Secondary metabolic profiling, antioxidant potential, enzyme inhibitory activities and in silico and ADME studies: a multifunctional approach to reveal medicinal and industrial potential of Tanacetum falconeri.

Tanacetum falconeri is a significant flowering plant that possesses cytotoxic, insecticidal, antibacterial, and phytotoxic properties. Its chemodiversity and bioactivities, however, have not been thoroughly investigated. In this work, several extracts from various parts of T. falconeri were assessed for their chemical profile, antioxidant activity, and potential for enzyme inhibition. The total phenolic contents of T. falconeri varied from 40.28 ± 0.47 mg GAE/g to 11.92 ± 0.22 mg GAE/g in various extracts, while flavonoid contents were found highest in TFFM (36.79 ± 0.36 mg QE/g extract) and lowest (11.08 ± 0.22 mg QE/g extract) in TFSC (chloroform extract of stem) in similar pattern as found in total phenolic contents. Highest DPPH inhibition was observed for TFFC (49.58 ± 0.11 mg TE/g extract) and TFSM (46.33 ± 0.10 mg TE/g extract), whereas, TFSM was also potentially active against (98.95 ± 0.57 mg TE/g) ABTS radical. In addition, TFSM was also most active in metal reducing assays: CUPRAC (151.76 ± 1.59 mg TE/g extract) and FRAP (101.30 ± 0.32 mg TE/g extract). In phosphomolybdenum assay, the highest activity was found for TFFE (1.71 ± 0.03 mg TE/g extract), TFSM (1.64 ± 0.035 mg TE/g extract), TFSH (1.60 ± 0.033 mg TE/g extract) and TFFH (1.58 ± 0.08 mg TE/g extract), while highest metal chelating activity was recorded for TFSH (25.93 ± 0.79 mg EDTAE/g extract), TFSE (22.90 ± 1.12 mg EDTAE/g extract) and TFSC (19.31 ± 0.50 mg EDTAE/g extract). In biological screening, all extracts had stronger inhibitory capacity against AChE while in case of BChE the chloroform extract of flower (TFFC) and stem (TFSC) showed the highest activities with inhibitory values of 2.57 ± 0.24 and 2.10 ± 0.18 respectively. Similarly, TFFC and TFSC had stronger inhibitory capacity (1.09 ± 0.015 and 1.08 ± 0.002 mmol ACAE/g extract) against α-Amylase and (0.50 ± 0.02 and 0.55 ± 0.02 mmol ACAE/g extract) α-Glucosidase. UHPLC-MS study of methanolic extract revealed the presence of 133 components including sterols, triterpenes, flavonoids, alkaloids, and coumarins. The total phenolic contents were substantially linked with all antioxidant assays in multivariate analysis. These findings were validated by docking investigations, which revealed that the selected compounds exhibited high binding free energy with the enzymes tested. Finally, it was found that T. falconeri is a viable industrial crop with potential use in the production of functional goods and nutraceuticals.

In Vitro Antiviral and Anticancer Effects of Tanacetum sinaicum Essential Oil on Human Cervical and Breast Cancer.

BACKGROUND: Cervical cancer has been linked to human papillomavirus (HPV) types 16 and 18. Essential oils (EOs) are vital natural products of plants with various therapeutic and biological properties. OBJECTIVES: The purpose of this study is to investigate and assess Tanacetum sinaicum essential oil's possible antiviral and anticancer properties, with a focus on its in vitro effects on human cervical cancer and human breast adenocarcinoma cell lines. MATERIALS AND METHODS: Tanacetum sinaicum EO was extracted via hydrodistillation (HD) and characterized using gas chromatography-mass spectrometry (GC-MS). MTT assay was used to determine the cell viability of Hela (a human epithelial cervical cancer) and MCF-7 (human breast adenocarcinoma) cell lines. Quantitative real-time polymerase chain reaction (PCR) was utilized to assess the antiviral efficacy of EO against HPV-16 and 18, and anti-metastatic characteristics. The biological activity of EO was assessed using Autophage and Cell genotoxicity via the comet assay. RESULTS: EO is mostly composed of chrysanthenyl acetate, thujone, and verbenol. The cell viability was reduced after 24 hours of incubation at doses from 100 to 400 µg/ml. Concentrations of 800 to 3,200 µg/ml significantly inhibit cell growth. After a 24-hour incubation period, doses ranging from 100 to 400 µg/ml reduced cell viability from 62 to 72%. Concentrations of 800 to 3,200 µg/ml significantly suppress cell growth by over 95%. In MCF7 and HeLa cell lines, EO lowered virus copy numbers in a dose-dependent manner, with higher concentrations of the oil inhibiting virus replication more effectively. EO treatment increased the number of autophagosomes/autolysosomes and acidic vesicular organelles in both cell lines. On the HeLa and MCF7 cell lines, EO demonstrated antiproliferative and antimetastatic effects. The results demonstrated that EO had dose-dependent genotoxic effects on both cancer cell lines, as evidenced by DNA damage. CONCLUSION: Tanacetum sinaicum EO is a prospective source of natural bioactive compounds that can be employed in pharmaceutical and medicinal applications due to its antiviral, antiproliferative, anti-metastatic and genotoxic properties.

