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Effect of gelatin (a model for salivary PRP) on the sensory astringency of 5-O-caffeoylquinic acid and tannic acid.

The present work investigates differences (triangular tests) between the astringency of 5-O-caffeoylquinic acid (5-CQA) and that of 5-CQA + gelatin. As an overall reference similar tests are reported using tannic acid (which has been shown to elicit a strong response). Finally, a time-intensity study on aqueous solutions of tannic acid (TA), TA + gelatin and gelatin, reveals relevant temporal factors. Although, under the experimental conditions, the majority of comparisons revealed statistically significant differences, in the time-intensity study no significant differences were found between TA + gelatin and gelatin, either for the intensity or the total duration of the response. Moreover, for the fading of the response there was no difference between TA + gelatin and TA. The main temporal contribution to the difference is in the onset of the response and can be related to the spectral differences observed in the earlier studies. It will be argued that these results may represent an important step in our understanding of the mechanisms of astringency.

Chlorogenic Acid↗

Inhibitory effects of anthocyanins and other phenolic compounds on nitric oxide production in LPS/IFN-gamma-activated RAW 264.7 macrophages.

Flavonoids have been reported to lower oxidative stress and possess beneficial effects on cardiovascular diseases and chronic inflammatory diseases associated with nitric oxide (NO). Common phenolic compounds, including phenolic acids, flavonols, isoflavones, and anthocyanins, present in fruits were investigated for their effects on NO production in LPS/IFN-gamma-activated RAW 264.7 macrophages. Phenolic compounds at the range of 16-500 microM that inhibited NO production by > 50% without showing cytotoxicity were the flavonols quercetin and myricetin, the isoflavone daidzein, and the anthocyanins/anthocyanidins pelargonidin, cyanidin, delphinidin, peonidin, malvidin, malvidin 3-glucoside, and malvidin 3,5-diglucosides. Anthocyanins had strong inhibitory effects on NO production. Anthocyanin-rich crude extracts and concentrates of selected berries were also assayed, and their inhibitory effects on NO production were significantly correlated with total phenolic and anthocyanin contents. This is the first study to report the inhibitory effects of anthocyanins and berry phenolic compounds on NO production.

Animals↗

Neuroprotective effects of 3,5-dicaffeoylquinic acid on hydrogen peroxide-induced cell death in SH-SY5Y cells.

Oxidative stress plays an important role in the pathological processes of a variety of neurodegenerative diseases. The neuroprotective effects of 3,5-diCQA and 3,4-diCQA, two caffeoylquinic acid derivatives present in Dipsacus asper, on hydrogen peroxide (H2O2)-induced neuronal cell damage were evaluated in this study.SH-SY5Y cells treated with H2O2 exhibited a decrease in survival and intracellular glutathione and also an increase in the caspase-3 activity. However, pretreatment of cells with 3,5-diCQA attenuated the neuronal death and caspase-3 activation induced by H2O2. In addition, 3,5-diCQA restored H2O2-induced depletion of intracellular glutathione. 3,5-diCQA showed significant protective effects although it could not completely suppress H2O2-induced cell injury to control levels. The data suggest that 3,5-diCQA might be a potential therapeutic agent for treating or preventing neurodegenerative diseases implicated with oxidative stress.

Caspase 3↗

Downregulation of a pathogen-responsive tobacco UDP-Glc:phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance.

Plant UDP-Glc:phenylpropanoid glucosyltransferases (UGTs) catalyze the transfer of Glc from UDP-Glc to numerous substrates and regulate the activity of compounds that play important roles in plant defense against pathogens. We previously characterized two tobacco salicylic acid- and pathogen-inducible UGTs (TOGTs) that act very efficiently on the hydroxycoumarin scopoletin and on hydroxycinnamic acids. To identify the physiological roles of these UGTs in plant defense, we generated TOGT-depleted tobacco plants by antisense expression. After inoculation with Tobacco mosaic virus (TMV), TOGT-inhibited plants exhibited a significant decrease in the glucoside form of scopoletin (scopolin) and a decrease in scopoletin UGT activity. Unexpectedly, free scopoletin levels also were reduced in TOGT antisense lines. Scopolin and scopoletin reduction in TOGT-depleted lines resulted in a strong decrease of the blue fluorescence in cells surrounding TMV lesions and was associated with weakened resistance to infection with TMV. Consistent with the proposed role of scopoletin as a reactive oxygen intermediate (ROI) scavenger, TMV also triggered a more sustained ROI accumulation in TOGT-downregulated lines. Our results demonstrate the involvement of TOGT in scopoletin glucosylation in planta and provide evidence of the crucial role of a UGT in plant defense responses. We propose that TOGT-mediated glucosylation is required for scopoletin accumulation in cells surrounding TMV lesions, where this compound could both exert a direct antiviral effect and participate in ROI buffering.

Chlorogenic Acid↗

Interactions of glycinin with plant phenols--influence on chemical properties and proteolytic degradation of the proteins.

