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PubMed2004

Effects of commercial anthocyanin-rich extracts on colonic cancer and nontumorigenic colonic cell growth.

Commercially prepared grape (Vitis vinifera), bilberry (Vaccinium myrtillus L.), and chokeberry (Aronia meloncarpa E.) anthocyanin-rich extracts (AREs) were investigated for their potential chemopreventive activity against colon cancer. The growth of colon-cancer-derived HT-29 and nontumorigenic colonic NCM460 cells exposed to semipurified AREs (10-75 microg of monomeric anthocyanin/mL) was monitored for up to 72 h using a sulforhodamine B assay. All extracts inhibited the growth of HT-29 cells, with chokeberry ARE being the most potent inhibitor. HT-29 cell growth was inhibited approximately 50% after 48 h of exposure to 25 microg/mL chokeberry ARE. Most importantly, the growth of NCM460 cells was not inhibited at lower concentrations of all three AREs, illustrating greater growth inhibition of colon cancer, as compared to nontumorigenic colon cells. Extracts were semipurified and characterized by high-pressure liquid chromatography, spectrophotometry, and colorimetry. Grape anthocyanins were the glucosylated derivatives of five different anthocyanidin molecules, with or without p-coumaric acid acylation. Bilberry contained five different anthocyanidins glycosylated with galactose, glucose, and arabinose. Chokeberry anthocyanins were cyanidin derivatives, monoglycosylated mostly with galactose and arabinose. The varying compositions and degrees of growth inhibition suggest that the anthocyanin chemical structure may play an important role in the growth inhibitory activity of commercially available AREs.

Anthocyanins↗
PubMed2005

Stability of copigmented anthocyanins and ascorbic acid in a grape juice model system.

The stability of red grape anthocyanins (Vitis vinifera) was evaluated in a model juice system during normal (25 degrees C) and accelerated storage (35 degrees C) in the presence of ascorbic acid. Rosemary polyphenolic cofactors (0, 0.2, and 0.4% v/v) were evaluated as anthocyanin stabilizing agents. Cofactor addition resulted in concentration-dependent hyperchromic (up to 178%) and bathochromic (up to 23 nm) shifts, indicating a more intense red coloration of the models. Anthocyanin and ascorbic acid degradation followed first-order kinetics during storage. Results showed that copigmented treatments underwent a lower conversion of L-ascorbic acid into dehydroascorbic acid during storage when compared to the control, favorably impacting the vitamin retention of these models. Copigmentation did not affect anthocyanin degradation in the absence of ascorbic acid but in its presence aided to retain a higher anthocyanin content than the control. This study indicated that the addition of anthocyanin cofactors could be used to reduce the pigment and vitamin degradation while masking detrimental color changes in anthocyanin containing products.

Anthocyanins↗
PubMed2005

Carotenoid, chlorophyll, and chlorophyll-derived compounds in grapes and port wines.

Carotenoids and chlorophyll-derived compounds in grapes and Port wines were investigated by HPLC-DAD and HPLC-DAD-MS (ESP+) analysis. A total of 13 carotenoid and chlorophyll-derived compounds are formally reported in grapes, 3 are identified for the first time, pheophytins a and b and (13Z)-beta-carotene, and 3 others remain unknown. In Port wines 19 compounds with carotenoid or chlorophyll-like structures are present, 8 still unidentified. The young wines showed higher total carotenoid content and chlorophyll-like compounds compared to aged Ports, with lutein and beta-carotene as major carotenoids. Among samples analyzed of monovarietal Vitis vinifera L. cultivar wines produced with the five most important Douro varieties, Tinta Roriz contained the highest levels of carotenoids and Touriga Franca the lowest. The forced-aging study indicated that lutein was more sensitive to temperature than beta-carotene. Additionally, aged wines showed higher ratios of beta-carotene/lutein concentrations compared to new Ports. Rates of degradation of chlorophyll derivative compounds were higher than those for carotene and lutein.

