Anthocyanins: Structural characteristics that result in unique metabolic patterns and biological activities

Interest in anthocyanins has increased immensely during the past decade. From these studies, it is clear that anthocyanins have unique properties: Anthocyanins are absorbed intact and absorption can be saturated; acylation of anthocyanins lowers their apparent absorption; anthocyanidin diglycosides in the form of sambubioside or rutinoside impart increased stability to the anthocyanin molecule; and the quantities excreted in urine are less than 0.1% of intake. However, 60–90% of the anthocyanins may disappear from the gastrointestinal tract within 4 h after a meal. What happens to the bulk of the anthocyanins that disappear is not clear. Degradation accounts for a part of this disappearance, but differs for the various aglycones and may be modified further by the nature of the aglycone glycosylation, which further complicates our understanding of this process. Anthocyanins may play an important role in health promotion in terms of obesity prevention, cardiovascular health, anti-inflammatory and anti-cancer effects.     

Effects of anthocyanins and anthocyanin-rich extracts on the risk for cancers of the gastrointestinal tract

Anthocyanins are the largest group of water-soluble pigments in the plant kingdom. Anthocyanins are responsible for most of the red, blue, and purple colors of fruits, vegetables, flowers, and other plant tissues or products. In recent years, numerous studies have shown that anthocyanins display a wide range of biological activities. This review summarises recent literature evidence on the association of anthocyanins and anthocyanin-rich extracts consumption with the risk for gastrointestinal tract cancer, concentrating on the results from in vivo animal model tumor systems, as well as data from human epidemiological studies. Potential cancer chemopreventive activities of anthocyanins were revealed from in vitro studies. In vivo animal model tumor systems showed that dietary anthocyanins inhibit cancers of the gastrointestinal tract. Some epidemiological studies have revealed protective effects of anthocyanins consumption on gastrointestinal cancer risk in humans. Pharmacokinetic data indicate that absorption of anthocyanins into the bloodstream of rodents and humans is minimal, suggesting that they may have little efficacy in tissues other than the gastrointestinal tract and skin. Future studies should be undertaken to determine if the anticancer effects of anthocyanins are due to the parent compounds and/or to their metabolites.     

Red wine anthocyanins are rapidly absorbed in humans and affect monocyte chemoattractant protein 1 levels and antioxidant capacity of plasma

Epidemiological studies suggest that a moderate consumption of anthocyanins may be associated with protection against coronary heart disease. The main dietary sources of anthocyanins include red-coloured fruits and red wine. Although dietary anthocyanins comprise a diverse mixture of molecules, little is known how structural diversity relates to their bioavailability and biological function. The aim of the present study was to evaluate the absorption and metabolism of the 3-monoglucosides of delphinidin, cyanidin, petunidin, peonidin and malvidin in humans and to examine both the effect of consuming a red wine extract on plasma antioxidant status and on monocyte chemoattractant protein 1 production in healthy human subjects. After a 12-h overnight fast, seven healthy volunteers received 12 g of an anthocyanin extract and provided 13 blood samples in the 24 h following the test meal. Furthermore, urine was collected during this 24-h period. Anthocyanins were detected in their intact form in both plasma and urine samples. Other anthocyanin metabolites could also be detected in plasma and urine and were identified as glucuronides of peonidin and malvidin. Anthocyanins and their metabolites appeared in plasma about 30 min after ingestion of the test meal and reached their maximum value around 1.6 h later for glucosides and 2.5 h for glucuronides. Total urinary excretion of red wine anthocyanins was 0.05+/-0.01% of the administered dose within 24 h. About 94% of the excreted anthocyanins was found in urine within 6 h. In spite of the low concentration of anthocyanins found in plasma, an increase in the antioxidant capacity and a decrease in MCP-1 circulating levels in plasma were observed.     

Anthocyanins: from plant to health

Anthocyanins are a group of natural occurring pigments responsible for the red-blue colour of many fruits and vegetables. Anthocyanins are of interest for two reasons because they cannot only be used in the technological field as natural colorants but also have important implications in the field of human health. Numerous studies indicate the potential effect that this family of flavonoids may have in reducing the incidence of cardiovascular disease, cancer, hyperlipidemias and other chronic diseases through the intake of anthocyanin-rich foods. This review examines existing literature in this area: from plant content and distribution to health implications, including the effect of agronomic and genetic modifications on the anthocyanin content of plants as well as other biotechnological factors and food processing. The bioavailability, metabolism, bioactivity, and epidemiology of anthocyanins will also be reviewed.     

