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Resveratrol Content of Muscadine Berries is Affected by Disease Control Spray Program
Abstract
Control of muscadine diseases is necessary to minimize yield loss and is especially important for highest quality fresh-market berries. In a systematic disease control spray program, four fungicides registered for grapes were applied sequentially at 10- to 20-day intervals from early bloom until just before harvest to five muscadine cultivars. Objectives of the study were to: 1) determine the effects of the spray schedule on foliage and berry diseases; and 2) study the relationship between disease incidence and resveratrol content of the berries. Resveratrol, a phytoalexin, has shown potential value in prevention and treatment of cardiovascular disease and certain cancer processes. Foliar diseases were rated visually twice during the season. Berry disease ratings were made at harvest. All fungal foliage and berry diseases were significantly reduced by fungicide treatments. Resveratrol was determined separately on berry skins, seed and pulp/juice by gas chromatography/mass spectroscopy (GC/MS). Overall, resveratrol levels in berry skins from unsprayed vines were much higher than those of sprayed vines. Concentrations varied by cultivar and within cultivar by treatment. The relationship between resveratrol concentration in skins and total disease score or scores of specific diseases was not established. Seed resveratrol concentrations differed by cultivar but were not affected by the fungicide treatments. Resveratrol concentration of seed was lower than that of skins. Accumulation of resveratrol in juice/pulp was much lower than in skins and seeds.
... Additionally, fungicide pre-storage treatment was ineffective in managing decay during storage, although microbial spoilage was the major factor contributing to postharvest deterioration (Takeda et al., 1982). Field fungicide applications have been shown to increase resveratrol concentrations in V. vinifera wine grapes but reduce resveratrol concentrations in muscadines (Jeandet et al., 1995;Magee et al., 2002). The effects of field fungicide applications on other nutraceutical compounds in muscadines are unknown. ...
... We found resveratrol concentrations similar to those previously reported in muscadines (Ector et al., 1996;Magee et al., 2002;Marshall et al., 2012;Pastrana-Bonilla et al., 2003;Stringer et al., 2009). In 2012, no fungicide-treated AM 17 had the highest resveratrol concentration (16.7 mg/100 g) and fungicide-treated 'Supreme' had the lowest (2.9 mg/100 g), whereas in 2013, no fungicide-treated 'Supreme' had the highest resveratrol concentration (12.1 mg/100 g), whereas no fungicide-treated 'Southern Jewel' had the lowest (3.2 mg/100 g) (Table 3). ...
... We found no clear relationship between berry color and resveratrol concentrations; conversely, Ector et al. (1996) found resveratrol to be greater in black genotypes. Magee et al. (2002) found 'Summit' to have among the highest levels of resveratrol, which is similar to our findings (Table 3). Resveratrol concentrations were equivalent to those in V. vinifera (Vincenzi et al., 2013). ...
A major limiting factor in fresh-market muscadine grape (Vitis rotundifolia Michx.) commercialization is fruit deterioration during storage. Research on table grapes has shown that field fungicide applications increase storability, but little is known of their effect on muscadines. The effect of field applications of fungicides on
physicochemical attributes during postharvest storage and nutraceutical content at date of harvest was evaluated on five muscadine cultivars (Nesbitt, Southern Jewel, Summit, Supreme, and Tara) and four breeding selections from the University of Arkansas Fruit Breeding Program in 2012 and 2013. There were two field treatments (no fungicide and fungicide). For the fungicide treatment, alternating applications of two fungicides were applied to the vine at 14-day intervals during berry maturation. Fruit was harvested and physicochemical attributes including berry volume, titratable acidity (TA), pH, soluble solids (%), color (L, chroma, and hue), firmness (force to penetrate berry skins and flesh), storage weight loss (%), and unmarketable fruit (%) were evaluated every 7 days for 3 weeks. Whole muscadine berries were analyzed for nutraceutical content only for the date of harvest. As a result of less decay, less weight loss, and greater firmness during storage, AM 27, ‘Southern Jewel’, and ‘Supreme’ had the highest potential for postharvest storage, whereas AM 01, AM 15, and ‘Tara’ had the least potential. Nutraceutical content varied by genotypes; overall AM 27 had the highest nutraceutical content [sum of anthocyanins, total phenolics, flavonols, resveratrol, and oxygen radical absorbance capacity (ORAC)], whereas ‘Supreme’ and AM 28 had the lowest. Total anthocyanins were only found in the black genotypes and total phenolics and resveratrol were unaffected by fungicide treatment. Total ellagitannins varied among the fungicide
treatments. Total flavonols were generally greater in the no fungicide treatments, whereas ORAC was generally greater with fungicide treatments. Year of study and genotype were determined to be major contributors as sources of variation. Although field fungicide applications did not affect all postharvest attributes and nutraceutical components, differences among genotypes and fungicide treatments did occur.
... The association between phytoalexins and disease resistance in Vitis sp. has been well-documented [24,25]. Magee et al. [26] reported that the level of resveratrol in muscadine grapes is reduced when fruit diseases are controlled by fungicide applications. ...
... This cost can be lowered if effective fungicides are applied on a reduced schedule while maintaining effective disease control. However, a previous study [26] indicated that effective fruit disease control may result in reduced quantities of resveratrol and other beneficial phytochemicals in the fruit. Therefore, it is desirable to identify fungicide application schedules that are effective in reducing berry diseases without reducing phytochemical content. ...
... Resveratrol levels reported by Stringer et al. [34] ranged from 2.5 to more than 25 mg/kg in two breeding lines while resveratrol content of 'Carlos' berries was approximately 10 mg/kg. In a comparison of fungicide sprayed and unsprayed vines [26], the resveratrol content of the skins of unsprayed 'Carlos' berries was 0.33 g/g, 'Noble' was 9.5 g/g, and 'Summit" was 5.8 g/g. Levels of resveratrol reported in this study averaged from 1.8 g/g for 'Carlos' to 14.7 g/g for 'Doreen' and were within the range of that reported in other studies. ...
