Achillea Nobilis Research Articles

Synthesis and Biological Activity of Estafiatin Phosphonate Derivatives

Four new dialkylphosphonate derivatives 2–5 were prepared for the first time from the guaiane-type sesquiterpene lactone estafiatin (1), which was isolated from the aerial part of Achillea nobilis. Their structures were elucidated using PMR, 13C NMR, two-dimensional 1H–1H COSY, 13C–1H COLOC, and 31P–1H spectroscopy. The estafiatin phosphorylation reaction was highly chemo- and stereoselective. The antimicrobial activity of the prepared derivatives was studied.

Determination of allelopathic potential in some medicinal and wild plant species of Iran by dish pack method

Plants have the ability to interfere with other organisms in their immediate environment, a phenomenon called allelopathy. Allelopathy is a common phenomenon in nature (Qian Chemosphere 75(368):375, 2009). The use of allelopathic compounds for the development of new agrochemicals has several benefits as opposed to common synthetic products. Cognizant of reports on the allelopathic action of medicinal and invasive plants, 118 Iranian plants from 104 species which belongs to 34 families have been screened for allelopathic volatiles by the dish pack method. A total of 118 plants (104 species) belonging to 34 families were collected in 2009 from the tropical, subtropical and temperate regions of Iran. The Dish pack method as described by Fujii et al. (Weed Sci Technol 45(80):81, 2000) utilized for screening the presence of allelopathic volatiles released from different parts of the plant specimen. This method can be used to recognize allelopathic properties very easy and quickly. Results of bioassay with lettuce seed (Lactuca sativa cv. Great Lakes 366) revealed that 23 species elicited growth inhibitory action with the greatest (≥96% reduction) observed in the inflorescences of Achillea wilhelmsii and Achillea filipendula. Furthermore, a high suppression (83–95 %) in radicle elongation was observed in lettuce exposed to: flowers of Achillea nobilis, Lavandula vera, and Perovskia abrotanoides; fruit of Ruta graveolens; seeds of Bunium persicum and Trachyspermum copticum; leaves of Achillea biebersteinii, Pulicaria gnaphalodes, Ziziphora clinopodioides, Zataria multiflora; gum of Ferula foetida; and stigma of Crocus sativus. On the other hand, 14 species instead exhibited growth-promoting properties. Of these, the greatest promoting effect were exhibited by the leaves of Cardaria draba, Verbascum speciosum and Urtica dioica eliciting 69 %, 56 %, and 53 %, respectively, which had longer radicles compare to the control. The results hereby presented provide insight into the allelopathic action of the medicinal and wild plants of Iran. Data herein reported serves as benchmark information for further research on the characterization of the allelochemicals in these plants.

Volatile compounds from Achillea tenorii (Grande) growing in the Majella National Park (Italy).

This work presents the first reported phytochemical study on the hydro-distilled essential oil from Achillea tenorii (Grande), collected in the protected area of Majella National Park (Italy). The composition of the essential oil was very different from those reported for the other species of Achillea nobilis group, being constituted mainly by oxygenated monoterpenes, among which ketones, alcohols and acetates compounds were the most representative. The marker compounds of A. nobilis group were not detected while the most abundant phytoconstituents were α-thujone (29.7%), trans-sabinol (18.6%) and trans-sabinyl acetate (15.7%), revealing a composition quite similar to that of Artemisia absinthium.

Reactions of (−)-estafiatin with acidic reagents

In continuation of our studies in the field of monoand bicyclic sesquiterpene γ-lactones [1–3], we examined reactions of guaianolide (–)-estafiatin (I) isolated from noble yarrow (Achillea nobilis L.) with such acidic reagents as boron trifluoride–diethyl ether complex and magnesium bromide. The reaction of I with BF3 · Et2O in THF at room temperature afforded a mixture of ketone II and allylic alcohol III in 56 and 40% yield, respectively. Compounds II and III were isolated previously from plant sources and are known as guaianolides, estafiatone and isozaluzanin C, which exhibit pronounced antitumor activity [4, 5].

Composition of the Essential Oils of Anthemis Hyalina DC., Achillea Nobilis L. and Cichorium intybus L. Three Asteraceae Herbs Growing Wild in Iran

Water-distilled essential oils from the aerial parts of Anthemis hyalina DC. (syn. A. crassipes Boiss.), Achillea nobilis L. and Cichorium intybus L. were analyzed by GC and GC-MS. Twenty-four components of the oil of Anthemis hyalina were characterized, representing 98.1 % of the total components detected. The major constituents were identified as carvacrol (38.4 %) and α-pinene (30.9 %). The oil of Achillea nobilis was characterized by higher amounts of artemisia ketone (46.7 %), among the thirty components comprising 95.4 % of the total oil detected. Hexadecanoic acid (32.9 %), nonadecane (26.1 %) and trans-α-bergamotene (14.0 %) were the main components among the fourteen constituents characterized in the oil of Cichorium intybus representing 100 % of the total components detected.

Antinociceptive and Anti-inflammatory Activities and Acute Toxicity of Achillea nobilis. subsp. neilreichii. Extract in Mice and Rats

The ethanol extract of Achillea nobilis. L. subsp. neilreichii. (Kerner) Formanék (Asteraceae) flower heads was investigated for its antinociceptive and anti-inflammatory activities and for acute toxicity in mice and rats. While the extract exhibited an antinociceptive effect during the late phase of the formalin test (100, 200, and 400 mg/kg, i.p.) and an anti-inflammatory effect in the paw edema test (100 and 200 mg/kg, i.p.), it did not exert any significant antinociceptive effect in the tail-flick test. Furthermore, administration of 400 mg/kg extract increased the latency to hot-plate test at 60 and 90 min. No significant change was detected in sensory motor performance. The acute LC50 value of the extract was 4456 mg/kg (i.p.) in mice. The current results demonstrate that an ethanol extract of A. nobilis. L. subsp. neilreichii. exerts anti-inflammatory activity.

