ArticleLiterature Review

Melatonin in grapes and grape-related foodstuffs: A review

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  • Northwest A&F University, Yangling China
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Abstract

A decade has passed since melatonin was first reported in grapes in 2006. During this time, melatonin has not only been found in the berries of most wine grape (Vitis vinifera L.) cultivars, but also in most grape-related foodstuffs, e.g. wine, grape juice and grape vinegar. In this review, we discuss the melatonin content in grapes and grape-related foodstuffs (especially wine) from previous studies, the physiological function of melatonin in grapes, and the factors contributing to the production of melatonin in grapes and wines. In addition, we identify future research needed to clarify the mechanisms of grape melatonin biosynthesis and regulation, and establish more accurate analysis methods for melatonin in grapes and wines.

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... Beer is part of the usual consumption of a large number of people, and is characterized by having a wide variety of bioactive nutraceutical and phytochemical compounds such as polyphenols and antioxidants [42] presenting B-complex vitamins, ascorbic acid, citric acid, etc. As for the MEL content present in beer, a study of 18 brands of beer present on the market, featuring different alcohol content, showed how all beers featured MEL being directly proportional to the alcohol content at higher MEL content, with values varying from 51.8 ± 2.2 pg/mL-non-alcoholic beer-to 169.7 ± 8.7 pg/mL-beer [44]. ...
... MEL content in different types of wines depending on grape variety, country and harvest. Adapted from Meng et al[42]. ...
Article
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Melatonin is a hormone secreted in the pineal gland with several functions, especially regulation of circadian sleep cycle and the biological processes related to it. This review evaluates the bioavailability of melatonin and resulting metabolites, the presence of melatonin in wine and beer and factors that influence it, and finally the different benefits related to treatment with melatonin. When administered orally, melatonin is mainly absorbed in the rectum and the ileum; it has a half-life of about 0.45–1 h and is extensively inactivated in the liver by phase 2 enzymes. Melatonin (MEL) concentration varies from picograms to ng/mL in fermented beverages such as wine and beer, depending on the fermentation process. These low quantities, within a dietary intake, are enough to reach significant plasma concentrations of melatonin, and are thus able to exert beneficial effects. Melatonin has demonstrated antioxidant, anticarcinogenic, immunomodulatory and neuroprotective actions. These benefits are related to its free radical scavenging properties as well and the direct interaction with melatonin receptors, which are involved in complex intracellular signaling pathways, including inhibition of angiogenesis and cell proliferation, among others. In the present review, the current evidence on the effects of melatonin on different pathophysiological conditions is also discussed.
... Grapes are a highly valuable health-promoting fruit because they contain two kinds of resveratrol and are also high in melatonin [17,20,23]. Several studies have shown that melatonin is present in fresh berries, grape products, such as grape juice and wine, and in other plant organs, including leaves, seeds, flesh and skin [16][17][18][19][20][24][25][26]. Although studies have been conducted to investigate the affect of genotype, developmental stage, agro-meteorological conditions and environmental factors on the melatonin content in grapevine [16,17,19,20,24], the key genes or enzymes of the melatonin biosynthetic pathway in grapevine have not yet been identified. ...
... Several studies have shown that melatonin is present in fresh berries, grape products, such as grape juice and wine, and in other plant organs, including leaves, seeds, flesh and skin [16][17][18][19][20][24][25][26]. Although studies have been conducted to investigate the affect of genotype, developmental stage, agro-meteorological conditions and environmental factors on the melatonin content in grapevine [16,17,19,20,24], the key genes or enzymes of the melatonin biosynthetic pathway in grapevine have not yet been identified. ...
Article
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Background: Melatonin is a ubiquitous molecule and exists across kingdoms. Studies on melatonin in plants have mainly focused on its physiological influence on growth and development, and on its biosynthesis. A number of studies have been conducted on the melatonin content and exogenous melatonin treatment of grapevine (Vitis vinifera L.). However, key genes or enzymes of the melatonin biosynthetic pathway remain unclear. Results: In this study, we cloned and identified the gene encoding serotonin N-acetyltransferase (SNAT) in grapevine (VvSNAT2). The VvSNAT2 protein was identified from a collection of 30 members of the grapevine GCN5-related N-acetyltransferase (GNAT) superfamily. Phylogenetic and protein sublocalization analyses showed that the candidate gene VvGNAT16 is VvSNAT2. Characterization of VvSNAT2 showed that its enzymatic activity is highest at a pH of 8.8 and a temperature of 45 °C. Analysis of enzyme kinetics showed the values of Km and Vmax of VvSNAT2 using serotonin were 392.5 μM and 836 pmol/min/mg protein, respectively. The expression of VvSNAT2 was induced by melatonin treatment and pathogen inoculation. Overexpression of VvSNAT2 in Arabidopsis resulted in greater accumulation of melatonin and chlorophyll and enhanced resistance to powdery mildew in the transgenic plants compared with the wild type (WT). Additionally, our data showed that the marker genes in the salicylic acid (SA) signaling pathway were expressed to higher levels in the transgenic plants compared with the WT. Conclusions: The VvSNAT2 gene was cloned and identified in grapevine for the first time. Our results indicate that VvSNAT2 overexpression activates the SA and JA signaling pathways; however, the SA pathway plays a central role in VvSNAT2-mediated plant defense.
... Other benefits, as described by Meng et al (2017) [5] such as Melatonin, which was recently reported to be present in wine in 2008, as well as resveratrol and hydroxytyrosol, are regarded as bioactive compounds in grapes and wines and have positive effects for human health. ...
... Other benefits, as described by Meng et al (2017) [5] such as Melatonin, which was recently reported to be present in wine in 2008, as well as resveratrol and hydroxytyrosol, are regarded as bioactive compounds in grapes and wines and have positive effects for human health. ...
Conference Paper
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Solar ovens have become a very popular technology for cooking, specially, in underdeveloped countries where access to firewood is scarce, time consuming and expensive. The benefits of solar cooking are multiple, such as saving money, as this device requires no fuel, as well as having an important impact in the environment, decreasing carbon dioxide emissions and decreasing deforestation. One challenge for food industry is to get to know the behaviour of food cooked with solar technology. The aim of this study was to model the drying process of white and red grape in solar oven using thermodynamics and spectrophotometry measurements, controlling the irradiation effect blocking the Ultraviolet radiation using a polarized vinyl film Keywords: sun radiation; thermodynamics; solar oven; drying
... Besides, as the major secretory product synthesized and secreted by the pineal gland, melatonin is also produced in plants where it functions as the first line of defense against oxidative stress (Tan et al. 2014). Since its first discovery in plants in 1995 (Dubbels et al. 1995), melatonin has been identified in many different plants and foods, such as rice (Setyaningsih et al. 2012), orange bell peppers (Huang and Mazza 2011), bread crumb (Kocadağlı et al. 2014), tart cherry, and tomato (Reinholds et al. 2016), particularly grapes and grape-related foodstuffs (e.g., wine, grape juice, and grape vinegar) (Meng et al. 2017;Murch et al. 2010;Tudela et al. 2016). Therefore, human and animals not only can indirect synthesize melatonin from L-tryptophan in the pineal gland by themselves, but also can intake from the daily diet. ...
... Graphene, as a new two-dimensional carbon nanomaterial, attracted considerable attention because of its outstanding physical, chemical, and material properties since it was first introduced in 2004 ( Novoselov et al. 2004). Due to its some intrinsic advantages including ultra-high specific surface area, good chemical and thermal stability, and electron-rich, π-π electrostatic, and hydrophobic properties, graphene was regarded as an excellent adsorbent for cleaning and preconcentration of target analytes (Rao et al. 2009;Liu et al. 2011;Zhang et al. 2017). Moreover, graphene can form a strong π-stacking interaction with the compounds that contained benzene ring because of its large delocalized π-electron system (Dreyer et al. 2010). ...
Article
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In this research, a dispersive solid-phase extraction (dSPE) with graphene oxide@SiO2 (GO@SiO2) nanocomposites as the adsorbent followed by high-performance liquid chromatography analysis was developed for simultaneous determination of melatonin, l-tryptophan, and two l-tryptophan-derived esters in food (black sesame seed (Sesamum indicum L.) was selected in this case). The GO@SiO2 nanocomposite was prepared by one-pot aggregation in aqueous phase with sol-gel technique. The structure and morphology of the GO@SiO2 were characterized by scanning electron microscopy, transmission electron microscopy, Fourier transform-infrared spectroscopy, and X-ray diffraction. The extraction conditions of dSPE including the ratio of material to liquid, adsorption and desorption time, desorption temperature, and desorption solvents were investigated, respectively. The detection limits of the developed method for the analysis of melatonin, l-tryptophan, l-tryptophan methyl ester, and l-tryptophan ethyl ester were achieved below 0.1 μg mL⁻¹. The established method was successfully applied to the analysis of the target analytes in black sesame seed, which provided a simple, low-cost, and sensitive approach for the determination of trace compounds in complex samples.
... Örneğin; sirkadiyen ritim bozukluğu, kronik inflamasyon, oksidatif stres ve uyku eksikliği olarak sıralanabilir. Obezite kaynaklı tahribatı, melatonin hormonunun azalttığı saptanmıştır (Meng, 2017). Günümüzde bireyler geceleri ışık kullanımını artırmış ve vakitlerinin büyük bölümünü kapalı ortamlarda geçirerek vücudun doğal aydınlık-karanlık dengesinde değişime neden olmuşlardır. ...
... Grape pickle is a grape based non-fermented food, produced using Müşküle grape (Vitis vinifera), horseradish (Armoracia rusticana) and boiled grape must. Grape has many benefits to health, it contains several vitamins, minerals, and bioactive compounds such as isoquercetin, catechin and procyanidin B1 (Meng et al., 2017;Toscano et al, 2017). ...
Article
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Grape pickle is a traditional food that is made with grapes (Vitis vinifera), horseradish (Armoracia rusticana) and grape syrup. In this study, the survival of Bacillus cereus and Escherichia coli in grape pickles produced with or without using probiotic Lactobacillus acidophilus La-5 as well as microbiological, chemical and sensory properties of each group were examined during 35 days of ripening at 25°C and 5 months at refrigerated storage period. Molds and lactic acid bacteria (LAB) counts remained below the limit of detection (6 log in samples to be considered a probiotic product. E. coli counts rapidly declined to undetectable level within 7 days, while B. cereus numbers was found 1.56-1.72 log cfu/g at the end of the storage period. As a result, it was established that traditional grape pickle is not suitable food matrix for probiotication. High total soluble solid content (63 °Brix) and presence of horseradish in grape pickles ensure the microbiological stability as well as the safety of product.
... Grape and grape-derived products also contain melatonin [33]. Melatonin, resveratrol and anthocyanins are three of the four most studied natural compounds, in addition to curcumin [34,35]. ...
Article
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Grape (Vitis vinifera L.) is one of the most popular fruits worldwide. It contains various bioactive compounds, such as proanthocyanidins, anthocyanins, flavonols, phenolic acids and stilbenes, the contents of which could vary considerably in grape skin, pulp and seed. Many studies have revealed that grape possesses a variety of health benefits, such as antioxidant, anti-inflammatory, gut-microbiota-modulating, anticancer and cardioprotective effects. Grape is eaten as fresh fruit and is also used as raw material to produce various products, such as wine, grape juice and raisins. Moreover, the byproducts of grape, such as grape pomace and grape seed, have many applications in the food industry. In this paper, the bioactive compounds in grape are briefly summarized based on literature published in recent years. In addition, the health benefits of grape and its bioactive components are discussed, with special attention paid to the underlying mechanisms. Furthermore, the applications of grape in the food industry are elucidated, especially the applications of grape pomace and grape seed. This paper can contribute to understanding the health benefits and mechanisms of grape and its bioactive compounds, as well as the promotion of the use of grape in the food industry.
... These results are consistent with those found in other studies following the application of exogenous melatonin to growing fruit. Thus, treatment of the tree with melatonin increased the fruit weight by 6.6% in grapes [57] and by 47.8% in pears [37]. Increases in fruit number, weight, and size were also obtained in blackberries after melatonin application [38]. ...
