Éditeur(s) : HAL CCSD American Mosquito Control Association
Résumé : Research on natural insecticides has intensified with the spread of resistance to chemicals among insects, particularly disease vectors. To evaluate compounds, the World Health Organization (WHO) has published standardized procedures. However, those may be excessively compound-consuming when it comes to assessing the activity of natural extracts and pure compounds isolated in limited amount. As part of our work on the discovery of new mosquito larvicides from Amazonian plants, we developed a compound-saving assay in 5-ml glass tubes instead of WHO larval 100-m1 cups. Comparing activity of synthetic and natural chemicals validated the glass tube assay. Raw data, lethal doses that kill 50% (LD50) and 90% (LD90) at 24 and 48 h, were highly correlated (0.68 < R-2 < 0.96, P < 0.001, Pearson test) between cups and tubes. It was also established that 10 tubes (N = 50 larvae) provided the same level of sensitivity as 20 tubes (N= 100). This method proved suitable for rapid screening of natural extracts and molecules, identifying active compounds using 10 times less material than in the WHO protocol.
ISSN: 8756-971X

hal-01602207
https://hal.archives-ouvertes.fr/hal-01602207
DOI : 10.2987/16-6613.1
PRODINRA : 394297
PUBMED : 28206865

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
ISSN: 1874-3900

hal-01152699
https://hal.archives-ouvertes.fr/hal-01152699
DOI : 10.1016/j.phytol.2015.03.012

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
In French Guiana, Quassia amara L. (Simaroubaceae) leaf tea is a well-known widely used traditional antimalarial remedy. Impact of the vegetal sampling condition on in vivo and in vitro antimalarial activity was assessed. Traditional infusions were prepared with juvenile or mature leaves, both either fresh or dried. Results showed that growing stage and freshness of vegetal material exert a striking effect on antimalarial activity, both in vitro and in vivo. By far, leaf tea made from fresh juvenile (FJ) Quassia amara leaves was the most active. In vitro, active component (simalikalactone D) concentration correlates biological activities, although unexplained subtle variations were observed. In vivo, tea made with dried juvenile (DJ) leaves displays a peculiar behavior, meaning that some components may help simalikalactone D delivery or may be active in vivo only, therefore enhancing the expected curative effect of the traditional preparation.
ISSN: 0378-8741

hal-00384338
https://hal.archives-ouvertes.fr/hal-00384338
DOI : 10.1016/j.jep.2006.10.028

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
Ethnopharmacological relevancePsidium acutangulum Mart. ex DC is a small tree used by the Wayana Amerindians from the Upper-Maroni in French Guiana for the treatment of malaria.Aim of the studyIn a previous study, we highlighted the in vitro antiplasmodial, antioxidant and anti-inflammatory potential of the traditional decoction of P. acutangulum aerial parts. Our goal was then to investigate on the origin of the biological activity of the traditional remedy, and eventually characterize active constituents.Materials and methodsLiquid-liquid extractions were performed on the decoction, and the antiplasmodial activity evaluated against chloroquine-resistant FcB1 ([3H]-hypoxanthine bioassay) and 7G8 (pLDH bioassay) P. falciparum strains, and on a chloroquine sensitive NF54 ([3H]-hypoxanthine bioassay) P. falciparum strain. The ethyl acetate fraction (D) was active and underwent bioguided fractionation. All the isolated compounds were tested on P. falciparum FcB1 strain. In vitro anti-inflammatory activity (IL-1β, IL-6, IL-8, TNFα) of the ethyl acetate fraction and of an anti-Plasmodium active compound, was concurrently assessed on LPS-stimulated human PBMC and NO secretion inhibition was measured on LPS stimulated RAW murine macrophages. Cytotoxicity of the fractions and pure compounds was measured on VERO cells, L6 mammalian cells, PBMCs, and RAW cells.ResultsFractionation of the ethyl acetate soluble fraction (IC50 ranging from 3.4 to <1 µg/mL depending on the parasite strain) led to the isolation of six pure compounds: catechin and five glycosylated quercetin derivatives. These compounds have never been isolated from this plant species. Two of these compounds (wayanin and guaijaverin) were found to be moderately active against P. falciparum FcB1 in vitro (IC50 5.5 and 6.9 µM respectively). We proposed the name wayanin during public meetings organized in June 2015 in the Upper-Maroni villages, in homage to the medicinal knowledge of the Wayana population. At 50 µg/mL, the ethyl acetate fraction (D) significantly inhibited IL-1β secretion (−46%) and NO production (−21%), as previously observed for the decoction. The effects of D and guiajaverin (4) on the secretion of other cytokines or NO production were not significant.ConclusionsThe confirmed antiplasmodial activity of the ethyl acetate soluble fraction of the decoction and of the isolated compounds support the previous results obtained on the P. acutangulum decoction. The antiplasmodial activity might be due to a mixture of moderately active non-toxic flavonoids. The anti-inflammatory activities were less marked for ethyl acetate fraction (D) than for the decoction.
ISSN: 0378-8741

