Éditeur(s) : HAL CCSD BioMed Central
Résumé : International audience
BACKGROUND: Estrogen receptors (ER) α and β are found in both women and men in many tissues, where they have different functions, including having roles in cell proliferation and differentiation of the reproductive tract. In addition to estradiol (E2), a natural hormone, numerous compounds are able to bind ERs and modulate their activities. Among these compounds, phytoestrogens such as isoflavones, which are found in plants, are promising therapeutics for several pathologies. Glyceollins are second metabolites of isoflavones that are mainly produced in soybean in response to an elicitor. They have potentially therapeutic actions in breast cancer by reducing the proliferation of cancer cells. However, the molecular mechanisms driving these effects remain elusive. METHODS: First, to determine the proliferative or anti-proliferative effects of glyceollins, in vivo and in vitro approaches were used. The length of epithelial duct in mammary gland as well as uterotrophy after treatment by E2 and glyceollins and their effect on proliferation of different breast cell line were assessed. Secondly, the ability of glyceollin to activate ER was assessed by luciferase assay. Finally, to unravel molecular mechanisms involved by glyceollins, transcriptomic analysis was performed on MCF-7 breast cancer cells. RESULTS: In this study, we show that synthetic versions of glyceollin I and II exert anti-proliferative effects in vivo in mouse mammary glands and in vitro in different ER-positive and ER-negative breast cell lines. Using transcriptomic analysis, we produce for the first time an integrated view of gene regulation in response to glyceollins and reveal that these phytochemicals act through at least two major pathways. One pathway involving FOXM1 and ERα is directly linked to proliferation. The other involves the HIF family and reveals that stress is a potential factor in the anti-proliferative effects of glyceollins due to its role in increasing the expression of REDD1, an mTORC1 inhibitor. CONCLUSION: Overall, our study clearly shows that glyceollins exert anti-proliferative effects by reducing the expression of genes encoding cell cycle and mitosis-associated factors and biomarkers overexpressed in cancers and by increasing the expression of growth arrest-related genes. These results reinforce the therapeutic potential of glyceollins for breast cancer.
ISSN: 1478-811X

hal-01560288
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01560288
DOI : 10.1186/s12964-017-0182-1
PUBMED : 28666461

Éditeur(s) : HAL CCSD Public Library of Science
Résumé : International audience
Challenging evaluation of tropical forest biodiversity requires the reporting of taxonomic diversity but also the systematic characterization of wood properties in order to discover new promising species for timber industry. Among wood properties, the dimensional stability is regarded as a major technological characteristic to validate whether a wood species is adapted to commercial uses. Cell structure and organization are known to influence the drying shrinkage making wood density and microfibrils angle markers of choice to predict wood dimensional stability. On the contrary the role of wood extractive content remains unclear. This work focuses on the fast-growing tropical species Bagassa guianensis and we report herein a correlation between heartwood drying shrinkage and extractive content. Chemical extractions and shrinkage experiments were performed on separate wood twin samples to better evaluate correctly how secondary metabolites influence the wood shrinkage behaviour. Extractive content were qualitatively and quantitatively analysed using HPLC and NMR spectroscopy. We found that B guianensis heartwood has a homogeneous low shrinkage along its radius that could not be explained only by its basic density. In fact the low drying shrinkage is correlated to the high extractive content and a corrected model to improve the prediction of wood dimensional stability is presented. Additionally NMR experiments conducted on sapwood and heartwood extracts demonstrate that secondary metabolites biosynthesis occurs in sapwood thus revealing B. guianensis as a Juglans-Type heartwood formation. This work demonstrates that B. guianensis, a fast-growing species associated with high durability and high dimensional stability, is a good candidate for lumber production and commercial purposes.
ISSN: 1932-6203

hal-01392725
https://hal.archives-ouvertes.fr/hal-01392725
https://hal.archives-ouvertes.fr/hal-01392725/document
https://hal.archives-ouvertes.fr/hal-01392725/file/2016_BossuBeaucheneEstevezDuplaisClair_PlosOne_WoodDimentionalStabilityAndSecondaryMetabolites.pdf
DOI : 10.1371/journal.pone.0150777.s005

