Solid-state bioconversion of phenolics from cranberry pomace and role of Lentinus edodes beta-glucosidase

Cranberry pomace contains large amounts of phenolic glycosides, which are important sources of free phenolics that have many food uses such as antioxidants, flavorings, and nutraceuticals. Our hypothesis was that these glycosides in cranberry pomace could be hydrolyzed by beta-glucosidase produced by Lentinus edodes during solid-state fermentation. On the basis of this hypothesis, our objective was to investigate the potential of using cranberry pomace as a substrate for the production of free phenolics and beta-glucosidase through solid-state fermentation by a food-grade fungus L. edodes. Our results suggested that L. edodes beta-glucosidase played a major role in release of phenolic aglycons from cranberry pomace during solid-state fermentation. After 50 days of cultivation, the yield of total free phenolics reached the maximum of 0.5 mg per g of pomace, while the beta-glucosidase activity was about 9 units per g of pomace. The enzyme exhibited optimal activity at 60 degrees C and at pH 3.5 and was stable at temperatures up to 50 degrees C and between pH 3 and 6.5. The major free phenolics produced from cranberry pomace were identified by HPLC as gallic acid, chlorogenic acid, p-hydroxybenzoic acid, and p-coumaric acid. These results suggest that cranberry pomace is a potential substrate for producing food-grade phenolics and fungal beta-glucosidase. The L. edodes beta-glucosidase showed good stability and tolerance to low pH and, therefore has potential applications in wine and juice processing for aroma and flavor enrichment through enzymatic hydrolysis of glucoside precursors.     

霞多丽干白葡萄酒品种香和发酵香成分变化的比较研究

本研究对确立宁夏贺兰山东麓原产地葡萄酒质量的感官体系标准,以及对葡萄酒生产工艺优化和质量评价有着重要实用价值。采用溶液萃取法提取霞多丽品种果实与干白发酵香气成分,用气相色谱-质谱进行分离测定,结合计算机检索技术对分离化合物进行鉴定,应用色谱峰面积归一法测定各成分的相对含量。实验结果：果实和干白葡萄酒中分别分离出81和33个峰,鉴定出78和32个香气化学成分,共占其色谱流出组分总量的98.89%和98.97%;成熟果实的挥发性物质,主要是2-呋喃甲醛等脂肪醛、2-呋喃乙酮等脂肪酮和十六碳酸等脂肪羧酸类。经过发酵工艺处理原酒中挥发性物质,主要有3-甲基丁醇、丁二酸二乙酯、辛酸、苯乙醇等。相对含量较高的香气成分种类相似,而微量特征香气成分差异较为显著,从而构成不同产区同一品种葡萄酒相似和独特香气与风格。本结果将对不同原产区优质葡萄酒酿造工艺生产,最大限度的释放游离态芳香物质的能力,提高干白葡萄酒的果香,有重要指导意义。     

Application of high-temperature gas chromatography-mass spectrometry to the investigation of glycosidically bound components related to cashew apple (Anacardium occidentale L. Var. Nanum) volatiles

Free and bound volatile components of a Brazilian cashew apple variety (Anacardium occidentale L. var. nanum) were obtained by simultaneous distillation-extraction (SDE) and XAD-2 adsorption. According to gas chromatography-mass spectrometry (GC-MS) analyses and retention indices, 62 free volatile constituents were characterized and quantified. They were esters (40%), terpenes (20%), hydrocarbons (14%), fatty acids (9%), aldehydes (8%), alcohols (3%), lactones (3%), ketones (1%), phenols (1%), and norisoprenoids (1%). The glycosidically bound volatile precursors were analyzed by high-temperature GC-MS, after room temperature silylation. Several conjugated alcohols and cinnamic acids were detected and reported as cashew apple glycosyl constituents for the first time.     

Effect of flash release treatment on phenolic extraction and wine composition

The flash release (FR) process, consisting of rapidly heating the grapes and then applying strong vacuum, has been proposed to increase the polyphenol content of red wines. Its impact on polyphenol extraction kinetics and on the polyphenol composition of red juice and wines was studied over two seasons on different grape varieties (Grenache, Mourvedre, Carignan). The FR process allows fast extraction of all phenolic compounds (hydroxycinnamic acids, flavonols, anthocyanins, catechins, proanthocyanidins) and can be used to produce polyphenol-enriched grape juices. However, the concentration of all polyphenols dramatically decreased throughout fermentation when pressing was achieved immediately after FR. The FR wines made with pomace maceration were also enriched in polyphenols compared to the corresponding control wines. Increasing the duration of high-temperature exposure in the FR treatment further increased extraction of phenolic compounds but also accelerated their conversion to derived species. The tannin-to-anthocyanin ratio was particularly low in the wine fermented in the liquid phase, higher after FR than in the control, and even higher after longer heating. FR resulted in an increased tannin-to-anthocyanin ratio and an increased conversion of anthocyanins to tannin-anthocyanin adducts showing the same color properties as anthocyanins. The tannin-to-anthocyanin ratio was particularly low in the wine fermented in the liquid phase that also contained larger amounts of orange sulfite bleaching-resistant pigments.     