Article
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The role of melatonin during the growth and ripening of apple fruit was studied using local varieties. The evolution of the growth and ripening parameters, including fruit size and weight, firmness, color change, sugar content, and ethylene production, was different in the five varieties studied, with yellow apples (Reineta and Golden) initiating the ripening process earlier than reddish ones (Teórica, Sanroqueña, and Caguleira). Changes in the melatonin and melatonin isomer 2 contents during growth and ripening were studied in Golden apples, as was the effect of the melatonin treatment (500 µM, day 124 post-anthesis) on the apple tree. Melatonin content varied greatly, with higher value in the skin than in the flesh. In the skin, melatonin increased at day 132 post-anthesis, when ethylene synthesis started. In the flesh, melatonin levels were high at the beginning of the growth phase and at the end of ripening. Melatonin isomer 2 was also higher once the ripening started and when ethylene began to increase. The melatonin treatment significantly advanced the ethylene production and increased the fruit size, weight, sugar content, and firmness. The data suggest that melatonin stimulates fruit ripening through the induction of ethylene synthesis, while melatonin treatments before ripening improve the final fruit quality.
... Grape berries are a repository of numerous polyphenolic antioxidants, sugars, organic acids, micronutrients, provitamin A, vitamin C and vitamin E . In addition to appealing sensory properties, grapes contain health-promoting substances such as melatonin, resveratrol, and hydroxytyrosol (Meng et al., 2017). Such compounds present in grapes have been associated with lowering the risk of heart attack and blood clots and have also been applied to treating asthma, indigestion, migraine, kidney disease, and fatigue (Singh & Tripathi, 2016). ...
Article
Background Grapes are one of the highly valued non-climacteric fruits that can be consumed fresh or used to produce numerous food products and dietary supplements. Inadvertent fungal infections cause substantial economic and commodity loss in the grape industry. However, control measures have been developed and widely used to combat pathogenic fungal attacks in grapes, most of which are indiscriminate towards the pathogenic fungi. Precise interactions between various pathogenic fungi and grapes have not been fully explored. Scope and approach In the past decade, advanced molecular technics and ‘omics’ approaches have allowed progress to understand such interactions. Discoveries regarding pathogen entry, optimal conditions for pathogenesis, virulence factors, mycotoxin production, fungal genes involved in pathogenesis, quiescent and necrotrophic lifestyles of pathogenic fungi, and grape fruit's response towards the pathogen attack have been published. Key findings and conclusions This review paper summarizes the possible pathways of fungal pathogenesis in grapes and environmental factors influencing fungal infections. We emphasize the molecular aspects of fungal invasions and the transition between quiescent and necrotrophic lifestyles of grape fungal pathogens and the grape's immune response against pathogen attack and genes involved in the defence mechanism. We pinpoint the recent innovations in control strategies and prospective developments in the field. This review aims to reduce the knowledge gap between the fungal disease progression mechanisms and the development of various disease control strategies in grape production.
... Bu durum melatoninin alkolde çözünürlüğü ile açıklanmıştır. Saccharomyces cerevisiae mayasının melatonin sentezinde oldukça önemli olduğu ve şarap üretiminde fermantasyon sırasında kullanılan farklı şarap maya suşlarının da melatonin sentezinde etkili olduğu belirtilmiştir [44,45]. Farklı tür narlardan üretilen şaraplarda melatonin düzeyi de farklı olup 0.54-5.50 ...
... Melatonin also plays a significant role in improving the nutritional properties of fruits. For example, exogenous application of melatonin increased phenolic content and antioxidant activity in grapes (Meng et al., 2017), pomegranate (Jannatizadeh, 2019), jujubes and sweet cherry (Xia et al., 2020) (Table 5). The concentration of cyanin-3-O-glucoside, peonidin derivatives, and two flavanols (e.g., ) reported and explained the effectiveness of melatonin as a postharvest treatment for better quality and delayed senescence in sweet cherries. ...
Article
Background The role of melatonin as a neurotransmitter has been much discussed and studied topic in the animal kingdom but its possible role as a ubiquitous biomolecule with the pleiotropic effect is still at infancy stage in the plant kingdom. Melatonin was just known to be the hormone in the human body which regulates our sleep through its involvement in circadian rhythm or biological clock until its detection in the plant kingdom in the early 90s. Since then, scientists worldwide started working prospectively about its various functions and roles in plants. Now its role in attenuating abiotic and biotic stresses in standing crops has been studied and validated at a commercial level in various cereal and horticultural crops. Food is thy medicine but the abusive use of chemicals rendered them poisonous and consumers being more vigilant and mindful about the food they are consuming are now demanding the chemical free food stuffs. So, in recent years, the trend of using safer alternatives for the control of postharvest diseases of fresh fruits and vegetables have shown a significant increase and hence pressurized the scientists to think about the potential use of melatonin for various postharvest problems. Scope and approach In this review, we have discussed briefly about melatonin's function as potent postharvest treatment for controlling biotic and abiotic stresses and had made an attempt to gather information on its possible roles in postharvest management of fruits and vegetables. Key findings and conclusions Melatonin can be a good alternative to harmful chemicals which are used commercially in postharvest management of fruits. The use of melatonin addresses the major hurdles in postharvest management of fruits such as chilling injury and fruit decay, and it helps in extending the shelf life of fruits and vegetables by delaying ripening and senescence whilst maintaining better fruit quality.
... 63,64 Analysis and identification of melatonin in plants is still worthy of attention due to the structural complexity of melatonin, low abundance, complexity of the plant matrix and the variability in the efficacy of the extraction procedures. Meng et al. (2017) 65 pointed out that chloroform with methanol (30 : 1) or methanol, water, formic acid in a ratio of 80 : 20 : 1 as an extractant when combined with UPLC-MS/MS technology yielded the most consistent results and is the recommended analytical method for the estimation of melatonin concentration in grape berries, while also being suitable for some other plants. Also, samples that are chemically labelled with dansyl chloride (DNS-Cl) coupled with LC-MS are of high sensitivity as well. ...
Article
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In recent years, people have become increasingly interested in bioactive ingredients from plants, especially antioxidant molecules such as melatonin, which are beneficial to human health. The purpose of this article is to provide new information on plant-derived foods with a high content of melatonin. We comprehensively summarize the content of melatonin in plant-derived foods and discuss the factors that influence melatonin levels to provide new ideas on enhancement. Additionally, we describe the biosynthetic pathway of melatonin and identify its major functions. Medicinal herbs are often rich in melatonin while many vegetables and fruits exhibit somewhat lower levels with wide variations among species. The genetic traits of plants, the phenological stage of the cultivar, the photoperiod, the level of stress to which the plants are exposed at the time of harvest, exposure to agrochemicals and determination methods are the main factors affecting the melatonin content. To date, standardization of uniform sampling times and the use of suitable pretreatments as well as determination methods have not been achieved. The results of the studies reviewed highlight the potentially important role of plant melatonin in influencing the progression of human diseases. Based on the health promotional aspects of melatonin, consuming foods containing higher concentrations of tryptophan and melatonin is suggested.
... 32 According to the existing experimental data, HPLC-MS/MS technology is the optimal analytical method for analyzing melatonin levels in wine and it is essential to develop more accurate analysis and detection methods in future studies. 33 The goal of this work is to study the impact of some variable parameters that may occur in the winemaking process on the concentrations of melatonin and its precursors in wines. To accomplish this, a sensitive and selective HPLC-MS/MS method was developed for the simultaneous analysis of melatonin, serotonin, and L-tryptophan in wine samples. ...
Article
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Because melatonin has strong antioxidant activity and wine is an alcoholic beverage of economic relevance, in the present work, the impact of some variable parameters that may occur in the winemaking process on the concentrations of melatonin and its precursors in Romanian wines was studied. Therefore, a sensitive and selective high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed for the simultaneous analysis of melatonin, serotonin, and L-tryptophan, and some method performance parameters including selectivity, detection limit, precision (by comparing with an alternative HPLC-FL method), accuracy, and robustness were validated. These determinations are significant and the final amounts of analytes are dependent on the microorganisms involved in the winemaking process, the grape variety, geographic regions of vineyards, and aging of wines. In the future, the method may be useful to increase the melatonin content and the antioxidant activity in wines by improved steps in the winemaking process, especially based on application of selected yeasts and improved fermentation conditions.
... Büyüme hormonunun (GH) salgılanması hipotalamus tarafından kontrol edilir. Ana işlevi çocuklarda ve ergenlerde büyümeyi teşvik etmektir (Kokkoris ve Pi Sunyer, 2003;Etherton, 2000;Kayaalp, 2009 (Meng, 2017). ...
... Melatonin synthesis is activated by darkness and inhibited by light; thus, this hormone is a key regulator of the circadian network (3)(4)(5)(6)(7). In addition, melatonin is also involved in various physiological processes (i.e., antioxidant activity, bone formation, reproduction, cardiovascular function, and immune regulation) and has been confirmed to have therapeutic effects on gastrointestinal diseases, psychiatric disorders, cardiovascular diseases, and cancers (8)(9)(10). More recently, a few studies have reported that melatonin receptor 1 knockout mice show insulin and leptin resistance (11,12), indicating a role of melatonin and its downstream signals in energy metabolism. ...
Article
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The gut microbiota is strongly shaped by a high-fat diet, and obese humans and animals are characterized by low gut microbial diversity and impaired gut microbiota compositions. Comprehensive data on mammalian gut metagenomes shows gut microbiota exhibit circadian rhythms, which is disturbed by a high-fat diet. On the other hand, melatonin is a natural and ubiquitous molecule showing multiple mechanisms of regulating the circadian clock and lipid metabolism, while the role of melatonin in the regulation of the diurnal patterns of gut microbial structure and function in obese animals is not yet known. This study delineates an intricate picture of melatonin-gut microbiota circadian rhythms and may provide insight for obesity intervention.
... Nonetheless, with relatively few studies-on a limited selection of whole foods-conducted to date, further research is warranted. For example, melatonin and polyphenols such as resveratrol are also found in grape products, mainly in the skin (and to a lesser extent in the seed and whole berry) [60], which may provide an avenue for potential future research directions. ...
Article
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Many processes are involved in sleep regulation, including the ingestion of nutrients, suggesting a link between diet and sleep. Aside from studies investigating the effects of tryptophan, previous research on sleep and diet has primarily focused on the effects of sleep deprivation or sleep restriction on diet. Furthermore, previous reviews have included subjects with clinically diagnosed sleep-related disorders. The current narrative review aimed to clarify findings on sleep-promoting foods and outline the effects of diet on sleep in otherwise healthy adults. A search was undertaken in August 2019 from the Cochrane, MEDLINE (PubMed), and CINAHL databases using the population, intervention, control, outcome (PICO) method. Eligible studies were classified based on emerging themes and reviewed using narrative synthesis. Four themes emerged: tryptophan consumption and tryptophan depletion, dietary supplements, food items, and macronutrients. High carbohydrate diets, and foods containing tryptophan, melatonin, and phytonutrients (e.g., cherries), were linked to improved sleep outcomes. The authors posit that these effects may be due in part to dietary influences on serotonin and melatonin activity.
... Melatonin has been found in noteworthy concentrations in teas and herbal infusions [14], and other foodstuffs such as grapes [15], olive oil, cereals, fruits, nuts [16], and legumes [17]. Fermentation food processes increase melatonin concentration, as shown in beer and wine, among others [18]. ...
