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Characterization of Anthocyanins and Proanthocyanidins in Some Cultivars of Ribes , Aronia , and Sambucus and Their Antioxidant Capacity
Abstract
Anthocyanins and proanthocyanidins were characterized by HPLC-ESI-MS/MS coupled with a diode array and/or fluorescent detector in seven cultivars of Ribes nigrum (black currant) and Ribes rubrum (red currant, Red Lake), six cultivars of Ribes grossularia (gooseberries), Aronia melanocarpa(chokeberry), and Sambucus nigra (elderberry). Thirty-one different anthocyanins were detected in these berries, but not every anthocyanin was observed in each berry. A number of minor anthocyanins were identified from these berries for the first time. The concentrations of individual anthocyanins in all of the berries were quantified using relevant anthocyanidin 3-glucoside standards. Among the berries studied in this paper and in berries in general, chokeberry has the highest total anthocyanin concentrations [1480 mg/100 g of fresh weight (FW)], whereas the lowest total anthocyanin concentration in the berries studied was found in the gooseberry cv. Careless, which contained only 0.07 mg/100 g of FW. Two cultivars of gooseberries (Marigold and Leveller) did not contain any anthocyanins. Total proanthocyanidin concentrations in the berries studied ranged from 23 to 664 mg/100 g of FW in elderberry and chokeberry, respectively. Procyanidin or prodelphinidin polymers were the predominant components (>65% w/w) in most of the berries. The lipophilic and hydrophilic antioxidant capacities were measured by the oxygen radical absorbance capacity (ORAC(FL)) procedure. The total antioxidant capacity varied from 21 micromol of TE/g of FW in Careless gooseberry to 161 micromol of TE/g of FW in chokeberry. Total phenolics in the berries in general paralleled hydrophilic antioxidant capacity.
... Flavonoids are found in many food items with more abundance in fruits and vegetables [12]. Berries, like the black elderberry and black chokeberry, have the greatest quantities of flavonoids among fruits [13,14]. Certain fruits that are in the drupes category, such as plum and sweet cherry, have greater flavonoid contents in comparison to the remaining categories [15,16]. ...
... Broad bean pod [18], black olive [19], red onion [20], spinach [21], and shallot [22] are the vegetables having the greatest quantities of flavonoids. [14] Black chokeberry Anthocyanins 1012.98 [14] Plum Anthocyanins 101.67 [16] Sweet cherry Anthocyanins 185.05 [16] Vegetables Broad bean pod Flavan-3-ols 189.54 [18] Black olive Anthocyanins 159.83 [19] Red onion Flavonols 131.51 [20] Spinach Flavonols 119.27 [21] Shallot Flavonols 112.22 [22] Beverages Red wine Flavan-3-ols 83.96 [24] Black tea Flavan-3-ols 83.35 [26] Green tea Flavan-3-ols 77.44 [26] Apple juice Flavan-3-ols 54.99 [27] Orange Juice Flavanones 48.02 [27] Grapefruit juice Flavanones 47.12 [27] Lemon juice Flavanones 37.43 [27] There is a contrast between non-alcoholic and alcoholic beverages. Red wine has the greatest flavonoid content of any alcoholic beverage [23,24]. ...
... Broad bean pod [18], black olive [19], red onion [20], spinach [21], and shallot [22] are the vegetables having the greatest quantities of flavonoids. [14] Black chokeberry Anthocyanins 1012.98 [14] Plum Anthocyanins 101.67 [16] Sweet cherry Anthocyanins 185.05 [16] Vegetables Broad bean pod Flavan-3-ols 189.54 [18] Black olive Anthocyanins 159.83 [19] Red onion Flavonols 131.51 [20] Spinach Flavonols 119.27 [21] Shallot Flavonols 112.22 [22] Beverages Red wine Flavan-3-ols 83.96 [24] Black tea Flavan-3-ols 83.35 [26] Green tea Flavan-3-ols 77.44 [26] Apple juice Flavan-3-ols 54.99 [27] Orange Juice Flavanones 48.02 [27] Grapefruit juice Flavanones 47.12 [27] Lemon juice Flavanones 37.43 [27] There is a contrast between non-alcoholic and alcoholic beverages. Red wine has the greatest flavonoid content of any alcoholic beverage [23,24]. ...
Flavonoids are polyphenolic substances present in plants having a fundamental structure of C6–C3–C6. This structure contains a pair of aromatic rings that are interconnected by a 3‐C chain, resulting in a heterocycle. These are essential components of the human diet, and are found in vegetables, fruits, and beverages that include wines, tea, chocolate, and fruit juices. Except for flavonols, all flavonoids contained in foods are glycosylated, and glycosylation influences absorption. The small intestine absorbs flavonoids into the bloodstream, where they are distributed throughout the body. Their metabolism occurs in the liver and tissues, resulting in metabolites (such as quercetin‐3‐glucuronide, kaempferol‐7‐glucuronide, and isorhamnetin) with altered chemical properties that interact with cellular processes and exhibit antioxidant, anti‐inflammatory, and many other salutary effects. During the process of oxidation, the generation of numerous unstable and highly reactive substances known as free radicals occurs. These highly reactive substances, namely, ROS, cause oxidative stress, a phenomenon closely related to inflammation that results in serious cellular harm. The presence of numerous hydroxyl groups (‐OH) in flavonoids enables them to act as strong antioxidants and neutralize oxidative stress during physiological events. In recent times, attention has been raised to the significance of flavonoids and their potential role in disease prevention and intervention. Present‐day study efforts in the field of flavonoids mostly focus on the identification of plant‐based or nutritious flavonoids with the objective of investigating their potential medical uses and examining their physiological and pharmacological activity in relation to several chronic disorders.
... efficacy against various human pathogens, including Bacillus cereus [9][10][11][12][13] . Importantly, our recent studies on the microbial stability of natural tea beverages revealed that juice supplements from phenolic-rich and highantioxidant elderberry (Sambucus nigra) and chokeberry (Aronia melanocarpa) fruits, as documented in the literature [14][15][16][17] , differ in their ability to mitigate B. cereus contamination, one of the major bacterial threats identified in association with a recently embraced cold-infusion process 18 . This finding highlights the critical role of the specific composition of berry-derived additives in shaping biopreservation outcomes. ...
... Notably, the predicted logP values for the aforementioned anthocyanins are approximately 0.39, -0.64, and − 1.1, respectively, according to the FooDB database based on ChemAxon software. In this context, the results presented by 17 , who reported the inferior lipophilic antioxidant capacity (L-ORAC FL ) of elderberry and blackcurrant fruits relative to that of chokeberry, provide further support for the suggested concept of B. cereus antibacterial susceptibility to the examined juices and their fractional components (Figs. 1 and 3). Second, the potent antibacterial activity of the anthocyanins derived from blackcurrant juice (Fig. 3C), even when they are applied at concentrations as low as approximately 0.3 µg/mL (d.n.s.), suggests that specific constituents of this juice may limit the effectiveness of cyanidin-3-O-rutinoside and/or other phenolics when used in combination under neutral pH conditions. ...
Ensuring the safety and stability of minimally processed foods using natural preservatives is of great scientific and commercial interest in modern biotechnology. Berry juice supplementation is increasingly recognized within this field. This study investigated the effectiveness of juices from four berry species Aronia melanocarpa, Ribes nigrum, Vaccinium macrocarpon, and Sambucus nigra, against the food pathogen Bacillus cereus. Overall, the antibacterial potency of juice supplements (up to 10% v/v in tryptic soy broth) followed the order of chokeberry > blackcurrant > cranberry > elderberry, with the latter showing no inhibitory effects. Notably, chokeberry and elderberry juices presented lower acidity and significantly greater phenolic contents (p < 0.05) than blackcurrant and cranberry juices did, suggesting that B. cereus susceptibility is not strictly dependent upon low extracellular pH or elevated anthocyanin levels. Instead, it is inferred to correlate with pro-oxidative effects induced directly at the intracellular level. Accordingly, this paper discusses the antioxidative, acidic, and lipophilic attributes of juices and their constituent fractions, including anthocyanins, to elucidate their biopreservative potential. The results of this study increase our understanding of the antibacterial susceptibility of B. cereus.
... Berry fruits are well known for their high content in phenolic compounds, antioxidant capacity, and related health benefits. Particularly, when compared with other berries, elderberry (Sambucus nigra L.) is considered one of the best sources of anthocyanins and presents a powerful in vitro antioxidant activity [10]. Elderberry has long been associated with health benefits [11][12][13]. ...
... Elderberry has long been associated with health benefits [11][12][13]. In addition to their high antioxidant potential [10,[14][15][16], elderberry fruits are described as presenting anti-inflammatory [15,17], antidiabetic [18,19], and antiviral properties [20][21][22] and have a positive impact on obesity and metabolic disorders [23]. In addition to the previously mentioned beneficial health effects, recent studies have also shown that elderberry extracts have prebiotic properties [24][25][26]. ...
One of the food industry’s greatest challenges is to find natural ingredients capable of conferring antioxidant and color properties. In addition, the agri-food industry generates by-products that are often treated as waste, despite their abundance of phytochemicals that can be recovered and used as food ingredients. This study explores the potential of elderberry pomace, an industrial by-product of juice processing rich in anthocyanins and polyphenols, as a natural food additive in blueberry sorbet. Elderberry pomace was incorporated into the sorbet formulation in powder form or as aqueous extracts at two different concentrations. The analysis of the pomace extract by UHPLC-DAD-MS showed the presence of four anthocyanins: cyanidin-3,5-O-diglucoside, cyanidin-3-O-sambubioside-5-O-glucoside, cyanidin-3-O-sambubioside, and cyanidin-3-O-glucoside. The physicochemical properties of the sorbets such as pH, °Brix, overrun, melting rate, and color were evaluated, as well as their levels of total phenolic compounds, total monomeric anthocyanins, and in vitro antioxidant activity. The potential of sorbets to stimulate the growth of probiotic bacteria was evaluated and a sensory analysis was conducted to assess consumer acceptance. Results indicated that the sorbet containing the more concentrated extract presented higher overrun, faster melting rate, higher contents of phenolic compounds and anthocyanins, and higher antioxidant activity compared to the control. Additionally, this formulation showed a darker hue (lower L* value) and a tendency to stimulate probiotic bacteria. Moreover, the sorbets with pomace in their composition had good consumer acceptability. These findings highlight the potential of elderberry pomace to be used as a natural, sustainable ingredient in the ice cream industry, aligning with growing consumer trends towards healthier and eco-friendly products.
... However, while BBs boast a wide range of anthocyanins, with cyanidin-3-glucoside (C3G) being the most prevalent (Elisia et al., 2007;Mazza, 2018), EBs predominantly contain C3G and small amounts of cyanidin 3-sambubioside (C3S) (X. Wu et al., 2004). Furthermore, while BBs are celebrated for their ellagitannins and derivatives, such as ellagic acid, known for their protective effects against cancer and heart diseases (Sangiovanni et al., 2013), EBs harbour various polyphenols, including flavonols, proanthocyanidins, and phenolic acids, which lend them their characteristic black-purple colour and display remarkable biological activity (Anton et al., 2013). ...
... Additionally, two unidentified peaks were found in the EB extract, previously linked to anthocyanins such as C3S and lower levels of cyanidin-3-diglucoside (X. Wu et al., 2004). ...
... Like many other berries, black chokeberries contain significant levels of phenolic compounds, especially flavonoids. As anticipated, they have demonstrated notable antioxidant potential, a characteristics that aligns with the inherent chemical composition of phenolic compounds (Wu et al., 2004). From a biological point of view, anti-inflammatory effects were described in numerous studies (Jurendić &Ščetar, 2021;Ren et al., 2022). ...
... The levels of phenolic compounds in chokeberries vary with reported amounts as high as 37,600 mg/kg of dry mass (Hudec et al., 2006;Oszmiański & Wojdylo, 2005). The dark blue colour of chokeberries is due to its high concentration of anthocyanins, primarily cyanidine derivatives such as cyanidine-3-O-glucoside (Cy3G), -3-O-galactoside, -3-O-xyloside, and -3-O-arabinoside (Wu et al., 2004). Flavonols in chokeberries are mainly quercetin derivatives (such as isorhamnetin, quercetin-3-O-glucoside, -3-O-galactoside, -3-O-rutinoside, -3-O-robinobioside, and -3-O-vicianoside). ...
... Cyanidins, in combination with various glycosides, are the major anthocyanins in Aronia melanocarpa [13]. Analysis of anthocyanin content indicates cyanidin-3-O-arabinoside and cyanidin-3-O-galactoside as the primary anthocyanins [14]. ...
... Cyanidin-3-galactoside is a prominent phenolic compound in Aronia melanocarpa, correlating with enhanced antioxidant and radical-scavenging properties [14]. ...
Aronia melanocarpa, known as black chokeberry, is rich in polyphenols, comprising flavonoids, such as anthocyanins, flavanols, and flavonols, and phenolic acids, such as chlorogenic acid. These polyphenols endow Aronia melanocarpa with preventive and therapeutic properties against various human diseases. Aronia melanocarpa has beneficial effects against diseases such as diabetes, inflammation, and hypertension. Considering the diverse functional components of Aronia melanocarpa, its efficacy in disease prevention and treatment can operate through multiple pathways, offering a more robust approach to disease control. This review covers the latest research results on the functional components of Aronia melanocarpa and their effects on human diseases.
... According to the standard, the retention time and spectra characteristics of Cy-3-glu and Cy-3-rut were confirmed (RC, Table 4). Other peaks of unknown anthocyanins in RC could probably be cyanidin-3-sophoroside, cyanidin-3-glucosyl-rutinoside, cyanidin-3-xylosyl-rutinoside, and cyanidin-3-sambubioside [13,45,46]. The value of total anthocyanins in our case is calculated as the sum of all anthocyanins, as many authors do [4,10,13,14,44,47]. ...
... are affected by the genetic predisposition of the currants, the conditions and method of cultivation, the harvest maturity of the berries, methods of fruit processing (recipe), and storage conditions [13,14]. The occurrence of unknown anthocyanins (derivatives of cyanidin, delphinidin, petunidin, pelargonidin, or peonidin) in black currant concentrates may be due to cultivar selection, natural variability, and formation during chemical transformation due to the production process and storage (elevated temperature and pH, access to oxygen) [40,45,47]. Note: Data are presented as mean ± SD; n = number of samples. ...
The quality of black/red currant products, which are valuable components of a healthy diet, depends on many aspects, e.g., natural variability, climatic conditions, degree of ripeness, processing technology, and recipe. The aim of the study was to assess the effect of the harvest year (2020 and 2021) and different processes (with or without prepress enzymatic treatment) on the chemical composition of 38 laboratory-prepared black/red currant (BC/RC) juices and to compare them with 19 selected commercial products, using 20 compositional and quality markers. Significant differences (p < 0.01) were observed for BC in sucrose, Dp-3-glu, and Cy-3-glu content within the different processes, as well as fructose and ascorbic acid content within the harvest year (p < 0.05). The greatest differences between BC and RC juices were observed in ascorbic acid content (1567 mg/kg in BC and 261 mg/kg in RC), citric acid content (34.6 g/kg in BC and 23.2 g/kg in RC), and in the anthocyanin profile. The major anthocyanins of the currant products were identified as Dp-3-rut (39.1–50.4%), Cy-3-rut (30.1–39.1%), Cy-3-glu (3.6–18.2%), and Dp-3-glu (9.4–13.5%) in BC and Cy-3-glu (59.3–67.2%) and Cy-3-rut (14.2–19.8%) in RC. The chemical composition of commercial products was found to be highly variable and dependent on the recipe used.
