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At least 109 records · Page 6Linked to original sources
PubMed2006

Accumulation of tocopherols and tocotrienols during seed development of grape (Vitis vinifera L. cv. Albert Lavallée).

Tocopherols and tocotrienols are present in mature seeds. Yet, little is known about the physiological role and the metabolism of these compounds during seed development. Here we present data on tocopherol and tocotrienol accumulation during seed development in Vitis vinifera L. cv. Albert Lavallée (Royal). This species was chosen for its ability to synthesize both tocopherols and tocotrienols. It is shown here for the first time that during seed development there are significant differences in localization and accumulation kinetics of tocopherols and tocotrienols. Tocopherols are found homogeneously dispersed throughout all tissues of the seed, in concentrations ranging from 20 to 100 microg tocopherol per g dry weight. Tocopherol levels decrease gradually during seed development. In contrast, tocotrienols are only found in the endosperm of the seeds, accumulating in a sigmoid fashion during the maturation period of seed development. Tocotrienol levels were found to be (54+/-7.4) microg/g dry seed in 90-day-old seeds of V. vinifera L. Furthermore, tocotrienol biosynthesis is demonstrated in these seeds during tocotrienol accumulation and in an endosperm fraction isolated at 75 days after flowering.

Seeds↗
PubMed2001

Monoterpenic and norisoprenoidic glycoconjugates of Vitis vinifera L. cv. Melon B. as precursors of odorants in Muscadet wines.

The volatile monoterpenic and norisoprenoidic compounds released by glycosidase enzyme hydrolysis of C18 reversed-phase isolates from the juice of Vitis vinifera L. cv. Melon B. have been qualitatively and quantitatively determined using GC-MS and GC-FID. The components analyzed were broadly similar to those previously reported for other varieties but the level of bound p-menth-1-en-7,8-diol was higher in this cultivar. Then the monoterpenic and norisoprenoidic volatiles released from the same glycosidic extracts under mild acid conditions, mimicking wine aging conditions, have been analyzed using GC-Olfactometry and GC-MS. The most odorous compounds detected were p-cymene, terpinen-4-ol, cis- and trans-vitispiranes, 1,6,6-trimethyl-1,2-dihydronaphtalene (TDN), beta-damascenone and riesling acetal. To assess their potential levels in corresponding wines after ageing, most of these odorants were generated by harsh acid hydrolysis from the precursors extracts and quantitatively determined using SPME and GC-MS/MS. For the development and application of this analysis, the odorants not commercialy available were synthesized. The total amounts of norisoprenoidic odorants generated by acid hydrolysis of the glycosidic extracts were shown to be proportional to the total amounts of these precursors.

Gas Chromatography-Mass Spectrometry↗
PubMed2002

Preparative isolation of polyphenolic compounds from Vitis vinifera by centrifugal partition chromatography.

This study deals with a centrifugal partition chromatography developed for the separation of phenolic compounds from Vitis vinifera. EtOAc grape seed extracts were separated using the solvent system hexane-ethyl acetate-ethanol-water (1:8:2:7; v/v) in two fractions: one containing about 75% of flavanol monomers (catechin and epicatechin) corresponding to 18% of crude extract and another fraction B-type dimers (22% of crude extract). From the stalk extracts, we could separate stilbenoid compounds (resveratrol and its oligomers; 12% of crude extract) which were eluted in less than 30 min from flavanols (which required a few hours of additional elution). Using the same solvent system but in different ratios (4:5:3:3; v/v), we isolated the trans-resveratrol (7@1000; 90% purity).

Centrifugation↗
PubMed2001

Anti-inflammatory tetramers of resveratrol from the roots of Vitis amurensis and the conformations of the seven-membered ring in some oligostilbenes.

Five resveratrol tetramers, amurensins I-M, were isolated from the roots of Vitis amurensis (Rupr.), together with five known resveratrol tetramers, (+)-hopeaphenol, isohopeaphenol, vitisin A, (+)-vitisifuran A, and heyneanol A. Their structures and stereochemistry were determined by chemical and spectroscopic methods, especially by use of 2D NMR analysis. Some of them had an ampelopsin A or a balanocarpol unit, in which the conformations of the seven-membered carbon ring were described for the first time. The anti-inflammatory activities of the tetramers were also tested. Among them, (+)-hopeaphenol, isohopeaphenol, vitisin A, (+)-vitisifuran A and heyneanol A showed potent inhibition on the biosynthesis of leukotriene B4 (LTB4), and amurensins I and L showed strong antagonism of the histamine acceptor.