Article
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Melatonin is a multifunctional antioxidant neurohormone found in plant foods such as lentil sprouts. We aim to evaluate the effect of lentil sprout intake on the plasmatic levels of melatonin and metabolically related compounds (plasmatic serotonin and urinary 6-sulfatoxymelatonin), total phenolic compounds, and plasmatic antioxidant status, and compare it with synthetic melatonin. The germination of lentils increases the content of melatonin. However, the phenolic content diminished due to the loss of phenolic acids and flavan-3-ols. The flavonol content remained unaltered, being the main phenolic family in lentil sprouts, primarily composed of kaempferol glycosides. Sprague Dawley rats were used to investigate the pharmacokinetic profile of melatonin after oral administration of a lentil sprout extract and to evaluate plasma and urine melatonin and related biomarkers and antioxidant capacity. Melatonin showed maximum concentration (45.4 pg/mL) 90 min after lentil sprout administration. The plasmatic melatonin levels increased after lentil sprout intake (70%, p < 0.05) with respect to the control, 1.2-fold more than after synthetic melatonin ingestion. These increments correlated with urinary 6-sulfatoxymelatonin content (p < 0.05), a key biomarker of plasmatic melatonin. Nonetheless, the phenolic compound content did not exhibit any significant variation. Plasmatic antioxidant status increased in the antioxidant capacity upon both lentil sprout and synthetic melatonin administration. For the first time, we investigated the bioavailability of melatonin from lentil sprouts and its role in plasmatic antioxidant status. We concluded that their intake could increase melatonin plasmatic concentration and attenuate plasmatic oxidative stress.
... Melatonin is also produced in other tissues or organs including the gut, ovary, testes, and retina (42)(43)(44). In addition, melatonin is found in herbs, olive oil, vegetables, fruits, and red wine (43,(45)(46)(47)(48). Multiple physiological functions of melatonin have been reported, including circadian and seasonal rhythms (49), antioxidant (50)(51)(52) and anti-inflammatory properties (39,(53)(54)(55), tumor growth inhibition (56)(57)(58)(59)(60), tissue repair and regeneration (61)(62)(63), and metabolism (43,(64)(65)(66). ...
Article
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The high prevalence of obesity and its associated metabolic diseases has heightened the importance of understanding control of adipose tissue development and energy metabolism. In mammals, 3 types of adipocytes with different characteristics and origins have been identified: white, brown, and beige. Beige and brown adipocytes contain numerous mitochondria and have the capability to burn energy and counteract obesity, while white adipocytes store energy and are closely associated with metabolic disorders and obesity. Thus, regulation of the development and function of different adipocytes is important for controlling energy balance and combating obesity and related metabolic disorders. Melatonin is a neurohormone, which plays multiple roles in regulating inflammation, blood pressure, insulin actions, and energy metabolism. This article summarizes and discusses the role of melatonin in white, beige, and brown adipocytes, especially in affecting adipogenesis, inducing beige formation or white adipose tissue browning, enhancing brown adipose tissue mass and activities, improving anti-inflammatory and antioxidative effects, regulating adipokine secretion, and preventing body weight gain. Based on the current findings, melatonin is a potential therapeutic agent to control energy metabolism, adipogenesis, fat deposition, adiposity, and related metabolic diseases.
... It is known that Mel is produced by yeasts during alcoholic fermentation and this production depends on the medium, mainly the L-Trp and sugar concentrations, and also the growth phase, 9,11,[29][30][31] among others conditions. However, the biosynthetic pathway of Mel and other ICs is completely unknown in yeasts. ...
Article
Melatonin (Mel), originally considered a neurohormone, has been detected in beverages and food‐fermented products in which yeast metabolism is highly important. This indolamine is synthesized from serotonin, with L‐tryptophan being the initial substrate of both. Regarding Mel metabolism, the biosynthetic pathway in mammals consists in four‐step reactions. However, six genes are implicated in the synthesis of Mel in plants, which suggest the presence of many pathways. The aim of this study is to provide new empirical data on the production of Mel and other indole‐related compounds in the yeast Saccharomyces cerevisiae (S. cerevisiae). To this end, we performed the addition of the pathway intermediates in S. cerevisiae cells in different growth stages (exponential and arrested cells) to follow the bioconversion and new indolic compound production from them. The different bioconverted indolic compounds tested (L‐tryptophan, 5‐hydroxytryptophan, tryptamine, serotonin, N‐acetylserotonin, 5‐metoxytryptamine and Mel) were analyzed by UHPLC‐MS/MS from the extra‐ and intracellular contents. Our results showed that serotonin, in yeast, was prevalently formed via tryptophan decarboxylation, followed by tryptamine hydroxylation as in plants. Mel production from serotonin can be achieved by either N‐acetylation, followed by O‐methylation or O‐methylation, in turn followed by N‐acetylation. Accordingly, the classic pathway of Mel synthesis in vertebrates does not seems prevalent in yeast. This article is protected by copyright. All rights reserved.
... Fig. 1 shows a scheme of the wine production process integrated with the biodiesel production process proposed in this work. The grape seeds oil studied in this work has also nutraceutical components like resveratrol and melatonin [7] that would thus fulfil the biorefinery concept, that is, a refinery that produces not only biofuels but also other high added value compounds like monomers and nutraceuticals. ...
Article
Residues from wine industry constitute an interesting feedstock for biodiesel in wine-producing countries like Spain. The use of grape seed oil together with bioethanol obtained from wine surplus or distillation of grape skins and stalks in the transesterification reaction results in fatty acid ethyl esters (FAEE), which is a fully renewable and waste-derived biofuel. In this work, FAEE from the grape seed oil obtained from the vine variety Tempranillo has been produced and some of their properties have been measured and estimated. Only the oxidation stability would fall below the minimum value established for biodiesel in Europe, thus requiring additivation with antioxidants to fulfill the standard. The remaining properties are within the range. Noteworthy, the cold flow behaviour is very promising.
... Chronic and moderate consumption of red wine is associated with a reduced risk of CVDs and other diseases such as diabetes and neurological diseases (Opie and Lecour, 2007). Melatonin is present in grapes and wines; and consumption of grape products may affect endogenous melatonin levels (Iriti, 2009;Murch et al., 2010;Meng et al., 2017a). In young, middle-aged and elderly individuals, intake of 200 mL of grape juice twice a day significantly increases urinary 6-sulfatoxymelatonin and total antioxidant capacity (Gonzalez-Flores et al., 2012). ...
Article
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The role of the diet as well as the impact of the dietary habits on human health and disease is well established. Apart from its sleep regulatory effect, the indoleamine melatonin is a well-established antioxidant molecule with multiple health benefits. Convincing evidence supports the presence of melatonin in plants and foods with the intake of such foods affecting circulating melatonin levels in humans. While numerous actions of both endogenous melatonin and melatonin supplementation are well described, little is known about the influence of the dietary melatonin intake on human health. In the present review, evidence for the cardiovascular health benefits of melatonin supplementation and the dietary melatonin is discussed. Current knowledge on the biological significance as well as the underlying physiological mechanism of action of the dietary melatonin is also summarized. Whether dietary melatonin constitutes an alternative preventive treatment for cardiovascular disease is addressed.
... Melatonin was first identified in plants in 1995; thereafter, it was found that melatonin existed in variety of plants and plant products [13][14][15][16][17][18]. In 2013, we firstly reported that melatonin was also present in apple fruit [19]. ...
Article
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Synthetic melatonin (N-acetyl-5-methoxytryptamine, MT) is popular in the US and Asian markets as a health supplement. Here, we identified a naturally occurring melatonin source in apple juice. Melatonin was present in all 18 apple cultivars tested. The highest melatonin level of the edible part of apple was detected in the apple peel. The melatonin content in 'Fuji' apple juice is comparable to the level of its flesh. Melatonin was consumed during the process of juicing due to its interaction with the oxidants. Melatonin addition significantly reduced the juice color change to brown (browning). The mechanism is that melatonin scavenges the free radicals, which was indicated by the ASBT analysis; therefore, inhibiting the conversion ofo-diphenolic compounds into quinones. Most importantly, melatonin exhibited powerful anti-microorganism activity in juice. The exact mechanisms of this action are currently unknown. These effects of melatonin can preserve the quality and prolong the shelf life of apple juice. The results provide valuable information regarding commerciall apple juice processing and storage.
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Bioactive amines present in grapes and their derivatives are used as quality markers and have important physiological functions in plants and humans. We quantified the biogenic amines and antioxidant activity in whole juices of Vitis labrusca and hybrid grapes developed in Brazil. The grapes used were V. labrusca (‘Bordô’ and ‘Isabel’) and Brazilian hybrids (‘IAC 138–22 Maximo’ and ‘BRS Violeta’) grafted onto ‘IAC 766 Campinas’ rootstock. All vines were trained in low and high vertical shoot positions. The training systems and genotypes used were highly related to the presence of amino compounds and antioxidants. The juices from ‘Bordô’, ‘IAC 138–22 Maximo’ and ‘BRS Violeta’ grapes presented higher contents of beneficial biogenic amines. All juices contained biogenic amines at considerable levels and, consequently, had high biological potential. A high vertical shoot position system is recommended to improve dopamine, melatonin, and serotonin levels.
Chapter
Melatonin is a neurohormone produced and released by the pineal gland. Neurons placed in the eye surface send a signal when the person is exposed to darkness to the suprachiasmatic nuclei and that prompts melatonin release. This biomolecule is in charge of synchronizing body circadian rhythms such as sleep or hunger. Intense light exposure can avoid its release or healthy rhythm. Apart from that, the scientific literature has suggested that melatonin influences immune system, antioxidant capacity, or cell preservation. Moreover, melatonin can be supplied by dietary food such as grapes, dairy or fermented products. Interestingly, some foods contain a significant amount of melatonin and can be considered as good sources of that bioactive molecule. The information in this chapter will cover melatonin dietary sources, biological capacity, related metabolites, and proven benefits in the human body.
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Two lactic acid bacteria (LAB) strains of Lactobacillus plantarum 21802 and Lactobacillus brevis 6239 were selected and combined for fermentation of grape juice. The changes of sugars, organic acids, volatiles, phenolic compounds as well as antioxidant capacity of the grape juice were characterized. Results showed that fermentation with LAB led to a slight decrease in sugar content and increased in organic acid content. The sugars were mainly consumed at the initial stage of fermentation, while the malic acid was consumed completely during the fermentation. The contents of total phenolics and flavonoids in grape juice decreased gradually during the fermentation process. As compared with the initial contents in unfermented grape juice, the contents of proanthocyanin B2, rutin, isoquercitrin, rhamnose-3-O-glucoside in the final fermented grape juice were increased by 26.83%, 249.24%, 138.48%, 139.60%, respectively, while the contents of gallic acid, proanthocyanin B1, catechin and epicatechin were decreased by 24.49%, 14.85%, 71.68%, 42.52%, respectively. The mice fed with the fermented grape juice showed higher activity of superoxide dismutase and lower level of malondialdehyde both in serum and liver tissue than those fed with the unfermented grape juice. Fermentation with LAB also enhanced the flavor profile by increasing the total number and content of volatile compounds, especially those of monoterpene alcohols, which are the main and characteristic aroma volatile compounds in Muscat aroma grapes. This research confirmed that fermentation with LAB might be a desirable option for improving the flavor and nutritional attributes of grape juice by altering the ratio of sugar to organic acid, improving the phenolic compounds, enhancing the antioxidant capacity, intensifying of the characteristic aroma and pleasant flavor of the grape juice.
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The discovery of melatonin (Mel) in wines triggered a new interest in the paradigm of health benefits and wine consumption, usually ascribed to trans-resveratrol (trans-RSV). In this context, a dispersive liquid–liquid microextraction for the analysis of Mel and trans-RSV in wines by LC-FLD was developed. A 2⁶⁻¹ factorial design was used to identify the significant variables (p < 0.05) and Central Composite Design was used to achieve the optimal conditions: 300 µL of chloroform (extracting solvent), 1500 µL of acetonitrile (disperser solvent) and 1500 mg of NaCl (ionic strength). Excellent linearity (R² > 0.9999), repeatability (<3.55%), and accuracy (<7.18%) were obtained using a blank matrix and recoveries (>91.9%) using wines. The method was successfully applied to the analyses of Mel (0.63–7.44 ng mL⁻¹) and trans-RSV (169–2616 ng mL⁻¹) in different wine varieties. Comparison with literature point the overall advantages of the new method.