hal-01313006
http://hal.upmc.fr/hal-01313006
http://hal.upmc.fr/hal-01313006/document
http://hal.upmc.fr/hal-01313006/file/Houel_Wayanin_and.pdf
DOI : 10.1016/j.jep.2016.04.053

Éditeur(s) : HAL CCSD Instituto Oswaldo Cruz, Ministério da Saúde
Résumé : International audience
This study examined whether the antidermatophytic activity of essential oils (EOs) can be used as an indicator for the discovery of active natural products against Leishmania amazonensis. The aerial parts of seven plants were hydro-distilled. Using broth microdilution techniques, the obtained EOs were tested against three strains of dermatophytes (Trichophyton mentagrophytes, Microsporum gypseum and Microsporum canis). To compare the EOs antifungal and antiparasitic effects, the EOs activities against axenic amastigotes of L. amazonensis were concurrently evaluated. For the most promising EOs, their antileishmanial activities against parasites infecting peritoneal macrophages of BALB/c mice were measured. The most interesting antifungal candidates were the EOs from Cymbopogon citratus, Otacanthus azureus and Protium heptaphyllum, whereas O. azureus, Piper hispidum and P. heptaphyllum EOs exhibited the lowest 50% inhibitory concentration (IC 50) values against axenic amastigotes, thus revealing a certain correspondence between both activities. The P. hispidum EO was identified as the most promising product in the results from the infected macrophages model (IC 50 : 4.7 µg/mL, safety index: 8). The most abundant compounds found in this EO were sesquiter-penes, notably curzerene and furanodiene. Eventually, the evaluation of the antidermatophytic activity of EOs appears to be an efficient method for identifying new potential drugs for the treatment of L. amazonensis.
ISSN: 0074-0276

Droits : http://creativecommons.org/licenses/by/
hal-01230471
http://hal.upmc.fr/hal-01230471
http://hal.upmc.fr/hal-01230471/document
http://hal.upmc.fr/hal-01230471/file/0074-0276-mioc-0140332.pdf
DOI : 10.1590/0074-02760140332

Éditeur(s) : HAL CCSD
Résumé : International audience
De la recherche en Guyane - La science par l'exemple

hal-01096923
https://hal-agroparistech.archives-ouvertes.fr/hal-01096923

Éditeur(s) : HAL CCSD American Society for Microbiology
Résumé :  
We report the isolation and identification of a new quassinoid named simalikalactone E (SkE), extracted from a widely used Amazonian antimalarial remedy made out of Quassia amara L. (Simaroubaceae) leaves. This new molecule inhibited the growth of Plasmodium falciparum cultured in vitro by 50%, in the concentration range from 24 to 68 nM, independently of the strain sensitivity to chloroquine. We also showed that this compound was able to decrease gametocytemia with a 50% inhibitory concentration sevenfold lower than that of primaquine. SkE was found to be less toxic than simalikalactone D (SkD), another antimalarial quassinoid from Q. amara, and its cytotoxicity on mammalian cells was dependent on the cell line, displaying a good selectivity index when tested on nontumorogenic cells. In vivo, SkE inhibited murine malaria growth of Plasmodium vinckei petteri by 50% at 1 and 0.5 mg/kg of body weight/day, by the oral or intraperitoneal routes, respectively. The contribution of quassinoids as a source of antimalarial molecules needs therefore to be reconsidered.
ISSN: 0066-4804

hal-01032126
https://hal.archives-ouvertes.fr/hal-01032126
DOI : 10.1128/AAC.00951-09