... Cultivation practices have also been shown to influence resveratrol accumulation in grapevine leaves and fruit. A negative correlation was found between the resveratrol level and the extent of nitrogen fertilisation (Fregoni et al., 2000; Bavaresco et al., 2001) or fungicide spray application (Magee et al., 2002) while increased potassium fertilisation correlated with higher levels of resveratrol (Fregoni et al., 2000). The potential of grapevine cultivars to accumulate resveratrol was positively correlated with their tolerance to Botrytis (Douillet-Breuil et al., 1999), leading to the suggestion that resveratrol production capacity could be used as a criterion in the selection of resistant varieties (Pool et al., 1981; Creasy and Coffee, 1988; Sbaghi et al., 1995). ...
... Several studies did not corroborate a relationship between resveratrol accumulation and disease incidence in grapevine (Magee et al., 2002; Keller et al., 2003). ...
Plants possess a range of tools for combating a Botrytis infection. This chapter will describe three types of pre-formed and induced plant defence compounds and discuss their effectiveness
in restricting Botrytis infection. Case studies are presented on several types of secondary metabolites: stilbenes including resveratrol, saponins
including ??-tomatin, cucurbitacins, proanthocyanidins and tulipalin A. Evidence is presented suggesting that Botrytis species have evolved mechanisms to counteract some of these defence responses. Secondly, we discuss the role of structural
barriers and cell wall modification in preventing penetration. Finally the contribution of PR proteins to resistance is discussed.
... Spraying muscadine grape vines (V. rotundifolia) with commercial synthetic fungicides has been shown to result in much less resveratrol in skins of berries from the plants, presumably because of less fungi to induce production of this phytoalexin [47]. In addition to fungicide treatment, the amounts have been shown to vary considerably with cultivar; the concentrations were found to be higher in grape skins than in seeds, and levels in seeds were higher than in the pulp of the berry. ...
Resveratrol and its dimethoxylated derivative, pterostilbene, are produced by several plant species, including a few edible crops such as peanut (Arachis hypogaea L.), grapes (Vitis spp.), and blueberries (Vaccinium spp.), as well some plants used in traditional medicine. Both compounds are inducible, antimicrobial compounds with activity against both plant pathogenic bacteria and fungi, an activity apparently not directly related to their strong antioxidant activity. An amazing number of nutraceutical properties have been claimed for both compounds, including antioxidant, antiaging, anti-cholesterol, anticancer, antidiabetic and other beneficial activities. Most evidence supports the view that pterostilbene is more active for most of these effects, due in part to its greater biological availability. However, the amount of these compounds in most diets is insufficient to provide these health benefits. Dietary supplements of formulated pure compounds can now provide sufficient dietary levels for these effects, as transgenic crops in the future might also do.
... Sbaghi et al., (1996) ont démontré une corrélation entre la capacité des isolats de B. cinerea à désintoxiquer le resvératrol et leur virulence sur des feuilles de vigne. Cependant, plusieurs études ne confirment pas une relation entre l'accumulation du resvératrol et l'incidence de la maladie chez la vigne (Keller et al., 2003;Magee et al., 2002). Hoos et Blaich (1990), ont montré que l'augmentation de la concentration des conidies dans un milieu synthétique contenant du resvératrol a conduit à une augmentation du catabolisme du resvératrol et en conséquence à la survie des conidies. ...
La pourriture grise, causée par le champignon Botrytis cinerea , est l'une des principales maladies aériennes fongiques sur diverses cultures d’importance agronomique. La diversité génétique de B. cinerea est très forte et la capacité rapide d’adaptation de ce champignon à une pression sélective est également avérée. Ce champignon est ainsi capable de développer des résistances à une grande variété de composés fongicides de synthèse ou d'origine naturelle. Des méthodes alternatives de lutte ont de ce fait été développées ces dernières années : divers agents de lutte biologique (ALB) présentant différents modes d’actions ont été identifiés et pour certains d’entre eux commercialisés pour contrôler B. cinerea . Cependant la durabilité de la lutte biologique est un domaine encore très peu étudié. La perte d'efficacité d'un ALB pourrait résulter de la préexistence d’isolats moins sensibles de pathogènes dans les populations naturelles et/ou de la capacité de l’agent pathogène à produire, sous une pression de sélection continue exercée par l’ALB, des mutants ayant une sensibilité réduite. L'objectif global de la présente étude est d'évaluer le risque potentiel de perte d'efficacité de la lutte biologique vis-à-vis de B. cinerea . Dans cette étude, les efforts ont été concentrés sur la pyrrolnitrine, un antibiotique produit par divers ALBs, dont certains sont efficaces contre B. cinerea . Les objectifs spécifiques de l'étude étaient (i) d’évaluer la diversité de la sensibilité à la pyrrolnitrine au sein de la population naturelle de B. cinerea , (ii) d'estimer le risque de perte d'efficacité des ALBs produisant la pyrrolnitrine due à la pression de sélection exercée par la pyrrolnitrine et (iii) d'étudier le mécanisme de résistance à la pyrrolnitrine chez B. cinerea . Parmi 204 isolats de B. cinerea , une gamme importante de sensibilité à la pyrrolnitrine a été observée, avec un facteur de résistance de 8,4 entre l’isolat le plus sensible et l'isolat le moins sensible. La production de 20 générations successives pour 4 isolats de B. cinerea , sur des doses croissantes de pyrrolnitrine, a abouti au développement de mutants avec des niveaux élevés de résistance à l'antibiotique, et à une réduction in vitro de la sensibilité à la bactérie productrice de pyrrolnitrine Pseudomonas chlororaphis PhZ24. La comparaison entre les mutants résistants à la pyrrolnitrine et leurs parents sensibles pour la croissance mycélienne, la sporulation et l'agressivité sur plantes a révélé que la résistance à la pyrrolnitrine est associée à un fort coût adaptatif. Des observations cytohistologiques sur tomates ont confirmé que l’isolat sensible à la pyrrolnitrine attaque le pétiole rapidement et envahit la tige, alors que le mutant résistant à la pyrrolnitrine ne s'étend pas au-delà du pétiole. De plus, ce dernier mutant forme un mycélium anormal et des cellules ressemblant à des chlamydospores. Les résultats ont d'autre part révélé que les mutants de B. cinerea résistants à la pyrrolnitrine sont résistants au fongicide iprodione, suggérant ainsi qu'une pression exercée par la pyrrolnitrine