Éditeur(s) : HAL CCSD National Institute of Environmental Health Sciences
Résumé : International audience
BACKGROUND: Glycol ethers are present in a wide range of occupational and domestic products. Animal studies have suggested that some of them may affect ovarian function. OBJECTIVE: To study the relation between women's exposure to glycol ethers and time to pregnancy. METHODS: Urine from randomly selected women in the PELAGIE mother-child cohort who had samples collected before 19 weeks of gestation was tested to measure eight glycol ether metabolites by chromatography coupled to mass spectrometry. Time to pregnancy was collected at the beginning of the pregnancy by asking women how many months they took to conceive. Associations between metabolite levels and time to pregnancy were estimated in 519 women with complete data using discrete-time Cox proportional hazards models to adjust for potential confounders. RESULTS: Glycol ether metabolites were detected in 6% (for ethoxyacetic acid) to 93% (for phenoxyacetic and butoxyacetic acids) of urine samples. Phenoxyacetic acid was the only metabolite with a statistically significant association with longer time to pregnancy (fecundability OR 0.82; 95% CI: 0.63, 1.06 for the second and third quartile combined; fecundability OR 0.70; 95% CI: 0.52, 0.95 for a fourth-quartile (≥1.38 mg/L) vs. first-quartile concentration (<0.14 mg/L)). This association remained stable after multiple sensitivity analyses. CONCLUSION: Phenoxyacetic acid, which was present in most of the urine samples tested in our study, was associated with increased time to pregnancy. This metabolite and its main parent compound, 2-phenoxyethanol, are plausible causes of decreased fecundability, but may also be surrogates for potential co-exposures frequently present in cosmetics.
ISSN: 0091-6765

hal-00866023
https://hal-univ-rennes1.archives-ouvertes.fr/hal-00866023
https://hal-univ-rennes1.archives-ouvertes.fr/hal-00866023/document
https://hal-univ-rennes1.archives-ouvertes.fr/hal-00866023/file/Urinary_Glycol_Ether-accepted.pdf
DOI : 10.1289/ehp.1206103

Éditeur(s) : HAL CCSD MDPI
Résumé : International audience
Marine ecosystems cover about 70% of the planet surface and are still an underexploited source of useful metabolites. Among microbes, filamentous fungi are captivating organisms used for the production of many chemical classes of secondary metabolites bound to be used in various fields of industrial application. The present study was focused on the collection, isolation, screening and genotyping of pigmented filamentous fungi isolated from tropical marine environments around La Réunion Island, Indian Ocean. About 150 micromycetes were revived and isolated from 14 marine samples (sediments, living corals, coral rubble, sea water and hard substrates) collected in four different locations. Forty-two colored fungal isolates belonging to 16 families, 25 genera and 31 species were further studied depending on their ability to produce pigments and thus subjected to molecular identification. From gene sequence analysis, the most frequently identified colored fungi belong to the widespread Penicillium, Talaromyces and Aspergillus genera in the family Trichocomaceae (11 species), then followed by the family Hypocreaceae (three species). This study demonstrates that marine biotopes in La Réunion Island, Indian Ocean, from coral reefs to underwater slopes of this volcanic island, shelter numerous species of micromycetes, from common or uncommon genera. This unstudied biodiversity comes along with the ability for some fungal marine inhabitants, to produce a range of pigments and hues.
ISSN: 2309-608X

hal-01657071
http://hal.univ-reunion.fr/hal-01657071
http://hal.univ-reunion.fr/hal-01657071/document
http://hal.univ-reunion.fr/hal-01657071/file/14-%20Fouillaud%20et%20al.%2C%20J.%20of%20Fungi%202017.pdf
DOI : 10.3390/jof3030036

