IDENTIFICATION AND DETERMINATION OF ALKALOIDS IN FUMARIA SPECIES FROM ROMANIA

in Digest Journal of Nanomaterials and Biostructures (2013), 8(2), 817-824

Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L.

in Phytochemistry (2013), 87

Strychnos nux-vomica L. (Loganiaceae) is famous for its monomeric alkaloid content, such as strychnine, a convulsant poison. The stem bark of the tree is traditionally used to treat intermittent fever in ... [more ▼]

Strychnos nux-vomica L. (Loganiaceae) is famous for its monomeric alkaloid content, such as strychnine, a convulsant poison. The stem bark of the tree is traditionally used to treat intermittent fever in South East Asia. In various studies, it appeared that dimeric indolo-monoterpenic alkaloids possess a promising activity on Plasmodium falciparum. Three bisindolomonoterpenic alkaloids together with strychnochrysine, previously identified in the root bark of S. nux-vomica, were isolated from the stem bark. The structures of these compounds were established using NMR spectroscopy and mass spectrometry. Stereochemistry of the compounds was confirmed by molecular modelling. This then allowed the structural determination of strychnoflavine, a coloured bisindole alkaloid previously isolated from the root bark of the tree. Moreover, the conformational inversion in alkaloids possessing an ether bond in the strychnane moiety could be easily predicted by specific δ 13C NMR values. These longicaudatine-type alkaloids were found to display in vitro antiplasmodial activity against a chloroquine resistant strain and a chloroquine sensitive strain. The most interesting was strychnochrysine showing an IC 50 value at around 10 μM. © 2012 Elsevier Ltd. All rights reserved. [less ▲]

Bisindolomonoterpenic alkaloids from the stem bark of Strychnos nux-vomica exhibiting antiplasmodial activity

in Planta Medica (2012, August), 78(11), 1047

Anti-plasmodial activity of Dicoma tomentosa (Asteraceae) and identification of urospermal A-15- O-acetate as the main active compound.

in Malaria Journal (2012), 11(1), 2891-9

ABSTRACT: BACKGROUND: Natural products could play an important role in the challenge to discover new anti-malarial drugs. In a previous study, Dicoma tomentosa (Asteraceae) was selected for its promising ... [more ▼]

ABSTRACT: BACKGROUND: Natural products could play an important role in the challenge to discover new anti-malarial drugs. In a previous study, Dicoma tomentosa (Asteraceae) was selected for its promising anti-plasmodial activity after a preliminary screening of several plants traditionally used in Burkina Faso to treat malaria. The aim of the present study was to further investigate the antiplasmodial properties of this plant and to isolate the active anti-plasmodial compounds. METHODS: Eight crude extracts obtained from D. tomentosa whole plant were tested in vitro against two Plasmodium falciparum strains (3D7 and W2) using the p-LDH assay (colorimetric method). The Peters' four-days suppressive test model (Plasmodium berghei-infected mice) was used to evaluate the in vivo anti-plasmodial activity. An in vitro bioguided fractionation was undertaken on a dichloromethane extract, using preparative HPLC and TLC techniques. The identity of the pure compound was assessed using UV, MS and NMR spectroscopic analysis. In vitro cytotoxicity against WI38 human fibroblasts (WST-1 assay) and haemolytic activity were also evaluated for extracts and pure compounds in order to check selectivity. RESULTS: The best in vitro anti-plasmodial results were obtained with the dichloromethane, diethylether, ethylacetate and methanol extracts, which exhibited a high activity (IC50 [less than or equal to] 5 mug/ml). Hot water and hydroethanolic extracts also showed a good activity (IC50 [less than or equal to] 15 mug/ml), which confirmed the traditional use and the promising anti-malarial potential of the plant. The activity was also confirmed in vivo for all tested extracts. However, most of the active extracts also exhibited cytotoxic activity, but no extract was found to display any haemolytic activity. The bioguided fractionation process allowed to isolate and identify a sesquiterpene lactone (urospermal A-15-O-acetate) as the major anti-plasmodial compound of the plant (IC50 < 1 mug/ml against both 3D7 and W2 strains). This was also found to be the main cytotoxic compound (SI =3.3). While this melampolide has already been described in the plant, this paper is the first report on the biological properties of this compound. CONCLUSIONS: The present study highlighted the very promising anti-plasmodial activity of D. tomentosa and enabled to identify its main active compound, urospermal A-15-O-acetate. The high antiplasmodial activity of this compound merits further study about its anti-plasmodial mechanism of action. The active extracts of D. tomentosa, as well as urospermal A 15-Oacetate, displayed only a moderate selectivity, and further studies are needed to assess the safety of the use of the plant by the local population. [less ▲]

Les Huiles Essentielles et l'Aromathérapie

Learning material (2012)

Polyphenol Content and Modulatory Activities of Some Tropical Dietary Plant Extracts on the Oxidant Activities of Neutrophils and Myeloperoxidase

in International Journal of Molecular Sciences (2012), 13(1), 628-650

LC–SPE–NMR–MS analysis of Strychnos usambarensis fruits from Rwanda

in Phytochemistry Letters (2012), 5(0), 170-173

The novelty of the present work lies in the characterization of akagerine and palicoside in Strychnos usambarensis fruits by a hyphenated analytical method combining high-performance liquid chromatography ... [more ▼]

The novelty of the present work lies in the characterization of akagerine and palicoside in Strychnos usambarensis fruits by a hyphenated analytical method combining high-performance liquid chromatography coupled with solid-phase extraction (SPE), mass spectrometry (HPLC–MS) and NMR spectroscopy. Akagerine was already known in S. usambarensis roots but palicoside is described for the first time in the species. [less ▲]

17-O-Actetyl-10-hydroxycorynantheol, a selective antiplasmodial alkaloid isolated from Strychnos usambarensis leaves

Conference (2011, December 13)

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary ... [more ▼]

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary indolic alkaloid has been isolated: 17-O-acetyl, 10-hydroxycorynantheol 1. Its structure was determined by means of spectroscopic and spectrometric methods such as UV, IR, CD, NMR and ESI-MS. 17-O-acetyl, 10-hydroxycorynantheol 1 is one of the most active monomeric indole alkaloid known to date showing an in vitro activity against Plasmodium falciparum close to 5 µM and a high selectivity. [less ▲]

Evaluation of the antioxidant activity of passion fruit (Passiflora edulis and Passiflora alata) extracts on stimulated neutrophils and myeloperoxidase activity assays

in Food Chemistry (2011), 128

17-O-acetyl, 10-hydroxycorynantheol, a selective antiplasmodial alkaloid isolated from Strychnos usambarensis leaves

Conference (2011, May 13)

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary ... [more ▼]

In the course of our investigations on Strychnos usambarensis leaves in order to isolate isostrychnopentamine, the main alkaloid responsible for the antiplasmodial activity of the plant, a new tertiary indolic alkaloid has been isolated: 17-O-acetyl, 10-hydroxycorynantheol 1. Its structure was determined by means of spectroscopic and spectrometric methods such as UV, IR, CD, NMR and ESI-MS. 17-O-acetyl, 10-hydroxycorynantheol 1 is one of the most active monomeric indole alkaloid known to date showing an in vitro activity against Plasmodium falciparum close to 5 µM and a high selectivity. [less ▲]