sur le champignon conduit à une résistance au fongicide. Réciproquement, la production de générations successives sur iprodione conduit à une résistance à l'antibiotique. Afin d'étudier les déterminants moléculaires de la résistance de B. cinerea à la pyrrolnitrine, le gène histidine kinase Bos1, impliqué entre autres dans la résistance aux fongicides chez B. cinerea a été séquencé chez les souches sensibles et les mutants résistants. La comparaison des séquences a mis en évidence des mutations ponctuelles différentes chez les mutants de B. cinerea obtenus sur la pyrrolnitrine et ceux obtenus sur l'iprodione. De plus, les résistances à la pyrrolnitrine et à l'iprodione ne sont pas systématiquement associées à une mutation ponctuelle dans le gène Bos1. Enfin, aucune modification n'a été détectée dans la taille des allèles de neuf locus microsatellites quelle que soit la pression sélective exercée et quelle que soit le phénotype du mutant produit. Cette étude montre qu'un champignon pathogène des plantes est capable de développer progressivement une moindre sensibilité à un agent de lutte biologique mais que cette moindre sensibilité est associée à une forte perte de fitness
... Seasonal changes in resveratrol content were also observed in grape roots, with a higher content (103-123 mg/kg dry weight) in the months of May and August to October, and a lower content (61-93 mg/kg dry weight) in the remaining months of the year [43]. Fungicides and methyl jasmonate treatments can markedly reduce resveratrol content in grapes and strawberry, respectively [44,45]. Taken together, environmental conditions and the stages of plant development affect resveratrol synthesis and content. ...
Protective role of the skin is against external insults and maintenance of electrolyte homeostasis of the body. Cutaneous dysfunction can account for the development of both cutaneous and systemic disorders. Thus, improvements in cutaneous functions can benefit a number of extracutaneous and cutaneous functions. Resveratrol, a natural ingredient, displays multiple benefits for various systems/organs, including the skin. The benefits of resveratrol for cutaneous functions include stimulation of keratinocyte differentiation and antimicrobial peptide expression, inhibition of keratinocyte proliferation and cutaneous inflammation, UV protection, anticancer, antiaging, and inhibition of melanogenesis. The mechanisms of action of resveratrol include activation of sirtuin 1 and nuclear factor erythroid 2-related factor 2, and inhibition of mitogen-activated protein kinase signaling. Evidence suggests that topical resveratrol could be a valuable alternative not only for daily skin care, but also for the prevention and treatment of various cutaneous disorders. This review summarizes the benefits of resveratrol for cutaneous functions.
... No clear relationship between berry color and resveratrol concentrations were found; conversely Ector et al. (1996) found resveratrol to be greater in black genotypes. Magee et al. (2002) found the bronze 'Summit' to have among the highest concentration of resveratrol in a group of both black and bronze genotypes , which is similar to our study. Ector et al. (1996) ...
A major limiting factor in muscadine grape (Vitis rotundifolia) commercialization is deterioration during storage. One solution for extending market seasons and preventing market saturation for fresh muscadines could be the release of new cultivars with improved postharvest storability. The composition attributes and postharvest storability were evaluated on eight muscadine cultivars and nine breeding selection grown at the University of Arkansas Fruit Research Station. The objective of the study was to identify muscadine genotypes with potential for commercialization and postharvest storability. Muscadines were hand-harvested and evaluated weekly for 4 weeks. The initial berry volume among muscadine genotypes ranged from 84.9 to 240.0 cm3, titratable acidity (TA) ranged from 2.1 to 4.8 g/l, pH ranged from 3.1 to 3.9, soluble solids ranged from 16.6% to 27.3%, firmness ranged from 5.9 to 10.4 N, L* value ranged from 27.4 to 96.8, chroma ranged from 2.1 to 18.5, and hue ranged from 5.1 to 311.6. Hue, TA, and pH of the muscadines did not change during storage. However, firmness and berry volume decreased while weight loss and decay increased during storage, but varied by genotype. Due to less decay, less weight loss, and greater firmness during storage, the bronze genotypes AM 03, Summit and the black genotypes AM 28, Southern Jewel, and Supreme had the highest potential for postharvest storage, while the bronze genotypes Fry and Tara and the black genotypes AM 04 and Ison had the least potential. These findings indicated superior postharvest genotypes and aid in providing postharvest handling parameters.
... Resveratrol. Resveratrol concentrations reported in muscadine skins (Magee et al., 2002) and whole berries (Ector et al., 1996) were similar to that of this study. The levels of resveratrol in the seeds, flesh and whole berries among years did not change (Table 1). ...
Fresh-market muscadine (Vitis rotundifolia Michx.) cultivars, such as ‘Supreme’, have reportedly improved
postharvest storability. Physiochemical attributes and nutraceutical compounds in ‘Supreme’ muscadine whole
grape berries and grape segments (flesh [skin and pulp] and seeds) were measured at harvest in 2012 and 2013
and nutraceutical compounds were measured during postharvest storage for 6 weeks at 2°C in 2012. Total anthocyanins, ellagitannins, and flavonols in whole berries and flesh were higher than seeds, while total phenolics and Oxygen Radical Absorbance Capacity (ORAC) were higher in whole berries than the flesh and seeds. Anthocyanins were present in the whole berries and the flesh, but not in the seeds. Total ellagitannins were distributed with 81% in flesh and 19% in seeds. Total flavonols were found 90% in flesh and 10% in seeds and total phenolics were present 55% in flesh and 45% in seeds. In 2012, 48% of ORAC was accounted for in flesh and 52% in seeds, conversely in 2013, 63% was in flesh and 37% in seeds. Resveratrol was almost completely found in flesh (96%) with the remaining 4% in seeds. Postharvest storage did not dramatically impact nutraceutical components in the whole berries or the segments. Total anthocyanins were negatively correlated with total ellagitannins (r = −0.94) and total flavonols (r = −0.88). Total ellagitannins were positively correlated with total flavonols (r = 0.97). ORAC was positively correlated with total phenolics (r = 0.88). Both the discovery that postharvest storage of muscadine grapes did not dramatically impact nutraceutical components in the whole berries or the segments and the identification and quantification of nutraceutical components in berry tissues provides additional information on nutraceuticals in this underutilized fruit.
