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The chemical study of Centaurea granatensis Boiss. ex DC. allowed the isolation and structural elucidation of eighteen secondary metabolites (1 – 18) from ethyl acetate (EtOAc) and n -butanol (n -BuOH) extracts. These compounds are divided into one new epoxylignan glucoside (1) and seventeen known phytochemicals including seven flavonoids (2 – 8) , four triterpenes (9 – 12) , and six phytosterols (13 – 18). Structures of the isolates were identified using various spectroscopic methods, namely 1D NMR (1H and 13C), 2D NMR (HSQC, 1H–1H COSY, HMBC, and NOESY), and mass spectrometry (HR-ESIMS), as well as by comparison with literature data. The obtained results showed the abundance of triterpenoids and flavonoids particularly flavones in C. granatensis. Apigenin (3) could be used as a chemotaxonomic marker of this genus due to its presence in approximately forty plant species. Furthermore, tiliroside (2) and stigmasteryl-3- O - β -D-glucoside-6′-palmitate (18) were first detected in Centaurea genus, but had previously been found in species of the Asteraceae family. Additionally, the chemotaxonomic significance of all isolated molecules was fully discussed. [Display omitted] • A chemical investigation on Centaurea granatensis Boiss. ex DC. was performed. • Flavonoids, lignans, triterpenes and phytosterols have been isolated. • A new 7,9′-monoepoxylignan glucoside along with 17 known compounds were identified. • Chemotaxonomic importance of isolates has been fully discussed. [ABSTRACT FROM AUTHOR]

Here we describe Centaurea hekimhanensis, a new species found in Hekimhan (Turkey, Malatya Province). This Centaurea grows on the stony-gravel mountain slopes of Yamadağ and is morphologically similar to C. reuteriana, C. bourgaei, and C. pichleri in terms of their flowering lateral stem at the base of the rosette, but differs regarding the shape of the stem and rosette leaves, and the size of the rosette leaves and median appendages; the achene ornamentation is irregularly sulcate. The chromosome number of the new species is 2n = 20.

A new endemic species, Centaurodendron schilleri, is described from the Juan Fernández Archipelago, Chile. This is the third species of the endemic genus, Centaurodendron, which is closely related to Plectocephalus of the Chilean mainland. The new species is confined to Alejandro Selkirk Island, whereas the previously known species, C. dracaenoides and C. palmiforme, are confined to Robinson Crusoe Island. In morphological aspects, the new species is more distinct from the other two species than they are from each other. Molecular phylogenetic and biogeographic studies for island and continental species of these genera are in progress.

Two new species of Centaurea subg. Cyanus (Asteraceae) from Anatolia are described and illustrated. Centaurea akcadaghensis Uysal & Şirin occurs on open Quercus forest of Levent Canyon (Akçadağ-Malatya) and differs from C. matthiolifolia Boiss. mainly in stem, leaves, central flowers and achenes measures. Centaurea ermenekensis Şirin & Uysal is restricted to steppes of Göktepe (Ermenek-Karaman) and can be distinguished from C. reuteriana Boiss. by the stem, number of capitula, involucre and median appendages measures.

The current investigations suggest the segregation of Jurinea cartilaginea from Jurinea, and its placement among Centaureinae. Molecular studies, based on the nuclear ribosomal internal transcribed spacers (nrITS), chromosome number data and pollen morphology, support the morphological results. Based on these results, J. cartilaginea is related to and, therefore, transferred to the genus Karvandarina. Due to the morphological characters differing from Karvanderina aphylla, a new subgenus, Pseudojurinea, is described. Molecular study also supports the monophyly of Jurinea.

