TOCSY, hydrogen decoupling and computational calculations to an unequivocal structural elucidation of a new sesquiterpene derivative and identification of other constituents from Praxelis sanctopaulensis.

INTRODUCTION: Praxelis genus comprises 24 species, however, only two species of this genus have been chemically investigated. Here we investigated Praxelis sanctopaulensis, a native plant from Brazil, that occurs mainly in Cerrado regions. OBJECTIVE: The goal was to identify the specialised metabolites from P. sanctopaulensis, and compare with those described from Praxelis and Chromolaena species. METHODS: The phytochemical study of P. sanctopaulensis was performed through different chromatography techniques, including high-performance liquid chromatography (HPLC), gas chromatography flame ionisation detector (GC-FID), and ultra-high-performance liquid chromatography high-resolution tandem mass spectrometry (UHPLC-HRMS/MS). The structures of the compounds were established based on spectroscopic analysis, total correlated spectroscopy (TOCSY), hydrogen decoupling and computational calculations was used to an unequivocal structural elucidation of a new sesquiterpene. The antioxidant activity was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP), and antimicrobial assay was performed by the microdilution method. Comparison of the flavonoids described P. sanctopaulensis was carried out using principal component analysis. RESULTS: The phytochemical investigation of P. sanctopaulensis led to the isolation of a pair of diastereomers, praxilone A and praxilone B. Seven known compounds were isolated from this species, another 14 fatty acids were detected in hexane fraction, and 26 compounds were identified from ethyl acetate fraction. All these compounds are being described for the first time in this species, with the exception of viridifloric acid. The ethyl acetate fraction showed potent antioxidant activity. CONCLUSIONS: Forty-seven compounds are described from P. sanctopaulensis. The combination of different techniques of nuclear magnetic resonance (NMR) spectroscopy and computational calculations allowed the unequivocal structure elucidation of a new cadinene. The clustering analysis showed similarities between the flavonoids identified in P. sanctopaulensis and in Chromolaena species.

Volatile constituents of Eupatorieae (Asteraceae). Compositional multivariate analysis of volatile oils from Southern Brazilian species in the subtribe Disynaphiinae.

Volatile oils (VOs) obtained from the aerial parts of species from the Disynaphiinae subtribe (genera Acanthostyles, Campovassouria, Disynaphia, Grazielia, Raulinoreitzia, and Symphyopappus) of Eupatorieae (Asteraceae) collected in Rio Grande do Sul, southern Brazil, were characterized using GC-MS. The yield of VOs relative to fresh material ranged from 0.2 to 1.7% between the Disynaphiinae subtribe samples (Acanthostyles buniifolius, Campovassouria cruciata, Disynaphia ericoides, D. ligulifolia, D. spathulata, Symphyopappus casarettoi, S. reticulatus, S. itatiayensis, Grazielia gaudichaudieana, G. intermedia, G. nummularia, G. serrata, Raulinoreitzia crenulata, and R. tremula). The VOs in this subtribe were mainly composed of terpene compounds. Compositional multivariate analysis demonstrated clustering between the samples of Grazielia and Raulinoreitzia on one side, which contain relatively higher proportions of monoterpenes, and Disynaphia and Campovassouria, which contain more oxygenated sesquiterpenes. The samples of Symphyopappus and Acanthostyles, which contain more sesquiterpene hydrocarbons, were located between these two main groups. Multivariate analysis accounting for the recent proposals of subtribal recircumscription of Eupatorieae was also performed. The odd chemistry of S. itatiayensis was in accordance with the recent attempts to exclude it from the genus Symphyopappus.

Helenin from Stevia lucida. The first report of this natural eudesmanolide mixture in Eupatorieae tribe.

From aerial parts of Stevia lucida Lagasca was isolated the natural mixture of isomeric eudesmanolides helenin. The identification and quantification of the constituents of helenin (alantolactone 1 and isoalantolactone 2, ratio 3:7) was performed through the quantitative analysis of its 1D and 2D NMR spectra.

A new genus of Compositae (Eupatorieae, Piqueriinae) from Peru, named Centenaria to honour the 100 th anniversary of the Natural History Museum of the National University Mayor of San Marcos.

A little herb from central Peru is recognised as a new species of a new genus. Centenariarupacquiana belongs to the tribe Eupatorieae, subtribe Piqueriinae. It has asymmetrical corollas with two inner lobes smaller, a flat and epaleaceous receptacle and the presence of pappus. In Peru, Centenaria is related to the genera Ferreyrella and Ellenbergia, but Ferreyrella is different by having no pappus and a paleate receptacle; and on the other hand, Ellenbergia is different by having symmetrical corollas.