... This is also the main reason for the bitter taste of the fruit [20]. Proanthocyanidins exist in the form of monomers (0.78%), dimers (1.88%), trimers (1.55%), 4-6-mers (6.07%), 7-10mers (7.96%), and those of more than 10 polymers (81.72%) [21]. Zhu et al. [22,23] used response surface methodology to optimize the extraction process of proanthocyanidins and obtained a proanthocyanidin content of 3.32% in Aronia melanocarpa. ...
... This is also the main reason for the bitter taste of the fruit [20]. Proanthocyanidins exist in the form of monomers (0.78%), dimers (1.88%), trimers (1.55%), 4-6-mers (6.07%), 7-10-mers (7.96%), and those of more than 10 polymers (81.72%) [21]. Zhu et al. [22,23] used response surface methodology to optimize the extraction process of proanthocyanidins and obtained a proanthocyanidin content of 3.32% in Aronia melanocarpa. ...
Aronia melanocarpa fruit contains a variety of active ingredients, such as phenolic acids, anthocyanins, proanthocyanidins, etc. Relevant in vivo and in vitro studies have concluded that it has beneficial effects in terms of treating dyslipidemia, hypertension, glucose metabolism disorders, etc. This article discusses the nutritional value and food processing of Aronia melanocarpa and reviews the chemical components of Aronia melanocarpa and the pharmacological activities of related substances in order to summarize the chemical characteristics of the fruit and its development prospects. The process optimization of juice production, the impact of antioxidant capacity, and the comprehensive utilization of pomace in feed are discussed. This article provides a reference for future comprehensive application research and product development of Aronia melanocarpa.
... 46,47,52,62,69] Ÿ Phenolic acids -lignan's and stilbenes in vegetables and whole grains. Ÿ Other -resveratrol in red wine and ellagic acid -berries [ 1 , 3 , 8 , 9 , 2 0 , 2 2 , 2 9 , 3 5 , 3 6 , 4 0 , 4 1 , 5 1 , 5 4 , 5 8 , 6 4 , 6 7 , 7 6 ] Flavonoids are phenolic [9,17,18,21,29,46,47,52,62,69], [1] compounds secondary metabolites' ,sub divided [ 9 ] [ 1 4 , 1 8 , 1 9 , 2 9 , 3 1 ] into 6 types -Isoavonoids ,avanols and [9,29,68,71] anthocyanidins present in green biota. 1. Wide variety of anticancer effects -reactive oxygen speciesinduce apoptosis,autophagy,inhibit the action of cancer cell [2,3,9,11,13,27,28,29,38,48,66,74,75,76] proliferation and cell cycle ,invasiveness 2. Dual action -Homeostasis -potent pro-oxidants in cancer cells activates the apoptotic pathways and downward pro inammatory [2,3,9,11,13,27,28,29,38] signaling pathway. ...
... Chemical structures : Flavonoids formed by the basic avan skeleton -15 carbon phenylpropanoid (C6-C3-C6 system) two aromatic ring linked by a heterocyclin pyran ring,degree of oxidation and linking [9] chain unsaturation avonoids avanones , [1,38,9,20,22,29,35,36,40,41 ,51,54,58,64, 67,76] , [14,18,19,29,31], [9,29,68,71] avanols avones and anthocyanidins. (Fig 1) [ [9,29,43,74,77,78] [ 32,45] Hesperetin and naringenin are two main avonones ( Fig 3) [7,9,29,50,55,66,72] Flavanols Contains Quercetin and kaempferol, myricetin . ...
... Hence, the higher levels for FRAP found in the tisanes with GA than that of the roselle tisane alone are likely a reflection of higher levels of total phenolic content, which contributed to the antioxidant properties. The present study is in accordance with the study on 22 different vegetables by Wu et al. (2004) and Volden et al. (2009), who found a strong correlation between total phenolic content and antioxidant capacity. The values of FRAP in tisanes with GA showed a pattern similar to the changes in total phenolic content. ...
Roselle (Hibiscus sabdariffa) is rich in antioxidants and phenolic compounds, especially anthocyanins, which have shown therapeutic potential. The anthocyanin content in roselle tisane would increase in an acidic solution, thus enhancing its antioxidant properties and colour intensity. This study was carried out to investigate the influence of adding different ratios of Garcinia atroviridis on the pH, colour, anthocyanin content, and antioxidant properties of roselle tisane. The ratio of roselle: Garcinia atroviridis (GA) (w/w) studied was 2:0, 2:1, 2:2 and 2:3. The results showed that the pH was decreased as the amount of GA increased, hence increasing 25% of the anthocyanins content of roselle tisane. Furthermore, the colour of the tisane with GA became bolder and more saturated, as indicated by the increase in colour values (L*, a*, b*, chroma, and hue angle) with higher levels of GA. Results of antioxidant properties (total polyphenol, total flavonoid and ferric reducing antioxidant power assay) also showed an increment as the amount of GA increased. Conversely, the DPPH assay demonstrated a 17% decrease in the percentage of inhibition as the amount of GA increased. Roselle tisane infused with GA displayed weakened radical scavenging abilities, as indicated by higher IC50 values. However, all samples exhibited effective antioxidant activity, with IC50 values below 1 mg/mL. In conclusion, adding GA to the formulation could affect the properties of roselle tisane. The higher content of GA in the formulation significantly increased the anthocyanin content and antioxidant activities of the roselle tisane.
... The major anthocyanin was C3G, identified via the HPLC analysis. Similar results were obtained by Djordjevic [11] and Wu [37], where C3G was found to be predominant but at a lower concentration than in our study. The amount of C3G was 155.38 ± 7.34 mg/100 g in RPLJ and 34.3 ± 4.55 mg/100 g in RPJWE. ...
Red currant (Ribes rubrum L.) berries are rich in bioactive compounds and exhibit nutritive and protective features. This research examined the content of secondary metabolites of the red currant variety Redpoll lyophilized juice and waste extract and their antioxidative and spasmolytic effects. The flavonol and anthocyanin contents of the samples were determined using high-performance liquid chromatography. The antispasmodic effects were assessed in in vitro conditions, and the potential impact of the samples and possible action mechanisms were revealed. The results showed the prevalence of cyanidin-3-O-glucoside as the dominant anthocyanin with higher content in the juice sample. Quercetin content, as the prevalent flavonol, was higher in the waste sample. The berry juice showed a greater ability for scavenging free radicals, whereas the waste better inhibited lipid peroxidation. The juice was a superior antispasmodic agent for spontaneous, KCl-, CaCl2-, BaCl2-, histamine-, and acetylcholine-induced ileal contractions. This first evaluation of the red currant variety Redpoll lyophilized juice and waste extract indicated the beneficial effects of juice as an antioxidant and spasmolytic agent. Therefore, this red currant juice sample could be designated for the prevention or treatment of gastrointestinal disorders.
... The phenolic constituents in chokeberries mainly contribute to their strong antioxidant activities which include radical scavenging activities and TEAC [20]. From different studies, it has been observed that there is a positive correlation between the total phenolic content present and the oxygen radical scavenging activity and TEAC values of different berries [24]. Apart from their radical scavenging abilities, procyanidins as well as anthocyanins are known to contain o-dihydroxyphenyl groups which possess metal chelating [25]. ...
Purpose of Review
Berries are a great source of fiber, polyunsaturated fatty acids, and beneficial secondary metabolites (polyphenols). Various phytochemicals present in berries (glycosidic-linked flavonoids, anthocyanins, etc.) provide potential health benefits to consumers. Berries are known as high antioxidant food which provides certain cellular and molecular protection thereby lower rates of obesity and chronic disease risk. Molecular-level mechanisms protect a cell, while cellular mechanism considers all molecular units. For example, polyphenols found in blueberries have the potential to significantly reduce adipogenesis. Therefore, in continuation with part I, this review part II summarizes recent updates on the nutritional composition and biological activities of caperberry, chokeberry, cloudberry, cranberry, elderberry, gooseberry, goji berry, and lingonberry.
Recent Findings
These berries contain higher amounts of dietary fiber, protein, polyphenols, vitamins, minerals, and lipids. Besides, their antioxidant and anti-inflammatory activities, these berries are reported for eye health, brain health, cardiovascular health, anti-diabetic, etc.
Summary
The consumption of a summarized group of berries could be more beneficial for eye health, mental health, and metabolic health thereby enhancing the well-being of the consumers.
... (Aronia melanocarpa) (Wu et al., 2004;Chrubasik et al., 2010). ...
... Particularly, Aronia berries, also known as black chokeberries, are edible fruits that resemble cherries [32]. Aronia berries have gained significant attention because of their abundant polyphenol content, particularly anthocyanins, which can comprise up to 1.5% of their fresh weight [33]. The Aronia fruit extract reportedly exhibits anti-inflammatory effects [34][35][36][37], whereas the dry extract reduces the secretion of pro-inflammatory cytokines, such as TNF-α and IL-1β, in LPS-stimulated macrophages [35]. ...
Background/Objectives: Aronia extract or its active compounds, especially anthocyanin, have shown potential for Alzheimer’s disease (AD)-related pathologies, including neuroinflammation, fibrillogenesis of amyloid beta (Aβ), and cognitive impairment. However, there was still concern about their structural instability in vivo and in vitro. To solve the instability of anthocyanins, we combined aronia bioactive factions (ABFs) and alginic acid via electrostatic molecular interactions and created an ABF–alginic acid nanocomplex (AANCP). We evaluated whether it is more stable and effective in cognitive disorder mice and neuroinflammation cell models. Methods: The physicochemical properties of the AANCP, such as nanoparticle size, structural stability, and release rate, were characterized. The AANCP was administered to scopolamine-injected Balb/c mice, and to BV2 microglia treated with lipopolysaccharide (LPS) and amyloid beta (Aβ). Inflammation responses were measured via qPCR and ELISA in vitro, and cognitive functions were measured via behavior tests in vivo. Results: The AANCP readily formed nanoparticles, 209.6 nm in size, with a negatively charged zeta potential. The AANCP exhibited better stability in four plasma samples (human, dog, rat, and mouse) and was slowly released in different pH conditions (pH 2.0, 7.4, and 8.0) compared with non-complexedABF. In vitro studies on microglial cells treated with AANCPs revealed a suppression of inflammatory cytokines (tumor necrosis factor-alpha and interleukin-6) induced by LPS. The AANCP increased microglial Aβ phagocytosis through the activation of triggering receptor expressed on myeloid cell 2 (TREM2)-related microglial polarization. The AANCP inhibited aggregation of Aβ in vitro and alleviated cognitive impairment in a scopolamine-induced in vivo dementia mouse model. Conclusions: Our data indicate that AANCPs are more stable than ABFs and effective for cognitive disorders and neuroinflammation via modulation of M2 microglial polarization.
... Optimisation of concentrations to avoid excessive flavour intensity and interactions between polyphenols and other ingredients, which may affect stability and release [285][286][287][288] Health Benefits ...
Microencapsulation of polyphenols is an innovative approach in food technology by which to protect these bioactive compounds from degradation and increase their bioavailability. Polyphenols, naturally occurring in plants, exhibit potent antioxidant, anti-inflammatory and anticancer properties, which make them valuable functional ingredients in foods. However, their susceptibility to external factors, such as light, temperature and pH, presents a significant challenge for their incorporation into food products. Microencapsulation, based on various techniques and carriers such as polysaccharides, proteins and lipids, allows polyphenols to be stabilized and released in a controlled manner in the digestive system. This article reviews the different microencapsulation techniques, carrier properties, and the applications of microencapsulated polyphenols in food products, including bakery, dairy and functional beverages. Additionally, the article discusses the benefits and challenges associated with this technology, highlighting its potential to improve the stability, nutritional value and sensory acceptance of food products.
... al, 2007;McKay, 2004]. The fruit of black chokeberry has higher levels of antioxidants than any other temperate fruit [Wu et al, 2004]. Fresh fruits of aronia are an amazing source of vitamin C and polyphenols, including proanthocyanidins, anthocyanins and flavonoids, vitamins B (B1, B2, B6, niacin and pantothenic acid), β-carotene [Benvenuti et al., 2004;Jeppsson and Johansson, 2000;Kulling et al., 2008;Tanaka and Tanaka, 2001;Walther and Schnell, 2009]. ...
The effects of osmotic treatment and convective dehydration on organic fruits of Aronia melanocarpa L.
were analysed. The classical dehydration needed 30 hours at 60˚C. In case of osmotic treatment, the
dehydration acquired 8 hours at 60˚C. The ratio between fruits and solution was 1:2 and 1:3. The osmotic
solution contained concentrated sour cherry & apple juice and organic inulin. Weight reduction, amount of
carbohydrates, vitamin C and total phenols varied upon the method of dehydration, ratio and fruits integrity. Best
results were obtained using the osmotic treatment, at the ratio 1:2 on pricked fruits.
... 9 The distinctive color of the aronia can be attributed to the fruit's content of anthocyanins. 10 Glycosylation of anthocyanins generally occurs on the 3-hydroxyl of the anthocyanin molecule; however, it can also occur in the 5 or 7 positions of flavylium ions. 11 Figure 1 displays the common structure of anthocyanins at a pH of ∼3.6, the natural pH of aronia juice. ...
Aronia mitschurinii is a cultivated species originating from crossbreeding the wild species Aronia melanocarpa, also known as the black chokeberry, and European mountain ash Sorbus aucuparia. The aronia fruit is dark purple, which can be attributed to the high content of anthocyanins, other flavonoids, and polyphenols. Aronia’s reputation as a superberry entices small farms to use it as a prospective specialty crop. The fruit’s high antioxidant content is a likely ingredient in several new products, such as jellies, jams, vitamin supplements, and beverages. Food applications of any fruit require high-temperature pasteurization as a major step in fruit processing. Many also require cooking. However, there are some major effects higher temperatures may have on antioxidants, such as isomerization and decomposition, both of which result in a loss of bioavailability of these key compounds. Here, we present a detailed investigation of the effect of temperature and time on the antioxidant content of Aronia mitschurinii juice and power aid drink. UV/vis methods were used to determine the total concentrations of anthocyanins, flavonoids, polyphenols, and tannins and to determine the optimal pasteurization and/or thermal processing conditions that would prevent significant loss in the antioxidant content in aronia products.
... Similar to HuR, an RNAbinding protein, SIRT1 promotes MAT2B transcription while improving MAT2B mRNA stability. [15] In addition, resveratrol lessens MAT's connections with MAT2 and increases MAT's connections to HuR and SIRT1. The interaction between SIRT1, MAT, and HuR enhances the stability of these proteins, but MAT reduces the Ki of MAT2 for S-adenosylmethionine. Resveratrol suppresses growth and encourages apoptosis by upregulating MAT2B and downregulating MAT2BV1. ...