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Centaurea uysalii Şirin & Çeçen, a new Asteraceae species from the province of Karaman, in Turkey, is described and illustrated herein. It is morphologically similar to C. bourgaei Boiss. (Subgen. Cyanus), but it mainly differs from its relative in terms of the involucre and achene lengths. The achene micromorphological features and karyomorphology of C. uysalii and C. bourgaei were examined in this study. The IUCN conservation status is the Critically Endangered [CR B2 a b (i, iii)] category. [ABSTRACT FROM AUTHOR]

In this paper, we investigated a set of narrow endemics of Centaurea subsect. Phalolepis from the mountains of South Italy (mainly Calabria and Salento), segregated from the widespread species Centaurea deusta, using microsatellite (SSR) markers. The goal was to analyse the genetic makeup (levels and structure) of C. deusta and the segregated species and verify whether genetic clusters were in agreement with current classification of the species. With C. deusta, we also carried out an ecological niche modelling (ENM) analysis to check its potential distribution under present climatic conditions and to project it to the Last Glacial Maximum (LGM). As also found in former studies with subsect. Phalolepis in Greece and Turkey using the same set of SSRs, genetic diversity for the segregated Italian species was higher than expected for narrow endemics with small populations. Genetic clusters, however, were not correlated with the described species and did not support the segregation of the purported narrow endemics from a widely defined C. deusta. The results of the ENM indicate that the Adriatic Sea was a migration corridor for C. deusta at the LGM. [ABSTRACT FROM AUTHOR]

In the frames of our research on the genus Jurinea (Carduinae), the taxonomic status of some species has been checked. In this study, evidences are presented to support transferring the species Jurinea gedrosiaca to Tricholepis, a genus in Centaureinae. Furthermore, it is demonstrated that J. gedrosiaca is conspecific with T. edmondsonii described around 40 years later. Consequently, the correct name of the taxon is Tricholepis gedrosiaca, and the respective combination is presented. An improved description, photos and distribution map of the species are also provided. [ABSTRACT FROM AUTHOR]

The presence of cynaropicrin was determined in 13 species of the subtribe Centaureinae Dumort.: Centaurea declinata M. B.- C. leucophylla M. B.. C. dealbata Willd.. C. zangezuri (Sosn.) Sosn., C. carthalinica (Sosn.) Sosn., C. thracica (Janka) Hayek, C. exarata Boiss. ex Cosson, C. phaeopappoides Bordz., Chartolepis intermedia Bioss., Ch. glastifolia (L.) Cass., Rhaponticum carthamoides (Willd.) Iljin, Rh. serratuloides (Georgi) Bobr., Leuzea rhapontica (L.) Holub.

Differences in the composition of the "lactone fraction" of 4 species from the genus Chartolepis Cass. were observed. Cynaropierin was isolated from the above-ground parts of Chartolepis intermedia Boiss. and the occurrence there of grossheimin was confirmed. The following compounds were isolated from the above-ground parts of Chartolepis glastifolia (L.) Cass.: centaurepensin, repin, cebellin C, acroptillin, cebellin D, cynaropicrin, cebellin F and janerin. Centaurepensin, repin, cebellin C, acroptillin, cynaropicrin, janerin and a new guaianolide, pterocaulin were isolated from the herb Chartolepis biebersteinii Jaub. et Spach. In addition to the lactones found in Chartolepis biebersteinii, Chartolepis pterocaula (Trautv.) Czer. also accumulated grossheimin.

A new species of Cyanus Mill. (Centaurea L. p.p.) (Asteraceae), Cyanus banchevae Kaya, is described and illustrated from Bolu province, Turkey. It belongs to section Napuliferae (Stef. & Georgiev) Bancheva & Raimondo and taxonomically its closest relative is C. thirkei Scultz Bip. The habitat and conservation status of the species are presented, and the geographical distribution of the new species and its closest relatives is discussed. [ABSTRACT FROM AUTHOR]

Genus Serratula is known for the presence of steroid compounds which belong to the group of ecdysones. Former phytochemical works from the late sixties and early seventies indicate, in some Serratula species, the occurrence of a phenolic glycoside-arbutin. This has been confirmed in the present work through finding an α,β-arbutin anomer in Serratula quinquefolia M.B. New botanical data concerning the classification of genus Serratula suggest that the species in question should be regarded as belonging to genus Klasea (currently a section of genus Serratula). There has been an attempt to find a key to the chemical division within the taxons.

