Multivariate analysis of the phytochemical composition and antioxidant properties in twenty-five accessions across three Achillea species.

This study explored the chemical composition, antioxidant activity, and total phenol content of aerial parts from 25 accessions of three Achillea species (Achillea wilhelmsii C. Koch, Achillea vermicularis Trin., and Achillea tenuifolia Lam.). The plants were collected from various natural habitats across Iran, encompassing regions such as Central, Western, Southern, Northern, Western, and Northwestern parts of the country. Subsequently, they were grown together under field conditions. The study revealed significant variation in essential oil yields among accessions of A. wilhelmsii, ranging from 0.01 to 0.107%, A. vermicularis with a range of 0.075 to 1.5%, and A. tenuifolia showing a variation of 0.1 to 2%. The study utilized Gas Chromatography-Mass Spectrometry (GC-MS) analysis, revealing 75, 49, and 75 compounds in the essential oils of A. wilhelmsii, A. tenuifolia, and A. vermicularis, respectively. Major components included camphor, 1,8-cineole, anethole, α-pinene, and phytol in A. wilhelmsii, 1,8-cineole, camphor, levo-carvone, and δ-terpinene in A. vermicularis, and ß-cubebene, elixene, ß-sesquiphellandrene, 1,8-cineole, camphor, and δ-terpinene in A. tenuifolia. The essential oil compositions of A. wilhelmsii and A. vermicularis were predominantly characterized by oxygenated monoterpenes, whereas that of A. tenuifolia was characterized by sesquiterpenes. Cluster analysis grouped accessions into three clusters, with A. tenuifolia forming a distinct group. Principal Component Analysis (PCA) triplot (62.21% of total variance) confirmed these results and provided insights into compound contributions. Furthermore, total phenolic content and antioxidant activity of the accessions of three species were assessed over 2 years. A. tenuifolia exhibited the highest levels in both categories, with statistically significant linear regression between antioxidant activity and total phenol content for A. tenuifolia and A. wilhelmsii. These findings emphasize significant phytochemical diversity within Achillea species, positioning them as promising natural sources of antioxidants. Further exploration and selection of specific accessions within each species are crucial for unlocking their medicinal potential and supporting cultivation and conservation efforts.

Influence of Extraction Solvent on the Phenolic Profile and Bioactivity of Two Achillea Species.

The phenolic composition, as well as the antioxidant and antimicrobial activities of two poorly investigated Achillea species, Achillea lingulata Waldst. and the endemic Achillea abrotanoides Vis., were studied. To obtain a more detailed phytochemical profile, four solvents with different polarities were used for the preparation of the plant extracts whose phenolic composition was analyzed using UHPLC-MS/MS (ultra-high performance liquid chromatography-tandem mass spectrometry). The results indicate that both of the investigated Achillea species are very rich in both phenolic acids and flavonoids, but that their profiles differ significantly. Chloroform extracts from both species had the highest yields and were the most chemically versatile. The majority of the examined extracts showed antimicrobial activity, while ethanolic extracts from both species were potent against all tested microorganisms. Furthermore, the antioxidant activity of the extracts was evaluated. It was found that the ethanolic extracts possessed the strongest antioxidant activities, although these extracts did not contain the highest amounts of detected phenolic compounds. In addition, several representatives of phenolic compounds were also assayed for these biological activities. Results suggest that ethanol is a sufficient solvent for the isolation of biologically active compounds from both Achillea species. Moreover, it was shown that the flavonoids naringenin and morin are mainly responsible for these antimicrobial activities, while caffeic, salicylic, chlorogenic, p-coumaric, p-hydroxybenzoic, and rosmarinic acid are responsible for the antioxidant activities of the Achillea extracts.

Achillea millefolium L. and Achillea biebersteinii Afan. Hydroglycolic Extracts-Bioactive Ingredients for Cosmetic Use.