The anticancer activity of resveratrol is well known. But because of its limited water solubility and lowbioavailability, resveratrol (RES) is a BCS class II medication with research potential. The current work createsa new copolymer from Lipoid S-75 and chitosan and tests the RES-loaded micelles it produces for varieddelivery properties. In addition to efficiently loading the drug, the nanometric micellar carriers also regulatedthe rate of RES release. The discoveries using a novel polymer-based carrier show promise for improvedmedication delivery in the future. Aim: The aim of the study was to synthesize and characterize the lipoid S-75conjugated chitosan-based micelles for improving biopharmaceutical parameters of resveratrol. Methods: Thepreparation and characterization of a copolymer of CS and lipoid S-75 were done by using S-75 100 mg andDCC 700 mg which is followed by preparation and characterization of CS-lipoid S-75-conjugated resveratrolmicelles. And evaluation of the formulation done by the parameters such as particle size, polydispersityindex zeta potential, % encapsulation efficiency and drug loading, drug loading capacity, and differentialscanning calorimetry. Results: In the present study, development of polymeric micelles using the flavonoidin multifaceted applications, entailing therapy, diagnostics, in-suit imaging, and on-demand drug delivery,resveratrol, polymers such as chitosan, and lipoid S-75 show significant potential. The fundamental formationmechanisms are then analyzed, focusing on the inherent physicochemical qualities like solubility andbioavailability that control the drug release. Conclusion: The development of resveratrol-loaded chitosanbasedS-75 micelles demonstrates considerable potential for multifaceted biomedical applications, includingtherapy, diagnostics, in-situ imaging, and on-demand drug delivery. The combination of resveratrol, chitosan,and lipoid S-75 results in a polymeric micellar system with enhanced solubility and bioavailability, addressingthe challenges associated with the poor aqueous solubility and rapid metabolism of resveratrol. The analysisof the micelle formation mechanisms highlights the crucial role of the inherent physicochemical propertiesin controlling drug release. This innovative micellar platform offers promising avenues for optimizing thetherapeutic delivery of resveratrol and broadening its application scope in pharmaceutical and biomedicalfields.
... Among them, B2 is a common type of flower found in Sorbus nigra. cyanins(Sidor et al., 2019;Esatbeyoglu & Winterhalter, 2010;Wu et al., 2004), so PCA-B2 was used for molecular docking experiments in this study. ...
... Among the dark berries, chokeberries contain by far the highest amount of proanthocyanidins with up to 664 mg/100 g fresh weight, where mainly OPCs with a DP of 4-10 and >10 are represented. In comparison, the total proanthocyanidin content of blueberries and blackberries is only 27-148 mg/100 g fresh weight [13,14]. Based on the high content of OPCs, chokeberries are attributed strong antioxidant potential. ...
Chokeberries, which belong to the rose family (Rosaceae), have received increasing research attention due to their high content of secondary metabolites, especially oligomeric proanthocyanidins (OPCs). OPC-rich extracts are attributed to various positive health effects, including antioxidant or anti-inflammatory properties, which is why they are sold as food supplements. However, knowledge about the antioxidant properties of single OPCs is quite limited. Several separation steps with different separation techniques were performed to isolate OPCs from a pre-produced extract. More than 90 analytes were detected in the enriched fractions, which include eight OPCs, four cinchonains and one hexoside, including their respective isomers. For the characterization of the OPCs, high-resolution mass spectrometry coupled with liquid chromatography (LC-HRMS) was used. Based on the fragment spectra of the MS² experiments, conclusions about the fragmentation pathways and the structure of six new OPCs could be drawn. After isolating trimers, tetramers and pentamers, it was possible to test the antioxidant effect in relation to the individual degrees of polymerization (DP) or structures. The Trolox-equivalent antioxidant capacity (TEAC) test showed that all OPCs investigated exhibit antioxidant effects and a first correlation between the antioxidant effect and the DP could be postulated, which suggests new possibilities for the design of food supplements.
... mg 100 g -1 FW), pomegranate (15-252 mg 100 g -1 FW) were rich in anthocyanins (ĆUJIĆ et al., 2013;DENEV et al., 2018;CEVALLOS-CASALS et al., 2022). Chokeberry (Aronia melanocarpa) have higher content of flavonoids including total anthocyanins and proanthocyanidins, and higher antioxidant activity compared to compared to blackcurrant (Ribes nigrum), red currant (Ribes rubrum), gooseberry (Ribes grossularia), strawberry (Fragaria anannassa), blackberry (Rubus fruticosus), blueberry (Vaccinium sp.) and red raspberry (Rubus idaeus) (JURIKOVA et al., 2017;WU et al., 2004). Autochthonous pomegranate varieties content average 323.78 mg kg -1 FW anthocyanins (IQBAL et al., 2010). ...
The objective of this study was to analyze the content of vitamin C, total phenols, total anthocyanins, flavan-3-ols and antioxidant activity in fruits of five berry fruit species: blackcurrant variety ?Rosenthal?, white mulberry local ecotype, black chokeberry variety ?Viking?, blackberry variety ?Thornfree? and pomegranate autochthonous variety ?Karamustafa?. Determination of vitamin C was performed by classical analytical method. Total phenols, total anthocyanins, flavan-3-ols and antioxidant activity were analysed by spectrophotometric methods. The obtained results from the analysis for berry fruits showed high antioxidant activity, over 70% and high content of polyphenols. According to the genotype, black chokeberry had the highest content of total phenols (23.9 mg g-1 FW (fresh weight), anthocyanins (6.1 mg g-1 FW) and flavan-3-ols (2.8 mg g-1 FW). Blackcurrant had highest content of vitamin C (216.0 mg 100 g-1 FW) and antioxidant activity (86.2% inhibition). A positive correlation was found among all the studied fruit species. A strong positive correlation of vitamin C with antioxidant activity was determined, as well as between total phenols and total anthocyanins, i.e. flavan-3-ols. A weak negative correlation was only observed for catechin in relation to vitamin C, inhibitory antioxidant activity and vitamin C antioxidant activity.
... В литературата липсват данни за ORAC и HORAC на сок от Aronia melanocarpa, но има данни за ORAC на плодове (19,20) и екстракт (3), и за HORAC на екстракт (3). ORAC на арониевите плодове е много по-висок от този на други пло-дове. ...
Aronia melanocarpa is a woody shrub of the Rosaceae family. Its fruits are used for consumption either fresh, or as juice, jam and wine. The aim of the present study was to measure the concentration of some biologically active substances and the antioxidant activity of two samples of Aronia melanocarpa fruit juice (AMFJ). The juice was prepared from fresh fruits. One of the samples was produced using a juice centrifuge and was preserved with potassium sorbate (1.0 g/l). The other sample was produced by crushing and squeezing of fruits after which the juice was filtered and sterilized at 100 °C for 10 min. The contents of biologically active substances in the juice samples were measured by spectrophotometric and high-performance liquid chromatography methods. The antioxidant activity of the two juice samples was measured by the ORAC (oxygen radical absorbance capacity) and HORAC (hydroxyl radical аverting capacity) methods. The results showed that both samples were extremely rich in polyphenolic substances, amongst which the highest was the concentration of procyanidins followed by phenolic acids (chlorogenic and neochlorogenic) and anthocyanins. Sample 1 had higher concentration of total phenolics and contained higher quantities of most polyphenolic substances with the exception of anthocyanins. It also contained micro-quantities of cyanogens. The variations in the composition of the two samples could be attributed to the different methods of juice production and conservation. Both juice samples showed very high ORAC and HORAC values which were higher for sample 1 (the sample with the higher concentration of polyphenolic substances). The high antioxidant activity of the two AMFJ samples could be attributed to their polyphenolic ingredients.
... In addition, to our knowledge, this study marks the first time that pelargonidin 3-sambubioside has been identified and quantified in black carrot. This compound has been previously identified in different berry fruits [28,29]. ...
Black carrot (Daucus carota ssp. sativus var. atrorubens Alef.) is widely recognized for its bioactive compounds and antioxidant properties. The black carrot of Cuevas Bajas (Málaga) is a local variety characterized by a black/purple core, which differs from other black carrot varieties. Therefore, this autochthonous variety was characterized according to the root size and the harvesting season by means of a study of its antioxidant capacity analyzed by three methods, its total carotenoids content, and its sugars and phenolic compounds profile by ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-MS). A total of 20 polyphenolic compounds were quantified in 144 samples analyzed. The anthocyanidins group was observed to be the most abundant, followed by the hydroxycinnamic acids group. Moreover, pelargonidin 3-sambubioside was observed in black carrot for the first time. The medium-sized carrots presented the highest content of phenolic compounds, largely due to their significantly higher anthocyanidins content. Comparatively, the small carrots showed a higher content of simple sugars than the large ones. Regarding the influence of season, significantly higher quantities of glucose and fructose were observed in the late-season carrots, while sucrose was the main sugar in early-season samples. No significant differences were observed in the total carotenoid content of black carrot.
... Polyphenolic compounds known as favonoids, which have a basic C 6 -C 3 -C 6 structure (Figure 2(a)) [26], are abundant in foods like green tea and chocolate [27]. Apples [28,29], plums, cherries [28,30], berries [31,32], olives [33], onions [34], beans [35], spinach [36], and shallot [37] are also rich sources of favonoids. Flavonoids have demonstrated anticancer efects by downregulating the cell cycle process, cell proliferation, and invasiveness behavior of tumor cells. ...
Background
Janus-activated kinase 2 (JAK2) plays a pivotal role in numerous essential biological processes, including proliferation, apoptosis, and metastasis in human cells. Prior studies have indicated that inhibiting JAK2 could be a promising strategy to mitigate cell proliferation and induce apoptosis in tumor cells.
Objectives
This study aimed to estimate the binding affinity of 79 herbal compounds, comprising 46 flavonoids, 21 anthraquinones, and 12 cinnamic acids, to the ATP-binding cleft of JAK2 to identify potential herbal inhibitors of JAK2.
Methods
The binding affinities between ligands and JAK2 were calculated utilizing AutoDock 4.0 software in conjunction with the Cygwin environment. Cross-validation was conducted using the Schrödinger tool. Molecular dynamics simulations were employed to evaluate the stability of docked poses for the most significant JAK2 inhibitors. Furthermore, the Discovery Studio Visualizer tool was utilized to elucidate interactions between the top-ranked JAK2 inhibitors and residues within the JAK2 ATP-binding site.
Results
Twelve flavonoids, two anthraquinones, and three cinnamic acids demonstrated substantial binding affinities to the protein kinase domain of the receptor, with a criterion of ΔGbinding < −10 kcal/mol. Among the studied flavonoids, anthraquinones, and cinnamic acid derivatives, orientin, chlorogenic acid, and pulmatin emerged as the most potent JAK2 inhibitors, exhibiting ΔGbinding scores of −14.49, −11.87, and −10.76 kcal/mol, respectively. Furthermore, the docked poses of orientin, pulmatin, and chlorogenic acid remained stable throughout 60 ns computer simulations. The average root mean square deviation values calculated for JAK2 when complexed with orientin, chlorogenic acid, and pulmatin were 2.04 Å, 2.06 Å, and 1.95 Å, respectively.
Conclusion
This study underscores the robust inhibitory potential of orientin, pulmatin, and chlorogenic acid against JAK2. The findings hold promise for the development of novel and effective drugs for cancer treatment.
... The most likely reason for its slow spread throughout Europe is the astringent taste of the berry [2]. Notwithstanding their taste, the berries have high levels of vitamins, flavonoids, tannins and other substances beneficial in improving the human immune system [3,4]. Many scientific studies in the fields of nutrition and medicine have proved the positive effect of chokeberry fruit in preventing cardiovascular diseases and treating colon cancer, uveitis and many other diseases [5][6][7]. ...
Plant samples were collected in March 2012 using the sampling method defined in (ISO 10381: 3, 2001), and delivered to the Laboratory, of Faculty of Agronomy, from Caèak for analysis. Black chokeberry was grown on four types of soil viz. Luvisol, Pseudogley, Fluvisol and Vertisol. The total sugar content was highest in black chokeberry fruits sampled from the Vertisol, followed by those grown on Luvisol, Fluvisol and Pseudogley soils. Black chokeberries were found to contain sorbitol, a sugar alcohol, which is not a characteristic common to other berries. The dominating organic acids in black chokeberry fruits include malic acid and citric acid, regardless of soil type. The fruits are rich in vitamin C content-0.2 g/L, irrespective of soil type.
... ± 0.58 mg cyanidin-3-glucoside Kg −1 of extract. This value was found to be lower than that in black chokeberry, Aronia melanocarpa (1480 mg cyanidin-3-glucoside Kg −1 extract; [35]) and purple corn, Zea mays L. (1642 mg cyanidin-3-glucoside Kg −1 extract; [36]) and higher than that in cutleaf blackberry, Rubus laciniatus (589 mg cyanidin-3-glucoside Kg −1 extract; [37]), blackberry, R. L. Hybrids (317 mg cyanidin-3-glucoside Kg −1 extract; [38]), Red Cabbage, Brassica oleracea (150 mg cyanidin-3-glucoside Kg −1 extract; [39]), and grape, Vitis vinifera (60 mg cyanidin-3-glucoside Kg −1 extract; [40]). These different anthocyanin values may be attributed to characteristics such as plant species, origin, age, and harvest season. ...
This study aimed to use common mallow (Malva sylvestris) extract (EMS) with ratios of 0.0, 0.5, 1.0, and 2.0% as an indicator in the film produced from corn starch/tragacanth gum matrix using a casting method to monitor the freshness of Nile tilapia fillets stored at 4 °C. The results showed that the total anthocyanin content of EMS was 1185.6 ± 0.58 mg cyanidin-3-glucoside Kg⁻¹. The starch/tragacanth gum films incorporated with 0.5 and 1.0% EMS were sensitive to the 0.8 and 1.4 M ammonia and their color changed after 20 min of exposure, while starch/tragacanth gum film incorporated with 2.0% EMS showed no visible color change in the presence of 0.2, 0.8 and 1.4% M ammonia. The Fourier transform infrared and X-ray diffraction spectra of the colorimetric films showed that EMS was successfully immobilized into the starch/tragacanth gum matrix. The moisture content and water solubility were significantly lower in the films containing EMS compared to those with no EMS supplementation. With increasing EMS concentration, water vapor permeability and ultimate tensile strength significantly decreased with the lowest values observed in films incorporated with 2.0% EMS (p < 0.05). The color of the starch/tragacanth gum films incorporated with 0.5 and 1.0% EMS was changed with a decrease in the quality and freshness of Nile tilapia fillet from pink to green and gray, respectively, after 12 days of storage at 4 °C. Findings of the present study illustrated that the pH-sensitive starch/tragacanth gum film incorporated with 0.5–1.0% EMS could be used as a halochromic indicator in the smart packaging of Nile tilapia fillet.
... Elderberry contains numerous bioactive and immune-modulating compounds [21], including lectins with direct anti-viral properties [22]. Elderberry is also rich in polyphenolic compounds including anthocyanins, which contribute to the color of the fruit and have potent antioxidant and anti-inflammatory properties [23][24][25][26][27]. Flavonoids also contribute immune-modulating effects, binding directly to viral agents and preventing their recognition and entry into cells [28]. ...