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This work evaluated the effect of grape juice, red wine and resveratrol in liver parameters of rats submitted to high-fat diet. Experimental model was conducted with groups of adult females Rattus norvegicus: control (CG); high-fat (HG); grape juice (JG); red wine (RW) and resveratrol solution (RG). The high-fat diet significantly altered hepatocytes and Kupffer cells in all treated groups. HG group presented severe steatosis followed hepatocyte ballooning and tissue damages. JG group minimized hepatic histological lesion caused by high-fat diet and WG group also induced steatosis and inflammation in hepatocytes, similar to HG. Still, resveratrol protected the tissue against fatty liver disease by reducing fat infiltration and inflammation, indicating possible therapeutic effects on the liver. Cell cycle analysis showed that HG promoted damage to the tissue, reducing the viable cell content and increasing apoptosis, even when associated with wine consumption or isolated resveratrol. However, JG protected the liver against cell damage generated by the diet. Consumption of grape juice, even associated with a high-fat diet, represents a promising protection of the liver against cellular damage, but red wine further affects the tissue, and resveratrol alone was able to reduce damage but did not minimize cellular damage to the liver.
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This review concerns the current knowledge of melatonin and alcohol-related disorders. Chronobiological effects of ethanol are related to melatonin suppression and in relation to inflammation, stress, free radical scavenging, autophagy and cancer risk. It is postulated that both alcohol- and inflammation-induced production of reactive oxygen species (ROS) alters cell membrane properties leading to tissue dysfunction and, subsequent further ROS production. Lysosomal enzymes are often used to assess the relationships between intensified inflammation states caused by alcohol abuse and oxidative stress as well as level of tissue damage estimated by the increased release of cellular enzymes into the extracellular space. Studies have established a link between alcoholism and desynchronosis (circadian disruption). Desynchronosis results from the disorganization of the body’s circadian time structure and is an aspect of the pathology of chronic alcohol intoxication. The inflammatory conditions and the activity of lysosomal enzymes in acute alcohol poisoning or chronic alcohol-dependent diseases are in most cases interrelated. Inflammation can increase the activity of lysosomal enzymes, which can be regarded as a marker of lysosomal dysfunction and abnormal cellular integrity. Studies show alcohol toxicity is modulated by the melatonin (Mel) circadian rhythm. This hormone, produced by the pineal gland, is the main regulator of 24 h (sleep-wake cycle) and seasonal biorhythms. Mel exhibits antioxidant properties and may be useful in the prevention of oxidative stress reactions known to be responsible for alcohol-related diseases. Naturally produced Mel and exogenous sources in food can act in free radical reactions and activate the endogenous defense system. Mel plays an important role in the normalization of the post-stress state by its influence on neurotransmitter systems and the synchronization of circadian rhythms. Acting simultaneously on the neuroendocrine and immune systems, Mel optimizes homeostasis and provides protection against stress. Abbreviations: ROS, reactive oxygen species; Mel, melatonin; SRV, resveratrol; NF-κB, nuclear factor kappa-light-chain-enhancer of activated B cells; ANT, arylalkylamine-N-acetyltransferase; EC cells, gastrointestinal enterochromaffin cells; MT1, melatonin high-affinity nanomolecular receptor site; MT2, melatonin low-affinity nanomolecular receptor site; ROR/RZR, orphan nuclear retinoid receptors; SOD, superoxide dismutase; CAT, catalase; GPx, glutathione peroxidase; GR, glutathione reductase; GSH, reduced form of glutathione; GSSG, oxidized form of glutathione; TAC, total antioxidant capacity; ONOO∙–, peroxynitrite radical; NCAM, neural cell adhesion molecules; LPO, lipid peroxidation; α-KG, α-ketoglutarate, HIF-1α, Hypoxia-inducible factor 1-α, IL-2, interleukin-2; HPA axis, hypothalamic-pituitary-adrenal axis; Tph1, tryptophan hydroxylase 1; AA-NAT, arylalkylamine-N-acetyltransferase; AS-MT, acetylserotonin O-methyltransferase; NAG, N-acetyl-beta-D-glucosaminidase; HBA1c glycated hemoglobin; LPS, lipopolysaccharide; AAP, alanyl-aminopeptidase; β-GR, β-glucuronidase; β-GD, β-galactosidase; LAP, leucine aminopeptidase.
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The study of biologically important Cu2+ and S2− ions has drawn great attention in the recent years since an abnormal level of these ions is an indication for health impairment. Therefore, a reliable strategy for effective fluorescence determination of Cu2+ and S2− ions was developed. Simply, the method based on economical plant-dependent thermolysis procedure for efficient green synthesis of water dispersible luminescent polyamine-based carbon dots (PA@C-dots) utilizes Vitis vinifera juice as precursor with a high quantum yield (32.1%) and good photo-stability. The fluorescent PA@C-dots were characterized by different spectroscopical, physical, and structural techniques. Furthermore, the synthesized PA@C-dots can be used as an efficient dual functional fluorescent probe for the sensitive and selective estimation of Cu2+ and S2− ions. The incorporation of Cu2+ ions and their adsorption on the surface of PA@C-dot skeleton leads to the respectable fluorescence quenching of C-dots (turn-off mode). The Cu2+-PA@C-dot was found to be sensitive to S2− ions. The addition of S2− recovers the fluorescence (turn-on mode) of Cu2+-PA@C-dots, thanks to its capacity for withdrawing Cu2+ from the shell of PA@C-dots. Fluorescence quenching in the range of 0.07–60 μM Cu2+ was obtained with LOD and LOQ of 0.02 and 0.066 μM, respectively. Sulfide detection provides linearity in the range of 0.8 to 95 μM with LOD and LOQ of 0.24 and 0.79 μM, respectively. The optimal excitation and emission wavelengths for all experiments are 435 nm and 498 nm, respectively. Experiment results elucidate that the proposed method is suitable for Cu2+and S2− ion detection in environmental water samples. Green synthesis of polyamine-functionalized nanoprobe by thermolysis method from plant source as bifunctional sensing platform for determination of Cu2+ and S2− in environmental water samples
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In the current era, the consumption and utilization of fruits and vegetables is gaining significant importance as an effective tool to maintain human health. In this context, phytochemicals and bioactive molecules from fruits and vegetables are also becoming chemo-preventive agent against various maladies. Among these, persimmon (Diospyros kaki L.) fruit belongs to the family Ebenaceae and is used as a medicinal plant since many years to cure different human disorders, such as cancer, diabetes, cardiovascular, obesity, and so on. Persimmon fruit has significant protective effects against various types of human syndromes. Their effectual role is mainly owing to the presence of significant amounts of antioxidants such as phenolic acids, flavonoids, anthocyanins, vitamins, and other phenolic 268compounds. These bioactive compounds have the potential to scavenge and neutralize the free radical chain reaction before causing any deleterious effects to the body. Research-based evidences strongly assert that application of persimmon ingredients provides protection against hyper-lipidemia and hyperglycemia. Conclusively, persimmon and its components have potential as one of the effective modules in diet-based therapy.
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Malolactic fermentation (MLF) in Valtellina Superiore DOCG red wine was monitored in 4 cellars and the final products were analysed to determine the content of melatonin (MEL) and other tryptophan (TRP) derivatives, including tryptophan ethyl ester (TEE) and MEL isomers (MISs), and to isolate predominant O. oeni strains. MEL and TEE significantly increased in wines after MLF from two cellars out of four. Six strains were isolated during the MLF of red wines and under laboratory scale, in rich and synthetic wine cultural media, together with other four O. oeni strains able to trigger the MLF. Results showed that the presence of stressful growth factors, like ethanol and acid pH, has a pivotal role in triggering the release of TEE by oenococci. Indeed, all the strains became capable to produce also MEL and MISs, together with TEE. under harsh growth conditions, as in a synthetic wine medium. The production of these compounds was strain-dependent and a maximum amount of 0.0078 ± 0.0023 ngT/mL (UMB472) and 619.85 ± 196.16 ngT/mL (UMB436) of MEL and TEE was obtained, respectively. In particular, different MISs were detected under oenological and laboratory scale suggesting that other factors (i.e. technological and/or physico-chemical) could affect the synthesis of TRP derivatives.
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Background: Grape is an important fruit consumed either freshly or processed, therefore, fungicide misuse for grape has become an issue of global food safety and human health. Pyraclostrobin, and cyazofamid have been applied to grape frequently. Results: Here a simple QuEChERS (quick, easy, cheap, effective, rugged, and safe) liquid chromatography mass spectrometry has been developed and validated for the determination of pyraclostrobin, cyazofamid and its metabolite CCIM in open field grape samples. The recoveries of those three in the range of 0.01-5 mg kg-1 (n=5) ranged from 73.1-97.9 %. The relative standard deviations (RSDs) were below 12 % for all the cases. The limits of quantitation of each analyte was 0.005 mg kg-1 , which was lower than maximum residue limits of not only pyraclostrobin but also cyazofamid. Not only dissipation kinetics but also residue determination was obtained in grape for those three pesticides. Besides, their half-lives in grape were 10.7-30.1 d, recommending the pre-harvest intervals for these three of 14 d. The calculated hazard quotient and acute hazard index lower than 100% illustrated the safety of intake of grape for Chinese population for not only long-term but also short-term dietary risk assessment. Conslusions: The less than 30 d of half-life illustrated that pyraclostrobin and cyazofamid could degrade relatively easily in environment. The long-term and short-term dietary risk assessment also illustrated the intake safety of these three. Thus, 14 d of pre-harvest interval was safe and recommended. The results of this study contributed to environmental protection, food safety and human health. This article is protected by copyright. All rights reserved.
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Vitis labrusca L. grape (Isabella Grape) is among the grape types that are consumed frequently in the world. Dry fruits are used frequently as snacks for people who work hard and in diet especially during the recent years compared to wet fruits. In this study, the drying characteristics of Vitis labrusca L. are investigated with using different microwave power levels. Mathematical modeling of drying is studied by using the drying models frequently used in the literature. By using spherical coordinates effective moisture diffusion coefficients and activation energy are calculated. Vitis labrusca L. are dried at 20, 6 and 2 minutes with 90, 180 and 360 W power levels, respectively. The best drying model was determined as Alibas and R2, , and root mean square error (RMSE) values were calculated between 0.999398 - 0.999715, 0.000182 - 0.000169, 0.010589 - 0.008675 respectively. Vitis labrusca L. are generally dried in a falling- rate period. Effective moisture diffusion coefficients were calculated between 2.11×10-7 - 6.61×10-8 m2/s and the activation energy were calculated as 75.464 kW/kg. Energy consumption values were determined as 108, 64.8 ve 43.2 kJ at the microwave power levels of 90, 180 and 360 W, respectively.
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The Mediterranean diet is defined as the way of eating based on the traditional foods and drinks of the countries surrounding the Mediterranean Sea. The beneficial health effect of the Mediterranean diet is generally attributed to the rich phytochemical content, high amount of dietary fiber and fermented foods of this diet. In addition to all these bio actives, the Mediterranean diet is also prominent with the presence of melatonin. An essential amino acid, tryptophan, is the precursor of melatonin. Melatonin has a positive effect on health due to its antioxidant, anti-inflammatory, anticancer properties as well as the healing effect on cardiovascular diseases and responsibility for the circadian rhythm in the body. Consumption of foods containing melatonin significantly increases the serum melatonin concentration. Therefore, maximum health benefits are expected with the consumption of foods in the Mediterranean diet, not only their polyphenols and bioactive compounds but also synergistic effects among the polyphenols, bio actives and melatonin. This article will review foods in the Mediterranean diet, their melatonin contents and their expected health benefits.
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This paper analyses changes to ecosystem services (ESS) over the past thirty years in a small part of the hinterland of Xi'an, a city of nearly nine million population in Shaanxi Province, China. Using field survey and interviews with local farmers, the study provides micro-scale exemplification of the transformation occurring around major urban growth centres in China in response both to urbanization and agricultural modernization. The effects of urban growth upon agriculture are illustrated by wholesale changes in the type of production, increasing the value of provisioning services by replacing traditional cereals cultivation with fruit, which reflects the impact of the dynamic urban market. Five different types of ESS are calculated and analyzed, taking into consideration changing land management practices associated with the principal new crops in the study area, cherries and grapes. The widespread adoption of cherries as the main cash crop has also afforded farmers an additional source of revenue from tourists visiting the area to see the Spring-time blossom, pick the fruit and obtain a ‘rural experience’ by interacting with farmers and eating local food. The increased wealth for farm households has prevented the ‘hollowing’ of villages close to the expanding metropolitan area, but longer distance commuting to work in the city is now common for younger rural residents. Detailed calculation of the changing pattern of EES reveals the significant effects not only of the introduction of new crops but also the role of particular land management practices. Further analysis of these practices is proposed to obtain better understanding of the balance between positive and negative changes to EES.