Résumé : En raison de la nature symbiotique des micro-organismes endophytes, cette étude visait à étudier l'activité antibactérienne, antifongique et cytotoxique chez les métabolites secondaires des extraits endophytes foliaires de plantes de l'Amazonie brésilienne et du Cerrado. Dans ce travail de thèse 147 micro-organismes cultivables ont été isolés (130 champignons, 3 bactéries e 14 champignons non-identifiés ou inconnus) à partir de 28 plantes (4 espèces collectées au Brésil et 24 en Guyane Française). Tous les micro-organismes furent identifiés par analyse moléculaire des régions spécifiques de l'ADNr en utilisant des techniques de séquençage génomique. Des champignons endophytes de l’ordre des Xylariales furent ceux de plus importante fréquence d’isolation dans cette étude, représentés par 25 isolats. Des extraits bruts à l’AcOEt furent produits à partir de cultures de chaque micro-organisme isolé. Une proportion relative signifiante (23,1%) des extraits démontra une activité sur Candida albicans ATCC 10213, pendant que 4% furent actifs sur Staphylococcus aureus ATCC 29213. Le potentiel cytotoxique des extraits fut évalué pour des lignées cellulaires humaines KB (carcinome cervical utérin), MDA-MB-435 (mélanome), et MRC-5 (fibroblastes de poumon normal), résultant en proportion signifiante avec activité d’inhibition de la prolifération cellulaire (24,4%, 23,1% e 16,3%, respectivement).Dix-huit métabolites secondaires furent isolés et identifiés à partir du fractionnement des extraits bruts de huit endophytes. Dix-sept de ces substances furent déjà décrites précédemment dans la littérature: l’acide piliformique (24) et la griséofulvine (25) isolés à partir de Xylaria cubensis SNB-GCI02; La phomopirone (26), la pyrenocine (27), l’alterpérilenol (28) et la novae-zelandine (29), isolés de Lewia infectoria SNB-GTC2402; 5-métilmelleina (31) et la dihidrosporothrioride (32) isolées à partir de Xylaria sp. SNB-GTC2501; La mycoleptodiscine (34) et la mycoleptodiscine B (35) isolées à partir de Mycoleptodiscus sp. SNB-GTC2304; le mycoepoxidiène (36) et la altiloxina A (37) isolés à partir de Diaporthe pseudomangiferae SNB-GSS10; L’acremonisol (40), le semicochliodinol (41) et le cochliodinol (42) isolés à partir de Chaetomium globosum SNB-GTC2114; la colletofragarone A2 (43) isolée à partir de Colletotrichum sp. SNB-GTC0201; la flavoglaucine (44) isolée à partir de Eurotium rubrum BBS01. Parmi ces substances, la flavoglaucine (44) isolée à partir de E. rubrum BBS01 démontra une activité comparable au contrôle fluconazol en C. albicans (CIM de 4 µg.mL-1). La substance (44) présenta IC50 >10 µM sur cellules normales MRC-5, ce qui en fait un candidat pour des études ultérieures. Dans ce travail, fut identifié pour la première fois l’activité de la colletofragarone A2 (43) isolée à partir de Colletotrichum sp. SNB-GTC0201. La substance inédite nommée pyrrocidine C (30) fut isolée à partir de L. infectoria SNB-GTC2402 et identifiée par des analyses spectroscopiques (Casella et al., 2013). La pyrrocidine C (30) fut active en S. aureus ATCC 10213 (CIM de 2 µg.mL-1) et ne fut pas considérées cytotoxique pour les cellules normales MRC-5 (IC50 >10 µM), démontrant une sélectivité dans l’action antimicrobienne. Ces résultats démontrent la grande diversité des endophytes fongiques chez les plantes de l'Amazonie brésilienne et du Cerrado et la grande chimiodiversité associée aux métabolites secondaires de ces micro-organismes. Des champignons endophytes tropicaux, comme ceux présentés dans cette étude, peuvent apparaître comme une nouvelle source de substances antimicrobiennes et cytotoxiques.
Because of the symbiotic nature of endophytes, this survey aims to investigate the probality of discovering antibacterial, antifungal and cytotoxic activities in secondary metabolites of leaf endophytes isolated from plants of Amazon and Cerrado biomes. In this study, 147 cultivable microorganisms were isolated (130 fungi, 3 bacteria and 14 unidentified or unknown microbes) from 28 plant species (4 species collected in Brazil and 24 in French Guyana). All endophytes were identified by molecular analyses of specific rDNA regions, with genomic sequencing techniques. Fungal endophytes belonging to Xylariales order were the most frequently isolated in this study, represented by 25 isolates. Crude AcOEt extracts were produced from cultures of each isolated endophyte. A significant relative proportion (23,1%) of extracts showed activity in Candida albicans ATCC 10213, while 4% were active in Staphylococcus aureus ATCC 29213. The cytotoxic potencial of the extracts was evaluated for human cell lines KB (uterin cervical carcinome), MDA-MB-435 (melanoma) and MRC-5 (normal lung fibroblasts), and a significant proportion of them showed cellular proliferation inhibition (24,4%, 23,1% e 16,3%, respectively).Eighteen secondary metabolites were isolated by the fractionation of eight endophytic extracts. Seventeen of these substances had already been previously described in the literature: piliformic acid (24) and griseofulvin (25) isolated from Xylaria cubensis SNB-GCI02; phomopiron A (26), pyrenocin A (27), alterperilenol (28) and novae-zelandin A (29) isolated from Lewia infectoria SNB-GTC2402; 5-metilmellein (31) and dihidrosporothriorid (32) isolated from Xylaria sp. SNB-GTC2501; mycoleptodiscin A (34) and mycoleptodiscin B (35) isolated from Mycoleptodiscus sp. SNB-GTC2304; mycoepoxidien (36) and altiloxin A (37) isolated from Diaporthe pseudomangiferae SNB-GSS10; acremonisol A (40), semicochliodinol A (41) and cochliodinol (42) isolated from Chaetomium globosum SNB-GTC2114; colletofragaron A2 (43) isolated from Colletotrichum sp. SNB-GTC0201; flavoglaucin (44) isolated from Eurotium rubrum BBS01. Among these substances, flavoglaucin (44), isolated from E. rubrum BBS01, showed comparable antifungal activity with the positive control fluconazol in C. albicans (MIC of 4 µg.mL-1). Flavoglaucin (44) also showed IC50 >10 µM in normal MRC-5 cells, becoming a good candidate for further studies. In this work, the cytotoxic activity of colletofragaron A2 (43), isolated from Colletotrichum sp. SNB-GTC0201 was described for the first time. The unpublished substance named pyrrocidin C (30) isolated from L. infectoria SNB-GTC2402 was identified by spectroscopic analyses (Casella et al., 2013). The pyrrocidin C (30) was active in S. aureus ATCC 10213 (MIC of 2 µg.mL-1), and was not considered cytotoxic for normal MRC-5 cells (IC50 >10 µM), showing selectivity in antimicrobial activity. These results demonstrate the great endophytic fungal diversity in plants of Amazon and Cerrado biomes, along with the chemodiversity associated to the secondary metabolites of these endophytes. Tropical fungal endophytes, like those seen in this work, may emerge as a new source of antimicrobial and cytotoxic substances.
Devido à natureza simbiótica dos micro-organismos endofíticos, este estudo teve como objetivo investigar a atividade antibacteriana, antifúngica e citotóxica em metabólitos secundários de extratos de fungos endofíticos foliares de plantas do bioma Amazônia e Cerrado. Neste trabalho de tese foram isolados 147 micro-organismos cultiváveis (130 fungos, 3 bactérias e 14 fungos não-identificados ou desconhecidos) a partir de 28 plantas (4 espécies coletadas no Brasil e 24 na Guiana Francesa). Todos os micro-organismos foram identificados por análise molecular de regiões específicas de DNAr, com uso de técnicas de sequenciamento genômico. Fungos endofíticos da ordem Xylariales foram os de maior frequência de isolamento neste estudo, representados por 25 isolados. Extratos brutos em AcOEt foram produzidos a partir de culturas de cada micro-organismo isolado. Uma proporção relativa significante (23,1%) dos extratos demonstrou atividade em Candida albicans ATCC 10213, enquanto 4% foram ativos em Staphylococcus aureus ATCC 29213. O potencial citotóxico dos extratos foi avaliado para as linhagens celulares humanas KB (carcinoma cervical uterino), MDA-MB-435 (melanoma), e MRC-5 (fibroblastos de pulmão normal), resultando em proporção significante com atividade de inibição da proliferação celular (24,4%, 23,1% e 16,3%, respectivamente). Dezoito metabólitos secundários foram isolados a partir do fracionamento de oito extratos brutos endofíticos. Dezessete destas substâncias já tinham sido descritas anteriormente na literatura: ácido pilifórmico (24) e griseofulvina (25) isoladas de Xylaria cubensis SNB-GCI02; phomopirona A (26), pyrenocina A (27), alterperilenol (28) e novae-zelandina A (29) isoladas de Lewia infectoria SNB-GTC2402; 5-metilmelleina (31) e Dihidrosporothriolida (32) isoladas de Xylaria sp. SNB-GTC2501; mycoleptodiscina A (34) e mycoleptodiscina B (35) isoladas de Mycoleptodiscus sp. SNB-GTC2304; mycoepoxidieno (36) e altiloxina A (37) isoladas de Diaporthe pseudomangiferae SNB-GSS10; acremonisol A (40), semicochliodinol A (41) e cochliodinol (42) isoladas de Chaetomium globosum SNB-GTC2114; colletofragarona A2 (43) isolada de Colletotrichum sp. SNB-GTC0201; flavoglaucina (44) isolada de Eurotium rubrum BBS01. Dentre estas substâncias, a flavoglaucina (44) isolada de E. rubrum BBS01, demonstrou atividade comparável ao controle fluconazol em C. albicans (CIM de 4 µg.mL-1). Esta substância (44) apresentou IC50 >10 µM em células normais MRC-5, tornando-se candidata para estudos posteriores. Neste trabalho foi identificado pela primeira vez a atividade citotóxica da colletofragarona A2 (43), isolada de Colletotrichum sp. SNB-GTC0201. A substância inédita nomeada pyrrocidina C (30) foi isolada a partir de L. infectoria SNB-GTC2402 e identificada através de análises espectroscópicas (Casella et al., 2013). A pyrrocidina C (30) foi ativa em S. aureus ATCC 10213 (CIM de 2 µg.mL-1), e não foi considerada citotóxica para as células normais MRC-5 (IC50 >10 µM), demonstrando seletividade na ação antimicrobiana. Estes resultados demonstram a grande diversidade fúngica endofítica em plantas do bioma Amazônia e Cerrado, e a quimiodiversidade associada aos metabólitos secundários destes micro-organismos. Fungos endofíticos tropicais, como os vistos neste trabalho, podem emergir como uma nova fonte de substâncias antimicrobianas e citotóxicas.