Immune cells express Pattern Recognition Receptors (PRRs) to recognize potentially pathogenic microbial forms. Nutraceutical compounds can induce immune cell activation through PRRs. The nutraceutical immune blend (IB), QuickStart™, contains botanical and yeast-derived ligands for PRRs, along with vitamin C and zinc. We evaluated immune-activating effects of the IB and its ingredients in vitro. Human peripheral blood mononuclear cells were treated with either the IB or single ingredients: elderberry extract, the proprietary Saccharomyces cerevisiae fermentate EpiCor™ (Sacc), the plant-based hemicellulose preparation Natramune (PDS-2865)™ (Hemi), vitamin C (VitC), or zinc gluconate (Zinc). The IB triggered sequential waves of immune activation. Initial cytokine induction by the IB at 2 h involved the immune-activating cytokines IL-6, IL-8, MIP-1α, and TNF-α, and the stem cell-mobilizing growth factor G-CSF, as did Sacc and Hemi. The 24 h immune-activation by the IB included increases in IL-1β, IL-17A, IP-10, GM-CSF, Basis FGF, PDGF-BB, and the anti-inflammatory cytokine IL-10. Increased CD69 expression by the IB was also seen for VitC and Sacc. Increased CD25 expression by the IB on monocytes was also seen for Sacc. The IB triggered rapid immune activating events of higher magnitude than the single ingredients, involving immune-activating cytokines and restorative growth factors. Clinical research is warranted to evaluate rapid immune-modulating events upon consumption.
... However, the total monomeric anthocyanin content of Nero in our study was higher compared to that recorded in Viking. Our findings (418.78-794.63 mg/100 g) are within the range of total monomeric anthocyanin content reported by Zheng and Wang (2003) and Wu et al. (2004), who showed that the total mono-meric anthocyanin content of chokeberry was between 237 and 990 mg/100 g. ...
Introduction. Aronia × mitschurinii A. K. Skvortsov & Maitul. is a cultigenic species bred in the late 19th century as a result of breeding work by I. V. Michurin by crossing Aronia melanocarpa (Michx.) Elliott with distantly related species of the rowan genus ( Sorbus ). The fruits of this plant have long been used in folk and traditional medicine, being, first of all, a source of anthocyanin compounds. The leaves are currently only a by-product in the preparation of fruits, however, they can be used as a promising source of such groups of biologically active substances as flavonoids, tannins, leucoanthocyanins, which makes it possible to use this raw material to obtain herbal medicinal products (HMP). Therefore, primary in vitro screening studies to assess the toxicity and biostimulating effect of extracts from the leaves of Aronia michurini should be considered relevant to assess the prospects and determine the directions of subsequent preclinical trials. The aim of the study was to investigate the biostimulating and membrane-protective effect of Michurin's chokeberry leaf extracts (using a decoction as an example) in vitro using the Parame с ium caudatum ciliate test system in the «functional load» test.
Materials and methods. Michurin's chokeberry leaves were harvested for the study at different periods of leaf blade development (May, June, August and September 2023) from plants cultivated on the territory of the I. V. Michurin Federal Scientific Center (Michurinsk, Tambov Region). For the study, aqueous extracts were prepared from the studied raw materials as a decoction in accordance with general pharmacopoeial monograph.1.4.1.0018.15 «Infusions and decoctions» for raw materials containing tannins. To study the biostimulating effect of the decoction of Michurin's chokeberry leaves, an in vitro test system of Parame с ium caudatum ciliates in the stationary growth phase was used. The biostimulating and membrane-protective effect of the studied decoction was assessed in the «functional load» test under the damaging effect of a hypertonic sodium chloride solution.
Results and discussion. Using the test system of the Parame с ium caudatum ciliates in the «functional load» test, it was established that a decoction of Michurin’s chokeberry leaves in vitro in a 1 : 10 dilution at all times of the medicinal plant raw material preparation reduces the survival time of ciliates under the damaging effects of a hypertonic sodium chloride solution during an incubation of 24 hours by no less than 43.5 % compared to the control sample, which probably indicates an increase in the permeability of biological membranes under the influence of tannins and sterols of the leaves and is consistent with their known astringent and antibacterial action. A decoction of Michurin's aronia leaves (when harvesting medicinal plant raw materials in June) in vitro in dilutions of 1 : 1000 and 1 : 10 000 close to the ranges of therapeutic doses, exhibits the greatest biostimulating and membrane-protective effect, which is confirmed by a significant reliable increase in the survival time of ciliates under the damaging effects of hypertonic sodium chloride solution, by a maximum of 39.3 % compared to the control sample during 24 h incubation, which is probably associated with the content of flavonoids and leucoanthocyanins and is consistent with their known capillary-protective and antioxidant effects.
Conclusion. A decoction of Michurin's chokeberry leaves (diluted 1 : 1000 when harvesting medicinal plant raw materials in June) significantly and reliably increases the survival time of the Parametium caudatum ciliate test system under the damaging effects of sodium chloride solution in the «functional load» test, by a maximum of 39.3 % compared to the control sample during 24-hour incubation, which indicates the presence of a biostimulating and membrane-protective effect.
Pyropia haitanensis (T.J. Chang and B.F. Zheng) undergoes periodic dehydration and rehydration cycles, necessitating robust adaptive mechanisms. Despite extensive research on its physiological responses to desiccation stress, the comprehensive metabolic pathways and recovery mechanisms post-rehydration remain poorly understood. This study investigated the metabolic responses of P. haitanensis to varying degrees of desiccation stress using LC-MS and UPLC-MS/MS. Under mild dehydration, the thallus primarily accumulated sugars and proline, while moderate and severe dehydration triggered the accumulation of additional osmoprotectants like alanine betaine and trehalose to maintain turgor pressure and water retention. Concurrently, the alga activated a potent antioxidant system, including enzymes and non-enzymatic antioxidants, to counteract the increased reactive oxygen species levels and prevent oxidative damage. Hormonal regulation also plays a crucial role in stress adaptation, with salicylic acid and jasmonic acid upregulating under mild dehydration and cytokinins and gibberellin GA15 accumulating under severe stress. Rehydration triggered the recovery process, with indole acetic acid, abscisic acid, and jasmonic acid promoting rapid cell recovery. Additionally, arachidonic acid, acting as a signaling molecule, induced general stress resistance, facilitating the adaptation of the thallus to the dynamic intertidal environment. These findings reveal P. haitanensis’ metabolic adaptation strategies in intertidal environments, with implications for enhancing cultivation and stress resistance in this economically important seaweed.
Introduction. Recently, researchers have shown great interest in studying the phytochemical composition of Michurin's aronia leaves (Aronia × mitschurinii A.K. Skvortsov & Maitul) due to the significant content of such valuable biologcally active substances (BAS) as flavonoids, leucoanthocyanins and tannins of the condensed group. Considering the high potential astringent, capillary-protective and anti-inflammatory activity of the main target groups of the BAS of the studied raw materials, in the framework of the present study we have analysed the antimicrobial activity of aqueous-alcoholic liquid extracts of the medicinal forms from Michurin's chokeberry leaves. In our recent studies, we have also established the biocidal effect of the decoction in vitro at a dilution of 1 : 10 on the test system of infusoria Parametium caudatum under the damaging effect of sodium chloride solution in the test "Functional load".
Aim. The purpose of the work was to determine the antimicrobial activity of aqueous-alcoholic liquid extraction dosage forms obtained from the leaves of chokeberry Michurin, in order to assess the prospects for creating medicinal herbal preparations (MHRP).
Materials and methods. The object of the study were liquid extraction dosage forms, tincture (1 : 5) and liquid extract (1 : 1), obtained from dried leaves of Michurin's chokeberry using 60 % ethanol. The antimicrobial activity of the samples was determined by the double serial dilution method. Staphylococcus aureus, Bacillus cereus, Candida albicans, Escherichia coli , Pseudomonas aeruginosa strains were used as test cultures. The prediction of the main types of pharmacological activity by in silico method was carried out for the pre-identified components of the leaf polyphenolic complex – catechin, rutin and leucocyanidin – using PassOnline and Phyto4Health platform. The medicinal forms obtained were standardised in accordance with the requirements for tinc-tures and extracts of the State Pharmacopoeia XV edition.
Results and discussion. The in silico screening of the main target groups of the BAS of the studied raw materials confirmed their high potential astringent and anti-inflammatory activity. The BAS complex of the liquid ex-tract of Michurin's chokeberry leaves in comparison with the tincture shows antimicrobial activity against Pseudomonas aeruginosa up to the 4 th dilution and antifungal activity against Candida albicans up to the 6th dilution. In relation to such pathogenic microorganisms as Bacillus cereus and Staphylococcus aureus both tested dosage forms showed antimicrobial activity up to the 6 th –7 th dilution. The dosage form with a wider spectrum of antimicrobial activity is the liquid extract. In addition, the obtained dosage forms were standardized according to the requirements of the State Pharmacopoeia of the Russian Federation.
Conclusion. The results of the evaluation of the antimicrobial activity of the obtained alcoholic dosage forms based on Michurin's chokeberry leaves (tincture and liquid extract), confirmed the prospects of creating herbal medicines, e.g. for external use in the complex therapy and prevention of diseases of the oral cavity in the form of rinses or applications.
A comparative metabolomic study of three varieties of wild Rosa (Rosa acicularis, Rosa amblyotis, and Rosa rugosa) from a Kamchatka expedition (2024) was conducted via extraction with supercritical carbon dioxide modified with ethanol (EtOH), and detection of bioactive compounds was realized via tandem mass spectrometry. Several experimental conditions were investigated in the pressure range 50–350 bar, with the used volume of co-solvent ethanol in the amount of 2% in the liquid phase at a temperature in the range of 31–70 °C. The most effective extraction conditions are the following: pressure 200 Bar and temperature 55 °C for Rosa acicularis; pressure 250 Bar and temperature 60 °C for Rosa amblyotis; pressure 200 Bar and temperature 60 °C for Rosa rugosa. Three varieties of wild Rosa contain various phenolic compounds and compounds of other chemical groups with valuable biological activity. Tandem mass spectrometry (HPLC-ESI–ion trap) was applied to detect the target analytes. A total of 283 bioactive compounds (two hundred seventeen compounds from the polyphenol group and sixty-six compounds from other chemical groups) were tentatively identified in extracts from berries of wild Rosa. For the first time, forty-eight chemical constituents from the polyphenol group (15 flavones, 14 flavonols, 4 flavan-3-ols, 3 flavanones, 1 phenylpropanoid, 2 gallotannins, 1 ellagitannin, 4 phenolic acids, 1 dihydrochalcone, and 3 coumarins) were identified in supercritical extracts of R. acicularis, R. amblyotis, and R. rugosa.
Anthocyanins have gained significant attention for their potent colorant capacity and multifaceted biological activities. As a result, the quantification of anthocyanin content in wild berries and the identification of anthocyanin profiles have become increasingly important, as well as the optimization of methods for these determinations. The present study shows a rapid UHPLC-DAD method for identifying and quantifying individual anthocyanins in selected wild berries and fruit samples of Mediterranean origin, namely, Prunus avium, Fragaria vesca, and Vaccinium myrtillus. Moreover, the applicability of the developed method to different food matrices was verified in cultivated berries, specifically, Punica granatum, Fragaria x ananassa, Rubus spp., and Vaccinium corymbosum. The developed method showed great sensitivity (LOD of 23.92 ng/g, LOQ of 79.73 ng/g), precision (RSD below 2.599%), and accuracy (recovery percentages of 97.97 and 98.88%). It successfully quantified individual anthocyanins (delphinidin-3-O-glucoside, cyanidin-3-O-glucoside, cyanidin-3-O-rutinoside, petunidin-3-O-glucoside, pelargodinin-3-O-glucoside, malvidin-3-O-glucoside) across different berries and fruit samples. The developed methodology allows to conduct routine analysis without the need for mass spectrometry. The range of total anthocyanins quantified in wild berries and fruit samples was 0.03 to 7.66 mg/g of powdered extract corresponding to Prunus avium L. and Vaccinium corymbosum L., respectively.
Cannabis plants produce a spectrum of secondary metabolites, encompassing cannabinoids and more than 300 non‐cannabinoid compounds. Among these, anthocyanins have important functions in plants and also have well documented health benefits. Anthocyanins are largely responsible for the red/purple color phenotypes in plants. Although some well‐known Cannabis varieties display a wide range of red/purple pigmentation, the genetic underpinnings of anthocyanin biosynthesis have not been well characterized in Cannabis. This study unveils the genetic diversity of anthocyanin biosynthesis genes found in Cannabis, and we characterize the diversity of anthocyanins and related phenolics found in four differently pigmented Cannabis varieties. Our investigation revealed that the genes 4CL, CHS, F3H, F3′H, FLS, DFR, ANS, and OMT exhibited the strongest correlation with anthocyanin accumulation in Cannabis leaves. The results of this study enhance our understanding of the anthocyanin biosynthetic pathway and shed light on the molecular mechanisms governing Cannabis leaf pigmentation.
This study presents the metabolomic profiles of the four Ribes species (Ribes pauciflorum Turcz., Ribes triste Pall., Ribes dicuscha Fisch., and Ribes aureum Purch.). The plant material was collected during two expeditions in the Russian Far East. Tandem mass spectrometry was used to detect target analytes. A total of 205 bioactive compounds (155 compounds from polyphenol group and 50 compounds from other chemical groups) were tentatively identified from the berries and extracts of the four Ribes species. For the first time, 29 chemical constituents from the polyphenol group were tentatively identified in the genus Ribes. The newly identified polyphenols include flavones, flavonols, flavan-3-ols, lignans, coumarins, stilbenes, and others. The other newly detected compounds in Ribes species are the naphthoquinone group (1,8-dihydroxy-anthraquinone, 1,3,6,8-tetrahydroxy-9(10H)-anthracenone, 8,8′-dihydroxy-2,2′-binaphthalene-1,1′,4,4′-tetrone, etc.), polyhydroxycarboxylic acids, omega-3 fatty acids (stearidonic acid, linolenic acid), and others. Our results imply that Ribes species are rich in polyphenols, especially flavanols, anthocyanins, flavones, and flavan-3-ols. These results indicate the utility of Ribes species for the health and pharmaceutical industry.
BACKGROUND
Polyphenolic-rich chokeberry extracts and juice could provide health benefits in humans. Moreover, by-products after processing stand out as a potential new source of valuable compounds.
OBJECTIVE
The research aimed to evaluate in vitro bioactivity of chokeberry fruit extract, juice, and waste extract (material remaining after juice processing) based on their chemical composition and molecular docking analysis.
METHODS
Spectrophotometric methods were used to determine the phenolics, anthocyanins, flavonoids, and proanthocyanins content in freeze-dried samples. Additionally, individual anthocyanins, flavonoids, and sugars were identified through HPLC analysis. The antioxidant capacity was tested using two in vitro methods and assessing antimicrobial activity. The effects of tyrosinase and acetylcholinesterase inhibition were examined using spectrophotometric methods. Molecular docking analysis identified the interaction of chokeberry components with the active sites of these enzymes.
