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PubMed2005

Sesquiterpenes from Centaurea aspera.

The aerial parts of two subspecies of Centaurea aspera L. (Asteraceae) yielded the germacranolides 1a-h, 2, 3, 4 and 5, the elemane derivatives 6d and 6f, the lignan matairesinol, the degraded terpene loliolide, and the onopordopicrin-valine dimeric adduct 7. From these, compounds 1e, 3 and 6d are natural products. The chemical composition of the two subspecies is very similar, a circumstance which does not support a taxonomic subdivision of the species.

Centaurea↗
PubMed2006

Americanin, a bioactive dibenzylbutyrolactone lignan, from the seeds of Centaurea americana.

The reversed-phase preparative HPLC analysis of the methanol (MeOH) extract of the seeds of Centaurea americana afforded a dibenzylbutyrolactone lignan, 3''-O-caffeoyl arctiin (named americanin), together with five known lignans, arctiin, arctigenin, matairesinol, matairesinoside and lappaol A, and two known phytoecdysteroids, 20-hydroxyecdysone and makisterone A. While the structures of the known compounds were determined by direct comparison of the spectral data with published data, the structure of americanin was elucidated by UV, MS and a combination of 1D and 2D NMR spectral analyses. The antioxidant properties and toxicity of the extracts and the isolated compounds were determined by the DPPH and the brine shrimp lethality assays, respectively.

Centaurea↗
PubMed2006

Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana.

Two elemanolide sesquiterpenes and two eudesmane-type sesquiterpene glycosides named hierapolitanins A-D, were isolated, together with five known compounds, two flavones; hispidulin and jaceosidin, a flavon-C-glycoside, shaftoside, a flavonol glycoside, kaempferol-3-O-rutinoside and a neolignan, dehydrodiconiferyl alcohol from the aerial parts of Centaurea hierapolitana Boiss. (Asteraceae). Structure elucidations were based on spectroscopic evidence.

Centaurea↗
PubMed2005

HPLC determination of free nitrogenous compounds of Centaurea solstitialis (Asteraceae), the cause of equine nigropallidal encephalomalacia.

Centaurea solstitialis (yellow star thistle) has been proven to cause equine nigropallidal encephalomalacia in horses. Over the last fifty years, nigropallidal encephalomalacia has been of interest to human medicine due to the possible connection with Parkinson's disease. Previous studies indicated the presence of neurotoxic nitrogenous compounds in polar extracts of the plant. In order to give a more detailed description of the nitrogen-containing fraction of C. solstitialis, various samples were collected at different development stages. Different aliquots of the same aqueous extract were directly derivatized with o-phthaldialdehyde and dansyl chloride and analyzed separately by reversed-phase HPLC. A complete profile of the free nitrogenous fraction of C. solstitialis was given and results obtained with the two derivatization procedures were compared. No particularly high level of free aspartic and glutamic acids, two potent neuroexcitotoxic amino acids, were found in polar extracts of the plant. Tyramine resulted to be the most important biologically active amine present in C. solstitialis (with a mean concentration of 2.0 mg/100 g of dry weight).

Amino Acids↗
PubMed2006

Reticulate evolution in the Acrolophus subgroup (Centaurea L., Compositae) from the western Mediterranean: origin and diversification of section Willkommia Blanca.

Section Willkommia (Centaurea, Compositae) is endemic to the east-central portion of the Iberian Peninsula and northwestern Africa. The section has been included with sections Acrolophus and Phalolepis in the informal subgroup Acrolophus. We have used a molecular phylogenetic approach to test the hypothesis proposed by earlier authors that the diversification of section Willkommia involved a schizoendemic process from an ancestral syngameon. Comparative analysis of the transcribed spacer sequences of the nuclear ribosomal DNA (ITS and 3'ETS) regions reveals the presence of three different types of ribosomal sequences in the Acrolophus subgroup (referred to here as the Willkommia, Acrolophus-Phalolepis and Simulans ribotypes) which show a sectional-independent geographic structure. This evidence, together with the presence of additive polymorphic sites in the Willkommia sequences which agree with the geographic distribution of the taxa, suggests that members of section Willkommia and the western Mediterranean taxa of sections Acrolophus and Phalolepis fit a reticulate evolution model.

Base Composition↗
PubMed2002

Flavonoid glycosides from Centaurea pseudoscabiosa subsp. pseudoscabiosa from Turkey.

Three flavonoid glycosides were isolated and characterized, together with a further 13 substances belonging to various classes of compounds, in particular two phenolic acids, a coumarin, a sugar and nine flavonoids from the flowered aerial parts of Centaurea pseudoscabiosa subsp. pseudoscabiosa Boiss. et Buhse (Asteraceae). Some considerations about their evolutionary meaning are provided.