花青素及其生物活性的研究进展

花青素是存在于自然界中的天然的水溶性色素,它赋予水果、蔬菜和植物鲜艳的颜色,主要来源于蓝莓、樱桃、覆盆子、草 莓、紫葡萄和红酒等。它属于黄酮类化合物,其结构和化学成分使得花青素具有多种生物活性,如：抗氧化、抗炎、抗衰老、抗心血 管、抗癌等,对于人类的健康具有重要作用。花青素对于人类各种疾病的治疗以及作为一种药方都具有积极的效果,花青素通过 抗细胞增殖、诱导凋亡等多种机制来抑制肿瘤的发生;通过清除活性氧自由基等机制来发挥抗氧化作用;通过抑制各种炎症因子 的表达来发挥抗炎效应,这一系列的生物活性都给人们对抗各种疾病带来了无限的希望。本文就花青素的特点、提取及生物活性 进行了总结,重点介绍了花青素的生物活性。     

Increased accumulation and decreased catabolism of anthocyanins in red grape cell suspension culture following magnesium treatment

Anthocyanins are the largest and best studied group of plant pigments. However, not very much is known about the fate of these phenolic pigments after they have accumulated in the cell vacuoles of plant tissues. We have previously shown that magnesium treatment of ornamentals during the synthesis of anthocyanins in the flowers or foliage caused an increase in the pigment concentration. In this study, we characterized the effect of magnesium on the accumulation of anthocyanin in red cell suspension originating from Vitis vinifera cv. Gamay Red grapes. Magnesium treatment of the cells caused a 2.5- to 4.5-fold increase in anthocyanin concentration, with no substantial induction of the biosynthetic genes. This treatment inhibited the degradation of anthocyanins occurring in the cells, and changed the ratio between different anthocyanins determining cell color, with an increase in the relative concentration of the less stable pigment molecules. The process by which magnesium treatment affects anthocyanin accumulation is still not clear. However, the results presented suggest at least part of its effect on anthocyanin accumulation stems from inhibition of the pigments’ catabolism. When anthocyanin biosynthesis was inhibited, magnesium treatments prevented the constant degradation of anthocyanins in the cell suspension. Future understanding of the catabolic processes undergone by anthocyanins in plants may enable more efficient inhibition of this process and increased accumulation of these pigments, and possibly of additional phenolic compounds.     

Anthocyanins from black soybean inhibit Helicobacter pylori‐induced inflammation in human gastric epithelial AGS cells

Infection with Helicobacter pylori leads to gastritis, peptic ulcers and gastric cancer. Moreover, when the gastric mucosa is exposed to H. pylori, gastric mucosal inflammatory cytokine interleukin‐8 (Il‐8) and reactive oxygen species increase. Anthocyanins have anti‐oxidative, antibacterial and anti‐inflammatory properties. However, the effect of anthocyanins in H. pylori‐infected cells is not yet clear. In this study, therefore, the effect of anthocyanins on H. pylori‐infected human gastric epithelial cells was examined. AGS cells were pretreated with anthocyanins for 24 hrs followed by H. pylori 26695 infection for up to 24 hrs. Cell viability and ROS production were examined by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide and 2′,7′–dichlorofluorescein diacetate assay, respectively. Western blot analyses and RT‐PCR were performed to assess gene and protein expression, respectively. IL‐8 secretion in AGS cells was measured by ELISA. It was found that anthocyanins decrease H. pylori‐induced ROS enhancement. Anthocyanins also inhibited phosphorylation of mitogen‐activated protein kinases, translocation of nuclear factor‐kappa B and Iκβα degradation. Furthermore anthocyanins inhibited H. pylori‐induced inducible nitric oxide synthases and cyclooxygenase‐2 mRNA expression and inhibited IL‐8 production by 45.8%. Based on the above findings, anthocyanins might have an anti‐inflammatory effect in H. pylori‐infected gastric epithelial cells.     