... No clear relationship between berry color and resveratrol concentrations were found; conversely Ector et al. (1996) found resveratrol to be greater in black genotypes. Magee et al. (2002) found the bronze 'Summit' to have among the highest concentration of resveratrol in a group of both black and bronze genotypes, which is similar to our study. Ector et al. (1996) found that resveratrol concentrations were higher for muscadines compared with V. vinifera table grapes. ...
Muscadine grapes (Vitis rotundifolia Michx.) are native to the southeastern United States and have potential for greater fresh-market sales if postharvest storage can be improved, but limited information is available on postharvest storability. In 2012 and 2013, physiochemical and storability attributes were measured in 17 muscadine genotypes (selections and cultivars) from the muscadine breeding program at the University of Arkansas or commercial cultivars. The postharvest and physiochemical attributes of the muscadines were measured at harvest and during storage for 3 weeks at 2 degrees C. Nutraceutical compounds were measured initially after harvest. As a result of extreme differences in weather in 2012 and 2013, the data were analyzed by year. Genotypes significantly affected storage attributes [weight loss (%), and unmarketable berries (%)] and physiochemical attributes such as penetration force (force to penetrate berry skin), titratable acidity (TA), pH, soluble solids (%), berry color (L*, chroma, and hue) as well as the nutraceutical compounds. The postharvest attributes of weight loss and unmarketable berries and the physiochemical attribute of penetration force were significantly affected by postharvest storage, but berry composition attributes remained fairly constant during storage. Overall, University of Arkansas selections AM 04, AM 26, AM 28, and the cultivar Southern Jewel had the highest potential for postharvest storage, whereas the genotypes AM 01, AM 15, AM 18, and 'Nesbitt' had the least potential. Genotypes AM 03, AM 04, AM 27, and 'Ison' had the highest nutraceutical contents [total anthocyanins, total phenolics, total flavonols, resveratrol, and oxygen radical absorbance capacity (ORAC)], whereas AM 18, AM 28, 'Supreme', and 'Tara' had the lowest contents. Postharvest storage potential, berry composition, berry color, and nutraceutical content were genotype-specific, but commercially viable genotypes were identified that can provide genetic material for breeding programs and postharvest evaluation protocol for commercial use.
... Resveratrol, a phytoalexin, has shown potential value in the prevention and treatment of cardiovascular S. MARÍN ET AL. disease and certain cancer processes. Resveratrol is present in grapes, its concentration in seeds is lower than that in skins, whilst accumulation of resveratrol in juice/pulp was much lower than in skins and seeds (Magee et al., 2002). Resveratrol is produced by grape berries in response to grey mould as a resistance agent. ...
Resveratrol antimycotoxigenic activity was tested against Fusarium verticillioidesand Fusarium graminearum in corn. Both trans-resveratrol and RES VIN® (a commercial lyophilised polyphenolic product obtained from the skins of red wine grapes, which contains a 10.015% resveratrol) were tested for their efficacy to control mycotoxins accumulation in corn. In particular, their effects were tested against fumonisin B1(FB1) and zearalenone (ZEA) accumulation in naturally contaminated corn with additional inocula of toxinogenic isolates of either F. verticillioides or F. graminearum. ZEA accumulation was reduced by 80% in F. graminearum inoculated samples, while no inhibition of FB1 accumulation was observed in any of the treatments tested. Resveratrol has previously shown to have antifungal properties against certain fungal species. Thus, studies are needed using higher resveratrol concentrations in order to achieve wider antimycotoxigenic effect as reported in in vitro studies. Trans-resveratrol and RES VIN® had similar effects in the experiment carried out, suggesting that the use of the sub product of the wine industry could be a good alternative to synthetic resveratrol.
... Assessing severity of disease for many of the root pathogens certainly falls into this category, as does the assessment of virus disease severity in many plants (20,46,49). In these and similar situations, researchers have often used an ordinal scale of measurement (10,21,25,29,42,48,54,56,67). An ordinal scale is one in which the values used for the measurement are interpretable only in terms of their arrangement in a given order, for example, from least to most severe. ...
ABSTRACT Plant disease severity often is assessed using an ordinal rating scale rather than a continuous scale of measurement. Although such data usually should be analyzed with nonparametric methods, and not with the typical parametric techniques (such as analysis of variance), limitations in the statistical methodology available had meant that experimental designs generally could not be more complicated than a one-way layout. Very recent advancements in the theoretical formulation of hypotheses and associated test statistics within a nonparametric framework, together with development of software for implementing the methods, have made it possible for plant pathologists to analyze properly ordinal data from more complicated designs using nonparametric techniques. In this paper, we illustrate the nonparametric analysis of ordinal data obtained from two-way factorial designs, including a repeated measures design, and show how to quantify the effects of experimental factors on ratings through estimated relative marginal effects.
Salvestrols are naturally occurring, metabolically active substances that act as anticancer prodrugs when metabolically activated by the Cytochrome P450 enzyme, CYP1B1. They are phytoalexins and as such are induced in response to pathogens. As phytoalexins they do not fall neatly into any of the classes of phytonutrients. Some are stilbenes, some are antioxidants, some are phytoestrogens while others fall outside of these categories. Salvestrols obtain their anticancer activity not as a member of some phytonutrient class but rather through their metabolism by CYP1B1. Unfortunately, Salvestrols are deficient in western diets due to the modern agricultural practices that minimize the risk of predation through the use of fungicides with the consequence of minimizing the conditions for induction of these compounds. It is in organically grown foods that salvestrol levels are highest. To illustrate the breadth of a nutritional approach to cancer treatment using Salvestrols, cases are presented here that cover stage 1 breast cancer, squamous cell carcinoma of the anus, chronic lymphocytic leukaemia, primary peritoneal carcinoma and a case of benign prostatic hyperplasia. Four of these cases highlight how rapidly one can recover once nutritional deficits are addressed without recourse to conventional treatment.