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Melatonin is a pleiotropic signaling molecule that provides physiological protection against diverse environmental stresses in plants. Nonetheless, the mechanisms for melatonin-mediated thermotolerance remain largely unknown. Here we report that endogenous melatonin levels increased with a rise in ambient temperature and that peaked at 40 °C. Foliar pretreatment with an optimal dose of melatonin (10 μM) or the overexpression of N-acetylserotonin methyltransferase (ASMT) gene effectively ameliorated heat-induced photoinhibition and electrolyte leakage in tomato plants. Both exogenous melatonin treatment and endogenous melatonin manipulation by overexpression of ASMT decreased the levels of insoluble and ubiquitinated proteins, but enhanced the expression of heat shock proteins (HSPs) to refold denatured and unfolded proteins under heat stress. Meanwhile, melatonin also induced expression of several ATG genes and formation of autophagosomes to degrade aggregated proteins under the same stress. Proteomic profile analyses revealed that protein aggregates for a large number of biological processes accumulated in wild-type plants. However, exogenous melatonin treatment or overexpression of ASMT, reduced the accumulation of aggregated proteins. Aggegation responsive proteins such as HSP70 and Rubisco activase were preferentially accumulated and ubiquitinated in wild-type plants under heat stress, whilst melatonin mitigated heat stress-induced accumulation and ubiquitination of aggregated proteins. These results suggest that melatonin promotes cellular protein protection through induction of HSPs and autophagy to refold or degrade denatured proteins under heat stress in tomato plants. This article is protected by copyright. All rights reserved.
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Melatonin is a natural mammalian hormone that plays an important role in regulating the circadian cycle in humans. It is a clinically effective drug exhibiting positive effects as a sleep aid and a powerful antioxidant used as a dietary supplement. Commercial melatonin production is predominantly performed by complex chemical synthesis. In this study, we demonstrate microbial production of melatonin and related compounds, such as serotonin and N-acetylserotonin. We generated Saccharomyces cerevisiae strains that comprise heterologous genes encoding one or more variants of an L-tryptophan hydroxylase, a 5-hydroxy-L-tryptophan decarboxylase, a serotonin acetyltransferase, an acetylserotonin O-methyltransferase, and means for providing the cofactor tetrahydrobiopterin via heterologous biosynthesis and recycling pathways. We thereby achieved de novo melatonin biosynthesis from glucose. We furthermore accomplished increased product titers by altering expression levels of selected pathway enzymes and boosting co-factor supply. The final yeast strain produced melatonin at a titer of 14.50 ± 0.57 mg L(-1) in a 76h fermentation using simulated fed-batch medium with glucose as sole carbon source. Our study lays the basis for further developing a yeast cell factory for biological production of melatonin.
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We have recently discovered that melatonin, given acutely and directly to the isolated heart at the concentration found in wine, confers cardioprotection against ischemia-reperfusion (I/R). However, whether the presence of melatonin in wine contributes to the cardioprotective effect of chronic and moderate consumption of wine and its signalling mechanisms of protection are unknown. We therefore used both in vivo and in vitro models of I/R to investigate whether the presence of melatonin in red wine may contribute to the cardioprotective effect of chronic and moderate consumption of red wine. Wistar rats and C57black6 mice (WT) received drinking water supplemented daily with a moderate amount of red wine or melatonin given at the concentration found in the red wine. Rats were also pretreated with luzindole, a specific inhibitor of melatonin receptors 1 and 2 (2.3 mg/kg/day, intraperitoneally) or prazosin, a specific inhibitor of melatonin receptor type 3 (2.5mg/kg/day, intraperitoneally). After 14 days, hearts were subjected to I/R in vivo or ex vivo. Red wine reduced the infarct size in both rats and WT mice (p<0.001). Luzindole did not affect wine-induced cardioprotection, while prazosin reduced the infarct sparing effect of red wine (p<0.05). Furthermore, red wine or melatonin failed to protect tumor necrosis factor alpha (TNF) receptor 2 knockout or cardiomyocyte specific signal transducer and activator of transcription 3 (STAT3) deficient mice (n.s. vs control). Our novel findings suggest that the presence of melatonin in red wine contributes to the cardioprotective effect of chronic and moderate consumption of red wine against lethal I/R injuries. This effect is most likely mediated, at least in part, via melatonin receptor 3 and the activation of TNF and STAT3, both key players of the prosurvival and well described SAFE pathway. Copyright © 2015. Published by Elsevier Inc.
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Melatonin (N-acetyl-5-methoxytryptamine) is an indolic compound derived from tryptophan. Usually identified as a neurotransmitter or animal hormone, this compound was detected in plants in 1995. Interest in knowing the melatonin content of plants and its possible role therein is growing, as indicated by the increasing number of related publications. Melatonin is present in all plant species studied, with large variations in its level depending on the plant organ or tissue. It seems to be more abundant in aromatic plants and in leaves than in seeds. Regarding its physiological function in plants, melatonin shows auxin activity and is an excellent antioxidant, regulating the growth of roots, shoots, and explants, activating seed germination and rhizogenesis (lateral- and adventitious-roots), and delaying induced leaf senescence. Its ability to strengthen plants subjected to abiotic stress such as drought, cold, heat, salinity, chemical pollutants, herbicides, and UV radiation makes melatonin an interesting candidate for use as a natural biostimulating substance for treating field crops.
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Wine is made up of more than one thousand compounds, the majority of which, such as vitamins and minerals, come from the grapes, while others, like ethanol and glycerol, are products of the winemaking process. Although sugars are either partially or completely transformed, sugar import and accumulation into the ripening berry is a major parameter of wine quality. Sugar status is directly related to the final alcoholic content of wine, and regulates several genes responsible for the development of its aromatic and organoleptic properties. Physiological ripeness is reached when the grapes achieve sufficiently high sugar levels without loosing too much acidity; however, aromatic and phenolic compound content must also be taken into account. Softening and water content are other essential characteristics of a ripe berry. From a winemaker point of view, optimal grape maturity is essential for wine quality, but is difficult to assess because it is under multifactorial control, involving grapevine cultivar variety and environmental parameters such as soil, temperature, exposure to sun, and hormonal regulation. Continued study of the key control points in grape ripening is crucial if we ultimately hope to improve grape and wine quality.
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The presence of melatonin in plants is universal. Evidence has confirmed that a major portion of the melatonin is synthesized by plants themselves even though a homologue of the classic arylalkylamine N-acetyltransferase (AANAT) has not been identified as yet in plants. Thus, the serotonin N-acetylating enzyme in plants may differ greatly from the animal AANAT with regard to sequence and structure. This would imply multiple evolutionary origins of enzymes with these catalytic properties. A primary function of melatonin in plants is to serve as the first line of defence against internal and environmental oxidative stressors. The much higher melatonin levels in plants compared with those found in animals are thought to be a compensatory response by plants which lack means of mobility, unlike animals, as a means of coping with harsh environments. Importantly, remarkably high melatonin concentrations have been measured in popular beverages (coffee, tea, wine, and beer) and crops (corn, rice, wheat, barley, and oats). Billions of people worldwide consume these products daily. The beneficial effects of melatonin on human health derived from the consumption of these products must be considered. Evidence also indicates that melatonin has an ability to increase the production of crops. The mechanisms may involve the roles of melatonin in preservation of chlorophyll, promotion of photosynthesis, and stimulation of root development. Transgenic plants with enhanced melatonin content could probably lead to breakthroughs to increase crop production in agriculture and to improve the general health of humans.
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To investigate the effect of exogenous melatonin (100 nmol · L⁻¹) on photosynthetic characteristics of grape seedlings under ozone stress (110 nL · L⁻¹), potted Cabernet Sauvigon grapevine were used as materials to be irrigated with melatonin, gas exchange parameters and OJIP fluorescence transient were tested, and combined with chlorophyll fluorescence quenching analysis. The results showed that, the exogenous melatonin increased the content of chlorophyll a, chlorophyll b, carotenoids and the ratio of chlorophyll under ozone stress, increased the net photosynthetic rate (Pn) of grape leaves and number of active reaction centers per unit area (RC/CSm), promoted the probability of a trapped exciton moves an electron into the electron transport chain beyond QA (Ψo), which reduced the photoinhibition under ozone stress. These results suggested that exogenous melatonin promoted the chlorophyll content under the ozone stress, reduced the damage of ozone stress on grape leaf photosynthesis by improving the energy distribution of grape leaf photosystem.
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Adrenic acid (AdA) and docosahexaenoic acid (DHA) peroxidation produces F2-dihomo-IsoPs and neuroprostanes, which have been related oxidative damage on the central nervous system. Besides the polyphenols, melatonin (MEL) and hydroxytyrosol (OHTyr) could be partly responsible for the antioxidant benefits of red wine (excluding colon derivatives). In order to elucidate whether these compounds are responsible for the protective antioxidant effects of red wine, a double-blind, crossover, placebo-controlled in vivo study -involving the intake of red wines and their native musts by healthy volunteers- was performed. The urinary metabolites decreased after administration of red wines, to a greater extent than after the intake of their corresponding musts or ethanol. Melatonin was the most effective compound protecting adrenic acid from oxidative attack, judging by the reduction on the formation of F2-dihomo-isoprostanes. Similarly, hydroxytyrosol protected docosahexaenoic and eicosapentaenoic acids from oxidative attack, being the most effective bioactive compound in reducing the formation of F3-neuroprostanes n-6 DPA and F4-neuroprostanes.
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The Mediterranean Diet (MD) has been proved to exert benefits with respect to the maintenance of the redox balance, and wine is a representative component. Bioactive compounds such as polyphenols, melatonin and hydroxytyrosol act as radical scavengers and regulate the oxidation status of the organism. Oxidative damage to DNA yields a large range of end products. The repair of oxidized DNA entails the removal of the useless bases and/or nucleotides as well as the release of circulating nucleotides and nucleosides. The current research aims to elucidate, for the first time, the DNA protection against oxidative stress provided by three types of red wine -relating it to the intake of bioactive compounds- after the intake of a serving of red wine/must by 18 healthy female volunteers during short term double-blind, crossover and placebo-controlled study. The novelty of our manuscript is to describe the importance of melatonin, hydroxytyrosol and its metabolites (from gut microflora) in comparison with polyphenols in red wine matrix (excluding colon derivatives). The results show that the intake of red wine and must secondarily, reduces oxidative stress and carcinogenesis due to their content on homovanillic acid, as measured by decreases plasmatic concentration of 8-hydroxy-2´deoxyguanosine, 8-hydroxyguanine, and 8-nitroguanosine. Moreover, the intake of wine appears to exert vasodilatory effects, mediated by the action of nitric oxide and increased plasma guanosine-3′-5′-cyclic monophosphate plasmatic levels, owing to the intake of wines higher in melatonin and homovanillic acid. Therefore, the results obtained at the present manuscript revealed that polyphenols, despite being major compounds in red wine matrix, are not the most effective compounds protecting DNA from oxidative attack.
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Melatonin is a neurohormone involved in the regulation of circadian rhythms in humans. Evidence has recently been found of its occurrence in wines and its role in the winemaking process. The yeast Saccharomyces cerevisiae is consequently thought to be important in Melatonin synthesis, but limited data and reference texts are available on this synthetic pathway. This paper aims to elucidate whether the synthetic pathway of Melatonin in Saccharomyces and non-Saccharomyces strains involves these intermediates. To this end, seven commercial strains comprising Saccharomyces cerevisiae (Red Fruit, ES488, Lalvin QA23, Uvaferm BC, and Lalvin ICV GRE) and non-Saccharomyces (Torulaspora delbrueckii and Metschnikowia pulcherrima) were monitored, under controlled fermentation conditions, in synthetic must, for seven days. Samples were analysed using a UHPLC—HRMS system (Qexactive). Five out of the seven strains formed Melatonin during the fermentation process: three S. cerevisiae strains and the two non-Saccharomyces. Additionally, other compounds derived from L-tryptophan occurred during fermentation.
