Minireview on Achillea millefolium Linn

Yarrow (Achillea millefolium L.) is an important medicinal plant with different pharmaceutical uses. A. millefolium has been used for centuries to treat various diseases including malaria, hepatitis and jaundice. A. millefolium is commonly prescribed to treat liver disorders. It is also used as an anti-inflammatory agent and is a hepatoprotective herb. A. millefolium is considered safe for supplemental use. It has antihepatotoxic effects also. It is prescribed as an astringent agent. It is prescribed in hemorrhoids, headache, bleeding disorders, bruises, cough, influenza, pneumonia, kidney stones, high blood pressure, menstrual disorders, fever, rheumatoid arthritis, gout, osteoarthritis, hemorrhagic disorders, chicken pox, cystitis, diabetes mellitus, indigestion, dyspepsia, eczema, psoriasis and boils.     

Achillea millefolium antagonism to Pratylenchus brachyurus

Pratylenchus brachyurus is a phytonematode species mostly damaging crops. It is mainly controlled by agrochemicals which are harmful to the environment and public health. Such outcomes encourage the development of research on products and/or processes to control this phytonematode and to contribute to the sustainability of agricultural systems. Thus, the aim of the current study was to assess host suitability of Achillea millefolium to P. brachyurus, as well as the nematicidal potential of its essential oil and root exudates. We conducted two experiments with two different plant species—Glycine max (soya bean) and Achillea millefolium (yarrow)—based on a 2 × 3 factorial arrangement to assess host suitability. Plants were assessed 5, 10 and 15 days after inoculation through the fuchsine acid staining technique. Based on the results, A. millefolium was an unfavourable host to this phytonematode. Therefore, it can be recommended for crop rotation and/or succession systems in small areas. We tested the nematicidal activity of the essential oil and exudates of A. millefolium at concentrations of 0, 25, 50, 100, 200, 300, 400 and 500 µg/ml in a BOD incubator at 26°C for 48 hr. The essential oil showed increasing linear regression, that is the higher was the concentration, the higher was the mortality rate. Exudates showed a quadratic behaviour (p ≤ .05), leading to 60.83% nematode mortality. Therefore, the essential oil and root exudates of A. millefolium have the potential to control P. brachyurus. The essential oil showed antagonistic properties likely because of the presence of germacrene D (39.55%), (E,E)‐α‐farnesene (25.70%) and chamazulene (8.91%).     

Achillicin,the first proazulene from Achillea millefolium

Achillicin, the major proazulene (prochamazulene) of Achillea millefolium L. ssp. collina Becker has been isolated and identified as 8-acetoxyartabsin. It is the first proazulene reported for the genus Achillea and has not been found previously in plants.     

Composition of the essential oil from cell suspension cultures of Achillea millefolium ssp. millefolium

The composition of the essential oil isolated from Achillea millefolium L. ssp. millefolium cell suspension cultures was analysed by GC and GC-MS. The yield of the oil obtained by hydrodistillation or a simultaneous distillation -extraction of these cultures, harvested at days 8–10 (end of exponential phase), was 0.001 % (w/w). The analysis of the volatiles showed the presence of thirteen components; monoterpenes amounted to 5%, sesquiterpene hydrocarbons attained 40%, while eugenol, demethoxyencecalin and two unidentified compounds amounted to 45% of the total oil. Several methods were tested in an attempt to increase the essential oil production by the cultures: growth on solid medium, growth in light, use of a different culture medium, elicitation with cellulase or yeast extract, and growth in a two-phase system. Of the different methods tested, the growth in B5⁺ medium with Miglyol 812 led to the highest essential oil yield (0.002%, w/w), and resulted in a more diverse oil composition.     

Ethnobotany and phytochemistry of yarrow,Achillea millefolium,compositae

The data reported in the literature concerning the uses and composition of yarrow,Achillea millefolium aggr., Compositae, are compiled and discussed. Historically, this plant has been extensively used as a herbal remedy for numerous afflictions by many cultures on several continents. It has also been the subject of a considerable number of scientific investigations. It has, however, not been previously reviewed. Analysis of available information demonstrates the value of continued phytochemical investigations of folklore remedies.     