Se estudian los caracteres morfoanatómicos de 32 especies del complejo Carduncellus-Carthamus y se debate la evolución de estos caracteres y su utilidad para la delimitación genérica de este complejo, comparándola con la filogenia obtenida de las secuencias del DNA ribosómico nuclear.

The occurrence of syringin in eight out of ten investigated plant species of the subtribe Centaureinae (Asteraceae) was reported. The compound was isolated from aerial parts of the plants by silica gel column chromatography of methanol extracts. Contents of syringin varied from 0.001 to 0.1% of the dried plant material. Centaurea bella Trautv. appeared to be the best source of this compound (0.1% dry wt.). Syringin has been reported for the first time from these plant species.

Background and Aims Subtribe Centaureinae appears to be an excellent model group in which to analyse satellite DNA and assess the influence that the biology and/or the evolution of different lineages have had on the evolution of this class of repetitive DNA. Phylogenetic analyses of Centaureinae support two main phases of radiation, leading to two major groups of genera of different ages. Furthermore, different modes of evolution are observed in different lineages, reflected by morphology and DNA sequences. Methods The sequences of 502 repeat units of the HinfI satellite DNA family from 38 species belonging to ten genera of Centaureinae were isolated and compared. A phylogenetic reconstruction was carried out by maximum likelihood and Bayesian inference. Key Results Up to eight different HinfI subfamilies were found, based on the presence of a set of diagnostic positions given by a specific mutation shared by all the sequences of one group. Subfamilies V–VIII were mostly found in older genera (first phase of radiation in the subtribe, late Oligocene–Miocene), although some copies of these types of repeats were also found in some species of the derived genera. Subfamilies I–IV spread mostly in species of the derived clade (second phase of radiation, Pliocene to Pleistocene), although repeats of these subfamilies exist in older species. Phylogenetic trees did not group the repeats by taxonomic affinity, but sequences were grouped by subfamily provenance. Concerted evolution was observed in HinfI subfamilies spread in older genera, whereas no genetic differentiation was found between species, and several subfamilies even coexist within the same species, in recently radiated groups or in groups with a history of recurrent hybridization of lineages. Conclusions The results suggest that the eight HinfI subfamilies were present in the common ancestor of Centaureinae and that each spread differentially in different genera during the two main phases of radiation following the library model of satellite DNA evolution. Additionally, differential speciation pathways gave rise to differential patterns of sequence evolution in different lineages. Thus, the evolutionary history of each group of Centaureinae is reflected in HinfI satellite DNA evolution. The data reinforce the value of satellite DNA sequences as markers of evolutionary processes. [ABSTRACT FROM AUTHOR]

Abstract: Asteraceae Bercht. & J. Presl is one of the biggest and most economically important plant families. The taxonomy and phylogeny of Asteraceae is rather complex and according to the latest and most reliable taxonomic classification of Panero & Funk, based on the analysis of nine chloroplast regions, the family is divided into 12 subfamilies and 35 tribes. One of the largest tribes of Asteraceae is Cardueae Cass. with four subtribes (Carlininae, Echinopinae, Carduinae and Centaureinae) and more than 2500 species. Susanna & Garcia-Jacas have organized the genera of Centaureinae (about 800 species) into seven informal groups, which recent molecular studies have confirmed: 1. Basal genera; 2. Volutaria group; 3. Rhaponticum group; 4. Serratula group; 5. Carthamus group; 6. Crocodylium group; 7. Centaurea group. This review summarizes reports on sesquiterpenoids from the Centaureinae subtribe of the Asteraceae family, as well as the 13C NMR spectral data described in the literature. It further reviews studies concerning the biological activities of these metabolites. For this work, literature data on sesquiterpenes from the Centaureinae subtribe were retrieved with the help of the SciFinder database and other similar data banks. All entries from 1958 until the end of 2011 were considered. This review is addressed to scientists working in the metabolomics field such as chemists, botanists, etc., the spectroscopic data reported make this work a good tool for structural elucidation, the biological section gives useful information to those who wish to study the structure activity relationships. [Copyright &y& Elsevier]