RESULTS
The waste extract exhibited the most robust antioxidant activity within the DPPH system. While bactericidal activity was absent across all chokeberry preparations, they demonstrated inhibitory effects on specific microbiological strains relevant to the gastrointestinal tract. Results revealed the chokeberry products’ ability to inhibit tyrosinase and acetylcholinesterase. Molecular docking confirmed the strong interactions between chokeberry compounds and these enzymes.
CONCLUSION
The results indicate the potential of chokeberry products and by-products as valuable resources for pharmaceutical applications.
The fruits of Prunus domestica L. are a valuable source of phenolic compounds, in particular hydroxycinnamic acids and their esters. Hybrid origin of Prunus domestica hexaploid species, a huge variety of varieties and di erent growing areas do not allow scientists to make a de nitive conclusion about certain phenolic compounds in plum fruits. The purpose of our research is to determine and identify the phenolic composition of fruits of Prunus domestica L. growing in the Tambov region of the Russian Federation. Eight varieties of universal and table plum were taken as objects of research. Experimental plantations were planted in 2014 according to the scheme of 6x3 m. SVG 11-19 was used as a rootstock. The study of phenolic components of plum fruits was performed by HPLC using a Thermo Ultimate 3000 liquid chromatograph equipped with a DAD-3000. Separation was performed on a Hypersil Gold C18 column (4.6 × 250 mm, 5 μm). The binary mobile phase gradient was phosphate and acetonitrile. For the analysis, plum fruits were extracted with 70 % aqueous methanol. The levels of hydroxycinnamic acids in the plum fruits studied were determined: 4-ca eoylquinic acid-5.33…181.54 mg/100 g, 5- ca eoylquinic acid - 1.69…31.73 mg/100 g, 3-p-coumaroylquinic acid - 0.54…5.77 mg/100 g, 3- ca eoylquinic acid-0.04…0.63 mg/100 g. Among avonols, the predominant component is quercitin-3-rutinoside - 0.77…9.17 mg/100 g. Three anthocyanins were identi ed in the studied plum fruits: cyanidin-3-glucoside, cyanidin-3-rutinoside and peonidin-3-glucoside. In the structural composition of plum fruit anthocyanins, cyanidin-3-glucoside dominates, accounting for 60 to 90 % of the total anthocyanin content. The obtained data on the content of phenolic components in fruits of isolated plum varieties (Prunus domestica L.) indicate the promise of their further study for breeding studies and as a source of hydroxycinnamic acids, anthocyanins and avonols in the diet of the population
Beverages with nutritional functional properties constitute one of the fastest‐growing segments in the food industry. Beverages produced with berries as raw materials, owing to their richness in various beneficial substances (such as fiber, vitamins, minerals, and bioactive phytochemicals), have emerged as integral components of nutritional functional beverages. In this review, we summarize the bioactive polyphenols present in berry beverages and discuss the potential properties of berries from an antidiabetic perspective. The application and impact of new technologies in the processing and production of berry beverages are also explored. Additionally, the review addresses the challenges and prospects faced by industrial development in berry beverage production. Our objective is to provide valuable information for food researchers and the berry beverage production industry, facilitating the production of highly nutritious drinks that appeal to consumers.
Flavonoids are a class of polyphenolic compounds that can be classified into six distinct categories, namely isoflavonoids, flavanones, flavanols, flavonols, flavones, and anthocyanidins. These compounds are naturally occurring and can be found in a diverse range of plant species. Flavonoids, a class of bioactive compounds, are mostly obtained through the consumption of vegetables, fruits and plant-derived beverages such as wine, cocoa-based products and green tea. Flavonoids have been demonstrated to exhibit a diverse range of anticancer properties. These include the modulation of activities of enzymes involved in scavenging reactive oxygen species, involvement in cell cycle arrest, induction of apoptosis and autophagy, as well as suppression of cancer cell proliferation and invasiveness. Flavonoids exhibit a dual role in maintaining reactive oxygen species balance. They function as antioxidants in regular physiological conditions, while also demonstrating significant pro-oxidant properties in cancer cells. This prooxidant activity induces apoptotic pathways and downregulates pro-inflammatory signalling pathways. The paper explores the biochemical characteristics, bioavailability, anticancer efficacy, and modes of action of flavonoids.
This study examined the phenolic profile, sugar composition, and antioxidant capacities of chokeberry fruits and leaves obtained from four different Turkiye provinces. A total of 21 phenolics including phenolic acid and its derivatives, flavanols, anthocyanins, and flavonols were determined in the fruits, while the leaves had 19 phenolics, including phenolic acid and its derivatives, flavanols, and flavonols. The total amount of phenolic compounds was the highest in both fruits and leaves in the samples from the Bursa province. Cis 5-O-p-coumaroylquinic acid and secoxyloganin were quantified for the first time in both fruits and leaves. In summary, it was found that different geographical locations significantly affected the phenolics, sugar contents, and antioxidant activities of the fruits and leaves.
The main objective of this study was to evaluate the effects of supplementation the diet of pigs with grape pomace preserved in silage form (GPS) and its interaction with indoor and outdoor production systems, with and without access to vegetation, on the attributes of meat quality produced. Analyzes of proximal composition, cholesterol content, fatty acid profile, shear force, texture profile and sensory analysis were performed. During cold storage, oxidative stability and objective color were analyzed. Statistical analysis was performed in a 3x2 factorial design (production systems (S) x GPS-feed (F)) and the interaction between them (S*F). The results showed that there was no interaction between the production system and GPS feeding for the attributes evaluated. The proximate composition and fatty acid profile of the muscle remained unchanged. Additionally, it provides higher subjective and objective tenderness, higher red color intensity, and reduces lipid oxidation under refrigeration. The supplementation of pig feed with GPS improve the quality of the meat and constitute a sustainable alternative for the winemaking residue.
Apple fruit skin color fading is not well understood although the molecular mechanism of skin color formation is well known. The red-fleshed apple cultivar ‘Daihong’ (‘DH’) exhibited fading skin color during fruit development despite having a heterozygous R6 allele but lacking Red-TE for red fruit skin. In this study, transcriptomic analysis revealed the expression level of MdMYB10 increased with fruit development whereas reduced expression levels of MdMYBPA1, MdCHS, MdANS, MdUFGT, MdLAR, and MdANR were observed, consistent with decreased levels of chalcone, anthocyanin, catechin, epicatechin, and procyanidin B2. Whole-genome bisulfite sequencing (WGBS) indicated a global gain in cytosine methylation levels and increased methylation in 5’ and 3’ flanking regions of genes and transposable elements (TEs), and in TE body in all CG, CHG and CHH context, especially mCHH context, during fruit development. The increased DNA methylation was attributed to reduced expression levels of DNA demethylase genes, including MdDME1, MdROS1 and MdROS2. Association analysis revealed a significant negative correlation between promoter methylation levels of MdCHS, MdCHI, MdMYBPA1, and their respective transcript levels, as well as a negative correlation between promoter methylation levels of MdCHS, MdCHI, MdANR, MdFLS, and the content of chalcones, naringenin-7-glucoside, epicatechin, and quercetin, respectively. The treatment of DNA demethylation agent 5-aza-2’-deoxycitydine verified the negative correlation between DNA methylation and gene expression within flavonoid pathway. These findings suggest that hypermethylation in promoter regions of genes of the flavonoid biosynthesis pathway is associated with the reduction of gene expression and flavonoid content, and fruit skin color fading during ‘DH’ apple development.
Bu calışmada aronya posasının taze ve silolanarak saklanmasının yem değeri üzerine olan etkileri araştırılmıştır. Aronya posası Tekirdağ Bağcılık Araştırma enstitüsünden temin edilmiştir. Taze olarak alınan yaklaşık 50 kg posa laboratuvar ortamına getirilmiş ve 2 muamele (silolanmamış ve silolanmış) grubuna ayrılmıştır. Taze aronya posası açıkta bırakılarak 7 günlük aerobik stabilite testine tabi tutulmuştur. Diğer muamele grubunda aronya posası 30 gün silolanmış ve silolama sonrası 7 günlük aerobik stabilite testine tabi tutulmuştur. Taze ve silolanmış yem örneklerinde aerobik stabilitenin 0., 1., 3., 7. günlerinde kimyasal ve mikrobiyolojik analizler yapılmıştır. Ayrıca in vitro gaz üretim tekniğinin kullanıldığı çalışmada, grupların gaz üretimi (GÜ), metan üretimi (CH4), karbon dioksit üretimi (CO2), amonyak üretimi (NH3) ve hidrojen sülfür üretimi (H2S) belirlenmiştir. İnkübasyonun 24. saatinde elde edilen GÜ miktarları ile organik madde sindirilebilirligi (OMS), metabolik enerji (ME) ve net enerji laktasyon (NEL) degerleri hesaplanmıştır. Rumen sıvısına ilişkin parametreler olarak, protozoa sayısı, pH değerleri ve viskozitesi belirlenmiştir. Aronya posalarında aerobik stabilite süresi arttıkça kuru madde (KM) miktarı artmıştır. Diğer yandan, aronya posasının silolanması ve aerobik stabilite süresi maya değerleri üzerine istatistiksel olarak etki göstermemiştir. Aronya posalarının aerobik stabilite süresi arttıkça pH değeri yükselmiştir. İnkübasyonun 48. saatine kadar en yüksek GÜ miktarı başlangıç materyalinde bulunmuştur. En düşük CH4, CO2, NH3 ve H2S miktarları silolanmış grupta, aerobik stabilitenin 7. gününde belirlenmiştir. Elde edilen analiz sonuçlarına göre, aronya posasının ruminant hayvanların beslenmesi için önemli bir kaba yem kaynağı olduğu belirlenmiştir. Kuru madde miktarının yüksek olması, aronya posasının 7 gün boyunca bozulmadan kalabildiğini göstermiştir. Kuru madde miktarı düşük yemlerin saklanma şekillerinden biri olan silolama, aronya posası için besin madde kayıplarına neden olmuştur.
This study evaluates whether elderberry (EB) effectively decreases the inflammation and oxidative stress in the brain cells to reduce Aβ toxicity. In the Aβ + EB group, EB powder was added to rats’ routine diet for eight consecutive weeks. Then, spatial memory, working memory, and long-term memory, were measured using the Morris water maze, T-maze, and passive avoidance test. Also, in this investigation immunohistopathology, distribution of hippocampal cells, and gene expression was carried out. Voronoi tessellation method was used to estimate the spatial distribution of the cells in the hippocampus. In addition to improving the memory functions of rats with Aβ toxicity, a reduction in astrogliosis and astrocytes process length and the number of branches and intersections distal to the soma was observed in their hippocampus compared to the control group. Further analysis indicated that the EB diet decreased the caspase-3 expression in the hippocampus of rats with Aβ toxicity. Also, EB protected hippocampal pyramidal neurons against Aβ toxicity and improved the spatial distribution of the hippocampal neurons. Moreover, EB decreased the expression of inflammatory and apoptotic genes. Overall, our study suggest that EB can be considered a potent modifier of astrocytes’ reactivation and inflammatory responses.
A group of arylalkyl isothiocyanates were tested for their abilities to inhibit tumorigenicity and DNA methylation induced by the esophageal-specific carcinogen, N-nitrosomethylbenzylamine (NMBA) in the F344 rat esophagus. Phenylpropyl isothiocyanate (PPITC) was more potent than either phenylethyl isothiocyanate (PEITC) or benzyl isothiocyanate (BITC). Phenylbutyl isothiocya-nate (PBITC), however, had a lesser inhibitory effect on esopha-geal tumorigenesis, and phenylhexyl isothiocyanate (PHITC) actually enhanced esophageal tumorigenesis. Thus, the two-and three-carbon isothiocyanates were more effective inhibitors of NMBA-esophageal carcinogenesis than the longer chain isothio-cyanates. The effects of the isothiocyanates on tumorigenesis were well correlated as to their effects on DNA adduct formation. The most likely mechanism of inhibition of tumorigenesis by these isothiocyanates is via inhibition of the cytochrome P450 enzymes responsible for the metabolic activation of NMBA in rat esophagus. A freeze-dried strawberry preparation was also evaluated for its ability to inhibit NMBA-esophageal tumorigenesis. It proved to be an effective inhibitor, although not as potent as either PEITC or PPITC. The inhibitory effect of the berries could not be attributed solely to the content of the chemopreventive agent, ellagic acid, in the berries.
Admission rates for asthma in 1991-2 were 80-100% above national averages for all age groups in east London.1 We have shown in east London general practices that a higher ratio of prophylaxis to bronchodilator prescribing occurs in training practices and those approved for health promotion band 3 and asthma surveillance.2 We have also explored the relation of appropriate prescribing for asthma to other local practice characteristics.3 We investigated excessive asthma admission rates in patients from these practices by studying the relation between asthma prescribing and admissions.
Methods and results
Data on asthma admissions by age for east London residents in 134 out of 163 practices covered two years from April 1992 and included some 1602 patients (800 in 1992-3 and 802 in 1993-4). Ninety eight per cent of admissions for asthma were acute and only 3% of all patients admitted were not allocated to a practice. Data were obtained from the integrated district and regional information system with the international classification of disease code 493. Rates per thousand patients per practice were calculated from the average number of patients admitted per year; this excluded readmissions within the same year. The denominators were the resident population of east London in each practice at June 1993 and June 1994. We also investigated admission rates in the age groups under 5, 5-64, and 65 and over.
Our asthma prescribing data have been described elsewhere.2 While only one year's prescribing data were available (April 1992 to March 1993), our experience from a parallel study in 24 local practices is that the prescribing ratios remained almost constant during our two year study period.
Table 1 presents the mean (SD) asthma admission rates for different categories of the prophylaxis to bronchodilator ratios. These ratios have been divided into four groups by the 25th and 75th percentiles and the median. Statistical significance was determined by Cuszick's test for trend. Table 1 shows that practices prescribing higher ratios of prophylaxis to bronchodilator medication had on average lower admission rates for asthma. Significant trends were observed in those aged 5-64. For young children and the elderly, however, we found neither significant trends nor differences in admission rates between categories of the prescribing ratios (prescribing items ratios: for under 5s P=0.61; for the elderly P=0.17; prescribing cost ratios: for under 5s P=0.38; for the elderly P=0.62).
View this table:View PopupView InlineTable 1 Asthma admission rates (per 1000 patients per practice) by age group and the ratio of prophylaxis to bronchodilator prescribing in east London practices
Comment
We have shown an association between asthma prescribing and morbidity experienced by patients with asthma, as reflected in admissions to hospital. Practices with higher prescribing ratios had lower admission rates to hospital. This relation has been reported by other workers.4 The diagnostic coding for asthma is probably most secure in the middle age band: the lack of association in those aged under 5 and in the elderly may reflect the presence of other conditions such as chronic cough and chronic obstructive pulmonary disease, possibly classified under the asthma code.
Prescribing studies are often crude and may be complicated by problems such as indication and compliance5; ours is no exception. Nevertheless, that we can relate this marker to a patient outcome such as admission rate is encouraging. While this relation is not necessarily causal (higher prescribing ratios may simply be a marker for other aspects of good asthma care), it seems sensible to promote more appropriate prescribing for asthma, particularly in practices with low prophylaxis to bronchodilator ratios. Methods might include facilitating local asthma guidelines, practice based medical education, and financial incentives. Further studies should address other patient and practice factors that may be associated with asthma admission rates and investigate the relation between prescribing patterns and a wider range of patient outcomes.
