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Phytochemistry. 2015 Jan;109:84-95. doi: 10.1016/j.phytochem.2014.10.026. Epub 2014 Nov 8.

Indole alkaloids from the Marquesan plant Rauvolfia nukuhivensis and their effects on ion channels.

Author information

1
Laboratoire EIMS UMR 241 EIO, Université de la Polynésie française, BP 6570, 98702 Faa'a, Tahiti, French Polynesia. Electronic address: nicolas.martin1@hotmail.fr.
2
Departamento de Farmacología, Facultad de Veterinaria, Universidad de Santiago de Compostela, Lugo, Spain. Electronic address: sara.fernandez.ferreiro@usc.es.
3
Laboratoire ITODYS UMR CNRS 7086, Université Paris Diderot, Sorbonne Paris Cité, 15 rue J.-A. de Baïf, 75013 Paris, France. Electronic address: florent.barbault@univ-paris-diderot.fr.
4
Laboratoire EIMS UMR 241 EIO, Université de la Polynésie française, BP 6570, 98702 Faa'a, Tahiti, French Polynesia. Electronic address: mael.nicolas@upf.pf.
5
Université de Versailles Saint Quentin en Yvelines, 55 Avenue des Etats-Unis, 78035 Versailles Cedex, France; Laboratoire d'Excellence "CORAIL" - Centre de Recherches Insulaires et Observatoire de l'Environnement (CRIOBE), BP 1013 - 98729, Papetoai, Moorea, French Polynesia. Electronic address: gael.lecellier@uvsq.fr.
6
MPI for Chemical Ecology, Hans-Knöll-Strasse 8, 07745 Jena, Germany. Electronic address: paetz@ice.mpg.de.
7
Institut de Chimie de Nice-PCRE, UMR 7272 CNRS, Université de Nice-Sophia Antipolis, Parc Valrose, 06108 Nice, France. Electronic address: Marc.gaysinski@unice.fr.
8
Departamento de Farmacología, Facultad de Veterinaria, Universidad de Santiago de Compostela, Lugo, Spain. Electronic address: eva.alonso@usc.es.
9
Institut de Chimie de Nice-PCRE, UMR 7272 CNRS, Université de Nice-Sophia Antipolis, Parc Valrose, 06108 Nice, France; Institut Méditerranéen de Biodiversité et d́Ecologie marine et continentale, UMR 7263 CNRS - IRD - Aix-Marseille Université - UAPV, Station Marine d́Endoume, Rue de la Batterie des Lions, 13007 Marseille, France. Electronic address: olivier.thomas@unice.fr.
10
Departamento de Farmacología, Facultad de Veterinaria, Universidad de Santiago de Compostela, Lugo, Spain. Electronic address: luis.botana@usc.es.
11
Laboratoire EIMS UMR 241 EIO, Université de la Polynésie française, BP 6570, 98702 Faa'a, Tahiti, French Polynesia. Electronic address: phila.raharivelomanana@upf.pf.

Abstract

In addition to the already reported nukuhivensiums 1 and 2, 11 indole alkaloids were isolated from the bark of the plant Rauvolfia nukuhivensis, growing in the Marquesas archipelago. The known sandwicine (3), isosandwicine (4), spegatrine (8), lochneram (9), flavopereirine (13) have been found in this plant together with the norsandwicine (5), isonorsandwicine (6), Nb-methylisosandwicine (7), 10-methoxypanarine (10), nortueiaoine (11), tueiaoine (12). The structure elucidation was performed on the basis of a deep exploration of the NMR and HRESIMS data as well as comparison with literature data for similar compounds. Norsandwicine, 10-methoxypanarine, tueiaoine, and more importantly nukuhivensiums, were shown to significantly induce a reduction of IKr amplitude (HERG current). Molecular modelling through docking was performed in order to illustrate this result.

KEYWORDS:

Apocynaceae; Docking calculation; HERG channel activity inhibition; Indole alkaloids; Macroline; Rauvolfia nukuhivensis; Sandwicine; Tueiaoine

PMID:
25468537
DOI:
10.1016/j.phytochem.2014.10.026
[Indexed for MEDLINE]

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