151 research outputs found

    Computer Aided Aroma Design. II. Quantitative structure-odour relationship

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    Computer Aided Aroma Design (CAAD) is likely to become a hot issue as the REACH EC document targets many aroma compounds to require substitution. The two crucial steps in CAMD are the generation of candidate molecules and the estimation of properties, which can be difficult when complex molecular structures like odours are sought and their odour quality are definitely subjective or their odour intensity are partly subjective as stated in Rossitier’s review (1996). The CAAD methodology and a novel molecular framework were presented in part I. Part II focuses on a classification methodology to characterize the odour quality of molecules based on Structure – Odour Relation (SOR). Using 2D and 3D molecular descriptors, Linear Discriminant Analysis (LDA) and Artificial Neural Network are compared in favour of LDA. The classification into balsamic / non balsamic quality was satisfactorily solved. The classification among five sub notes of the balsamic quality was less successful, partly due to the selection of the Aldrich’s Catalog as the reference classification. For the second case, it is shown that the sweet sub note considered in Aldrich’s Catalog is not a relevant sub note, confirming the alternative and popular classification of Jaubert et al., (1995), the field of odours

    Retieji miško ir pajūrio grybai: antioksidacinių ir biologinių savybių įvertinimas.

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    Due to the metabolic diversity, ecological variety, significant role in nature and complicated web of life cycles, fungi have attracted the attention of various scientists, mycologists, chemists, biologists and pharmacists in multiple ways. A large, untapped, and chemically diversity resource of bioactive metabolites from wild macrofungi provide increasing opportunities for finding new lead structures for medicinal, nutritional, functional, therapeutic and phytochemical chemistry. The main aim of this study was to investigate antioxidant, antimicrobial and other bioactivities of the selected underinvestigated wild mushroom species to obtain scientific information, which is required for their valorisation as a source for human nutrition and production of functional ingredients. In this study, comprehensive and systematic evaluation of antioxidant and antimicrobial properties of wild mushroom species provides important data for their further valorisation as a source of valuable ingredients. More specifically, the extracts isolated from the species possessing the strongest antioxidant potential may be promising protecting agents against oxidative damage and inhibitors of gastrointestinal nematodes. The principal components of such species, hispidin, hispolon and inonotic acid methyl ester may represent a group of new natural compounds for developing functional ingredients for nutraceuticals, functional foods, pharmaceuticals and other applications

    Rare forest and coastal-dune mushroom: evaluation of antioxidant and biological properties.

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    Due to the metabolic diversity, ecological variety, significant role in nature and complicated web of life cycles, fungi have attracted the attention of various scientists, mycologists, chemists, biologists and pharmacists in multiple ways. A large, untapped, and chemically diversity resource of bioactive metabolites from wild macrofungi provide increasing opportunities for finding new lead structures for medicinal, nutritional, functional, therapeutic and phytochemical chemistry. The main aim of this study was to investigate antioxidant, antimicrobial and other bioactivities of the selected underinvestigated wild mushroom species to obtain scientific information, which is required for their valorisation as a source for human nutrition and production of functional ingredients. In this study, comprehensive and systematic evaluation of antioxidant and antimicrobial properties of wild mushroom species provides important data for their further valorisation as a source of valuable ingredients. More specifically, the extracts isolated from the species possessing the strongest antioxidant potential may be promising protecting agents against oxidative damage and inhibitors of gastrointestinal nematodes. The principal components of such species, hispidin, hispolon and inonotic acid methyl ester may represent a group of new natural compounds for developing functional ingredients for nutraceuticals, functional foods, pharmaceuticals and other applications

    Study of the chemical speciation of the national violet collection and setting up of an agro-refining of the violet of Toulouse