Champagne wine polyphenols protect primary cortical neurons against peroxynitrite-induced injury

White wines are generally low in polyphenol content as compared to red wines. However, Champagne wines have been shown to contain relatively high amounts of phenolic acids that may exert protective cellular actions in vivo. In this study, we have investigated the potential neuroprotective effects of Champagne wine extracts, and individual phenolics present in these extracts, against peroxynitrite-induced injury. Organic and aqueous Champagne wine extracts exhibited potent neuroprotective activity against peroxynitrite-induced injury at low concentrations (0.1 microg/mL). This protection appeared to be in part due to the cellular actions of individual components found in the organic extracts, notably tyrosol, caffeic acid, and gallic acid. These phenolics were observed to exert potent neuroprotection at concentrations between 0.1 and 10 microM. Together, these data suggest that polyphenols present in Champagne wine may induce a neuroprotective effect against oxidative neuronal injury.     

Antioxidant capacities and phenolics levels of French wines from different varieties and vintages.

Phenolics from grapes and wines can play a role against oxidation and development of atherosclerosis. Levels of phenolics, major catechins [(+)-catechin, (-)-epicatechin, procyanidin dimers B1, B2, B3, and B4], phenolic acids (gallic acid and caffeic acid), caftaric acid, malvidin-3-glucoside, peonidin-3-glucoside, and cyanidin-3-glucoside were quantified by HPLC with UV detection for 54 French varietal commercial wines taken from southern France to study the antioxidant capacity and the daily dietary intake of these compounds for the French population. The highest antioxidant capacity was obtained with red wines and ranged from 12.8 mmol/L (Grenache) to 25.2 mmol/L (Pinot Noir). For white wines, Chardonnay enriched in phenolics by special wine-making was found to have an antioxidant capacity of 13.8 mmol/L, comparable to red wine values. For red wines classified by vintages (1996-1999) antioxidant capacities were approximately 20 mmol/L and then decreased to 13.4 mmol/L for vintages 1995-1991. Sweet white wines have 1.7 times more antioxidant capacity (3.2 mmol/L) than dry white wines (1.91 mmol/L). On the basis of a still significant French wine consumption of 180 mL/day/person, the current daily intake of catechins (monomers and dimers B1, B2, B3, and B4) averaged 5 (dry white wine), 4.36 (sweet white wines), 7.70 (rosé wines), 31.98 (red wines), and 66.94 (dry white wine enriched in phenolic) mg/day/resident for the French population. Red wine, and particularly Pinot Noir, Egiodola, Syrah, Cabernet Sauvignon, and Merlot varieties, or Chardonnay enriched in phenolics during wine-making for white varieties contribute to a very significant catechin dietary intake.     

Influence of aging conditions on the quality of red Sangiovese wine

A red Sangiovese wine was stored in barrels of different woods (oak and chestnut) and types (225-L "barriques" and 1000-L barrels) at 12 and 22 degrees C for 320 days to evaluate the effects of different aging conditions on wine quality. Chestnut barrels led to wines richer in phenolics, and which were more tannic, colored, and fruity. Oak barrels gave wines with more monomeric phenolics, but less astringent, with higher vanilla smell, and more harmonious. The type of barrel could be used as a parameter to regulate the extraction of wood components and the polymerization of monomeric phenolics. Storage at 22 degrees C favored the formation of polymerized phenolics and the increase of color density and color hue. The temperature produced less pronounced effects on aroma and taste, even if wines stored at 12 degrees C showed more harmony.     

Effect of flash release and pectinolytic enzyme treatments on wine polysaccharide composition

Various treatments, including flash release and addition of pectic enzymes, have been proposed to enhance degradation of grape berry cell walls and extraction of aroma and phenolic compounds into the wines. The effect of flash release and enzyme treatment used separately or in combination on wine polysaccharide composition was studied. The flash release process increased extraction of polysaccharides originating from grape berry cell walls, that is, polysaccharides rich in arabinose and galactose (PRAGs) and type II rhamnogalacturonan (RG-II), thus yielding enriched wines. Increasing the duration of high-temperature exposure before the flash release treatment further increased extraction of polysaccharides. However, the wine obtained by pressing immediately after flash release and fermenting in the liquid phase contained lower amounts of grape polysaccharides, indicating that their extraction required skin maceration. The use of enzymes without or with flash release modified the composition and the structure of pectic polysaccharides. In particular, it induced the loss of PRAG terminal arabinose residues.     