http://www.theses.fr/2014AGUY0836/document

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 Royal Society of Chemistry
Résumé : International audience
Chemical mediation regulates behavioral interactions between species and thus affects population structure,community organization and ecosystem function. Among marine taxa that have developed chemicalmediation strategies, gastropods belong to a diverse group of molluscs found worldwide, including specieswith a coiled, reduced or absent shell. Most gastropods use natural products to mediate a wide range ofbehaviors such as defense, prey location or interactions with con- and hetero-geners. Their chemicallydefended diet, such as cyanobacteria, algae, sponges, bryozoans and tunicates, provides them witha considerable opportunity either as shelter from predators, or as a means to enhance their own chemicaldefense. In addition to improving their defenses, molluscs also use prey secondary metabolites in complexchemical communication including settlement induction, prey detection and feeding preferences. Theassimilation of prey secondary metabolites further provides the opportunity for interactions withconspecifics via diet-derived chemical cues or signals. This review intends to provide an overview on thesequestration, detoxification, and biotransformation of diet-derived natural products, as well as the role ofthese compounds as chemical mediators in gastropod-prey interactions.
ISSN: 0265-0568

hal-01563402
https://hal-univ-perp.archives-ouvertes.fr/hal-01563402
DOI : 10.1039/c6np00097e

