Self-Organizing Maps of Molecular Descriptors for Sesquiterpene Lactones and Their Application to the Chemotaxonomy of the Asteraceae Family

The Asteraceae, one of the largest families among angiosperms, is chemically characterised by the production of sesquiterpene lactones (SLs). A total of 1,111 SLs, which were extracted from 658 species, 161 genera, 63 subtribes and 15 tribes of Asteraceae, were represented and registered in two dimensions in the SISTEMATX, an in-house software system, and were associated with their botanical sources. The respective 11 block of descriptors: Constitutional, Functional groups, BCUT, Atom-centred, 2D autocorrelations, Topological, Geometrical, RDF, 3D-MoRSE, GETAWAY and WHIM were used as input data to separate the botanical occurrences through self-organising maps. Maps that were generated with each descriptor divided the Asteraceae tribes, with total index values between 66.7% and 83.6%. The analysis of the results shows evident similarities among the Heliantheae, Helenieae and Eupatorieae tribes as well as between the Anthemideae and Inuleae tribes. Those observations are in agreement with systematic classifications that were proposed by Bremer, which use mainly morphological and molecular data, therefore chemical markers partially corroborate with these classifications. The results demonstrate that the atom-centred and RDF descriptors can be used as a tool for taxonomic classification in low hierarchical levels, such as tribes. Descriptors obtained through fragments or by the two-dimensional representation of the SL structures were sufficient to obtain significant results, and better results were not achieved by using descriptors derived from three-dimensional representations of SLs. Such models based on physico-chemical properties can project new design SLs, similar structures from literature or even unreported structures in two-dimensional chemical space. Therefore, the generated SOMs can predict the most probable tribe where a biologically active molecule can be found according Bremer classification.

Lectotypification of the name Helianthus dentatus Cav., basionym of Viguiera dentata (Cav.) Spreng. (Asteraceae: Heliantheae)

A recent molecular phylogenetic analysis (Schilling & Panero 2011) proposed to narrow the concept of the paraphyletic genus Viguiera Kunth (1818: 176; Asteraceae: Heliantheae) to embrace only the type, V. dentata (Cavanilles 1794: 10) Sprengel (1826: 615). Robinson (1977) emphasized the peculiarities of Viguiera dentata as the "distinctive and unique" presence of hairs on the filaments of the anther, the disk corollas throat less than twice as long as the lobes and densely scabrous below, a combination of features that differs from most member of the genus. During taxonomic studies of Viguiera and related genera, it was discovered that V. dentata has never been typified. The basionym, Helianthus dentatus, was described by Antonio Jose Cavanilles in Icones et Descriptiones Plantarum based on plants grown in the Real Jardin Botanico from seed sent by Martin Sesse from Mexico (Blanco 2000). Previous workers including Blake (1918) and Robinson (1977) have accepted the plate in Cavanilles as the type for Helianthus dentatus Cav.

A synopsis and notes for Baccharis subgen. Tarchonanthoides (Asteraceae: Astereae)

Nomenclatural and taxonomic notes are provided as the result of a taxonomic revision of Baccharis subgen. Tarchonanthoides, currently underway. A list of accepted species within the subgenus, their synonyms, and a revised sectional classification are presented. Protologues and types of previously published names have been reviewed. Currently 21 species and 10 synonyms are recognized within the subgenus. Morphologically, the species of the subgenus are classified into four sections: Canescentes (9 spp.), Coridifoliae (8 spp.), Curitybensis (2 spp.), and Tarchonanthoides (2 spp.). A new combination and status is proposed to B. coridifolia subsp. bicolor, B. uleana is assigned to subgen. Tarchonanthoides, and lectotypes are designated for B. artemisioides, B. curitybensis, B. erigeroides var. dusenii, B. gibertii, B. patens, B. psammophila and B. squarrosa, most of them providing 'second-step' lectotypes.

Pollen morphology of the genus Eremanthus Less. (Vernonieae, Asteraceae)

(Pollen morphology of the genus Eremanthus Less. (Vernonieae, Asteraceae)). In order to evaluate the significance of the pollen morphology for generic and infrageneric taxonomy of the genus Eremanthus (Vernonieae, Asteraceae), and to provide additional data for its phylogenetic reconstruction, the pollen of 20 of the 23 species of the genus was examined using light and scanning electron microscopy. Acetolysed pollen grains were measured, described, and illustrated using light microscopy, while non-acetolysed pollen grains were analyzed using scanning electron microscopy. Pollen grains of these species are isopolar, oblate-spheroidal in most of the species, more rarely prolate spheroidal or suboblate, subtriangular amb, tricolporate and subechinolophate. The variation among quantitative characters does not correlate with the macromorphological subdivision of the genus or with the generic or specific limits.