A powerful aromatic volatile thiol, 2-furanmethanethiol, exhibiting roast coffee aroma in wines made from several Vitis vinifera grape varieties

The chemical compound 2-furanmethanethiol (2FM), with a strong roast coffee aroma, has been identified in sweet white wines made from the Petit manseng grape variety, and in certain red Bordeaux wines (made from the Merlot, Cabernet franc, and Cabernet sauvignon grape varieties). This was done by extracting specific volatile thiols using p-hydroxymercuribenzoate. The 2FM has also been found in toasted oak used in barrel-making. All the Petit manseng sweet white wines and some of the red Bordeaux wines analyzed contained between a few ng/L and several dozen ng/L of 2FM. Taking into account its very low perception threshold (0.4 ng/L in a model hydro alcoholic environment), 2FM could therefore contribute to the roast coffee aroma of certain wines.     

Phenolic acids in wheat varieties in the HEALTHGRAIN Diversity Screen

The amounts and compositions of free, conjugated, bound, and total phenolic acids were determined in 175 samples of wheat flour grown on a single site in 2005. The highest contents of total phenolic acids were found in flours of winter wheat (1171 microg/g) with average levels of 658 microg/g total phenolics across all of the wheat genotypes. Winter wheats showed a range of >3.5-fold across the concentration range for total phenolic acids. Spelt genotypes displayed the narrowest (1.9-fold) range of total phenolic acid concentration. The concentrations of phenolic acids in the different phenolic acid fractions were in the order bound > conjugated > free, with bound phenolic acids making up around 77% of the total phenolic acid concentration and free phenolic acids constituting between 0.5 and 1%. The results indicate that there is genetic diversity in phenolic acid content and that it should be possible to selectively breed for lines with high contents of phenolic components.     

Identification and quantification of antioxidant components of honeys from various floral sources

Little is known about the individual components of honey that are responsible for its antioxidant activity. The present study was carried out to characterize the phenolics and other antioxidants present in honeys from seven floral sources. Chromatograms of the phenolic nonpolar fraction of the honeys indicated that most honeys have similar but quantitatively different phenolic profiles. Many of the flavonoids and phenolic acids identified have been previously described as potent antioxidants. A linear correlation between phenolic content and ORAC activity was demonstrated (R(2) = 0.963, p < 0.0001). Honeys were separated by solid-phase extraction into four fractions for sugar removal and separation based on solubility to identify the relative contribution of each fraction to the antioxidant activity of honey. Antioxidant analysis of the different honey fractions suggested that the water-soluble fraction contained most of the antioxidant components. Specific water-soluble antioxidant components were quantified, including protein; gluconic acid; ascorbic acid; hydroxymethylfuraldehyde; and the combined activities of the enzymes glucose oxidase, catalase and peroxidase. Of these components, a significant correlation could be established only between protein content and ORAC activity (R(2) = 0.674, p = 0.024). In general, the antioxidant capacity of honey appeared to be a result of the combined activity of a wide range of compounds including phenolics, peptides, organic acids, enzymes, Maillard reaction products, and possibly other minor components. The phenolic compounds contributed significantly to the antioxidant capacity of honey but were not solely responsible for it.     

Study of the formation mechanisms of some volatile compounds during the aging of sweet fortified wines.

Sweet fortified wines, traditionally aged under strong oxidation conditions, have a characteristic aroma. An experimental laboratory study investigated the aging of red and white sweet fortified wines under various conditions. The formation of various molecules, previously identified as characteristic of the aroma of this type of wine, was monitored by analysis. The development of these compounds during accelerated aging was affected by oxidation and the color of the wine. Among the molecules studied, sotolon [3-hydroxy-4, 5-dimethyl-2(5H)-furanone] was one of the few molecules present in concentrations above the perception threshold, in both red and white wines. Buildup was strongly affected by the presence of oxygen in white wine subjected to accelerated aging. (Ethoxymethyl)furfural, formed from 5-(hydroxymethyl)furfural, and furfural, derived from sugars, are also involved in the aroma of sweet fortified white wines aged in oxygen-free conditions. The substances most characteristic of accelerated aging of sweet fortified red wines were 5-(hydroxymethyl)furfural, acetylformoin, and hydroxymaltol, the formation of which is affected by oxidation, and dihydromaltol, formed in the absence of oxidation.     