Studies on hydroglycolic (HG) extracts of Achillea biebersteinii (AB)-a less investigated representative of the genus-were performed to determine their potential for cosmetic applications compared to the well-known Achillea millefolium (AM). Three types of water:polyethylene glycol extracts (1:1, 4:1, 6:1 v/v) were obtained from both species and analyzed for their composition by high performance liquid chromatography coupled with mass spectrometry (HPLC-ESI-Q-TOF-MS) and assayed for their biological activities. The study led to the identification of 11 metabolites from different natural product classes with the highest share corresponding to 5-caffeoylquinic acid, axillarin, coumaroylquinic acid isomers and 3-caffeoylquinic acid. The highest antiradical capacity in DPPH and ABTS scavenging assays was shown for HG 4:1 of AB and AM extracts. HG 1:1 extracts from both species inhibited monophenolase and diphenolase activity of tyrosinase, whereas AB HG 4:1 extract showed significant monophenolase inhibition. The highest sun protection factor (SPF) was determined for AM HG 4:1 extract, equal to 14.04 ± 0.17. The AB extracts were cytotoxic for both human keratinocytes HaCaT and A375 melanoma, however HG 1:1 and 4:1 extracts were more cytotoxic for cancer than for noncancerous cells. In conclusion, AB HG 1:1 and 4:1 extracts display significant potential as active cosmetic ingredients.

Achillea spp.: A comprehensive review on its ethnobotany, phytochemistry, phytopharmacology and industrial applications.

The genus Achillea genus houses more than 100 species, a number of them are popularly used in traditional medicine for spasmodic gastrointestinal, gynecological and hepatobiliary disorders, hemorrhages, pneumonia, rheumatic pain, inflammation, wounds healing etc. Members of the genus contain a wide variety of volatile and non-volatile secondary metabolites, including terpenes, polyphenols, flavonoids and others. Multiple studies have assessed the biological effects and other aspects of Achillea spp. In a number of preclinical studies, Achillea plants and their essential oils have demonstrated promising antibacterial properties against a number of human and plant pathogens. Besides, the plants have displayed strong antioxidative and potent anti-proliferative and anticancer properties in various cellular and animal models. Achillea plants have widely been used as food preservative in food industry. Clinical studies have indicated its potential against multiple sclerosis (MS), irritable bowel syndrome (IBS), ulcerative colitis, episiotomy wound, primary dysmenorrhea, oral mucositis etc. The present work focuses to provide a brief overview on folk knowledge, phytochemistry, biological activity and applications of Achillea plants. There is a close relationship between the traditional ethnobotanical usage and pharmacological and clinical data from different Achillea spp. The application of Achillea plants and their extracts seems to be a promising alternative for antimicrobial and antioxidant purposes in food, pharmaceutical and cosmetic industries.

Shedding light on the biological and chemical fingerprints of three Achillea species (A. biebersteinii, A. millefolium and A. teretifolia).

Representatives of the Achillea genus are widely used as foods or nutraceuticals. Considering the increasing demand for herbal dietary supplements with health promoting effects, the objective of this research was to evaluate the biological and chemical profiles of different extracts (ethyl acetate, methanol and water) obtained from three Achillea species (A. biebersteinii, A. millefolium and A. teretifolia). The antioxidant (free radical scavenging (DPPH and ABTS), reducing power (CUPRAC and FRAP), metal chelating and phosphomolybdenum), enzyme inhibitory (anti-cholinesterase, anti-tyrosinase, anti-amylase and anti-glucosidase) and antimicrobial (antibacterial and antifungal) effects were assessed to investigate their biological profiles. Moreover, the total phenolic and flavonoid contents were determined and LC-MS analysis was performed for the chemical profile of the investigated extracts. The LC-MS analysis revealed the presence of several caffeoylquinic acids in these extracts. Generally, the methanol and water extracts exhibited stronger antioxidant abilities, which correlated with the higher levels of phenolic compounds when compared to the ethyl acetate extracts. In addition, the best antimicrobial activities were obtained for the ethyl acetate and methanolic extracts. However, the ethyl acetate extract had remarkable enzyme inhibitory potential. On the basis of our results, Achillea species may be promoted as promising sources of natural agents and used for the development of nutraceuticals or functional food ingredients.

