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At least 19 recordsLinked to original sources
PubMed2000

Sesquiterpene lactones from Centaurea thessala and Centaurea attica. Antifungal activity.

The aerial parts of Centaurea thessala ssp. drakiensis and C. attica ssp. attica afforded, in addition to several known sesquiterpene lactones, two new eudesmanolides, 4-epi-sonchucarpolide and its 8-(3-hydroxy-4-acetoxy-2-methylene-butanoyloxy) derivative and one new eudesmane derivative, named atticin. The in vitro antifungal activity of most compounds was tested against nine fungal species, using the micro-dilution method. All the compounds tested showed great antifungal activity.

Antifungal Agents↗
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↗
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↗
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↗
PubMed1994

Cellular protein receptors of maculosin, a host specific phytotoxin of spotted knapweed (Centaurea maculosa L.).

Maculosin (the diketopiperazine, cyclo (L-Pro-L-Tyr)) is a host specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa L.). Receptors for this phytotoxin have been isolated from spotted knapweed. Knapweed leaves possess most of the maculosin-binding activity in the cytosolic fraction. However, activity was also observed in the whole membrane fraction of the leaf. The binding component of the cytosolic fraction was identified as a protein(s) because of its heat-lability and sensitivity to proteases. A 16-fold purification of a toxin-binding protein was carried out by ammonium sulfate fractionation, and Sephadex G-200, and maculosin-affinity column chromatography. The affinity column was prepared with epoxy activated Sepharose 6B to which the phenolic group of maculosin was attached. The receptor was estimated to contain more than one binding protein by native and SDS-PAGE. At least one of the maculosin-binding proteins was identified as ribulose-1,5-biphosphate carboxylase (RuBPcase).

Binding Sites↗
PubMed1983

Some pharmacological, toxicological and phytochemical investigations on Centaurea phyllocephala.

Centaurea phyllocephala Boiss. has been used in folkloric medicine as an antidiabetic agent. Present investigations on various extracts of C. phyllocephala revealed that basal plasma glucose concentration and plasma glucose response to glucose load were either elevated or unchanged by the i.v. administration of these extracts in anaesthetized rats or by i.p. or oral administration of the extracts in conscious rats. The predominant effect of C. phyllocephala is the toxicity in rats and mice and this indicates the presence of some toxic or active compounds which merit phytochemical isolation. Further, C. phyllocephala extracts also caused either an initial brief hypotension followed by a delayed hypertension or produced no changes when injected i.v. in the rats. The hypotensive effect was inhibited by atropine whereas the hypertensive effect was prevented by phentolamine or guanethidine but not by hexamethonium. The alcoholic extract also induced an initial brief negative inotropic effect, followed by delayed prolonged positive inotropic and negative chronotropic effects on the spontaneous inotropic and negative chronotropic effects on the spontaneous contractions of the guinea pig right atrium. The initial depressing effect and the delayed positive inotropic effect were inhibited by pretreatment with atropine. The extract of C. phyllocephala also produced a contractile activity on guinea pig ileum strips and this could be prevented by atropine. No significant diuretic effect was produced by the extract. Phytochemical screening revealed that C. phyllocephala contains tertiary and quaternary alkaloids, sesquiterpene lactones, methylated flavones and their glycosides, as well as leuco- and proanthocyanidines. Further studies on sesquiterpene lactones and methylated flavones resulted in the isolation of lactones with alpha-methylene gamma-lactone and methylene side chain on the cyclopentyl ring as well as of four methylated flavones (hispidulin, nepetin, cirsiliol, jaceosidin) structurally closely related to the cytotoxic flavonoids of other Compositae plants.

Animals↗
PubMed1993

Two new antiinflammatory elemanolides from Centaurea chilensis.

Two previously undescribed elemanolide esters, the 2-methylpropanoate and 2-methyl-2-propenoate of 11,13-dehydromelitensin, were isolated in the course of a bioassay-guided fractionation from the aerial parts of Centaurea chilensis Hook. et Arn., used traditionally to treat 'gout and rheumatism'. The mixture of both substances exhibits anti-inflammatory activity in the carrageenan-induced paw edema assay.

Animals↗
PubMed2001

Two flavonoids and other compounds from the aerial parts of Centaurea bracteata from Italy.

The flowering aerial parts of Centaurea bracteata Scop. (Asteraceae) have been studied for the first time. Nineteen compounds were isolated and identified, namely a sterol glucoside, two phenolic acids, three quinic acid derivatives, and 13 flavonoids, two of which, are new natural products. Structural elucidation was performed mainly by mean of FABMS, 1D and 2D NMR spectroscopy.

Asteraceae↗
PubMed2001

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.

Alkaloids↗
PubMed2001

A flavonoid sulphate and other compounds from the roots of Centaurea bracteata.

The roots of Centaurea bracteata Scop. (Asteraceae) have been studied for the first time. Twenty-three compounds were isolated and identified, namely a sterol glucoside, two quinic acid derivatives, one sugar, and 19 flavonoids (five sulphates), one of which, centaradixin, resulted in a new natural product. Structural elucidation was performed mainly by means of FABMS, 1D and 2D NMR spectroscopy. NMR data of some sulphate flavonoids are reported for the first time.

Asteraceae↗
PubMed1998

Sesquiterpene lactones of Centaurea scoparia.

From the ethanolic extract of the aerial parts of Centaurea scoparia four new sesquiterpene lactones, belonging to the guaiane class, were isolated and identified, together with a known germacranolide. The structures were elucidated by spectroscopic methods including one- and two-dimensional NMR studies. The relative configuration was deduced from the 2D NOESY spectra. CD spectroscopy of the chlorinated compounds was used for determination of their absolute configuration.

Journal Article↗
PubMed1999

Guaianolides from Centaurea nicolai: antifungal activity.

A new guaianolide, 3-deacetyl-9-O-acetylsalograviolide A, along with four known closely related lactones, salograviolide A, 9-O-acetylsalograviolide A, kandavanolide and salograviolide B were detected in the aerial parts of the flowering plant Centaurea nicolai. Antifungal tests performed on salograviolide A and its 9-O-acetyl and 3-O-deacetyl-9-O-acetyl derivatives revealed inhibitory activity against Aspergillus niger, A. ochraceus, Penicillium ochrochloron, Cladosporium cladosporoides, Fusarium tricinctum and Phomopsis helianthi. Neither of them was active against Trichoderma viride.

Antifungal Agents↗
PubMed1997

Inhibition of tomato bushy stunt virus infection using a quercetagetin flavonoid isolated from Centaurea rupestris L.

Flower and leaf extracts of Centaurea rupestris L. and also the flavonoid quercetagetin 3'-methylether isolated from these extracts revealed a strong antiviral activity when inoculated simultaneously with tomato bushy stunt virus in two Nicotiana species. Almost complete reduction of local lesion number resulted from these inoculations in N. glutinosa. A similar effect was observed in inoculated leaves of N. megalosiphon causing the absence of systemic infection in 40% of treated plants. The antiphytoviral activity was not a consequence of induced resistance, inhibition of virus multiplication, suppression of symptom development or direct virus inactivation. Results presented in this paper suggest that the flavonoid may interfere with the initiation of virus infection.

Antiviral Agents↗
PubMed2001

Sesquiterpene lactones from Centaurea tweediei.

Aerial parts of Centaurea tweediei from Argentina afforded as the main constituent the sesquiterpene lactone onopordopicrin and minor amounts of a new heliangolide, a new guaianolide, a new eudesmanolide, a new eudesmane acid and the lignans arctigenin and matairesinol.

Journal Article↗