Biological Evolution↗
PubMed2003

Biological activity of serotonin conjugates from the seeds of Centaurea nigra.

Two serotonin conjugates, N-(trans-p-coumaroyl)-serotonin (1) and N-(trans-feruloyl)-serotonin (maoschamine, 2), isolated from the methanol extract of the seeds of Centaurea nigra, have been assessed for antibacterial and free radical scavenging activities. The general toxicity of 1 and 2 has also been determined by the brine shrimp lethality bioassay.

Animals↗
PubMed2003

Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots.

Invasive plants are believed to succeed in part by secretion of allelochemicals, thus displacing competing plant species. Centaurea maculosa (spotted knapweed) provides a classic example of this process. We have previously reported that spotted knapweed roots secrete (+/-)-catechin and that (-)-catechin, but not (+)-catechin, is phytotoxic and hence may be a major contributor to C. maculosa's invasive behavior in the rhizosphere. In this communication, we explore both structure/activity relationships for flavonoid phytotoxicity and possible biosynthetic pathways for root production of (+/-)-catechin. Kaempferol and dihydroquercetin were shown to be phytotoxic, while quercetin was not. Kaempferol was converted to dihydroquercetin and (+/-)-catechin when treated with total root protein extracts from C. maculosa, but quercetin was not. This finding suggests an alteration in the standard flavonoid biosynthetic pathway in C. maculosa roots, whereby kaempferol is not a dead-end product but serves as a precursor to dihydroquercetin, which in turn leads to (+/-)-catechin production.

Catechin↗
PubMed2005

Sesquiterpene lactones from Centaurea spinosa and their antibacterial and cytotoxic activities.

Ten sesquiterpene lactones, 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)sonchucarpolide (4-epi-malacitanolide) (1), 8alpha-O-(4-acetoxy-2-hydroxymethylbuten-2-oyloxy)-4-epi-sonchucarpolide (2), malacitanolide (3), its 4'-acetyl derivative (4), 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)dehydromelitensine (5), 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)-15-oxo-5,7alphaH,6betaH-eleman-1,3,11(13)-trien-6,12-olide (6), the germacranolides 8alpha-O-(4-acetoxy-2-hydroxymethylbuten-2-oyloxy)salonitenolide (7), cnicin (8), and 4'-acetylcnicin (9), and the sesquiterpene methyl 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)-6alpha,15-dihydroxyelema-1,3,11(13)-trien-12-oate (10), were isolated from the aerial parts of Centaurea spinosa. Nine known flavonoids were also isolated. The structures and the stereochemistry of the new compounds 1 and 2 were deduced by spectroscopic methods. The in vitro activity of 1-10 against three Gram-positive and three Gram-negative bacteria was evaluated using a microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines.

Anti-Bacterial Agents↗
PubMed2003

Focussed beam reflectance measurement (FBRM) monitoring of particle size and morphology in suspension cultures of Morinda citrifolia and Centaurea calcitrapa.

Laser light scattering technology, as applied in the Lasentec focussed beam reflectance measurement (FBRM) system, was used to characterise two morphologically dissimilar plant cell suspension cultures, Morinda citrifolia and Centaurea calcitrapa. Shake-flask suspensions were analysed in terms of biomass concentration and aggregate size/shape over the course of typical batch growth cycles. For the heavily aggregated C. calcitrapa, biomass levels [from 10-160 g fresh weight (fw) l(-1))] were linearly correlated with FBRM counts. For M. citrifolia, which grows in unbranched chains of 2-10 elongated cells, linear correlation of biomass concentration with FBRM counts was applicable in the range 0-100 g fw l(-1); at higher levels (100-300 g fw l(-1)), biomass was non-linearly correlated with FBRM counts and length-weighted average FBRM chord length. For both cell systems, particle morphology (size/shape) was quantified using semi-automated digital image analysis. The average aggregate equivalent diameter (C. calcitrapa) and average chain length (M. citrifolia), determined using image analysis, closely tracked the FBRM average chord length. The data clearly demonstrate the potential for applying the FBRM technique for rapid characterisation of plant cell suspension cultures.

Biomass↗
PubMed2006

Centaurea revisited: A molecular survey of the Jacea group.