Flavoring components of raw monsooned arabica coffee and their changes during radiation processing

Volatile aroma principles, nonvolatile taste constituents (caffeine and chlorogenic and caffeic acids), and glycosidically bound aroma compounds of monsooned and nonmonsooned raw arabica coffee were analyzed using gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography (HPLC). Among the most potent odor active constituents known to contribute to the aroma of the green beans, 3-isopropyl-2-methoxypyrazine, 3-isobutyl-2-methoxypyrazine, 4-vinylguaiacol, beta-damascenone, (E)-2-nonenal, trans,trans-2,4-decadienal, phenylacetaldehyde, and 3-methylbutyric acid were detected by GC-MS in both samples. A decrease in content of methoxypyrazines and an increase in 4-vinylguaiacol and isoeugenol resulted in a dominant spicy note of monsooned coffee. These phenolic compounds exist partly as their glycosides, and their release from the bound precursors during monsooning accounted for their higher content in monsooned coffee. A considerable decrease in astringent chlorogenic acid as a consequence of hydrolysis to bitter caffeic acid was noted in monsooned coffee. Radiation processing of nonmonsooned beans at a dose of 5 kGy resulted in an increased rate of monsooning. At this dose a quantitative increase in most of the aroma active components could be observed in all samples studied. Hydrolysis of chlorogenic acid to caffeic acid was noted in radiation-processed monsooned coffee beans irrespective of whether the treatment was carried out before or after monsooning. These changes were, however, not observed in irradiated, nonmonsooned coffee beans, suggesting an enzymatic rather than a radiolytic cleavage of chlorogenic acid. A rationale behind the mechanism of monsooning and radiation-induced enhancement of the monsooning process is discussed.     

Diversity in Phytochemical Composition and Antioxidant Capacity of Dent,Flint, and Specialty Corns

Dent, flint, and specialty genotypes of Indian yellow maize were evaluated for phytochemical content and their hydrophilic antioxidant capacity. Solid‐phase extraction coupled with solid–liquid extraction was used to obtain free phenolics and flavonoids from maize samples, reducing the use of excessive solvents and handling time. Bound phenolics were extracted with enhanced acidic hydrolysis to improve extractability. The phenolic contents in Indian maize genotypes ranged from 46 to 79 μmol of ferulic acid equivalents per gram of sample on a dry basis (db). Carotenoids in Indian maize genotypes were found to be equivalent to Chinese yellow maize and ranged from 13 to 24 μg/g of sample (db), whereas tocol content varied greatly in the range of 607–1,238 μg of α‐tocopherol equivalents/g of sample (db). Dent and flint corn did not exhibit differences (P > 0.05) in their phenolic contents, whereas among the specialty genotypes sweet corn contained the highest phenolics but least carotenoids (P < 0.05). Bound extracts appeared to contribute largely to 2,2′‐diphenyl‐1‐picrylhydrazyl free radical scavenging, hydrogen peroxide scavenging, and ferric reducing antioxidant power of maize genotypes. Sweet corn exhibited higher antioxidant capacity (P < 0.05) among all the genotypes. The antioxidant capacities correlated well with the total phenolic contents of the maize genotypes.     

Hydrolysis of wine aroma precursors during malolactic fermentation with four commercial starter cultures of Oenococcus oeni

The ability of four commercial preparations of Oenococcus oeni lactic acid bacteria (EQ 54, Lalvin OSU, Uvaferm Alpha, and Lalvin 31) to hydrolyze wine aroma precursors was evaluated by measuring the concentration of free and bound aroma compounds at the end of malolactic fermentation carried out in model wines containing a mixture of glycosides extracted from Muscat wine. At pH 3.4 there was a decrease in glycosylated compounds matched by a concomitant increase in free forms in all starter cultures tested. When malolactic fermentation was carried out at pH 3.2, a significant decrease in the ability to hydrolyze aroma precursors was observed for two of the cultures tested (Uvaferm Alpha and Lalvin 31). Large differences in the extent of hydrolysis and in the specificity of this activity toward specific aroma precursors were observed and appeared to be related to the chemical structure of the aglycon as well as to individual characteristics of each starter culture. The amounts of glycosylated aroma compounds released during malolactic fermentation suggest that O. oeni can alter the sensory characteristics of wine through the hydrolysis of aroma precursors.     