We thank Jacqui Bobby for providing us with asthma admissions data and the Prescription Pricing Authority for its information, which was obtained by JN when she was medical adviser to the family health services authority. We also thank Kath Moser and Mike Chambers for their support with the general practice database.
Footnotes
Funding Wellcome Trust.
Conflict of interest None.References1.↵City and East London.Health in the east end. Annual public health report statistical supplement 1994-5.London:City and East London Health Authority,1994.2.↵Naish J, Sturdy P, Toon P.Appropriate prescribing in asthma and its related cost in east London.BMJ1995; 310:97–100.OpenUrlFREE Full Text3.↵Sturdy P, Naish J, Pereira F, Griffiths C, Dolan S, Toon P, Chambers M.General practice characteristics associated with appropriate prescribing for asthma in east London.BMJ1995; 311:1547–8.OpenUrlFREE Full Text4.↵Shine C, Dutt A.Good prescribing is encouraged.BMJ1995; 310:1070.OpenUrlFREE Full Text5.↵Campbell M, Bateman DN, Roberts SJ, Smith JM.PACT data have drawbacks.BMJ1995; 310:1069.OpenUrlFREE Full Text
Anthocyanins from fruits of Aronia melunocap (chokeberry) were extracted with acidified ethanol and methanol and fractionated by high performance liquid chromatography. The pigment composition was very simple as there were only four compounds. Semi-preparative HPLC, thin-layer chromatography and spectral techniques indicated cyanidin as a single aglycone and glucose, galactose, arabinose, and xylose as associated sugars. The relative proportions of anthocyanins were determined. The major components were cyanidin 3-galactoside and cyanidin 3-arabinoside.
A group of arylalkyl isothiocyanates were tested for their abilities to inhibit tumorigenicity and DNA methylation induced by the esophageal-specific carcinogen, N-nitrosomethylbenzylamine (NMBA) in the F344 rat esophagus. Phenylpropyl isothiocyanate (PPITC) was more potent than either phenylethyl isothiocyanate (PEITC) or benzyl isothiocyanate (BITC). Phenylbutyl isothiocyanate (PBITC), however, had a lesser inhibitory effect on esophageal tumorigenesis, and phenylhexyl isothiocyanate (PHITC) actually enhanced esophageal tumorigenesis. Thus, the two- and three-carbon isothiocyanates were more effective inhibitors of NMBA-esophageal carcinogenesis than the longer chain isothiocyanates. The effects of the isothiocyanates on tumorigenesis were well correlated as to their effects on DNA adduct formation. The most likely mechanism of inhibition of tumorigenesis by these isothiocyanates is via inhibition of the cytochrome P450 enzymes responsible for the metabolic activation of NMBA in rat esophagus. A freeze-dried strawberry preparation was also evaluated for its ability to inhibit NMBA-esophageal tumorigenesis. It proved to be an effective inhibitor, although not as potent as either PEITC or PPITC. The inhibitory effect of the berries could not be attributed solely to the content of the chemopreventive agent, ellagic acid, in the berries.
Oral cavity cancers represent 2.5% of the cancers that occur in the United States and are ranked sixth worldwide. Since current therapeutic protocols are relatively ineffective, alternative strategies for prevention need to be developed and tested in appropriate animal models. In the study reported herein, the hamster cheek pouch (HCP) was used to evaluate the ability of black raspberries to inhibit oral cavity tumors. Male Syrian Golden hamsters, 3-4 weeks of age, were fed 5% and 10% lyophilized black raspberries (LBR) in the diet for two weeks prior to treatment with 0.2% 7,12-dimethylbenz(a) anthracene in dimethylsulfoxide and for 10 weeks thereafter. HCPs were painted 3X/week for eight weeks. The animals were sacrificed 12-13 weeks from the beginning of DMBA treatment and the number and volume of tumors (mm3) determined. There was a significant difference (p = 0.02) in the number of tumors between the 5% LBR and control groups (27 tumors/14 animals and 48 tumors/15 animals, respectively) and an intermediate number of tumors in the 10% berry-treated animals (39 tumors/15 animals). These experiments support previous studies from our laboratories showing the chemopreventive activity of black raspberries and show, for the first time, that dietary black raspberries will inhibit tumor formation in the oral cavity.
A normal-phase HPLC-MS/MS method was applied to screen for proanthocyanidins in 88 different kinds of foods. Thirty-nine foods were found to contain proanthocyanidins. These foods include 19 kinds of fruits, eight cereals/beans, seven nuts, two beverages, two spices, and one vegetable. Twenty-five kinds of foods were found to contain both oligomeric (DP </= 10) and polymeric proanthocyanidins (DP > 10), and the other 14 foods contained only oligomers. Procyanidins with B-type linkages were detected as the only components in 21 foods and also as principal components in the others. Propelargonidins were identified in pinto bean, raspberry, strawberry, and almond, etc. Plum, avocado, peanut, curry, and cinnamon were identified as potential sources of A-type proanthocyanidins in addition to cranberry. Thiolytic degradation and MS/MS analyses indicated that the A-type linkages are present as a terminal unit in plum or between the extension units in curry, cinnamon, and avocado, whereas A-type linkages exist at both positions in cranberry and peanut.
Proanthocyanidins (PAs) have been shown to have potential health benefits. However, no data exist concerning their dietary intake. Therefore, PAs in common and infant foods from the U.S. were analyzed. On the bases of our data and those from the USDA's Continuing Survey of Food Intakes by Individuals (CSFII) of 1994-1996, the mean daily intake of PAs in the U.S. population (>2 y old) was estimated to be 57.7 mg/person. Monomers, dimers, trimers, and those above trimers contribute 7.1, 11.2, 7.8, and 73.9% of total PAs, respectively. The major sources of PAs in the American diet are apples (32.0%), followed by chocolate (17.9%) and grapes (17.8%). The 2- to 5-y-old age group (68.2 mg/person) and men >60 y old (70.8 mg/person) consume more PAs daily than other groups because they consume more fruit. The daily intake of PAs for 4- to 6-mo-old and 6- to 10-mo-old infants was estimated to be 1.3 mg and 26.9 mg, respectively, based on the recommendations of the American Academy of Pediatrics. This study supports the concept that PAs account for a major fraction of the total flavonoids ingested in Western diets.
The antioxidant activity of phenolics in fruits of blueberry (Vaccinium corymbosum cv. Sierra), cranberry (Vaccinium macrocarpon cv. Ben Lear), wild chokeberry (Aronia melanocarpa), and lingonberry (Vaccinium vitis-idaea cv. Amberland) was determined in this study. The phenolic constituents and contents among the different berries varied considerably. Anthocyanins were found to be the main components in all these berries. Chlorogenic acid in blueberry, quercetin glycosides in cranberry and lingonberry, and caffeic acid and its derivative in chokeberry were also present in relatively high concentrations. Chlorogenic acid, peonidin 3-galactoside, cyanidin 3-galactoside, and cyanidin 3-galactoside were the most important antioxidants in blueberry, cranberry, wild chokeberry, and lingonberry, respectively. The contribution of individual phenolics to the total antioxidant capacity was generally dependent on their structure and content in the berries. Phenolics such as quercetin and cyanidin, with 3',4'-dihydroxy substituents in the B ring and conjugation between the A and B rings, had highly effective radical scavenging structures in blueberries, cranberries, chokeberries, and lingonberries. Phenolic acids such as caffeic acid also showed high antioxidant activity, probably due to its dihydroxylation in the 3,4 positions as hydrogen donors.
This text is a comprehensive reference covering the chemistry, physiology, chemotaxonomy, biotechnology and food technology aspects of the anthocyanins. Topics discussed include types of anthocyanins, structural transformations, colour stabilization and intensification factors, biosynthesis and intensification factors, biosynthesis, analysis and functions of anthocyanins. An in-depth review of the literature discussing anthocyanins of fruits, cereals, legumes, roots, tubers, bulbs, cole crops, oilseeds, herbs, spices, and minor crops is included as well.
Pyranoanthocyanidins generated from the respective glycosides on hydrolysis were found to undergo rearrangement to form a new type of furoanthocyanidins with a core structure of furo[2,3-c]-1-benzopyrylium.
Anthocyanins of the main red fruits (bilberry, blackcurrant, strawberry, blackberry, black cherry, morello, raspberyy and elderberry) were analysed by high-performance liquid chromatography (HPLC). Some identifications could only be achieved after semi-preparative HPLC, partial hydrolysis and analysis of the framents obtained. The various parameters affecting the retention were studied and, in particular, the respective influences of the constituent aglycone and sugars could be distinguished and quantified. The effect of the mobile phase composition was also studied and allowed the peak inversions observed to be explained and some of the coelutions to be solved.
To determine whether flavonoid intake explains differences in mortality rates from chronic diseases between populations.
Cross-cultural correlation study.
Sixteen cohorts of the Seven Countries Study in whom flavonoid intake at baseline around 1960 was estimated by flavonoid analysis of equivalent food composites that represented the average diet in the cohorts.
Mortality from coronary heart disease, cancer (various sites), and all causes in the 16 cohorts after 25 years of follow-up.
Average intake of antioxidant flavonoids was inversely associated with mortality from coronary heart disease and explained about 25% of the variance in coronary heart disease rates in the 16 cohorts. In multivariate analysis, intake of saturated fat (73%; P = 0.0001), flavonoid intake (8%, P = .01), and percentage of smokers per cohort (9%; P = .03) explained together, independent of intake of alcohol and antioxidant vitamins, 90% of the variance in coronary heart disease rates. Flavonoid intake was not independently associated with mortality from other causes.
Average flavonoid intake may partly contribute to differences in coronary heart disease mortality across populations, but it does not seem to be an important determinant of cancer mortality.
Elderberry anthocyanins (Sambucus nigra) including acylated derivatives (Sambucus canadensis) were studied for use as beverage pigments. Cyanidin 3-O-(6-O-E-p-coumaroyl-2-O-β-d-xylopyranosyl)-β-d-glucopyranoside-5-O-β-d-glucopyranoside from S. canadensis was more stable than cyanidin 3-sambubioside from S. nigra. Acylation improved both heat and light stability, whereas glycosidation only stabilized anthocyanins in the presence of light. Cyanidin 3-(E)-p-coumaroyl-sambubioside-5-glucoside changed to three new anthocyanins under light irradiation. These three anthocyanins were isolated, and their structures were identified to be cyanidin 3-O-(6-O-Z-p-coumaroyl-2-O-β-d-xylopyranosyl)-β-d-glucopyranoside-5-O-β-d-glucopyranoside, cyanidin 3-O-(6-O-E-p-coumaroyl-2-O-β-d-xylopyranosyl)-β-d-glucopyranoside, and cyanidin 3-O-(6-O-Z-p-coumaroyl-2-O-β-d-xylopyranosyl)-β-d-glucopyranoside. Keywords: Sambucus nigra; S. canadensis; Caprifoliaceae; elderberry; color stability; acylated anthocyanin
A rapid method for complete chemical characterization of anthocyanins has been developed. The method uses a single acid hydrolysis of anthocyanins in methanol-2 N HCl to effectively cleave the intact pigments into stable aglycons, sugars, and acyl groups. The anthocyanidins and phenolic acids are characterized by reversed-phase high-performance liquid chromatography (RP-HPLC) in a single analytical run using retention times and UV-vis absorption spectra. The aliphatic acylating acids and the sugars are characterized by capillary gas-liquid chromatography (GLC) analysis of trimethylsilyl derivatives of sugars and aliphatic acids and methyl esters of aliphatic acids. This procedure, which is fast and reliable, requires minimal sample size and should be useful in the characterization of anthocyanins.
Spectral, acid-base, and redox properties of the phenoxyl radicals derived from 3,4-dihydroxybenzene derivatives and selected flavonoids were studied by pulse radiolysis of aqueous solutions. From the pH-dependent changes in the phenoxyl spectra, the dissociation constants were derived. The pK(a), values for the deprotonation of the 3'-OH group in the catechin (pK(a) = 4.6) and rutin (pK(a) = 4.3) radicals are similar to the pK(a) value of the 3,4-dihydroxybenzoate radicals, pK(a) = 4.2, which is expected from their similar electronic structures. Deprotonation of 5- and 7-OH in the catechin and rutin and of 5-OH in the hesperidin radicals has no effect on the radical spectra, which is explained by the inefficient coupling of the A-ring of the flavonoid radicals with the unpaired electron. Because of favorable reduction potentials of the phenoxyl radicals, E(7) = 0.56-0.7 V vs NHE, flavonoids may act as efficient antioxidants of alkylperoxyl and superoxide/hydroperoxyl radicals. The ac kinetic conductivity method was developed for the measurements of the low reaction rate constants of the superoxide radical reactions with flavonoids and phenols in aqueous solutions at pH 10. The rates of the superoxide radical reactions with flavonoids, k = 3 X 10(2)-5.1 X 10(4) M(-1) s(-1), depend on the redox properties and the charge of the flavonoids. The highest rates are measured for the oxidation of quercetin and rutin, whereas the lowest are those for the B-ring monosubstituted derivatives, with substantially higher redox potentials. Uncharged catechin at pH 7 reacts at k = 6.6 X 10(4) M(-1) s(-1), whereas the rate at pH 10, where catechin is doubly negatively charged, is approximately 4 times lower, k = 1.8 x 10(4) M(-1) s(-1). The activation parameters of the oxidation of rutin and trolox at pH 10 and methyl gallate at pH 7 were determined in an attempt to understand why the rates of the superoxide reactions are low despite high driving forces of Delta E greater than or equal to 0.4 V. Low activation enthalpies, Delta H-double dagger = 2.3-3.6 kcal/mol, and negative activation entropies, Delta S-double dagger = -25-28 cal/(mol K), point to an inner-sphere electron-transfer mechanism.
Proanthocyanidins (syn condensed tannins) are complex flavonoid polymers naturally present in cereals, legume seeds and particularly abundant in some fruits and fruit juices. They share some common structural features—phenolic nature and high molecular weight—with phenolic polymers found in black tea and red wine (called here tannin-like compounds). The polymeric nature of proanthocyanidins makes their analysis and estimation in food difficult. For this reason, little is known about their consumption, although they likely contribute a large part of the daily polyphenol intake. They also share common physicochemical properties: they form stable complexes with metal ions and with proteins and are, like other polyphenols, good reducing agents. Many of their biological effects of nutritional interest derive from these properties. As metal ion chelators, they influence the bioavailability of several minerals. The nutritional significance of the non-specific complexation of proteins is less clear. As reducing agents, they may participate in the prevention of cancers, both of the digestive tract and inner organs. They may also protect LDLs against oxidation and inhibit platelet aggregation and therefore prevent cardiovascular diseases. In vitro, animal and human studies on the prevention of these chronic diseases are reviewed with particular attention to wine and tea polyphenols. The lack of data on their bioavailability and the paucity of human studies are emphasised.© 2000 Society of Chemical Industry
This paper reviews the literature on the occurrence of anthocyanins in foods and their transformation during processing, including the formation of adducts and derived tannins. Data describing the safety of anthocyanins and possible dietary effects are examined. Attention is drawn to some misquotations in the literature and to some serious gaps in our knowledge, in particular, the lack of pharmacokinetic data in humans essential to an understanding of associated biological effects.© 2000 Society of Chemical Industry
Anthocyanins undergo unusual facile reactions with acetone to give rise to pyranoanthocyanins, thus showing that the new class of pigments isolated from blackcurrant seeds were a result of solvent participation. This oxidative addition was extended to the successful synthesis of pyranomalvidin or 2-(3,5-dimethoxy-4-hydroxyphenyl)-8-hydroxy-5-methyl-3-O-β-d-glucopyranosyloxypyrano[4,3,2-de]-1-benzopyrylium by the reaction of the principal grape anthocyanin malvidin 3-O-glucoside with acetone. The chemical structures of pyranomalvidin, together with pyranocyanin B and pyranodelphinin B, were fully characterised by 2D NMR.