BACKGROUND AND AIMS: The genus Centaurea has traditionally been considered to be a complicated taxon. No attempt at phylogenetic reconstruction has been made since recent revisions in circumscription, and previous reconstructions did not include a good representation of species. A new molecular survey is thus needed. METHODS: Phylogenetic analyses were conducted using sequences of the internal transcribed spacers (ITS) 1 and 2 and the 5.8S gene. Parsimony and Bayesian approaches were used. KEY RESULTS: A close correlation between geography and the phylogenetic tree based on ITS sequences was found in all the analyses, with three main groups being resolved: (1) comprising the most widely distributed circum-Mediterranean/Eurosiberian sections; (2) the western Mediterranean sections; and (3) the eastern Mediterranean and Irano-Turanian sections. The results show that the sectional classification in current use needs major revision, with many old sections being merged into larger ones. A large polytomy in the eastern Mediterranean clade suggests a rapid and recent speciation in this group. Some inconsistencies between morphology and molecular phylogeny may indicate that hybridization has played a major role in the evolution of the genus. CONCLUSIONS: Phylogenetic analysis of ITS has been useful in identifying the major lineages in the group, and unraveling many inconsistencies in the sectional classification. However, most recent groups in the eastern Mediterranean clade are not resolved and reticulation in the western Mediterranean group of sections makes phylogenetic relationships within these two groups somewhat obscure.

Centaurea↗
PubMedDate not supplied

Inheritance of resistance to clopyralid and picloram in yellow starthistle (Centaurea solstitialis L.) is controlled by a single nuclear recessive gene.

The noxious weed yellow starthistle (Centaurea solstitialis L.) can be controlled effectively at the seedling stage with foliar application of the auxinic herbicides picloram or clopyralid. Although resistance to these herbicides is rare, a yellow starthistle biotype resistant to picloram and cross-resistant to clopyralid was observed in 1989 near Dayton, WA, in a pasture that had been subjected to intensive picloram selective pressure. Our objective was to determine the mode of inheritance for this resistance trait. Transmission of the resistant phenotype was monitored in reciprocal F(1) crosses between susceptible (SCI) and resistant (RDW) plants, their testcross and pseudo-F(2) progeny. Progeny from all crosses, as well as RDW and SCI seedlings of original populations, were sprayed with picloram or clopyralid to distinguish between susceptible and resistant individuals. All F(1) progeny were susceptible to both herbicides, indicating that the resistance trait was of nuclear origin and recessive in nature. Segregation of the resistant phenotype among pseudo-F(2) and testcross progeny of F(1) genotypes demonstrated monofactorial inheritance (P >.25) for resistance to both herbicides. The conclusion that resistance is conferred by a single recessive allele is consistent with the observation that no other picloram-resistant yellow starthistle populations have been identified in the area since picloram selection pressure was abated.

Centaurea↗
PubMed2004

Fine-scale genetic structure and gene dispersal in Centaurea corymbosa (Asteraceae) I. Pattern of pollen dispersal.

Pollen dispersal was characterized within a population of the narrowly endemic perennial herb, Centaurea corymbosa, using exclusion-based and likelihood-based paternity analyses carried out on microsatellite data. Data were used to fit a model of pollen dispersal and to estimate the rates of pollen flow and mutation/genotyping error, by developing a new method. Selfing was rare (1.6%). Pollen dispersed isotropically around each flowering plant following a leptokurtic distribution, with 50% of mating pairs separated by less than 11 m, but 22% by more than 40 m. Estimates of pollen flow lacked precision (0-25%), partially because mutations and/or genotyping errors (0.03-1%) could also explain the occurrence of offspring without a compatible candidate father. However, the pollen pool that fertilized these offspring was little differentiated from the adults of the population whereas strongly differentiated from the other populations, suggesting that pollen flow rate among populations was low. Our results suggest that pollen dispersal is too extended to allow differentiation by local adaptation within a population. However, among populations, gene flow might be low enough for such processes to occur.

Centaurea↗
PubMedDate not supplied

A new active compound from Centaurea species.

The extract containing sesquiterpene lactones of Centaurea iberica (Asteraceae) isolated was separated and a steroidal compound, which is stigmast-1,5-dien-3beta-ol, was purified. The chemical structure was established based on spectroscopic data (UV, IR, MS, 1H NMR, 13C NMR). Both the extract and the compound showed significant antioxidant and antimicrobial activities.

Animals↗
PubMed2004

Fine-scale genetic structure and gene dispersal in Centaurea corymbosa (Asteraceae). II. Correlated paternity within and among sibships.

The fine-scale pattern of correlated paternity was characterized within a population of the narrow-endemic model plant species, Centaurea corymbosa, using microsatellites and natural progeny arrays. We used classical approaches to assess correlated mating within sibships and developed a new method based on pairwise kinship coefficients to assess correlated paternity within and among sibships in a spatio-temporal perspective. We also performed numerical simulations to assess the relative significance of different mechanisms promoting correlated paternity and to compare the statistical properties of different estimators of correlated paternity. Our new approach proved very informative to assess which factors contributed most to correlated paternity and presented good statistical properties. Within progeny arrays, we found that about one-fifth of offspring pairs were full-sibs. This level of correlated mating did not result from correlated pollen dispersal events (i.e., pollen codispersion) but rather from limited mate availability, the latter being due to limited pollen dispersal distances, the heterogeneity of pollen production among plants, phenological heterogeneity and, according to simulations, the self-incompatibility system. We point out the close connection between correlated paternity and the "TwoGener" approach recently developed to infer pollen dispersal and discuss the conditions to be met when applying the latter.