Resveratrol is well known for its strong antioxidant properties. To accelerate research on resveratrol metabolism and to evaluate the genetic potential for breeding, the stilbenoid contents of four tissues (leaf and berry skin, flesh and seed) were examined in 21 accessions of six wild Chinese grapevine species (Vitis quinquangularis, V. romanetii, V. piasezkii, V. shenxiensis, V. amurensis and V. davidii). Resveratrol derivatives in V. quinquangularis, V. romanetii, V. piasezkii and V. shenxiensis are reported for the first time. Three kinds of stilbenoid (trans-resveratrol, cis-piceid and trans-piceid) were detected in the berry skins, flesh, seeds and leaves but cis-resveratrol was found to be absent. Stilbenoid content was predominantly affected by genetic background and by tissue type. In most accessions, berry skins produced the highest total stilbenoid, followed by leaves, seeds and flesh. As a proportion, cis-piceid was the major stilbenoid component in berry skins, seeds and leaves, whereas trans-piceid was the major component in the flesh.
Stilbenes are secondary metabolites of a class of non-flavanoid phenolics found in certain species of Vitis. This class of compounds includes resveratrol and a resveratrol glucoside called piceid that exists in trans and cis forms. This study was undertaken to determine the cis and trans forms of both resveratrol and piceid in the skin, pulp, seeds, and juice of nine cultivars of muscadine grapes and three cultivars of Vitis labruscana. Juice samples of the muscadine cultivars ‘Fry’, ‘Hunt’, ‘Magnolia’, ‘Watergate’, ‘Carlos’, ‘Noble’, and ‘Sweet Jenny’, and the V. labruscana cultivars ‘Albermarle’, ‘Miss Blanc’, ‘MidSouth’ and ‘Miss Blue’ were harvested at the full ripe stage and divided into two sub-samples. One subsample was used to extract juice and the other was divided into skins, pulp, and seeds. Sample analysis was performed using HPLC with a UV detector. Sample chromatagrams were compared with those of known standards for quantification. ‘Carlos’ and ‘Magnolia’ had the greatest total stilbene concentration in skin tissue and had bronze skin containing higher concentrations of total stilbenes than any of the black-skinned cultivars tested. Only one bronze skin cultivar, ‘Sweet Jenny’, had lower stilbenes than the dark skin cultivars. Piceid, cis piceid and resveratrol were found in the skins of all cultivars. ‘Carlos’ ‘Magnolia’, ‘Fry’ and ‘Albermarle’ muscadines contained cis resveratrol in the skins of the fruit. ‘Watergate’ was the only cultivar in which resveratrol was detected in seed tissue. ‘Sweet Jenny’ had the highest levels of cis piceid in seed tissue. ‘Albermarle’, ‘Carlos’ and ‘Sweet Jenny’ had significantly greater levels of cis picied in pulp tissue than all other cultivars.
Resveratrol, a compound commonly found in red wine, has attracted many attentions recently. It is a diphenolic natural product accumulated in grapes and a few other species under stress conditions. It possesses a special ability to increase the life span of eukaryotic organisms, ranging from yeast, to fruit fly, to obese mouse. The demand for resveratrol as a food and nutrition supplement has increased significantly in recent years. Extensive work has been carried out to increase the production of resveratrol in plants and microbes. In this review, we will discuss the biosynthetic pathway of resveratrol and engineering methods to heterologously express the pathway in various organisms. We will outline the shortcuts and limitations of common engineering efforts. We will also discuss briefly the features and engineering challenges of other longevity boosting compounds.
Recommendations for a healthy or prudent diet include a large number of daily servings of fruits and vegetables, and these 2 classes of food are widely believed to assist in cancer prevention. One potential mechanism that is rarely mentioned in nutritional studies involves the cytochrome P450 enzyme CYP1B1, which appears to have the unique properties of being a universal cancer marker overexpressed in cancer cells and having the capability of converting various phytochemicals and synthetic chemicals into substances cytotoxic to these cells. Although these particular features of CYP1B1 have not gone unnoticed, there has been relatively little research aimed at exploiting them. Furthermore, therapeutic and preventive strategies currently being considered based on vaccines against the enzyme or inhibition without the generation of cytotoxins can be questioned because they do not take advantage of the unique properties of this enzyme. In addition, a few relevant case histories have been published that use specially designed fruit extracts containing substrates with demonstrated cytotoxic metabolic products, and these reports provide an initial confirmation of the potential of exploiting the unusual properties of this enzyme for cancer therapy.
Resveratrol, an interesting plant phenolic compound, is found in red wine but is not widely distributed in other common food sources. Health benefits of resveratrol include prevention of cardiovascular diseases and cancers, and--as discovered more recently--promotion of longevity in several animal systems. The pathway and enzymes for resveratrol biosynthesis are well characterized. Furthermore, metabolic engineering of this compound has been achieved in plants, microbes and animals. This review attempts to summarize current understanding of resveratrol pathway-engineering in various systems, to outline the challenges in commercial applications and to identify future opportunities for resveratrol bioengineering.
The capacity to synthesize the stilbene resveratrol in response to UV irradiation is used as a measure of the phytoalexin production potential of grape berry skin. Greenhouse-grown berries after set, but before maturation, had high phytoalexin potential, whereas buds, flowers, and mature fruits had low potential. Stilbenes were not synthesized in the fleshly part of fruit and were found erratically in small amounts in noninduced berry skin. In field samples, ‘Concord’, ‘Cabernet Sauvigon’, and ‘Catawba’ had high resveratrol production potential whereas ‘White Riesling’, ‘Chancellor’, and ‘Cayuga White’ had low potential. The phytoalexin production potential decreased in all cultivars after late August, independent of their maturity.