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
The chemical investigations of Dicorynia guianensis heartwood led to the isolation of four new indole alkaloids for the first time in this plant. Compound (1) identified as spiroindolone 20,30,40,90-tetrahydrospiro [indoline-3,10pyrido[3,4-b]-indol]-2-one, and compound (3) described as nitrone 1-methyl-4,9-dihydro-3H-pyrido [3,4-b] indole 2-oxide and were isolated for the first time as natural products. ABTS antioxidant activity guided their isolation.
ISSN: 1874-3900

hal-01138910
https://hal.archives-ouvertes.fr/hal-01138910
DOI : 10.1016/j.phytol.2015.03

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
Extractives that provide natural resistance to Bagassa guianensis Aubl. heartwood were examined. Soil-bed tests showed that the B. guianensis heartwood resistance was significantly reduced after ethyl acetate extraction, whereas methanol and especially water extractions improved the resistance. The ethyl acetate extract was submitted to a bioguided fractionation, and fractions were tested against one wood-destroying fungal strain (Pycnoporus sanguineus) and two human pathogenic fungal strains (Candida glabrata (yeast) and Trichophyton rubrum (filamentous dermatophyte)). Fraction F7, which exhibited the strongest antifungal activity, was subsequently fractionated by high performance liquid chromatography (HPLC). Six previously described compounds were isolated. Although the two moracins, 6-O-methyl-moracin N (3) and moracin N (4) were the most active against fungal strains with MIC values between 4 and 16 μg ml−1, the isolated compounds showed less or equivalent antifungal activity than the initial fraction. Possible synergism between compounds 3 and 4 and other secondary metabolites have been hypothesized. Our study demonstrated that this extract as a whole might be used as a wood preservation or antimycotic product.
International Biodeterioration and Biodegradation

hal-00694532
https://hal.archives-ouvertes.fr/hal-00694532
DOI : 10.1016/j.ibiod.2011.10.016

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
In order to explain the durability of the Moraceae plant family, phytochemistry of Bagassa guianensis was performed. Ethyl acetate extract was obtained from the heartwood and 18 secondary metabolites were isolated, including 6 moracins [6-O-methyl-moracin M, 6-O-methyl-moracin N and moracin Z; previously identified: moracin M, moracin N and moracin P], 8 stilbenoids [presently identified: ( )-epialboctalol and arachidin 4; previously identified: alboctalol, trans-resveratrol, arachidin 2, trans-oxyresveratrol and artogomezianol], 3 previously identified flavonoids, steppogenin, katuranin and dihydromorin, bsitosterol and resorcinol. Previous studies suggest that stilbenoids are responsible for the natural durability of wood. Our study has determined that B. guianensis is closely related to Morus sp. in phylogeny and should be included in the Moreae sensu stricto tribe of the Moraceae family.
ISSN: 0031-9422

hal-00857200
https://hal.archives-ouvertes.fr/hal-00857200
https://hal.archives-ouvertes.fr/hal-00857200/document
https://hal.archives-ouvertes.fr/hal-00857200/file/Secondary_metabolites_Thibaut_al.pdf
DOI : 10.1016/j.phytochem.2010.06.020

