A dichloromethane extract of root celery yielded falcarinol, falcarindiol, panaxydiol, and the new polyacetylene 8-O-methylfalcarindiol. The structure of the new compound was established by one- and two-dimensional (1D and 2D) NMR, mass spectrometry, and optical rotation data. Nonpolar extracts of roots and bulbs of carrots, celery, fennel, parsley, and parsnip were investigated for their content of polyacetylenes by high-performance liquid chromatography with diode array detection (HPLC-DAD). All five species contained polyacetylenes, although carrots and fennel only in minor amounts. Additionally, the cytotoxicity of the four polyacetylenes against five different cell lines was evaluated by the annexin V-PI assay. Falcarinol proved to be the most active compound with a pronounced toxicity against acute lymphoblastic leukemia cell line CEM-C7H2, with an IC(50) of 3.5 micromol/L. The possible chemopreventive impact of the presented findings is discussed briefly.
Plants in alpine habitats are exposed to many environmental stresses, in particular temperature and radiation extremes. Recent field experiments on Arnica montana L. cv. ARBO indicated pronounced altitudinal variation in plant phenolics. Ortho-diphenolics increased with altitude compared to other phenolic compounds, resulting in an increase in antioxidative capacity of the tissues involved. Factors causing these variations were investigated by climate chamber (CC) experiments focusing on temperature and ultraviolet (UV)-B radiation. Plants of A. montana L. cv. ARBO were grown in CCs under realistic climatic and radiation regimes. Key factors temperature and UV-B radiation were altered between different groups of plants. Subsequently, flowering heads were analyzed by HPLC for their contents of flavonoids and caffeic acid derivatives. Surprisingly, increased UV-B radiation did not trigger any change in phenolic metabolites in Arnica. In contrast, a pronounced increase in the ratio of B-ring ortho-diphenolic (quercetin) compared to B-ring monophenolic (kaempferol) flavonols resulted from a decrease in temperature by 5 degrees C in the applied climate regime. In conclusion, enhanced UV-B radiation is probably not the key factor triggering shifts in the phenolic composition in Arnica grown at higher altitudes but rather temperature, which decreases with altitude.
In continuation of our studies of altitudinal effects on secondary metabolite profile of flowering heads from taxa of the Asteraceae, we investigated phenolic contents and radical scavenging potential from cultivated plants of Arnica montana cv. ARBO during the growing seasons 2003, 2004, and 2005. By conducting experiments on potted plants, we excluded that differences in phenolic contents from plants grown at different altitudes were related primarily to differences in soil composition at these sites. To assess altitudinal and interseasonal variation, plants of A. montana cultivar ARBO were grown in nine experimental plots at altitudes between 590 and 2,230 m at Mount Patscherkofel near Innsbruck, Austria. In all growing seasons and regardless of the soil the plants were grown in, the proportion of flavonoids with vicinal-free hydroxy groups in ring B to flavonoids lacking this feature, and the total amount of caffeic acid derivatives, significantly increased with elevation. These increases of antioxidant phenolics corresponded to an increase of the radical scavenging potential of extracts from plants grown at different altitudes. The results are discussed in regard to previous studies that suggest that enhanced UV-B radiation and decreased temperatures trigger augmented biosynthesis of UV-absorbing and antioxidant phenolics in higher plants.
Phenolic acid composition, antioxidant, and cytotoxic activities in leaves of four (Crassulaceae) species were evaluated. Determination of phenolic acid contents were conducted by an optimized LC-ESI-MS/MS method. The results show that Raym.-Hamet & H. Perrier (using ASE extraction) and (Lam.) Pers. contain the highest amounts of phenolic acids, while Engl. the lowest ones. Among phenolic acids ferulic, caffeic and protocatechuic acids were occurring in the highest quantities in the analysed species. The greatest amounts of ferulic and protocatechuic acids were found in and Moreover, the antiradical and cytotoxic activities of extracts were investigated. All tested extracts possessed antioxidant activity. The obtained IC values (μg/mL) ranged from 49.9 μg/mL to 1410 μg/mL, indicating a large variation of the activity of the analysed extracts. Cytotoxicity assays revealed dose-dependent effects in the cells lines tested. Only extract showed a high cytotoxicity against the H-9 human T cell line. Other extracts (, ,) showed more pronounced cytotoxicity towards J45.01 cells (human acute lymphoblastic leukaemia T cells). The present study demonstrated that extracts have significant antioxidant and cytotoxic effects. This suggests that these species can be used as new sources of natural antioxidants and potential anticancer compounds.
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