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    Le projet « Viola Tolosa » a pour objectif de valoriser une plante produite en Occitanie, la violette et plus particulièrement l’emblématique violette de Toulouse, pour des domaines essentiellement non alimentaires tels que la chimie des substances naturelles et la cosmétique. Les violettes appartiennent au genre Viola qui comprend plus de 500 espèces. Aujourd’hui, leurs usages sont principalement limités à des aspects ornementaux et culinaires. Néanmoins, l’intérêt croissant de la part des acteurs de la filière (industriels, cultivateurs et académiques) a conduit la région Occitanie à mettre en place le projet Viola Tolosa intitulé « Spéciation chimique de la collection nationale des violettes et mise en place d’un agro-raffinage de la violette de Toulouse ». Il comporte quatre aspects interdisciplinaires associant aspects fondamentaux et applicatifs. La caractérisation de la centaine de plants de la collection de violettes détenue par les serres municipales de Toulouse, identifiée à 80% par des noms de cultivars ou vernaculaires, a été réalisée par l’intermédiaire d’études génétique et chimiotaxonomique. Une première étude génétique basée sur les séquences des espaces internes transcrits a permis de classer 58% de la collection au rang d’espèce. Cette étude phylogénétique a été complétée par une étude chimiotaxonomique à l’aide des profils chimiques des fractions volatiles des fleurs et non-volatiles des parties aériennes de la collection. Une projection orthogonale de structures latentes a permis d’indexer 96% de l’ensemble des plants par un nom d’espèce. L’étude des métabolites secondaires non volatils des feuilles a été entreprise dans le but d’étudier le potentiel biologique des violettes, notamment les activités antioxydante, antifongique et inductrice des réponses immunitaires des plantes. L’étude détaillée d’un extrait hydroalcoolique de la violette de Toulouse a permis d’identifier huit composés antioxydants de la famille des flavonoïdes et des coumarines, dont trois ont été caractérisés par RMN 1D et 2D et deux de novo dérépliqués par réseau moléculaire. L’application sur l’ensemble de la collection a ensuite permis d’identifier six composés antioxydants, dont deux coumarines et quatre flavonoïdes, prépondérants chez deux espèces. Une relation espèce-activité a donc été mise en évidence. Au niveau des activités antifongiques, réalisées sur cinq souches de champignons, et de défenses végétales, par l’intermédiaire de l’étude de l’expression du gène marqueur « pathogenesis-related protein 1 », les résultats sont plus ambigus. Cependant, certaines espèces ont présenté une activité plus prononcée que les autres et ce criblage a permis de poser une hypothèse forte quant à l’implication des cyclotides. Finalement, l’ensemble de ces travaux a permis d’obtenir une carte d’identité des violettes de la collection (identification génétique, profil chimique, potentiel biologique) et une description semi-quantitative de l’ensemble des groupes chimiques est proposée par combinaison des données chromatographiques du détecteur Corona (CAD) et des données spectrales. Différentes méthodes d’extraction (électroporation, micro-ondes, CO2 supercritique et extraction hydroalcoolique) répondant aux préceptes de la chimie verte ont ensuite été comparées afin de sélectionner celle présentant le meilleur compromis entre le cahier des charges cosmétiques et l’enrichissement en molécules d’intérêt, en vue d’un transfert technologique.The "Viola Tolosa" project aims to promote a plant produced in Occitanie region, the violet and especially the emblematic violet of Toulouse, essentially for non-food fields such as the chemistry of natural compounds and cosmetics. Violets belong to Viola genus including more than 500 species. Today, their uses are mainly limited to ornamental and culinary aspects. Nevertheless, the growing interest of the actors of the sector (industrials, growers and academicals) led the Occitanie region to implement the Viola Tolosa project entitled "Chemical speciation of the national collection of violets et establishment of an agro-refining of the violet of Toulouse ". It comprises four interdisciplinary aspects associating fundamental and applicative aspects. The characterization of the 100 or so plants in the violet collection owned by the Toulouse municipal greenhouses, including 80% identified by cultivar or vernacular names, was carried out through genetic and chemotaxonomic studies. A first genetic study based on internal transcribed spacers conducted to classify 58% of the collection as a species. This phylogenetic study was completed by chemotaxonomic studies of chemical profiles of flowers volatile fractions and non-volatile aerial parts of the collection. Discriminant analysis of orthogonal projection to latent structure model finally allowed indexation of 96% of all plants with a species name. Study of non-volatile secondary metabolites of leaves has also been undertaken to study the biological potential of violets, including antioxidant, antifungal and defense inducer. The detailed study of a hydroalcoholic extract of the violet of Toulouse allowed the identification of eight antioxidant compounds belonging to flavonoids and coumarins. Three of them have been characterized by 1D and 2D NMR and two were de novo dereplicated through molecular network. The application to the whole collection conducted to highlight six antioxidant compounds, including two coumarins and four flavonoids, predominant in two species. A species-activity relationship was therefore highlighted. Regarding antifungal activities carried out on five fungal strains, and defense inducer through the study of pathogenesis-related protein 1, the results are more ambiguous. However, some species showed better activity than others and this screening led to a strong hypothesis regarding the involvement of cyclotides. Finally, all this work led to the establishment of an identity card of violets of the collection (genetic identification, chemical profiling, et biological potential) et a semi-quantitative description of all the species is considered by combining chromatographic data based on corona detector et spectral data. Different methods of extraction (electroporation, microwaves, supercritical CO2 et hydroalcoholic extraction) corresponding to green chemistry precepts were then compared in order to select the one presenting the best compromise between cosmetic specifications et enrichment in molecules of interest, for technological transfer