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The first detection of melatonin in grapes appeared in 2006 with the questioning title 'Melatonin content in grape: myth or panacea?'. Then, in a Letter to the Editor of Journal of Pineal Research, the lead journal covering all aspects of physiology, pathophysiology and endocrinology of melatonin in vertebrates (and all other species), dated 2009, panacea triumphed on myth (the title was 'Melatonin in grape, not just a myth, maybe a panacea') (Iriti, 2009). This meant that, despite the preliminary and incomplete reports regarding melatonin in grapes, a new tessera was added to the mosaic of the complex grape chemistry, further substantiating the health potential of grape products. Since then, melatonin and its isomers were detected both in red and white wines, and a number of exciting papers elucidated that both endogenous and exogenous factors may influence the biosynthesis and accumulation of these indoleamines in grapevine tissues and organs, namely varietal differences, phenological stages, day-night cycle and agrochemical treatments. Probably and similar to polyphenols and other secondary metabolites, many other environmental parameters may regulate melatonin production in grapevine, including climatic conditions, plant-microbe interactions and agricultural practices. On the other hand, because of the paucity of data on the physiological and pathophysiological roles of melatonin in grapevine, we can only hypothesize: from studies on other plants, we predict melatonin is involved in protection from oxidative and abiotic stresses.
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The variations in melatonin and its isomer content were studied during ethanol fermentation by three different Saccharomyces cerevisiae strains, that is, A, B, and F. Additionally, the relationship between melatonin/melatonin isomer and the fermentation process was preliminarily explored and verified by wine fermentation of four types of berries (strawberry, blueberry, mulberry, and raspberry). The results showed that the melatonin content reached the maximum on day 1 and then decreased rapidly. Maximum values obtained for S. cerevisiae strains A, B, and F were 0.773, 0.647, and 0.825 ng/mL, respectively. The content of melatonin isomer reached the maximum on day 3 and then gradually decreased toward later stages. The maximum values obtained for S. cerevisiae strains A, B, and F were 34.89, 19.24, and 26.79 ng/mL, respectively. Thus, the content of the melatonin isomer was significantly higher than that of melatonin (p < 0.01). However, there were no significant differences in melatonin content before and after wine fermentation of the berries (strawberry, blueberry, mulberry, and raspberry), whereas the melatonin isomer content after fermentation was 64.4, 7.37, 81.9, and 55.5 ng/mL, respectively, which was significantly higher than the melatonin content. In summary, melatonin and its isomer were produced in the early fermentation stage and their individual content gradually decreased during the mid-to-late stage, which was speculated to be closely related to the stress response by S. cerevisiae during early stages of fermentation. ©, 2015, South China University of Technology. All right reserved.
Article
A comprehensive investigation was carried out to determine the effect of exogenous melatonin treatment of pre-veraison grapes on grape berries and its wines. Two melatonin treatments of pre-veraison grape berries increased the weight of the berries by approximately 6.6%. Meanwhile, this melatonin treatment could be beneficial in the reduction of underripe and overripe fruits and in enhancing the synchronicity of the berries. In addition, there were significant differences in the volatile compound composition between the wine produced from the melatonin-treated berries and the wines made from untreated berries. The wine from melatonin-treated pre-veraison grape berries had stronger fruity, spicy, and sweet sensory properties, compared to the wines made from untreated berries. Prolonging the treatment through repeated applications can enhance these effects and under different seasonal conditions, more pronounced effects on the grape quality and wine properties can be observed. Copyright © 2015 Elsevier Ltd. All rights reserved.
Article
The beneficial effect that melatonin has against mitochondrial dysfunctioning seems to be linked to mitophagy. Roles for melatonin have been demonstrated in promoting health and preventing disease, as well as activating the process of autophagy in general. However, no reports have been made about how the application of melatonin regulates that process when plants are exposed to oxidative stress. We investigated the influence of different concentrations of melatonin (0.0, 0.5, 5.0, 10.0, or 50.0 μM) on autophagy under methyl viologen (MV)-induced oxidative stress. Arabidopsis seedlings that were pre-treated with 5 or 10 μM melatonin underwent relatively strong induction of autophagy, as evidenced by the number of monodansylcadaverine (MDC)-stained autophagosomes in root samples. Pretreatment with 10 μM melatonin also alleviated MV-induced photo-oxidation damage and significantly reduced the accumulation of oxidized proteins. Those responses might have been due to the strong up-regulation of genes that involved in AtATG8-PE conjugation pathway, which enhanced the capacity for autophagy. Histochemical staining revealed that both O2 (-) · and H2 O2 were highly accumulated upon MV exposure, although the response did not differ significantly between control and melatonin-pretreated seedlings. By contrast, exogenous melatonin up-regulated the expression of two genes for H2 O2 -scavenging enzymes, i.e., AtAPX1 and AtCATs. The activation of autophagy by melatonin without an alteration in ROS production may be part of a survival mechanism that is enhanced by melatonin after cellular damage. Therefore, it represents a second level of defense to remove damaged proteins when antioxidant activities are compromised. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.
Article
Melatonin (MEL) has been found in some medicinal and food plants, including grapevine, a commodity of particular interest for the production of wine, a beverage of economic relevance. It has also been suggested that MEL in wine may, at least in part, contribute to the health-promoting properties attributed to this beverage and, possibly, to other traditional Mediterranean foodstuffs. After a preliminary screening of 9 yeast strains in laboratory medium, 3 selected strains (Saccharomyces cerevisiae EC1118, Torulaspora delbrueckii CBS1146(T) and Zygosaccharomyces bailii ATCC36947(T) ) were inoculated in experimental musts obtained from 2 white (Moscato and Chardonnay) and 2 red (Croatina and Merlot) grape varieties. The production of MEL, melatonin isomers (MIs) and tryptophan-ethylester (TEE) was monitored during the alcoholic fermentation. The screening showed that the three investigated strains produced the highest concentrations of MEL and two MIs in optimal growth conditions. However, MEL and MIs were not produced in oenological conditions, but the three strains synthesized high concentrations of a new MI and TEE in musts. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.
Article
Melatonin (MLT) and two structurally related compounds, 5-methoxytryptamine (5MT) and 5-methoxytryptophol (5 ML), are formed in Saccharomyces cerevisiae in high concentrations. Depending on conditions, levels can attain several ng/mg protein, sometimes more than 10 (MLT, 5MT) or 20 (up to >100: 5 ML) ng/mg. Starvation in salt medium leads to a drop in all methoxyindoles below detection thresholds. After 4 h in salt, reincubation in growth medium restores high levels. Addition of tryptophan, serotonin or N-acetylserotonin to starved cells also elevates MLT and 5MT Exogenous MLT (50 or 100 μM) causes 5MT to rise above 700 ng/mg protein within 0.5 h, whereas same concentrations of exogenous 5MT lead to >90->300 ng MLT/mg. Therefore, MLT can be synthesized via the most common pathway from tryptophan to N-acetylserotonin as a direct precursor, and is deacetylated to 5MT; biosynthesis of MLT by N-acetylation of 5MT is a secondary pathway.
Article
Melatonin pre-treatment significantly increases the tolerance of both drought-tolerant Malus prunifolia and drought-sensitive M. hupehensis plants. Its beneficial effects include better water conservation in leaves, less electrolyte leakage, steady chlorophyll contents, and greater photosynthetic performance under stress conditions. Melatonin selectively down-regulates MdNCED3, an abscisic acid (ABA) synthesis gene, and up-regulates its catabolic genes, MdCYP707A1 and MdCYP707A2, thereby reducing ABA contents in drought-stressed plants. Melatonin also directly scavenges H2O2 and enhances the activities of antioxidant enzymes to detoxify H2O2 indirectly. These two mechanisms work synergistically to improve the functions of stomata, i.e. causing them to re-open. Plants can effectively regulate their water balance under drought conditions by up-regulating the expression of melatonin synthesis genes MdTDC1, MdAANAT2, MdT5H4, and MdASMT1. Therefore, inducing melatonin production is an important mechanism by which plants can counteract the influence of this abiotic stressor. © The Author 2014. Published by Oxford University Press on behalf of the Society for Experimental Biology. All rights reserved. For permissions, please email: journals.permissions@oup.com.
Article
Melatonin is a neurohormone, chronobiotic and antioxidant compound found in wine and deriving directly from grapes and/or synthesized by yeast during alcoholic fermentation. In addition, a melatonin isomer has been detected in different foods, wine among them. The special interest for melatonin isomer related to the fact that it was found in greater quantities than melatonin, and probably shares some of its biological properties. Despite this, its chemical structure has not yet been defined; although some researchers hypothesize it could be melatonin with the ethylacetamide group shifted into position N1. Thus, the aim of our study was to identify the structures of the melatonin isomer. For this purpose, melatonin and melatonin isomer in Syrah wine were separated chromatographically by a sub-2 μm particle column and detected by tandem mass spectrometry. The sample was then purified and concentrated by solid-phase extraction, hydrolyzed with alkali or esterase, and substrates and products quantified by UPLC-MS/MS. Moreover, melatonin, melatonin isomer and their product ions were evaluated by high-resolution mass spectrometry. The amount of melatonin isomer and melatonin in the wine was 84±4 and 3±0 ng/mL, respectively. In the solutions, containing diluted alkali or esterase, melatonin isomer was hydrolyzed in about 8 min. Correspondingly, tryptophan was detected and its amount increased and reached the maximum concentration in about 8 min. Melatonin concentration was not affected by diluted alkali or esterase. The fragmentation pattern of melatonin isomer was different from that of melatonin but comparable to that of tryptophan-ethylester. Finally, the so-called melatonin isomer identity was verified by co-chromatography with authentic standard of tryptophan-ethylester.This article is protected by copyright. All rights reserved.
Article
Although previous studies have found that melatonin can promote seed germination, the mechanisms involved in perceiving and signaling melatonin remain poorly understood. In this study, it was found that melatonin was synthesized during cucumber seed germination with a peak in melatonin levels occurring 14 hours into germination. This is indicative of a correlation between melatonin synthesis and seed germination. Meanwhile seeds pre-treated with exogenous melatonin (1μM) showed enhanced germination rates under 150mM NaCl stress compared to water pre-treated seeds under salinity stress. There are two apparent mechanisms by which melatonin alleviated salinity induced inhibition of seed germination. Exogenous melatonin decreased oxidative damage induced by NaCl stress by enhancing gene expression of antioxidants. Under NaCl stress, compared to untreated control, the activities of antioxidant enzymes including superoxide dismutase (SOD), catalase (CAT) and peroxidase (POD) were significantly increased by approximately 1.3-5.0-fold, with a concomitant 1.4-2.0-fold increase of CsCu-ZnSOD, CsFe-ZnSOD, CsCAT and CsPOD in melatonin pre-treated seeds. Melatonin also alleviated salinity stress by affecting abscisic acid (ABA) and gibberellin acid (GA) biosynthesis and catabolism during seed germination. Compared to NaCl treatment, melatonin significantly up-regulated ABA catabolism genes (e.g. CsCYP707A1 and CsCYP707A2, 3.5 and 105-fold higher than NaCl treatment at16 hr, respectively) and down-regulated ABA biosynthesis genes (e.g. CsNECD2, 0.29-fold of CK2 at 16 hr), resulting in a rapid decrease of ABA content during the early stage of germination. At the same time, melatonin positively up-regulated GA biosynthesis genes (e.g. GA20ox and GA3ox, 2.3 and 3.9-fold higher than NaCl treatment at 0 and 12 hr, respectively), contributing to a significant increase of GA (especially GA4) content. In this study, we provide new evidence suggesting that melatonin alleviates the inhibitory effects of NaCl stress on germination mainly by regulating the biosynthesis and catabolism of ABA and GA4.This article is protected by copyright. All rights reserved.