Éditeur(s) : HAL CCSD Public Library of Science
Résumé : International audience
The hypothalamic-pituitary-adrenal (HPA) axis response to chronic stress is far from straight forward, particularly with regards to animal welfare. There are reports of no effect as well as both decreases and increases in cortisol after chronic stressors. Therefore, the first aim of the present study was to determine how measures of compromised welfare, such as chronic pain and haematological anomalies, related to cortisol levels in domestic horses (Equus caballus). Domestic horses are an informative model to investigate the impact of chronic stress (due to environment, pain, work, housing conditions…) on the HPA axis. The second aim was to determine whether levels of fecal cortisol metabolites (FCM) may be used as an indicator of welfare measures. The present study used fifty-nine horses (44 geldings and 15 mares), from three riding centres in Brittany, France. The primary findings show that horses whose welfare was clearly compromised (as indicated by an unusual ears backward position, presence of vertebral problems or haematological anomalies, e.g. anaemia) also had lower levels of both FCM and plasma cortisol. This work extends our previous findings showing that withdrawn postures, indicators of depressive-like behavior in horses, are associated with lower plasma cortisol levels. We also found that evening plasma cortisol levels positively correlated with FCM levels in horses. Future research aims to determine the extent to which factors of influence on welfare, such as living conditions (e.g. single stalls versus group housing in pasture or paddocks), early life factors, and human interaction, act as mediators of cortisol levels in horses.
ISSN: 1932-6203

hal-01588159
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01588159
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01588159/document
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01588159/file/Pawluski_et_al_-_PLOSONE-2017.pdf
DOI : 10.1371/journal.pone.0182257

Éditeur(s) : HAL CCSD Springer Verlag
Résumé : International audience
The release of polycyclic aromatic hydrocarbons (PAHs) into the environment has increased very substantially over the last decades. PAHs are hydrophobic molecules which can accumulate in high concentrations in sediments acting then as major secondary sources. Fish contamination can occur through contact or residence nearby sediments or though dietary exposure. In this study, we analyzed certain physiological traits in unexposed fish (F1) issued from parents (F0) exposed through diet to three PAH mixtures at similar and environmentally relevant concentrations but differing in their compositions. For each mixture, no morphological differences were observed between concentrations. An increase in locomotor activity was observed in larvae issued from fish exposed to the highest concentration of a pyrolytic (PY) mixture. On the contrary, a decrease in locomotor activity was observed in larvae issued from heavy oil mixture (HO). In the case of the third mixture, light oil (LO), a reduction of the diurnal activity was observed during the setup of larval activity. Behavioral disruptions persisted in F1-PY juveniles and in their offspring (F2). Endocrine disruption was analyzed using cyp19a1b:GFP transgenic line and revealed disruptions in PY and LO offspring. Since no PAH metabolites were dosed in larvae, these findings suggest possible underlying mechanisms such as altered parental signaling molecule and/or hormone transferred in the gametes, eventually leading to early imprinting. Taken together, these results indicate that physiological disruptions are observed in offspring of fish exposed to PAH mixtures through diet.
ISSN: 0944-1344

hal-01121865
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01121865
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01121865/document
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01121865/file/Exposures%20of%20zebrafish_accepted.pdf
DOI : 10.1007/s11356-015-4157-8