Soya glycinin was derivatized with different phenolic substances (caffeic-, chlorogenic-, gallic acid and quercetin). The protein derivatives formed have been characterized in terms of their properties where they showed changes in the content of free epsilon-amino groups, tryptophan and thiol groups. The derivatives have also been characterized in terms of their solubility at different pH-values to document the influence on the functional properties. Another objective of this paper was to demonstrate the influence on the digestibility of the proteins with one of the main enzymes of the gastro-intestinal tract (pancreatin) on the basis of in vitro experiments after derivatization with phenolic substances. The enzymatic digestion of the derivatized proteins was promoted.

Digestion↗

Neuroprotective effect of H. perforatum extracts on beta-amyloid-induced neurotoxicity.

In the present study we assessed the neuroprotective role of a Hypericum perforatum ethanolic extract and obtained fractions in amyloid-beta peptide (Abeta)((25-35))-induced cell death in rat cultured hippocampal neurons. Lipid peroxidation was used as a marker of oxidative stress by following the formation of TBARS in rat cortical synaptosomes, after incubation with ascorbate/Fe2+, alone or in the presence of EC97 effective concentrations of H. perforatum fractions. Induced lipid peroxidation was significantly inhibited by fractions containing flavonol glycosides, flavonol and biflavone aglycones, and by a fraction containing several phenols, mainly chlorogenic acid-type phenolics (21%, 77% and 98%, respectively). Lipid peroxidation evaluated after incubation with 25 microM Abeta(25-35), was significantly inhibited by H. perforatum extract. Cell viability was assessed by use of the Syto-13/PI assay. The total ethanolic extract (TE) and fractions containing flavonol glycosides, flavonol and biflavone aglycones, reduced Abeta(25-35)-induced cell death (65%, 58% and 59%, respectively). These results were further supported by morphological analysis of cells stained with cresyl violet. Peptide beta-amyloid(25-35) induced a decrease in cell volume, chromatin condensation and nuclear fragmentation, alterations not evident in the presence of the TE and fractions containing hypericins (hypericin concentration = 11.02 microM), or fractions containing flavonoids (quercetin concentration = 21.13 microM). Dendritic lesion, an evidence of neurodegeneration, was observed by neuronal staining with cobalt following insult with Abeta(25-35), but prevented after exposure to the peptide plus the fractions referred above. The results of the present paper suggest that H. perforatum extracts may be endowed with neuroprotective compounds able to prevent Abeta(25-35)-induced toxicity.

Amyloid beta-Peptides↗

Overexpression of polyphenol oxidase in transgenic tomato plants results in enhanced bacterial disease resistance.

Polyphenol oxidases (PPOs; EC 1.10.3.2 or EC 1.14.18.1) catalyzing the oxygen-dependent oxidation of phenols to quinones are ubiquitous among angiosperms and assumed to be involved in plant defense against pests and pathogens. In order to investigate the role of PPO in plant disease resistance, we made transgenic tomato ( Lycopersicon esculentum Mill. cv. Money Maker) plants that overexpressed a potato ( Solanum tuberosum L.) PPO cDNA under control of the cauliflower mosaic virus 35S promoter. The transgenic plants expressed up to 30-fold increases in PPO transcripts and 5- to 10-fold increases in PPO activity and immunodetectable PPO. As expected, these PPO-overexpressing transgenic plants oxidized the endogenous phenolic substrate pool at a higher rate than control plants. Three independent transgenic lines were selected to assess their interaction with the bacterial pathogen Pseudomonas syringae pv. tomato. The PPO-overexpressing tomato plants exhibited a great increase in resistance to P. syringae. Compared with control plants, these transgenic lines showed less severity of disease symptoms, with over 15-fold fewer lesions, and strong inhibition of bacterial growth, with over 100-fold reduction of bacterial population in the infected leaves. These results demonstrate the importance of PPO-mediated phenolic oxidation in restricting plant disease development.

Catechol Oxidase↗

Foliar phenolics in sugar maple (Acer saccharum) as a potential indicator of tropospheric ozone pollution.

Tropospheric O3 has been implicated in the declining health of forest ecosystems in Europe and North America and has been shown to have negative consequences on human health. We have measured tropospheric ozone (O3) in the lower canopy through the use of passive monitors located in five woodlots along a 150 km urban-rural transect, originating in the large urban complex of Toronto, Canada. We also sampled foliage from 10 mature sugar maple trees in each woodlot and measured the concentration of a number of phenolic compounds and macronutrients. O3 concentrations were highest in the two rural woodlots, located approximately 150 km downwind of Toronto, when compared to the woodlots found within the Greater Toronto Area. Foliar concentrations of three flavonoids, avicularin, isoquercitrin, and quercitrin, were significantly greater and nitrogen concentrations significantly lower at these same rural woodlots, suggesting some physiological disruption is occurring in those sites where exposure to tropospheric O3 is greater. We suggest that foliar phenolics of sugar maple may be a biochemical indicator of tropospheric ozone exposure.

Acer↗