Glandular trichomes on aerial and underground organs in Chrysolaena species (Vernonieae - Asteraceae): Structure, ultrastructure and chemical composition

Although the occurrence of glandular trichomes is frequently reported for aerial vegetative organs, many questions still remain opened about the presence of such trichomes in underground systems. Here, we present, for the first time, a comparative study concerning the structure, ultrastructure and chemical aspects of both, the aerial and underground glandular trichomes of two different Chrysolaena species, C obovata and C platensis. Glandular trichomes (GTs) were examined using LM, SEM, and TEM and also analyzed by GC-MS and HPLC coupled to UV/DAD and HR-ESI-MS (HPLC-UV-MS). In both aerial (leaf and bud) and underground (rhizophore) organs, the GTs are multicellular, biseriate and formed by five pairs of cells: a pair of support cells, a pair of basal cells, and three pairs of secreting cells. These secreting cells have, at the beginning of secretory process, abundance of smooth ER. The same classes of secondary metabolites are biosynthesized and stored in both aerial and underground GTs of C platensis and C obovata. These GTs from aerial and underground organs have similar cellular and sub-cellular anatomy, however the belowground trichomes show a higher diversity of compounds when compared to those from the leaves. We also demonstrate by means of HPLC-UV-DAD that the sesquiterpene lactones are located inside the trichomes and that hirsutinolides are not artifacts. (C) 2012 Elsevier GmbH. All rights reserved.

TOWARDS NEW BOTANICAL PESTICIDES: THE TOXIC EFFECT OF Eremanthus goyazensis (Asteraceae) LEAVES ESSENTIAL OIL AGAINST Brevipalpus phoenicis (Acari: Tenuipalpidae)

This work reports the chemical characterization of Eremanthus goyzensis essential oil and its toxic effect over Brevipalpus phoenicis. The essential oil displayed a major composition of sesquiterpenes (61.87%) including trans-caryophillene (26.81%) and germacrene-D (13.31%). The fumigation test indicated a promising bioactivity over adult B. phoenicis individuals at 24 h (2.03 mu L/L of air) and 48 h (1.08 mu L/L of air) of exposition. A brief discussion of essential oils composition and their singular role on the toxic effect over B. phoenicis is provided here. Our results may contribute to a new and profitable use of a species of Brazilian flora on agribusiness.

SEASONAL VARIATION OF THE MAJOR SECONDARY METABOLITES PRESENT IN THE EXTRACT OF Eremanthus mattogrossensis Less (Asteraceae: Vernonieae) LEAVES

The species Eremanthus mattogrossensis, known as "veludo do cerrado" (cerrado velvet), is native to the Brazilian Cerrado. Because the amount of metabolites present in plants may be influenced by biological and environmental factors, here we conducted an HPLC-DAD-MS/MS investigation of the metabolite concentrations found in the MeOH/H2O extract of the leaves of this species. The main compounds were identified and quantified, and the metabolites were grouped by chemical class (caffeoylquinic acids, flavonoids, and sesquiterpene lactone). Statistical analysis indicated a straight correlation between the quantity of metabolites and seasonality, suggesting that environmental properties elicit important metabolic responses.

A new species of Paralychnophora (Asteraceae: Vernonieae), and comments on the identity of Paralychnophora bicolor

The type of Paralychnophora bicolor was found to represent another species recently described as P. santosii. The misapplication of the name P. bicolor is reviewed. Also, a new species is here proposed, P. glaziouana, for plants previously identified as P. bicolor, since the only available name, P. schwackei, is an illegitimate combination. A key to Paralychnophora is given.

Comparing assemblages of Asteraceae and their insect herbivores under different land-use regimens

Accelerated tropical landscape changes occurring over recent decades have produced environmental mosaics comprising remaining isolated green areas and mixed land-use types. Our objective was to study the effects of alterations in the natural landscape on the species composition and structure of assemblages of Asteraceae and their endophagous insects through comparisons between cerrado (savanna), pastures and Eucalyptus stands. We first investigated whether similarities between assemblages of Asteraceae and their insects varied among land uses or localities. Secondly, we asked whether assemblages of Eucalyptus stands and pastures are subsets of those within the cerrado. We sampled within randomly deployed transects in 15 areas. Land use was found to be an important factor in determining plant composition similarity; however, locality did not exert any significant influence. Pastures were less similar to one another, suggesting high beta diversity. Similarities among insect assemblages were correlated with plant assemblage composition, but not with land use or locality. Species of Tephritidae were distributed along localities independently of land use. High beta diversity in Asteraceae assemblages among cerrados and pastures was supported by nestedness analysis. Plant assemblages in Eucalyptus stands were subsets of cerrado, but pasture assemblages were only partial subsets. A higher degree of nestedness in insect assemblages than in plant assemblages indicated lower beta diversity within these herbivores. Our data indicate that many herbivores are specialized on widely distributed plant genera. Conservation of Asteraceae species and their flower head insects depends not only on maintenance of landscape fragments but also on the correct matching of management form and land use. Such management may contribute to reducing isolation of plant and insect species by increasing the connectivity of remaining cerrado tracts, allowing population maintenance even at low abundances.

