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
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 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 American Chemical Society
Résumé : International audience
Four bicyclic and three pentacyclic guanidine alkaloids (1–7) were isolated from a French Polynesian Monanchora n. sp. sponge, along with the known alkaloids monalidine A (8), enantiomers 9–11 of known natural product crambescins, and the known crambescidins 12–15. Structures were assigned by spectroscopic data interpretation. The relative and absolute configurations of the alkaloids were established by analysis of 1H NMR and NOESY spectra and by circular dichroism analysis. The new norcrambescidic acid (7) corresponds to interesting biosynthetic variation within the pentacyclic core. All compounds exhibited antiproliferative and cytotoxic efficacy against KB, HCT116, HL60, MRC5, and B16F10 cancer cells, with IC50 values ranging from 4 nM to 10 μM.
ISSN: 0163-3864

hal-01584556
https://hal.archives-ouvertes.fr/hal-01584556
DOI : 10.1021/acs.jnatprod.6b00168

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 Elsevier
Résumé : International audience
Aim of the study: A knowledge attitude and practice study centred on leishmaniasis and its treatment was performed among the Chayahuita, an Amazonian Peruvian ethnic group living in an endemic area. This study documents traditional Chayahuita plant's use and disease concepts. Also, activty of some medicinal plants used by the Chayahuita is highlighted and discussed. Materials and methods: Ninety-three Chayahuita people were interviewed, following a semi-structured questionnaire focussed on disease knowledge and perception, personal attitude and healing practices. Simultaneously, a collection of plants was performed in different ecotopes, in order to make an extensive inventory of the pharmacopoeia. Results: For the Chayahuita, cutaneous (CL) and muco-cutaneous leishmaniasis (MCL) are considered as diseases of their own, with specific names, aetiologies, mode of transmission. Regarding CL, Chayahuita people consider that the humid characteristic of the skin ulcer is a discriminative fact orienting the diagnostic forTa'ta' (leishmaniasis). Forty-six different species were designated useful against LC and /or MCL (29 species by means of the questionnaire and 27 species when collecting in different ecotopes). Thirty-seven extracts corresponding to 31 species used medicinally were screened in vitro against Leishmania amnzonensis axenic amastigotes, assessing their viability by the reduction of tetrazolium salt (MTT). Six species displayed a good activity ( 10 μg/ml < IC50 < 20 μg/ml): an undetermined hemi-epiphytic Clusiaceae, Cyhianthus anthuriophyllus Pipoly (Myrsinaceae), two Piper, Piper sanguineispicum Trel., and Piper loretoanum Trel. (Piperaceae), Desmodium axillare Sw. DC. (Fabaceae), and Clibadium sylvestre (Aubl.) Baill. (Asteraceae). Conclusion: Perception of leishmaniasis, attitude, treatments and diet prohibitions still largely reflects traditional Chayahuita cosmovision, even if some tentative of bio-medical re-interpretation is arising.
ISSN: 0378-8741

hal-01087667
https://hal-agroparistech.archives-ouvertes.fr/hal-01087667
DOI : 10.1016/j.jep.2009.07.015

Éditeur(s) : HAL CCSD Maney Publishing
Résumé : International audience
ISSN: 1478-422X

hal-01082607
https://hal-agroparistech.archives-ouvertes.fr/hal-01082607
DOI : 10.1016/j.corsci.2008.04.019

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

hal-01082177
https://hal-agroparistech.archives-ouvertes.fr/hal-01082177
DOI : 10.1016/j.jep.2006.09.045

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 Elsevier
Résumé : Ethnopharmacological relevance: Cutaneous and mucocutaneous leishmaniasis are neglected tropical diseases that occur in all intertropical regions of the world. Amazonian populations have developed an abundant knowledge of the disease and its remedies. Therefore, we undertook to review traditional antileishmanial plants in Amazonia and have developed new tools to analyze this somewhat dispersed information.Material and methods: A literature review of traditional remedies for cutaneous/mucocutaneous leishmaniasis in the Amazon was conducted and the data obtained was used to calculate distribution indexes designed to highlight the most relevant uses in Amazonia. The cultural distribution index represents the distribution rate of a given taxon among different cultural groups and was calculated as the ratio of the number of groups using the taxon to the total number of groups cited. The geographical distribution index allowed us to quantify spatial distribution of a taxon's uses in Amazonia and was calculated geometrically by measuring the average distance between the points where uses have been reported and the barycenter of those points. The general distribution index was defined as an arithmetic combination of the previous two and provides information on both cultural and spatial criteria.Results: 475 use reports, concerning 291 botanical species belonging to 83 families have been gathered depicted from 29 sources. Uses concern 34 cultural groups. While the use of some taxa appears to be Pan Amazonian, some others are clearly restricted to small geographical regions. Particular attention has been paid to the recipes and beliefs surrounding treatments. Topical application of the remedies dominated the other means of administration and this deserves particular attention as the main treatments against Neotropical leishmaniasis are painful systemic injections. The data set was analyzed using the previously defined distribution indexes and the most relevant taxa were further discussed from a phytochemical and pharmacological point of view.Conclusions: The Amazonian biodiversity and cultural heritage host a fantastic amount of data whose systematic investigation should allow a better large-scale understanding of the dynamics of traditional therapies and the consequent discovery of therapeutic solutions for neglected diseases. Distribution indices are indeed powerful tools for emphasizing the most relevant treatments against a given disease and should be very useful in the meta-analysis of other regional pharmacopeia. This focus on renowned remedies that have not yet benefitted from extended laboratory studies, could stimulate future research on new treatments of natural origin for leishmaniasis.
ISSN: 0378-8741

hal-01603285
https://hal.archives-ouvertes.fr/hal-01603285
DOI : 10.1016/j.jep.2017.01.048
PRODINRA : 401890

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