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
Résumé : The bacterial microbiota of ants (Hymenoptera: Formicidae) is known to have a defensive role in social insects, particularly for leaf-cutting ants (Formicidae: Attini) due to the use of antimicrobial molecules produced by cuticular actinobacteria. In this thesis, we studied the bacterial microbiota of ants in French Guyana using different approaches based on natural products chemistry and molecular ecology. The first chapter describes the isolation, identification, culture and biological evaluations of 43 cuticular actinobacteria. Antagonism bioassays of isolated strains and antibiotic activities of the culture extracts against human pathogens are presented as well as the identification of an antimicrobial cyclic dipeptide (Cyclo (LPro-LPhe)) isolated from a strain close to Streptomyces thioluteus. Moreover, the implementation of molecular networks applied to UPLC/MS/MS analysis of actinobacterial cocultures allowed us to explore the diversity of metabolites produced under these conditions. The second chapter presents a methodological study to evaluate the capacity of four DNA extraction methods, in terms of richness and composition of the cuticular bacterial microbiota, in high-throughput sequencing from Atta cephalotes and Pseudomyrmex penetrator. The results of metabarcoding highlight two methods of extraction and reveal inter- and intraspecific differences in the composition of cuticular bacterial communities. Finally, chapter three describes the composition of the cuticular bacterial microbiota of Camponotus femoratus and Crematogaster levior in ant garden and the results reveal the acquisition in the environment of a part of the microbiota. In parallel, metabolomic analyses of ant’s cuticle show, on the contrary, a greater specificity related to the ant species. Future researches focusing on statistical analysis strategies combining metabarcoding and metabolomics data are discussed.
Le microbiote bactérien cuticulaire des fourmis (Hymenoptera : Formicidae) est connu pour avoir un rôle défensif chez ces insectes sociaux, notamment chez les fourmis attines (Formicidae : Attini) grâce l’utilisation de molécules antimicrobiennes produites par des actinobactéries cuticulaires. Dans le cadre de cette thèse, nous avons étudié le microbiote bactérien des fourmis de Guyane en utilisant différentes approches en chimie des produits naturels et en écologie moléculaire. Le premier chapitre décrit l’isolement, l’identification, la culture et l’évaluation biologique de 43 actinobactéries cuticulaires de fourmis de Guyane. Les tests d’antagonismes des souches isolées et l’activité antibiotique des extraits de culture contre des micro-organismes pathogènes humains sont présentés ainsi que l’identification d’un dipeptide cyclique (Cyclo(LPro-LPhe)) antimicrobien qui a été isolé à partir d’une souche proche de Streptomyces thioluteus. Par ailleurs, la mise en œuvre de réseaux moléculaires appliqués à une analyse par UPLC/MS/MS de cocultures d’actinobactéries a permis d’explorer la diversité des métabolites produits dans ces conditions. Le deuxième chapitre présente une étude méthodologique pour comparer quatre méthodes d’extraction d’ADN, en termes de richesse et de composition du microbiote bactérien cuticulaire, par séquençage haut débit à partir des espèces Atta cephalotes et Pseudomyrmex penetrator. Les résultats du métabarcoding ADN mettent en lumière deux méthodes d’extraction et révèlent des différences inter- et intraspécifiques dans la composition des communautés bactériennes cuticulaires. Enfin, le chapitre trois décrit la composition du microbiote bactérien cuticulaire des espèces Camponotus femoratus et Crematogaster levior dans les jardins de fourmis. Les résultats soulignent l’acquisition d’une partie du microbiote dans l’environnement. En parallèle l’analyse métabolomique des cuticules montre à contrario une plus grande spécificité liée à l’espèce de fourmi. Les recherches futures axées sur les stratégies d’analyses statistiques combinant le métabarcoding et la métabolomique sont discutées.
https://tel.archives-ouvertes.fr/tel-01537793

NNT : 2017YANE0003
tel-01537793
https://tel.archives-ouvertes.fr/tel-01537793
https://tel.archives-ouvertes.fr/tel-01537793/document
https://tel.archives-ouvertes.fr/tel-01537793/file/thesecarolinebirer.pdf

Éditeur(s) : HAL CCSD Springer Verlag
Résumé : International audience
Fish mucus has important biological and ecologicalroles such as defense against fish pathogens andchemical mediation among several species. A non-targetedliquid chromatography–mass spectrometry metabolomicapproach was developed to study gill mucus of eight butterflyfishspecies in Moorea (French Polynesia), and theinfluence of several fish traits (geographic site and reefhabitat, species taxonomy, phylogeny, diet and parasitismlevels) on the metabolic variability was investigated. Abiphasic extraction yielding two fractions (polar and apolar)was used. Fish diet (obligate corallivorous, facultativecorallivorous or omnivorous) arose as the main driver ofthe metabolic differences in the gill mucus in both fractions,accounting for 23% of the observed metabolic variabilityin the apolar fraction and 13% in the polar fraction.A partial least squares discriminant analysis allowed us toidentify the metabolites (variable important in projection,VIP) driving the differences between fish with differentdiets (obligate corallivores, facultative corallivores andomnivorous). Using accurate mass data and fragmentationdata, we identified some of these VIP as glycerophosphocholines,ceramides and fatty acids. Level of monogeneangill parasites was the second most important factor shapingthe gill mucus metabolome, and it explained 10% of themetabolic variability in the polar fraction and 5% in theapolar fraction. A multiple regression tree revealed that themetabolic variability due to parasitism in the polar fractionwas mainly due to differences between non-parasitized andparasitized fish. Phylogeny and butterflyfish species werefactors contributing significantly to the metabolic variabilityof the apolar fraction (10 and 3%, respectively) buthad a less pronounced effect in the polar fraction. Finally,geographic site and reef habitat of butterflyfish species didnot influence the gill mucus metabolome of butterflyfishes.
ISSN: 0722-4028

hal-01563312
https://hal-univ-perp.archives-ouvertes.fr/hal-01563312
DOI : 10.1007/s00338-017-1554-0