At three developmental stages berries of field-grown Castor (interspecific crossing) and Huxelrebe (V. vinifera L. crossing) were in vitro inoculated with two strains of Botrytis cinerea Pers, to investigate the response of berries to fungal infection with respect to the time course of phytoalexin (trans-resveratrol, ε-viniferin and pterostilbene) accumulation and visual disease symptoms. In infected berries the amounts of ε-viniferin dominated over pterostilbene. The stilbene phytoalexin content decreased during berry development and sugar accumulation. Grape varieties reacted differently to B. cinerea strains with regard to stilbene response and visual symptoms. Mechanical damage of the berry skin induced uninfected berries to synthesize low amounts of phytoalexins. It can be assumed that after extraction and degradation ε-viniferin of mature berries is a source of resveratrol in wine.
Resveratrol (trans-3,5,4'-trihydroxystilbene), a grapevine phytoalexin related to grey mold resistance, is produced by grape berries of Vitis vinifera L. and Vitis labrusca L. in response to UV-irradiation; its production decreases during fruit ripening. In vinifera varieties, the resveratrol content of whole berries steadily declined between the green stage and complete maturity, nearing zero in ripe fruit, while a pronounced decrease was observed in the berries of V. labrusca after veraison. On the other hand, resveratrol synthesis was found to be located in the skin, thus showing that the principal resistance of grapes to fungal attacks takes place at this level. Finally, the decrease of resveratrol production during maturation was also confirmed by the fact that there is a clear negative correlation between the resveratrol content of grape skin and the developmental stage of berries measured by the sugar concentration of juice.
Resveratrol is one of the wine components related to moderate wine consumption and reduction of serum cholesterol levels. The standard addition method was used with a high pressure liquid chromatography procedure to calculate resveratrol levels. Grape variety, UV light exposure, enzyme addition, skin contact time, and the fining agents, carbon and PVPP, affected the resveratrol levels of wines from the white varieties, Chardonnay and Chardonel, and the red varieties, Cabernet Sauvignon, Cynthiana, and Noble. UV light exposure of the grape clusters significantly increased the resveratrol level in Cynthiana and Noble wine produced in 1994, but did not yield a consistent result in the other experiments from the 1995 and 1996 wines. Enzyme addition significantly increased resveratrol levels in Chardonnay wine but not Chardonel wine. Skin contact time influenced the extraction of resveratrol from the skin in the red varieties, but the maximum extraction time was dependent on the variety of the grapes. Carbon addition decreased the resveratrol level in Noble wine but not in Cynthiana in the 1994 wines. The addition of PVPP significantly lowered resveratrol level in Chardonel, Chardonnay, Cabernet Sauvignon, Cynthiana, and Noble wine. However, low levels of added PVPP addition did not cause significant loss of resveratrol.
Resveratrol, a phytoalexin found in grapes and other food products, was purified and shown to have cancer chemopreventive activity in assays representing three major stages of carcinogenesis. Resveratrol was found to act as an antioxidant and antimutagen and to induce phase II drug-metabolizing enzymes (anti-initiation activity); it mediated anti-inflammatory effects and inhibited cyclooxygenase and hydroperoxidase functions (antipromotion activity); and it induced human promyelocytic leukemia cell differentiation (antiprogression activity). In addition, it inhibited the development of preneoplastic lesions in carcinogen-treated mouse mammary glands in culture and inhibited tumorigenesis in a mouse skin cancer model. These data suggest that resveratrol, a common constituent of the human diet, merits investigation as a potential cancer chemopreventive agent in humans.
Berry rot diseases of muscadine grapes were monitored throughout the 1991 and 1992 growing seasons on four cultivars (Doreen, Sterling, Carlos, and Cowart) at three locations in south Mississippi. The etiology and symptom development of each berry rot disease were studied. Disease incidence data were collected at 2-wk intervals during both growing seasons. Fruit diseases observed on berries included black rot (Guignardia bidwellii f. muscadinii), bitter rot (Greeneria uvicola), russet (unknown etiology), Macrophoma rot (Botryosphaeria dothidea), and ripe rot (Colletotrichum sp.). Bitter rot was the most important disease in Mississippi, followed closely by black rot. The incidence of Macrophoma rot and ripe rot was low. On leaves, the incidence of black rot was greatest during the middle and late growing seasons. On berries, black rot was most severe as berries approached full size. Cowart and Carlos cultivars were most susceptible to black rot. The incidence of bitter rot on leaves was most severe on young leaves following bud break through the young berry stage. The incidence of bitter rot on berries was severe on small berries, especially those 1 to 3 mm in diameter. The cultivar, Sterling, was most susceptible to bitter rot and russet, but was resistant to black rot. Russet was most severe on full-size berries. G. uvicola was always associated with the russet symptom, and it may be a type of resistance expression by some cultivars to early infection or colonization by this pathogen. Both Colletotrichum acutatum and C. gloeosporioides were identified as causal agents of ripe rot on muscadine grapes in Mississippi.
Levels of trans-resveratrol in commercial red and white Vitis vinifera wines from several regions in Europe, South America, California, and Australia, which were purchased as individual bottles from vendors in this region, were determined using HPLC with electrochemical detection. In addition some white wines prepared in Mississippi from muscadine grapes, Vitis rotundafolia, were also analyzed. HPLC conditions suitable for simultaneous analysis of both trans-resveratrol and free quercetin were developed. Concentration of free quercetin is also reported for many of the wines analyzed. Unlike white V. vinifera wines, white V. rotundafolia wines contain appreciable levels of resveratrol. Measured values ranged from about 0.3 to 1.2 mg/L (ppm), which is similar to resveratrol levels in some red California wines. We are not aware of other analyses of muscadine wines for resveratrol. Highest resveratrol levels were found in a California Barbera (9.2 ppm), California Pinot noir (8.7 ppm), and a French Bordeaux (Merlot/Cabernet Sauvignon blend, 8.3 ppm). Bottles of the same type of wine from different vintners contained widely varying amounts of resveratrol. We also found that levels of resveratrol in multiple bottles of the same wine also varied considerably. Fourteen bottles of a California non vintage blended red wine contained resveratrol levels from 2.74 to 5.77 ppm while eight bottles of a California 1993 Cabernet Sauvignon had levels from 0.46 to 0.74 ppm, nearly the same degree of variation.