ResumenUna pequeña hierba del centro del Perú es reconocida como una especie nueva en un nuevo género. Centenariarupacquiana es miembro de la tribu Eupatorieae subtribu Piqueriinae. Tiene corolas asimétricas con dos lóbulos internos más pequeños, receptáculo plano y sin palea, y presencia de papus. En Perú, Centenaria está relacionada a los géneros Ferreyrella y Ellenbergia, Pero Ferreyrella se diferencia por carecer de papus y presentar un receptáculo con paleas; por otro lado, Ellenbergia se diferencia por sus corolas simétricas.

Meso- or xeromorphic? Foliar characters of Asteraceae in a xeric scrub of Mexico.

BACKGROUND: The anatomical traits associated with water deficit are also observed in plants growing in poor soils. The species may resist water deficit through three main strategies: escape, avoid or tolerate. The Pedregal de San Ángel Ecological Reserve (REPSA), Mexico, is an environment with low nutrient soil and low water availability. It is set on the basalt formation derived from the Xitle volcano eruption. The main vegetation type is characterized as xerophytic shrub. Thus we expect that species growing in this community will show leaf xeromorphic traits and may have any of the three response strategies. We analyzed the foliar anatomy of 52 species of the Asteraceae family at the REPSA because it is the most abundant angiosperm family in the site, showing a wide variety of growth forms and anatomical variation. RESULTS: The foliar anatomies of the studied Asteraceae were highly variable as well as their quantitative traits as revealed by principal component analysis. This agrees with previous studies that found great anatomical variation within the family. Leaves have multiple layered palisade parenchyma and parenchyma bundle sheaths and could not be categorized as xeromorphic because they possess mesomorphic leaf features as simple lamina, single-layered epidermis, and soft large-size glabrous leaves with high specific leaf area. CONCLUSIONS: The combination of mesomorphic and few xeromorphic foliar traits with other characters at the genus and tribal level probably has been essential in Asteraceae to colonize various environments, including those with low water and nutrient availability.

Origins and recent radiation of Brazilian Eupatorieae (Asteraceae) in the eastern Cerrado and Atlantic Forest.

The remarkable diversity of Eupatorieae in the Brazilian flora has received little study, despite the tribe's very high levels of endemism and importance in the threatened Cerrado and the Atlantic Forest biodiversity hotspots. Eupatorieae are one of the largest tribes in Asteraceae with 14 of 19 recognized subtribes occurring in Brazil. We constructed the largest phylogeny of Brazilian Eupatorieae to date that sampled the nrITS and ETS, chloroplast ndhI and ndhF genes, and the ndhI-ndhG intergenic spacer for 183 species representing 77 of the 85 Brazilian genera of the tribe. Maximum likelihood and Bayesian phylogenetic analyses showed that these species are not collectively monophyletic, so their distribution reflects multiple introductions into Brazil. A novel clade was found that includes 75% of the genera endemic to Brazil (Cerrado-Atlantic Forest Eupatorieae, "CAFE" clade). This radiation of at least 247 species concentrated in the Cerrado and Atlantic Forest biomes of central eastern Brazil is <7 my old and exhibits several ecologically diverse life forms. Eight subtribes of Brazilian Eupatorieae (Ageratinae, Alomiinae, Ayapaninae, Critoniinae, Disynaphiinae, Eupatoriinae, Gyptidinae and Hebecliniinae) and 16 genera (Ageratum, Agrianthus, Austroeupatorium, Bejaranoa, Chromolaena, Critonia, Disynaphia, Grazielia, Hatschbachiella, Heterocondylus, Koanophyllon, Lasiolaena, Neocabreria, Praxelis, Stylotrichium, and Symphyopappus) were found to be polyphyletic. We attribute incongruities between the molecular phylogenetic results and the current classification of the tribe mostly to convergent evolution of morphological characters traditionally used in the classification of the tribe. We used these phylogenetic results to suggest changes to the classification of some subtribes and genera of Eupatorieae that occur in Brazil.

Bricklebush (Brickellia) phylogeny reveals dimensions of the great Asteraceae radiation in Mexico.

Data from molecular phylogenetics were used to assess aspects of diversity and relationships in Brickellia, a large and widespread genus of Eupatorieae. The dataset included sequence data from nuclear ribosomal ITS, ETS, and plastid psbA-trnH regions. An initial question was to assess the monophyly of the genus and whether Barroetea, Phanerostylis, and Kuhnia should be recognized as separate from or included in Brickellia. The results supported the hypothesis that Brickellia is monophyletic, with the small (2-3 species) Pleurocoronis as the sister group and showed Barroetea, Phanerostylis, and Kuhnia all embedded within the genus. Results of a time calibrated phylogeny from a BEAST analysis gave an estimated origination time for Brickellia at about 9 million years ago (Ma), with the oldest split within the genus dated at about 7.5Ma. A BAMM analysis based on the time calibrated tree showed that Brickellia has one rate shift in diversification associated with its origin in the late Miocene. Some lineages within the genus have had an increase in the rate of diversification over the past 5Ma, whereas other lineages have had a decrease in net diversification during this period. The results also elucidated nine clades within Brickellia which are accepted as taxonomic sections, and that will form logical units for future detailed studies.