The present knowledge on the qualitative and quantitative analysis of procyanidins is reviewed. Procyanidins belong to the class of natural products known as proanthocyanidins or condensed polyphenols. The instability of procyanidins should be considered throughout sample collection, storage and clean up procedures. Extractions are preferentially conducted using aqueous acetone. Addition of an antioxidant is recommended as long as it does not interfere with the analytical procedure. Conventional methods are mainly based on color reactions, of which only functional group assays exhibit specificity for proanthocyanidins. The dimethylaminocinnamaldehyde assay is gaining importance compared to the most widely used vanillin assay, because it is more specific, more sensitive and less subject to interferences. Individual procyanidins can only be assessed by chromatography. Reversed phase high performance liquid chromatography on C-18 stationary phases using acidic aqueous methanol or acetonitrile as eluents is the procedure of choice. Oligomeric procyanidins do not elute according to their degree of polymerization. Polymers can not be chromatographed and hamper the most commonly used UV detection at 280 nm. Sample clean up procedures are inevitable because of these polymeric compounds and phenolic acids as well as flavonoids, which tend to co-elute with procyanidins. Liquid 1 quid extraction using ethyl acetate is not quantitative. Solid phase extraction over C-18, polyamide or Sephadex LH-20 are described in the literature, but none of these procedures is completely validated. More selective detection modes like electrochemical detection or mass spectrometry as well as derivatization procedures are discussed as possible alternatives to extensive sample clean up procedures.
The major flavonol glycosides of ripe blackcurrants (Ribes nigrum cv. Silvergieters Schwarze), myricetin 3--d-glucopyranoside, rutin, and isoquercitrin, have been isolated in crystalline form. Analysis by thin-layer chromatography confirmed the occurrence of the 3-rutinosides and 3-glucosides of cyanidin and delphinidin. No free flavonoid aglycones could, however, be detected in the fresh berries. The major constituent fluorescing blue under ultraviolet light on paper and cellulose thin-layer chromatograms, was isolated and characterized as 1O-caffeyl--d-glucopyranose. Also isolated were 1-O-ferulyl-and 1-O-p-coumaryl--d-glucopyranose. The occurrence of hydroxycinnamyl-d-glucoses in black-currants does not appear to have been recognized previously.Aus den reifen Beeren der Schwarzen Johannisbeeren (Ribes nigrum Silvergieters Schwarze) wurden Myricetin-3--d-glucopyranosid, Rutin und Isoquercitrin als Hauptflavonolglykoside kristallin gewonnen. Dnnschichtchromatographisch wurde das Vorkommen der 3-Rutinoside und 3-Glucoside des Cyanidins und Delphinidins besttigt. Freie Flavonoid-Aglykone treten jedoch in frischen Beeren nicht auf. Die hauptschliche auf Papier- und Cellulose Dnnschichtchromatogrammen unter Ultraviolettlicht blau fluorescierende Verbindung wurde als 1-O-Caffeyl--d-glucopyranose charakterisiert. Daneben wurden 1-O-Ferulyl- und 1-O-p-Cumaryl--d-glucopyranose isoliert. Zuckerester der Hydroxyzimtsuren sind bisher offensichtlich in Schwarzen Johannisbeeren noch nicht aufgefunden worden.
For the first time, a database of the antioxidant capacities of both the lipophilic and hydrophilic components of foods has been developed using the modified oxygen radical absorbance capacity (ORACFL) assay and a peroxyl radical generator. For lipophilic components, randomly methylated β-cyclodextrin was used as a solubility enhancer. Four representative samples were extracted directly with the hydrophilic solvent (acetone:water:acetic acid, 70:29.5:0.5). Their ORACFL values were similar to that obtained for hydrophilic ORACFL (H-ORACFL) following lipophilic extraction with hexane:dichloromethane (1:1). Lipophilic ORAC values (L-ORACFL) were relatively low compared to H-ORACFL, ranging from 0.11±0.06 to 154.70±3.58 μmol TE/g of fresh or dry weight, whereas H-ORACFL ranged from 1.23±0.17 to 175.24±10.36 μmol TE/g of fresh or dry weight. Total antioxidant capacity (TAC) was calculated as the sum of the lipophlic and hydrophilic ORACFL values. L-ORACFL as a percentage of TAC ranged from 0.27% to 63.70%. Sampling time during the year significantly influenced lipophilic and/or hydrophilic ORACFL values in some food samples. In order to get an accurate total antioxidant capacity of a given food sample, both lipophilic and hydrophilic fractions need to be measured. Food processing, such as cooking or peeling, need to be considered as additional factors which can introduce variation in antioxidant capacity measurements of foods.
Incluye bibliografía e índice
Different cultivars of four Vaccinium species [Vaccinium corymbosum L (Highbush), Vaccinium ashei Reade (Rabbiteye), Vaccinium angustifolium (Lowbush), and Vaccinium myrtillus L (Bilberry)] were analyzed for total phenolics, total anthocyanins, and antioxidant capacity (oxygen radical absorbance capacity, ORAC). The total antioxidant capacity of different berries studied ranged from a low of 13.9 to 45.9 micromole Trolox equivalents (TE)/g of fresh berry (63.2-282.3 micromole TE/g of dry matter) in different species and cultivars of Vaccinium. Brightwell and Tifblue cultivars of rabbiteye blueberries were harvested at 2 times, 49 days apart. Increased maturity at harvest increased the ORAC, the anthocyanin, and the total phenolic content. The growing location (Oregon vs Michigan vs New Jersey) did not affect ORAC, anthocyanin or total phenolic content of the cv. Jersey of highbush blueberries. A linear relationship existed between ORAC and anthocyanin (r(xy) = 0.77) or total phenolic (r(xy) = 0.92) content. In general, blueberries are one of the richest sources of antioxidant phytonutrients of the fresh fruits and vegetables we have studied.
The total antioxidant activity of 12 fruits and 5 commercial fruit juices was measured in this study using automated oxygen radical absorbance capacity (ORAC) assay. On the basis of the wet weight of the fruits (edible portion), strawberry had the highest ORAC activity (micromoles of Trolox equivalents per gram) followed by plum, orange, red grape, kiwi fruit, pink grapefruit, white grape, banana, apple, tomato, pear, and honeydew melon. On the basis of the dry weight of the fruits, strawberry again had the highest ORAC activity followed by plum, orange, pink grapefruit, tomato, kiwi fruit, red grape, white grape, apple, honeydew melon, pear, and banana. Most of the antioxidant capacity of these fruits was from the juice fractions. The contribution of the fruit pulp fraction (extracted with acetone) to the total ORAC activity of a fruit was usually less than 10%. Among the commercial fruit juices, grape juice had the highest ORAC activity followed by grapefruit juice, tomato juice, orange juice, and apple juice.
Anthocyanins are natural colorants belonging to the flavonoid family. They are widely distributed among flowers, fruits, and vegetables. Using the automated oxygen radical absorbance capacity (ORAC) assay developed in our laboratory, we determined the antioxidant capacity of 14 anthocyanins including the aglycons delphinidin, cyanindin, pelargonidin, malvidin, peonidin, and their derivatives with different sugar linkages. Among these anthocyanins, kuromanin (cyanidin-3-glucoside) had the highest ORAC activity, which was 3.5 times stronger than Trolox (vitamin E analogue), while pelargonin had the lowest antioxidant activity but was still as potent as Trolox. Different patterns of hydroxylation and glycosylation in anthocyanins appear to modulate their antioxidant properties. Therefore, in addition to their colorful characteristics, anthocyanins possess potent antioxidant properties.
The major flavonol glycosides of ripe blackcurrants (Ribes nigrum cv. Silvergieters Schwarze), myricetin 3-beta-D-glucopyranoside, rutin, and isoquercitrin, have been isolated in crystalline form. Analysis by thin-layer chromatography confirmed the occurrence of the 3-rutinosides and 3-glucosides of cyanidin and delphinidin. No free flavonoid aglycones could, however, be detected in the fresh berries. The major constituent fluorescing blue under ultraviolet light on paper and cellulose thin-layer chromatograms, was isolated and characterized as 1-O-caffeyl-beta-D-glucopyranose. Also isolated were 1-O-ferulyl- and 1-O-p-coumaryl-beta-D-glucopyranose. The occurrence fo hydroxycinnamyl-D-glucoses in blackcurrants does not appear to have been recognized previously.
Flavonoids are polyphenolic antioxidants naturally present in vegetables, fruits, and beverages such as tea and wine. In vitro, flavonoids inhibit oxidation of low-density lipoprotein and reduce thrombotic tendency, but their effects on atherosclerotic complications in human beings are unknown. We measured the content in various foods of the flavonoids quercetin, kaempferol, myricetin, apigenin, and luteolin. We then assessed the flavonoid intake of 805 men aged 65-84 years in 1985 by a cross-check dietary history; the men were then followed up for 5 years. Mean baseline flavonoid intake was 25.9 mg daily. The major sources of intake were tea (61%), onions (13%), and apples (10%). Between 1985 and 1990, 43 men died of coronary heart disease. Fatal or non-fatal myocardial infarction occurred in 38 of 693 men with no history of myocardial infarction at baseline. Flavonoid intake (analysed in tertiles) was significantly inversely associated with mortality from coronary heart disease (p for trend = 0.015) and showed an inverse relation with incidence of myocardial infarction, which was of borderline significance (p for trend = 0.08). The relative risk of coronary heart disease mortality in the highest versus the lowest tertile of flavonoid intake was 0.42 (95% CI 0.20-0.88). After adjustment for age, body-mass index, smoking, serum total and high-density-lipoprotein cholesterol, blood pressure, physical activity, coffee consumption, and intake of energy, vitamin C, vitamin E, beta-carotene, and dietary fibre, the risk was still significant (0.32 [0.15-0.71]). Intakes of tea, onions, and apples were also inversely related to coronary heart disease mortality, but these associations were weaker. Flavonoids in regularly consumed foods may reduce the risk of death from coronary heart disease in elderly men.
To study the association between dietary intake of flavonoids and subsequent coronary mortality.
A cohort study based on data collected at the Finnish mobile clinic health examination survey from 1967-72 and followed up until 1992.
30 communities from different parts of Finland.
5133 Finnish men and women aged 30-69 years and free from heart disease at baseline.
Dietary intake of flavonoids, total mortality, and coronary mortality.
In women a significant inverse gradient was observed between dietary intake of flavonoids and total and coronary mortality. The relative risks between highest and lowest quarters of flavonoid intake adjusted for age, smoking, serum cholesterol concentration, blood pressure, and body mass index were 0.69 (95% confidence interval 0.53 to 0.90) and 0.54 (0.33 to 0.87) for total and coronary mortality, respectively. The corresponding values for men were 0.76 (0.63 to 0.93) and 0.78 (0.56 to 1.08), respectively. Adjustment for intake of antioxidant vitamins and fatty acids weakened the associations for women; the relative risks for coronary heart disease were 0.73 (0.41 to 1.32) and 0.67 (0.44 to 1.00) in women and men, respectively. Intakes of onions and apples, the main dietary sources of flavonoids, presented similar associations. The relative risks for coronary mortality between highest and lowest quarters of apple intake were 0.57 (0.36 to 0.91) and 0.81 (0.61 to 1.09) for women and men, respectively. The corresponding values for onions were 0.50 (0.30 to 0.82) and 0.74 (0.53 to 1.02), respectively.
The results suggest that people with very low intakes of flavonoids have higher risks of coronary disease.
The antioxidative activity of a total of 92 phenolic extracts from edible and nonedible plant materials (berries, fruits, vegetables, herbs, cereals, tree materials, plant sprouts, and seeds) was examined by autoxidation of methyl linoleate. The content of total phenolics in the extracts was determined spectrometrically according to the Folin-Ciocalteu procedure and calculated as gallic acid equivalents (GAE). Among edible plant materials, remarkable high antioxidant activity and high total phenolic content (GAE > 20 mg/g) were found in berries, especially aronia and crowberry. Apple extracts (two varieties) showed also strong antioxidant activity even though the total phenolic contents were low (GAE < 12.1 mg/g). Among nonedible plant materials, high activities were found in tree materials, especially in willow bark, spruce needles, pine bark and cork, and birch phloem, and in some medicinal plants including heather, bog-rosemary, willow herb, and meadowsweet. In addition, potato peel and beetroot peel extracts showed strong antioxidant effects. To utilize these significant sources of natural antioxidants, further characterization of the phenolic composition is needed.
Flavonoids are phenolic substances isolated from a wide range of vascular plants, with over 8000 individual compounds known. They act in plants as antioxidants, antimicrobials, photoreceptors, visual attractors, feeding repellants, and for light screening. Many studies have suggested that flavonoids exhibit biological activities, including antiallergenic, antiviral, antiinflammatory, and vasodilating actions. However, most interest has been devoted to the antioxidant activity of flavonoids, which is due to their ability to reduce free radical formation and to scavenge free radicals. The capacity of flavonoids to act as antioxidants in vitro has been the subject of several studies in the past years, and important structure-activity relationships of the antioxidant activity have been established. The antioxidant efficacy of flavonoids in vivo is less documented, presumably because of the limited knowledge on their uptake in humans. Most ingested flavonoids are extensively degraded to various phenolic acids, some of which still possess a radical-scavenging ability. Both the absorbed flavonoids and their metabolites may display an in vivo antioxidant activity, which is evidenced experimentally by the increase of the plasma antioxidant status, the sparing effect on vitamin E of erythrocyte membranes and low-density lipoproteins, and the preservation of erythrocyte membrane polyunsaturated fatty acids. This review presents the current knowledge on structural aspects and in vitro antioxidant capacity of most common flavonoids as well as in vivo antioxidant activity and effects on endogenous antioxidants.
Some of the recent advances in flavonoid research are reviewed. The role of anthocyanins and flavones in providing stable blue flower colours in the angiosperms is outlined. The contribution of leaf flavonoids to UV-B protection in plants is critically discussed. Advances in understanding the part played by flavonoids in warding off microbial infection and protecting plants from herbivory are described. The biological properties of flavonoids are considered in an evaluation of the medicinal and nutritional values of these compounds.