Éditeur(s) : HAL CCSD De Gruyter
Résumé : International audience
Wallaba (Eperua falcata) is a tropical wood which is known to have naturally low swelling characteristics. Samples of wallaba heartwood were subjected to differential solvent extraction. Wood pieces that were extracted with methanol experienced significantly higher swelling after rehydration from oven dry to 96% relative humidity in comparison to non-extracted samples and samples extracted with other solvents. Methanol soluble wallaba heartwood extract was purified by high pressure liquid chromatography and the compounds present were characterised by nuclear magnetic resonance spectroscopy. Methanol extract was found to contain a very high relative proportion of polar compounds which are proposed to bind to the polymeric cell wall by multiple hydrogen bonds restricting the association of water and therefore acting as natural anti-swelling agents.
ISSN: 0018-3830

hal-00856942
https://hal.archives-ouvertes.fr/hal-00856942
https://hal.archives-ouvertes.fr/hal-00856942/document
https://hal.archives-ouvertes.fr/hal-00856942/file/Chemical_extractives_tropical_wood_Royer_al.pdf

Éditeur(s) : HAL CCSD De Gruyter
Résumé : International audience
A comparative study of 9H-pyrido[3,4-b]indole (norharmane) and 1-methyl-9H-pyrido[3,4-b]indole (harmane) as inhibitors for C38 steel corrosion in 1 M HCl solution at 25 °C was carried out. Potentiodynamic polarization and electrochemical impedance spectroscopy (EIS) techniques were applied to study the metal corrosion behavior in the absence and presence of different concentrations of these inhibitors. The OCP as a function of time were also established. Cathodic and anodic polarization curves show that norharmane and harmane are a mixed-type inhibitors. Adsorption of indole derivatives on the C38 steel surface, in 1 M HCl solution, follows the Langmuir adsorption isotherm model. The ΔGads values were calculated and discussed. The potential of zero charge (PZC) of the C38 steel in inhibited solution was studied by the EIS method, and a mechanism for the adsorption process was proposed. Raman spectroscopy confirmed that indole molecules strongly adsorbed onto the steel surface. The electronic properties of indole derivates, obtained using the AM1 semi-empirical quantum chemical approach, were correlated with their experimental efficiencies using the linear resistance model (LR).
ISSN: 0018-3830

hal-01093227
https://hal-agroparistech.archives-ouvertes.fr/hal-01093227
DOI : 10.1515/HF.2010.034

Éditeur(s) : HAL CCSD Wiley Open Access
Résumé : International audience
Plant responses to natural enemies include formation of secondary metabolites acting as direct or indirect defenses. Volatile terpenes represent one of the most diverse groups of secondary metabolites. We aimed to explore evolutionary patterns of volatile terpene emission. We measured the composition of damage-induced volatile terpenes from 202 Amazonian tree species, spanning the angiosperm phylogeny. Volatile terpenes were extracted with solid-phase micro extraction and desorbed in a gas chromatography–mass spectrometry for compound identification. The chemical diversity of the terpene blend showed a strong phylogenetic signal as closely related species emitted a similar number of compounds. Closely related species also tended to have compositionally similar blends, although this relationship was weak. Meanwhile, the ability to emit a given compound showed no significant phylogenetic signal for 200 of 286 compounds, indicating a high rate of diversification in terpene synthesis and/or great variability in their expression. Three lineages (Magnoliales, Laurales, and Sapindales) showed exceptionally high rates of terpene diversification. Of the 70 compounds found in >10% of their species, 69 displayed significant correlated evolution with at least one other compound. These results provide insights into the complex evolutionary history of volatile terpenes in angiosperms, while highlighting the need for further research into this important class of compounds.
ISSN: 2045-7758

Droits : http://creativecommons.org/licenses/by/
hal-01296640
http://hal.upmc.fr/hal-01296640
http://hal.upmc.fr/hal-01296640/document
http://hal.upmc.fr/hal-01296640/file/ece31810.pdf
DOI : 10.1002/ece3.1810

Éditeur(s) : HAL CCSD Taylor & Francis
Résumé : International audience
ISSN: 1028-6020

hal-01095384
https://hal-agroparistech.archives-ouvertes.fr/hal-01095384
DOI : 10.1021/np1001412