Anatomy and essential oils from aerial organs in three species of Aldama (Asteraceae-Heliantheae) that have a difficult delimitation

Recently, molecular analysis caused the South American Viguiera Kunth species to be transferred to Aldama La Llave. However, the circumscription has not been established for certain of the South American species, including Aldama filifolia (Sch. Bip. ex Baker) E. E. Schill. & Panero, A. linearifolia (Chodat) E. E. Schill. & Panero and A. trichophylla (Dusen) Magenta (comb. nov.), which had previously been treated as synonyms because of their high similarity. Therefore, the present study aimed to evaluate the anatomy of the aerial organs, and the yield and chemical composition of the essential oils from these three species, to determine the differences among them and thereby assist in species distinction. The anatomical analysis identified characteristics unique to each species, which are primarily related to the position and occurrence of secretory structures. Histochemical analysis demonstrated that the glandular trichomes and the canals secrete lipophilic substances, which are characterised by the presence of essential oils. The analysis of these essential oils identified monoterpenes as their major constituent and allowed for the recognition of chemical markers for each species. The anatomical and chemical characteristics identified by the present study confirmed that the studied samples belong to three distinct taxa.

Mikania glomerata Sprengel (Asteraceae) influences the mutagenicity induced by doxorubicin without altering liver lipid peroxidation or antioxidant levels

As shown in numerous studies, natural compounds may exert adverse effects, mainly when associated with some drugs. The hydroalcoholic extract of Mikania glomerata is the pharmaceutical form present in commercially available syrup used for the treatment of respiratory diseases in popular Brazilian medicine. The objective of the present investigation was (1) to evaluate the preventive effects of standardized hydroalcoholic extract of M. glomerata (MEx) against antitumoral drug doxorubicin (DXR)-induced micronucleated polychromatic erythrocytes (MNPCE) in a subchronic assay in mice, and (2) to determine the liver content of malondialdehyde (MDA) and the antioxidants glutathione (GSH) and vitamin E (VE). Male Swiss mice were treated for 30 d with MEx added to drinking water, combined or not with DXR (90 mg/kg body weight) injected intraperitoneally (ip) 24 h before analysis. The results demonstrated that MEx produced no genotoxic damage, but significantly increased the frequency of MNPCE induced by DXR, indicating a drug-drug interaction. This rise was not accompanied by lipid peroxidation or antioxidants level reduction, as measured by MDA, GSH, and VE. Despite the presence of coumarin (a known antioxidant), MEx may exert adverse effects probably in association with mutagenic compounds, although this effect on DNA damage did not involve oxidative stress.

Baccharis napaea (Asteraceae, Astereae): a new species of subgen. Tarchonanthoides sect. Coridifoliae from the subtropical highlands of southern Brazil

Baccharis napaea, a new species belonging to subgen. Tarchonanthoides sect. Coridifoliae is described and illustrated. The new species is compared to and distinguished from the sympatric species B. coridifolia, B. erigeroides, and B. scabrifolia, and from the allopatric B. bicolor. Baccharis napaea occurs in open subtropical highland grasslands and the edges and open glades of subtropical mixed forests on the south Brazilian plateau. Additionally, a distribution map and description of habitat and conservation status of the new species are presented.

Baccharis umbellata (Asteraceae, Astereae): a new species endemic to the highest summits of Parana, Southern Brazil

Baccharis umbellata, a new species of Parana State, southern Brazil, is described. The new species, belonging to subgen. Baccharis sect. Agglomeratae, is easily recognized by the pedunculate heads arranged in an umbel-like capitulescence. Baccharis umbellata is a narrow endemic of the peaks of the southern range of Serra do Mar. It is morphologically most similar to the allopatric species B. platypoda, which mainly inhabits mountain summits in western and eastern South America. Illustrations, a distribution map, habitat information, and a conservation assessment are also provided for the new species.

Seasonal variation of the major secondary metabolites present in the extract of Eremanthus mattogrossensis Less (Asteraceae: Vernonieae) leaves

The species Eremanthus mattogrossensis, known as "veludo do cerrado" (cerrado velvet), is native to the Brazilian Cerrado. Because the amount of metabolites present in plants may be influenced by biological and environmental factors, here we conducted an HPLC-DAD-MS/MS investigation of the metabolite concentrations found in the MeOH/H2O extract of the leaves of this species. The main compounds were identified and quantified, and the metabolites were grouped by chemical class (caffeoylquinic acids, flavonoids, and sesquiterpene lactone). Statistical analysis indicated a straight correlation between the quantity of metabolites and seasonality, suggesting that environmental properties elicit important metabolic responses.

Towards new botanical pesticides: the toxic effect of Eremanthus goyazensis (Asteraceae) leaves essential oil against Brevipalpus phoenicis (Acari: Tenuipalpidae)

This work reports the chemical characterization of Eremanthusgoyzensis essential oil and its toxic effect over Brevipalpus phoenicis. The essential oil displayed a major composition of sesquiterpenes (61.87%) including trans-caryophillene (26.81%) and germacrene-D (13.31%). The fumigation test indicated a promising bioactivity over adult B. phoenicis individuals at 24 h (2.03 µL/L of air) and 48 h (1.08 µL/L of air) of exposition. A brief discussion of essential oils composition and their singular role on the toxic effect over B. phoenicis is provided here. Our results may contribute to a new and profitable use of a species of Brazilian flora on agribusiness.