Phytoecdysteroids of Serratula centauroides Herb from Cisbaikalia

Russian Journal of Bioorganic Chemistry - Serratula centauroides L. is a plant species of the Asteraceae family common in Cisbaiklia and containing phytoecdysteroids. As a result of chromatographic...     

Flavonoids from Serratula komarovii Iljin (the Asteraceae Family)

Russian Journal of Bioorganic Chemistry - The genus Serratula L. (the Asteraceae family) is represented by two species in the Russia’s Far East: Serratula manshurica Kitag. and Serratula...     

Phylogenetic relationships of the enigmatic species Serratula chinensis and Serratula forrestii (Asteraceae - Cardueae)

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 2n = 26, and the relationship between this species and the Rhapon-ticum group is discussed from a morphological and karyological point of view.     

Cell Cultures of Ecdysteroid-Containing Ajuga reptansand Serratula coronata Plants

Cell suspension cultures of Ajuga reptans L. and Serratula coronata L. were derived from long-cultured calluses. Their growth patterns and morphophysiological characteristics indicated that these cells adapted well to grow in suspensions. During the growth cycle of cell suspension, the main ecdysteroid, among others present in plants, was 20-hydroxyecdyson (20E) for both cell lines. The content of 20E in cell suspension of A. reptans was 4–8 times higher than in the intact plant. After long culturing, the ecdysteroid profile in cell suspensions of S. coronata (20E, inokosterone, makisterone A, ecdyson, and a nonidentified metabolite) became similar to that of the intact plant. The ecdysteroids accumulated with a periodicity during subculturing cycle.     

A comparative analysis of the proteins from a cell culture and from field plants of the ecdysteroid producer Serratula coronata L.]

Differences in the composition and amount of proteins synthesized in the cell culture and leaves of field plants Serratula coronata have been shown. They proceed from differences in intensity of synthesis of secondary metabolites, ecdysteroids, whose content in the cell culture is considerably lower.     

Ecological relations of agricultural populations of ecdysteroid-containing plants Rhaponticum carthamoides (Willd.) Iljin and Serratula coronata L. to herbivorous insects. Report 1

Accumulation of phytoecdysteroids in agricultural populations of R. carthamoides (Willd.) Iljin and S. coronata L. and their resistance to insect herbivores in different ontogenetic periods were investigated for 16 years. As a result of the investigations, species-specific features of ecdysteroid accumulation in vegetative and reproductive plant organs were determined; relationships between the distribution of phytoecdysteroids in the structure of plants and ecological interactions with insects have been revealed; the factors contributing to insect infestation have been studied; and the pest damage has been evaluated.     

Typifications of Linnaean names in the genus Centaurea and Serratula (Asteraceae)

The typification of three Linnaean names in the genus Centaurea and one in Serratula (Asteraceae): C. lippii (syn. Volutaria lippii), C. muricata (Volutaria muricata), C. repens (Rhaponticum repens) and S. babylonica (Centaurea babylonica), is discussed. Designations of nomenclatural types based on the consultation of Linnaeus's original material and the literature cited in the respective protologues are proposed. Three names are lectotypified using specimens from both Linnaeus herbarium at LINN and the illustrations from Isnard and Dodoëns. Furthermore, a neotype is designated for Serratula babylonica from a specimen at LINN.     

Indole alkaloids from the seeds of Centaurea cyanus (Asteraceae).

Preparative RP-HPLC analysis of a methanol extract of the seeds of Centaurea cyanus afforded four indole alkaloids: moschamine, cis-moschamine, centcyamine and cis-centcyamine, the latter two being new natural products. Structures of these compounds were elucidated by comprehensive spectroscopic analyses. General toxicity of the isolates was determined by Brine Shrimp Lethality bioassay.     

A new Centaurea L. (Asteraceae) species from Turkey

A new Centaurea L. (Asteraceae) species from Turkey is described and illustrated. Centaurea mersinensis Uysal and Hamzao?lu exists on calcareous slopes in Pinus brutia forests of Ayd?nc?k (Mersin) in southern Anatolia. It belongs to C. sect. Phalolepis (Cass.) DC., and taxonomically its closest relative is C. lycaonica. Diagnostic morphological characters from very similar taxa are provided, and a key is provided that includes related species of sect. Phalolepis from Turkey. The geographical distribution of the new species and relatives of the same section are mapped. The chromosome number of C. mersinensis, 2n = 18, counted in root tips, is also reported and illustrated.     

Glyceroglycolipids from Serratula strangulata.

The rhizomes of Serratula strangulata yielded three glyceroglycolipids, i.e. 1,2-di-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-(6-amine-6-deoxy-alpha-D-glucosyl)-glycerol, 1,2-di-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-(6-p-hydroxy-phenyl-propionamido-6-deoxy-alpha-D-glucosyl)-glycerol and 1,2-di-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-[alpha-D-glucose(1-6)-beta-D-allose]-glycerol, as well as a known sesquiterpene lactone and three known phytoecdysones. Their structures were elucidated on the basis of spectral data, especially by 2D NMR spectroscopic methods and chemical conversion. These compounds exhibited significant antibacterial and antitumor activities.     

