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In vitro antimicrobial activity of extracts of four Achillea species: the composition of Achillea clavennae L. (Asteraceae) extract.

The extracts of aerial parts of Achillea clavennae, Achillea holosericea, Achillea lingulata and Achillea millefolium (hexane:ether:methanol=1:1:1) have been tested for antimicrobial activity in a disk diffusion assay against five bacteria (Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Salmonella enteritidis) and two fungi (Aspergillus niger and Candida albicans). Extracts of all four species possessed a broad spectrum of antimicrobial activity against all tested strains. The composition of the extract of Achillea clavennae, which showed the strongest activity, was investigated and the structures of isolated compounds were elucidated by spectral means (1D and 2D NMR, UV, IR and MS). The extract yielded alkanes, fatty acids, monoterpenes, guaiane sesquiterpenes (rupicolin A and B, 1-deoxy-1alpha-peroxy-rupicolin A and B), and flavonoids (apigenin and centaureidin). This study confirms the ethnopharmacological use of plants from this genus and places Achillea clavennae L. on the same level as the recognized Achillea millefolium.

Achillea↗

Highly hydroxylated guaianolides of Achillea asiatica and Middle European Achillea species.

From flower heads of Achillea asiatica (L.) Serg., three new guaianolides were isolated by repeated column chromatography and HPLC. The constitution and the stereochemistry of these new, labile compounds were determined by MS, one ((1)H, (13)C, selective (1)H-TOCSY and (1)H-NOESY) and two-dimensional NMR experiments ((1)H, (1)H-COSY, (1)H, (13)C-HSQC, (1)H, (13)C-HMBC). The substances were identified as 8 alpha-angeloxy-2 alpha, 4 alpha,10 beta-trihydroxy-6 beta H,7 alpha H, 11 beta H-1(5)-guaien-12,6 alpha-olide (1), 8 alpha-angeloxy-1 beta,2 beta:4 beta,5 beta-diepoxy-10 beta-hydroxy-6 beta H, 7 alpha H, 11 beta H-12,6 alpha-guaianolide (2) and 8 alpha-angeloxy-4 alpha,10 beta-dihydroxy-2-oxo-6 beta H,7 alpha H, 11 beta H-1(5)-guaien-12,6 alpha-olide (3). They were also detected in Middle European species (Achillea collina, Achillea ceretanica (2x and 4x), Achillea roseoalba, Achillea asplenifolia) by HPLC, TLC and off line MS and have not been described before. The possibility that these compounds might be products of an oxidation process is discussed.

Asteraceae↗

Compositions and the in vitro antimicrobial activities of the essential oils of Achillea setacea and Achillea teretifolia (Compositae).

GC-MS analysis of the isolated essential oils from air-dried aerial parts of Achillea setacea and Achillea teretifolia, an endemic taxon, resulted in the identification of 51 constituents (79.8% of the total oil) and 42 constituents (87.1% of the total oil), respectively. Eucalyptol (1,8-cineole) was the major constituent of both oils studied (18.5 and 19.9%, respectively). The antimicrobial activities of the essential oils were individually evaluated against 14 microorganisms. Both oils exhibited inhibitory effects on Clostridium perfringens, Acinetobacter lwoffii and Candida albicans with a range of minimum inhibitory concentration values extended from 0.28 to 2.25 mg/ml. Camphor and their derivatives, borneol, terpinen-4-ol and eucalyptol (1,8-cineol) can be considered as the main antimicrobial constituents of the oils studied.

Achillea↗

Biological activity and composition of the essential oils of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica.

The essential oils obtained by water distillation from aerial parts of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica were analyzed by gas chromatography and gas chromatography/mass spectrometry. 1,8-Cineole (32.5 and 26.1%, respectively) was the main component in both oils. The oil of A. aleppica subsp. aleppica was also found to be rich in bisabolol and its derivates. When tested for their antimicrobial, antiinflammatory, and antinociceptive activities, the oil of A. aleppica subsp. aleppica showed significant antiinflammatory, antinociceptive, and moderate antimicrobial activities.

Achillea↗

Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt.

Essential oils obtained by steam distillation from the aerial parts of Achillea fragrantissima (Forssk.) Sch. Bip. and the flower, leaf and stem of A. santolina L. as well as their lipophilic constituents obtained by solvent extraction were analysed using GLC and GLC-mass spectrometry. Nineteen constituents in the essential oil of A. fragrantissima were identified, in addition to 41 compounds from its n-hexane-ether extract. The hydrodistilled oil and the solvent extract contain santolina alcohol, artemisia alcohol, artemisia ketone, cis-thujone and trans-thujone as major constituents. In A. santolina altogether 54 volatile components were detected. The major components were 1,8-cineole, fragranol, fragranyl acetate and terpin-4-ol. Furthermore, the essential oils and the n-hexane-ether extracts of the two plants were screened for their antimicrobial activity.

Achillea↗

The protective effects of Achillea L. species native in Turkey against H(2)O(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(2)O(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(2)O(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.