Carotenoids↗
PubMed2005

Fast access of some grape pigments to the brain.

Anthocyanins represent the main flavonoid pigments in red grape and wine, in red berries, and in many other fruits and vegetables and are widespread in the human diet. After ingestion, these complex, hydrophilic compounds quickly appear as intact molecules in the plasma. This study investigated their presence in the brain of anesthetized rats that received 8 mg/kg of body weight of a pure anthocyanin mixture extracted from Vitis vinifera grapes. The mixture was maintained in the stomach for 10 min. After this time, intact anthocyanins were detected by HPLC-DAD-MS not only in the plasma (176.4 +/- 50.5 ng/mL, mean +/- SEM) but also in the brain (192.2 +/- 57.5 ng/g). These results demonstrate for the first time that grape pigments can reach the mammalian brain within minutes from their introduction into the stomach.

Animals↗
PubMed2006

Modified cyclodextrins are chemically defined glucan inducers of defense responses in grapevine cell cultures.

In grapevine (Vitis vinifera L.), defense responses after microbial infection or treatment with elicitors involve accumulation of phytoalexins, oxidative burst, and the synthesis of pathogenesis-related proteins. Oligosaccharide fractions from fungal or algal cell walls efficiently induce the defense responses, but a detailed analysis of the elicitor-plant cell surface interaction at the molecular level is precluded by the lack of chemically pure oligosaccharide elicitors. A grapevine liquid cell culture system was used to examine the properties of cyclodextrins (CDs) as inducers of defense responses. This work shows that the chemically pure heptakis(2,6-di-O-methyl)-betaCD caused a dramatic extracellular accumulation of the phytoalexin resveratrol and changes in peroxidase activity and isoenzymatic pattern. Other modified CDs tested on several grapevine cell lines resulted in different eliciting capacities of CDs and different sensibilities of the cell lines. The spent medium of elicited cultures was shown to disturb Botrytis cinerea growth in a plate assay.

Botrytis↗
PubMed2006

Metabolic changes of Malvasia grapes for wine production during postharvest drying.

Malvasia (Vitis vinifera L.) grapes were harvested at 17.8% of soluble solids content (SSC) and placed inside an innovative dehydration room where temperature, relative humidity, and air flow were maintained, respectively, at 15 degrees C, 40%, and 1-1.5 m s(-1). Weight loss of bunches reached approximately 33% in 29 days. SSC increased inversely proportionally with the weight decrease, reaching at the end of experiment 23%. Abscisic acid (ABA) increased rapidly from around 29 to 80 microg g(-1) of dry weight at 11.7% of bunch weight loss and then declined gradually. Lipoxygenase (LOX) showed the same behavior as ABA, whereas alcohol dehydrogenase (ADH), read in the way of ethanol oxidation, increased continuously when the weight loss reached approximately 19.5%. In parallel with the activity of LOX, C6 compound [hexanal, hex-1-enol, (E)-hex-2-enal] concentrations reached a peak at 11.7% of weight loss, whereas ethanol and acetaldehyde increased with the increase of ADH and successively decrease and ethyl acetate increased. Proline increased initially as ABA and successively with the increase of ADH, 5.3-fold increase versus 4.2-fold increase of proteins. Postharvest dehydration of Malvasia grapes shows a biphasic pattern: a first metabolic stress response up to 11.7% of bunch weight loss and a second stress response beyond 19.5% of weight loss. The metabolic mechanism of these postharvest water stress responses is discussed.

Abscisic Acid↗
PubMed2006

Use of Aloe vera gel coating preserves the functional properties of table grapes.