Chemodiversity in flowers of Tanacetum vulgare has consequences on a florivorous beetle.

The chemical composition of plant individuals can vary, leading to high intraspecific chemodiversity. Diversity of floral chemistry may impact the responses of flower-feeding insects. Tanacetum vulgare plants vary significantly in their leaf terpenoid composition, forming distinct chemotypes. We investigated the composition of terpenoids and nutrients of flower heads and pollen in plants belonging to three chemotypes - dominated either by ß-thujone (BThu), artemisia ketone (Keto) or a mixture of (Z)-myroxide, santolina triene, and artemisyl acetate (Myrox) - using different analytical platforms. We tested the effects of these differences on preferences, weight gain and performance of adults of the shining flower beetle, Olibrus aeneus. The terpenoid composition and diversity of flower heads and pollen significantly differed among individuals belonging to the above chemotypes, while total concentrations of pollen terpenoids, sugars, amino acids, and lipids did not differ. Beetles preferred BThu over the Myrox chemotype in both olfactory and contact choice assays, while the Keto chemotype was marginally repellent according to olfactory assays. The beetles gained the least weight within 48 h and their initial mortality was highest when feeding exclusively on floral tissues of the Myrox chemotype. Short-term weight gain and long-term performance were highest when feeding on the BThu chemotype. In conclusion, the beetles showed chemotype-specific responses towards different T. vulgare chemotypes, which may be attributed to the terpenoid composition in flower heads and pollen rather than to differences in nutrient profiles. Both richness and overall diversity are important factors when determining chemodiversity of individual plants and their consequences on interacting insects.

A new eudesmanolide from Tanacetum balsamita L. and biological activities of extracts.

The ethyl acetate and methanol extracts from aerial parts of Tanacetum balsamita yielded a new derivative of 1-acetyl-erivanin, namely 1-acetyl-3-epi-erivanin (17), some known compounds, namely seventeen sesquiterpene lactones, five flavonoids, four coumarins, and a steroid. All extracts displayed antibacterial activity against test microorganisms except for Escherichia coli. The methanol (TBM) extract with an IC50 value of 0.180 mg/mL exhibited good antioxidant activity against DPPH radical while all extracts showed significant anti-inflammatory activity against lipoxygenase enzyme. The ethyl acetate (TBEA) extract presented moderate activity against α-glucosidase enzyme with an IC50 of 0.808 mg/mL. The highest total phenol content with 91.050 mg GAE/g extract was found in TBM. It is the first study on the isolation of secondary metabolites as well as 5-lipoxygenase and α-glucosidase inhibitory activity of T. balsamita growing in Turkey.

Profiling of the essential oil compositions from the flowers and leaves of Tanacetum fisherae Aitch. & Hemsl., an endemic plant in Kerman province, Iran.

Tanacetum fisherae Aitch. & Hemsl. is an endemic plant growing wild in some brackish regions of Iran. Since there are not enough reports concerning the quantitative and qualitative analyses of its essential oil, it was decided to characterise the respective water-distilled oils obtained from the flowers and leaves of this medicinal plant. Characterisation of the corresponding essential oil profiles revealed that in both of the analysed oils, oxygenated monoterpenes constituted most of the chemical profiles. In this sense, the most prevailing natural compounds in the flower oils were cis-p-2-menthen-1-ol (11.2%), trans-p-2-menthen-1-ol (10.7%), trans-piperitol (7.8%), 1,8-cineole (6.1%), cis-piperitol (3.8%), α-terpineol (3.7%) and terpinene-4-ol (2.1%), whereas the main constituent components of the leaves oils were, respectively, 1,8-cineole (16.7%), cis-p-2-menthen-1-ol (14.6%), trans-p-2-menthen-1-ol (10.4%), trans-piperitol (12.8%), α-terpineol (5.4%), cis-piperitol (2.9%), borneol (2.7%), and terpinene-4-ol (2.1%). In addition, the second rank of natural compound constituting groups was due to oxygenated sesquiterpenes, as well.[Formula: see text].