Anti-Inflammatory Agents↗
PubMed2002

Galloylated catechins and stilbene diglucosides in Vitis vinifera cell suspension cultures.

Suspension cultures of Vitis vinifera were found to produce catechins and stilbenes. When cells were grown in a medium inducing polyphenol synthesis, (-)-epicatechin-3-O-gallate, dimeric procyanidin B-2 3'-O-gallate and two resveratrol diglucosides were isolated, together with a new natural compound that was identified as cis-resveratrol-3,4'-O-beta-diglucoside by spectroscopical methods.

Biflavonoids↗
PubMed2003

Stress reactions in Vitis vinifera L. following soil application of the herbicide flumioxazin.

In order to evaluate the stress effects of flumioxazin (fmx) on grapevine, a non-target plant (Vitis vinifera L.), physiological parameters such as carbohydrate content, water status or nitrogenous metabolites were investigated on fruiting cuttings and plants grown in vineyard. In the leaves of cuttings, the soil-applied herbicide induced stress manifestations including a decrease of the dry weight percentage and the soluble carbohydrate content during the first week after treatment. Thereafter, a decrease of the osmotic potential was observed, as well as a decrease of total protein content and a parallel accumulation of free amino acids, including proline. Altogether, these results suggest that soil-applied fmx induced a stress in grapevines, leading to leaf proteolysis. However, this stress was partially recovered 3 weeks after herbicide application, suggesting that the cuttings were capable to adapt to the fmx exposure. In the vineyard, the flumioxazin effects were still significant 5 months after the treatment, particularly in the CH cv. They included a decrease of the leaf dry weight percentage and soluble carbohydrate content, as well as an increase of the osmotic potential. The decrease of leaf soluble carbohydrates may have dramatic consequences for the berry growth and the reserve constitution. Moreover, treated plants were characterized by a decrease of the free amino acid content and an accumulation of ammonium, while the protein level did not significantly increase, suggesting a degradation of amino acids. The alteration of carbon and nitrogen status after herbicide treatment may affect the grapevine vigour in a long term.

Adaptation, Physiological↗
PubMed2006

[Effect of homogeneity on cell growth and anthocyanin biosynthesis in suspension cultures of Vitis vinifera].

The instability of secondary metabolite production is a ubiquitous problem in plant cell culture. To understand the instability, the investigation of anthocyanin accumulation in suspension cultures of Vitis vinifera, as a model system, has been initiated in our laboratory. Suspension culture of a relatively homogeneous cell line E of V. vinifera, was established by long-term cell line selection by anthocyanin content differentiation. The aggregate size of E was smaller than that of other cell lines obtained by routine screening method. The variation coefficients of anthocyanin content in suspension cultures of E were 8.7% in long-term subcultures and 5% in repeated flasks, respectively. The effects of elicitor, precursor feeding and light irridiation on biomass and anthocyanin accumulation in suspension cultures of E had been investigated and the results showed that all the variation coefficients were lower than 12% and this indicated the importance of homogeneity on stable production in plant cell culture. With the combination treatment of 30micromol/L phenylalanine and 218micromol/L methyl jasmonate in the dark in suspension cultures of E, the anthocyanin content and production in suspension culture of E was 5.89-fold and 4.30-fold of the controls, respectively, and all the variation coefficients of biomass and anthocyanin accumulation were lower than those of the controls in 5 successive subcultures.

Anthocyanins↗
PubMed2003

Genetic structure and differentiation in cultivated grape, Vitis vinifera L.