The presence of resveratrol has been confirmed in Vitis vinifera and Vitis labrusca grapes and in both red and white wines, but not in the seeds. Since there is a lack of information regarding resveratrol in muscadine grapes (Vitis rotundifolia), two studies were conducted using bronze- and dark-skinned muscadines produced with cultural practices similar to those used in commercial vineyards. The first study determined resveratrol concentrations in the whole berries, berries without seeds, and seeds alone; the second study quantified resveratrol in selected muscadine products including wine, unfiltered juice, pomace, and purees made from pomace. We established that resveratrol is a natural constituent of bronze- dark-skinned muscadine grapes. Dark-skinned muscadine products had higher concentrations of resveratrol than the bronze-skinned counterparts, but there was no significant difference between the two color groups except the pomace. Even though muscadine grape seeds had a higher concentration of resveratrol than the other parts of the berry, the seeds contributed only 30.1% and 23.4% of the total resveratrol in bronze- and dark-skinned berries, respectively. Muscadine wines compared favorably in resveratrol concentration with V. vinifera and V. labrusca wines reported in the literature. The consumption of muscadine products (e.g., wine, unfiltered juice, whole berries without seeds and, especially, products made with muscadine purees) could be a means for incorporating a significant quantity of resveratrol in the average diet.
Resveratrol, a phytoalexin found in grapes and other food products, was purified and shown to have cancer chemopreventive
activity in assays representing three major stages of carcinogenesis. Resveratrol was found to act as an antioxidant and antimutagen
and to induce phase II drug-metabolizing enzymes (anti-initiation activity); it mediated anti-inflammatory effects and inhibited
cyclooxygenase and hydroperoxidase functions (antipromotion activity); and it induced human promyelocytic leukemia cell differentiation
(antiprogression activity). In addition, it inhibited the development of preneoplastic lesions in carcinogen-treated mouse
mammary glands in culture and inhibited tumorigenesis in a mouse skin cancer model. These data suggest that resveratrol, a
common constituent of the human diet, merits investigation as a potential cancer chemopreventive agent in humans.
Resveratrol (3,5,4′-trihydroxystilbene) is one of the stress metabolites produced by grapevines in response to fungal infection or injury. The distribution of this compound in limited lesions caused by Botrytiscinerea on ripe grape clusters in the vineyard has been examined. Resveratrol was present predominantly in the non-infected fruits close to the necrotic area. This localized response can help to arrest the spread of established B. cinerea lesions as long as climatic conditions are unfavourable to the pathogen. When conditions become favorable, i.e. after a mild and humid period rapidly spreading lesions are observed on fruits despite the continued increasing production of resveratrol in the grapes which can reach three- to five-fold the value found before rot intensification. Significant amounts of resveratrol can be found prior to any detectable lesions in fruits collected from apparently healthy clusters thus suggesting that phytoalexin response in initiated soon after the recognition of the pathogen by the plant. The involvement of one or more endogenous signals coming from either the fungus or the plant in the induction of host defence responses has also been discussed.
A study of the effects of some prefermentative and fining practices on the resveratrol concentration in wine was carried
out. The trans- and cis-resveratrol contents in a red wine obtained using must hyperoxidation were reduced to about 50% compared with those of control
wines; this decrease was greater than that observed for total phenols and catechins. In contrast, sparging the red grapes
with SO2 and ascorbic acid before crushing them resulted in the trans-resveratrol concentration being greater than that of the control wines. Moreover the amounts of trans- and cis-resveratrol in commercial and synthetic wines were determined before and after addition of charcol, polyvinylpolypyrrolidone
(PVPP), bentonite, casein, gelatine, and two inert materials, cellulose and diatomaceous earth (kieselgur), used as a filter
aid. The results showed that PVPP, charcoal and casein were more effective at removing trans- and cis-resveratrol both in synthetic wine and in commercial wines. In all the wines tested the other fining agents gave a limited
decrease (2 – 5%) of trans- and cis-resveratrol. After charcoal and PVPP treatments, significant correlations were observed between the percentage of residual
resveratrol and the total phenols in the wines.
Trans-resveratrol (4,3′,5′-trihydroxy stilbene) has been identified as the major component responsible for the blue fluorescence of grapevine leaf tissue following fungal infection or exposure to ultraviolet light. The biosynthesis of this compound appears to be a non-specific response of members of the Vitaceae to infection or injury. The compound is not detectable in healthy leaves but accumulates to between 50 and 400 μg/g fresh weight in infected or u.v.-irradiated leaves and is a major constituent (c. 700 μg/g) of lignified stem tissue. The biological significance of the production of resveratrol is discussed.
Among 17 Vitis spp. tested for Plasmopara viticola resistance, cultivars were selected that allowed no sporulation, limited sporulation, or heavy sporulation of the parasite. With the exception of one group of Vitis spp. which exhibited resistance despite an inability to synthesize high concentrations of stilbene phytoalexins, resistance was positively correlated with the capacity for the synthesis of resveratrol and ε-viniferin following induction by UV irradiation. The necrotic reaction of plant tissue after inoculation was correlated with phytoalexin accumulation rather than with reproduction of Plasmopara viticola.
Leaves of Vitis vinifera cv. Grenache (susceptible), of V. rupestris cv. du Lot (intermediate resistant), and of V. rotundifolia cv. Carlos (resistant) were inoculated with Plasmopara viticola and examined microscopically after staining with a series of reagents. These three species showed, respectively, necrotic spots without sporulation (resistant), diffuse necrosis with limited sporulation (intermediate resistant), and no visible necrosis with heavy sporulation of the parasite (susceptible). In the resistant species, flavonoid compounds were detected in the stomatal cells and the cells around the stomata 2 days after inoculation. In the intermediate resistant species, resveratrol and peroxidase activity were detected 5 days after inoculation, flavonoid compounds were present at 8 days, and lignin was formed in tissue surrounding the necrosis at 15 days. In the susceptible species, only a small amount of yellow autofluorescence was observed in the stomatal cells 8 days after inoculation. These data suggest that the rapidity of flavonoid formation plays an important role in the resistance of V. rotundifolia to P. viticola. The formation of resveratrol, flavonoids and lignin in the intermediate resistant species probably restricts the development of this pathogen.