Flavonoids and related plant compounds in fruits and vegetables are of particular importance as they have been found to possess antioxidant and free radical scavenging activity. The HPLC-based quantitative procedure, with improved extraction and hydrolysis, was used to analyze the content of the flavonols quercetin, myricetin, and kaempferol in 10 black currant cultivars from organic farms and in 5 cultivars from conventional farms. Myricetin was the most abundant flavonol, and its amount varied significantly among cultivars, from 8.9 to 24.5 mg x 100 g(-1) (fresh weight). The quercetin levels in black currant also varied widely among the cultivars, from 5.2 to 12.2 mg x 100 g(-1). The kaempferol levels in black currant cultivars were low, ranging from 0.9 to 2.3 mg x 100 g(-1). The sum of these major flavonols varied widely among black currant cultivars. No consistent differences in the contents of flavonols were found between the same black currant cultivars grown in organic and conventional ways. The high variability in the levels of flavonols in different cultivars offers possible avenues for identifying and selecting cultivars rich in certain flavonols for the special production of berries for industrial use.
A method has been established and validated for identification and quantification of individual, as well as total, anthocyanins by HPLC and LC/ES-MS in botanical raw materials used in the herbal supplement industry. The anthocyanins were separated and identified on the basis of their respective M(+) (cation) using LC/ES-MS. Separated anthocyanins were individually calculated against one commercially available anthocyanin external standard (cyanidin-3-glucoside chloride) and expressed as its equivalents. Amounts of each anthocyanin calculated as external standard equivalent were then multiplied by a molecular-weight correction factor to afford their specific quantities. Experimental procedures and use of a molecular-weight correction factors are substantiated and validated using Balaton tart cherry and elderberry as templates. Cyanidin-3-glucoside chloride has been widely used in the botanical industry to calculate total anthocyanins. In our studies on tart cherry and elderberry, its use as external standard followed by use of molecular-weight correction factors should provide relatively accurate results for total anthocyanins, because of the presence of cyanidin as their major anthocyanidin backbone. The method proposed here is simple and has a direct sample preparation procedure without any solid-phase extraction. It enables selection and use of commercially available anthocyanins as external standards for quantification of specific anthocyanins in the sample matrix irrespective of their commercial availability as analytical standards. It can be used as a template and applied for similar quantification in several anthocyanin-containing raw materials for routine quality control procedures, thus providing consistency in analytical testing of botanical raw materials used for manufacturing efficacious and true-to-the-label nutritional supplements.
An improved method of oxygen radical absorbance capacity (ORAC) assay has been developed and validated using fluorescein (3',6'-dihydroxyspiro[isobenzofuran-1[3H],9'[9H]-xanthen]-3-one) as the fluorescent probe. Our results demonstrate that fluorescein (FL) is superior to B-phycoerythrin. The oxidized FL products induced by peroxyl radical were identified by LC/MS, and the reaction mechanism was determined to follow a classic hydrogen atom transfer mechanism. In addition, methodological and mechanistic comparison of ORAC(FL) with other widely used methods was discussed. It is concluded that, unlike other popular methods, the improved ORAC(FL) assay provides a direct measure of hydrophilic chain-breaking antioxidant capacity against peroxyl radical.
Fruits from 107 genotypes of Vaccinium L., Rubus L., and Ribes L., were analyzed for total anthocyanins (ACY), total phenolics (TPH), and antioxidant capacities as determined by oxygen radical absorbing capacity (ORAC) and ferric reducing antioxidant power (FRAP). Fruit size was highly correlated (r = 0.84) with ACY within Vaccinium corymbosum L., but was not correlated to ACY across eight other Vaccinium species, or within 27 blackberry hybrids. Certain Vaccinium and Ribes fruits with pigmented flesh were lower in ACY, TPH, ORAC, and FRAP compared to those values in berries with nonpigmented flesh. ORAC values ranged from 19 to 131 micromol Trolox equivalents/g in Vaccinium, from 13 to 146 in Rubus, and from 17 to 116 in Ribes. Though ACY may indicate TPH, the range observed in ACY/TPH ratios precludes prediction of ACY from TPH and vice versa for a single genotype. In general, TPH was more highly correlated to antioxidant capacity than ACY was. This study demonstrates the wide diversity of phytochemical levels and antioxidant capacities within and across three genera of small fruit.
Multiple health benefits associated with phenolic compounds have raised the interest in the contents of these plant metabolites in foods. Several phenolic compounds were quantified from berries of Ribes nigrum (black and green currants) and Ribes x pallidum (red and white currants), by using sequential extraction with ethyl acetate and methanol and an optimized reversed-phase HPLC method with diode array detection. The highest contents of anthocyanins (3,011 mg/kg fresh weight, expressed as the aglycon) and flavonol glycosides (100 mg/kg) were found in black currant. The lack of anthocyanins in the colorless (green, white) berries was associated with increased levels of phenolic acids, especially p-coumaric acid (80 mg/kg in green currant vs. 45 mg/kg in black currant) and 4-hydroxybenzoic acid (18 mg/kg in white currant vs. 3 mg/kg in red currant). Previously, proanthocyanidins have not been quantified from berries. This study showed that the contents of extractable (22-41 mg/kg) and nonextractable proanthocyanidins (32-108 mg/kg) are comparable to those of other phenolics, with the exception of anthocyanins in black currant. Our results suggest that anthocyanins dominate in black and red currants, whereas proanthocyanidins and phenolic acids are the predominant phenolic compounds in green and white currants.
We recently reported the improved oxygen radical absorbance capacity (ORAC) assay using fluorescein (FL) as the fluorescent probe. The current ORAC(FL) assay is limited in hydrophilic antioxidant due to the aqueous environment of the assay. Lipophilic antioxidants mainly include the vitamin E family and carotenoids, which play a critical role in biological defense systems. In this paper, we expanded the current ORAC(FL) assay to lipophilic antioxidants. Randomly methylated beta-cyclodextrin (RMCD) was introduced as the water solubility enhancer for lipophilic antioxidants. Seven percent RMCD (w/v) in a 50% acetone-H(2)O mixture was found to sufficiently solubilize vitamin E compounds and other lipophilic phenolic antioxidants in 75 mM phosphate buffer (pH 7.4). This newly developed ORAC assay (abbbreviated ORAC(FL-LIPO)) was validated through linearity, precision, accuracy, and ruggedness. The validation results demonstrate that the ORAC(FL-LIPO) assay is reliable and robust. For the first time, by using 6-hydroxy-2,5,7,8-tetramethyl-2-carboxylic acid as a standard (1.0), the ORAC values of alpha-tocopherol, (+)-gamma-tocopherol, (+)-delta-tocopherol, alpha-tocopherol acetate, tocotrienols, 2,6-di-tert-butyl-4-methylphenol, and gamma-oryzanol were determined to be 0.5 +/- 0.02, 0.74 +/- 0.03, 1.36 +/- 0.14, 0.00, 0.91 +/- 0.04, 0.16 +/- 0.01, and 3.00 +/- 0.26, respectively. The structural information of oxidized alpha-tocopherol obtained by liquid chromatography/mass spectrometry reveals that the mechanism for the reaction between the vitamin E and the peroxyl radical follows the hydrogen atom transfer mechanism, which is in agreement with the notion that vitamin E is the chain-breaking antioxidant.
Fifteen anthocyanin structures are reported from an extract of black currant berries (Ribes nigrum L.). These are the 3-O-glucosides and the 3-O-rutinosides of pelargonidin, cyanidin, peonidin, delphinidin, petunidin, and malvidin, cyanidin 3-O-arabinoside, and the 3-O-(6' '-p-coumaroylglucoside)s of cyanidin and delphinidin. The anthocyanins were characterized by means of size exclusion chromatography, high-performance liquid chromatography, UV-visible spectroscopy, and electrospray mass spectrometry. The four main pigments (the 3-O-glucosides and the 3-O-rutinosides of delphinidin and cyanidin) made up >97% of the total anthocyanin content. The minor pigments were enriched from the extract by successive partition against ethyl acetate and by gel fractionation. These chromatographic steps were successfully used to isolate the acylated anthocyanins from the ethyl acetate layer and to separate cyanidin 3-O-arabinoside from the mixture of anthocyanins. The amounts of anthocyanin rutinosides were found to be higher than the amount of the corresponding glucosides for all detected pigments having the same aglycon moiety.
Methods are described for the extraction and analysis of hydrophilic and lipophilic antioxidants, using modifications of the oxygen radical absorbing capacity (ORAC(FL)) procedure. These methods provide, for the first time, the ability to obtain a measure of "total antioxidant capacity" in the protein free plasma, using the same peroxyl radical generator for both lipophilic and hydrophilic antioxidants. Separation of the lipophilic and hydrophilic antioxidant fractions from plasma was accomplished by extracting with hexane after adding water and ethanol to the plasma (hexane/plasma/ethanol/water, 4:1:2:1, v/v). Lipophilic and hydrophilic antioxidants were efficiently partitioned between hexane and aqueous solvents. Conditions for controlling temperature effects and decreasing assay variability using fluorescein as the fluorescent probe were validated in different laboratories. Incubation (37 degrees C for at least 30 min) of the buffer to which AAPH was dissolved was critical in decreasing assay variability. Lipophilic antioxidants represented 33.1 +/- 1.5 and 38.2 +/- 1.9% of the total antioxidant capacity of the protein free plasma in two independent studies of 6 and 10 subjects, respectively. Methods are described for application of the assay techniques to other types of biological and food samples.
Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants. The content of blackberry (Rubus species) juice was investigated by HPLC/ESI/MS using narrow bore HPLC columns. Using this method we demonstrated that cyanidin-3-O-glucoside represents about 80% of the total anthocyanin contents in blackberry extract. Here we investigated antioxidant activity of the blackberry juice and cyanidin-3-O-glucoside on the endothelial dysfunction in cells and in vascular rings exposed to peroxynitrite. In human umbilical vein endothelial cells (HUVEC) in vitro, peroxynitrite caused a significant suppression of mitochondrial respiration (38 +/- 2.1% of control cells), as measured by the mitochondrial-dependent conversion of the dye MTT to formazan. Peroxynitrite caused DNA strand breakage (63 +/- 1.9% single strand vs 3 +/- 0.9% single strand in control cells), as measured by the alkaline unwinding assay, and caused an activation of PARS, as measured by the incorporation of radiolabeled NAD(+) to nuclear proteins. Blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM; 0.028 microM; 0.0085 microM) reduced the peroxynitrite-induced suppression of mitochondrial respiration, DNA damage and PARS activation in HUVECs. Vascular rings exposed to peroxynitrite exhibited reduced endothelium-dependent relaxant responses in response to acetylcholine as well as a vascular contractility dysfunction in response to norepinephrine. The development of this peroxynitrite-induced vascular dysfunction was ameliorated by the blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM;0.028 microM;0.0085 microM). In conclusion our findings clearly demonstrate that blackberry juice containing cyanidin-3-O-glucoside is a scavenger of peroxynitrite and that exert a protective effect against endothelial dysfunction and vascular failure induced by peroxynitrite.
Both lipophilic and hydrophilic antioxidant capacities were determined using the oxygen radical absorbance capacity (ORAC(FL)) assay with fluorescein as the fluorescent probe and 2,2'-azobis(2-amidinopropane) dihydrochloride as a peroxyl radical generator on over 100 different kinds of foods, including fruits, vegetables, nuts, dried fruits, spices, cereals, infant, and other foods. Most of the foods were collected from four different regions and during two different seasons in U.S. markets. Total phenolics of each sample were also measured using the Folin-Ciocalteu reagent. Hydrophilic ORAC(FL) values (H-ORAC(FL)) ranged from 0.87 to 2641 micromol of Trolox equivalents (TE)/g among all of the foods, whereas lipophilic ORAC(FL) values (L-ORAC(FL)) ranged from 0.07 to 1611 micromol of TE/g. Generally, L-ORAC(FL) values were <10% of the H-ORAC(FL) values except for a very few samples. Total antioxidant capacity was calculated by combining L-ORAC(FL) and H-ORAC(FL). Differences of ORAC(FL) values in fruits and vegetables from different seasons and regions were relatively large for some foods but could not be analyzed in detail because of the sampling scheme. Two different processing methods, cooking and peeling, were used on selected foods to evaluate the impact of processing on ORAC(FL). The data demonstrated that processing can have significant effects on ORAC(FL). Considering all of the foods analyzed, the relationship between TP and H-ORAC(FL) showed a very weak correlation. Total hydrophilic and lipophilic antioxidant capacity intakes were calculated to be 5558 and 166 micromol of TE/day, respectively, on the basis of data from the USDA Continuing Survey of Food Intakes by Individuals (1994-1996).
Anthocyanins belong to the flavonoid family and are ubiquitous in plants, especially in flower petals and fruit peels. We established that anthocyanins isolated from fruits of Aronia melanocarpa markedly inhibited the mutagenic activity of benzo(a)pyrene and 2-amino fluorene in the Ames test. In the Sister Chromatid Exchanges (SCEs) test with human blood-derived lymphocytes cultured in vitro, a significant decrease of SCEs frequency induced by benzo(a)pyrene was observed in the presence of anthocyanins. In the case of mitomycin C the effect of anthocyanins on SCEs frequency was smaller but still noticeable. Anthocyanins markedly inhibited the generation and release of superoxide radicals by human granulocytes. The results suggest that the antimutagenic influence of anthocyanins is exerted mainly by their free-radicals scavenging action as well as by the inhibition of enzymes activating promutagens and converting mutagens to the DNA-reacting derivatives. These preliminary data seem to be important in the aspect of a possible antimutagenic and anticarcinogenic potency of anthocyanins commonly present in fruits and vegetables.
Inheritance of four cyanidin-3-glycosides in red currant
- J Oydvin
Oydvin, J. Inheritance of four cyanidin-3-glycosides in red currant. Hortic. Res. 1974, 14, 1-7.
R 2 ) 0.948) and relationship between total ORAC FL and concentrations of proantho-cyanidins (PA) or anthocyanin plus proanthocyanidins (ACN+PA) (B: ORAC FL vs PA, y ) 0.175x + 43
- Orac Fl
- Acn
ORAC FL vs ACN, y ) 0.087x + 35.46, R 2 ) 0.948) and relationship between total ORAC FL and concentrations of proantho-cyanidins (PA) or anthocyanin plus proanthocyanidins (ACN+PA) (B: ORAC FL vs PA, y ) 0.175x + 43.98, R 2 )
R 2 ) 0.911) Points in (B) labeled as CB or EB refer to chokeberry and elderberry, respectively. Anthocyanins, Proanthocyanins, and Antioxidant Capacity in Berries
- Orac Fl
- S E Gebhardt
ORAC FL vs ACN+PA, y ) 0.0709x + 31.074, R 2 ) 0.911). Points in (B) labeled as CB or EB refer to chokeberry and elderberry, respectively. Anthocyanins, Proanthocyanins, and Antioxidant Capacity in Berries J. Agric. Food Chem., Vol. 52, No. 26, 2004 7855 (25) Wu, X.; Gu, L.; Holden, J.; Haytowitz, D.; Gebhardt, S. E.;
Flavans and proanthocyanidins. In The FlaVonoids
- L J Porter
Porter, L. J. Flavans and proanthocyanidins. In The FlaVonoids;