Table grapes (Vitis vinifera L. cv. Crimson Seedless) were coated with Aloe vera gel according to our developed patent (SP Patent P200302937) and then stored for 35 days at 1 degrees C, and the subsequent shelf life (SL) was monitored at 20 degrees C. Uncoated clusters showed a rapid loss of functional compounds, such as total phenolics and ascorbic acid. These changes were accompanied by reduction of the total antioxidant activity (TAA) and increases in total anthocyanins, showing an accelerated ripening process. On the contrary, table grapes coated with Aloe vera gel significantly delayed the above changes, such as the retention of ascorbic acid during cold storage or SL. Consequently, Aloe vera gel coating, a simple and noncontaminating treatment, maintained the functional properties during postharvest storage of table grapes.

Aloe↗
PubMed2006

Influence of different phenolic copigments on the color of malvidin 3-glucoside.

The effectiveness of seven phenolic compounds (catechin, epicatechin, procyanidin B2, caffeic acid, p-coumaric acid, myricitrin, and quercitrin) as copigments of malvidin 3-glucoside, the major anthocyanin in red wines from Vitis vinifera, using a copigment/pigment molar ratio of 1:1 was assayed in model wine solutions under the same conditions (pH=3.6, 12% ethanol). The stability of the copigment-pigment complexes formed was studied during a storage period of 60 days at 25 degrees C. Tristimulus colorimetry was applied for color characterization of the copigmentation process, and HPLC-DAD-MS was used to monitor changes in the composition of the samples. Copigmentation has been found to occur in all cases despite the low copigment/pigment molar ratio used, although the effect was different depending on the compound. Flavan-3-ols appeared as the less effective copigments, procyanidin B2 being even worse than monomeric flavanols, whereas flavonols behaved as the best ones. These latter copigments also induced the most statistically significant bathochromic shift in lambdamax. In the colorimetric analysis, it was observed that the lightness L* of the copigmented solutions increased with time, chroma C*ab decreased, and the hue hab increased. The copigments that produced a greater increase in the hue angle were the monomeric flavan-3-ols, which therefore showed to be the least protective cofactors against browning of the anthocyanin solution during the storage. With the time of storage, the formation of new pigments was observed in the solutions containing flavanols (xanthylium structures) and hydroxycinnamic acids (pyranoanthocyanins), which explains some of the color modifications produced in these solutions. Another relevant observation was that the stability of the anthocyanin was not much improved by most of the assayed copigments, since quite similar degradation rates were observed in the presence and absence of those cofactors.

Anthocyanins↗
PubMed2006

Hydrolysis and transformation of grape glycosidically bound volatile compounds during fermentation with three Saccharomyces yeast strains.

The ability of three Saccharomyces wine yeasts (S. cerevisiae AWRI 838, S. cerevisiae AWRI 1537, and S. bayanus AWRI 1375) to liberate volatile compounds from sugar-bound aroma precursors was investigated using synthetic and grape glycosides under different experimental conditions. In model systems involving the incubation of yeast cells with either synthetic or grape-derived glycosides under conditions more favorable for glycosidase activities and less favorable for acid-catalyzed hydrolysis (pH 5.0 and 30 degrees C), all yeast strains studied proved to be capable of hydrolyzing glycosides, with S. bayanus AWRI 1375 displaying greater hydrolytic activity than S. cerevisiae AWRI 838 and AWRI 1537. During the fermentation of a chemically defined grape juice-like medium containing glycosidic precursors extracted from Vitis vinifera cv. White Frontignac (synonym Muscat à Petit Grains Blanc), all yeasts promoted a significant hydrolysis of different precursors, which varied according to the chemical structures of both the sugar and the aglycon moieties, as determined by GC-MS analysis of trifluoroacetylated derivatives. Hydrolysis of the White Frontignac derived glycosidic precursors during fermentation resulted in the release of monoterepene alcohols, terpene oxides, terpene diols, and 3-oxo-alpha-ionol, demonstrating the significant potential of these yeast strains to contribute to wine varietal volatile composition during alcoholic fermentation.

Fermentation↗
PubMed2006

Metabolite profiling of grape: Flavonols and anthocyanins.

