Effect of molecular structure of phenolic families as hydroxycinnamic acids and catechins on their antioxidant effectiveness in minced fish muscle

The antioxidant effectiveness of two different families of phenolic compounds, hydroxycinnamic acids and catechins, added as a power (0.001% w/w) to chilled minced horse mackerel muscle was evaluated. Caffeic acid, chlorogenic acid, o-coumaric acid, and ferulic acid were selected as hydroxycinnamic acids with similar molecular structures. Commercial catechins with different numbers of hydroxylic groups, including catechin, gallocatechin, catechin gallate, and gallocatechin gallate, were also tested. The effectiveness found was individually discussed for each family as a function of the molecular structure. The capacity of hydroxycinnamic acids for donating electrons seems to play the most significant role for retarding the development of rancidity in fish muscle. Conversely, the properties related to the ability for chelating metals and the distribution between oily and aqueous phases were not correlated with the inhibitory activities. Among hydroxycinnamic acids, the results highlighted the potent antioxidant activity of 10 ppm caffeic acid in inhibiting lipid oxidation in fish muscle. Its antioxidant efficacy was similar to that of propyl gallate. Among catechins, catechin showed the highest antioxidant activity. There was an increment of efficacy in fish muscle using concentrations ranging between 10 and 100 ppm of both caffeic acid and catechin.     

Changes in color and odorant compounds during oxidative aging of Pedro Ximenez sweet wines

Pedro Ximenez sweet wines obtained following the typical criaderas and solera method for sherry wines and subjected to oxidative aging for 0, 1.3, 4.2, 7.0, or 11.5 years were studied in terms of color and aroma fraction by using the CIELab method and gas chromatography, respectively. The parameters defining the CIELab color space (a*, b*, and L*) were subjected to a multiple-range test (p<0.05) that allowed discrimination of the five wine aging levels studied into five uniform groups according to aging time. The aroma fraction was found to include 15 active odorant compounds with OAV > 1 that enriched the wines with fruity, fatty, floral, and balsamic notes during the aging process. The changes in color parameters and active odorants were not linearly related to aging time, being especially marked during the first 1.3 years and then less substantial up to the 7 years, the oldest wines exhibiting sensorial properties markedly departing from all others. For the wines aged over 1.3 years (minimum aging), 2,3-butanedione, linalool, and decanal can be used as reliable fingerprints of the older wines' quality.     

Main antimicrobial compounds in table olives

The inhibitors involved in the lactic acid fermentation of table olives were investigated in aseptic olive brines of the Manzanilla and Gordal varieties. Phenolic and oleosidic compounds in these brines were identified by high-performance liquid chromatography with ultraviolet and electrospray ionization mass spectrometry detection, and several substances were also characterized by nuclear magnetic resonance. Among these compounds, the dialdehydic form of decarboxymethyl elenolic acid linked to hydroxytyrosol showed the strongest antilactic acid bacteria activity, and its presence in brines could explain the growth inhibition of these microorganisms during olive fermentation. However, it was found that the dialdehydic form of decarboxymethyl elenolic acid, identified for the first time in table olives, and an isomer of oleoside 11-methyl ester were also effective against Lactobacillus pentosus and can, therefore, contribute to the antimicrobial activity of olive brines. It must also be stressed that the three new inhibitors discovered in table olive brines exerted a more potent antibacterial activity than the well-studied oleuropein and hydroxytyrosol.     

Partition behavior of virgin olive oil phenolic compounds in oil-brine mixtures during thermal processing for fish canning

The chemical modifications and partitioning toward the brine phase (5% salt) of major phenol compounds of extra virgin olive oil (EVOO) were studied in a model system formed by sealed cans filled with oil-brine mixtures (5:1, v/v) simulating canned-in-oil food systems. Filled cans were processed in an industrial plant using two sterilization conditions commonly used during fish canning. The partitioning of phenolic compounds toward brine induced by thermal processing was studied by reversed-phase high-performance liquid chromatographic analysis of the phenol fraction extracted from oils and brine. Hydroxytyrosol (1), tyrosol (2), and the complex phenolic compounds containing 1 and 2 (i.e., the dialdehydic form of decarboxymethyl oleuropein aglycon 3, the dialdehydic form of decarboxymethyl ligstroside aglycon 4, and the oleuropein aglycon 6) decreased in the oily phase after sterilization with a marked partitioning toward the brine phase. The increase of the total amount of 1 and 2 after processing, as well as the presence of elenolic acid 7 released in brine, revealed the hydrolysis of the ester bond of hydrolyzable phenolic compounds 3, 4, and 6 during thermal processing. Both phenomena (partitioning toward the water phase and hydrolysis) contribute to explain the loss of phenolic compounds exhibited by EVOO used as filling medium in canned foods, as well as the protection of n-3 polyunsaturated fatty acids in canned-in-EVOO fish products.     