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
French Guiana (North-East Amazonia) records high malaria incidence rates. The traditional antimalarial remedy most widespread there is a simple tea made out from Quassia amara L. leaves (Simaroubaceae). This herbal tea displays an excellent antimalarial activity both in vitro and in vivo. A known quassinoid, simalikalactone D (SkD), was identified as the active compound, with an IC50 value of 10nM against FcB1 Plasmodium falciparum chloroquine resistant strain in vitro. Lastly, it inhibits 50% of Plasmodium yoelii yoelii rodent malaria parasite at 3.7 mg/kg/day in vivo by oral route. These findings confirm the traditional use of this herbal tea.
ISSN: 0378-8741

hal-00384337
https://hal.archives-ouvertes.fr/hal-00384337
DOI : 10.1016/j.jep.2006.04.017

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
ISSN: 0378-8741

hal-01087030
https://hal-agroparistech.archives-ouvertes.fr/hal-01087030
DOI : 10.1016/j.jep.2009.07.037

Éditeur(s) : HAL CCSD Springer Verlag
Résumé :  
Volatile organic compounds (VOCs) are produced by a broad range of organisms, from bacteria to mammals, and they represent a vast chemical diversity. In plants, one of the preeminent roles of VOCs is their repellent or cytotoxic activity, which helps the plant deter its predators. Most studies on VOCs emitted by vegetative parts have been conducted in model plant species, and little is known about patterns of VOC emissions in diverse plant communities. We conducted a survey of the VOCs released immediately after mechanical damage of the bark and the leaves of 195 individual trees belonging to 55 tropical tree species in a lowland rainforest of French Guiana. We discovered a remarkably high chemical diversity, with 264 distinct VOCs and a mean of 37 compounds per species. Two monoterpenes (α-pinene and limonene) and two sesquiterpenes (β-caryophyllene and α-copaene), which are known to have cytotoxic and deterrent effects, were the most frequent compounds in the sampled species. As has been established for floral scents, the blend of VOCs is largely species-specific and could be used to discriminate among 43 of the 55 sampled species. The species with the most diverse blends were found in the Sapindales, Laurales, and Magnoliales, indicating that VOC diversity is not uniformly distributed among tropical species. Interspecific variation in chemical diversity was caused mostly by variation in sesquiterpenes. This study emphasizes three aspects of VOC emission by tropical tree species: the species-specificity of the mixtures, the importance of sesquiterpenes, and the wide-ranging complexity of the mixtures.
ISSN: 0098-0331

hal-01032119
https://hal.archives-ouvertes.fr/hal-01032119
DOI : 10.1007/s10886-009-9718-1