Background and Aims The geographic distribution of the genus Plectocephalus comprises a single species in Ethiopia, two in North America and possibly four more in South America, in a striking disjunction that is exceptional for genera of the tribe Cardueae. The enormity of this disjunction cast doubts on the precise taxonomic delineation of the genus, which is not unanimously recognized as a natural entity. The aims of this study were to define the generic boundaries of Plectocephalus and to formulate a hypothesis that would explain its natural range. Methods A combined molecular approach, using nuclear internal transcribed spacers (ITS) and external transcribed spacers (ETS), and plastid trnL-trnL-F, rpl32-trnLUAG and ndhF markers, was chosen for phylogenetic reconstruction by maximum parsimony and Bayesian inference. Key Results Phylogenetic analysis shows that Plectocephalus is a natural genus that includes the African species P. varians, together with all the native South American species, currently classified as Centaurea, C. cachinalensis, C. floccosa and C. tweediei. The recognition of Centaurodendron as an independent genus, which we consider appropriate, would make Plectocephalus paraphyletic. Affinities of Plectocephalus should lie with eastern representatives of Centaureinae. Geographic disjunction is explained as a consequence of dispersal via the Bering Land Bridge during the Miocene–Pliocene. The phylogeny of the basal grade of Centaureinae differs from previous phylogenies, and artefacts resulting from differences in mutation rates of annual and perennial taxa are confirmed. Sensitivity of ITS to these differences was the highest observed for all DNA regions used in this study. Conclusions The natural status of the genus Plectocephalus is confirmed and several nomenclatural combinations are proposed. New evidence contributes to the debate concerning problems posed by the use of ITS in the phylogenetic reconstruction of groups that differ in terms of their life cycles. Dispersal from Caucasus and Anatolia along the Siberian route and then across the Bering Land Bridge follows a route previously proposed for other taxonomic groups. [ABSTRACT FROM AUTHOR]

Twenty-two chromosome counts are reported in 16 species, four subspecies and two varieties of the genus Centaurea. These are mostly Turkish local endemics of section Cheirolepis, a complicated group from the Eastern clade of the Jacea group. Twenty-one reports are new. Prevalence of the basic chromosome number x = 9 among the eastern sections of the Jacea group is confirmed. © 2009 The Linnean Society of London, Botanical Journal of the Linnean Society, 2009, 159, 280–286. [ABSTRACT FROM AUTHOR]

Turkish representatives of the genus Rhaponticoides Vaill. are examined. A key and distribution map of Rhaponticoides species occurring in Turkey are provided for the first time. R. hierroi Ö. Eren sp. nov., from Bakacak pass in the Western Taurus range, SW Anatolia, allied to R. mykalea (Hub.-Mor.) M. V. Agab. & Greuter is described as a species new to science and illustrated. Its habitat conditions and conservation status are considered. Pollen micrographs of R. hierroi and R. mykalea are presented using scanning electron microscopy. [ABSTRACT FROM AUTHOR]