Comparison of natural polyphenol antioxidants from extra virgin olive oil with synthetic antioxidants in tuna lipids during thermal oxidation

Polyphenols extracted from extra virgin olive oil (EVOO) were tested for their ability to inhibit lipid oxidation of canned tuna. Hydroperoxide formation during oxidation was monitored by measurement of peroxide value and decomposition of hydroperoxides by static headspace gas chromatographic analysis of volatiles. In tuna oxidized at 40 and 100 degrees C, 400 ppm of the EVOO polyphenols was an effective antioxidant as compared with 100 ppm of a 1:1 mixture of the synthetic antioxidants butylated hydroxytoluene and butylated hydroxyanisole. However, at concentrations <100 ppm, the EVOO phenolic compounds promoted hydroperoxide formation and decomposition. The EVOO polyphenols were effective antioxidants when added to heated tuna muscle in the presence of either brine or refined olive oil. The oxidation rate in tuna muscle packed in brine was higher than that of tuna packed in refined olive oil. The EVOO polyphenols had higher antioxidant activity in the brine samples than in the refined olive oil. The higher antioxidant activity of EVOO polyphenols in tuna packed in brine may be explained by their greater affinity toward the more polar interface between water and the fish oil system.     

Alternative method for the quantification by gas chromatography triacylglycerol class analysis of cocoa butter equivalent added to chocolate bars

Directive 2000/36/EC allows chocolate makers to add up to 5% of only six specific cocoa butter equivalents (CBEs) to cocoa butter (CB). A quantification method based on triacylglycerol (TAG) class analysis by gas chromatography with an unpolar column was set up for routine control purposes of chocolate bars. Mixtures of CBEs/CB were elaborated according to a Placket-Burman experiment design and analyzed by gas chromatography. A matrix was built with the normalized values of TAG classes (C50, C52, C54, and C56) of pure CBs of various origins, homemade CB/CBE mixtures (1 CB type), and mixtures containing CBE with CBs of various origins. A multivariate calibration equation was computed from this matrix using a partial least-squares regression technique. CBE addition can be detected at a minimum level of 2%, and the mathematical model allows its quantification with an uncertainty of 2% with respect to the cocoa butter fats. The model has also been applied for deconvolution and quantification of each CBE of a CBE mixture in chocolate bars.     

Aroma composition of Vitis vinifera Cv. tannat: the typical red wine from Uruguay

The free volatiles, as well as those released from the glycosidically bound forms by enzyme hydrolysis, have been analyzed to chracterize young Tannat wines from two successive vintages. The Tannat wine showed some aroma profile peculiarities detected in the free forms but, above all, in the bound fraction for the level and profile of the norisoprenoidic fraction. Among the free volatile compunds, a rather low content of C(6) alcohols with a prevalence of cis-3-hexen-1-ol on the trans form and sometimes a remarkable level of trans-2-hexen-1-ol seem to be typical for the variety. C(13)-norisoprenoidic and monoterpenic volatiles made up approximately 42% of the total level of the volatiles observed in the glycosidase enzyme-released fraction. The other volatiles were C(6) alcohols (6%) and benzenoid compounds (51%). The dominating monoterpene alcohols were the cis and trans isomers of 3,7-dimethyl-1,6-octadiene-3,8-diol (8-hydroxylinalool). The C(13)-norisoprenoid pattern was composed by 3-hydroxy-beta-damascone, 3-oxo-alpha-ionol, vomifoliol, 4-oxo-beta-ionol, 3-oxo-7,8-dihydro-alpha-ionol, 4-oxo-7,8-dihydro-beta-ionol, grasshopper ketone, and 7,8-dihydrovomifoliol.     

Genetic diversity among Northwestern Argentinian cultivars of common bean (Phaseolus vulgaris L.) as revealed by RAPD markers

The genetic diversity of 10 commercial cultivars of common beans, developed in Northern Argentina was analyzed based on RAPD markers. Sixteen primers were assayed and among them only 4 showed polymorphisms. A similarity matrix was generated by applying three different association coefficients, Simple Matching, Jaccard and Dice. By the UPGMA method dendrograms were generated and also the principal coordinate analysis was performed. The similarity values found were higher than 40% suggesting that genetic diversity is low. Both cluster analysis and principal coordinates analysis associated commercial cultivars either to the Andean or the Mesoamerican gene pool.     

Interaction of yeasts with the products resulting from the condensation reaction between (+)-catechin and acetaldehyde

The condensation reaction between (+)-catechin and acetaldehyde was studied in model solutions in the presence and absence yeasts in order to evaluate its contribution to color changes in fermented drinks such as white wine. On the basis of the results, the yeasts retain the oligomers produced in the reaction, their retention ability increasing for higher polymerization degrees. As a result, the color of model solutions, measured as the absorbance at 420 nm, was found to decrease after the addition of yeasts. On the other hand, the yeasts exhibited no inhibitory effect on the condensation reaction, which took place at the same rate in their presence and absence. At acidity levels and reactant concentrations similar to those in wine, with acetaldehyde in high concentration as it is present in sherry wines, the reaction was found to occur very slowly. Taking into account that Yeasts are present during most of the winemaking process; consequently, they retain oligomers, and the studied reaction could mainly contribute to the alteration of the color of white wine after bottling.