lignans and 1-phenylpropanol

Extracts of

Topics: Estrogen Receptor alpha; Estrogen Receptor beta; Humans; Lignans; MCF-7 Cells; Models, Molecular; Molecular Docking Simulation; Peperomia; Phytoestrogens; Propanols

An effective strategy based on high-speed counter-current chromatography (HSCCC) knockout combination with HPLC-DAD-QTOF-MS/MS analysis were developed to identify minor lignans, alkaloids, and phenylpropanoid glycosides in M. officinalis. Petroleum ether/ethyl acetate/methanol/water (8:4:7:5, v/v/v/v) as solvent system was firstly selected to separate the crude extract of M. officinalis. Two major lignans, honokiol and magnolol were knocked out, and minor components were enriched. Then, five standards (honokiol, magnolol, magnocurarine, magnoflorine and acteoside) were used as examples to discuss their fragmentation patterns for structural identification. By comprehensive screening, sixteen lignans, nine alkaloids, six phenylpropanoid glycosides were unambiguously or tentatively identified by comparing their retention time, UV spectra, accurate mass and fragmentation patterns with standards or reported components. Eight of them, as far as was known, were discovered from M. officinalis for the first time. The proposed method might provide a model for the effective identification of minor components from complex herbs. Additionally, this study laid a foundation for the study of quality control, and clinical applications of M. officinalis.

Topics: Alkaloids; Aporphines; Biphenyl Compounds; Chromatography, High Pressure Liquid; Glucosides; Glycosides; Isoquinolines; Lignans; Magnolia; Methanol; Phenols; Propanols; Tandem Mass Spectrometry

The present investigation of the chemical constituents of the stem barks of Ailanthus altissima has resulted in the isolation of six canthinone-type alkaloids, including a new compound, (R)-5-(1-hydroxyethyl)-canthine-6-one (1), and five known compounds (2-6). Moreover, four phenyl propanoids (7-10), two lignans (11 and 12), two triterpenoids (13 and 14) and a fatty acid (15) having previously known chemical structures were isolated during the same course of this study. The structure of the new compound was elucidated by physical (m.p., [α]D) and spectroscopic data (¹H-NMR, (13)C-NMR, 2D NMR, and HR-DART-MS) interpretation and its absolute configuration was determined by electronic circular dichroism (ECD) data and quantum chemical calculations. The inflammatory activities of the isolates were screened on lipopolysaccharide (LPS)-induced nitric oxide (NO), a proinflammatory mediator, in RAW 264.7 cells. Among these isolated compounds, six compounds exhibited significant inhibition of NO production, with IC50 values in the range of 5.92 ± 0.9 to 15.09 ± 1.8 μM.

Topics: Ailanthus; Alkaloids; Animals; Inflammation; Lignans; Magnetic Resonance Spectroscopy; Mice; Plant Bark; Plant Extracts; Propanols; RAW 264.7 Cells; Triterpenes

We examined the effects of ambient, non-stressing ultraviolet (UV)-B (280-315nm) level combined with different intensities of photosynthetic active radiation (PAR, 400-700nm) on the accumulation of the lignan (-)-hinokinin, in leaves and stems of Hydrocotyle leucocephala. Plants were exposed in sun simulators under almost natural irradiance and climatic conditions to one of four light regimes, i.e. two PAR intensities (906 and 516μmolm(-2)s(-1)) including or excluding UV-B radiation (0 and 0.4Wm(-2)). Besides hinokinin, we identified three chlorogenic acid isomers, one other phenolic acid, 12 quercetin, and five kaempferol derivatives in the H. leucocephala extracts. Hinokinin was most abundant in the stems, and its accumulation was slightly enhanced under UV-B exposure. We therefore assume that hinokinin contributes to cell wall stabilization and consequently to a higher resistance of the plant to environmental factors. Quercetin derivatives increasingly accumulated under UV-B and high PAR exposure at the expense of kaempferols and chlorogenic acids, which was apparently related to its ability to scavenge reactive oxygen species. In general, the concentration of the constituents depended on the plant organ, the leaf age, the light regimes, and the duration of exposure. The distribution pattern of the compounds within the examined organs was not influenced by the treatments. Based on the chemical composition of the extracts a principal component analysis (PCA) enabled a clear separation of the plant organs and harvesting dates. Younger leaves mostly contained higher phenylpropanoid concentrations than older leaves. Nevertheless, more pronounced effects of the light regimes were detected in older leaves. As assessed, in many cases the individual compounds responded differently to the PAR/UV-B combinations, even within the same phenylpropanoid class. Since this is the first report on the influence of light conditions on the accumulation of lignans in herbaceous plants, it opens many perspectives for a more precise elucidation of all involved biochemical and molecular processes.