Essential Oils and Supercritical CO2 Extracts of Arctic Angelica (Angelica archangelica L.), Marsh Labrador Tea (Rhododendron tomentosum) and Common Tansy (Tanacetum vulgare)-Chemical Compositions and Antimicrobial Activities.

Traditionally, arctic Finnish Angelica (Angelica archangelica L.), marsh Labrador tea (Rhododendron tomentosum, syn. Ledum palustre) and common tansy (Tanacetum vulgare) have been used as medicinal herbs in folklore medicine. However, these underutilised plants are a source of, e.g., oil-based compounds, which could benefit many modern applications implemented by the green chemistry extraction methods, as well. We extracted Angelica, marsh Labrador tea and common tansy by non-toxic and recyclable extraction methods, i.e., hydrodistillation and supercritical carbon dioxide (scCO2) extraction; characterised the essential oils (EOs) and scCO2 extracts by combination of gas chromatography and mass spectrometry (GC-MS), and in addition, analysed the antimicrobial properties. As expected for Angelica root and common tansy inflorescence, the scCO2 extraction method produced less amount of volatile compounds compared to hydrodistillation. On the other hand, more coumarins, alkanes, fatty alcohols and fatty acids were obtained. Additionally, sesquiterpenoids palustrol and ledol were predominant compounds in both marsh Labrador tea EO and scCO2 extract. According to our results, however, all the EOs and scCO2 extracts showed broad spectrum of antimicrobial activities against the selected microbes, but the effects were extract-specific. The strongest and broadest antimicrobial activities were performed by marsh Labrador tea scCO2 extract, which showed extremely strong effect on Staphylococcusaureus subsp. aureus and strong effect on Candida albicans.

Tanacetum vulgare L. (Tansy) as an effective bioresource with promising pharmacological effects from natural arsenal.

The Tanacetum genus is a big treasure with the presence of biologically-active compounds and members of this genus are widely used for the treatment of several diseases in traditional medicine system. Considering this fact, we aimed to analyze the extracts from Tanacetum vulgare L. in case of chemical profiles and biological effects. Chemical characterization was performed by using UHPLC-HRMS technique and showed the presence of several phytochemical groups (107 compounds were identified, including phenolic acids, flavonoids, terpenoids and fatty acids. Biological abilities were examined by using antioxidant (DPPH, ABTS, FRAP, CUPRAC, metal chelating and phosphomolybdenum assays) and enzyme inhibition (tyrosinase, amylase, glucosidase and cholinesterase) properties. Pharmaco-toxicological investigations were also performed with the aim to identify limits of biocompatibility, anti-oxidant and neuromodulatory effects, in hypothalamic HypoE22 cells. A bioinformatic analysis was also carried to unravel the putative protein-targets for the observed biological effects. Generally, the tested hexane and hydroalcoholic extracts displayed stronger activities in antioxidant and enzyme inhibitory assays, when compared with water. In addition, multivariate analysis was performed to understand the differences in both solvents and plant parts and we clearly observed the separation of these parameters. The extracts (10 µg/mL) also stimulated DAT and inhibited TNFα and BDNF gene expression, in HypoE22 cells. In parallel, the extracts were also able to stimulate norepinephrine release from this cell line. By contrast, in the concentration range 50-100 µg/mL, the extracts reduced the HypoE22 viability, thus demonstrating cytotoxicity at concentrations 5-10 fold higher compared to those effective as neuromodulatory. Our observations manifested that T. vulgare has several beneficial effects and it can be used as a potential natural raw material for designing further health-promoting applications in nutraceutical, cosmeceutical, and pharmaceutical areas.

Parasiticidal effects of Tanacetum vulgare extract against Ichthyophthirius multifiliis.