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 : Eperua falcata (Aublet), a late-successional species in tropical rainforest and one of the most abundant tree in French Guiana, has developed an original strategy concerning N-acquisition by largely preferring nitrate, rather than ammonium (H. Schimann, S. Ponton, S. Hattenschwiler, B. Ferry, R. Lensi, A.M. Domenach, J.C. Roggy, Differing nitrogen use strategies of two tropical rainforest tree species in French Guiana: evidence from N-15 natural abundance and microbial activities, Soil Biol, Biochem. 40 (2008) 487-494). Given the preference of this species for nitrate, we hypothesized that root exudates would promote nitrate availability by (a) enhancing nitrate production by stimulating ammonium oxidation or (b) minimizing nitrate losses by inhibiting denitrification. Root exudates were collected in situ in monospecific planted plots. The phytochemical analysis of these exudates and of several of their corresponding root extracts was achieved using UHPLC/DAD/ESI-QTOF and allowed the identification of diverse secondary metabolites belonging to the flavonoid family. Our results show that (i) the distinct exudation patterns observed are related to distinct root morphologies, and this was associated with a shift in the root flavonoid content, (ii) a root extract representative of the diverse compounds detected in roots showed a significant and selective metabolic inhibition of isolated denitrifiers in vitro, and (iii) in soil plots the abundance of nirK-type denitrifiers was negatively affected in rhizosphere soil compared to bulk. Altogether this led us to formulate hypothesis concerning the ecological role of the identified compounds in relation to N-acquisition strategy of this species. (C) 2013 Elsevier Masson SAS. All rights reserved.
ISSN: 0981-9428

hal-01032437
https://hal.archives-ouvertes.fr/hal-01032437
DOI : 10.1016/j.plaphy.2013.05.003

Résumé : Aujourd’hui, il est indispensable de découvrir de nouveaux agents thérapeutiques pour faire face à l’expansion des infections fongiques humaines. D’un autre côté, certains arbres amazoniens ont acquis des moyens pour se protéger contre la dégradation fongique. Ces composés d’origine végétale pourraient donc être des candidats potentiels au développement de composés antifongiques. Il est ainsi exposé dans ce travail la sélection bio-inspirée et la récolte d’espèces d’arbres amazoniens résistants à la dégradation fongique ; à partir desquelles il est proposé d’isoler, d’identifier et de valoriser les métabolites responsables de la durabilité naturelle et d’étudier leurs propriétés sur des champignons pathogènes humains. Cette étude a conduit à l’isolement de molécules inédites apportant un complément d’information chimiotaxonomique pour les espèces étudiées. De plus, il a pu être mis en avant deux molécules pouvant devenir des composés pertinents pour le développement de traitements antimycotiques.
It is now essential to discover new therapeutic agents against the increase of human fungal infections. On the other hand, some Amazonian trees have succeeded to develop a chemical defense arsenal to protect themselves against fungal degradation. These compounds of plant origin could become potential candidates for the development of antifungal compounds for the treatment of human fungal diseases. Therefore, this manuscript describes the bio-inspired selection and collection of Amazonian tree species capable of specializing a highly fungiresistant wood; from which it is proposed to isolate, identify and valorize the secondary metabolites responsible for the natural durability, and study their properties on human pathogenic fungi. Ultimately, this study led to the isolation of new compounds and providing additional important chemotaxonomic information for the species studied. In addition, it as been established that two compounds could be relevant for the development of antimitotic therapies.

http://www.theses.fr/2011AGUY0467/document

Éditeur(s) : HAL CCSD Wiley
Résumé : International audience
Sponges are a rich source for investigation of bioactive small molecules. They have been mostly investigated for the search of new pharmacological models or therapeutic agents for the treatment of human diseases. Micro-organisms can also represent a virulent pathogen for marine invertebrates such as sponges, which need to protect themselves against these microbes. Sponges' self defence mechanisms involving dialogue molecules thus represent a pertinent research track for potent anti-infective and anti-biofilm activities such as quorum sensing inhibitors (QSIs). The investigation of the QSI crude extract of Leucetta chagosensis Dendy, 1863 led to the isolation of three new alkaloids, isonaamine D, di-isonaamidine A and leucettamine D, along with the known isonaamine A and isonaamidine A. Isonaamidine A and isonaamine D were identified as inhibitors of the three quorum sensing pathways of Vibrio harveyi (CAI-1, AI-2 and harveyi auto inducer), but isonaamidine A displayed the strongest activity on AI-2 biosensor. Both compounds are new examples of natural QSIs of V. harveyi. These results outline the importance of these secondary metabolites for their producing organisms themselves in their natural environment, as well as the potential of the marine resource for aquaculture needs.
ISSN: 0266-8254

hal-01684926
https://hal.archives-ouvertes.fr/hal-01684926
DOI : 10.1111/lam.12461
PUBMED : 26138555

