Updated knowledge about the presence of phenolic compounds in wine

Phenolic compounds are partly responsible for the color, astringency, and bitterness of wine, as well as for numerous physiological properties associated with wine consumption. Mass spectrometry has allowed for great progress in the identification and characterization of wine polyphenols. The aim of the present article is to summarize the numerous advances recently achieved in this field. The main type of phenolic compounds found in wine, including hydroxybenzoic and hydroxycinnamic acids, stilbenes, flavones, flavonols, flavanonols, flavanols, and anthocyanins, are firstly described. Chemical reactions and mechanisms involving phenolic compounds during winemaking are also extensively discussed, including enzymatic and chemical oxidation reactions, direct and acetaldehyde-mediated anthocyanin-tannin condensation reactions, acetaldehydemediated and glyoxylic acid-mediated tannin-tannin condensation reactions and, C-4/C-5 anthocyanin cycloaddition reactions with 4-vinylphenols, vinylflavanols and pyruvic acid, among others, leading to the formation of pyranoanthocyanins. Useful mass spectral data of well-known and novel phenolic compounds recently identified in wine, and details related to their fragmentation pathway according to different ionization techniques, are given.     

Evaluation of SPE as Preparative Technique for the Analysis of Phenolic Metabolites in Human Feces

Solid phase extraction (SPE) methodology has been evaluated as a cleanup strategy prior to the analysis of phenolic metabolites in fecal samples by UPLC–DAD–ESI–TQ MS. Among the sorbents tested, Oasis® HLB led to the higher phenolic standard recoveries. Sample acidification (0.4 M HCl, final concentration) before SPE considerably improved standard recoveries. Values of the process efficiency (C_SPE/C_{Without SPE}) for a standard solution containing gallic acid, protocatechuic acid, caffeic acid, benzoic acid, 3-phenylpropionic acid, (+)-catechin, (?)-epicatechin, procyanidin B2, and 4-hydroxybenzoic 2,3,5,6 d₄ acid were acceptable (>90 %) for all compounds, except for procyanidin B2 (26 %). The developed SPE methodology was applied to fecal samples of individuals subjected to a wine intervention study. Phenolic metabolites, including intermediate metabolites (phenyl-γ-valerolactones and phenylvaleric acid derivatives) and end products (simple phenols, hydroxyphenylpropionic, hydroxyphenylacetic, hydroxycinnamic, and hydroxybenzoic acids) were identified. Most of the compounds (n?=?14) exhibited values of process efficiency between 85 and 115 %. Although some compounds (n?=?4) showed process efficiency>115 %, there was a group of metabolites (4-O-methylgallic acid, syringic acid, and 4-hydroxy-5-(3′,4′-dihydroxyphenyl)-valeric acid) whose process efficiency was <85 %, which represented a serious limitation and made us to discard SPE as a preparative technique for the analysis of these phenolic metabolites. Finally, the paper reports the concentrations of phenolic metabolites in a randomized set of human fecal samples from healthy volunteers (n?=?15) without any previous SPE application. Large inter-individual variability was observed, which was attributed to differences in human gut microbiota composition.     

Investigation of the in vivo antioxidative activity of Cynara scolymus (artichoke) leaf extract in the streptozotocin‐induced diabetic rat

The in vivo antioxidant activity of a quantified leaf extract of Cynara scolymus (artichoke) was studied. The aqueous artichoke leaf extract (ALE), containing 1.5% caffeoylquinic acid with chlorogenic acid being most abundant (0.30%), and luteolin‐7‐O‐glucoside as major flavonoid (0.15%), was investigated by evaluating the effect on different oxidative stress biomarkers, after 3 wk oral supplementation in the streptozotocin‐induced diabetic rat model. Apart from two test groups (0.2 g ALE/kg BW/day and 1 g ALE/kg BW/day, where BW is body weight), a healthy control group, untreated oxidative stress group, and vitamin E treated group (positive control) were included. A 0.2 g/kg BW/day of ALE decreased oxidative stress: malondialdehyde and 8‐hydroxydeoxyguanosine levels significantly diminished, whereas erythrocyte glutathione levels significantly increased. A 1.0 g/kg BW/day ALE did not show higher antioxidant activity.     

Nutritional and health-related compounds in sprouts and seeds of soybean (<Emphasis Type="Italic">Glycine max</Emphasis>), wheat (<Emphasis Type="Italic">Triticum aestivum.L</Emphasis>) and alfalfa (<Emphasis Type="Italic">Medicago sativa</Emphasis>) treated by a new drying method

Nutritional and health-related compounds of alfalfa, wheat and soybean seeds dried by new drying process called the DIC process (controlled instantaneous pressure release) were evaluated, before and after sprouting. Vitamins (A, B₁, B₂, B₆, C and E), minerals (Fe, Mg, Ca, K, Mn, Na, Cu and Zn) and phytoestrogens (genistein and daidzein ) content were determined. Alfalfa, soybean and wheat seeds dried by DIC showed similar content of biological compounds to seeds dried by traditional processes. Sprouting DIC-seeds significantly increased the levels of vitamins, minerals and phytoestrogens, improving their nutrititional value and health quality compared to fresh products. The increase of 1250-fold and 10-fold of the initial vitamin A and vitamin C content, respectively, of alfalfa seeds due to sprouting is remarkable. Sprouts from DIC-seeds showed a significantly higher vitamin A content than sprouts obtained from seeds dried by other methods. Soybean sprouts obtained from DIC-seeds showed a significant increase in free phytoestrogens, quantified as genistein (70.34LJ.8 mg kg^-1 d.w.) and daidzein (109.17.3ᆥ.3 mg kg^-1 d.w.).     