Ichthyophthiriasis, which is caused by Ichthyophthirius multifiliis (Ich) infections, has a severe impact on productivity in freshwater aquaculture. These infections were previously treated effectively with malachite green, a compound that is now banned on fish farms due to its carcinogenicity. To find efficacious drugs to control Ich, flowers of tansy Tanacetum vulgare were evaluated for their antiprotozoal activity. Tanacetum vulgare extract significantly reduced the survival of Ich trophonts and theronts. In vitro, the extract killed all trophonts at 3200 mg l-1, terminated tomont reproduction at 50 mg l-1, and caused mortality of all theronts at 100 mg l-1. T. vulgare extract may be a new and efficacious drug for the control of Ich.

In†vitro Antioxidant and Cytotoxic Activities of Extracts of Endemic Tanacetum erzincanense Together with Phenolic Content by LC-ESI-QTOF-MS.

In this study, phenolic composition, and in vitro biological activities of ethyl acetate (EAE) and methanol (ME) extracts obtained from the aerial parts of endemic Tanacetum erzincanense were investigated. Total phenolic and flavonoid content of the extracts were determined by Folin-Ciocalteu and aluminum chloride colorimetric methods, respectively. Antioxidant capacity of the extracts was evaluated over radical scavenging (DPPH and ABTS) and metal ion reducing power (FRAP and CUPRAC) tests. Individual phenolic compounds in ME was analyzed by high-performance liquid chromatography coupled to electrospray ionization quadrupole time-of-flight mass spectrometry (LC-ESI-QTOF/MS). Cell inhibitory potential of the extracts was tested against colorectal adenocarcinoma (HT-29), breast adenocarcinoma (MCF-7), and hepatocarcinoma (HepG2) cells by 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide (XTT) assay. The results showed that ME contains higher TPC (64.4 mg GAE/g) and TFC (62.2 mg QE/g) than those of EAE (41.5 mg GAE/g and 40.0 mg QE/g). LC-ESI-QTOF/MS analysis revealed that ME is rich in phenolic compounds, namely, chlorogenic acid, apigenin, quercetin, luteolin, and diosmetin. Antioxidant assay results indicated that ME possess stronger activity than EAE and a power that competes with synthetic antioxidants. XTT assay results demonstrated that although both extracts displayed a considerable cytotoxicity against the tested cancer cell lines in a time and dose-dependent manner, ME expressed its selective inhibitory action towards MCF-7 cells with an IC50 value of 20.4 µg/mL for 72 h. These results may serve as a basis for further in vivo studies to examine the potential applications of T. erzincanense in food and pharmaceutical industries.

Repellent activity of Tanacetum parthenium (L.) and Tanacetum vulgare (L.) essential oils against Leptinotarsa decemlineata (Say).

The Colorado potato beetle, Leptinotarsa decemlineata (Say), is one of the most destructive pest species to have developed resistance to most chemical insecticides. We determined the composition and evaluated the potential of Tanacetum parthenium L. and Tanacetum vulgare L. (Asteraceae family) essential oil (EO) application as an alternative eco-friendly control strategy against L. decemlineata. We assessed the antifeedant activity for L. decemlineata larvae and adults by estimating the damage to potato leaves treated with three concentrations of EOs dissolved in ethanol (0.125, 0.25 and 0.5%). Results showed that T. parthenium EO was more effective against larvae, and T. vulgare was more effective against adults. In an olfactometer assay, the time required to choose an untreated leaf disc did not depend on the Tanacetum species, or life stage examined. However, the concentration of EO exhibited a significant effect on the behaviour of both developmental stages. At higher EO concentrations, both third instar larvae and adults require less time to choose an untreated leaf disc. Additionally, T. parthenium EO provoked more rapid movement away from the treated leaf disc than T. vulgare, especially at the highest concentration. Successful modification of L. decemlineata behaviour by the two Tanacetum oils suggests that they possess the potential for use in potato protection.

In vitro cultivation of tansy (Tanacetum vulgare L.): a tool for the production of potent pharmaceutical agents.