222 cultivated (Vitis vinifera) and 22 wild (V. vinifera ssp. sylvestris) grape accessions were analysed for genetic diversity and differentiation at eight microsatellite loci. A total of 94 alleles were detected, with extensive polymorphism among the accessions. Multivariate relationships among accessions revealed 16 genetic groups structured into three clusters, supporting the classical eco-geographic grouping of grape cultivars: occidentalis, pontica and orientalis. French cultivars appeared to be distinct and showed close affinity to the wild progenitor, ssp. sylvestris from south-western France (Pyrenees) and Tunisia, probably reflecting the origin and domestication history of many of the old wine cultivars from France. There was appreciable level of differentiation between table and wine grape cultivars, and the Muscat types were somewhat distinct within the wine grapes. Contingency chi2 analysis indicated significant heterogeneity in allele frequencies among groups at all loci. The observed heterozygosities for different groups ranged from 0.625 to 0.9 with an overall average of 0.771. Genetic relationships among groups suggested hierarchical differentiation within cultivated grape. The gene diversity analysis indicated narrow divergence among groups and that most variation was found within groups (approximately 85%). Partitioning of diversity suggested that the remaining variation is somewhat structured hierarchically at different levels of differentiation. The overall organization of genetic diversity suggests that the germplasm of cultivated grape represents a single complex gene pool and that its structure is determined by strong artificial selection and a vegetative mode of reproduction.

Genetic Variation↗
PubMed2002

Procyanidins from Vitis vinifera seeds: in vivo effects on oxidative stress.

The purpose of this study was to evaluate the effect of supplementation with procyanidins from Vitis vinifera on markers of oxidative stress. Ten healthy volunteers received a daily dose of 110 mg of procyanidins for 30 days. Fasting venous blood samples were taken before and at the end of the supplementation period and after 7 days of wash-out. The total antioxidant activity and the plasma concentrations of alpha-tocopherol were not modified. Conversely, the levels of alpha-tocopherol in red blood cell membranes increased significantly from 1.8 +/- 0.1 to 2.8 +/- 0.2 mg/g. Similarly, the lymphocyte oxidized DNA [8-oxo-7,8-dihydro-2'-deoxyguanosine/2'-deoxyguanosine ratio] was reduced from 7.23 +/- 2.47 to 2.34 +/- 0.51, and the red blood cell membrane fatty acid composition shifted to a higher level of polyunsaturated fatty acids. On the basis of these results, it may be suggested that dietary procyanidins exert their antioxidant protection in vivo by sparing liposoluble vitamin E and reducing DNA oxidative damage.

Adult↗
PubMed2003

Contribution of benzenemethanethiol to smoky aroma of certain Vitis vinifera L. wines.

Benzenemethanethiol, a volatile thiol with a strong empyreumatic aroma reminiscent of smoke, has been identified in boxwood (Buxus sempervirens L.) as well as in red and white Vitis vinifera L. wines. The perception threshold in a model hydroalcoholic solution is approximately 0.3 ng/L. All of the wines analyzed for this study contained this compound in concentrations of several dozen nanograms per liter. The Chardonnay wines had 30-40 ng/L. Sensory discrimination between a wine containing 7 ng/L benzenemethanethiol and the same wine with an additional 4 ng/L is very significant; the difference in smell is described as "empyreumatic". This compound can therefore significantly contribute to the aroma of certain wines (Sauvignon Blanc, Semillon, Chardonnay, etc.) containing concentrations as high as 30-100 times higher than their perception threshold.

Benzaldehydes↗
PubMed2002

Antioxidant activities of grape (Vitis vinifera) pomace extracts.

Antioxidant-rich fractions were extracted from grape (Vitis vinifera) pomace using ethyl acetate, methanol, and water. The extracts were screened for their potential as antioxidants in different models. The ethyl acetate, methanol, and water extracts showed 76, 87.1, and 21.7% antioxidant activities at 100 ppm, respectively, using the 1,1-diphenyl-2-picrylhydrazyl model system. As the methanol extract of grape pomace showed maximum antioxidant activity among all of the extracts, it was selected to determine its effect on lipid peroxidation, hydroxyl radical scavenging activity, and human low-density lipoprotein (LDL) oxidation. The methanol extract showed 71.7, 73.6, and 91.2% inhibition using the thiobarbituric acid method, hydroxyl radical scavenging activity, and LDL oxidation, respectively, at 200 ppm. Treatment of albino rats of the Wistar strain with a single dose of CCl(4) at 1.25 mL/kg of body weight decreases the activities of catalase, superoxide dismutase (SOD), and peroxidase by 81, 49, and 89%, respectively, whereas the lipid peroxidation value increased nearly 3-fold. Pretreatment of the rats with the methanolic extract of grape pomace at 50 mg/kg (in terms of catechin equivalents) followed by CCl(4) treatment causes restoration of catalase, SOD, and peroxidase by 43.6, 73.2, and 54%, respectively, as compared with control, whereas lipid peroxidation was restored to values comparable with the control. Histopathological studies of the liver of different groups also support the protective effects exhibited by the methanol extract of grape pomace by restoring the normal hepatic architecture. Owing to this property, the studies on grape pomace can be further extended to exploit its possible application for the preservation of food products as well as a health supplement and neutraceutical.