Flavonols are products of the flavonoid biosynthetic pathway, which also give rise to anthocyanins and condensed tannins in grapes. We investigated their presence in the berry skins of 91 grape varieties (Vitis vinifera L.), in order to produce a classification based on the flavonol profile. The presence of laricitrin 3-O-galactoside and syringetin 3-O-galactoside in red grapes is reported here for the first time. In red grapes, the main flavonol was quercetin (mean = 43.99%), followed by myricetin (36.81%), kaempferol (6.43%), laricitrin (5.65%), isorhamnetin (3.89%), and syringetin (3.22%). In white grapes, the main flavonol was quercetin (mean = 81.35%), followed by kaempferol (16.91%) and isorhamnetin (1.74%). The delphinidin-like flavonols myricetin, laricitrin, and syringetin were missing in all white varieties, indicating that the enzyme flavonoid 3',5'-hydroxylase is not expressed in white grape varieties. The pattern of expression of flavonols and anthocyanins in red grapes was compared, in order to gain information on the substrate specificity of enzymes involved in flavonoid biosynthesis.

Anthocyanins↗
PubMed2006

Methyl jasmonate induces defense responses in grapevine and triggers protection against Erysiphe necator.

Grapevine is subject to a number of diseases that affect yield and wine quality. To limit the excessive use of phytochemicals in the vineyard, alternative strategies have to be developed. Plant treatment with signaling molecules like elicitors stimulates their natural defense mechanisms. To improve grapevine tolerance against fungal pathogens, Vitis vinifera plants were treated with a natural exogenous elicitor, methyl jasmonate (MeJA). MeJA-treated leaves (Cabernet Sauvignon foliar cuttings) reacted by increasing transcript levels coding pathogenesis-related proteins (acidic class IV chitinase, serine protease inhibitor, polygalacturonase-inhibiting protein, and beta-1,3-glucanase) and coding enzymes involved in phytoalexin biosynthesis (one phenylalanine ammonia lyase and one stilbene synthase). This was correlated with the accumulation of stilbenes (antimicrobial compounds). The eliciting activity of MeJA was confirmed by enhanced tolerance of grapevine foliar cuttings and vineyard against powdery mildew (75% and 73%, respectively). On the basis of these original results, MeJA can therefore act as an efficient elicitor in an alternative strategy of grapevine protection.

Acetates↗
PubMed2006

Composition and cellular localization of tannins in Cabernet Sauvignon skins during growth.

For two successive years, cell walls were isolated from the internal part of skin cells of Vitis vinifera L. cv. Cabernet Sauvignon grape berries grown in a vineyard. Procyanidin localization and composition were determined over the course of development. Tannins were mainly localized in the inner cell fraction, due to their biosynthesis and storage. Cell wall tannins always exhibited a higher mean degree of polymerization as compared to the internal cell fraction, which had a constant mDP. The mDP of cell wall tannins also tended to increase at the end of maturation. Our results suggest tannin polymerization near the cell wall but an aggregation in the vacuole during growth. The tannin composition was typical of skins, and small differences were noted between the two cell parts. Surprisingly, epigallocatechin-3-gallate was also detected, although in a very small amount. Epicatechin was present in significant proportions in both fractions, especially as an extension subunit, while epigallocatechin was likewise abundant, also as a terminal subunit. Last, procyanidin composition and organization seemed to be characteristic of the Cabernet Sauvignon variety.

Biflavonoids↗
PubMed2002

The vascular expression pattern directed by the Eucalyptus gunnii cinnamyl alcohol dehydrogenase EgCAD2 promoter is conserved among woody and herbaceous plant species.