In this study, tansy (Tanacetum vulgare L.) in vitro culture was established from seeds collected from natural populations. The multiplication of plantlets was conducted through shoot tips that exhibited potent apical growth and regeneration capacities on basal medium (BM), without the addition of any plant growth regulators (PGRs). PGRs were also omitted for the establishment and cultivation of tansy root cultures. Both abaxial and adaxial leaf surfaces of in vitro micropropagated plantlets were covered with glandular biseriate trichomes. Histochemical staining showed that glandular secretions were rich in lipid and terpene compounds, confirmed by GC-MS analysis of essential oil (EO). In the total EO, similar portions of oxygenated monoterpenes (38.5% m/m) and oxygenated sesquiterpenes (22.6% m/m) were detected. Chemical profiles of methanol extracts of in vitro cultured tansy shoots and roots varied in quantity and quality from those obtained from wild-growingtansy. HPLC analysis indicated that the methanol extracts of in vitro cultured roots were the richest in 3,5-O-dicaffeoylquinic acid (3,5-O-DCQA), in which the concentration was 6 times higher (10.220 mg/g DW) than that in the extract obtained from roots of wild-growing tansy (1.684 mg/g DW). This result is noticeable in the manner of industrial production of biologically active 3,5-O-DCQA that has been shown to have antioxidant, hepatoprotective, antiviral, antimutagenic, and immunomodulatory activity. Biotechnological interventions on secondary metabolite production taking place in trichomes could further enhance the production of some important tansy metabolites and further investigation will be directed toward the elucidation of the pharmaceutical potential of tansy in vitro obtained metabolites, as mixtures or single moieties.

[The effect of pectin of tansy, Tanacetum vulgare L., on anxiety and overeating food rich in fats and sugars in mice in modelling binge eating].

Binge eating is repeated episodes of eating large amounts of sweet and fatty food in short periods. Dietary fibers, including pectin, significantly reduce the subjective ratings of hunger, and the amount of food eaten. However, studies showing the effect of dietary fibers on satiety use juices or yoghurts with added dietary fiber, or a kissel-like food. Thus, there is a lack of data on the effect of dietary fibres on binge eating of palatable food. The aim of the study was to assess the effect of tansy pectin on anxiety and the binge eating of palatable food in mice. Material and methods. 64 mice weighing 33.3±0.6 g were divided into two groups. Binge eating was induced in forty mice of the first group by consumption of sunflower halva (SH) in addition to regular chow for 24 h once a week. The total energy intake and separately the consumption of regular chow (RC) and SH were monitored. Tansy pectin in the form of an aqueous solution was administered to the mice using a gastric feeding tube (50 mg/kg body weight) before the last presentation of SH. Blood was obtained by cardiac puncture at the end of the last 24 h SH access period. The concentration of insulin and ghrelin in plasma samples were determined by the enzyme immunoassay. In animals of the second group, 24 hours after the administration of pectin, the level of anxiety and depression of mice was assayed with an open field test, a light-dark box test, an elevated plus-maze test, and a forced swim test. Throughout the study, water was used as a negative control, and imipramine at a dose of 20 mg/kg was used as a positive control. Results. Mice treated with tansy pectin ate 2.6 fold less SH within 3 h and 1.4 fold less within 24 h after oral administration of tansy pectin compared to control (water administration). Consumption of RC did not differ within 3 or 24 h. The total energy intake was 1.9 fold lower within 3 h in mice treated with tansy pectin. Within 24 h after pectin oral administration the total energy intake did not differ from control. Insulin plasma level was 2.5 fold lower and ghrelin plasma concentration was 25% higher in the mice that received pectin compared to control, at the end of the 24 h SH access period. The administration of tansy pectin was found to decrease anxietyrelated behaviour in mice. Its administration significantly increased the time spent in the central sector of the open field apparatus by 87%, the time spent in the light area of the light-dark box by 31%, and the time spent on the open arms of the elevated plus maze by 22% compared with the control. Conclusion. Overall, tansy pectin reduced the binge eating of SH representing highly palatable, sweet, and fatty food. Reduced intake SH lead to a decrease in insulin concentration. Blood level of ghrelin was increased in mice treated with tansy pectin at the end of the sweet and fatty food presentation period. Tansy pectin reduced the level of anxiety in mice.

Antifungal and Synergistic Effects of the Ethyl Acetate Extract of Tanacetum vulgare (L.) Against Candida albicans.