Achillea↗

Hybrid origin and differentiation of two tetraploid Achillea species in East Asia: molecular, morphological and ecogeographical evidence.

Achillea (Asteraceae-Anthemideae) offers classical models for speciation by hybridization and polyploidy. Here, we test the suspected allotetraploid origin of two species, Achillea alpina and Achillea wilsoniana between phylogenetically distinct lineages in East Asia. A total of 421 AFLP bands from 169 individuals and 19 populations of five 2x- and two 4x-species were obtained. The data set was analysed with a newly developed model that accounts for polyploidy and assumes lack of recombination between the parental chromosome sets (i.e. disomic inheritance). A. alpina and A. wilsoniana then appear to be allotetraploids between Achillea acuminata-2x (sect. Ptarmica) and Achillea asiatica-2x (sect. Achillea). The two 4x-species share 44% and 48% of their AFLP bands with A. acuminata-2x, and 39% and 38% with A. asiatica-2x, respectively. Eight plastid haplotypes (A-H) were detected by polymerase chain reaction-restriction fragment length polymorphism (PCR-RFLP) analyses. A. alpina-4x and A. wilsoniana-4x share haplotype F only with A. asiatica-2x. This is consistent with the hybrid origin(s) involving the latter as the maternal ancestor. This result corroborates our previous DNA sequence data, where A. alpina-4x and A. wilsoniana-4x are also placed close to A. asiatica-2x. Morphology, ecology, and amplified fragment length polymorphism (AFLP) profiles of the two 2x-species are distinct, whereas the two 4x-species, grouped as A. alpina aggregate, form a nearly continuous link between them. Considering all evidence, this 4x-aggregate is regarded as the product of a hybridization between genetically distant 2x-ancestors limited to China and adjacent areas: one A. acuminata-like, and the other A. asiatica-like. The allopolyploid A. alpina agg. exhibits considerable morphological variation and ecological flexibility, and has expanded throughout eastern Asia and to northern North America, far beyond the ranges of their presumed 2x-ancestors.

Achillea↗

Final report on the safety assessment of Yarrow (Achillea millefolium) Extract.

Yarrow (Achillea Millefolium) Extract is an extract of the yarrow plant, Achillea millefolium, supplied in polypropylene glycol, which is reported to function as a "biological additive" in cosmetic products. Sesquiterpene lactones, polyacetylenes, simple coumarins, and flavonoids have been identified among the many components of A. millefolium. Yarrow Extract was reportedly used in 65 cosmetic formulations. Historically, Yarrow (Achillea Millefolium) Extract was reported to be used at concentrations of < or =25%, but recent data indicate that this ingredient is supplied with actual Yarrow (Achillea Millefolium) Extract content of 2% to 25% and used at concentrations of 0.5% to 10%. Only limited toxicity data were available. Guinea pigs were sensitized to crude extracts of the whole plant and the flowers of A. millefolium. A. millefolium tea was weakly genotoxic in a somatic mutation and recombination test using Drosophila melanogaster. In clinical testing, product formulations containing 0.1% to 0.5% of ingredient that actually contained 2% of Yarrow Extract were generally not irritating. In provocative testing, patients reacted to a Compositae mix that contained yarrow, as well as to yarrow itself. Also in clinical testing, a formulation containing 0.1% Yarrow (Achillea Millefolium) Extract (2% Yarrow in propylene glycol and water) was not a sensitizer in a maximization test and alcoholic extracts of dried leaves and stalks of A. millefolium did not produce a phototoxic response. These data were not considered sufficient to support the safety of this ingredient in cosmetics. The types of data (all testing is to be performed on cosmetic-grade ingredients) still required include (1) ultraviolet (UV) absorption data, if absorption occurs in the UVA or UVB range, photosensitization data are needed; (2) gross pathology and histopathology in skin and other major organ systems associated with repeated exposures; (3) reproductive and developmental toxicity data; (4) two genotoxicity studies, one using a mammalian system, if positive, a 2-year dermal carcinogenicity assay performed using National Toxicology Program (NTP) methods may be needed; and (5) clinical sensitization testing at maximum concentration of use. In the absence of these data, it was concluded that the available data are insufficient to support the safety of Yarrow (Achillea Millefolium) Extract for use in cosmetic products.

Absorption↗

[Enantiomeric monoterpenes in ether oil from Achillea millefolium s. I.--a taxonomically useful marker?].

The Achillea millefolium complex is a group of taxonomically hardly separable species. Yarrow has the tendency to hybridize and to vary in phenotype. An obvious characterization of the species or hybrids is not just important for the taxonomical distinction but also for a reliable assessment of herbal drug quality. Most of the Achillea plants are still gathered from natural populations. According to the variation in phenotype, mixtures with Achillea species, which contain allergy setting compounds, often cannot be determined. Morphometric investigations exclusively do not replace a further chemical characterization. Therefore we tried to assess the composition of the chiral monoterpenes alpha-pinene, beta-pinene and sabinene. They were selected because of their frequency in the essential oil of Achillea species. By method of M.C.S.S. (Moving Capillary Stream Switching) the differentiation of stereoisomeres succeeded directly from the essential oil, which was distilled or extracted by headspace trapping at room temperature. The enantiomeric distribution neither depends on the method of extraction, nor on the habitat or the developmental stage of Yarrow. Since the compositions of enantiomeres from several Achillea species and their hybrides are of different pattern, it seemed to represent an additional marker. Though investigations of all species within the Achillea millefolium group and possibly of further chiral compounds are necessary to ensure these results.