Acetates↗
PubMed2002

Valorization of grape (Vitis vinifera) byproducts. Antioxidant and biological properties of polyphenolic fractions differing in procyanidin composition and flavonol content.

Many byproducts and wastes generated by agroindustries contain polyphenols with potential application as food antioxidants and preventive agents against skin cancer and other diseases. The performance of polyphenolic fractions from Parellada grape (Vitis vinifera) pomace as antioxidants in different physicochemical environments was tested. Fractions containing oligomers with mean degree of polymerization between 3 and 4 and percentage galloylation ca. 30% were the most potent free radical scavengers and efficient antioxidants in an oil-in-water emulsion. A fraction including glycosylated flavonols was also efficient in the emulsion. All the fractions showed low aquatic toxicity and weak influence on proliferation of human melanoma cells.

Antioxidants↗
PubMed2003

Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon.

The monomeric, oligomeric, and polymeric flavan-3-ol composition of wines, grape seeds, and skins from Vitis vinifera L. cv. Graciano, Tempranillo, and Cabernet Sauvignon has been studied using (1) fractionation by polyamide column chromatography followed by HPLC/ESI-MS analysis, (2) fractionation on C(18) Sep-Pak cartridges followed by reaction with vanillin and acid-catalyzed degradation in the presence of toluene-alpha-thiol (thiolysis). The content of monomers ((+)-catechin and (-)-epicatechin), procyanidin dimers (B3, B1, B4, and B2), trimers (T2 and C1), and dimer gallates (B2-3-O-gallate, B2-3'-O-gallate, and B1-3-O-gallate) ranged from 76.93 to 133.18 mg/L in wines, from 2.30 to 8.21 mg/g in grape seeds, and from 0.14 to 0.38 mg/g in grape skins. In wines, the polymeric fraction represented 77-84% of total flavan-3-ols and showed a mean degree of polymerization (mDP) value of 6.3-13.0. In grapes, the polymeric fraction represented 75-81% of total flavan-3-ols in seeds and 94-98% in skins and showed mDP values of 6.4-7.3 in seeds and 33.8-85.7 in skins. All the monomeric flavan-3-ols and oligomeric procyanidins found in wines were also present in seeds, although differences in their relative abundances were seen. The skin polymeric proanthocyanidins participated in the equilibration of the wine polymeric proanthocyanidin fraction, especially contributing to the polymer subunit composition and mDP.

Biflavonoids↗
PubMed2003

A simple extraction and chromatographic system for the simultaneous analysis of anthocyanins and stilbenes of Vitis species.

A separation system has been developed to permit the simultaneous analysis of major anthocyanins and stilbenes from berries of Vitis species in <1 h. The system makes use of separation by HPLC and detection by UV-visible absorption and fluorescence, for anthocyanins and stilbenes, respectively, with the two detection systems linked in series. Monitoring the absorption at 520 nm permits ready identification and quantification of major anthocyanins. Chromatograms derived from fluorescence (330 nm excitation/374 nm emission) produce less clear data for the piceids and resveratrols, which are present in much lower amounts; peaks for these compounds can be verified by means of external or internal standards.

Anthocyanins↗
PubMed2004

Enantioselective analysis of free and glycosidically bound monoterpene polyols in Vitis vinifera L. cvs. Morio Muscat and Muscat Ottonel: evidence for an oxidative monoterpene metabolism in grapes.

The enantiomeric ratios of various free and glycosidically bound monoterpene polyols in musts of the aromatic grapes Vitis vinifera L. cvs. Morio Muscat and Muscat Ottonel were determined by means of enantioselective multidimensional gas chromatography-mass spectrometry. Reference compounds of defined stereochemistry were synthesized and permitted the unequivocal determination of the elution order of the target compounds on chiral columns with modified cyclodextrins as stationary phases. It could be shown for the first time that the linalool-derived polyol 3,7-dimethylocta-1,7-dien-3,6-diol occurs predominately as the (3S,6S)-configured stereoisomer, providing evidence that this compound is generated by an enzymatic process in grape berries. The involvement of a cytochrome P450 monooxygenase in the oxidative metabolism of monoterpenes in grapes is dicussed.

