Parthenolide from the aerial parts of Tanacetum larvatum

The chemical composition and antifungal activity of volatile extracts of Tanaceutum audibertii (Req.) DC., an endemic species of Sardinia and Corsica islands, were investigated.

The extract and the essential oil, obtained respectively by supercritical fluid extraction with carbon dioxide (SFE) at pressures of 90 bar and temperature of 40 °C and by hydrodistillation (HD), were analyzed by GC/FID and GC/MS. Artemisia ketone, trans-linalyl oxide acetate and 1,8-cineole were the main components.

The HD oil was evaluated against yeasts and dermatophyte strains, being more active against Cryptococcus neoformans, with MIC and MLC values of 0.64 μL/mL. Moreover, the oil revealed an important inhibitory effect on germ tube formation in C. albicans at sub-inhibitory concentrations. At the concentration of 1/16 MIC the inhibition of filamentation was more than 70% in comparison to untreated control cells.

Aerial parts of Tanacetum oshanahanii collected at “Jardín Canario Viera y Clavijo”, Tanacetum ptarmiciflorum collected at Los Moriscos (Tejeda), and Tanacetum ferulaceum var. latipinnum collected at Anden Verde (Agaete) in Gran Canaria, Canary Islands, afforded three sesquiterpenes related to nerolidol and six sesquiterpene lactones whose structures were established on the basis of their spectroscopic data and chemical transformations. In this work we show that this type of sesquiterpene lactones could be used as chemotaxonomic markers. A series of sesquiterpene lactones described in this paper were assessed for cytotoxicity against HL-60 and U937 cancer cell lines. The derivatives 106a and 98a displayed cytotoxic properties showing IC₅₀ values between 5 and 11 μM. Furthermore, we demonstrated that these selected sesquiterpene lactones induce apoptotic cell death in human leukemia cells through a mechanism that involves activation of multiple caspases and moreover cell death was found to be associated with the release of cytochrome c.

The main objectives were to collect information on the use of wild growing medicinal plants by local people living in high mountain region of Montenegro and conduct local botanical and ecological surveys. Active ingredients of plant species officinal in European Pharmacopoeia 6.0 (Ph. Eur. 6.0) were studied and we assessed possibilities for commercial exploitation for local economic development.

The 75 people that were interviewed (40–82 years old) identified 94 species for treatment of various human ailments. For each named species, the following elements are provided: botanical name, family, part(s) used, medicinal use and perceived property, listing in published pharmacopoeias, the relative abundance of each species and locality where the plant was collected. Chemical analyses were done according to prescriptions of Ph. Eur. 6.0 in order to estimate potential commercial use of native plants.

The most common in traditional usage were Rosaceae (11 species) making 11.7%, Asteraceae (10 species) 10.6% and Lamiaceae (7 species) 7.4%. From 94 species reported, 35 (37.2%) are officinal in Ph. Eur. 6.0 and 12 in national pharmacopoeias (12.8%). Aerial parts were mostly used (43.6%). The most frequently reported medicinal uses were for treating gastrointestinal (57.4%) and respiratory diseases (41.5%).

The antioxidant activities of ethanolic extract of six species of Tanacetum (T. budjnurdense, T. hololeucum, T. chiliophyllum, T. sonboli, T. tabrisianum, T. kotschyi) from Iran were examined by employing various established in vitro assay systems. The results showed that all Tanacetum extracts displayed antioxidant activities, with IC₅₀ values ranging from 59.55 to 157.24 μg/ml, using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The extract of T. hololeucum, with an IC₅₀ value of 59.55 μg/ml was nearly two or three times more active than the other used Tanacetum extracts. The amounts of total phenolics and total flavonoids were also determined by spectrophotometer. A similar order of the amounts of phenolics and flavonoids in all plant extracts were found. The results showed that the extent of antioxidant activities is in accordance with the amounts of phenolics and flavonoids existing in all plant extracts. Regarding high performance liquid chromatography (HPLC) data, caffeic acid, ferulic acid, luteolin, apigenin and rutin were detected as major phenolic compounds in all the species investigated. Pretreatment of K562 cells with various concentrations of Tanacetum extracts (10–100 μg/ml) for 16 h prevent cell damage and enhanced activity of antioxidant enzymes induced by a treatment with H₂O₂. Moreover, lower level of glutathione caused by hydrogen peroxide in K562 cells were partly recovered by a pretreatment of cells with various Tanacetum species extract. These results may show the significant protection effect of Tanacetum sp. against oxidation of the cells.

Antifeedant activities of Tanacetum cadmeum ssp. cadmeum, Tanacetum parthenium, Tanacetum corymbosum ssp. cinereum, Tanacetum chiliophyllum var. chiliophyllum, Tanacetum kotschyi and Tanacetum cadmeum ssp. orientale were assessed on Spodoptera littoralis Boisd. (Lep: Noctuidae) third instar larvae. The highest antifeedant activities were found as 62 and 55.05% in the extracts of MeOH with T. cadmeum ssp. cadmeum aerial parts, MeOH with T. corymbosum ssp. cinereum flowers, respectively. Bioassay guided investigations on Tanacetum cadmeum ssp. cadmeum afforded three eudesmanolides; artesin (1), taurin (2), and artemin (3), three germacranolides; tavulin (4), tanachin (5), and tamirin (6), the coumarin; scopoletin (7), and two flavonol derivatives; tanetin (6-hydroxykaempferol 3,7,4′-trimethylether) (8) and 6-hydroxykaempferol 3,6-dimethylether (9). The structures of the compounds were elucidated by spectral methods, such as IR, UV, ¹H NMR and ¹³C NMR (COSY, APT, DEPT, HMQC, HMBC, NOE, X-ray, EIMS, CIMS and HRMS). In this paper, the antifeedant activities of some Tanacetum species and the compounds isolated from T. cadmeum ssp. cadmeum are reported.