Bicyclic Monoterpenes↗

Exudate flavonoid aglycones in the alpine species of Achillea sect. Ptarmica: Chemosystematics of A. moschata and related species (Compositae-Anthemideae).

In completion of our studies on Achillea exudate flavonoids, 11 alpine species of Achillea sect. Ptarmica were analyzed for their aglycone profiles. The study focuses on species commonly associated with A. moschata. The major flavonoid constituents found in exudates of most taxa were 6-hydroxyflavonol 3,6,4'-trimethyl ethers, except in A. ageratifolia and its subspecies, which are characterized by the accumulation of the 3,6,7-trimethoxy and 6-hydroxyflavones. Infraspecific variation was particularly high in A. abrotanoides and A. moschata. Results are discussed in relation to published data for related species and within the context of evolutionary aspects in the genus Achillea. The 3,6,4'-trimethoxy substitution is regarded as a basic chemical trend within the genus Achillea. Geographical and ecological aspects are briefly addressed, and a summary on known exudate aglycone composition of species from all sections of Achillea is included.

Journal Article↗

Anticonflict actions of aqueous extracts of flowers of Achillea millefolium L. vary according to the estrous cycle phases in Wistar rats.

Anticonflict-like effects of aqueous extract of flowers of Achillea millefolium L., a plant with purported anxiolytic actions, were studied in female Wistar rats during late proestrus or diestrus. During late proestrus (p < 0.05), control rats displayed reduced conflict behavior compared with diestrus. Diazepam (2.0 mg/kg; i.p.) reduced conflict behavior both during late proestrus (p < 0.05) or diestrus (p < 0.05). Doses of 8.0 mg/kg (p < 0.05), 10.0 mg/kg (p < 0.05) or 12.0 mg/kg (p < 0.05) of Achillea millefolium reduced conflict behavior during late proestrus. Conversely, during diestrus, only the dose of 12.0 mg/kg (p < 0.05) of Achillea millefolium L. reduced conflict behavior. In conclusion, the anticonflict-like actions of Achillea millefolium L. may vary according to the estrous cycle phase.

Achillea↗

Analysis of aroma and phenolic components of selected Achillea species.

Dried flowers and leaves of four different Achillea species grown wild in several provinces of Iran, including one species collected from three different locations of Isfahan province were analyzed for the headspace volatile components, total phenolics (TP) and tartaric esters (TE). Capillary gas chromatography/mass spectrometry (GC/MS) combined with a purge and trap method was used for quantification of aroma components. Over 70 compounds were determined in the samples. Flower samples from all species contained 2-methyl butanal, alpha-pinene, alpha-thujene, camphene, hexanal, beta-pinene and 1,8-cineole; however, the major constituents of the aerial parts were determined as alpha-pinene, camphene, DL-limonene and 1,8-cineole. The largest number of aroma components were found in Achillea tenuifolia Lam. and Achillea millefolium L. In all species, except A. millefolium, the leaves contained more TP and TE than flowers. However, A. wilhelmsii from Semirom in Isfahan province showed the highest values for TP and TE.

Achillea↗

AFLP analyses demonstrate genetic divergence, hybridization, and multiple polyploidization in the evolution of Achillea (Asteraceae-Anthemideae).

Achillea, a temperate genus of herbaceous allogamous perennials, is a model for evolutionary radiation through hybridization and polyploidization. AFLP analyses were performed on 300 individuals of 66 populations and 27 taxa/cytotypes, mainly from the polyploid A. millefolium aggregate and its suspected hybrid links with other clades of the genus. The mosaic genetic structure of hybrids and polyploids is revealed by specific AFLP bands shared with their assumed parents. In E Asia, A. alpina-4x and A. wilsoniana-4x are allotetraploids between A. acuminata-2x (sect. Ptarmica) and A. asiatica-2x (sect. Achillea-A. millefolium agg.). A. virescens-4x is a hybrid species linking A. nobilis agg. and A. millefolium agg. in S Europe. The hybrid swarm A. clypeolata-2x yen A. collina-4x recently formed in Bulgaria shows no AFLP bands additive to its parents; by contrast, other more ancient allopolyploids exhibit genetic innovations. Relationships within A. millefolium agg. are complex. Five 2x-taxa, mostly well separated and regressive, are limited to Eurasia; seven 4x- and 6x-taxa are intimately linked by hybridization, are expansive, and through A. asiatica-2x/4x have formed the N American polyploids. All these results from AFLPs correspond well to other evidence, and indicate a long history of reticulate evolution in Achillea.

Achillea↗