Article
Grapes are an important economic crop and are widely cultivated around the world. Most grapes are grown in arid or semi-arid regions, and droughts take a heavy toll in grape and wine production areas. Developing effective drought-resistant cultivation measures is a priority for viticulture. Melatonin, an indoleamine, mediates many physiological processes in plants. Herein, we examined whether exogenously applied melatonin could improve the resistance of wine grape seedlings grown from cuttings to polyethylene glycol-induced water-deficient stress. The application of 10% polyethylene glycol (PEG) markedly inhibited the growth of cuttings, caused oxidative stress and damage from H2O2 and O2•−, and reduced the potential efficiency of Photosystem II and the amount of chlorophyll. Application of melatonin partially alleviated the oxidative injury to cuttings, slowed the decline in the potential efficiency of Photosystem II, and limited effects on leaf thickness, spongy tissue, and stoma size after application of PEG. Melatonin treatment also helped preserve the internal lamellar system of chloroplasts and alleviated the ultrastructural damage induced by drought stress. This ameliorating effect may be ascribed to the enhanced activity of antioxidant enzymes, increased levels of non-enzymatic antioxidants, and elevated amount of osmoprotectants (free proline). We conclude that the application of melatonin to wine grapes is effective in reducing drought stress.This article is protected by copyright. All rights reserved.
Article
Melatonin (N-acetyl-5-methoxytryptamine), is not only a widely known animal hormone, but also an important regulator in plant development and multiple abiotic stress responses. Recently, it has been revealed that melatonin alleviated cold stress through mediating several cold-related genes, including C-REPEAT-BINDING FACTORs (CBFs)/Drought Response Element Binding factors (DREBs), COR15a, and three transcription factors (CAMTA1, ZINC FINGER OF ARABIDOPSIS THALIANA 10 (ZAT10), and ZAT12). In this study, we quantified the endogenous melatonin level in Arabidopsis plant leaves, and found the endogenous melatonin levels were significantly induced by cold stress (4°C) treatment. In addition, we found one Cysteine2/Histidine2-type zinc finger transcription factor, ZAT6, was involved in melatonin-mediated freezing stress response in Arabidopsis. Interestingly, exogenous melatonin enhanced freezing stress resistance was largely alleviated in AtZAT6 knockdown plants, but was enhanced in AtZAT6 overexpressing plants. Moreover, the expression levels of AtZAT6 and AtCBFs were commonly up-regulated by cold stress (4°C) and exogenous melatonin treatments, and modulation of AtZAT6 expression significantly affected the induction AtCBFs transcripts by cold stress (4°C) and exogenous melatonin treatments. Taken together, AtZAT6-activated CBF pathway might be essential for melatonin-mediated freezing stress response in Arabidopsis. This article is protected by copyright. All rights reserved.
Article
Melatonin (N-acetyl-5-methoxytryptamine) has been implicated in abiotic and biotic stress tolerance in plants. However, information on the effects of melatonin in cold stress tolerance in vivo is limited. In this study, the effect of melatonin was investigated in the model plant Arabidopsis thaliana challenged with a cold stress at 4⁰C for 72 and 120 hrs. Melatonin treated plants (10 and 30 μM) had significantly higher fresh weight, primary root length and shoot height compared to the non-treated plants. To aid in the understanding of the role of melatonin in alleviating cold stress, we investigated the effects of melatonin treatment on the expression of cold-related genes. Melatonin up-regulated the expression of, C-repeat binding factors (CBFs)/ Drought Response Element Binding Factors (DREBs), a cold-responsive gene, COR15a, a transcription factor involved in freezing and drought stress tolerance CAMTA1 and transcription activators of reactive oxygen species (ROS) related antioxidant genes, ZAT10 and ZAT12, following cold stress. The up-regulation of cold signaling genes by melatonin may stimulate the biosynthesis of cold-protecting compounds and contribute to the increased growth of plants treated with exogenous melatonin under cold stress. This article is protected by copyright. All rights reserved.
Article
Temperature and light are important environmental factors for plant growth and development. The final two enzymes in the melatonin synthesis pathway in plants are serotonin N-acetyltransferase (SNAT) and N-acetylserotonin methyltransferase (ASMT), which have thermophilic characteristics. Thus, the effects of temperature and light on melatonin synthesis in rice seedlings were investigated. Here, we demonstrated that melatonin levels increased as temperature increased when rice seedlings were exposed to various temperatures for 1 hr. Moreover, the relative melatonin levels were higher in the dark. For example, exposure of rice seedlings to 1-hr darkness at 55°C resulted in a melatonin yield of 4.9 ng/g fresh weight (fw), compared to 2.95 ng/g fw under light conditions. Temperature-dependent melatonin synthesis was closely associated with an increase in both SNAT and ASMT activities, but not with transcript levels of melatonin biosynthetic genes. The daily melatonin levels in field-grown rice plants were unaffected since the effect of the relatively high temperature during the day was counteracted by the negative effect of the high light level. The opposite effect occurred during the night, in which the positive effect of darkness on melatonin synthesis was counteracted by the negative effect of a low temperature. This article is protected by copyright. All rights reserved.
Article
Melatonin is present in many edible fruits; however, the presence of melatonin in apple has not previously been reported. In this study, the genes for melatonin synthetic enzymes including tryptophan decarboxylase, tryptamine 5-hydroxylase (T5H), arylalkylamine N-acetyltransferase, and N-acetylserotonin methyltransferase were identified in 'Red Fuji' apple. Each gene has several homologous genes. Sequence analysis shows that these genes have little homology with those of animals and they only have limited homology with known genes of rice melatonin synthetic enzymes. Multiple origins of melatonin synthetic genes during the evolution are expected. The expression of these genes is fully coordinated with melatonin production in apple development. Melatonin levels in apple exhibit an inverse relationship with the content of malondialdehyde, a product of lipid peroxidation. Two major melatonin synthetic peaks appeared on July 17 and on October 8 in both unbagged and bagged apple samples. At the periods mentioned above, apples experienced rapid expansion and increased respiration. These episodes significantly elevate reactive oxygen species production in the apple. Current data further confirmed that melatonin produced in apple was used to neutralize the toxic oxidants and protect the developing apple against oxidative stress.
Article
Regular moderate wine consumption is often associated with reduced morbidity and mortality from a variety of chronic diseases in which inflammation is the root cause. This review is focused on three of the numerous bioactive compounds present in wine: resveratrol, hydroxytyrosol and melatonin. Resveratrol and hydroxytyrosol are polyphenols. Melatonin, recently described in wine, is an indoleamine. Their structures, concentrations in wine, bioavailability, pharmacokinetic and health promoting properties are reviewed. Resveratrol seems to be one of the most promising compounds due to its bioactivity, with wine being the main source of resveratrol in diet. Hydroxytyrosol, which its main source in diet is olive oil has been also found in both red and white wine in considerable amounts. Melatonin has been found in wine in low amounts. However, both high bioactivity and bioavailability have been attributed to it. They show antioxidant, cardioprotective, anticancer, antidiabetic, neuroprotective and antiaging activities. However, human studies are still in the initial stages and therefore further studies are needed.
Article
Melatonin (N-acetyl-5-methoxytryptamine) is a molecule implicated in multiple biological functions. Its level decreases with age, and the intake of foods rich in melatonin has been considered an exogenous source of this important agent. Orange is a natural source of melatonin. Melatonin synthesis occurs during alcoholic fermentation of grapes, malt and pomegranate. The amino acid tryptophan is the precursor of all 5-methoxytryptamines. Indeed, melatonin appears in a shorter time in wines when tryptophan is added before fermentation. The aim of the study was to measure melatonin content during alcoholic fermentation of orange juice and to evaluate the role of the precursor tryptophan. Identification and quantification of melatonin during the alcoholic fermentation of orange juice was carried out by UHPLC-QqQ-MS/MS. Melatonin significantly increased throughout fermentation from day 0 (3.15 ng/mL) until day 15 (21.80 ng/mL) reaching larger amounts with respect to other foods. Melatonin isomer was also analysed, but its content remained stable ranging from 11.59 to 14.18 ng/mL. The enhancement of melatonin occurred mainly in the soluble fraction. Tryptophan levels significantly dropped from 13.80 mg/L (day 0) up to 3.19 mg/L (day 15) during fermentation. Melatonin was inversely and significantly correlated with tryptophan (r = 0.907). Therefore, the enhancement in melatonin could be due to both the occurrence of tryptophan and the new synthesis by yeast. In summary, the enhancement of melatonin in novel fermented orange beverage would improve the health benefits of orange juice by increasing this bioactive compound.
Article
Melatonin (MT) presence in higher plants was recently discovered and the knowledge of its function in vivo is limited. Several studies have recently shown the occurrence of MT and related compounds in grapes and wines. The analysis of MT in plants and foods represents a highly challenging task due to its wide concentration range, the difficulty in the selection of the extraction solvents because of its amphipathic nature, and the fact that it reacts quickly with other matrix components. Thus, sample processing factors; preparation/cleanup procedures; and chromatographic/detection parameters, such as HILIC and reverse phase (C8 and C18 ) chromatographic modes, ESI, and atmospheric pressure chemical ionization (APCI) in both negative and positive modes were evaluated. Taken together, we have demonstrated that optimal conditions were quite different for each of the matrices under study. A sonication-mediated extraction step was necessary for grape skin (100% v/v methanol) and plant tissues (50% v/v methanol), while wine and must required a SPE preconcentration step. HILIC-(+) APCI ionization was better for MT standards, while C8 -(+) APCI was the best choice for grape skin and C18 -(+ESI) was suitable for wine. On the other hand, C8 -(+)ESI was the most appropriate for vegetal tissues of Arabidopsis thaliana. Proposed methods were validated and the LODs were in the low picogram levels range. The optimized approaches were applied to the determination of MT and its isomer in different vegetal/food samples; levels found within the range: 4.9-440 ng/g.
Article
We examined whether exogenously applied melatonin could improve resistance to Marssonina apple blotch (Diplocarpon mali) by apple [Malus prunifolia (Willd.) Borkh. cv. Donghongguo]. This serious disease leads to premature defoliation in the main regions of apple production. When plants were pretreated with melatonin, resistance was increased in the leaves. We investigated the potential roles for melatonin in modulating levels of hydrogen peroxide (H(2) O(2) ), as well the activities of antioxidant enzymes and pathogenesis-related proteins during these plant-pathogen interactions. Pretreatment enabled plants to maintain intracellular H(2) O(2) concentrations at steady-state levels and enhance the activities of plant defence-related enzymes, possibly improving disease resistance. Because melatonin is safe and beneficial to animals and humans, exogenous pretreatment might represent a promising cultivation strategy to protect plants against this pathogen infection.
Article
Although polyphenols represent the paradigm of the health-promoting effects ascribed to grape products, recently, attention has been paid to dietary melatonin, significantly present in Mediterranean foods. In this work, we measured melatonin, its isomers, stilbenes (trans- and cis-resveratrol and their glucosides, piceids) and total polyphenols in some different grape products (red, white and dessert wines, grape juices and Modena balsamic vinegars) of distinct Italian areas. We also evaluated their antiradical activity by DPPH(·) and ABTS(·+) assays. For indoleamine analysis, the separation was carried out on a 1.7-μm C(18) BEH column and the detection performed by means of mass spectrometry with electrospray ionization in positive ion mode with multiple reaction monitoring. The confirmation of the peak identity was accomplished by injection into the high-resolution system (Orbitrap) using accurate mass measurements (error below 1.0 ppm). Mass spectrometry analyses revealed, for the first time, the presence of melatonin in dessert wines and balsamic vinegars, as well as the occurrence of three different melatonin isomers in grape products.
Article
To examine the potential roles of melatonin in drought tolerance, we tested the effects of its long-term exogenous application on 'Hanfu' apple (Malus domestica Borkh.). When 100 μm melatonin was added to soils under drought conditions, the resultant oxidative stress was eased and leaf senescence was delayed. This molecule significantly reduced chlorophyll degradation and suppressed the up-regulation of senescence-associated gene 12 (SAG12) and pheophorbide a oxygenase (PAO). Such treatment also alleviated the inhibition of photosynthesis brought on by drought stress. We also investigated quenching and the efficiency of Photosystem II (PSII) photochemistry under dark and light conditions and found that melatonin helped to maintain better function of PSII under drought. The addition of melatonin also controlled the burst of hydrogen peroxide, possibly through direct scavenging and by enhancing the activities of antioxidative enzymes and the capacity of the ascorbate-glutathione cycle. Thus, understanding this effect of melatonin on drought tolerance introduces new possibilities to use this compound for agricultural purposes.