Topics: 4-Butyrolactone; Benzodioxoles; Centella; Chlorogenic Acid; Flavonols; Hydroxybenzoates; Kaempferols; Lignans; Oxidative Stress; Photosynthesis; Plant Leaves; Plant Stems; Propanols; Quercetin; Ultraviolet Rays

Verticillium longisporum is a soil-borne vascular pathogen causing economic loss in rape. Using the model plant Arabidopsis this study analyzed metabolic changes upon fungal infection in order to identify possible defense strategies of Brassicaceae against this fungus. Metabolite fingerprinting identified infection-induced metabolites derived from the phenylpropanoid pathway. Targeted analysis confirmed the accumulation of sinapoyl glucosides, coniferin, syringin and lignans in leaves from early stages of infection on. At later stages, the amounts of amino acids increased. To test the contribution of the phenylpropanoid pathway, mutants in the pathway were analyzed. The sinapate-deficient mutant fah1-2 showed stronger infection symptoms than wild-type plants, which is most likely due to the lack of sinapoyl esters. Moreover, the coniferin accumulating transgenic plant UGT72E2-OE was less susceptible. Consistently, sinapoyl glucose, coniferyl alcohol and coniferin inhibited fungal growth and melanization in vitro, whereas sinapyl alcohol and syringin did not. The amount of lignin was not significantly altered supporting the notion that soluble derivatives of the phenylpropanoid pathway contribute to defense. These data show that soluble phenylpropanoids are important for the defense response of Arabidopsis against V. longisporum and that metabolite fingerprinting is a valuable tool to identify infection-relevant metabolic markers.

Topics: Arabidopsis; Biomarkers; Biosynthetic Pathways; Cinnamates; Coumaric Acids; Disease Resistance; Gene Expression Regulation, Plant; Genes, Plant; Glucosides; Lignans; Lignin; Metabolomics; Mutation; Phenols; Plant Diseases; Plant Leaves; Plant Vascular Bundle; Propanols; Solubility; Verticillium

In the present review, the literature data on the chemical constituents and biological investigations of the genus Pedicularis are summarized. Some species of Pedicularis have been widely applied in traditional Chinese medicine. A wide range of chemical components including iridoid glycosides, phenylpropanoid glycosides (PhGs), lignans glycosides, flavonoids, alkaloids and other compounds have been isolated and identified from the genus Pedicularis. In vitro and in vivo studies indicated some monomer compounds and extracts from the genus Pedicularis have been found to possess antitumor, hepatoprotective, anti-oxidative, antihaemolysis, antibacterial activity, fatigue relief of skeletal muscle, nootropic effect and other activities.

Topics: Alkaloids; Animals; Anti-Bacterial Agents; Antineoplastic Agents; Antioxidants; Chemical and Drug Induced Liver Injury; Fatigue; Flavonoids; Glycosides; Humans; In Vitro Techniques; Iridoid Glycosides; Lignans; Medicine, Chinese Traditional; Mice; Molecular Conformation; Nootropic Agents; Pedicularis; Phytotherapy; Plant Extracts; Propanols

Ethanol extract of the seeds of Licaria puchury-major, a Brazilian herbal medicine, was found to inhibit cell proliferation in human leukemia cell line (Jurkat) by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Bioassay-guided fractionation of the active components led to the isolation of one phenylpropanoid (1) and ten neolignans (2-11). The apoptosis-inducing activity of the compounds showing cytotoxicity in Jurkat cells was assessed by flow cytometric analysis. Among the identified neolignans, compounds 3, 4, 6 and 7 which have similar molecular structures, showed apoptotic activity. To elucidate the mechanism of apoptosis induction by neolignans, intracellular caspase-3, -8 and -9 activity in Jurkat cells was evaluated. Compound 4 markedly elevated the activity of caspase-3 and -9.

Topics: Antineoplastic Agents, Phytogenic; Apoptosis; Caspase 3; Caspase 8; Caspase 9; Cell Proliferation; Humans; Jurkat Cells; Lauraceae; Leukemia; Lignans; Molecular Structure; Phytotherapy; Plant Extracts; Propanols; Seeds

The biotransformation of the major Piper solmsianum leaf phenylpropanoids, such as the tetrahydrofuran lignan grandisin and derivatives was investigated in the beetle Naupactus bipes as well as in the caterpillars Heraclides hectorides and Quadrus u-lucida. Analysis of fecal material indicated that metabolism occurred mainly through mono- and di-O-demethylation at para positions of 3,4,5-trimethoxyphenyl rings of tetrahydrofuran lignans during digestion by these insects. Additionally, 3-hydroxy-4,5-dimethoxycinnamyl and 3,4,5-trimethoxycinnamyl alcohols were identified in fecal extracts of N. bipes.

Topics: Animals; Coleoptera; Furans; Lepidoptera; Lignans; Molecular Structure; Piper; Propanols