Éditeur(s) : HAL CCSD Elsevier
Résumé : International audience
ETHNOPHARMACOLOGICAL RELEVANCE: Cutaneous leishmaniasis is a neglected disease with a high incidence in French Guiana, mainly in the middle and upper Oyapock basin, where Amerindian and some Brazilian people live. The main goals of this work were (i) to assess the knowledge about leishmaniasis in the different populations of the middle and upper Oyapock basin, (ii) to study the therapeutic strategies adopted by people affected by leishmaniasis and (iii) to document the use of phytotherapeutic remedies for leishmaniasis. Knowledge, attitudes and practices (K.A.P.) related to this disease and its treatments have been studied according to cultural group and geographical settlement. Within the Wayãpi group, the evolution of the knowledge of phytoremedies over the last 20 years has been characterised by literature-based comparisons. MATERIALS AND METHODS: A total of 144 questionnaires were administered in all the villages of the upper Oyapock and Camopi basins. Correspondence analyses were used for multivariate analysis. Plant species were identified at the Cayenne Herbarium (CAY). RESULTS: The biomedical concept of leishmaniasis correlates well with the Teko and Wayãpi concepts of kalasapa and kalasapau. Although the vector of this disease was not correctly identified, the most commonly cited aetiology (74.5%) was vector-borne, and related epidemiological schemes correlate well with the one encountered in French Guiana. Theoretically and practically, health centres were the most commonly used resource for diagnostic in instances of leishmaniasis infection (65.9%), independently of the patient's cultural group, along with the use of pharmaceutical drugs (85.3%). Pharmaceuticals were commonly utilised despite the frequent (51.5%) use of phytotherapeutic remedies, alone or in combination with drugs. The most cited medicinal plant species for the treatment of leishmaniasis included Eleutherine bulbosa (Mill.) Urb. (Iridaceae, cited 14 times), Euterpe oleracea Mart. (Arecaceae, 9), Cecropia obtusa Trecul (Cecropiaceae, 8), Jatropha curcas L. (Euphorbiaceae, 7), Ceiba pentandra (L.) Gaertn. (Bombacaceae, 6) and Carica papaya L. (Caricaceae, 6). Multiple correspondence analyses demonstrated that the species used in leishmaniasis remedies are more prone to vary by the user's place of residence than by their cultural origin, which indicates that exchange of knowledge about leishmaniasis remedies has occurred across different cultural groups. Literature-based comparisons between the remedies for leishmaniasis used by the Wayãpi during the 1980s showed a striking evolution, both in terms of diversity of species and number of plants used. The large number of species shared with other Guianese groups argues for intercultural exchange and may explain the majority (57.1%) of the newly used species highlighted in our study. CONCLUSIONS: Leishmaniasis is a well-known disease in the studied area. Phytotherapeutic treatments are still in use, although they are not the main source of remedies, and should undergo pharmacological studies to evaluate their potential therapeutic value.
ISSN: 0378-8741

pasteur-00634597
https://hal-riip.archives-ouvertes.fr/pasteur-00634597
DOI : 10.1016/j.jep.2011.07.044
PUBMED : 21816216

Éditeur(s) : HAL CCSD American Chemical Society
Résumé : Four new sesquiterpene alkaloids (1-4) with a β-dihydroagrofuran skeleton and a new triterpenoid (5) were isolated from an ethyl acetate extract of Maytenus oblongata stems. Their structures were elucidated using 1D and 2D NMR spectroscopy as well as MS and ECD experiments. The M. oblongata stem EtOAc extract and the pure compounds isolated were tested for larvicidal activity against Aedes aegypti under laboratory conditions, and compounds 2 and 3 were found to be active.
ISSN: 0163-3864

hal-01603411
https://hal.archives-ouvertes.fr/hal-01603411
DOI : 10.1021/acs.jnatprod.6b00850
PUBMED : 28186749
PRODINRA : 406747

Éditeur(s) : HAL CCSD Elsevier
Résumé : Volatile terpenes are among the most diverse class of defensive compounds in plants, and they are implicated in both direct and indirect defense against herbivores. In terpenes, both the quantity and the diversity of compounds appear to increase the efficiency of defense as a diverse blend of compounds provides a more efficient protection against a broader range of herbivores and limits the chances that an enemy evolves resistance. Theory predicts that plant defensive compounds should be allocated differentially among tissues according to the value of the tissue, its cost of construction and the herbivore pressure on it. We collected volatile terpenes from bark and leaves of 178 individual tree belonging to 55 angiosperm species in French Guiana and compare the kind, amount, and diversity of compounds in these tissues. We hypothesized that in woody plants, the outermost part of the trunk should hold a more diverse blend of volatile terpenes. Additionally, as herbivore communities associated with the leaves is different to the one associated with the bark, we also hypothesized that terpene blends should be distinct in the bark vs. the leaves of a given species. We found that the mixture of volatile terpenes released by bark is different and more diverse than that released by leaves, both in monoterpenes and sesquiterpenes. This supports our hypothesis and further suggests that the emission of terpenes by the bark should be more important for trunk defense than previously thought. (c) 2012 Elsevier Ltd. All rights reserved.
ISSN: 0031-9422

hal-01032417
https://hal.archives-ouvertes.fr/hal-01032417
DOI : 10.1016/j.phytochem.2012.07.003