Résumé : Dans le cadre de la promotion de systèmes de culture alternatifs à moindres intrants chimiques, des études sur l'introduction de plantes de service ayant vocation à réduire l'usage des pesticides et engrais azotés mobilisent un effort de recherche considérable. Dans le cadre de la production bananière pour laquelle la nuisibilité causée par les nématodes phytoparasites constitue l'une des principales contraintes, une des principales alternatives à l'utilisation de nématicides chimiques repose sur l'usage raisonné en rotation ou en association culturale de plantes de service à propriétés nématorégulatrices. Parmi les espèces candidates, celles du genre Crota/aria spp. ont largement été étudiées en raison de leur aptitude à contrôler les nématodes phytoparasites. Une méta-analyse révèle cependant que même si de nombreux auteurs s'accordent à reconnaître les propriétés allélopathiques des plantes de cette espèce, ils sont également enclins à reconnaître la forte variabilité d'expression de ces propriétés vis-à-vis du contrôle des nématodes selon les situations expérimentées. L'objectif de ce travail repose sur la compréhension du déterminisme biochimique des exsudats. La stratégie expérimentale mise en oeuvre a consisté à tester en conditions contrôlées le comportement biochimique des exsudats racinaires de deux espèces de crotalaires (C retusa, C spectabilis) et d'une espèce sensible, le bananier dessert (Musa spp.) en fonction i) de conditions biotiques variées -i.e. présence ou non de nématodes (Radopholus similis et Meloidogyne arenariaï, et présence ou non de mycorhizes-, ii) de conditions abiotiques contrastées -i.e. utilisation d'un sol naturel vs. substrat neutre, ajout ou non d'engrais chimique. La méthodologie innovante des «plantes à traire » (Brevet INRA) a été requise pour pouvoir travailler sur les exsudats racinaires des plantes conditionnées plutôt que sur des Iixiviats, comme réalisé dans des expérimentations antérieures.Les résultats obtenus en spectrophométrie visible montrent que la modification des conditions abiotiques affecte de manière importante les profils biochimiques des plantes étudiées. En présence du nématode 1..·1. arenaria les profils biochimiques des deux crotalaires sont également modifiés. Des biotests réalisés à l'aide des exsudats racinaires conditionnés au préalable par les modifications biotiques ont permis de démontrer l'effet nématostatique des crotalaires. Des analyses biochimiques en Ge-MS mettent en évidence de manière plus précise des molécules actives mises en jeu sous différentes modalités biotiques et abiotiques. Ces recherches, de portée générique, permettront de mieux comprendre les conditions de l'environnement qui régulent les profils biochimiques des exsudats racinaires des crotalaires et par extension, seront applicables aux recherches menées sur d'autres plantes de service candidates. Ceci aidera, à terme, à définir les conditions environnementales à réunir, pour orienter de manière optimale les effets allélopathiques dans une perspective de nématorégulation naturelle
As part of the promotion of alternative cropping systems at lower chemical inputs, studies on the introduction of cover crops designed to reduce the use of pesticides and nitrogen fertilizers mobilize a considerable research effort. Under banana production for which the hannfu1ness caused by plant-parasitic-nematodes is one ofthe main constraints, one of the main alternatives to the use ofchemical nematicides is based on the rational use in rotation or intercropping of cover rI crops to proteet crops from plant-parasitic-nematodes, Among the candidate species, the species from the genus of Crota/aria spp. have been widely studied because of their ability to control plant parasitic-nematodes. A meta-analysis reveals that although many authors agree allelopathic properties of these species, they are also likely to recognize the high variability of expression of these properties vis-àvis the control of nematodes according to the situations experieaced.. The objective of this woIk is focnsed on the onderstanding of the biochemical determinism of mot exudates onder environment biotic and abiotic variations. The experimental strategy was 10 test onder controlled conditions the biochemical behavior of mot exudates of two species of crotalarias (C retusa, C. spectabilis) and a susceptible species, the dessert banana crop (Musa spp.) with i) modification ofbiotic conditions -ie presence or absence of nematodes iMeloidogyne arenaria and Radopho/us similis), and presence or absence of mycorrhiza-ii) contrasting abiotic conditions -ie using a natural soil vs. neutral substrate, whether to add fertilizer. The innovative methodology of "milking plants" (patent INRA) was required in order to work on the root exudates of plants packed rather thanleachate, as done in previous experiments. The results obtained show that 'visible spectrophotometry changing abiotic conditions affect significantly the biochemical profiles of the studied plants. In the presence of nematode M. arenaria biochemical profiles of both crotalarias are also changed. Bioassays conducted using mot exudates conditioned in advance by biotic changes have demonstrated the effect of nématostatique crotalarias. Biochemical Ge-MS demonstrate more clearly active molecules that are involved in varions biotic and abiotic conditions. This research, generic scope, to better understand the environmental conditions that regulate biochemical profiles of mot exudates crotalarias and by extension, will apply to research on other plants service candidates. This will ultimately define the environmental conditions to meet, to guide optimal allelopathic effects from the perspective ofnatural nématorégulation

http://www.theses.fr/2012AGUY0561/document

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