lignans and coniferin

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

To study the bioactive constituents of the fresh rhizome of Pinellia ternata, and provide the scientific basis for quality control.. Various chromatographic techniques were used to separate and purify the chemical constituents, and their chemical structures were determined on the basis of physical-chemical properties and spectroscopic analysis. The inhibitory effects of the isolated compounds on tumor necrosis factor (TNF)-alpha production in the peritoneal macrophages of mice stimulated with lipopolysaccharide (LPS) were assayed in vitro by microplate colorimetric method.. Nine compounds were isolated and identified as (E)-p-coumaryl alcohol (1), 3, 4-dihydroxycinnamyl alcohol (2), ferulic acid (3), lariciresinol (4), erythro-guaiacylglycerol-beta-O-4'-sinapyl ether (5), dehydrodiconiferyl alcohol (6) , isolariciresinol (7) , sachaliside 1 (8) and coniferin (9). The inhibitory effect of compounds 1, 2, 3, 8, and 9 were 24.1% , 57.6% , 40.2% , 82.7% , and 62.0% , respectively, against the TNF-alpha production in the peritoneal macrophages of mice stimulated with LPS at a concentration of 10(-5) mol L(-1) in vitro.. The compounds 1, 2 and 4-8 from genera Pinellia Ten. and compound 9 from P. ternata were isolated for the first time. The compounds 1, 2, 8 and 9 were phenylpropanoids, and 4-7 were lignanoids. The anti-inflammatory effects of the rhizome of P. ternata might relate at the least to compounds 1, 2, 3, 8 and 9.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Cells, Cultured; Cinnamates; Coumaric Acids; Furans; Lignans; Macrophages, Peritoneal; Male; Mice; Mice, Inbred C57BL; Molecular Structure; Pinellia; Plants, Medicinal; Rhizome; Tumor Necrosis Factor-alpha