Article
To examine whether melatonin-rich plants can defend against oxidative stress, we subjected melatonin-rich transgenic (MRT) rice plants to the singlet-oxygen-generating herbicide butafenacil. Both MRT and transgenic control (TC; expressing the vector only) rice seeds germinated and grew equally well in continuous dark on half-strength Murashige and Skoog (MS) medium containing 0.1 μm butafenacil. However, after transferring the seedlings to light, the TCs rapidly necrotized, whereas the MRT seedlings showed resistant phenotypes. Seven-day-old MRT seedlings treated with 0.1 μm butafenacil were resistant to the herbicide and contained high chlorophyll levels and low malondialdehyde and hydrogen peroxide contents compared with the TCs. As they did before the herbicide treatment, the MRT plants also produced much more melatonin after the herbicide treatment than the TCs. In addition, the MRT plants exhibited higher superoxide dismutase and catalase activities before and after the herbicide treatment compared with the TCs. This is the first report showing that MRT plants exhibit resistance against a peroxidizing herbicide that acts by generating reactive oxygen species (ROS) that kill plants. This result indicates that melatonin scavenges ROS efficiently in vivo in the transgenic plants, leading to oxidative stress resistance.
Article
Melatonin (N-acetyl-5-methoxytryptamine) is an animal hormone synthesized predominantly at night. It often serves as a signal of darkness that regulates circadian rhythmicity and photoperiodism. Melatonin has also been found in algae and higher plants, including the short-day flowering plant Chenopodium rubrum. To test its involvement in plant photoperiodism, melatonin solutions were applied to the cotyledons and plumules of 5-day-old-seedlings of Chenopodium rubrum L., ecotype 374. 3H-labelled melatonin was readily taken up by the plants and was very stable for a period of 37 h from application. Treatment with 100 and 500 µM melatonin significantly reduced flowering of plants exposed to a single inductive 12-h darkness. Melatonin was efficient only when applied before lights off or during the first half of the dark period. This indicates that melatonin affects some early steps of the transition to flowering. However, it had no effect on the period or phase of a circadian rhythm in photoperiodic time measurement. Melatonin agonists (2-I-melatonin, 6-Cl-melatonin, CGP 52608) and 5-hydroxytryptamine also reduced flowering, whereas 5-methoxytryptamine did not. The results demonstrate that exogenous melatonin is able to influence the early stages of photoperiodic flower induction and/or flower development in a higher plant. Possible mechanisms for this effect are discussed.
Article
  A comprehensive investigation was carried out to determine the changes that occurred in water-stressed cucumber (Cucumis sativus L.) in response to melatonin treatment. We examined the potential roles of melatonin during seed germination and root generation and measured its effect on reactive oxygen species (ROS) levels, antioxidant enzyme activities, and photosynthesis. Melatonin alleviated polyethylene glycol induced inhibition of seed germination, with 100 μm melatonin-treated seeds showing the greatest germination rate. Melatonin stimulated root generation and vitality and increased the root:shoot ratio; therefore, melatonin may have an effect on strengthening cucumber roots. Melatonin treatment significantly reduced chlorophyll degradation. Seedlings treated with 100 μm melatonin clearly showed a higher photosynthetic rate, thus reversing the effect of water stress. Furthermore, the ultrastructure of chloroplasts in water-stressed cucumber leaves was maintained after melatonin treatment. The antioxidant levels and activities of the ROS scavenging enzymes, i.e., superoxide dismutase, peroxidase, and catalase, were also increased by melatonin. These results suggest that the adverse effects of water stress can be minimized by the application of melatonin.
Article
Melatonin (N-acetyl-5-methoxytryptamine) was detected by a modified HPLC method and ELISA tests in extracts of eight different Vitis vinifera cultivars, namely Nebbiolo, Croatina, Sangiovese, Merlot, Marzemino, Cabernet Franc, Cabernet Sauvignon and Barbera. Its concentration varied greatly among the cultivars, being the highest in Nebbiolo (0.965 ng g−1) and Croatina (0. 870 ng g−1). Field treatments of grapevine with the plant defence activator benzothiadiazole, greatly improved the melatonin content in berry skin extracts, indicating a possible strategy to raise the content of this important pharmaconutrient in plants, while inducing resistance to pathogens. The finding of this compound in grape suggests that the well-established pharmaconutritional properties of this fruit are due not only to the presence of polyphenolic nutraceuticals, such as resveratrol, anthocyanins and proanthocyanidins, but also to the powerful antioxidant activity of melatonin. Copyright © 2006 Society of Chemical Industry
Chapter
There is increasing evidence in the literature that the pineal hormone melatonin (N-acetyl-5-methoxytryptamine) can have beneficial effects on the health of human subjects including cases of sleep disorders, jet lag, free radical disorders and cancer. A number of studies show that melatonin is found in plants at varying but significant concentrations. Research shows that in animal subjects feeding of high melatonin fodder results in a rise of plasma melatonin levels. In addition melatonin from plant extracts has been shown to bind to rabbit brain receptors. In view of this evidence further research into plant melatonin may provide valuable information not only as to why melatonin exists in the plant kingdom, but also important comparative information for those with an interest in nutraceuticals and medicinal foodstuffs
Article
Melatonin is a bioactive compound that is present in wine because it is contained in vinification grapes and synthesized by yeast during alcoholic fermentation. The purpose of this study was to determine the capacity of various Saccharomyces strains to form melatonin during its growth and alcoholic fermentation. A selection of yeasts including six S. cerevisiae (Lalvin CLOS, Lalvin ICV-D254, Enoferm QA23 Viniferm ARM, Viniferm RVA, and Viniferm TTA), one S. uvarum (Lalvin S6U) and one S. cerevisiae var. bayanus (Uvaferm BC) were tested to determine whether they produce melatonin in yeast extract peptose dextrose and synthetic must media in a variety of conditions. Two S. cerevisiae strains (ARM, and QA23), the S. uvarum and the S. cerevisiae var. bayanus, synthesized melatonin. The conditions in which they did so, however, were different: the QA23 strain produced melatonin best in a medium with a low concentration of reducing sugars and Lalvin S6U and Uvaferm BC required a synthetic must under fermentation conditions. Melatonin synthesis largely depended on the growth phase of the yeasts and the concentration of tryptophan, reducing sugars and the growth medium. These results indicate that melatonin may have a role as a yeast growth signal molecule.
Article
As an indoleamine molecule, melatonin mediates many physiological processes in plants. We investigated its role in regulating growth, ion homeostasis, and the response to oxidative stress in Malus hupehensis Rehd. under high-salinity conditions. Stressed plants had reduced growth and a marked decline in their net photosynthetic rates and chlorophyll contents. However, pretreatment with 0.1 μm melatonin significantly alleviated this growth inhibition and enabled plants to maintain an improved photosynthetic capacity. The addition of melatonin also lessened the amount of oxidative damage brought on by salinity, perhaps by directly scavenging H(2) O(2) or enhancing the activities of antioxidative enzymes such as ascorbate peroxidase, catalase, and peroxidase. We also investigated whether melatonin might control the expression of ion-channel genes under salinity. Here, MdNHX1 and MdAKT1 were greatly up-regulated in the leaves, which possibly contributed to the maintenance of ion homeostasis and, thus, improved salinity resistance in plants exposed to exogenous melatonin.
Article
Several studies have shown the presence of melatonin and related compounds in grapes and wines. The latter provides evidence of the possibility to enhance the nutraceutical properties of premium wines. However, there are many external factors that can influence the levels of this indolamine in grape and wines. In this study, the monitoring of melatonin and its tentatively identified isomer was carried out during the entire winemaking process in Vitis vinifera cv. Malbec by ultra high-performance liquid chromatography-tandem mass spectrometry. Laboratory and pilot studies were carried out to elucidate the role of grape, yeasts, and tryptophan in the evolution of the indolamines during the fermentation process. Melatonin was detected in grape extract within the range 120-160 ng/g while its isomer was found in musts and finished wines. Our results demonstrate that Saccaromyces cervisiae plays a decisive role in contributing to the content of melatonin and its isomer in wine.
Article
Melatonin (N-acetyl-3-(2-aminoethyl)-5-methoxyindole) is biologically active as a neurohormone and a chronobiotic and antioxidant agent. Its concentration in plant material and foods is usually determined by ELISA. However, commercial ELISA kits are not validated for those matrixes. This paper aims to accurately detect melatonin in wines. The advantages and pitfalls of the methods currently used to assay melatonin in wines (ELISA, LC-fluorescence and LC-ESI-MS/MS) are presented. The LC-FL method was validated as reliable for the quantitative analysis of MEL in wine samples that met AOAC requirements: LOD = 51.72 ng/mL; LOQ = 172.39 ng/mL; intraday accuracy as RSD = 0.35% and interday accuracy as RSD = 13.46%. The linearity showed a correlation coefficient of 0.9999, and peak resolution ranged from 0.96 to 1.52. Melatonin in wines was identified by LC-ESI-MS/MS, comparing its MS and MS2 spectra with its corresponding authentic commercial marker. LC-ESI-MS/MS revealed another compound with an identical fragment pattern (positive-mode ESI) but a different retention time as melatonin. Major mass fragmentation ions were (m/z) 216 and 174, tentatively identified as a melatonin isomer not previously described in wines. This compound appears in certain monovarietal wines (Jaen Tinto, Merlot and Palomino Negro). Only melatonin is present in others (Petit Verdot and Syrah), and a third group contains both melatonin and the new compound (Cabernet Sauvignon, Prieto Picudo and Tempranillo).
Article
Melatonin (N-acetyl-5-methoxytryptamine) is a neurohormone produced in the pineal gland. Its biological properties are related to the circadian rhythm. Recently, the European Food Safety Authority (EFSA) accepted the health claim related to melatonin and the alleviation of subjective feelings of jet lag. This molecule has been detected in some foods. In this work, 13 grape varieties were studied; 7 monovarietal wines were produced in an experimental winery under strictly controlled conditions and were sampled in different steps. The grape varieties used to make the wines were: Cabernet Sauvignon, Merlot, Syrah, Tempranillo, Tintilla de Rota, Palomino Fino and Alpha red. Liquid chromatography tandem mass spectrometry (LC-MS/MS) unequivocally confirmed the presence of melatonin in wines. The main contribution of this paper is the results that clearly show that melatonin is synthesised during the winemaking process, specifically after the alcoholic fermentation. Indeed, melatonin is absent in grapes and musts and is formed during alcoholic fermentation.
Article
The strong antioxidant activity of melatonin is well known and it is important to investigate its presence and levels in different foodstuffs, for the purpose of evaluating their nutraceutical properties. As a contribution towards this goal, an original analytical method has been developed for the simultaneous determination of melatonin and other indolic and phenolic antioxidants (including trans- and cis-resveratrol, ferulic acid, tryptophan, serotonin and 5-hydroxyindoleacetic acid) in grape-related foodstuffs and beverages: namely grape, grape juice, must, wine and grappa (Italian pomace brandy). These foodstuffs represent an important part of the diet, both traditionally and in recent times, especially in Mediterranean countries and could be (at least in part) responsible for the beneficial effects involved in the 'French paradox'. The analytical method is based on high-performance liquid chromatography coupled to fluorescence detection, exploiting the native fluorescence of the analytes. A C8 column was used as the stationary phase, while the mobile phase was composed of acidic phosphate buffer and acetonitrile; fluorescence intensity was monitored at λ=386nm while exciting at λ=298nm. The sample pretreatment was carried out by a fast and reliable microextraction by packed sorbent (MEPS) procedure. After validation, the method was applied to the analysis of melatonin and other antioxidants in food and beverages derived from grape, with very good results being obtained. Thus, this methodology may represent a promising tool for the evaluation of the antioxidant properties of nutraceuticals and functional foods.