The protective effects of Achillea L. species native in Turkey against H 2O 2-induced oxidative damage in human erythrocytes and leucocytes

The aim of the present study was to investigate the protective effects of infusions prepared from 15 Achillea (Asteraceae) species against H 2O 2-induced oxidative damage in human erythrocytes and leucocytes used in traditional Turkish medicine. CAT, SOD and GPx activities, effects of LPO and GSH levels of the infusions on erythrocytes and leucocytes were assessed. The results indicated that all infusions of Achillea species were effective on antioxidant enzyme systems of erythrocytes and leucocytes when compared with H 2O 2 group. Achillea falcata was the most effective one on CAT, GPx and SOD enzyme systems of erythrocytes. Among plant infusions, Achillea crithmifolia and Achillea nobilis subsp. neilrechii showed the highest activities on CAT, while Achillea millefolium subsp. pannonica on SOD, Achillea teretifolia on GPx and Achillea nobilis subsp. sipylea on LPO enzyme systems of leucocytes. The present results demonstrate that infusions of Achillea species are a potential source of natural antioxidants for treatment and prevention of diseases in which LPO takes place.

Composition and Antibacterial Activity of Achillea crithmifolia and Achillea nobilis Essential Oils

The composition of the essential oils of Achillea crithmifolia and Achillea nobilis was analyzed by GC and GC/MS. The main compounds of the A. crithmifolia essential oil were camphor (27.6%), 1,8-cineole (26.5%) and trans-chrysanthenyl acetate (18.8%), while the most abundant compounds in the A. nobilis oil were α-thujone (25.7%), artemisia ketone (14.8%), borneol (9.9%) and camphor (8.2%). The antibacterial activity of oils was tested for the first time. Both examined oils showed very strong antibacterial activity against all tested microorganisms (Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Staphylococcus aureus).

Analysis of flavonoids in Achillea nobilis L. bv capillarv electrophoresis

The separation and quantification of the flavonoids occurring in Achillea nobilis L. by a CE-method is described. Using 20 mM sodium borate at pH 9.5 with 20 % of methanol as buffer, the flavonoids were sufficiently separated within 11 minutes. Kaempferol-7-O-neohesperidoside was used as internal standard for the quantification. Analysis of six different samples showed the flavon-C-glycosides isoorientin, orientin and vitexin as the characteristic main compounds. The contents of flavon-C-glycosides determined by this CE-method correlated with the results achieved by a spectrophotometric determination.

Flavonoids from Achillea nobilis L.

The detailed investigation of a methanolic extract of aerial parts of Achillea nobilis resulted in the isolation of 10 flavonoids. A new C-glycosylflavone, luteolin-6-C-apiofuranosyl-(1'''-->2'')-glucoside, was isolated besides orientin, isoorientin, vitexin, isoschaftoside, luteolin-7-O-beta-glucuronide, luteolin-4'-O-beta-glucoside and quercetin-3-O-methyl ether and two rare flavonolglycosides, quercetin-3-O-alpha-arabinosyl-(1'''-->6'')-glucoside and quercetin-3-O-methylether-7-O-beta-glucoside. The structures were established either by comparison with authentic substances or by UV, 1H NMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS.

Guaianolide-Endoperoxide and Monoterpene-Hydroperoxides fromAchillea nobilis*

From flower heads of Achillea nobilis two chrysanthemol derivatives (1, 2), tanaparthin-beta-peroxide (3), and 5-hydroxy-3,6,7,4'-tetramethoxyflavone (4) were isolated by repeated column chromatography and HPLC. Structure elucidation has been performed by means of MS, 1H-NMR, 13C-NMR, and 2D-NMR experiments.

Distribution of externally accumulated flavonoid aglycones within the Achillea nobilis group

Forty-one collections of six species forming the Achillea nobilis group were analysed for their external aglycone patterns. Most species are characterized by the predominance of 6-methoxyflavonols, whereas the corresponding flavones are of limited distribution. The study was carried out to check primarily the infraspecific variability of these profiles. In addition, their use as possible taxonomic markers is also discussed.

Flavonoid glycoside accumulation trends of Achillea nobilis L. and related species

More than 50 collections of five species forming the Achillea nobilis group were analysed for their leaf flavonoid complement. Major accumulation trends were found to be C-glycosylflavones and flavonol 3- O-glycosides. The most common pattern consisted of the C-8-glycosylfiavones (vitexin and orientin), the C-6-glycosylflavone (isoörientin) together with minor amounts of di- C-glycosylapigenins and quercetin 3- O-glycosides. Additionally, C-6-glycosylflavones (isovitexin) and their 7-methyl ethers swertisin and swertiajaponin were sporadically accumulated, characterizing particularly two subspecies of A. nobilis. Whereas C-glycosylflavone dominated profiles were typical of most species, two taxa exhibited a flavonol dominated profile ( A. ligustica; A. virescens p.p.). Regarding the infraspecific and interpopulational variations of flavonoid accumulation trends, their systematic and ecological significance is briefly discussed.