Phenolic compounds from Achillea millefolium L. and their bioactivity

Since antiquity, Achillea millefolium L. (Asteraceae) has been used in traditional medicine of several cultures, from Europe to Asia. Its richness in bioactive compounds contributes to a wide range of medicinal properties. In this study, we assessed A. millefolium methanolic extract and its isolated components for free radical scavenging activity against 2,2-diphenyl-pycrilhydrazyl, total antioxidant capacity (based on the reduction of Cu(++) to Cu(+)), and ability to inhibit lipid peroxidation. The activity against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum was also tested. Chlorogenic acid, its derivatives and some flavonoids isolated by semipreparative HPLC and identified by NMR and spectrometric techniques were the major bioactive constituents of the methanolic extract. The latter exhibited significant antioxidant properties, as well as its flavonol glycosides and chlorogenic acids. With regard to the antiplasmodial activity, apigenin 7-glucoside was the most effective compound, followed by luteolin 7-glucoside, whereas chlorogenic acids were completely inactive. On the whole, our results confirmed A. millefolium as an important source of bioactive metabolites, justifying its pharmaceutical and ethnobotanical use.     

Biotransformation of monoterpenes and sesquiterpenes by cell suspension cultures of Achillea millefolium L. ssp. millefolium

The transformation capacity of Achillea millefolium L. ssp. millefolium (yarrow) cell suspension cultures was investigated using geraniol (50mg/l) and borneol, menthol, thymol and farnesols (25mg/l) as substrates. Apart from converting these substrates into several biotransformation products, the cell suspension cultures were also able to glycosylate both the substrates and the biotransformation products. aa]Key Words bb]Achillea millefolium L. ssp. millefolium bb]Yarrow bb]Compositae bb]Biotransformation bb]Glycosylation bb]Geraniol bb]Borneol bb]Menthol bb]Thymol bb]Farnesols     

Comparative responses of Achillea millefolium ecotypes to competition and soil type

Summary Achillea millefolium populations from adjacent sites with zonal and serpentime soil were used to test predictions about the relation between growth and the competitive ability of plants in productive and unproductive environments. Under greenhouse conditions, individually-grown plants from both sources grew larger in serpentine soil than in zonal soil; serpentine plants accumulated 72% more biomass than zonal plants. In zonal soil, zonal plants were 71% larger than serpentine plants, although these differences were not statistically significant, and plants from both sources accumulated much less biomass and were shorter than plants growing in serpentine soil. In a high density, fertilized replacement series, zonal plants were taller and heavier but exhibited no more competitive ability than serpentine plants. The predictions that rapid height growth and biomass accumulation contribute significantly to competitive ability are not supported by our results. Although ecotypic differentiation has occurred between these A. millefolium populations, apparently in response to different soil types, the expression of these heritable differences can be masked by other environmental effects. There has been no apparent trade-off in these ecotypes between their response to the physical environment and their competitive ability.     

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.     

Germacrane-Type Sesquiterpene Lactones from Achillea millefolium L. and Their Anti-Inflammatory Activity

Six undescribed germacrane-type sesquiterpene lactones, millefoliumons A–F, and two known analogs were isolated from the ethyl acetate fraction of the whole plant of Achillea millefolium L. growing in Xinjiang, China. The structures of these compounds were fully elucidated by their 1D and 2D nuclear magnetic resonance (NMR), and high resolution mass (HR-ESI-MS) spectral data, and comparison with literatures. The absolute configurations of millefoliumons A–F were confirmed by experimental and calculated electronic circular dichroism data (ECD), and ¹³C-NMR calculations and DP4+ probability analysis. All compounds displayed the approximate tendency to inhibit the nitric oxide (NO) release in lipopolysaccharide (LPS)-induced BV2 cells.     

Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group

The investigation of a dichloromethane extract of flower heads of a Hungarian taxon of the Achillea millefolium group led to the isolation of three flavonoid aglycones, one triterpene, one germacranolide and five guaianolides. Their structures were elucidated by UV-VIS, EI- and CI-MS, 1H NMR and 13C NMR spectroscopic methods as well as by 2D-NMR studies and by selective 1D-NOE experiments. Besides apigenin, luteolin and centaureidin, beta-sitosterol, 3beta-hydroxy-11alpha,13-dihydro-costunolide, desacetylmatricarin, leucodin, achillin, 8alpha-angeloxy-leucodin and 8alpha-angeloxy-achillin were isolated. Both latter substances are reported here for the first time. Their NMR data were compared with those of the other guaianolides. The stereochemistry of 3beta-hydroxy-11alpha,13-dihydro-costunolide was discussed and compared with data of the literature.     