Complete chloroplast genome sequences of Praxelis (Eupatorium catarium Veldkamp), an important invasive species.

Praxelis (Eupatorium catarium Veldkamp) is a new hazardous invasive plant species that has caused serious economic losses and environmental damage in the Northern hemisphere tropical and subtropical regions. Although previous studies focused on detecting the biological characteristics of this plant to prevent its expansion, little effort has been made to understand the impact of Praxelis on the ecosystem in an evolutionary process. The genetic information of Praxelis is required for further phylogenetic identification and evolutionary studies. Here, we report the complete Praxelis chloroplast (cp) genome sequence. The Praxelis chloroplast genome is 151,410 bp in length including a small single-copy region (18,547 bp) and a large single-copy region (85,311 bp) separated by a pair of inverted repeats (IRs; 23,776 bp). The genome contains 85 unique and 18 duplicated genes in the IR region. The gene content and organization are similar to other Asteraceae tribe cp genomes. We also analyzed the whole cp genome sequence, repeat structure, codon usage, contraction of the IR and gene structure/organization features between native and invasive Asteraceae plants, in order to understand the evolution of organelle genomes between native and invasive Asteraceae. Comparative analysis identified the 14 markers containing greater than 2% parsimony-informative characters, indicating that they are potential informative markers for barcoding and phylogenetic analysis. Moreover, a sister relationship between Praxelis and seven other species in Asteraceae was found based on phylogenetic analysis of 28 protein-coding sequences. Complete cp genome information is useful for plant phylogenetic and evolutionary studies within this invasive species and also within the Asteraceae family.

Zyzyura, a new genus of Eupatorieae (Asteraceae) from Belize.

A new Genus, Zyzyura is named to accommodate Fleischmannia mayana Pruski that has an eximbricate involucre, a high-conical receptacle, a corolla with a slender base closely investing the style and with a broadly campanulate limb, enlarged elongate cells in the carpopodium, short and broad distally protruding cells in the corolla lobes, and broad rounded anther appendages.

Contribution for the phytochemical studies of Ageratum fastigiatum

Organic extracts from leaves plus branches plus inflorescences of Ageratum fastigiatum (Gardner) R. M. King & H. Rob., Asteraceae, were fractionated through classic chromatography. The steroids stigmasterol, chondrillasterol and campesterol were isolated from hexane extract. The triterpenes lupeol, taraxasterol, α-amyrin, β-amyrin, pseudotaraxasterol, lupeol acetate and α-amyrin acetate were isolated from ethyl acetate extract. Steroids and triterpenes were identified by GC-MS. The coumarin ayapin was isolated from ethanol extract and identified by NMR. Essential oils of the fresh leaves and fresh inflorescences were obtained by hydrodistillation and analyzed for GC-MS. The main components in both essential oils were α-pinene, limonene and germacrene D.

A new species of fleischmannia (asteraceae, eupatorieae) from el salvador.

Fleischmannia profusa is named as new from El Salvador based on material with deltoid leaf blades, numerous axillary fascicles of leaves on the vegetative stems and c. 60 sharply obviously acuminate involucral bracts in 4-5 strongly gradate series.

Detection of flavonoids in glandular trichomes of Chromolaena species (Eupatorieae, Asteraceae) by reversed-phase high-performance liquid chromatography

In this work, twelve flavonoids were detected in glandular trichomes of two species of Chromolaena through the glandular microsampling technique and HPLC-UV-DAD analysis. This is the first time that the accumulation of flavonoids in glandular trichomes of the genus Chromolaena is reported. Based on the results, we suggest that this technique can be an useful tool in the search of new compounds with medicinal properties as well as in chemotaxonomic studies of Eupatorieae.

Neste trabalho 12 flavonóides foram detectados nos tricomas glandulares de duas espécies de Chromolaena através do emprego da técnica de microamostragem de tricomas glandulares, associada à análise por CLAE. Esta é a primeira vez que se relata o acúmulo de flavonóides em tricomas glandulares no gênero. Com base nos resultados obtidos, podemos sugerir que esta técnica pode ser uma ferramenta útil na busca de substâncias com propriedades medicinais e em estudos quimiotaxonômicos de Eupatorieae.