Using fluorescence lifetime microscopy to study the subcellular localization of anthocyanins

Anthocyanins are flavonoid pigments that accumulate in most seed plants. They are synthesized in the cytoplasm but accumulate inside the vacuoles. Anthocyanins are pigmented at the lower vacuolar pH, but in the cytoplasm they can be visualized based on their fluorescence properties. Thus, anthocyanins provide an ideal system for the development of new methods to investigate cytoplasmic pools and association with other molecular components. We have analyzed the fluorescence decay of anthocyanins by fluorescence lifetime imaging microscopy (FLIM), in both in vitro and in vivo conditions, using wild‐type and mutant Arabidopsis thaliana seedlings. Within plant cells, the amplitude‐weighted mean fluorescence lifetime (τ_m) correlated with distinct subcellular localizations of anthocyanins. The vacuolar pool of anthocyanins exhibited shorter τ_m than the cytoplasmic pool. Consistently, lowering the pH of anthocyanins in solution shortened their fluorescence decay. We propose that FLIM is a useful tool for understanding the trafficking of anthocyanins and, potentially, for estimating vacuolar pH inside intact plant cells.     

脱落酸激素诱导拟南芥幼苗中花青素的合成

脱落酸(abscisic acid,ABA)激素是一类重要的生长调节物质,参与调控植物的多种生理过程。花青素(anthocyanins)是植物次生代谢产生的类黄酮化合物,对植物的生长发育和逆境胁迫响应有重要作用。该文以拟南芥(Arabidopsis thaliana)为研究对象,探讨ABA信号对花青素生物合成的调控功能和作用机制。结果表明:外源施加ABA显著提高野生型幼苗茎尖中花青素的积累。相一致的是,ABA能诱导某些与花青素合成相关的转录因子及合成酶基因的表达。遗传学分析发现,ABA诱导花青素合成部分依赖于MBW复合体中的核心转录因子,如TTG1、TT8及MYB75等。初步机制研究揭示,ABA信号途径中的bZIP类转录因子ABI5能与TTG1、TT8及MYB75等相互作用形成蛋白复合物。综上结果认为,ABA信号诱导拟南芥幼苗中花青素的积累,并可能通过ABI5与MBW复合体协同作用调控花青素的合成。     

茄科蔬菜花青素苷分子调控研究进展

花青素苷是一种分布广泛的水溶性色素,不仅赋予了果实多彩的外表,还是天然食用色素的重要来源。近年来有关茄科蔬菜花青素苷的研究逐渐增多,文中从花青素苷结构及其生物合成途径、茄科蔬菜中花青素苷合成代谢的结构基因和调节基因、影响合成的环境因素等方面进行回顾和总结,为进一步阐明茄科蔬菜花青素苷的合成及调控机理、更好利用花青素苷进行果色品质育种的创新提供一些参考。     

Functional role of anthocyanins in the leaves of Quintinia serrata A. Cunn

The protective functions that have been ascribed to anthocyanins in leaves can be performed as effectively by a number of other compounds. The possibility that anthocyanins accumulate most abundantly in leaves deficient in other phytoprotective pigments has been tested. Pigment concentrations and their histological distribution were surveyed for a sample of 1000 leaves from a forest population of Quintinia serrata, which displays natural polymorphism in leaf colour. Eight leaf phenotypes were recognized according to their patterns of red coloration. Anthocyanins were observed in almost all combinations of every leaf tissue, but were most commonly located in the vacuoles of photosynthetic cells. Red leaves contained two anthocyanins (Cy-3-glc and Cy-3-gal), epicuticular flavones, epidermal flavonols, hydroxycinnamic acids, chlorophylls, and carotenoids. Green leaves lacked anthocyanins, but had otherwise similar pigment profiles. Foliar anthocyanin levels varied significantly between branches and among trees, but were not correlated to concentrations of other pigments. Anthocyanins were most abundant in older leaves on trees under canopies with south-facing gaps. These data indicate that anthocyanins are associated with photosynthesis, but do not serve an auxiliary phytoprotective role. They may serve to protect shade-adapted chloroplasts from brief exposure to high intensity sunflecks.     

In vitro anticancer properties of anthocyanins: A systematic review

Anthocyanins have been associated with beneficial effects on human health. Cancer has been one of the main public health issues due to its aggressiveness and high mortality rate. This systematic review aimed to address recent research (from January 2000 to September 2021) on the anticancer activity of anthocyanins assessed by in vitro assays. The selected studies revealed that anthocyanins have anticancer potential by inhibiting cancer cell viability and proliferation, controlling cell cycle, and promoting apoptosis.,     