Centaurea↗
PubMed1993

Search for chlorinated sesquiterpene lactones in the neurotoxic thistle Centaurea solstitialis by liquid chromatography-mass spectrometry, and model studies on their possible artifactual formation.

An HPLC method has been developed for the analysis of sesquiterpene lactones of the neurotoxic plant Centaurea solstitialis (Asteraceae). The presence of sesquiterpene lactone chlorohydrins in extracts was investigated by means of liquid chromatography-thermospray mass spectrometry. In contrast to earlier reports of a series of mono- and dichlorohydrins from this plant, traces only of two monochlorohydrins could be detected in lipophilic extracts. Model studies carried out with extracts and with the genuine sesquiterpene diepoxide repin and its epimer subluteolide showed that (i) monochlorohydrins can be formed in CHCl3 under usual laboratory conditions; (ii) the epoxide moiety at C-4 of the sesquiterpenes is extremely labile, reacting immediately and quantitatively with traces of HCl to the corresponding monohydrins; (iii) epoxide ring opening at the acyl side chain occurs only at higher HCl concentrations. Confirmation of the peak identity was obtained by the isotope ratio of chlorinated compounds and comparison with authentic samples. The structures of the mono- and dichlorohydrins were established by NMR spectroscopy.

Chlorine↗
PubMed2006

Oxalate contributes to the resistance of Gaillardia grandiflora and Lupinus sericeus to a phytotoxin produced by Centaurea maculosa.

Centaurea maculosa Lam. is a noxious weed in western North America that produces a phytotoxin, (+/-)-catechin, which is thought to contribute to its invasiveness. Areas invaded by C. maculosa often result in monocultures of the weed, however; in some areas, North American natives stand their ground against C. maculosa and show varying degrees of resistance to its phytotoxin. Two of these resistant native species, Lupinus sericeus Pursh and Gaillardia grandiflora Van Houtte, were found to secrete increased amounts of oxalate in response to catechin exposure. Mechanistically, we found that oxalate works exogenously by blocking generation of reactive oxygen species in susceptible plants and reducing oxidative damage generated in response to catechin. Furthermore, field experiments show that L. sericeus indirectly facilitates native grasses in grasslands invaded by C. maculosa, and this facilitation can be correlated with the presence of oxalate in soil. Addition of exogenous oxalate to native grasses and Arabidopsis thaliana (L.) Heynh grown in vitro alleviated the phytotoxic effects of catechin, supporting the field experiments and suggesting that root-secreted oxalate may also act as a chemical facilitator for plant species that do not secrete the compound.

Antioxidants↗
PubMed1992

Toxic effects of solstitialin A 13-acetate and cynaropicrin from Centaurea solstitialis L. (Asteraceae) in cell cultures of foetal rat brain.

Extracts of the aerial parts of the yellow star thistle (Centaurea solstitialis L.) were prepared using petroleum ether, chloroform and methanol and toxicity assessed in primary cell cultures of striatum, frontal cortex and mesencephalon, containing the substantia nigra or raphe nucleus from the brain of the foetal rat. Chloroform extracts significantly reduced the percentage of live cells whereas the petroleum ether extract was inactive. The ability of the methanol extract to reduce the percentage of live cells could not be distinguished from the effects of the vehicle controls for methanol. Subsequently, the plant material was extracted with dichloromethane and 10 fractions were obtained by column chromatography. Fractions 5, 6, 7 and 8 caused concentration-dependent cell death in the culture of substantia nigra, the other fractions were not toxic at the concentrations used. In further studies, solstitialin A was isolated from fraction 9, solstitialin A 13-acetate from fraction 6 and solstitialin A-3 acetate and cynaropicrin from fraction 7. Solstitialin A 13-acetate and cynaropicrin were toxic to cultures of substantia nigra cells. It is concluded that, of the compounds identified, solstitialin A 13-acetate and cynaropicrin have toxic potential in cell cultures, containing cells from the substantia nigra of the rat, the specificity of action to cells of the substantia nigra remains to be shown, and that a toxic action in the midbrain may contribute to the nigro-pallidal encephalomalacia, caused by the ingestion of the yellow star thistle by horses.

Animals↗