., Gueritte, F., Costa, J., Litaudon, M., Paolini, J., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2014

30. Antiviral Diterpenes from Corsican Euphorbia Species

Author

Nothias, L.F, Dumontet, V., Leyssen, P., Paolini, J., Retailleau, P., Guéritte, F., Costa, J., Litaudon, M., RN, Sciences pour l'environnement (SPE), Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2013

31. Diterpenoids from Euphorbiaceae with Potent Anti-CHIKV and Anti-HIV Activities: Are these Antiviral Properties Correlated?

Author

Litaudon, M., Nothias, L.F, Allard, P.M., Bourjot, M., Dumontet, V., Gueritte, F., Delang, L., Pannecouque, C., Paolini, J., Costa, J., Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), RN, Sciences pour l'environnement (SPE), and Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)-Centre National de la Recherche Scientifique (CNRS)-Université Pascal Paoli (UPP)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2013

33. Regioselective and Stereospecific Methoxylation of Aucubin: An access to Novel Antibacterial Iridoid Derivatives

Author

El Mourabet, M., Lecsö, M., Salle De Chou, Y., Markovic, D., Litaudon, M., Butel, M.-J., and Deguin B.

Subjects
Aucubin, Aucuba japonica Thumb, Antibiotic, Iridoid, chiral pool syntheses
Abstract

The use of natural iridoid glycosides as starting materials for the synthesis of biologically active compounds received considerable attention in the last decade. Aucubin rapidly appeared particularly suitable for the synthetic use since it is readily available in large amounts from the fresh aerial parts of a Aucuba japonica Thumb. Indeed aucubin in readily indeed aucubin analogues monoterpene basic core permitted the chiral pool syntheses of insect antifeedance, carboxylic nucleoside analogs, amiinocyclopentitol glycloside inhibitors and numerous prostagladins. More recent synthetic applications took advantage of both the aglycone and glucose moieties present in the natural iridoid as illustrated by the synthesis of homochiral rigid amino acid glucosides, citotoxic cyclopentanone glucosides and polyaminoiridoids whose structure may be related to the aminoside antibiotics. In this context, the development of techniques permitting successive or simultaneous modification of the aglycone and the glucose unit appeared particularly desirable, in order to access to the enlarged variety of synthetic derivatives of aucubin. When performed on the aucubin-derived substrates, diverse selective protection gave an access to the library of 17 aucubin derivatives. The antibacterial evaluation of these series led to the identification of a potential novel antibiotic compounds. We are knowledge financial support from the ANR (ANR-09-CP2D-09).

Published
2013

34. Cytotoxic prenylated acetophenone dimers from Acronychia pedunculata

Author

Kouloura, E. Halabalaki, M. Lallemand, M.-C. Nam, S. Jove, R. Litaudon, M. Awang, K. Hadi, H.A. Skaltsounis, A.-L.

Abstract

Three new acetophenone dimers or Acronychia-type acetophenones, acropyrone (1), acropyranol A (2), and acropyranol B (3), were isolated from the trunk bark of Acronychia pedunculata and structurally characterized, together with four known acetophenone dimers, acrovestone (4), acrovestenol (5), acrofolione A (6), and acrofolione B (7), the acetophenone monomer acronyline (8), and four furoquinoline alkaloids. The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of the isolated acetophenone dimers were evaluated against the DU145 prostate and A2058 melanoma human cancer cell lines as well as the NHDF normal cell line. Acrovestone (4) and acrovestenol (5) exhibited substantial cytotoxicity, with IC50 values of 0.38 and 2.8 μM against A2058 melanoma cells as well as 0.93 and 2.7 μM against DU145 prostate cancer cells, respectively. © 2012 The American Chemical Society and American Society of Pharmacognosy.

Published
2012

37. Plantes de Nouvelle-Calédonie d'intérêt biologique : de la création du 'Laboratoire des Plantes Médicinales' (ICSN-CNRS) à Nouméa aux recherches actuelles

Author

Guéritte, F., Dumontet, V., Poullain, C., Litaudon, M., Sévenet, T., Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Brunet, Jocelyne

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2010

38. New caledonian ARAUCARIACEAE / Araucaria laubenfelsii

Author

M. Sarrailh, J., P. Chauvin, J., Litaudon, M., Dumontet, V., Pieters, R., Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2006

39. New cytotoxic guttiferone analogues from Garcinia virgata from New Caledonia

Author

Merza, J., Mallet, S., Litaudon, M., Dumontet, V., Seraphin, D., Richomme, P., Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Published
2006

40. Chemical constituents from Croton insularis

Author

Graikou, K. Aligiannis, N. Chinou, I. Skaltsounis, A.-L. Tillequin, F. Litaudon, M.

Abstract

Three new clerodane-type terpenoids, furocrotinsulolide A (1), furocrotinsulolide B (2), and crotinsulactone (3), as well as a new phenolic disaccharide (4) have been isolated from the aerial parts of Croton insularis, together with eight known compounds. Their structures were established by in-depth 1D- and 2D-NMR spectroscopy, mass spectroscopy, and quantum-mechanical calculations. © 2005 Verlag Helvetica Chimica Acta AG.

Published
2005

41. Koniamborine, the first pyrano[3,2-b]indole alkaloid and other secondary metabolites from Boronella koniambiensis

Author

Grougnet, R. Magiatis, P. Fokialakis, N. Mitaku, S. Skaltsounis, A.-L. Tillequin, F. Sévenet, T. Litaudon, M.

Abstract

Two new alkaloids, (-)-cis-1,2-dihydroxy-1,2-dihydromedicosmine (3) and koniamborine (4), have been isolated from Boronella koniambiensis aerial parts. Their structures have been established from NMR and mass data. Koniamborine is a novel type of alkaloid, which derives from the pyrano[3,2-6]indole basic skeleton, described for the first time from nature. 6-Methoxy-1-methylisatin, also present in the plant material, can be considered biogenetically as a degradation product of the fused pyrone ring of 4. © 2005 American Chemical Society and American Society of Pharmacognosy.

Published
2005

42. New caledonian ARAUCARIACEAE/ Araucaria subalata

Author

M. Sarrailh, J., P. Chauvin, J., Litaudon, M., Dumontet, V., Pieters, R., Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2005

43. New Diterpenes from Croton insularis

Author

Graikou, K. Aligiannis, N. Skaltsounis, A.-L. Chinou, I. Michel, S. Tillequin, F. Litaudon, M.

Abstract

Two new diterpenes (1 and 2) have been isolated from the aerial parts of Croton insularis. Their structures have been established by NMR and mass spectral data, and the absolute configuration of 1 and related trachylobane diterpenes was determined through a series of chemical correlations.

Published
2004

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