    Chemical and biological characterizations of extracts of medieval aromatic plants from Midi-Pyrenees

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    Les plantes aromatiques font parties des richesses naturelles du patrimoine de la région Midi-Pyrénées mais apparaissent cependant de moins en moins valorisées. Dans le cadre de la recherche de nouveaux aromatisants naturels de type WONF, nous avons choisi d'adopter la voie de valorisation des plantes aromatiques médiévales de cette région car elles ont toujours fait l'objet de cueillette à l'état sauvage sans jamais être cultivées. Dans une première étape, une étude bibliographique a été réalisée, à partir d'anciens ouvrages botaniques et de bases de données scientifiques, afin d'identifier les plantes régionales traditionnellement utilisées par nos ancêtres pour leurs activités aromatisantes, culinaires ou médicinales. Nous avons sélectionné cinq plantes aromatiques : Achillea millefolium, Calamintha grandiflora, Tanacetum balsamita, Myrrhis odorata et Monarda didyma. Dans une deuxième étape, des études physico-chimiques, sensorielles et biologiques des fractions volatiles et non volatiles, obtenues après extractions des plantes médiévales sélectionnées, ont été réalisées pour juger de leurs activités aromatiques, antioxydantes et antibactériennes ainsi que de leur intérêt dans le cadre de nouvelles réglementations européennes. Les résultats de ces travaux montrent des activités odorantes, antioxydantes et antibactériennes significatives pour l'ensemble des plantes sélectionnées. Dans une troisième étape, du fait de la rareté du végétal étudié, nous nous sommes intéressés à deux voies analytiques d'évaluation rapide de la composition de l'huile essentielle native de ces plantes aromatiques ; premièrement au moyen d'un échantillonnage classique couplé à un détecteur à forte sensibilité comme la chromatographie bidimensionnelle et deuxièmement par un échantillonnage spécifique couplé à un détecteur classique pour lequel nous avons développé un appareillage novateur dénommé "Crushing Finger Device" (CFD). Ce dernier permet de mimer instrumentalement l'écrasement de la feuille entre les doigts et de piéger les composés volatils odorants émis en vue de leur analyse chromatographique ultérieure. Enfin, pour une application pré-industrielle, afin d'élargir le champ d'application de ces plantes aromatiques, des études d'infusion des plantes et d'aromatisation des huiles végétales par les huiles essentielles ont été mises en place. Durant le processus d'aromatisation de l'huile végétale, les volatils émis par la plante ou par l'huile essentielle donnent un goût et une saveur spécifique tout en délivrant une activité biologique notable.Midi-Pyrenees region has a rich and unvalorized wild vegetal heritage, especially for aromatic plants. In the framework of the search for new natural flavorings e.g. WONF, we chose to adopt the way of valorization of the medieval aromatic plants of this region, because they have been always picked in a wild state without being ever grown. In a first step, a global bibliographical survey study based on historical books, library archived documents and computerized data banks, was made in order to identify regional plants which were used by our ancestors for their odorous, culinary or medicinal activities. We selected five aromatic plants, e.g. Achillea millefolium, Calamintha grandiflora, Tanacetum balsamita, Myrrhis odorata and Monarda didyma. In a second step, physico-chemical, sensory and biological studies of volatiles and non volatiles fractions, obtained by extractions of the selected medieval plants were carried out, to judge their aromatic, antioxidant and antibacterial activities and their interest within the framework of new european regulations. Theses results show a significant odorous, antioxidant and antimicrobial activities for all selected plants. In a third step, such plants were rare or their harvesting problematic, inducing a limited sampling. We decided to investigate two strategic approaches to perform a rapid evaluation of native essential oil, based either on a classic sampling with a specific/ultra sensitive detection such as Comprehensive GC, nor the use of a specific/high effective sampling system with a classic detection. This last methodology was based on a self designed apparatus “Crushing Finger Device” (CFD), allowing to copy the crushing of leaves between fingers and to trap the volatiles emitted to their later chromatographic analysis. Finally, in the aim to expand the use of aromatic plants, also to enlarge the assortment of oil products, a pre-industrial application were carried out. Infusion of plants and flavoring of vegetable oil by essential oil were studied. During processing of aromatized vegetable oil, volatiles from added aromatic plants or essential oil migrate to oil to give a specific aroma and a significant biological activity. Plantes aromatiques oubliées, Huile essentielle, Antioxydant, Antibactérien, Simulateur de froissement, Composés d’arômes, Achillea millefolium, Calamintha grandiflora, Tanacetum balsamita, Myrrhis odorata, Monarda didyma