Chromosome counts are reported in 29 populations representing 20 species and one subspecies of the genera Callicephalus (one sp.), Klasea (seven spp.), Myopordon (two spp.), Oligochaeta (one sp.), and Rhaponticum (nine spp., one ssp.). Eleven reports are new, the others supplement limited previous data. New and published cytological data are summarized and evaluated critically in light of current taxonomic treatments and evolutionary hypotheses. Basic chromosome numbers are a valuable source of taxonomic information and relate well to the phylogeny. They are quite conserved in Klasea (only x = 15), the sister group of the remaining genera, and in the early branching genera of the Rhaponticum group ( x = 14 for Centaurothamnus and Callicephalus). However, a more complex pattern of genome evolution is present among the more derived clades, Oligochaeta plus Myopordon ( x = 12, 14) and the genus Rhaponticum ( x = 12, 13). The occurrence of x = 12 in Oligochaeta divaricata and Rhaponticum carthamoides seems to be the result of a recent event of chromosome fusion, as suggested by the fragility of particularly long pairs of chromosomes. The use of chromomycin staining, including an enzymatic digestion step that facilitates spreading and permits a reduction of potential fragmentation, only partially resolves this problem. © 2007 The Linnean Society of London, Botanical Journal of the Linnean Society, 2007, 153, 193–201. [ABSTRACT FROM AUTHOR]

Klasea, traditionally treated as a section in Serratula, is now widely accepted at the generic level. A classification of the genus is presented here, accommodating the 46 species in ten sections based on nuclear ribosomal DNA external and internal transcribed spacer sequence data and morphology. New combinations for five species and ten subspecies are published, and a new hybrid species is described. The genus ranges from the Iberian Peninsula and north Africa through southern and eastern Europe, west and central Asia to the Himalayas, and the Far East of Russia and China. The ancestral area is in west Asia, most probably eastern Anatolia and northern and western Iran. In this region, representatives of all sections are present. The largest section Klasea diversified most likely in the mountains of central Asia. A key to all Klasea species is provided. © 2006 The Linnean Society of London, Botanical Journal of the Linnean Society, 2006, 152, 435–464. [ABSTRACT FROM AUTHOR]

Serratula chinensis and S. forrestii, both endemic to China, have been shown to be phylogenetically separated from all other species of Serratula and from each other in a previous molecular analysis, and are placed in the newly described genera Kiaseopsis and Archiserratula, respectively. Full descriptions including illustrations are presented. [ABSTRACT FROM AUTHOR]

• 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. [ABSTRACT FROM AUTHOR]

The phylogenetic relationships of the Chinese species Serratula forrestii and S. chinensis within the subtribe Centaureinae (Asteraceae – Cardueae) were investigated based on nuclear ribosomal DNA external and internal transcribed spacer sequences. Results indicated that Serratula s. l. is clearly polyphyletic, none of the two species showing close affinities to either Serratula s. str. or Klasea, a genus traditionally included in Serratula. Serratula forrestii has a basal position within the subtribe and has retained most plesiomorphic character states. Serratula chinensis is related to the genera of the Rhaponticum group. Its chromosome number was determined as 2 n = 26, and the relationship between this species and the Rhapon-ticum group is discussed from a morphological and karyological point of view. [ABSTRACT FROM AUTHOR]

Recent molecular studies have clarified the problem of the generic limits ofCarthamus. However, taxonomic problems remain in the sectional classification: sectionCarthamuswas confirmed as a natural group, but molecular phylogenies based on DNA sequences did not resolve the other sections, resulting in a confusing conglomerate. A survey based on RAPD markers has been carried out in this conflicting group of sections, with the aim of evaluating the usefulness of these markers at the section and species levels. On the basis of the results, correlated with morphological and karyological characters, some recommendations are made in relation to the taxonomy ofCarthamus. The number of sections is reduced from five to two: sectionThamnacanthusis currently classified as a different genus,Phonus; sectionCarthamus s.s.is retained in its present delimitation, and sectionAtractylisis redefined, including current sectionsAtractylis,LepidopappusandOdontagnathius. The commonly accepted treatment of some taxa as subspecies is not well founded, andC. alexandrinus,C. creticus,C. tenuisandC. turkestanicusshould be considered as independent species. Our results confirm that methodological problems posed by RAPD markers can be avoided by careful laboratory procedures and appropriate data analyses; they also suggest that this kind of marker is useful at low taxonomic levels and is, furthermore, complementary to DNA sequence analysis. © 2005 The Linnean Society of London,Botanical Journal of the Linnean Society, 2005,147, 375–383. [ABSTRACT FROM AUTHOR]