Nuclear and plastid haplotypes suggest rapid diploid and polyploid speciation in the N Hemisphere Achillea millefolium complex (Asteraceae).

BACKGROUND: Species complexes or aggregates consist of a set of closely related species often of different ploidy levels, whose relationships are difficult to reconstruct. The N Hemisphere Achillea millefolium aggregate exhibits complex morphological and genetic variation and a broad ecological amplitude. To understand its evolutionary history, we study sequence variation at two nuclear genes and three plastid loci across the natural distribution of this species complex and compare the patterns of such variations to the species tree inferred earlier from AFLP data. RESULTS: Among the diploid species of A. millefolium agg., gene trees of the two nuclear loci, ncpGS and SBP, and the combined plastid fragments are incongruent with each other and with the AFLP tree likely due to incomplete lineage sorting or secondary introgression. In spite of the large distributional range, no isolation by distance is found. Furthermore, there is evidence for intragenic recombination in the ncpGS gene. An analysis using a probabilistic model for population demographic history indicates large ancestral effective population sizes and short intervals between speciation events. Such a scenario explains the incongruence of the gene trees and species tree we observe. The relationships are particularly complex in the polyploid members of A. millefolium agg. CONCLUSIONS: The present study indicates that the diploid members of A. millefolium agg. share a large part of their molecular genetic variation. The findings of little lineage sorting and lack of isolation by distance is likely due to short intervals between speciation events and close proximity of ancestral populations. While previous AFLP data provide species trees congruent with earlier morphological classification and phylogeographic considerations, the present sequence data are not suited to recover the relationships of diploid species in A. millefolium agg. For the polyploid taxa many hybrid links and introgression from the diploids are suggested.

Biological activities of yarrow species (Achillea spp.).

The genus Achillea consists of about 140 perennial herbs native to the Northern hemisphere. Traditional indications of their use include digestive problems, liver and gall-bladder conditions, menstrual irregularities, cramps, fever, wound healing. The Commission E approves its internal use for loss of appetite and dyspeptic ailments (gastric catarrh, spastic discomfort), externally it is used in form of sitz bath or as a compress against skin inflammation, slow healing wounds, bacterial or fungal infections. In the last decades, pharmacological studies became intensive, although human clinical investigations are still rare. Recent findings have confirmed several traditional uses. The largest number of data accumulated for antioxidant and anti-inflammatory effects. There are positive results on the analgesic, anti-ulcer, choleretic, hepatoprotective and wound healing activities. First results on other interesting therapeutical areas - antihypertensive, antidiabetic, antitumor, antispermatogenic activities -need confirmation. Yarrow can be used also as an insect repellent. Contact dermatitis as adverse effect may be connected to sesquiterpenes. The diversity and complexity of the effective compounds of yarrow species explains the broad spectrum of their activity. According to the literature the pharmacological effects are mainly due to the essential oil, proazulenes and other sesquiterpene lactones, dicaffeoylquinic acids and flavonoids. Synergistic actions of these and other compounds are also supposed. Achillea species have different chemical and therapeutical values. Despite of numerous data, correct evaluation of the results is difficult because of missing generally accepted taxonomical nomenclature. The used chemical-analytical methods and bio-assays are utmost diverse, making the comparison complicated. Further research on the activity is needed using exactly defined plant material, standardized methods and chemical analysis.

Chemical composition, antioxidant and antibacterial properties of Achillea collina Becker ex Heimerl s.l. and A. pannonica Scheele essential oils.