    Chemical and biological characterisation of extracts from forgotten or underutilised medicinal and aromatic plants from Midi-Pyrénées (France) and Chongqing (China) regions

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    In both Midi-Pyrénées region (France) and Chongqing region (China), there are rich and underutilized medicinal and aromatic plants (MAP). Aiming at fully exploiting different molecules in these plants, the concept of MAP-refinery was developed and applied to several underutilized medicinal and aromatic plants in these two regions. Several water-based green extraction technologies of natural products (e.g. hydrodistillation, steam distillation and subcritical water extraction) were also investigated to look at their effects on essential oil composition and antioxidants recovery from selected plants. Firstly, lists of forgotten or underutilized medicinal and aromatic plants in both regions were established according to the rules of selection. From the lists, six plants in the Midi-Pyrénées region (Tussilago farfara L., Calendula arvensis L., Robinia pseudoacacia L., Geranium robertianum L., Cytisus scoparius L. and Spartium junceum L.) and three plants in the Chongqing region (Tussilago farfara L., Citrum aurantium L. and Saussurea costus) were finally selected for investigations. Then the MAP-refinery was applied to the selected plants in two regions in order to realise their global valorisation. Volatile extracts composition in the roots of Tussilago farfara L. and Calendula arvensis L., as well as flower buds of Spartium junceum L. were firstly investigated. The main chemical compounds in volatile extract from Tussilago farfara L. roots were sesquiterpene hydrocarbons and aliphatic compounds while main chemical compounds in volatile extract from Calendula arvensis L. roots were oxygenated sesquiterpenes, oxygenated monoterpenes and oxygenated diterpenes. The volatile extract from flower buds of Spartium junceum L. was mainly composed of aliphatic compounds. Antioxidant capacity evaluation results (by DPPH, ABTS, FRAC, ORAC and Folin-Ciocalteu tests) showed that several plant samples like Cytisus scoparius L., Tussilago farfara L., Citrum aurantium L. and Robinia pseudoacacia L. could be potential sources of natural antioxidants. Comparisons of hydrodistillation (HD), steam distillation (SD) and subcritical water extraction (SWE) showed that HD and SD had limited effects on essential oil composition but HD, SD and SWE had significant impacts on the recovery of antioxidants. Hydrodistillation seemed to be a better method for recovery of antioxidant compounds from residues of distillation than steam distillation. However, SWE appeared to be a more efficient method for direct extraction of antioxidant molecules (or phenolic compounds) from plants. In the hydrodistillation process, mineral contents in water were found to have very limited effects on yields of extracts but calcium and bicarbonate ions, had significant decreasing effects on antioxidant capacity and total phenolic content of both aqueous and methanolic extracts. Finally, an improved MAP-refinery was developed. Subcritical water was used for further extraction of antioxidant compounds from residues in original MAP-refinery. In this way, five parts could be obtained from plant materials: volatile extract, aqueous extract, methanolic extract, subcritical water extract and the final residue. The results showed that the improved MAP-refinery significantly increased the recovery of antioxidants compared with original MAP-refinery. This promising process will also allow a better valorisation of the final solid residue due to the lower content of residual water

    Champignons oubliés sylvestres et de dunes : étude de leurs propriétés anti-oxydantes et biologiques

