Structure determination of 3-O-caffeoyl-epi-gamma-quinide, an orphan bitter lactone in roasted coffee

Recent investigations on the bitterness of coffee as well as 5- O-caffeoyl quinic acid roasting mixtures indicated the existence of another, yet unknown, bitter lactone besides the previously identified bitter compounds 5- O-caffeoyl- muco-gamma-quinide, 3- O-caffeoyl-gamma-quinide, 4- O-caffeoyl- muco-gamma-quinide, 5- O-caffeoyl- epi-delta-quinide, and 4- O-caffeoyl-gamma-quinide. In the present study, this orphan bitter lactone was isolated from the reaction products generated by dry heating of 5- O-caffeoylquinic acid model, and its structure was determined as the previously unreported 3- O-caffeoyl- epi-gamma-quinide by means of liquid chromatography-mass spectrometry (LC-MS) and one-/two-dimensional NMR experiments. The occurrence of this bitter lactone, exhibiting a low bitter recognition threshold of 58 micromol/L, in coffee beverages could be confirmed by LC-MS/MS (negative electrospray ionization) operating in the multiple reaction monitoring mode.     

Antioxidant effectiveness of phenolic apple juice extracts and their gut fermentation products in the human colon carcinoma cell line caco-2

Apples represent a major dietary source of antioxidative polyphenols. Their metabolic conversion by the gut microflora might generate products that protect the intestine against oxidative damage. We studied the antioxidant effectiveness of supernatants of fermented apple juice extracts (F-AEs, 6 and 24 h fermentation) and of selected phenolic degradation products, identified by HPLC-DAD-ESI-MS. Cell free antioxidant capacity of unfermented apple juice extracts (AEs) was decreased after fermentation by 30-50%. In the human colon carcinoma cell line Caco-2, F-AEs (containing <0.5% of original AE-phenolics) decreased the reactive oxygen species (ROS) level more efficiently than the F-blank (fermented without AE) but were less effective than the respective AEs. Similarly, antioxidant effectiveness of individual degradation products was lower compared to respective AE constituents. Glutathione level was slightly increased and oxidative DNA damage slightly decreased by fermented AE03, rich in quercetin glycosides. In conclusion, F-AEs/degradation products exhibit antioxidant activity in colon cells but to a lesser extent than the respective unfermented AEs/constituents.     

Orosensory-directed identification of astringent mouthfeel and bitter-tasting compounds in red wine

Application of sequential solvent extraction, followed by HPLC combined with the taste dilution analysis, enabled the localization of the most intense velvety astringent, drying, and puckering astringent, as well as bitter-tasting, compounds in red wine, respectively. Isolation of the taste components involving gel adsorption chromatography, ultrafiltration, and synthesis revealed the identification of 26 sensory-active nonvolatiles, among which several hydroxybenzoic acids, hydroxycinnamic acids, flavon-3-ol glycosides, and dihydroflavon-3-ol rhamnosides as well as a structurally undefined polymeric fraction (>5 kDa) were identified as the key astringent components. In contradiction to literature suggestions, flavan-3-ols were found to be not of major importance for astringency and bitter taste, respectively. Surprisingly, a series of hydroxybenzoic acid ethyl esters and hydroxycinnamic acid ethyl esters were identified as bitter compounds in wine. Taste qualities and taste threshold concentrations of the individual wine components were determined by means of a three-alternative forced-choice test and the half-mouth test, respectively.     

Molecular and sensory studies on the umami taste of Japanese green tea

Aimed at defining the key drivers for the quality-determining umami taste of a high-grade powdered green tea, called mat-cha, a bioactivity-guided fractionation using solvent extraction, solvent precipitation, preparative chromatographic separations, and human psychophysical experiments was applied on freshly prepared mat-cha. Liquid chromatography-tandem mass spectrometry and one-/two-dimensional nuclear magnetic resonance studies on isolated fractions led to the identification of l-theanine, succinic acid, 3,4,5-trihydroxybenzoic acid (gallic acid), and (1R,2R,3R,5S)-5-carboxy-2,3,5-trihydroxycyclohexyl-3,4,5-trihydroxybenzoate (theogallin) as umami-enhancing compounds in the green tea beverage, and it can be shown by sensory studies that these compounds are able to raise the umami intensity of sodium l-glutamate proportionally.     

Influence of food quality and quantity on the growth and development of Crassostrea gigas larvae: a modeling approach

A biochemically based model was developed to simulate the growth, development and metamorphosis of larvae of the Pacific oyster, Crassostrea gigas. The model is unique in that it (1) defines larvae in terms of their protein, neutral lipid, polar lipid, carbohydrate and ash content; (2) tracks weight separately from length to follow larval condition index and (3) includes genetic variation in growth efficiency and egg quality to better simulate cohort population dynamics. The model includes parameterizations for larval filtration, ingestion and respiration that determine growth rate and processes controlling larval mortality and metamorphosis. Changes in tissue composition occur as the larva grows and in response to the biochemical composition of the food.

The simulations show that genetically determined variations in growth efficiency produce significant changes in larval survival and success at metamorphosis. Larvae with low growth efficiency are successful under a much narrower range of culture conditions than larvae with high growth efficiency. The impact of low growth efficiency is primarily controlled by the ability of larvae to store lipid for metamorphosis. Culture conditions that provide increased dietary lipid counterweigh low growth efficiency. Changes in food quantity and quality had little effect on size at metamorphosis. On the other hand, larval life span and success rate at metamorphosis varied over a wide range depending upon the conditions of the simulation. Food quality and food availability both influence larval life span and, hence, larval survival. As ingestion rate decreases, larval life span increases and cohort survival declines. Increased lipid or decreased protein in the diet improves cohort survival. Changes in carbohydrate content are less influential. If cohort success is significantly affected by mortality during larval life rather than success at metamorphosis, the influence of food quality becomes more complex. The range of food compositions yielding high survival is restricted by a balance between improved success at metamorphosis obtained by increased lipid storage and the shortening of larval life span as a result of more rapid growth, a function of protein availability. These simulations illustrate the strength and utility of numerical models for evaluating and designing hatchery protocols for optimizing yield of C. gigas larvae.     

Pesticide contamination of the upper Elbe River and an adjacent floodplain area

Journal of Soils and Sediments - Pesticide contamination of river waters is a global problem, and therefore, authorities regularly monitor the water quality status. Especially, flood events might...     

Eine Waldstation für Tannenlausstudien

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