Differentiation of intermediate products (concentrates and purées) from the fruit industry by means of phenolic content

Concentrates and purées are intermediate products in the manufacture of commercial fruit juices. In this paper, the phenolic content [total polyphenols (TP), ortho-diphenols (ORT) and catechins (CAT)] in a large number of concentrates and purées from apple and peach fruits has been determined. The relationships TP/ORT, TP/CAT and ORT/CAT have also been calculated. TP content was found to be significantly higher in the concentrates than in the respective purées whereas CAT content was significantly higher in the purée. ORT was found to be higher in purées than in apple concentrates, but the opposite was observed for peaches. The relationships TP/ORT, TP/CAT and ORT/CAT were higher for the concentrates than for the respective purées. In addition, values for ORT/CAT were higher for the peach products than for the respective apple products. The results show that these phenolic compound measurements enable differentiation between concentrates and purées, as well as between the fruit juices produced from them. The main advantage of measurements of total phenolic compounds is that they are easy to perform in a conventional laboratory, which makes them suitable for routine analysis.     

A Novel Functional Wrapping Design by Complexation of ε-Polylysine with Liposomes Entrapping Bioactive Peptides

An innovative edible wrapping with potential use for designing functional foods with antimicrobial capacity was developed by complexation of ε-polylysine with peptide-loaded liposomes. Unmarketable long-term frozen cooked shrimp (Litopenaeus vannamei) muscle was used as a source of both bioactive peptides and complex liposomal suspension carrier, producing a sustainable value-added protein wrapping material with desirable sensory properties. A <10-kDa peptide fraction (SH) with antioxidant and angiotensin-converting enzyme inhibitory capacity was encapsulated in partially purified phosphatidylcholine (PC) liposomes (LSH) with an entrapment efficiency of 85 %. The average size and zeta potential of LSH were 164?±?2 nm and –37.0?±?1.7 mV, respectively. The LSH surface changed from electronegative to electropositive upon adsorption of ε-polylysine (PL) with an optimal concentration of 0.5 %. The average diameter and zeta potential of the resulting complex ε-polylysine-adsorbed liposomes containing the peptide hydrolysate (PL-LSH) were 216?±?5 nm and +51.1?±?1.1 mV, respectively. The ε-PL proved to be effective as liposome stabilizing and antimicrobial agent. The PL-LSH suspension was incorporated in the formulation of the protein wrapping to provide it with both bioactive and antimicrobial properties. The wrapping showed low water solubility (≈30 %) and low mechanical resistance (tensile strength?=?0.23?±?0.06 MPa; elongation at break?=?0.91?±?0.19 %) properties that allowed it to be very versatile for varied food design and was effective against Listeria monocytogenes, Escherichia coli, Staphylococcus aureus and Yersinia enterocolitica.     

Improvement of frozen banana (Musa cavendishii, cv. Enana) colour by blanching: relationship between browning, phenols and polyphenol oxidase and peroxidase activities

 Browning in banana (Musa cavendishii, cv. Enana) processed products is a result of phenol oxidation catalysed by polyphenol oxidase (PPO) and peroxidase (POD) or of other non-enzymatic reactions (Maillard and Strecker mechanisms). Microwave and steam blanching significantly reduced PPO and POD activities and phenol levels in banana flesh, steam blanching being the most effective method for enzyme inactivation. Freezing/thawing processes produced a significant increase in phenol levels in all samples, due to cellular breakdown. After microwave heating browning processes occurred while steam-treated samples did not exhibit a significant colour change. Extractable PPO and POD activities in all banana samples increased as a consequence of freezing/thawing: steam-blanched slices exhibited lower residual activities. High correlations occurred between phenols and browning (r=0.86) in control samples. Blanched samples (microwave or steam) only exhibited correlations between PPO (r=0.80) and POD (r=0.80) activities and browning. Received: 22 February 1996     

Improvement of frozen banana (Musa cavendishii, cv. Enana) colour by blanching: relationship between browning, phenols and polyphenol oxidase and peroxidase activities

 Browning in banana (Musa cavendishii, cv. Enana) processed products is a result of phenol oxidation catalysed by polyphenol oxidase (PPO) and peroxidase (POD) or of other non-enzymatic reactions (Maillard and Strecker mechanisms). Microwave and steam blanching significantly reduced PPO and POD activities and phenol levels in banana flesh, steam blanching being the most effective method for enzyme inactivation. Freezing/thawing processes produced a significant increase in phenol levels in all samples, due to cellular breakdown. After microwave heating browning processes occurred while steam-treated samples did not exhibit a significant colour change. Extractable PPO and POD activities in all banana samples increased as a consequence of freezing/thawing: steam-blanched slices exhibited lower residual activities. High correlations occurred between phenols and browning (r=0.86) in control samples. Blanched samples (microwave or steam) only exhibited correlations between PPO (r=0.80) and POD (r=0.80) activities and browning. Received: 22 February 1996