BACKGROUND With the continued demand for new, effective, and safe endodontic therapies, the aim of this study was assessment of efficiency of the ethyl acetate (EthOAc) extract of Tanacetum vulgare (L.) against Candida albicans. MATERIAL AND METHODS The antifungal effectiveness of the EthOAc extract of T. vulgare was determined using the agar disk diffusion method. The inhibition zones induced by the EthOAc extract were compared after 5 minutes, 60 minutes, and 24 hours to those induced by standard solutions (2% chlorhexidine, saturated calcium hydroxide, and 2% sodium hypochlorite). Statistical analysis of the results was performed using the Kruskal-Wallis test and one-way ANOVA. RESULTS The inhibition zone of chlorhexidine against C. albicans was 30.3-19.3 mm, but in combination with EthOAc extract (100 mg/mL) of T. vulgare, this inhibition was from 32.7-30 mm, indicating that this combination exerted a marked synergistic effect against C. albicans. The inhibition zone of sodium hypochlorite (69.7-65 mm) was higher than the inhibition zone of EthOAc extract and chlorhexidine. The combination of EthOAc extract with sodium hypochlorite resulted in a loss of antifungal activity. Furthermore, the activity of the EthOAc extract against C. albicans was decreased after mixing the extract with dentine at a concentration of 25 mg/50 µL (30.3-20.7 mm). The EthOAc extract did not show a genotoxic effect on lymphocyte cells. CONCLUSIONS The EthOAc extract of T. vulgare may be a useful tool to discover natural bioactive agents that have antifungal activity against C. albicans and could be used as endodontic therapies.

Ultraviolet inflorescence cues enhance attractiveness of inflorescence odour to Culex pipiens mosquitoes.

Inflorescence patterns of ultraviolet (UV) absorption and UV-reflection are attractive to many insect pollinators. To understand whether UV inflorescence cues affect the attraction of nectar-foraging mosquitoes, we worked with the common house mosquito, Culex pipiens and with two plant species exhibiting floral UV cues: the tansy, Tanacetum vulgare, and the common hawkweed Hieraciumm lachenalii. Electroretinograms revealed that Cx. pipiens eyes can sense UV wavelengths, with peak sensitivity at 335 nm. Behavioural bioassays divulged that UV inflorescence cues enhance the attractiveness of inflorescence odour. In the presence of natural floral odour, female Cx. pipiens were attracted to floral patterns of UV-absorption and UV-reflection but preferred uniformly UV-dark inflorescences. Moreover, Cx. pipiens females preferred UV-dark and black inflorescence models to UV-dark and yellow inflorescence models. With feathers and pelts of many avian and mammalian hosts also being UV-dark and dark-coloured, foraging Cx. pipiens females may respond to analogous visual cues when they seek nectar and vertebrate blood resources.

Comparison of high-performance thin-layer with overpressured layer chromatography combined with direct bioautography and direct analysis in real time mass spectrometry for tansy root.

Bioactive polyacetylenes in tansy (Tanacetum vulgare L.) root extract were separated by overpressured layer chromatography (OPLC) with better resolutions than achievable by capillary flow high-performance thin-layer chromatography (HPTLC). OPLC enabled a longer development distance in a shorter time (16 cm, 7 min) in comparison to conventional HPTLC (7 cm, 16 min). OPLC separations on HPTLC plates with spherical particles resulted in higher resolutions than on such with irregular particles. A slight distortion of zones sometimes occurred that could be eliminated by sonication of the mobile phase through removal of the dissolved air. However, zone distortion did not diminish the meaning of the qualitative outcome. The combination of OPLC with direct bioautography and direct analysis in real time-high resolution mass spectrometry (DART-HRMS) led to the determination of the individual polyacetylenes responsible for the diverse effects. In each recorded mass spectrum, the basepeak was the respective protonated molecule. The assignments confirmed the results of a previous study, however, compounds TR5a (tetradeca-2,4,6-triine-8-en-12-one) and TR5b (trans-2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4,5]dec-3-ene) that were not separable by HPTLC were partially separated by OPLC. Thus, it was proven that TR5b was not an oxidation product of TR5a and thus not formed as artefact during the HPTLC-DART-HRMS analysis, but originally present in the sample.

Antiprotozoal Germacranolide Sesquiterpene Lactones from Tanacetum sonbolii.

A phytochemical investigation of extracts from flowers and aerial parts of Tanacetum sonbolii afforded 7 new germacranolide sesquiterpene lactones. The structures were established by a combination of 1- and 2-dimensional nuclear magnetic resonance spectroscopy, high-resolution mass spectrometry, and electronic circular dichroism. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and cytotoxicity against rat myoblast (L6) cells were determined. Compounds 4: and 5: showed IC50 values of 5.1 and 10.2 µM and selectivity indices of 3.9 and 4.0, respectively.

Chemical composition and antimicrobial activity of the essential oil of Tanacetum walteri (Anthemideae-Asteraceae) from Iran.