Genetic Differentiation in Anthocyanin Content among Berry Fruits

Anthocyanins are widely distributed secondary metabolites that play an essential role in skin pigmentation of many plant organs and microorganisms. Anthocyanins have been associated with a wide range of biological and pharmacological properties. They are also effective agents in the prevention and treatment of many chronic diseases. Berries are particularly abundant in these compounds; therefore, their dietary intake has health-promoting effects. The aim of this study was to identify and determine the anthocyanin content in selected species and cultivars of berry fruits, such as raspberry, blackberry, red currant, blackcurrant, and highbush blueberry, widely consumed by Europeans. The concentrations of anthocyanins were determined by HPLC, identifying individual compounds: cyanidin-3-O-glucoside, pelargonidin-3-O-glucoside, delphinidin-3-O-glucoside, delphinidin-3-O-rutinoside, cyanidin-3-O-rutinoside, delphinidin-3-O-galactoside, cyanidin-3-O-galactoside, and malvidin-3-O-galactoside. The experimental data showed that the selected species and cultivars of berry fruits differ significantly in the contents of anthocyanins. Among all species tested, blackberry and blackcurrant were characterized significantly by the highest content of anthocyanins (sum), while the lowest content was found in red currant fruits. Additionally, the content of individual anthocyanin compounds in particular species and cultivars was also different. Considering the high content of anthocyanins and their potential positive impact on human health and protection against disease, berries should be part of healthy nutrition.     

Osservazioni Sulla Germinazione Asimbiotica e Simbiotica di Alcune Orchidee

Abstract

Anthocyanins are secondary metabolites, which play important roles in the physiology of plants. In tomato (Solanum lycopersicum L.), anthocyanins are normally synthesized only in vegetative tissues. M375 is a mutant unable to produce anthocyanins in leaves and stems. In this study, we investigated the anthocyanin biosynthetic pathway in M375 and in its genetic background, Alice, in order to find out where the anthocyanin biosynthesis is blocked, along the pathway, in the mutant. Anthocyanins accumulation was enhanced by sucrose only in the wild type, even though the expression of several genes involved in anthocyanin biosynthesis was normal in both the genotypes. Genes coding for the final steps along the anthocyanin biosynthetic pathway were, however, less expressed in the M375 when compared to the wild type.     

花青素转录因子调控机制及代谢工程研究进展

花青素是广泛存在于植物中的一类重要的类黄酮化合物, 在植物生长发育和人类营养保健方面具有重要价值。花青素的生物合成途径已经解析得比较清楚, 但花青素的代谢调控网络还在不断完善。调控花青素生物合成的转录因子主要包括MYB、bHLH和WD40三大类, 这些转录因子通过激活或抑制CHS、ANS和DFR等花青素途径关键结构基因的表达水平, 进而决定花青素积累的部位与水平。该文结合国内外花青素生物合成与转录调控方面的研究进展, 简要介绍了花青素的生物合成途径, 归纳总结了模式植物中花青素代谢调控的分子机理, 尤其是MYB、bHLH和WD40三类主要转录因子的调控机理, 以及这些转录因子在观赏植物和水果等经济作物花青素代谢工程中的应用。该文将为系统阐明花青素的转录调控机制和利用代谢工程改良花青素的相关研究提供有益参考。     

Urinary excretion of cyanidin glycosides

Anthocyanins, which are natural plant pigments from the flavonoid family, represent substantial constituents of the human diet. Several fruits (blackcurrant, blue berries, red grape and elderberry) are rich sources of these efficient antioxidant compounds. The present study was designed to determine the potential bioavailability in humans of the anthocyanins of elderberry, mainly cyanidin-3-glucoside and cyanidin-3-sambubioside, and the influence of the simultaneous ingestion of sucrose on the absorption of anthocyanins. Urinary samples from 16 healthy volunteers--8 women and 8 men--were collected before and over a period of 6 h with intervals of 1 h after the ingestion of 11 g elderberry concentrate (containing 1.9 g of anthocyanins equivalent to 235 ml of fresh juice) 1 day diluted with water, the other day with 30 g sucrose. Using high-performance liquid chromatography, it was possible to quantify the two main anthocyanins of elderberry excreted unchanged in the urine (0.003-0.012% of the oral dose). The ingestion of sucrose led to a reduced excretion of anthocyanins.     