Rowanberry phenolics: compositional analysis and bioactivities

Berries contain a large variety of different phenolic compounds such as anthocyanins, flavonols, tannins, and phenolic acids. Due to variation in the nature and content of the phenolic compounds, the antioxidant effect and other bioactivities of berry phenolics are strongly dependent on the berry raw material as the activities differ between the different phenolic constituents. In the present study, wild rowanberries ( Sorbus aucuparia ) and four cultivated sweet rowanberries, Burka, Granatnaja, Titan, and Zoltaja, were characterized for their phenolic composition and screened for antioxidant, antimicrobial, and antiadhesive activities. The HPLC and LC-MS analyses of phenolic composition revealed that the main phenolic constituents were caffeoylquinic acids, varying from 56 to 80% total phenolics. The cultivated species contained less caffeoylquinic acids and more anthocyanins (up to 28.5%). The phenolics derived from wild rowanberries were significantly effective at inhibiting lipid oxidation both in liposomes and in emulsions, especially when assessed by inhibition of the formation of hexanal (86-97% inhibition depending on concentration). The increase in anthocyanin content in the cultivated species did not result in significantly increased antioxidant activity. Both wild and cultivated rowanberry phenolics exhibited a bacteriostatic effect toward Staphylococcus aureus . In addition, the phenolic extract from Zoltaja was weakly inhibitory toward Salmonella sv. Typhimurium, whereas both Zoltaja- and Granatnaja-derived phenolics retarded Escherichia coli growth. The phenolic extracts of wild rowanberries and Burka showed an inhibitory effect on hemagglutination of E. coli HB101 (pRR7), which expresses the M hemagglutinin. It can be concluded that cultivation of rowanberries resulted in increased anthocyanin content, but this did not diminish their bioactivity in comparison to wild rowanberries rich in caffeoylquinic acids.     

Effect of addition of commercial grape seed tannins on phenolic composition, chromatic characteristics, and antioxidant activity of red wine

The effect of addition of grape seed tannins on the phenolic composition, chromatic characteristics, and antioxidant activity of red wine was studied. Two highly pure commercial grape seed tannins (GSE100 and GSE300) were selected, and their phenolic compositions were determined. Two types of red wines were made with Castela?o/Tinta Miu?da (3/2, w/w) grapevine varieties by fermentation on skin using two different maceration times, which correspond to the wines rich and poor in polyphenols, respectively. Each of these wines was used for experimentation with the addition of GSE100 and GSE300 before and immediately after alcoholic fermentation. Phenolic composition, chromatic characteristics, and antioxidant activity of the finished red wines were analyzed by HPLC-DAD, CIElab 76 convention, and DPPH radical test, respectively. The results showed that the addition of grape seed tannins had obvious effects of increasing color intensity and antioxidant activity only in the wines poor in polyphenols. Although GSE300 contained much higher amounts of di- and trimer procyanidins and a lower amount of polymeric proanthocyanidins, it provided effects of increasing the color intensity and antioxidant activity of the wines poor in polyphenols similar to those of GSE100. Furthermore, GSE100 released more gallic acid to wines than GSE300, although no gallic acid was detected in GSE100. Tannins added after alcoholic fermentation had a better effect on phenolic composition of red wine than tannins added before alcoholic fermentation.     

Analytical and sensorial characterization of the aroma of wines produced with sour rotten grapes using GC-O and GC-MS: identification of key aroma compounds

In the present work, the aroma profiles of wines elaborated from sound and sour rot-infected grapes as raw material have been studied by sensory analysis, gas chromatography-olfactometry (GC-O), and gas chromatography-mass spectrometry (GC-MS), with the aim of determining the odor volatiles most likely associated with this disease. The effect of sour rot was tested in monovarietal wines produced with the Portuguese red grape variety Trincadeira and in blends of Cabernet Sauvignon and sour rotten Trincadeira grapes. Wines produced from damaged berries exhibited clear honey-like notes not evoked by healthy samples. Ethyl phenylacetate (EPhA) and phenylacetic acid (PAA), both exhibiting sweet honey-like aromas, emerged as key aroma compounds of sour rotten wines. Their levels were 1 order of magnitude above those found in controls and reached 304 and 1668 μg L(-1) of EPhA and PAA, respectively, well above the corresponding odor thresholds. Levels of γ-nonalactone also increased by a factor 3 in sour rot samples. Results also suggest that sour rot exerts a great effect on the secondary metabolism of yeast, decreasing the levels of volatiles related to fatty acids and amino acid synthesis. The highest levels of γ-decalactone of up to 405 μg L(-1) were also found in all of the samples, suggesting that this could be a relevant aroma compound in Trincadeira wine aroma.