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    En raison de la diversité métabolique, la variété écologique, rôle important dans la nature et web complexe de cycles de vie, les champignons ont attiré l'attention de divers scientifiques, mycologues, chimistes, biologistes et pharmaciens de multiples façons (Tkacz, 2004). Le niveau de consommation de champignons a augmenté au cours des dernières années, et ils restent une des sources commercialement importantes pour les producteurs d'aliments de spécialité (Nowacka et al., 2014). L'expertise scientifique est de plus en plus appliquée pour aider à atteindre les objectifs de développement primaires, qui comprennent la réduction de la pauvreté et de l'utilisation durable des ressources naturelles. De réels progrès ont été et continuent d'être réalisés dans les rôles que les champignons jouent dans la réalisation de ces objectifs (Boa, 2004). Dans le passé, beaucoup de nouveaux métabolites secondaires ayant des structures chimiques diversifiées et différentes fonctions de bioactivité intéressantes ont été isolés à partir de champignons supérieurs. Ces molécules sont susceptibles de fournir des composés de plomb pour les nouvelles substances qui peuvent améliorer les fonctions du corps biologiques ou découvertes médicinales, comme des agents de chimioprévention possédant la bioactivité des immunomodulateurs, anticancéreux, etc. Cependant, de nombreux défis de molécules bioactives de champignons sont rencontrés y compris bioséparation, identification , le métabolisme ou le modèle de dépistage des problèmes biosynthétiques. Les chercheurs ont constamment cherché de nouvelles substances actives de champignons, cependant, les produits commerciaux comme encore sont très limitées et principalement de la culture sur le terrain, ce qui est évidemment un temps et un processus de main-d'oeuvre (Zhong et Xiao, 2009). Les stratégies visant à améliorer de nouveaux métabolites secondaires produits naturels comme utiles existant dans les espèces de champignons sauvages, inconnus et underinvestigated, en raison de la prévalence élevée pourrait être une source complète de composants précieux pour industy. En outre, parmi les espèces connues de la quantité relative de champignons bien étudiés est très faible. Ce fait ainsi que les informations sur le grand potentiel des champignons microscopiques pour la production de métabolites bioactifs, l'expérience dans l'utilisation ethnomédicales de champignons, la nécessité écologique pour les champignons pour produire des métabolites secondaires bioactifs et les possibilités améliorées pour le plomb génétique, pharmacologique et analyse chimique nous faire croire que les champignons ont un grand potentiel pour la bioprospection réussie (Lindequist, Niedermeyer et Julich, 2005). Un grand, inexploitée, et chimiquement ressource diversité des métabolites bioactifs de macrochampignons sauvages offrent des possibilités de trouver de nouvelles structures de plomb pour les médicaments, la nutrition, fonctionnelle, thérapeutique et de la chimie phytochimique, et une nouvelle ère de champignons supérieurs recherche de métabolite secondaire a émergé de plus en plus.Due to the metabolic diversity, ecological variety, significant role in nature, complicated web of life cycles, fungi have attracted the attention of various scientists mycologists, chemists, biologists, pharmacists in multiple ways (Tkacz, 2004). The amounts of mushrooms consumption has been increasing in recent years, and they remain commercially important sources for the producers of speciality foods (Nowacka et al., 2014). Also scientific expertise is increasingly being applied to help achieve the primary development goals, which include poverty alleviation and sustainable use of natural resources. Real progress has been and continues to be made in the roles that mushrooms conduce towards these goals (Boa, 2004). In the past years, many new secondary metabolites with diversified chemical structures and various interesting bioactivities from higher fungi have been isolated. These molecules are more likely to provide lead compounds for new substances that can improve biological body functions or medicinal discovery, like chemopreventive agents possessing the bioactivity of immunomodulatory, anticancer, etc. However, numerous challenges of bioactive molecules from mushrooms are encountered including bioseparation, identification, biosynthetic metabolism or screening model issues. Researchers have constantly searched new active substances from mushrooms, however the commercial products are yet very limited and mainly from field cultivation, which is obviously a time-consuming and labor-intensive process (Zhong and Xiao, 2009). Strategies to enhancing new secondary metabolite existence as useful natural products in industry the wild unknown, underinvestigated mushroom species could be an extensive source. Moreover among the known species the relative amount of well investigated mushrooms is very low. This fact together with the information about the great potential of microscopic fungi for production of bioactive metabolites, the experience in ethnomedicinal use of mushrooms, the ecologic need for fungi to produce bioactive secondary metabolites and the improved opportunities for genetic, pharmacological and chemical analysis let us believe that mushrooms have a great potential for successful bioprospecting (Lindequist, Niedermeyer and Julich, 2005). A large, untapped, and chemical diversity resource of bioactive metabolites from wild macrofungi provide more and more opportunities for finding new lead structures for medicinal, nutritional, functional, therapeutical, phytochemical chemistry, and a new era of higher fungi secondary metabolite research has appeared
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