The in vitro antioxidant and antimicrobial activities of two Achillea millefolium (Adanson) Koch s.l species essential oils (A. collina Becker ex Heimerl s.l. and A. pannonica Scheele, Asteraceae) originating from the Golija and Radan mountains (Serbia) were investigated. The chemical profiles of the essential oils were evaluated by GC-MS. Antioxidant activity was assessed as free radical scavenging capacity (RSC) towards 2,2-diphenyl-1-picrylhydrazil (DPPH) radicals, together with effects on lipid peroxidation (LP). Antibacterial activity was examined on 21 bacterial strains. Based on the chemical composition of the essential oil, A. collina s.l. from Mount Golija was classified as a chamazulene chemotype (tetraploid). The high percentage of oxygenated monoterpenes and absence of azulene in the essential oil obtained from A. pannonica from Radan pointing that this population is octaploid. Essential oil of A. pannonica expressed stronger antimicrobial activity on almost all tested bacteria. Furthermore, this essential oil expressed higher scavenging effects on DPPH radical (IC(50) = 0.52 comparing to 0.62 mug/mL). Only in the LP evaluation, essential oil of A. collina s.l. from Golija exhibited stronger antioxidant activity (IC(50) = 0.75 comparing to 2.12 mug/mL).

Distribution of phenolic compounds in Middleeuropean taxa of the Achillea millefolium L. aggregate.

Achillea millefolium L. s.l. is a cytogenetically, morphologically, and chemically polymorphic aggregate. Besides the sesquiterpenes that possess chemotaxonomic relevance and mediate the antiphlogistic activity, the plant contains phenolic compounds such as dicaffeoylquinic acids and flavonoids causing choleretic and spasmolytic effects. To evaluate their contribution to the chemotaxonomy of European taxa of the A. millefolium group, we developed a SPE-HPLC/UV method that allows quantification of the phenolic constituents in the different taxa. The investigated species displayed differences in the quantitative and qualitative composition of phenolic acids and flavonoids. Hence, they seem to be of chemotaxonomic significance, especially for the distinction of the diploid taxa. Combining the obtained results with the data of the sesquiterpene analyses gives a comprehensive insight into the distribution of those pharmacologically relevant plant constituents in the A. millefolium group.

Chemotypes in Achillea collina based on sesquiterpene lactone profile.

The lactone profile of six origins of Achillea collina growing in Bulgaria was studied and significant variability was observed. The reasons for the differences in the lactone composition are discussed. Twenty-five components in total were isolated and identified, while the presence of ten lactones was proved by intensive TLC analysis in comparison with reference compounds. The structures of the components 17, 20, 25-30 were established by spectroscopic methods. The structure of 7, a cyclization product of 6, was also discussed. The anti-inflammatory activity of some extracts, fractions and individual compounds was tested in vitro by determining the inhibitory effects on induced human neutrophils.

Infrared spectroscopy as a tool for chemotaxonomic investigations within the Achillea millefolium group.

An FT-IR-based method for the rapid characterization and identification of Achillea species was developed. With the IR spectra of the CH2Cl2 extracts of A. aspleniifolia, A. collina, A. millefolium, A. millefolium ssp. sudetica, A. pannonica, A. pratensis, A. roseoalba, A. setacea, and A. styriaca, a spectrum library was created. This database allowed the identification of the respective taxa by comparison of IR spectra. Moreover, information concerning dominant structural elements of sesquiterpene constituents was obtained, providing hints about the composition of a plant sample of unknown origin.

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.

[Studies on the pollen morphology of ten species of Achillea].

OBJECTIVE: To study the pollen morphology of ten species of Achillea. METHOD: The pollen morphology of ten species of Achillea was examined with LM and SEM. RESULT: The pollen grains were usually 3-colporate, subspheroidal. The exine ornamentation consisted of verrucate, spinulate and foveolate. But some differences in size, colpae and exine ornamentation were found. CONCLUSION: The slight differences of the pollen morphology are useful to some extent for the classification of the ten species of Achillea.