Achillea millefolium (yarrow) cell suspension cultures: Establishment and growth conditions

Summary Friable calli were obtained fromAchillea millefolium L. hypocotyls, in Gamborg B5 medium, supplemented with 1.5mg.1^–1 2,4-D / 0.1mg.1^–1 Kin, and used for the production of cell suspension cultures in the same liquid medium. The growth pattern of the cultures was determined in permanent light or dark conditions and with different inoculum densities, basal media, growth regulators and sucrose concentrations. Different sources and nitrogen amounts were assayed to study the effect on yarrow cell growth. The conditions found to be optimal for growth of yarrow cell suspension cultures were: 70g (f.w.).1^–1 of initial inoculum in Gamborg B5 medium, supplemented with 1.5mg. 1^–1 2,4-D / 0.1mg.1^–1 Kin, NO₃ ^–/NH₄ ⁺ (30/lmM), and 2% sucrose, in darkness. In these culture conditions the cell suspensions showed a doubling time of 35–40h.Abbreviations 2,4-D dichlorophenoxyacetic acid - NAA naphtalenacetic acid - BA benzyladenine - Kin Kinetin     

The Polyploid Series of the Achillea millefolium Aggregate in the Iberian Peninsula Investigated Using Microsatellites

The Achillea millefolium aggregate is one of the most diverse polyploid complexes of the Northern hemisphere and has its western Eurasian boundary in the Iberian Peninsula. Four ploidy levels have been detected in A. millefolium, three of which have already been found in Iberia (diploid, hexaploid and octoploid), and a fourth (tetraploid) reported during the preparation of this paper. We collected a sample from 26 Iberian populations comprising all ploidy levels, and we used microsatellite markers analyzed as dominant in view of the high ploidy levels. Our goals were to quantify the genetic diversity of A. millefolium in the Iberian Peninsula, to elucidate its genetic structure, to investigate the differences in ploidy levels, and to analyse the dispersal of the species. The lack of spatial genetic structure recovered is linked to both high levels of gene flow between populations and to the fact that most genetic variability occurs within populations. This in turn suggests the existence of a huge panmictic yarrow population in the Iberian Peninsula. This is consistent with the assumption that recent colonization and rapid expansion occurred throughout this area. Likewise, the low levels of genetic variability recovered suggest that bottlenecks and/or founder events may have been involved in this process, and clonal reproduction may have played an important role in maintaining this genetic impoverishment. Indeed, the ecological and phenologic uniformity present in the A. millefolium agg. in Iberia compared to Eurasia and North America may be responsible for the low number of representatives of this complex of species present in the Iberian Peninsula. The low levels of genetic differentiation between ploidy levels recovered in our work suggest the absence of barriers between them.     

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.     

Achillinin A, a cytotoxic guaianolide from the flower of Yarrow, Achillea millefolium

Achillinin A (2β,3β-epoxy-1α,4β,10α-trihydroxyguai-11(13)-en-12,6α-olide, 1), a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC(50)) values of 5.8, 10 and 0.31 μM, respectively.     

In Vitro Regeneration of Achillea millefolium L from Shoot-tips and Root Segments of Seedlings

This report describes, for the first time, an efficient plant regeneration system for Achillea millefolium L (yarrow), a medicinal plant, via shoot multiplication from shoot-tips and adventitious shoot regeneration from root segments. Higher numbers of shoots were obtained when shoot-tips were cultured on MSMO medium supplemented with 3.0 mg l^?1 BA and 0.5 mg l^?1 IAA, or 5.0 mg l^?1 KIN and 1.0 mg l^?1 IBA, producing 17.3 and 17.0 shoots per explant at 100% frequency, respectively. For adventitous shoot regeneration, only root segments developed shoots when cultured on medium containing a combination of 1 mg l^?1 TDZ, 0.5 mg l^?1 IAA and 0.5 mg l^?1 GA3 (18.9 shoots per explant at 100% frequency), while other types of explants (i.e., cotyledons, leaf lamina and petiole segments) or hormonal combinations tested were found ineffective. Regenerated shoots rooted readily on MSMO medium containing different concentrations of IAA, IBA, NAA or 2,4-D, however, NAA at 0.5 mg l^?1, or IBA at 0.5 or 1.0 mg l^?1 were found to be the most productive. Nearly all of the regenerated plants (98%) survived through the hardening process when the rooted plantlets were kept at 55–65% relative humidity for 2 weeks, which were then planted in pots containing potting soil and kept at 25–35% humidity.     