A new species of Anthemis L. (Asteraceae) from Central Spain

CARRETERO, J. L., 1992. A new species of Anthemis L. (Asteraceae) from Central Spain. A new species of Anthemis is described from the eastern Toledo Mountains. The morphological relationships to other taxa, as well as the chorology and ecology of the new species are presented.     

Mating type of isolates derived from the spermogonial state ofPuccinia coronata var.coronata

Hyphal confrontation between two haploid cultures originating from single basidiospores was used to determine the mating type ofPuccinia coronata var.coronata. Pairs of 15 single-basidiospore cultures were placed approximately 1 mm apart on the medium in all possible combinations. Hyphae of the pairs of colonies came into contact with each other in all combinations approximately two weeks after confrontations. When the nuclear number of hyphal cells in a contact zone was investigated one month after confrontation, monokaryotic hyphae were observed in selfing combination. On the other hand, dikaryotic hyphae were observed in 90.5% of crossing combinations between different cultures. Two isolates are considered compatible if dikaryotic hyphae are present in the contact zone but incompatible if they are absent. The mating type of the fungus was found to be characterized by multiple-allelomorphic tetrapolar incompatibility controlled by the “A” and “B” incompatible factors. Contribution No. 116, Laboratories of Plant Pathology and Mycology, Institute of Agriculture and Forestry, University of Tsukuba     

Chemical Composition of the Tuber Essential Oil from Helianthus tuberosus L. (Asteraceae)

Helianthus tuberosus L. (Jerusalem artichoke) is cultivated in Europe and other parts of the world as a food crop and ornamental plant. The volatile oils of the aerial parts of H. tuberosus were investigated more than 30 years ago, but no study could be found to date on the constituents of the tuber essential oil. Herein, the first characterization by GC‐FID, GC/MS, and ¹³C‐NMR analyses of a hydrodistilled essential oil of Jerusalem artichoke tubers was reported. Fresh plant material collected in Serbia (Sample A) and a commercial sample (Sample B) yielded only small amounts of oil (0.0014 and 0.0021% (w/w), resp.). In total, 195 constituents were identified, representing 88.2 and 93.6% of the oil compositions for Samples A and B, respectively. The main constituents identified were β‐bisabolene ( 1 ; 22.9–30.5%), undecanal (0–12.7%), α‐pinene (7.6–0.8%), kauran‐16‐ol ( 2 ; 6.9–9.8%), 2‐pentylfuran (0.0–5.7%), and (E)‐tetradec‐2‐enal (0.0–4.9%). Several rare compounds characteristic for Helianthus ssp. were also detected: helianthol A ( 6 ; 2.1–1.9%), dihydroeuparin ( 10 ; 0.0–2.3%), euparin ( 9 ; 0.0–0.4%), desmethoxyencecalin ( 7 ; traces – 0.2%), desmethylencecalin ( 8 ; 0.0–0.4%), and an isomer of desmethylencecalin (0.0%‐traces). The essential oils isolated from the tuber and the aerial parts share the common major component 1 .     

Phenolic compounds with antioxidant activity from Anthemis tinctoria L. (Asteraceae)

From the aerial parts of Anthemis tinctoria L. subsp. tinctoria var. pallida DC. (Asteraceae), one new cyclitol glucoside, conduritol F-1-O-(6'-O-E-p-caffeoyl)-beta-D-glucopyranoside (1), has been isolated together with four flavonoids, nicotiflorin (2), isoquercitrin (3), rutin (4) and patulitrin (5). The structures of the isolated compounds were established by means of NMR, MS, and UV spectral analyses. Methanolic extract and pure isolated compounds were examined for their free radical, scavenging activity, using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free stable radical, and for their inhibitory activity toward soybean lipoxygenase, using linoleic acid as substrate. Compounds 1 and 5 showed a strong scavenging effect in the DPPH radical assay. In addition 5 also exhibited high inhibitory activity on soybean lipoxygenase.     

A new species of Centaurea L. (Cardueae: Asteraceae) from Turkey

A new species of Centaurea L., C. kizildaghensis (Cardueae: Asteraceae), is described and illustrated from south Anatolia. It is restricted to the serpentine rocky slopes of Kızıl Dağ (C3 Konya–Derebucak, Çamlık), and is closely related to C. pseudokotschyi Wagenitz and C. drabifolioides Hub.-Mor., from which it differs in stem, leaf, and phyllary appendage characters. The diagnostic morphological characters are discussed. A new key is produced for Group G species for the flora of Turkey.  © 2007 The Linnean Society of London, Botanical Journal of the Linnean Society , 2007, 153 , 61–66.     