The ecogeographical history of Cardueae-Centaureinae (Asteraceae) in the Mediterranean is discussed on the background of the geological history of the region. Two main phases of radiation are postulated. The first one separated the basal groups of the subtribe (Klasea group, Rhaponticoides/Cheirolophus group, Rhaponticum group, Amberboa group, Psephellus, and Plectocephalus). This happened during late Oligocene and Miocene. The major modern or derived clades (Centaurea, Colymbada group, Cyanus and Carthamus/Carduncellus group) may have differentiated around the transition from Pliocene to Pleistocene. Aridisation favoured the development of biennial and annual species independently in different groups. Different modes of evolution are observed in annual and perennial species, reflected by morphology as well as DNA sequences. The myrmekochory syndrome, adaptation to man-made habitats, chromosome and genome evolution, and modes of reproduction receive special attention. [ABSTRACT FROM AUTHOR]

Twenty-seven chromosome counts are reported in 23 species of the genus Centaurea, mostly eastern endemic species of the Jacea group, which has become the core of the re-defined genus Centaurea. Twenty reports are new, one is a correction of a previous count, one is a confirmation of limited previous data and one represents a new basic number in the Centaureinae. The prevalence of the basic chromosome number x = 9 among the Eastern sections of the Jacea group is confirmed, together with the close correlation between karyological data and classification of the genus. Two alternative hypotheses on the aberrant chromosome number (for the Centaureinae) found in C. behen are proposed. One of them, if verified, would confirm that a cycle of polyploidy and descending dysploidy is a key mechanism in the speciation of the group. © 2004 The Linnean Society of London, Botanical Journal of the Linnean Society, 2004, 145, 345–352. [ABSTRACT FROM AUTHOR]

A new species of Centaurea L. (Asteraceae), Centaurea yildiziiŞ. Civelek, İ. Türko&gcaron;lu & H. Akan (sect. Psephelloideae (Boiss.)) Sosn. is described from Turkey. Diagnostic characters, a description, detailed illustrations and taxonomic comments on the species are given. It is compared with the closely related taxon, Centaurea pyrrhoblephara Boiss. The geographical distribution of the new species and other related species is mapped. © 2003 The Linnean Society of London, Botanical Journal of the Linnean Society, 2003, 143, 207–212. [ABSTRACT FROM AUTHOR]

The genus Rhaponticoides , recently segregated from the genus Centaurea , belongs to the family Asteraceae (tribe Cardueae). Rhaponticoides mykalea (Hub.-Mor.) M.V.Agab. & Greuter is an endemic species narrowly distributed in the Aegean part of Turkey. Owing to the existing anthropogenic impacts (such as urbanization and road construction) throughout its distribution range, the species has been the subject of several conservation studies. Phytochemical research on the aerial parts of R. mykalea led to the isolation of a new flavonoid, namely patuletin 7- O -(6″- E -sinapyl)-β-glucopyranoside, together with four known flavonoids from n -butanol extract. The structures of all isolated compounds were elucidated by spectroscopic analysis (1D and 2D NMR, HR-ESI-MS), as well as by comparison with the relevant literature data. All of the compounds have been isolated from the genus Rhaponticoides for the first time. Rhaponticoides mykalea (Hub.-Mor.) M.V. Agab.&Greuter. [Display omitted] • Rhaponticoides mykalea is an endemic and critically endangered species with little known phytochemistry. • One new acylated flavonol and four known flavonol glycosides were isolated and identified from the aerial parts. • All of the compounds were isolated from Rhaponticoides mykalea for the first time. • This study provides important contributions to the understanding of the chemistry of the genus Rhaponticoides. [ABSTRACT FROM AUTHOR]