Achillinin A,a Cytotoxic Guaianolide from the Flower of Yarrow,Achillea millefolium

Achillinin A (2β,3β-epoxy-1α,4β,10α-trihydroxyguai-11(13)-en-12,6α-olide, 1), a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC₅₀) values of 5.8, 10 and 0.31 μM, respectively.     

Ultrastructural Aspects of the Glandular Cells from the Secretory Trichomes and from the Cell Suspension Cultures of Achillea millefolium L. ssp. millefolium

The ultrastructure of the glandular cells of the floret secretorytrichomes from Achillea millefolium L. ssp. millefolium (yarrow)was examined before and after anthesis and compared with theultrastructure of the cells from the cell suspension culturesobtained from the same plant. The profuse tubular structuresobserved in the plastids of the glandular cells of the trichomesduring the pre-secretory stage were much reduced in the secretorystage and showed an osmiophilic content. Some endoplasmic reticulumprofiles could be seen adjacent to the plastids. Later in thesecretory stage, the secretion appeared in the periplasmic spacebetween the cells of the upper tiers and in the sub-cuticularspace. Finally the secretion was released by rupture of thecuticle. At the lag phase, the cells from the cell suspensioncultures of yarrow were characterized by the presence or plastidswith tubular structures, similar to those observed in the plastidsof the trichomes in the pre-secretory stage. By the end of thelag phase accumulations of starch were observed inside the plastids.At the beginning of the exponential phase, the tubular structuresof the plastids started to show an osmiophilic content and theaccumulations of starch were still present. At the end of thisphase starch disappeared from the plastids and only osmiophilictubular structures were observed. Rough endoplasmic reticulumas well as smooth endoplasmic reticulum profiles were frequentlyin close association with plastids and mitochondria. At thestationary phase a very large vacuole filled the cells, andin the remaining cytoplasm some endoplasmic reticulum profilesand osmiophilic droplets were observed.Copyright 1994, 1999Academic Press Achillea millefolium L. spp. millefolium, yarrow, ultrastructure, trichomes, glandular cells, plant cell suspension cultures     

A straightforward procedure to biosynthesise melatonin using freshly chopped Achillea millefolium L. as reagent

d, l-Tryptophan as the precursor of melatonin and Achillea millefolium L. as the plant cell tissue were used in order to force the plant enzymatic system to enhance the production of melatonin.The biotransformation protocol was performed by adding the precursor to the freshly chopped plant material suspended in water and stirred at room temperature in total darkness. The melatonin content was evaluated by LC-DAD-ESI-MS. The precursor-treated sample gave at least six times (345 ng/g_{fresh plant}) the melatonin amount usually produced in young plants of A. millefolium L. (50 ng/g_fresh plant).The present study shows that, in principle, adding a specific precursor to a suitable freshly chopped plant material can significantly enhance a secondary metabolite production.     

Development and characterization of microsatellite markers for genomic analysis of yarrow (Achillea millefolium L.)

Yarrow (Achillea millefoilum L.) is an important medicinal plant with different medicinal and ornamental uses. In this study, SSR markers were developed for the first time from the genome A. millefolium using the slightly modified Hamilton protocol. Three yarrow genomic libraries were constructed, enriched for microsatellite motifs AG, AC and ATG. A total of 30 primer pairs were developed of which 16 were polymorphic in 26 A. millefolium accessions. One accession from A. tenuifolia species was also included to assess the transferability of new developed SSR primers in other species. The average allele number of SSR markers was 8.5 per locus and ranged from 2 to 14. The observed heterozygosity (H _O) varied from 0 to 0.96 with an average of 0.52 and the expected heterozygosity (H _E) ranged from 0.07 to 0.49 with an average of 0.39. Among primers, Am142 showed the highest polymorphic information content (PIC) and the lowest value was obtained from Am59 primer with an average of 0.33. Three loci (AmK59, AmK344 and AmK329) deviated significantly from Hardy-Wrinberg Equlibrium (HWE) and one locus (Am344) might have null alleles. Cluster and PCoA analyses classified A. millefolium accessions according to their geographical distribution and A. tenuifolia species completely separated from A. millefoliulm genotypes.