New insights into the bioavailability of red raspberry anthocyanins and ellagitannins

Red raspberries, containing ellagitannins and cyanidin-based anthocyanins, were fed to volunteers and metabolites appearing in plasma and urine were analysed by UHPLC-MS. Anthocyanins were not absorbed to any extent with sub nmol/L concentrations of cyanidin-3-O-glucoside and a cyanidin-O-glucuronide appearing transiently in plasma. Anthocyanins excreted in urine corresponded to 0.007% of intake. More substantial amounts of phase II metabolites of ferulic acid and isoferulic acid, along with 4′-hydroxyhippuric acid, potentially originating from pH-mediated degradation of cyanidin in the proximal gastrointestinal tract, appeared in urine and also plasma where peak concentrations were attained 1–1.5 h after raspberry intake. Excretion of 18 anthocyanin-derived metabolites corresponded to 15.0% of intake, a figure substantially higher than obtained in other anthocyanin feeding studies. Ellagitannins pass from the small to the large intestine where the colonic microbiota mediate their conversion to urolithins A and B which appeared in plasma and were excreted almost exclusively as sulfate and glucuronide metabolites. The urolithin metabolites persisted in the circulatory system and were excreted in urine for much longer periods of time than the anthocyanin metabolites although their overall urinary recovery was lower at 7.0% of intake. It is events originating in the proximal and distal gastrointestinal tract, and subsequent phase II metabolism, that play an important role in the bioavailability of both anthocyanins and ellagitannins and it is their metabolites which appear in the circulatory system, that are key to elucidating the mode of action(s) underlying the protective effects of these compounds on human health.     

Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries

Anthocyanins from tart cherries, Prunus cerasus L. (Rosaceae) cv. Balaton and Montmorency; sweet cherries, Prunus avium L. (Rosaceae); bilberries, Vaccinum myrtillus L. (Ericaceae); blackberries, Rubus sp. (Rosaceae); blueberries var. Jersey, Vaccinium corymbosum L. (Ericaceae); cranberries var. Early Black, Vaccinium macrocarpon Ait. (Ericaceae); elderberries, Sambucus canadensis (Caprifoliaceae); raspberries, Rubus idaeus (Rosaceae); and strawberries var. Honeoye, Fragaria x ananassa Duch. (Rosaceae), were investigated for cyclooxygenase inhibitory and antioxidant activities. The presence and levels of cyanidin-3-glucosylrutinoside 1 and cyanidin-3-rutinoside 2 were determined in the fruits using HPLC. The antioxidant activity of anthocyanins from cherries was comparable to the commercial antioxidants, tert-butylhydroquinone, butylated hydroxytoluene and butylated hydroxyanisole, and superior to vitamin E, at a test concentration of 125 microg/ml. Anthocyanins from raspberries and sweet cherries demonstrated 45% and 47% cyclooxygenase-I and cyclooxygenase-II inhibitory activities, respectively, when assayed at 125 microg/ml. The cyclooxygenase inhibitory activities of anthocyanins from these fruits were comparable to those of ibuprofen and naproxen at 10 microM concentrations. Anthocyanins 1 and 2 are present in both cherries and raspberry. The yields of pure anthocyanins 1 and 2 in 100 g Balaton and Montmorency tart cherries, sweet cherries and raspberries were 21, 16.5; 11, 5; 4.95, 21; and 4.65, 13.5 mg, respectively. Fresh blackberries and strawberries contained only anthocyanin 2 in yields of 24 and 22.5 mg/100 g, respectively. Anthocyanins 1 and 2 were not found in bilberries, blueberries, cranberries or elderberries.     

Structural requirements of anthocyanins in relation to inhibition of endothelial injury induced by oxidized low-density lipoprotein and correlation with radical scavenging activity

Anthocyanins may play an important role in atherosclerosis prevention. However, the structure-function relationships are not well understood. The objective of this study was to compare the inhibitory effect of 21 anthocyanins against oxidized low-density lipoprotein-induced endothelial injury to understand the relationship between anthocyanin chemical structure and the endothelial protective properties, measured as cell viability, MDA production and NO release. Additionally, the intracellular anti-radical activity of the selected anthocyanins was investigated to identify the correlation with endothelial protection. Our results provide evidence that the number of -OH in total or in B-ring, 3′,4′-ortho-dihydroxyl and 3-hydroxyl are the main structural requirements of anthocyanins in suppressing oxidative stress-induced endothelial injury and such inhibitory effect was significantly correlated with the intracellular radical scavenging activity.     

Anthocyanins of the Melastomataceae,Myrtaceae and some allied families

Acylated anthocyanins were found to be abundant in the Melastomataceae but were not found in closely allied families. Their distribution may help in placing Memecylon. Anthocyanins of Barringtonia support the separation of the Lecythidaceae from the Myrtiflorae.