The composition and antimicrobial activity of the essential oil of Tanacetum walteri were studied. Aerial flowering parts of plant were collected from North Khorasan Province of Iran and the essential oil was isolated by hydrodistillation and analysed by GC-FID and GC-MS. Antimicrobial activity of the essential oil was determined by disc diffusion and MIC and MBC determination. Thirty-five compounds were identified in the oil of T. walteri accounting for 94.4% of the total oil. Thymol (22.5%), 1,8-cineole (8.2%), umbellulone (6.9%), α-bisabolol (6.3%) and camphor (5.3%) were as the principal constituents. The highest antimicrobial activity of the essential oil was observed against Staphylococcus aureus, Enterococcus faecalis and Klebsiella pneumoniae with MIC value of 0.63 mg/mL. The inhibitory effect of the essential oil of T. walteri could be attributed mainly to the high levels of phenolic compound thymol and oxygenated terpenes in essential oil.

Chemical diversity of the essential oils of twenty populations of Tanacetum polycephalum Sch. Bip. from Iran.

Chemical diversity of the essential oils of twenty wild populations of Tanacetum polycephalum Sch. Bip., was investigated. The aerial parts of T. polycephalum were collected at full flowering stage from West Azerbaijan Province of Iran, air-dried; hydrodistilled to produce essential oils. The essential oils were analyzed by GC-FID and GC-MS. A total of forty compounds were identified accounting for 96.4-99.9% of the total oils. The most principal compounds were cis-thujone (0-82.3%), trans-thujone (0-79.8%), camphor (1.3-75.0%), 1,8-cineole (4.5-43.3%), borneol (1.0-36.2%) and bornyl acetate (0-26.8%). Hierarchical cluster analysis based on the percentages (>0.5%) of the essential oils components was carried out to determine the chemical diversity among the populations studied. The cluster analysis resulted in the identification of four main chemotypes namely: 'camphor + 1,8-cineole', 'mixed', 'cis-thujone' and 'trans-thujone'.

Aphid infestation leads to plant part-specific changes in phloem sap chemistry, which may indicate niche construction.

Phloem sap quality can differ between and within plants, and affect the performance of aphids. In turn, aphid infestation may change the chemical composition and nutritional value of phloem sap. However, the effects of different aphid species on the overall phloem sap composition of distinct parts within plant individuals in relation to aphid performance remain unclear. To test the specificity of plant responses to aphids, we used two chemotypes of Tanacetum vulgare plants and placed the monophagous aphids Macrosiphoniella tanacetaria and Uroleucon tanaceti on different plant parts (stems close to the inflorescence, young and old leaves). Aphid population growth was determined and sugars, organic acids, amino acids and metabolic fingerprints of phloem exudates were analysed. Macrosiphoniella tanacetaria performed best on stems, whereas U. tanaceti performed best on old leaves, indicating differences in niche conformance. Aphid infestation led to distinct changes in the phloem exudate composition of distinct metabolite classes, differing particularly between plant parts but less between chemotypes. In summary, plant responses to aphids are highly specific for the chemotype, plant part, metabolite class and aphid species. These changes may indicate that aphids construct their own niche, optimizing the food quality on the plant parts they prefer.

Parthenolide Influences Herpes simplex virus 1 Replication in vitro.

BACKGROUND/AIMS: Parthenolide is a sesquiterpene lactone that is present in plants of the Tanacetum genus, for which many biological effects have already been reported, including antiherpetic activity. Although the effectiveness of parthenolide against Herpes simplex virus 1 (HSV-1) has already been demonstrated, such findings are still controversial. The objective of this study was to investigate the ways in which parthenolide exerts anti-HSV-1 activity. METHODS: The cytotoxicity and antiviral activity of parthenolide were determined by the MTT method and plaque reduction assay, respectively. The expression of cell and viral proteins during the treatment of infected cells was investigated by Western blot. RESULTS: Both strains of HSV-1 were sensitive to parthenolide, and parthenolide was active only after penetration of the virus into the host cell. The expression of p65 protein decreased, the expression of caspases 8 and 9 increased, and the expression of c-Jun N-terminal kinase (JNK) and p38 protein was altered in infected cells after parthenolide treatment, resulting in lower cell survival. The low expression of viral proteins gB, gD, and ICP0 confirmed the reduction of HSV-1 particle production. CONCLUSION: Parthenolide exerts anti-HSV-1 activity by impairing cell viability, which consequently interferes with the efficient infection and production of new viral particles.