Acyclic Monoterpenes↗
PubMed2003

Metabolism of fungicide diethofencarb in grape (Vitis vinifera L.): definitive identification of thiolactic acid conjugated metabolites.

The metabolic fate of diethofencarb (isopropyl 3,4-diethoxycarbanilate) separately labeled with (14)C at the phenyl ring and 2-position of the isopropyl moiety was studied in grape (Vitis vinifera L.). The acetonitrile solution of (14)C-diethofencarb at a rate of 500 g a.i. ha(-)(1) was once applied topically to fruits or leaves at the maturity stage of fruits (PHI 35 days), and the plants were grown in the greenhouse until harvest. In the grape plants, diethofencarb was scarcely translocated to the untreated portion and was degraded more in the fruit as compared to the leaf. For the fruit, diethofencarb primary underwent O-deethylation at the 4-position of the phenyl ring to form the phenolic derivative, isopropyl 3-ethoxy-4-hydroxycarbanilate (0.9% of the total radioactive residue, TRR). This metabolite was successively transformed via conjugation with glucose at the phenolic hydroxy group (8.1-18.1% TRR) or with thiolactic acid at the 5-position of the phenyl ring (1.5-1.7% TRR). The thiolactic acid conjugate was further metabolized mainly to two different types of glucose conjugates at the 4-position of the phenyl ring (8.7-13.5% TRR) and the hydroxy group in the thiolactic acid moiety (6.4-7.3% TRR), as evidenced by (1)H NMR and atmospheric pressure chemical ionization-liquid chromatography-mass spectrometry together with cochromatographies with synthetic standards.

Carbamates↗
PubMed2003

Vitisin A content in Chilean wines from Vitis vinifera Cv. Cabernet Sauvignon and contribution to the color of aged red wines.

Vitisin A was prepared from malvidin 3-glucoside and pyruvic acid in model wine medium, isolated by countercurrent chromatography, and purified by preparative high-performance liquid chromatography (HPLC). The synthesized compound was used as a reference standard to quantify vitisin A in Chilean wines from Vitis vinifera cv. Cabernet Sauvignon, including a vertical row of wines from the same vineyard over 16 years. Maximum vitisin A content was reached within the first year of storage. Importantly, up to half of the initial amount of vitisin A in young wines was still present in 15 year old wines. Although vitisin A was found to be much more stable as compared to other monomeric C-4 underivatized anthocyanins, it also slowly degrades after reaching its peak concentration. The "color activity concept" was applied to vitisin A, malvidin 3-glucoside, malvidin 3-(6' '-acetylglucoside), and polymeric pigments isolated by countercurrent chromatography in order to estimate their contribution toward the overall color expression of wines. It was found that vitisin A is only a minor contributor to the visually perceived color of aged red wines (color contribution approximately 5%). The major contributor is the polymeric fraction (color contribution approximately 70-90%).

Benzofurans↗
PubMed2004

Polyphenol glucosylating activity in cell suspensions of grape (Vitis vinifera).

Stilbenes are phenolic molecules that have antifungal effects in the plant and antioxidant and anti-cancer effects when consumed in the human diet. Glycosylation of stilbenes increases their solubility and may make them more easily absorbed by the intestine. We have found an activity in extracts of cultured cells of Vitis vinifera (cv. Gamay Freaux) that glucosylates the stilbene resveratrol to form piceid. The Km for UDP-Glucose was 1.2 mM, and the Km for resveratrol was 0.06 mM, values similar to those of other phenolic glucosyltransferases. We investigated the resveratrol glucosylating activity of the enzyme extracted from cells grown under different light treatments (dark, visible light, light + ultraviolet (UVC) radiation) and found the activity to be unaffected or slightly reduced. In contrast, UVC light strongly stimulated extractable quercetin glucosyltransferase activity. These results, combined with analysis of phenolic compounds extracted from the differently treated cells, suggest that the resveratrol glucosyltransferase is distinct from the glucosyltransferase(s) active on other phenolics.

Cells, Cultured↗