Cinnamyl alcohol dehydrogenase (CAD; EC 1.1.1.195) catalyses the last step in the synthesis of the monomeric precursors of lignin. Here, we demonstrate that the vascular expression pattern conferred by the Eucalyptus gunnii EgCAD2 promoter in transgenic poplar (Populus tremula x Populus alba) is conserved in another perennial woody angiosperm of economic interest (Vitis vinifera L.), as well as in a model herbaceous plant (Nicotiana tabacum L.). Furthermore, promoter deletion analysis performed in both tobacco and poplar allowed us to identify the proximal region [-340/-124] as essential for vascular cambium/xylem-specific expression whereas the [-124/+117] region was shown to contain cis element-driving activity in phloem fibres. Interestingly, the [-340/-124] fragment contains an AC-rich cis-acting element present in numerous genes of the phenylpropanoid pathway expressed in xylem tissues, and known as a consensus Myb transcription factor binding site, suggesting that common Myb sites may provide a mechanism by which different steps of phenylpropanoid metabolism are coordinately regulated and expressed in vascular tissues. We have also shown in both tobacco and poplar that the EgCAD2 promoter is inducible by wounding and the cis-elements responsible for wounding responsiveness are located in the distal promoter region. Taken together, our data suggest that the mechanisms controlling developmental and wounding inducible expression of the EgCAD2 promoter are conserved among perennial woody and annual herbaceous plant species enabling us now to investigate in depth the transcriptional regulation of the EgCAD2 promoter in tobacco.

Alcohol Oxidoreductases↗
PubMed2004

Expression of the stilbene synthase (StSy) gene from grapevine in transgenic white poplar results in high accumulation of the antioxidant resveratrol glucosides.

When present, stilbene synthase leads to the production of resveratrol compounds, which are major components of the phytoalexin response against fungal pathogens of the plant and are highly bioactive substances of pharmaceutical interest. White poplar (Populus alba L.) was transformed with a construct containing a cDNA insert encoding stilbene synthase from grapevine (Vitis vinifera L.), under the control of the cauliflower mosaic virus (CaMV) 35S promoter, and a chimeric kanamycin resistance gene. Southern blot hybridization analysis demonstrated the presence and integration of exogenous DNA sequences in the poplar genome. Expression of the stilbene synthase-encoding gene in different transgenic lines was confirmed by Western blot and Northern analyses. Compared to the controls, in the transgenic plants two new compounds were detected and were identified as the trans- and cis-isomers of resveratrol-3-glucoside (piceid) by high-pressure liquid chromatography (HPLC), UV spectrophotometry, electrospray mass spectrometry (HPLC-ESI-MS) and enzymatic hydrolysis. Since poplar is a good biomass producer and piceids are accumulated in substantial amounts (up to 615.2 microg/g leaf fresh weight), the transgenic plants represent a potential alternative source for the production of these compounds with high pharmacological value. Despite the presence of piceid, in our experimental conditions no increased resistance against the pathogen Melampsora pulcherrima, which causes rust disease, was observed when in vitro bioassays were performed.

Acyltransferases↗
PubMed2002

Influence of Saccharomyces cerevisiae strains on fermentation and flavor compounds of white wines made from cv. Emir grown in Central Anatolia, Turkey.

The effect of inoculation with selected Saccharomyces cerevisiae strains was studied on fermentation and flavor compounds of wines made from Vitis vinifera L. cv. Emir grown in Central Anatolia, Turkey. Flavor compounds were analysed and identified by GC-FID and GC-MS, respectively. The total concentrations of flavor compounds did not increase with the addition of indigenous and commercial wine yeasts, but differences were noted in individual volatile compounds. Cluster and factor analyses of flavor compounds also showed that wines produced were different depending on the wine strain used. Wines were completely fermented to less than 1.4 g/l residual sugar. Yeasts other than S. cerevisiae survived longer than previously reported. Inoculation with selected strains increased the ethanol level.

Aerobiosis↗
PubMed2002

Locating the sources of an invasive pest, grape phylloxera, using a mitochondrial DNA gene genealogy.