Phytochemical and Cytogenetic Characterization of Centaurea solstitialis L. (Asteraceae) from Croatia

The cytogenetic characterization of Centaurea solstitialis L. (Asteraceae) showed a chromosome number of 2n = 16. Karyotype is composed by four pairs of metacentric, two pairs of submetacentric and two pairs of subtelocentric chromosomes. Physical mapping of two rDNA probes revealed two loci of 35S and one locus of 5S rRNA genes. Chromomycin fluorochrome banding revealed that all rDNA loci were GC rich. The genome size (2C‐value) of 1.95 pg classes this species in the group of very small genomes. Chemical composition of C. solstitialis volatile oil (VO) from Croatia, studied with gas chromatography–mass spectrometry showed dominant components as it follows: hexadecanoic acid, α‐linolenic acid, germacrene D and heptacosane. Antioxidant capacity, measured by ferric reducing power assay and 2,2‐diphenyl‐1‐picrylhydrazyl methods, as well as inhibition of acetyl‐ and butyrylcholinesterase of VO was lower comparing to a standard solutions. Volatile oil tested with disc diffusion method showed good inhibitory potential against Pseudomonas aeruginosa, Escherichia coli and all tested fungi: Candida albicans, Penicillium funiculosum and Aspergillus fumigatus. The microdilution method showed best activity against Chronobacter sakazakii and A. fumigatus.     

Natural products from Tolpis barbata (L.) Gaertn. (Asteraceae,Cichorieae)

One sesquiterpene lactone – 9α-hydroxy-3-deoxyzaluzanin C, three benzopyrans: desmethoxyencecalin (6-acetyl-2,2-dimethylchromene), desacetylripariochromen B and 6-(1-hydroxyethyl)-2,2-dimethylchromene, one coumarin – scopoletin and two eugenol derivatives were isolated from the roots of Tolpis barbata (L.) Gaertn, hitherto unexamined species. In the extract from aerial parts of the plant, five known phenolic compounds, namely: esculin, esculetin, chlorogenic acid (5-CQA), luteolin 7-O-glucoside and 3,5-dicaffeoylquinic acid (3,5-DCQA) were identified as major constituents. Except for the two coumarins – scopoletin and esculetin, which were previously obtained from Tolpis webbii Sch.Bip. and T. proustii Pit., the isolated and identified compounds have not been previously reported as constituents of Tolpis spp. Though benzopyrans were found in numerous species of the Asteraceae, their occurrence in the tribe Cichorieae has not been demonstrated before.     

Secondo Contributo Alla Conoscenza Dello Sviluppo Embriologico del Genere Centaurea L. (Asteraceae). Centaurea Horrida Bad

Summary

The Author has studied the embryological development of Centaurea horrida Bad., pure pliocenic endemisms of Sardinia and has established that:

1°) the cromosomic number of the species is: 2n = 18.

2°) the genesis of microspores is of simultaneous type;

3°) The archesporium is constituted of one cell only seldom accompanied by a basal cell;

4°) the development of the female gamethophyte is of normal type;

5°) even showing cases of degenerated antipodal cells, the species has a marked tendency to the polyantipody, sometimes also characterized by a strong hypertrophy of its cells;

6°) in the species the contemporary germination of some megaspores in the same ovule is enough frequent;

7°) there are also some cases of coesistence of some gamethophytes in their different stages of development;

8°) the phenomenon of «multiple oospheres» and of «multiple synergidae» may happen;

9°) in some ovules, near the egg-apparatus, cells of two or four nuclei may be found.

For these last ascertainments (8° and 9°) the Author makes the hypothesis that it may be probably an anomalous prolification of micropylar nuclei, or asynchronous development, for delayed germination of some micropylar megaspores producing primary stages of gamethophyte.

Moreover the Author has the opportunity to bring into evidence:

10°) a case of ovular teratology represented by the extraovular development of an adult gamethophyte very similar to those previously found by the Author himself in Petasites fragrans;

11°) frequent cases of regretion of female sexuality, founding that about the 10% of the flowers examined were functionally male. The Author has fronted the possibility of the existence, in Asteraceae, also of the type of inflorescence where «flowers are all tubulated: the marginal ones neuter, the others or hermaphrodite or hermaphrodite and male».     

Phytotoxic Potential of Onopordum acanthium L. (Asteraceae)

Onopordum acanthium L. (Asteraceae) is a plant native to southern Europe and southwestern Asia, but it is invasive in disturbed areas and agricultural fields around the world, causing many agronomic problems by interfering with crops or preventing animals from grazing on pastures. Allelopathy could be one of the reasons that this plant has spread over different continents. The aim of the present study was to bioprospect O. acanthium leaf extracts through the isolation and purification of allelopathic secondary metabolites with phytotoxicity to explain their invasive behavior. Phytotoxic activity was tested using etiolated wheat coleoptiles. The most active extract was selected to perform a bioassay‐guided isolation of two flavonoids, pectolarigenin ( 1 ) and scutellarein 4′‐methyl ether ( 2 ), and two sesquiterpene lactones, elemanolide 11(13)‐dehydromelitensin β‐hydroxyisobutyrate ( 3 ) and acanthiolide ( 4 ). All compounds were isolated for the first time from O. acanthium, and acanthiolide ( 4 ) is described for the first time. Compound 3 strongly inhibited the growth of wheat coleoptiles and 1 showed an intermediate effect. The results indicate that these compounds could contribute to the invasion of O. acanthium in ecological systems and agricultural fields.