Resveratrol (3,5,4'-trihydroxy-trans-stilbene), a phytoalexin, is a constituent of the human diet that has been shown to inhibit cellular processes associated with tumor initiation, promotion and progression. In this study, we examined the effect of synthetic resveratrol on the proliferative capacity of immortal and neoplastic human breast epithelial cells in culture. MCF-7, an estrogen receptor-positive breast cancer cell line, MCF-10F, an immortal estrogen receptor-negative breast epithelial cell line, and MDA-MB-231, a malignant estrogen receptor-negative breast epithelial cell line, were treated with 5, 10, 20 or 40 microg/ml resveratrol, and their proliferative activities were determined with the WST-1 colorimetric assay after periods of time ranging from 24 to 144 h of treatment. Our results showed that this phytoalexin inhibited the proliferation of human breast epithelial cells in a dose- and time-dependent manner. Treatment of cells with resveratrol reduced the number of viable cells and prevented the exponential growth of the three cell lines examined. These observations indicate that resveratrol has a direct antiproliferative effect on human breast epithelial cells that is independent of the estrogen receptor status of the cells. Thus, this dietary compound is a potential chemopreventive agent for both hormone responsive and non-responsive breast cancers.
The effects of various stilbenes (i.e, 3,4',5-trihydroxystilbene, 3,4',5-trihydroxystilbene 3-O-D-glucoside and 2,3,4',5-tetrahydroxystilbene 2-O-D-glucoside) isolated from the roots of Polygonum species on rat peritoneal polymorphonuclear leukocyte lipoxygenase and cyclooxygenase activities were studied. Resveratrol (3,4',5-trihydroxystilbene) was found to inhibit the 5-lipoxygenase product, 5-HETE, and cyclooxygenase products, HHT and thromboxane B2; its concentrations for 50% inhibition (IC50) were 2.72 +/- 0.262 microM for the leukocyte lipoxygenase product, 5-HETE, 0.683 +/- 0.163 microM for the formations of HHT and 0.810 +/- 0.274 microM for the formation of thromboxane B2. Piceid (3,4',5-trihydroxystilbene 3-O-D-glucoside) and 2,3,4',5-tetrahydroxystilbene 2-O-D-glucoside also inhibited the formation of 5-HETE, HHT and thromboxane B2, although less strongly. Their IC50 values were, respectively, 55.3 +/- 15.3 microM and greater than 1000 microM for the formation of 5-HETE, 196.7 +/- 48.0 microM and 300.0 +/- 10.4 microM for the formation of HHT and 251.7 +/- 24.9 microM and 366.7 +/- 37.1 microM for the formation of thromboxane B2.
The effects of the roots of Polygonum cuspidatum SIEB. et ZUCC. ("Kojo-kon" or "Itadori-kon" in Japanese) and its stilbene components (resveratrol and piceid) on lipid metabolism in rats and mice (higher animals) were investigated. Resveratrol and piceid inhibited the deposition of triglyceride and cholesterol in the liver of rats fed corn oil-cholesterol-cholic acid mixture. Piceid reduced the serum triglyceride and low density lipoprotein-cholesterol (LDL-ch) levels, and atherogenic index [total cholesterolhigh density lipoprotein-cholesterol (HDL-ch)/HDL-ch] in the oil mixture-fed rats. It was found that intraperitoneal or oral administration of resveratrol or piceid reduced triglyceride synthesis from ¹⁴C-palmitate in the liver of mice. In contrast, these stilbene components did not affect hormone-induced lipolysis in fat cells from rat eqididymal adipose tissue.
A number of lines of evidence suggest that red wine may be more effective than other alcoholic beverages in decreasing the risk of coronary heart disease (CHD) mortality. This protection over and above that due to ethanol itself may be explained by phenolic components with which red wines are richly endowed. We have studied the effects of the trihydroxy stilbene trans-resveratrol on human platelet aggregation and on the synthesis of three eicosanoids from arachidonate by platelets, i.e. thromboxane B2 (TxB2), hydroxyheptadecatrienoate (HHT) and 12-hydroxyeicosatetraenoate (12-HETE). These effects were compared with the actions of other wine phenolics (quercetin, catechin and epicatechin) and antioxidants (alpha-tocopherol, hydroquinone and butylated hydroxytoluene). trans-Resveratrol and quercetin demonstrated a dose-dependent inhibition of both thrombin-induced and ADP-induced platelet aggregation, whereas ethanol inhibited only thrombin-induced aggregation. The other compounds tested were inactive. trans-Resveratrol also inhibited the synthesis of TxB2, HHT, and to a lesser extent 12-HETE, from arachidonate in a dose-dependent manner. Quercetin inhibited only 12-HETE synthesis, and hydroquinone caused slight inhibition of TxB2 synthesis, the remaining compounds being ineffective. De-alcoholized red wines inhibited platelet aggregation; their ability to inhibit the synthesis of TxB2 but not that of 12-HETE from labelled arachidonate by washed human platelets was proportional to their trans-resveratrol concentration. These results are consistent with the notion that trans-resveratrol may contribute to the presumed protective role of red wine against atherosclerosis and CHD.
The phytoalexin production potential of three American Vitis species and that of three cultivars of Vitis vinifera were evaluated in response to UV-C irradiation. Time course changes in resveratrol, piceid, epsilon-viniferin, and pterostilbene contents were studied within 3 days after a short UV-C irradiation. Results show that the two major stilbenes accumulated as a response to UV-C elicitation are resveratrol and epsilon-viniferin, a resveratrol dehydrodimer, the concentration of both compounds usually reaching quantities >100 microgram/g of fresh weight. In contrast, piceid and pterostilbene were constantly produced in low quantities. Owing to the results obtained, the role of stilbene phytoalexins in the resistance of grapevines to diseases is discussed.
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