Range expansions through human introductions have increased with global commerce and have led to the extinction of native species, alterations in community structure and pest status of the invasive species. Inferring the evolutionary history of invasive species can help to build a firmer footing for management tactics. This study used mitochondrial DNA (mtDNA) sequence comparisons of samples collected from the native and introduced ranges of a pest herbivore of cultivated grapes, grape phylloxera (Daktulosphaira vitifoliae Fitch, Phylloxeridae) to infer the sources and pattern of introductions into worldwide viticulture. Introductions into viticulture from its native North American range first occurred in the mid-19th century. The pattern of spread has suggested a focus of introduction into France, but independent introductions may have occurred elsewhere. The results show that the introduced population represents a limited subsample of the native genetic diversity. The data suggest that most grape phylloxera in viticulture, including all European, have originated in the northeastern USA where the grape species Vitis riparia dominates. There was evidence for independent introductions into South Africa and California. Most California haplotypes were most closely related to native grape phylloxera from the Atlantic Coast on V. vulpina. It is likely that subsequent spread from California into Australia, New Zealand and Peru has occurred.

Animals↗
PubMed2002

Resveratrol acts as a natural profungicide and induces self-intoxication by a specific laccase.

The grapevine (Vitis) secondary metabolite resveratrol is considered a phytoalexin, which protects the plant from Botrytis cinerea infection. Laccase activity displayed by the fungus is assumed to detoxify resveratrol and to facilitate colonization of grape. We initiated a functional molecular genetic analysis of B. cinerea laccases by characterizing laccase genes and evaluating the phenotype of targeted gene replacement mutants. Two different laccase genes from B. cinerea were characterized, Bclcc1 and Bclcc2. Only Bclcc2 was strongly expressed in liquid cultures in the presence of either resveratrol or tannins. This suggested that Bclcc2, but not Bclcc1, plays an active role in the oxidation of both resveratrol and tannins. Gene replacement mutants in the Bclcc1 and Bclcc2 gene were made to perform a functional analysis. Only Bclcc2 replacement mutants were incapable of converting both resveratrol and tannins. When grown on resveratrol, both the wild type and the Bclcc1 replacement mutant showed inhibited growth, whereas Bclcc2 replacement mutants were unaffected. Thus, contrary to the current theory, BcLCC2 does not detoxify resveratrol but, rather, converts it into compounds that are more toxic for the fungus itself. The Bclcc2 gene was expressed during infection of B. cinerea on a resveratrol-producing host plant, but Bclcc2 replacement mutants were as virulent as the wild-type strain on various hosts. The activation of a plant secondary metabolite by a pathogen introduces a new dimension to plant-pathogen interactions and the phytoalexin concept.

Amino Acid Sequence↗
PubMed2002

Are xylem radial development and hydraulic conductivity in downwardly-growing grapevine shoots influenced by perturbed auxin metabolism?

Downwardly-growing grapevine shoots have smaller and more frequent vessels than upwardly-growing ones and, as a consequence, a lower hydraulic conductivity. Here, grapevine (Vitis vinifera L.) shoot growth orientation was manipulated to test whether downward shoot orientation negatively affects vessel growth in the apex via a shortage of water and nutrients. The orientation of the central vine shoot portion was inverted by two consecutive 135 degrees bends, resulting in double-bent N-shaped vines; the central downward shoot portion was of different lengths in the experimental treatments to induce increasing reductions of shoot conductivity. These treatments reduced shoot conductivity and water flow, but had no effects on vessel development and frequency in the apex. In a second experiment, auxin concentration was assessed in shoots of upwardly- and downwardly-growing plants. IAA concentration at the apical internodes was higher in downwardly-oriented shoots than in shoots growing upwards. In addition, a higher density and a lower vessel diameter were observed in the lower, than the upper side, of the downwardly-oriented shoot, suggesting increased accumulation of auxin in the lower side. These results suggest that the downward orientation induces accumulation of auxin in the apex, which in turn affects the density and the size of the xylem vessels, causing reduction of hydraulic conductivity.

Biological Transport↗